U.S. patent application number 14/464761 was filed with the patent office on 2014-12-04 for composition made of polyalkoxylated derivatives of trimethylolpropane and fatty alcohols, method for preparing said composition, and use thereof as a reverser in self-reversible reverse latexes.
The applicant listed for this patent is SOCIETE D'EXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES SEPPIC. Invention is credited to Olivier BRAUN, Georges DA COSTA, Paul MALLO, Herve ROLLAND.
Application Number | 20140357735 14/464761 |
Document ID | / |
Family ID | 42358614 |
Filed Date | 2014-12-04 |
United States Patent
Application |
20140357735 |
Kind Code |
A1 |
MALLO; Paul ; et
al. |
December 4, 2014 |
COMPOSITION MADE OF POLYALKOXYLATED DERIVATIVES OF
TRIMETHYLOLPROPANE AND FATTY ALCOHOLS, METHOD FOR PREPARING SAID
COMPOSITION, AND USE THEREOF AS A REVERSER IN SELF-REVERSIBLE
REVERSE LATEXES
Abstract
The invention relates to a novel composition made of
polyalkoxylated derivatives of trimethylolpropane and fatty
alcohols, said composition lending itself to the preparation
thereof and to the use thereof as a reversing agent for a
reversible reverse latex.
Inventors: |
MALLO; Paul;
(Croissy-Sur-Seine, FR) ; ROLLAND; Herve;
(Castres, FR) ; DA COSTA; Georges; (Saix, FR)
; BRAUN; Olivier; (Castres, FR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
SOCIETE D'EXPLOITATION DE PRODUITS POUR LES INDUSTRIES CHIMIQUES
SEPPIC |
Paris |
|
FR |
|
|
Family ID: |
42358614 |
Appl. No.: |
14/464761 |
Filed: |
August 21, 2014 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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13696311 |
Nov 6, 2012 |
8846769 |
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PCT/FR2011/050817 |
Apr 11, 2011 |
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14464761 |
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Current U.S.
Class: |
516/76 |
Current CPC
Class: |
C07C 41/01 20130101;
C08F 220/06 20130101; C07C 41/01 20130101; C08K 5/05 20130101; C08K
5/1525 20130101; C08F 222/385 20130101; C08F 220/06 20130101; C08F
222/385 20130101; C08F 220/281 20200201; C08F 222/385 20130101;
C07C 43/135 20130101; C08F 222/385 20130101; C08F 220/58 20130101;
C08F 220/281 20200201; C08F 220/281 20200201; C08F 220/56 20130101;
C08F 220/56 20130101; C08F 2/32 20130101; C08F 220/286 20200201;
C08F 220/58 20130101; C08F 220/585 20200201; C08F 222/385 20130101;
C08F 220/286 20200201; C08F 220/06 20130101; C08F 220/286 20200201;
C08F 220/286 20200201; C08F 220/06 20130101; C08F 220/585 20200201;
B01F 17/0021 20130101; C08F 220/585 20200201; C08F 220/585
20200201; C08F 220/06 20130101; B01F 17/0028 20130101; C08K 5/06
20130101; C07C 43/135 20130101 |
Class at
Publication: |
516/76 |
International
Class: |
B01F 17/00 20060101
B01F017/00 |
Foreign Application Data
Date |
Code |
Application Number |
May 6, 2010 |
FR |
10 53532 |
Claims
1. A surfactant composition (C) comprising, per 100 mol %: 1)--a
proportion of greater than or equal to 10 coif and of less than or
equal to 50 mol % of a composition (C.sub.II) comprising, per 100
mol %: .alpha.)--from 60 mol % to 100 mol % of a compound of
formula (II): ##STR00024## in which: R2 represents a linear or
branched alkyl radical comprising 12 carbon atoms, T.sub.1
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m1--H radical in which m1 is an
integer of greater than or equal to zero and less than or equal to
ten, T.sub.2, which is identical to or different from T.sub.1
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m2--H radical in which m2 is an
integer of greater than or equal to zero and less than or equal to
ten, and T.sub.3, which is identical to or different from T.sub.1
and T.sub.2, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m3--H radical in which m3 is an
integer of greater than or equal to zero and less than or equal to
ten, it being understood that the sum m1+m2+m3 is greater than 0
and less than or equal to ten; .beta.)--optionally up to 40 mol %
of a compound of formula (II'): ##STR00025## in which: R'.sub.2
represents a linear or branched alkyl radical comprising 14 carbon
atoms, T'.sub.2 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m1--H radical in which m1 is an
integer of greater than or equal to zero and less than or equal to
ten, T'.sub.2, which is identical to or different from T'.sub.1,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m2--H radical in which m2 is an
integer of greater than or equal to zero and less than or equal to
ten, and T'.sub.3, which is identical to or different from T'.sub.1
and T'.sub.2, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m3--H radical in which m3 is an
integer of greater than or equal to zero and less than or equal to
ten, it being understood that the sum m1+m2+m3 is greater than 0
and less than or equal to ten; and .gamma.)--optionally up to 10
mol %, of a compound of formula (II''): ##STR00026## in which:
R''.sub.2 represents a linear or branched alkyl radical comprising
16 carbon atoms, T''.sub.1 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m1--H radical in which m1 is an
integer of greater than or equal to zero and less than or equal to
ten, T''.sub.2, which is identical to or different from T''.sub.1,
if represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m2--H radical in which m2 is an
integer of greater than or equal to zero and less than or equal to
ten, and T''.sub.3, which is identical to or different from
T''.sub.1 and T''.sub.2, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m3--H radical in which m3 is an
integer of greater than or equal to zero and less than or equal to
ten, it being understood that the sum m1+m2+m3 is greater than 0
and less than or equal to ten; 2)--a proportion of greater than or
equal to 50 mol % and of less than or equal to 90 mol % of a
composition (C.sub.III) comprising, per 100 mol %: .alpha.)--from
60 mol % to 100 mol % of a compound of formula (III): ##STR00027##
or of its isomer of formula (IV): ##STR00028## or of the mixture of
these two isomers, in which formulae (III) and (IV): R2 represents
a linear or branched alkyl radical comprising 12 carbon atoms,
T.sub.4 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m4--H radical in which m4 is an
integer of greater than or equal to zero and less than or equal to
ten, T.sub.5, which is identical to or different from T.sub.4,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m5--H radical in which m5 is an
integer of greater than or equal to zero and less than or equal to
ten, T.sub.6, which is identical to or different from T.sub.4 and
T.sub.5, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m6--H radical in which m6 is an
integer of greater than or equal to zero and less than or equal to
ten, T.sub.7, which is identical to or different from T.sub.4,
T.sub.5 and T.sub.6, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m7--H radical in which m7 is an
integer of greater than or equal to zero and less than or equal to
ten, it being understood that the sum m4+m5+m6+m7 is greater than 0
and less than or equal to ten; .beta.)--optionally up to 40 mol %
of a compound of formula (III'): ##STR00029## or of its isomer of
formula (IV'): ##STR00030## or of the mixture of these two isomers,
in which formulae (III') and (IV'): R'.sub.2 represents a linear or
branched alkyl radical comprising 14 carbon atoms, T'.sub.4
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m4--H radical in which m4 is an
integer of greater than or equal to zero and less than or equal to
ten, T'.sub.5, which is identical to or different from T'.sub.4,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m5--H radical, in which m5 is an
integer of greater than or equal to zero and less than or equal to
ten, T'.sub.6, which is identical to or different from T'.sub.4 and
T'.sub.5, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m6--H radical in which m6 is an
integer of greater than or equal to zero and less than or equal to
ten, and T'.sub.7, which is identical to or different from
T'.sub.4, T'.sub.5, and T'.sub.6, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m7--H radical in which m7 is an
integer of greater than or equal to zero and less than or equal to
ten, it being understood that the sum m4+m5+m6+m7 is (greater than
0 and less than or equal to ten; and .gamma.)--optionally up to 10
mol % of a compound of formula (III''): ##STR00031## or of its
isomer of formula (IV''): ##STR00032## or of the mixture of these
two isomers, in which formulae (III'') and (IV''): R'.sub.2
represents a linear or branched alkyl radical comprising 16 carbon
atoms, T''.sub.4 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m4--H radical in which m4 is an
integer of greater than or equal to zero and less than or equal to
ten, T''.sub.5, which is identical to or different from T''.sub.4,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m5--H radical in which m5 is an
integer of greater than or equal to zero and less than or equal to
ten, T''.sub.6, which is identical to or different from T''.sub.4
and T''.sub.5, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m6--H radical in which m6 is an
integer of greater than or equal to zero and less than or equal to
ten, and T''.sub.7, which is identical to or different from
T''.sub.4, T''.sub.5 and T''.sub.6, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m7--H radical in which m7 is an
integer of greater than or equal to zero and less than or equal to
ten, it being understood that the sum m4+m5+m6+m7 is greater than 0
and less than or equal to ten.
2. The surfactant composition (C) as defined in claim 1,
additionally comprising: 3)--up to 5 mol % of a composition
(C.sub.V) comprising, per 100 mol %: .alpha.)--from 60 mol % to 100
mol % of a compound of formula (V): ##STR00033## in which: R2
represents a linear or branched alk radical comprising 12 carbon
atoms, T.sub.8 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m8--H radical in which m8 is an
integer of greater than or equal to zero and less than or equal to
ten, T.sub.9, which is identical to or different from T.sub.8,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m9--H radical in which m9 is an
integer of greater than or equal to zero and less than or equal to
ten, and it being understood that the sum m8+m9 is greater than 0
and less than or equal to ten; .beta.)--optionally up to 40 mol %
of a compound of formula (V'): ##STR00034## in which: R'.sub.2
represents a linear or branched alkyl radical comprising 14 carbon
atoms, T'.sub.8 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m8--H radical in which m8 is an
integer of greater than or equal to zero and less than or equal to
ten, T'.sub.9, which is identical to or different from T'.sub.8,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m9--H radical in which m9 is an
integer of greater than or equal to zero and less than or equal to
ten, and it being understood that the sum m8+m9 is greater than 0
and less than or equal to ten; and .gamma.)--optionally up to 10
mol % of a compound of formula (V''): ##STR00035## in which:
R''.sub.2 represents a linear or branched alkyl radical comprising
16 carbon atoms, T''.sub.8 represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m8--H radical in which m8 is an
integer of greater than or equal to zero and less than or equal to
ten, T'.sub.9, which is identical to or different from T''.sub.8,
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m9--H radical, in which m9 is an
integer of greater than or equal to zero and less than or equal to
ten, and it being understood that the sum m8+m9 is greater than 0
and less than or equal to ten.
3. The active composition (C) as defined in claim 1, additionally
comprising: 4)--up to 5 mol % of a composition (C.sub.VI)
comprising, per 100 mol %: .alpha.)--from 60 mol % to 100 mol % of
a compound of formula (VI):
R2-(--CH.sub.2--CH.sub.2--O--).sub.m10--H (VI), in which R2
represents a linear or branched alkyl radical comprising 12 carbon
atoms and m10 is an integer of greater than or equal to zero and
less charm or equal to ten; .beta.)--optionally up to 40 mol % of a
compound of formula (VI'):
R'.sub.2--(--CH.sub.2--CH.sub.2--O--).sub.m10--H (VI'), in which
R'.sub.2 represents a linear or branched alkyl radical comprising
14 carbon atoms and m10 is an integer of greater than or equal to
zero and less than or equal to ten; and .gamma.)--optionally up to
10 mol % of a compound of formula (VI''):
R''.sub.2--(--CH.sub.2--CH.sub.2--O--).sub.m10--H (VI''), in which
R''.sub.2 represents a linear or branched alkyl radical comprising
16 carbon atoms and m10 is an integer of greater than or equal to
zero and less than or equal to ten.
4. The surfactant composition (C) as defined in claim 1,
characterized in that it comprises: 1)--a proportion of greater
than or equal to 20 mol % and of less than or equal to 50 mol % of
a composition (C.sub.II) as defined above; 2)--a proportion of
greater than or equal to 50 mol % and of less than or equal to 80
mol % of a composition (C.sub.III) as defined above.
5. The surfactant composition (C) as defined in claim 1,
characterized in that: 1)--said composition (C.sub.II) comprises,
per 100 mol %: .alpha.)--from 60 mol % to 80 mol % of the compound
of formula (II), .beta.)--from 15 mol % to 30 mol % of the compound
of formula (II'), and .gamma.)--up to 10 mol % of the compound of
formula (II''), and 2)--said composition (C.sub.III) comprises, per
100 mol %: .alpha.)--from 60 mol % to 80 mol % of the compound of
formula (III), of its isomer of formula (IV) or of the mixture of
these isomers, .beta.)--from 15 mol % to 30 mol % of the compound
of formula (III'), of its isomer of formula (IV') or of the mixture
of these isomers, and .gamma.)--up to 10 mol % of the compound of
formula (III''), of its isomer of formula (IV'') or of the mixture
of these isomers.
6. The surfactant composition (C) as defined in claim 1, wherein
said surfactant is a emulsifying agent of oil-in-water (O/W) type.
Description
FIELD OF THE INVENTION
[0001] The present patent application relates to the use of
compounds derived from trimethylolpropane oxetane as inverters in
self-invertible inverse latexes.
BACKGROUND OF THE INVENTION
[0002] Inverse latexes of polyelectrolytes based on partially Or
completely salified
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid (also
known as 2-acrylamido-2-methylpropanesulfonic acid, ATBS or AMPS),
and their use in cosmetics and/or in pharmaceuticals have formed
the subject matter of numerous patent applications. However, the
presence of significant amounts of water and oil in these inverse
latexes represents a not insignificant disadvantage in terms of
volume, of cost and sometimes of increased risks and/or of toxic
effects.
[0003] Solutions have thus been developed for increasing the
concentration of polyelectrolytes in the final inverse latexes, for
example by subjecting the reaction medium, at the end of
polymerization, to a vacuum distillation stage in order to remove a
more or less large portion of water and oil. However, this
distillation is problematic to carry out as it often brings about a
destabilization of the inverse latex which is necessary to counter
by the prior addition of stabilizing agents.
[0004] European patent applications EP 0 161 038 and EP 0 126 528
and British patent application GB 1482 515 disclose such a use of
stabilizing polymers.
[0005] The disadvantage of these stabilizing products is that they
comprise alcohols or glycols which can cause environmental
problems. Furthermore, sometimes the reaction medium sets solid
during the distillation stage, without this phenomenon ever having
been truly explained, but the certain consequence of which is the
destruction of the batch of inverse latex in the course of
preparation and difficult and expensive cleaning of the reactor
used. Finally, even if the distillation takes place correctly, the
inverse latexes obtained often invert with difficulty when they are
employed in an aqueous phase and they also exhibit a high viscosity
and sometimes microgels within them. These disadvantages thus
prohibit their use in the manufacture of cosmetic formulations
and/or of textile printing pastes. In order to overcome these
disadvantages, the inventors have developed an inverse latex
disclosed in the French patent application published under the
number FR 2 879 607 comprising from 50% to 80% by weight of a
polyelectrolyte comprising from 0.01 mol % to 10 mol % of at least
one monomer unit derived from the compound of formula (A):
C(R.sub.1)(R.sub.3).dbd.C(R.sub.2)--C(.dbd.O)--O--(CH.sub.2--CH2-O.sub.n-
--R.sub.4 (A)
in which the R.sub.1, R.sub.2 and R.sub.3 radicals, which are
identical or different, represent, independently of one another, a
halogen atom or a linear or branched alkyl radical comprising from
1 to 4 carbon atoms, the R.sub.4 radical represents a saturated or
unsaturated and linear or branched aliphatic radical comprising
from 6 to 30 carbon atoms and n represents a number between 1 and
50.
[0006] However, when this composition is used to prepare a
thickened formulation, the rate of inversion of the inverse latex
in the aqueous phase, that is to say the time necessary to obtain
the maximum development of the viscosity, remains fairly low, which
means, for the user, a loss of time during the use of this product,
in particular in the industrial phase for preparing cosmetic
formulations and/or textile printing pastes. This is because it is
well known that the inversion time for inverse latexes increases
very considerably as a function of the scale of use. Furthermore,
the stability over time of the inverse latexes described in FR 2
379 607 is not completely satisfactory. This is because a fairly
rapid phenomenon of release of oil at the surface is observed
during storage.
[0007] The inventors have thus sought to develop inverse latexes
which do not exhibit the abovementioned disadvantages.
SUMMARY OF THE INVENTION
[0008] According to a first aspect, the subject matter of the
invention is a surfactant composition (C) which comprises, per 100
mol %: [0009] 1)--a proportion of greater than or equal to 10 mol %
and of less than or equal to 50 mol % of a composition (C.sub.II)
comprising, per 100 mol %: [0010] .alpha.)--from 60 mol % to 100
mol % of a compound of formula (II):
##STR00001##
[0010] in which: [0011] R2 represents a linear or branched alkyl
radical comprising 12 carbon atoms, [0012] T.sub.1 represents a
hydrogen atom or a (--CH.sub.2--CH.sub.2--O--).sub.m1--H radical in
which m1 is an integer of greater than or equal to zero and less
than or equal to ten, [0013] T.sub.2, which is identical to or
different from T.sub.1, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m2--H radical in which m2 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0014] T.sub.3 which is identical to or different from
T.sub.1 and T.sub.2, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m3--H radical in which m3 is an
integer of greater than or equal to zero and less than or equal to
ten, [0015] it being understood that the sum m1+m2+m3 is greater
than 0 and less than or equal to ten; [0016] .beta.)--optionally up
to 40 mol % of a compound of formula (II'):
##STR00002##
[0016] in which [0017] R'.sub.2 represents a linear or branched
alkyl radical comprising 14 carbon atoms, [0018] T'.sub.1
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m1--H radical in which m1 is an
integer of greater than or equal to zero and less than or equal to
ten, [0019] T'.sub.2, which is identical to or different from
T'.sub.1, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m2--H radical in which m2 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0020] T'.sub.3, which is identical to or different from
T'.sub.1 and T'.sub.2, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m3--H radical in which m3 is an
integer of greater than or equal to zero and less than or equal to
ten, [0021] it being understood that the sum m1+m2+m3 is greater
than 0 and less than or equal to ten; and [0022]
.gamma.)--optionally up to 10 mol % of a compound of formula
(II''):
##STR00003##
[0022] in which: [0023] R''.sub.2 represents a linear or branched
alkyl radical comprising 16 carbon atoms, [0024] T''.sub.1
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m1--H radical in which m1 is an
integer of greater than or equal to zero and less than or equal to
ten, [0025] T''.sub.2, which is identical to or different from
T''.sub.1, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2-O--).sub.m2--H radical in which m2 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0026] T''.sub.3, which is identical to or different from
T''.sub.1 and T''.sub.2, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m3--H radical in which m3 is an
integer of greater than or equal to zero and less than or equal to
ten, [0027] it being understood that the sum m1+m2+m3 is greater
than 0 and less than or equal to ten; [0028] 2)--a proportion of
greater than or equal to 50 mol % and of less than or equal to 90
mol % of a composition (C.sub.II) comprising, per 100 mol %: [0029]
.alpha.)--from 60 mol % to 100 mol % of a compound of formula
(III):
##STR00004##
[0029] or of its isomer of formula (IV):
##STR00005##
or of the mixture of these two isomers, in which formulae (III) and
(IV): [0030] R2 represents a linear or branched alkyl radical
comprising 12 carbon atoms, [0031] T.sub.4 represents a hydrogen
atom or a (--CH.sub.2--CH.sub.2--O--).sub.m4--H radical in which m4
is an integer of greater than or equal to zero and less than or
equal to ten, [0032] T.sub.5, which is identical to or different
from T.sub.4, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m5--H radical in which m5 is an
integer of greater than or equal to zero and less than or equal to
ten, [0033] T.sub.6, which is identical to or different from
T.sub.4 and T.sub.5, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m6--H radical in which m6 is an
integer of greater than or equal to zero and less than or equal to
ten, [0034] T.sub.7, which is identical to or different from
T.sub.4, T.sub.5 and T.sub.6, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m7--H radical in which m7 is an
integer of greater than or equal to zero and less than or equal to
ten, [0035] it being understood that the sum m4+m5+m6+m7 is greater
than 0 and less than or equal to ten; [0036] .beta.)--optionally up
to 40 mol % of a compound of formula (III'):
##STR00006##
[0036] or of its isomer of formula (IV'):
##STR00007##
or of the mixture of these two isomers, in which formulae (III')
and (IV') [0037] R'.sub.2 represents a linear or branched alkyl
radical comprising 14 carbon atoms, [0038] T'.sub.4 represents a
hydrogen atom or a (--CH.sub.2--CH.sub.2--O--).sub.m4--H radical in
which m4 is an integer of greater than or equal to zero and less
than or equal to ten, [0039] T'.sub.5, which is identical to or
different from T'.sub.4, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m5--H radical in which m5 is an
integer of greater than or equal to zero and less than or equal to
ten, [0040] T'.sub.6, which is identical to or different from
T'.sub.4 and T'.sub.5, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m6--H radical in which m6 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0041] T'.sub.7, which is identical to or different from
T'.sub.4, T'.sub.5 and T'.sub.6, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m7--H radical in which m7 is an
integer of greater than or equal to zero and less than or equal to
ten, [0042] it being understood that the sum m4+m5+m6+m7 is greater
than 0 and less than or equal to ten; and [0043]
.gamma.)--optionally up to 10 mol % of a compound of formula
(III''):
##STR00008##
[0043] or of its isomer of formula (IV''):
##STR00009##
or of the mixture of these two isomers, in which formulae (III'')
and (IV''): [0044] R''.sub.2 represents a linear or branched alkyl
radical comprising 16 carbon atoms, [0045] T''.sub.2 represents a
hydrogen atom or a (--CH.sub.2--CH.sub.2--O--).sub.m4--H radical in
which m4 is an integer of greater than or equal to zero and less
than or equal to ten, [0046] T''.sub.5, which is identical to or
different from T'.sub.4, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m5--H radical in which m5 is an
integer of greater than or equal to zero and less than or equal to
ten, [0047] T''.sub.6, which is identical to or different from
T''.sub.4 and T''.sub.5, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m6--H radical in which m6 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0048] T''.sub.7 which is identical to or different from
T''.sub.4, T''.sub.5 and T''.sub.3, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m7--H radical in which m7 is an
integer of greater than or equal to zero and less than or equal to
ten, [0049] it being understood that the sum m4+m5+m6+m7 is greater
than 0 and less than or equal to ten.
[0050] According to another specific aspect of the present
invention, said surfactant composition (C) as defined above
additionally comprises: [0051] 3)--up to 5 mol % of a composition
(C.sub.v) comprising, per 100 mol %: [0052] .alpha.)--from 60 mol %
to 100 mol % of a compound of formula (V):
##STR00010##
[0052] in which: [0053] R2 represents a linear or branched alkyl
radical comprising 12 carbon atoms, [0054] T.sub.8 represents a
hydrogen atom or a (--CH.sub.2--CH.sub.2--O--).sub.m8--H radical in
which m8 is an integer of greater than or equal to zero and less
than or equal to ten, [0055] T.sub.9, which is identical to or
different from T.sub.8, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m9--H radical in which m9 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0056] it being understood that the sum m8+m9 is greater
than 0 and less than or equal to ten; [0057] .beta.)--optionally up
to 40 mol % of a compound of formula (V'):
##STR00011##
[0057] in which: [0058] R'.sub.2 represents a linear or branched
alkyl radical comprising 14 carbon atoms, [0059] T'.sub.8
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m8--H radical in which m8 is an
integer of greater than or equal to zero and less than or equal to
ten, [0060] T'.sub.9, which is identical to or different from
T''.sub.8, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m9--H radical in which m9 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0061] it being understood that the sum m8+m9 is greater
than 0 and less than or equal to ten; and [0062]
.gamma.)--optionally up to 10 mol % of a compound of formula
(V''):
##STR00012##
[0062] in which: [0063] R''.sub.2 represents a linear or branched
alkyl radical comprising 16 carbon atoms, [0064] T''.sub.8
represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m8--H radical in which m8 is an
integer of greater than or equal to zero and less than or equal to
ten, [0065] T''.sub.9, which is identical to or different from
T''.sub.8, represents a hydrogen atom or a
(--CH.sub.2--CH.sub.2--O--).sub.m9--H radical in which m9 is an
integer of greater than or equal to zero and less than or equal to
ten, and [0066] it being understood that the sum m8+m9 is greater
than 0 and less than or equal to ten.
[0067] According to another specific aspect of the present
invention, said active composition (C) as defined above
additionally comprises: [0068] 4)--up to 5 mol % of a composition
(C.sub.VI) comprising, per 100 mol %: [0069] .alpha.)--from 60 mol
% to 100 mol % of a compound of formula (VI):
[0069] R2-(--CH.sub.2--CH.sub.2--O--).sub.m10--H (VI),
in which R2 represents a linear or branched alkyl radical
comprising 12 carbon atoms and m10 is an integer of greater than or
equal to zero and less than or equal to ten; [0070]
.beta.)--optionally up to 40 mol % of a compound of formula
(VI'):
[0070] R'.sub.2--(--CH.sub.2--CH.sub.2--O--).sub.m10--H (VI'),
in which R'.sub.2 represents a linear or branched alkyl radical
comprising 14 carbon atoms and m10 is an integer of greater than or
equal to zero and less than or equal to ten; and [0071]
.gamma.)--optionally up to 10 mol % of a compound of formula
(VI''):
[0071] R''.sub.2--(--CH.sub.2--CH.sub.2--O--).sub.m10--H (VI'),
in which R'.sub.2 represents a linear or branched alkyl radical
comprising 16 carbon atoms and m10 is an integer of greater than or
equal to zero and less than or equal to ten.
[0072] According to a specific aspect of the present invention,
said surfactant composition (C) as defined above comprises [0073]
1)--a proportion of greater than or equal to 20 mol % and of less
than or equal to 50 mol % of composition (C.sub.II) as defined
above; [0074] 2)--a proportion of greater than or equal to 50 mol %
and of less than or equal to 80 mol % of a composition (C.sub.III)
as defined above.
[0075] According to another specific aspect of the present
invention: [0076] 1)--said composition (C.sub.II) comprises, per
100 mol %: [0077] .alpha.)--from 60 mol % to 80 mol % of the
compound of formula (II), [0078] .beta.)--from 15 mol % to 30 mol %
of the compound of formula (II'), and [0079] .gamma.)--up to 10 mol
% of the compound of formula (II''), and [0080] 2)--said
composition (C.sub.III) comprises, per 100 mol %: [0081]
.alpha.)--from 60 mol % to 80 mol % of the compound of formula
(III), of its isomer of formula (IV) or of the mixture of these
isomers, [0082] .beta.)--from 15 mol % to 30 mol % of the compound
of formula (III''), of its isomer of formula (IV') or of the
mixture of these isomers, and [0083] .gamma.)--up to 10 mol % of
the compound of formula (III''), of its isomer of formula (IV'') or
of the mixture of these isomers.
[0084] Another subject matter of the invention is a process for the
preparation of said surfactant composition (C) as defined above,
characterized in that it comprises the following successive
stages:
a stage a) of reaction of a mixture of alcohols comprising, per 100
mol %: from 60 mol % to 100 mol % of a compound of formula
R2-O--H (VII),
in which R2 represents a linear or branched alkyl radical
comprising 12 carbon atoms; optionally up to 40 mol % of a compound
of formula (VII'):
R'.sub.2--O--H (VII'),
in which R'.sub.2 represents a linear or branched alkyl radical
comprising 14 carbon atoms, and optionally up to 10 mol % of a
compound of formula (VI'):
R''.sub.2--O--H (VII''),
in which R''.sub.2 represents a linear or branched alkyl radical
comprising 16 carbon atoms; with a stoichiometric excess of
3-(hydroxymethyl)-3-ethyloxetane of formula (VIII):
##STR00013##
in order to form a composition (C') comprising the compound of
formula (IX):
##STR00014##
in which R2 is as defined above; optionally the compound of formula
(IX'):
##STR00015##
in which R'.sub.2 is as defined above; optionally the compound of
formula (IX''):
##STR00016##
in which R''.sub.2 is as defined above; the compound of formula
(X):
##STR00017##
or its isomer of formula (XI):
##STR00018##
or a mixture of these two isomers; in which compounds of formulae
(X) and (XI) R2 is as defined above; optionally the compound of
formula (X'):
##STR00019##
or its isomer of formula (XI'):
##STR00020##
or a mixture of these two isomers; in which compounds of formulae
(X') and (XI') R'.sub.2 is as defined above; optionally the
compound of formula (X''):
##STR00021##
or its isomer of formula (XI''):
##STR00022##
or a mixture of these two isomers; in which compounds of formulae
(X'') and (XI'') R''.sub.2 is as defined above; a stage b) of
reaction, in the desired stoichiometric ratio, of said composition
(C') with ethylene oxide of formula (XII):
(XII)
in order to form said surfactant composition (C).
[0085] Another subject matter the invention is the intermediate
composition C' of the process as defined above.
[0086] Another subject matter of the invention is the intermediate
compounds of formulae (IX), (X) and (XI) of the process as defined
above.
[0087] A final subject matter of the invention is the use of the
surfactant composition (C) as defined above as emulsifying agent of
oil-in-water (O/W) type and more particularly as emulsifying agent
of oil-in-water (O/W) type, more particularly as inverting agent
for a self invertible inverse latex, alone or as a mixture with
other emulsifying agents capable of preparing and intended to
prepare an emulsifying system (S.sub.2) of oil-in-water (O/W)
type.
DETAILED DESCRIPTION OF THE INVENTION
[0088] The term "self-invertible inverse latex" denotes
water-in-oil emulsion of a crosslinked polymer, obtained by inverse
emulsion polymerization of the monomers employed, said water-in-oil
emulsion of a polymer being capable, by virtue of the presence
within it of an emulsifying system (S.sub.2) of oil-in-water (O/W)
type, said inverting agent, of inverting to give an oil-in-water
emulsion by simple dispersion in water with slow mechanical
stirring, thus bringing about the thickening of this aqueous
phase.
[0089] An example of a self-invertible inverse latex which can
advantageously comprise the surfactant composition (C) as defined
above, within the (S.sub.2) of oil-in-water (O/N) type, is, for
example, a composition comprising, per 100% by weight: [0090] a)
from 20% by weight to 80% by weight of crosslinked and/or branched
anionic polyelectrolyte (P) obtained by polymerization: [0091] of
at least one neutral monomer chosen in particular from acrylamide,
N,N-dimethylacrylamdde,
N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]propenamide [or
tris(hydroxymethyd)acrylamidomethane or
N-[tris(hydroxymethyl)methyl]acrylamide, also known as THAM] or
2-hydroxyethyl acrylate; [0092] and/or [0093] of at least one
monomer comprising a strong acid functional group; [0094] and/or
[0095] of at least one monomer comprising a weak acid functional
group; [0096] and/or [0097] of at least one neutral monomer of
formula (I):
[0097] ##STR00023## [0098] in which the R1 radical represents a
linear or branched aliphatic radical comprising from 8 to 20 carbon
atoms and n represents an integer of greater than or equal to one
and less than or equal to thirty; [0099] b) from 5% by weight to
10% by weight of an emulsifying system (S.sub.1) of water-in-oil
(W/O) type; [0100] c) from 1% by weight to 10% by weight or an
emulsifying system (S.sub.2) of oil-in-water (O/W) type comprising
a non-zero proportion by weight of said surfactant composition (C)
as defined above; [0101] d) from 5% by weight to 45% by weight of
at least one oil, and [0102] e) from 0% by weight to 45% by weight
of water.
[0103] The term "saturated or unsaturated and linear or branched
aliphatic radical comprising from 6 to 20 carbon atoms" denotes,
for the R1 radical in the formula (I) as defined above, more
particularly the linear radicals, such as, for example, the hexyl,
octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl,
octadecyl or eicosyl radicals.
[0104] In the composition as defined above, the emulsifying system
(S.sub.1) of water-in-oil (W/O) type is composed either of lust one
surfactant or of a mixture of surfactants, provided that said
surfactant or said mixture has an HLB value which is sufficiently
low to bring about water-in-oil emulsions. An emulsifying agent of
water-in-oil type is, for example, sorbitan esters, such as
sorbitan oleate, such as that sold by Seppic under the name
Mantane.TM. 80, sorbitan isostearate, such as that sold by Seppic
under the name Montane.TM. 70, or sorbitan sesguiolate, such as
that sold by Seppic under the name Montane.TM. 83. There are also
some polyethoxylated sorbitan esters, for example pentaethoxylated
sorbitan monooleace, such as that sold by Seppic under the name
Monuanox.TM. 81, or pentaethoxylated sorbitan isostearate, such as
that sold under the name Montanox.TM. 71 by Seppic. There is also
diethoxylated oleocetyl alcohol, such as that sold under the name
Simulsol.TM. OC 72 by Seppic, polyesters with a molecular weight of
between 1000 and 3000, products of the condensation between a
polyisobutenyl succinic acid or its anhydride, such as Hypermer.TM.
2296, sold by Unigema, or finally block copolymers with a molecular
weight of between 2500 and 3500, such as Hypermer.TM. P246, sold by
Unigema, or Simaline.TM. IE 200, sold by Seppic.
[0105] In the context of this use, the surfactant composition (C)
as defined above can be employed, alone or as a mixture with at
least one other emulsifying agent of oil-in-water (O/W) type,
within said emulsifying system (S.sub.2) of oil-in-water (O/W)
type, inverting agent for self-invertible inverse latexes.
[0106] According to a specific form of the self-invertible inverse
latexes as defined above, the emulsifying system (S.sub.2) of
oil-in-water (O/W) type consists of 100% by weight of said
surfactant composition (C) as defined above.
[0107] According to another specific form of the self-invertible
inverse latexes as defined above, the emulsifying system (S.sub.2)
of oil-in-water (O/W) type additionally comprises at least one
emulsifying surfactant of the (O/W) type other than one or other of
the compounds constituting said surfactant composition (C) as
defined above.
[0108] The term "emulsifying agent of the oil-in-water type"
denotes emulsifying agents having an HLB value which is
sufficiently high to provide oil-in-water emulsions, such as
ethoxylated sorbitan esters, such as sorbitan oleate
polyethoxylated with 20 mol of ethylene oxide, sold by Seppic under
the name Monfanox.TM. 80, sorbitan laurase polyethoxylated with 20
mol of ethylene oxide, sold by Seppic under the name of
Montanox.TM. 20, castor oil polyethoxylated with 40 mol of ethylene
oxide, sold under the name Simulsol.TM. OL 50, decaethcxylated
oleodecvl alcohol, sold by Seppic under the name Simulsol.TM. OC
710, heptaethoxylated lauryl alcohol, sold under the name
Simulsol.TM. P7, decaethoxylated nonylphenol, sold by Seppic under
the name Nonarox.TM.-10-30, or polyethoxyiated sorbitan
hexaoleates, sold by Seppic under the name Simaline.TM. IE 400.
[0109] According to a more particular form of the self-invertible
inverse latexes as defined above, the emulsifying system (S.sub.2)
of oil-in-water (O/W) type additionally comprises a non-zero
proportion by weight of at least one emulsifying agent of the
oil-in-water type chosen from sorbitan oleate polyethoxylated with
20 mol of ethylene oxide, sorbitan laurate polyethoxylated with 20
mol of ethylene oxide, castor oil polyethoxylated with 40 mol of
ethylene oxide, decaethoxylated oleodecyl alcohol, heptaethoxylated
lauryl alcohol, decaethoxylated nonylphenol or polyethoxylated
sorbitan hexaoleates. According to this specific form, said
emulsifying system (S.sub.2) comprises at least 30% by weight of
said mixture (M) as defined above.
[0110] According to a very specific form of the self-invertible
invert latexes as defined above, the emulsifying system (S.sub.2)
of oil-in-water type comprises, per 100% of its weight: [0111] from
10% by weight to 40% by weight of heptaethoxylated lauryl alcohol
and [0112] from 60% by weight to 90% by weight of the surfactant
composition (C) as defined above.
[0113] The term "crosslinked polyelectrolyte" denotes, for (P), a
non-linear polyelectrolyte which is provided in the form of a
three-dimensional network insoluble in water but swellable with
water and which thus results in a chemical gel being obtained.
[0114] The term "branched polyelectrolyte" denotes, for (P), a
non-linear polymer which has pendent chains, so as to obtain, when
this polymer is dissolved in water, a high state of entanglement,
resulting in very high viscosities with a low gradient.
[0115] The polyelectrolyte (P) is more particularly crosslinked
with a diethylenic or polyethylenic compound in the molar
proportion, expressed with respect to the monomers employed, of
generally less than or equal to 0.40 mol %, mainly of less than
0.25 mol %, more particularly of less than or equal to 0.05 mol %
and very particularly of between 0.005 mol % and 0.01 mol %.
Preferably, the crosslinking agent and/or the branching agent is
chosen from ethylene glycol dimethacrylate, diethylene glycol
diacrylate, sodium diallyloxyacetate, ethylene glycol diacrylate,
diallylurea, triallylamine, trimethylolpropane triacrylate,
methylenebisacrylamide or a mixture of these compounds.
[0116] Examples of constituent crosslinked polyelectrolytes (P) of
said self-invertibie inverse latexes include: [0117] crosslinked
terpolymers of acrylic acid, partially salified in the sodium salt
or ammonium salt form, of acrylamide and of tetraethoxylated lauryl
acrylate; [0118] crosslinked terpolymers of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially salified in the sodium salt form, of acrylamide and of
tetraethoxylated lauryl acrylate; [0119] crosslinked terpolymers of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially salified in the sodium salt form, of acrylic acid,
partially salified in the sodium salt form, and of tetraethoxylated
lauryl acrylate; [0120] crosslinked terpolymers of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially salified in the sodium salt form, of 2-hydroxyethyl
acrylate and of tetraethoxylated lauryl acrylate; [0121]
crosslinked copolymers of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially salified in the sodium salt form, and of tetraethoxylated
lauryl acrylate; [0122] crosslinked copolymers of acrylic acid,
partially salified in the ammonium salt or monoethanolamine salt
form, and of tetraethoxylated lauryl acrylate; [0123] crosslinked
tetrapolymers of acrylamide, of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially salified in the sodium salt form, of acrylic acid,
partially salified in the sodium salt form, and of tetraethoxylated
lauryl acrylate; [0124] tetrapolymers of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially salified in the sodium salt form, of acrylamide, of
vinylpyrrolidone and of tetraethoxylated lauryl acrylate; and
[0125] crosslinked pentapolymers of
2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid,
partially or completely salified in the sodium salt form, of
acrylic acid, partially salified in the sodium salt form, of
2-hydroxyethyl acrylate, of
tris(hydroxymethyl)aminomethylacrylamide and of tetraethoxylated
lauryl acrylate.
[0126] The constituent crosslinked anionic polyelectrolyte (P) of
said self-invertible inverse latexes comprises, per 100% of
monomers employed, more particularly: [0127] from 20 mol % to 80
mol % of monomer units resulting from a monomer comprising either a
strong acid functional group or a weak acid functional group;
[0128] from 15 mol % to 75 mol % of monomer units resulting from a
neutral monomer other than the compound of formula (I) as defined
above; [0129] from 0.5 mol % to 5 mol % of monomer units resulting
from a monomer of formula (I) as defined above.
[0130] According to another specific aspect, the crosslinked
anionic polyelectrolyte (P) comprises, per 100% of monomers
employed: [0131] from 55 mol % to 80 mol % of monomer units
resulting from a monomer comprising a strong acid functional group;
[0132] from 15 mol % to 40 mol % of monomer units resulting from a
neutral monomer other than the compound of formula (I) as defined
above; [0133] from 1 mol % to 5 mol % of monomer units resulting
from a monomer of formula (I) as defined above.
[0134] According to another specific form, said self-invertible
inverse latex as defined above comprises more than 60% by weight
and at most 70% by weight of anionic polyelectrolyte (P).
[0135] In said self-invertible inverse latexes as defined above,
the oil phase is composed either of a commercial mineral oil
comprising saturated hydrocarbons, such as paraffins, isoparaffins
or cycloparaffins, exhibiting, at ambient temperature, a density
between 0.7 and 0.9 and a boiling point of greater than
approximately 250.degree. C., such as, for example, Marcol.TM. 52,
sold by Exxon Chemical, or of a vegetable oil, such as squalane of
vegetable origin, or a synthetic oil, such as hydrogenated
polyisobutene or hydrogenated polydecene, or of a mixture of
several of these oils. Marcol.TM. 52 is a commercial oil
corresponding to the definition of liquid paraffins of the Codex
franoais [French Pharmacopeia]. This is a white mineral oil in
accordance with the FDA 21 CFR 172.878 and CFR 178.3620 (a)
regulations and it is registered in the USA Pharmacopeia, US XXIII
(1995), and in the European Pharmacopoeia (1993). The composition
as defined above can also comprise various additives, such as
complexing agents, chain-transfer agents or chain-limiting
agents.
[0136] The aim of the examples which follow is to illustrate the
present invention without, however, limiting it.
Example A
Preparation of a Surfactant Composition (C) Employed in the
Composition which is a Subject Matter of the Present Invention
Stage A1): Preparation of the Intermediate Composition (C')
[0137] 21 100 g of a mixture of fatty alcohols, comprising from 65%
by weight to 75% by weight of alkanol comprising 12 carbon atoms,
from 21% by weight to 28% by weight of alkanol comprising 14 carbon
atoms and from 4% by weight to 8% by weight of alkanol comprising
16 carbon atoms, heated beforehand, are introduced into a reactor,
are kept stirred and are dried. 326 grams of 50% boron trifluoride
in diethyl ether are subsequently added and then 32 600 g of
3-(hydroxymethyl)-3-ethyloxetane are gradually added with stirring
over 4 hours, the temperature being maintained at approximately
110.degree. C. The reaction medium is then left at 115.degree. C.
for a further 11 hours. The expected composition (C') is then
obtained, which composition is characterized as follows: [0138]
Appearance at 25.degree. C.: Cloudy gel [0139] Acid number (in mg
KOH/g; NFT60-204): 3.9 [0140] Hydroxyl number (in mg KOH/g): 400.5
[0141] Content by weight of free 2-(hydroxymethyl)-2-ethyloxetane
(determined by gas chromatography): <0.05% [0142] Content by
weight of free alkanols (determined by gas chromatography):
C.sub.12 alkanol: 5.7%; C.sub.14 alkanol: 2.0%; C.sub.16 alkanol:
0.5%.
Stage A2): Preparation of the Surfactant Composition (C)
[0143] 50 000 g of the intermediate composition (C') obtained in
the preceding stage A1) are introduced with 75 g of potassium
hydroxide into an autoclave with a capacity of 0.1 m.sup.3 and are
then dried at a temperature of 105.degree. C. An amount of 35 000 g
of ethylene oxide is subsequently gradually introduced while
regulating the temperature of the reaction mixture at a value of
125.degree. C. Once the total amount of ethylene oxide has been
introduced, the reaction mixture is kept stirred at 125.degree. C.
for an additional period of time of one hour. The product then
obtained is subsequently cooled to a temperature of 80.degree. C.
and emptied out. The surfactant composition (C) is then obtained,
which composition is characterized as follows: [0144] Appearance at
30.degree. C.: clear liquid [0145] Color: 125 Alpha [0146] Hydroxyl
number (in mg KOH/g): 252.5 [0147] Acid number (in mg KOH/g)
(NFT60-204): 0.08 [0148] Residual water content: 0.05% [0149] Cloud
point (NF EN 1890E): 76.degree. C. [0150] Content by weight of free
alkanols (gas chromatography): C.sub.12 alkanol: 1.2%; C.sub.14
alkanol: 0.4%; C.sub.16 aikanol: 0.1%, i.e., in total, 1.7% of
residual alkanols [0151] Viscosity an 25.degree. C. (Brookfield
LVT, Rotor 3, Speed 12): 1 072 mPas
Example 1
(According to the Invention): Self-Invertible Inverse Latex of the
ATBS (Na Salt)/HEA/(LA-4EO) [ATBS/HEA/(LA-4EO) 89.0/9.9/1.1 Molar]
Copolymer Crosslinked with MBA
1) Preparation
[0151] [0152] a)--The following are successively introduced with
stirring into a first beaker: [0153] 672.5 g of a 55% by weight
commercial solution of sodium salt of
2-acrylamido-2-methylpropanesulfonic acid (ATBS Na), [0154] 20.8 q
of 2-hydroxyethyl acrylate (HEA) [0155] 0.028 g of
methylenebisacrylamide (MBA) and [0156] 1.0 g of a 40% by weight
commercial solution of sodium diethylenetriaminepentaacetate.
[0157] The pH is then adjusted to 4 therein by adding, if
necessary, the required amounts of
2-acrylamido-2-methylpropanesulfonic acid and deionized water up to
700 g. [0158] b)--The following are successively introduced with
stirring into a second beaker: [0159] 130 g polyisobutene, [0160]
30 g of Marocol.TM. 52, [0161] 90 g of Isopar.TM. H, [0162] 17 g of
Miontane.TM. 70, [0163] 3 g of Hypermer.TM. 6212, [0164] 5 g of
Simaline.TM. IE 200, [0165] 7.2 g of tetraethoxylated lauryl
acrylate (commercial) (LA-4EO), [0166] 0.36 g of dilauroyl peroxide
[0167] c)--The aqueous phase is then incorporated in the organic
phase with stirring and then the preemulsion thus obtained is
subjected to shearing mechanical stirring using a rotor agitator of
Silverson type so as to create a fine emulsion while sparging with
nitrogen. [0168] d)--After cooling to approximately 8.degree. C.,
the polymerization reaction is initiated using the
oxidation/reduction couple: cumene hydroperoxide/sodium
metabisulfite. [0169] e)--Once the polymerization reaction is
complete, the Isopar.TM. H and virtually all of the water are
removed by vacuum distillation. [0170] f)--After introduction of 2%
by weight of Laureth-7 and 4% by weight of the surfactant
composition (C) obtained in example A, the self-invertible inverse
latex (1) is obtained, which latex comprises approximately 63% of
polymer, which is not very viscous, which inverts very rapidly in
water and which has a high thickening power. Furthermore, this
inverse latex is very stable as no phenomenon of syneresis is
observed, in that only a very small amount of oil is released and
that polymer does not sediment out. Its water content, measured by
Karl-Fischer titrimetry, is 1.8% by weight.
2) Viscosity Measurements
[0170] [0171] a)--The viscosity of the self-invertible inverse
latex (1) obtained as indicated in section 1, that of an aqueous
solution devoid of sodium chloride (Sol.1) and those of aqueous
solutions respectively comprising 0.1% by weight (Sol.2) and 1% by
weight (Sol.3) of sodium chloride are measured, said aqueous
solutions each comprising 2% by weight of said self-invertible
inverse latex (1). The results measured using a Brookfield RVT
viscometer are recorded in the following table:
TABLE-US-00001 [0171] Rotor (R); Rotational speed of the rotor (S)
Viscosity (in revolutions per minute) (in mPa s) Inverse latex (1)
R 3, S 20 2700 Sol. 1 R 6, S 5 54 000 Sol. 2 R 6, S 5 27 000 Sol. 3
R 3, S 5 1600
3) Measurement of the Inversion Time and Evaluation of the
Stability of the Inverse Latex
[0172] a)--The inversion time is evaluated by measuring the time
necessary to obtain a smooth and homogeneous gel for a 2% by weight
aqueous solution of self-invertible inverse latex (1) under the
standard conditions for measuring this viscosity, that is to say by
incorporating 16 g of the inverse latex (1) in 784 g of water, the
combined mixture being placed in a 1 liter low-form beaker, and by
then stirring the combined mixture using a butterfly-type
axial-flow impeller rotating at 150 revolutions per minute. The
inversion time is thus a period of time evaluated between starting
the stirrer and the appearance of a smooth and homogeneous medium
in the beaker. In the present example, the inversion time is 58
seconds. [0173] b)--The stability of the inverse latex evaluated by
observing the time for appearance of an oil layer at the surface.
In the present example, the time for appearance of the oil layer at
the surface of the inverse latex (1) is two weeks.
Example T1
(According to the State of the Art): Self-Invertible Inverse Latex
of the ATBS(Na Salt)/HBA/(LA-4EO) [ATBS/HBA/(LA-4EO) 89.0/9.9/1.1
Molar] Copolymer Crosslinked with MBA
1) Preparation
[0174] Stages a) to d) of example 1 are reproduced. In stage f), 4%
by weight of Montanox.TM. 20 are added in place of 4% by weight of
the surfactant composition (C) and the self-invertible inverse
latex (T1) is obtained.
2) Viscosity Measurements
[0175] a)--The viscosity of the self-invertible inverse latex (T1)
obtained as indicated in section 1, that of an aqueous solution
devoid of sodium chloride (Sol.4) and those of aqueous solutions
respectively comprising 0.1% by weight (Sol.5) and 1% by weight
(Sol.6) of sodium chloride are measured, said aqueous solutions
each comprising 2% by weight of said self-invertible inverse latex
(T1). The results measured using a Brookfield RVT viscometer are
recorded in the following table:
TABLE-US-00002 [0175] Rotor (R); Rotational speed of the rotor (S)
Viscosity (in revolutions per minute) (in mPa s) Inverse latex (T1)
R 3, S 20 2900 Sol. 4 R 6, S 5 51 200 Sol. 5 R 6, S 5 25 200 Sol. 6
R 3, S 5 1300
3) Measurement of the Inversion Time and Evaluation of the
Stability of the Inverse Latex
[0176] a)--The inversion time, evaluated in the same way as in the
preceding example, is 2 minutes 20 seconds. [0177] b)--The
stability of the inverse latex (T1) is evaluated in the same way as
in the preceding example. Significant release of oil is observed
after one week.
Example 2
(According to the Invention): Self-Invertible Inverse Latex of the
ATBS(Na Salt)/HEA/(LA-4EO) [ATBS/HEA/(LA-4EO) 89.0/9.9/1.1 Molar]
Copolymer Crosslinked with MBA
1) Preparation
[0178] Stages a) to d) of example 1 are reproduced. In stage f),
only 4% by weight of the surfactant composition (C) are added and
the self-invertible inverse latex (2) is obtained.
2) Viscometry, Measurement of the Inversion Time and Evaluation of
the Stability of the Inverse Latex (2)
[0179] a)--The viscometric performance of the inverse latex (2) is
similar to that reported for the inverse latex of example 1. [0180]
b)--The inversion time of the inverse latex (2), evaluated in the
same way as in example 1, is approximately 40 seconds. [0181]
c)--The stability of the inverse latex (2) is evaluated in the same
way as in example 1. The time for the appearance of the oil layer
is a few days.
Example T2
(According to the State of the Art): Self-Invertible Inverse Latex
of the ATBS(Na Salt)/HEA/(LA-Crosslinked with MBA
1) Preparation
[0182] Stages a) to d) of example 1 are reproduced. In stage f), 4%
by weight of a composition (C''') are added, which composition
comprises, per 100 mol %: [0183] i) a proportion of greater than or
equal to 10 mol % and less than or equal to 50 mol % of a compound
of formula (II''') corresponding to the formula (II) in which R2
represents a linear or branched alkyl radical comprising 10 carbon
atoms and in which the sum m1+m2+m3 is equal to 5; [0184] ii) a
proportion of greater than or equal to 50 mol % and less than or
equal to 90 mol % of a compound of formula (III''') or of its
isomer of formula (IV''') or of the mixture of these two isomers,
formulae (III''') and (IV''') respectively corresponding to the
formulae (III) and (IV) in which R2 represents a linear or branched
alkyl radical comprising 10 carbon atoms and in which the sum
m4+m5+m6+m7 is equal to 5; and the self-invertible inverse latex
(T2) is obtained.
2) Viscometry, Measurement of the Inversion Time and Evaluation of
the Stability of the Inverse Latex (T2)
[0184] [0185] a)--The viscometric performance of the inverse latex
(T2) is similar to that reported for the inverse latex of example
1. [0186] b)--The inversion time of the inverse latex (T2),
evaluated in the same way as in example 1, is approximately 50
seconds. [0187] c)--The stability of the inverse latex (T2)
evaluated in the same way as in example 1. The time for appearance
of she oil layer is a few hours.
Example T3
(According to the State of the Art): Self-Invertible Inverse Latex
of the AM/AA/(LA-4EO) [AM/AA/(LA-4EO) 24.7/74.1 1.2 Molar]
Copolymer Crosslinked with MBA
1) Preparation
[0187] [0188] a)--The following are successively introduced with
stirring into a first beaker: [0189] 106.5 g of a 50% (by weight)
commercial solution of acrylamide (AM), [0190] 162.0 g of glacial
acrylic acid (AA), [0191] 98.1 g of a 29.3% by weight aqueous
ammonia solution, [0192] 0.047 g of methylenebisacrylamide (MBA),
[0193] 0.45 g of a 40% commercial solution of sodium
diethylenetriaminepentaacetate, [0194] deionized water up to 680 g.
[0195] b)--The following are successively introduced with stirring
into a second beaker: [0196] 121 g of polyisobutene, [0197] 28 g of
Marcol.TM. 52, [0198] 99 g of Isopar.TM. H, [0199] 17 g of
Montane.TM. 70, [0200] 3 g of Hypermer.TM. 2296, [0201] 5 g of
Simaline.TM. IE 200, [0202] 1.2 g of tetraethoxylated lauryl
acrylate (commercial) (LA-4EO), [0203] 0.1 g of AIBN. [0204]
c)--The aqueous phase is then incorporated in the organic phase
with stirring and then the preemulson thus obtained is subjected to
shearing mechanical stirring using a rotor agitator of Silverson
type so as to create a fine emulsion while sparging with nitrogen.
[0205] d)--After cooling to approximately 8.degree. C., the
polymerization reaction is initiated using the oxidation/reduction
couple: cumene hydroperoxide/sodium metabisulfite. [0206] e)--Once
the polymerization reaction is complete, the Iscopar.TM. H and
virtually all of the water are removed by vacuum distillation.
[0207] f)--After introduction of 4% of Montanox.TM. 20 and 2% of
Laureth-7, the self-invertible inverse latex (T3) is obtained,
which latex comprises approximately 63% of polymer, which is not
very viscous, which inverts very rapidly in water and which has a
high thickening power. Its water content, measured by Karl-Fischer
titrimetry, is 1.8% by weight.
Viscosity Measurements
[0207] [0208] a)--The viscosity of the self-invertible inverse
latex (T3) obtained as indicated in section 1, that of an aqueous
solution devoid of sodium chloride (Sol.7) and those of aqueous
solutions respectively comprising 0.1% by weight (Sol.8) and 1% by
weight (Sol.9) of sodium chloride are measured, said aqueous
solutions each comprising 2% by weight of said self-invertible
inverse latex (T3). The results measured using a Brookfield PITT
viscometer are recorded in the following table:
TABLE-US-00003 [0208] Rotor (R); Rotational speed of the rotor (S)
Viscosity (in revolutions per minute) (in mPa s) Inverse latex nd
(T3) Sol. 7 R 6, S 5 79 400 Sol. 8 R 6, S 5 45 200 Sol. 9 R 3, S 5
3300 nd: not determined
3) Measurement of the Inversion Time and Evaluation of the
Stability of the Inverse Latex (T3)
[0209] b)--The inversion time of the inverse latex (T3), evaluated
in the same way as in example 1, is approximately 2 minutes. [0210]
c)--The stability of the inverse latex (T3) is evaluated in the
same way as in example 1. The time for appearance of the nil layer
is two weeks.
Example 3
(According to the Invention): Self-Invertible Inverse Latex of the
AN/AA/(LA-4EO) [AM/AA/(LA-4EO) 24.7/74.1/1.2 Molar] Copolymer
Crosslinked with MBA
1) Preparation
[0211] Stages a) to d) of example T3 are reproduced. In stage f),
2% by weight of Laureth-7 and 4% by weight of the surfactant
composition (C) are added in place of the 4% of Montanox.TM. 20 and
2% of Laureth-7 of said example T3 and the self-invertible inverse
latex (3) is obtained.
2) Viscometry, Measurement of the Inversion Time and Evaluation of
the Stability of the Inverse Latex (3)
[0212] a)--The viscometric performance of the inverse latex (3) is
similar to that reported for the inverse latex of example 13.
[0213] b)--The inversion time of the inverse latex (3), evaluated
in the same way as in example 1, is approximately 30 seconds.
[0214] c)--The stability of the inverse latex (3) evaluated in the
same way as in example 1. The time for appearance of the first oil
drops is three weeks.
Example 4
(According to the Invention): Self-Invertible Inverse Latex of the
ATBS (Na Salt)/AA/HEA/THAM/(LA-4EO) [ATBS/AA/HEA/THAMMA-4EO)
83.9/1.9/9.3/3.7/1.2 Molar] Copolymer Crosslinked with MBA
1) Preparation
[0214] [0215] a)--The following are successively introduced with
stirring into a first beaker: [0216] 672.5 g of a 55% (by weight)
commercial solution of the sodium salt of
2-acrylamido-2-methylpropanesulfonic acid (ATPS Na); [0217] 20.8 q
of 2-hydroxyethyl acrylate; [0218] 12.6 q of THAM; [0219] 2.6 g of
acrylic acid (AA); [0220] 0.041 g of methylenebisacrylamide (MBA);
[0221] 0.45 q of a 40% commercial solution of sodium
diethylenetriaminepentaacetate.
[0222] The pH is then adjusted therein to 4 by adding, if
necessary, the required amount of
2-acrylamido-2-methylpropanesulfonic acid and deionized water up to
700p. [0223] b)--The following are successively introduced with
stirring into a second beaker: [0224] 130 p of polyisobutene,
[0225] 30 g of Marcol.TM. 52, [0226] 90 g of Isopar.TM. H, [0227]
17 g of Montane.TM. 70, [0228] 5 g of Hypermer.TM. 6212, [0229] 3 g
of Dehymuls PGPH (polyglyceryi polyhydroxystearate), [0230] 7.4 g
of tetraethoxylated lauryl acrylate (commercial) (LA-4EO), [0231]
0.14 g of dilauroyi peroxide. [0232] c)--The aqueous phase is then
incorporated in the organic phase with stirring and then the
preemulsion thus obtained is subjected to shearing mechanical
stirring using a rotor agitator of Silverson type so as to create a
fine emulsion while sparging with nitrogen. [0233] d)--After
cooling to approximately 8.degree. C., the polymerization reaction
is initiated using the oxidation/reduction couple: cumene
hydroperoxide/sodium metabisulfite. [0234] e)--Once the
polymerization reaction is complete, the Isopar.TM. H and virtually
all of the water are removed by vacuum distillation. [0235]
f)--After introduction of 2% by weight of Laureth-7 and 4% by
weight of the surfactant composition (C) obtained in example A, the
self-invertible inverse latex (4) is obtained, which latex
comprises approximately 63% of polymer, which is not very viscous,
which inverts very rapidly in water and which has a high thickening
power. Its water content, measured by Karl-Fischer titrimetry, is
2.2% by weight.
2) Viscosity Measurements
[0235] [0236] a)--The viscosity of the self-invertible inverse
latex (4) obtained as indicated in section 1, that of an aqueous
solution devoid of sodium chloride (Sol.10) and that of an aqueous
solution comprising 0.1% by weight (Sol.11) of sodium chloride are
measured, said aqueous solutions each comprising 2% by weight of
said self-invertible inverse latex (4). The results, measured using
a Brookfield RVT viscometer, are recorded in the following
table:
TABLE-US-00004 [0236] Rotor (R); Rotational speed of the rotor (S)
Viscosity (in revolutions per minute) (in mPa s) Inverse latex (4)
R 3, S,20 1100 Sol. 10 R 6, S 5 66 200 Sol. 11 R 6, S 5 16 500 nd:
not determined
3) Measurement of the Inversion Time and Evaluation of the
Stability of the Inverse Latex
[0237] b)--The inversion time of the inverse latex (4), evaluated
in the same way as in example 1, is approximately 30 seconds.
[0238] c)--The stability of the inverse latex (4) evaluated in the
same way as in example 1. The time for appearance of the first
drops is three weeks.
* * * * *