U.S. patent application number 10/876037 was filed with the patent office on 2005-02-03 for pearlescent preparations containing quaternized triethanolamine fatty acid esters, processes for preparing the same, and methods of use therefor.
Invention is credited to Bigorra Llosas, Joaquim, Bonastre Gilabert, Nuria, Sanchez, Agustin.
Application Number | 20050022312 10/876037 |
Document ID | / |
Family ID | 33395853 |
Filed Date | 2005-02-03 |
United States Patent
Application |
20050022312 |
Kind Code |
A1 |
Bigorra Llosas, Joaquim ; et
al. |
February 3, 2005 |
Pearlescent preparations containing quaternized triethanolamine
fatty acid esters, processes for preparing the same, and methods of
use therefor
Abstract
The invention relates to pearlescent water-containing
preparations which can be obtained by (a) reacting triethanolamine
and C.sub.12-22 fatty acids in a molar ratio of 1:1.3 to 1:1.4, (b)
subsequently quaternizing the esterification products in known
manner and (c) dispersing the quaternization products in water.
Inventors: |
Bigorra Llosas, Joaquim;
(Sabadell, ES) ; Bonastre Gilabert, Nuria;
(Barbera del Vall, ES) ; Sanchez, Agustin; (Santa
Coloma De Gramenet, ES) |
Correspondence
Address: |
COGNIS CORPORATION
PATENT DEPARTMENT
300 BROOKSIDE AVENUE
AMBLER
PA
19002
US
|
Family ID: |
33395853 |
Appl. No.: |
10/876037 |
Filed: |
June 24, 2004 |
Current U.S.
Class: |
8/115.51 |
Current CPC
Class: |
C11D 3/0089 20130101;
C11D 1/62 20130101; D06M 13/203 20130101; D06M 13/46 20130101; D06M
13/184 20130101; A61K 2800/436 20130101; D06M 13/325 20130101 |
Class at
Publication: |
008/115.51 |
International
Class: |
D06M 010/00 |
Foreign Application Data
Date |
Code |
Application Number |
Jun 24, 2003 |
EP |
03014144.4 |
Claims
What is claimed is:
1. A pearlescent preparation prepared by a process comprising: (a)
reacting triethanolamine and a C.sub.12-22 fatty acid in a molar
ratio of from 1:1.3 to 1:1.4 to form an esterification product; (b)
quaternizing the esterification product; and (c) dispersing the
quaternized esterification product in water.
2. The pearlescent preparation according to claim 1, wherein the
preparation comprises an amount of free C.sub.12-22 fatty acid of
from 1 to 20% by weight based on the dry weight of the
esterification product.
3. The pearlescent preparation according to claim 1, wherein the
triethanolamine and the C.sub.12-22 fatty acid are reacted in a
molar ratio of from 1:1.32 to 1:1.38.
4. The pearlescent preparation according to claim 1, wherein the
C.sub.12-22 fatty acid comprises a fatty acid corresponding to the
general formula I: R.sup.1COOH (I) wherein R.sup.1CO represents a
linear or branched, saturated or unsaturated acyl group having from
16 to 18 carbon atoms.
5. The pearlescent preparation according to claim 3, wherein the
C.sub.12-22 fatty acid comprises a fatty acid corresponding to the
general formula I: R.sup.1COOH (I) wherein R.sup.1CO represents a
linear or branched, saturated or unsaturated acyl group having from
16 to 18 carbon atoms.
6. The pearlescent preparation according to claim 2, wherein the
triethanolamine and the C.sub.12-22 fatty acid are reacted in a
molar ratio of from 1:1.32 to 1:1.38.
7. The pearlescent preparation according to claim 2, wherein the
C.sub.12-22 fatty acid comprises a fatty acid corresponding to the
general formula I: R.sup.1COOH (I) wherein R.sup.1CO represents a
linear or branched, saturated or unsaturated acyl group having from
16 to 18 carbon atoms.
8. The pearlescent preparation according to claim 6, wherein the
C.sub.12-22 fatty acid comprises a fatty acid corresponding to the
general formula I: R.sup.1COOH (I) wherein R.sup.1CO represents a
linear or branched, saturated or unsaturated acyl group having from
16 to 18 carbon atoms.
9. A process for preparing pearlescent preparations, said process
comprising: (a) reacting triethanolamine and a C.sub.12-22 fatty
acid in a molar ratio of from 1:1.3 to 1:1.4 to form an
esterification product; (b) quaternizing the esterification
product; and (c) dispersing the quaternized esterification product
in water.
10. The process according to claim 9, wherein the triethanolamine
and the C.sub.12-22 fatty acid are reacted in a molar ratio of from
1:1.32 to 1:1.38.
11. The process according to claim 9, wherein the C.sub.12-22 fatty
acid comprises a fatty acid corresponding to the general formula I:
R.sup.1COOH (I) wherein R.sup.1CO represents a linear or branched,
saturated or unsaturated acyl group having from 16 to 18 carbon
atoms.
12. The process according to claim 10, wherein the C.sub.12-22
fatty acid comprises a fatty acid corresponding to the general
formula I: R.sup.1COOH (I) wherein R.sup.1CO represents a linear or
branched, saturated or unsaturated acyl group having from 16 to 18
carbon atoms.
13. The process according to claim 9, wherein the C.sub.12-22 fatty
acid comprises a component selected from the group consisting of
hydrogenated or partly hydrogenated coconut oil fatty acids,
hydrogenated or partly hydrogenated tallow fatty acids, palmitic
acid, stearic acid and mixtures thereof.
14. The process according to claim 10, wherein the C.sub.12-22
fatty acid comprises a component selected from the group consisting
of hydrogenated or partly hydrogenated coconut oil fatty acids,
hydrogenated or partly hydrogenated tallow fatty acids, palmitic
acid, stearic acid and mixtures thereof.
15. The process according to claim 9, wherein the esterification
product is quaternized with a reagent selected from the group
consisting of alkyl halides and dialkyl sulfates.
16. The process according to claim 9, wherein the quaternization is
carried out in the presence of an alcohol selected from the group
consisting of lower aliphatic alcohols and polyols.
17. The process according to claim 9, wherein the quaternization is
carried out in the presence of an alcohol selected from the group
consisting of isopropyl alcohol and propylene glycol.
18. A method of softening a fiber, said method comprising: (a)
providing a fiber to be softened; (b) providing a pearlescent
preparation prepared by a process comprising: (i) reacting
triethanolamine and a C.sub.12-22 fatty acid in a molar ratio of
from 1:1.3 to 1:1.4 to form an esterification product; (ii)
quaternizing the esterification product; and (iii) dispersing the
quaternized esterification product in water; and (c) contacting the
fiber with the pearlescent preparation.
Description
BACKGROUND OF THE INVENTION
[0001] Quaternized fatty acid triethanolamine ester salts, which
belong to the group of esterquats, are cationic surfactants which
are readily taken up by synthetic and natural fibers and which
provide them with substantivity and a pleasant soft feel.
Accordingly, aqueous dispersions of these compounds are used as
fabric softeners and as hair conditioners. They are generally
produced from fatty acids which are partly esterified with
triethanolamine in the presence of hypophosphorous acid and then
quaternized with alkyl halides or dialkyl sulfates, preferably
methyl chloride or dimethyl sulfate, in a solution of lower
alcohols or polyols. A molar ratio of triethanolamine to fatty acid
of 1:1.2 to 1:2.2 is generally described in the literature, a ratio
of 1:1.5 to 1:1.9 being preferred for performance reasons.
[0002] From the aesthetic perspective, the market is interested not
only in offering transparent formulations of these esterquats, but
also--and in particular--in providing pearlescent compositions. To
this end, there has been no shortage of attempts to add
corresponding wax components to the dispersions, but to no real
avail, because the waxes cannot be stably incorporated in the
formulation for long periods.
[0003] Accordingly, the problem addressed by the present invention
was to provide new water-containing preparations based on
quaternized fatty acid triethanolamine ester salts which would have
pearlescent properties without the addition of waxes and which
would match known products in their performance properties.
SUMMARY OF THE INVENTION
[0004] The present invention relates to pearlescent
water-containing preparations which can be obtained by: (a)
reacting triethanolamine and C.sub.12-22 fatty acids in a molar
ratio of 1:1.3 to 1:1.4, (b) subsequently quaternizing the
esterification products in known manner and (c) dispersing the
quaternization products in water.
[0005] It has surprisingly been found that esterquats which have
pearlescent properties in the form of aqueous dispersions can be
produced by controlling the degree of esterification and the fatty
acid, so that there is no need to use typical pearlizing waxes, for
example of the glycol fatty acid ester type. The invention includes
the observation that the molar ratio between triethanolamine and
the fatty acids selected is the critical parameter: too low a ratio
would lead to low pearlescence and, in particular, to
unsatisfactory performance properties whereas, if the ratio is too
high, no pearlescent effect at all is observed.
[0006] The present invention also relates to a process for the
production of pearlescent water-containing preparations, in which
(a) triethanolamine and C.sub.12-22 fatty acids are reacted in a
molar ratio of 1:1.3 to 1:1.4, (b) the esterification products are
then quaternized in known manner and (c) the quaternization
products are dispersed in water.
[0007] As a consequence of the substoichiometric use of the fatty
acids, based on the dry residue, the preparations preferably
contain 1 to 20% by weight, preferably 3 to 15% by weight and more
particularly 5 to 10% by weight of free C.sub.12-22 fatty
acids.
DEATILED DESCRIPTION OF THE INVENTION
[0008] Starting Materials
[0009] So far as the alkanolamine component is concerned, the
choice of starting materials is limited to triethanolamine because
the results obtained with methyl diethanolamine, for example, are
far less satisfactory. So far as the choice of the fatty acid
component is concerned, preference attaches to fatty acids
corresponding to formula (I): 1
[0010] in which R.sup.1CO is a linear or branched, saturated or
unsaturated acyl group containing 16 to 18 carbon atoms. The use of
hydrogenated or partly hydrogenated coconut oil or tallow fatty
acid and preferably palmitic, stearic and behenic acid and mixtures
thereof has proved to be particularly effective.
[0011] Esterification and Guatemization
[0012] The esterquats may be produced both from fatty acids and
from the corresponding triglycerides. The condensation of the
alkanolamines with the fatty acids may also be carried out in the
presence of defined quantities of dicarboxylic acids such as, for
example, oxalic acid, malonic acid, succinic acid, maleic acid,
fumaric acid, glutaric acid, adipic acid, sorbic acid, pimelic
acid, azelaic acid, sebacic acid and/or dodecanedioic acid. This
results in a partly oligomeric structure of the esterquats. To
achieve a particular balance between pearlescence and performance,
particularly softness, it has proved to be optimal to use
triethanolamine and fatty acids in a molar ratio of 1:1.32 to
1:1.38. Alkyl halides or dialkyl sulfates, more particularly methyl
chloride or dimethyl sulfate, are suitable for the quaternization.
Both the esterification and the quaternization may be carried out
in known manner. Representatives of the many prior-art publications
include DE 4308794 C1 and DE 4335782 C1 (Cognis) of which the
teaching is encompassed by the present patent application. More
particularly, the quaternized fatty acid triethanolamine ester
salts according to the invention are produced in the presence of
lower aliphatic alcohols or polyols which are added to the
intermediate products before the quaternization. C.sub.1-4 alcohols
and C.sub.2-10 alkylene glycols, especially isopropyl alcohol or
propylene glycol, are suitable for this purpose. Their production
is described, for example, in DE 19738645 C1 (Cognis). The
quaternization generally gives 60 to 95% by weight and preferably
75 to 85% by weight preparations of the quaternized fatty acid
triethanolamine ester salts in the lower alcohols or polyols which
are then diluted with water to a solids concentration of 5 to 40%
by weight and preferably 10 to 30% by weight and show pearlescence
even in this concentration range.
[0013] Commercial Applications
[0014] The present invention also relates to the use of the new
pearlescent water-containing preparations for the production of
softeners for synthetic and/or natural fibers in which they may be
present in quantities of 10 to 100% by weight, based on the final
preparation. In the simplest case, the preparations themselves may
be used as softeners, although they may also be further diluted
with water and/or other typical auxiliaries and additives may be
incorporated. This is particularly the case when the preparations
are to be used as hair conditioners. So far as the additives in
question are concerned, reference is again made to the above-cited
DE 19738645 C1.
EXAMPLES
[0015] 596 to 943 g (2.88 to 4.56 mol) stearic acid (StA) and 1.2
to 1.8 g hypophosphoric acid (50% by weight) were introduced into a
1.5-liter three-necked flask equipped with a stirrer, dropping
funnel and distillation head and heated to 70.degree. C. 363 g (2.4
mol) triethanolamine (TEA) were added dropwise in portions under a
reduced pressure of 30 mbar, the temperature being increased to
160.degree. C. After the addition, the reaction mixture was stirred
for another 2 h at 2 mbar until no more water of reaction was
separated and the acid value had reached a value below 5 mg KOH/g.
400 g (0.86 mol) of the ester produced were then transferred to a
second three-necked flask and dissolved in 126 g propylene glycol
at 50.degree. C. 104 g (0.83 mol) dimethyl sulfate were then added
dropwise in portions and the mixture was stirred for 4 h at
65.degree. C. A solution containing 80% by weight esterquat and 20%
by weight propylene glycol, which was low in viscosity at
20.degree. C., was obtained. Water was then added to the solution
in such a quantity that a dispersion with a solids content of 15%
by weight was obtained.
[0016] The pearlescent properties of the formulations were
subjectively evaluated on a scale of 1 (=sparkling pearlescence) to
4 (=no effect present). To determine performance, 1 kg terry
towelling was washed at 60.degree. C. in a standard domestic
washing machine of the Miele type and a measuring capful of the
softener dispersions was added to the liquor. After drying,
softness was determined by a panel of 5 experienced testers on a
scale of 1 (=very soft) to 4 (=hard) and then averaged. The results
are set out in Table 1. Examples 1 to 3 correspond to the
invention, Examples C1 to C3 are intended for comparison.
1TABLE 1 Pearlesence and softness TEA:CFA Example TEA (g) StA (g)
molar ratio Pearlescence Softness C1 363 596 1:1.20 2 4 1 363 645
1:1.30 1 3 2 363 671 1:1.35 1 2 3 363 695 1:1.40 1 2 C2 363 745
1:1.50 3 2 C3 363 795 1:1.60 4 1 C4 363 943 1:1.90 4 1
[0017] It can be seen that, although acceptable pearlescence is
still obtained where the molar ratio is below the range according
to the invention of 1:1.3 (TEA:CFA), softness is non-existent
whereas, above the limit of 1:1.4 according to the invention,
pearlescence is non-existent but the performance properties are
very good.
[0018] It will be appreciated by those skilled in the art that
changes could be made to the embodiments described above without
departing from the broad inventive concept thereof. It is
understood, therefore, that this invention is not limited to the
particular embodiments disclosed, but it is intended to cover
modifications within the spirit and scope of the present invention
as defined by the appended claims.
* * * * *