U.S. patent application number 11/263391 was filed with the patent office on 2006-05-04 for processes for modifying textiles using ionic liquids.
Invention is credited to Stacie Ellen Hecht, Gregory Scot Miracle, Kenneth Nathan Price, Jeffrey John Scheibel, Jiping Wang, Nodie Monroe Washington.
Application Number | 20060090271 11/263391 |
Document ID | / |
Family ID | 35892286 |
Filed Date | 2006-05-04 |
United States Patent
Application |
20060090271 |
Kind Code |
A1 |
Price; Kenneth Nathan ; et
al. |
May 4, 2006 |
Processes for modifying textiles using ionic liquids
Abstract
Processes for modifying a textile to improve its performance
which comprise the steps of a) contacting a textile comprising
fibers with a treating composition comprising an ionic liquid under
conditions sufficient to modify at least surfaces of the fibers,
thereby provide a performance improvement to treated textile; b)
optionally, contacting a textile comprising fibers with a
composition comprising a benefit agent; and c) at least partially
removing the treating composition from the textile. In specific
embodiments, the surface modification comprises a partial
dissolution of at least one outer layer of the fibers and/or
crystal structure change in at least surfaces of the fibers. The
surface modification can impart improvements to the textile or
allow embedding or attachment of a benefit agent in the fibers.
Inventors: |
Price; Kenneth Nathan;
(Wyoming, OH) ; Wang; Jiping; (West Chester,
OH) ; Washington; Nodie Monroe; (Wilberforce, OH)
; Hecht; Stacie Ellen; (West Chester, OH) ;
Miracle; Gregory Scot; (Hamilton, OH) ; Scheibel;
Jeffrey John; (Loveland, OH) |
Correspondence
Address: |
THE PROCTER & GAMBLE COMPANY;INTELLECTUAL PROPERTY DIVISION
WINTON HILL TECHNICAL CENTER - BOX 161
6110 CENTER HILL AVENUE
CINCINNATI
OH
45224
US
|
Family ID: |
35892286 |
Appl. No.: |
11/263391 |
Filed: |
October 31, 2005 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
60624053 |
Nov 1, 2004 |
|
|
|
Current U.S.
Class: |
8/490 |
Current CPC
Class: |
D06M 2200/45 20130101;
D06M 13/00 20130101; D06M 23/10 20130101; D06P 1/928 20130101; D06M
2200/20 20130101; D06P 1/445 20130101; D06M 2200/50 20130101 |
Class at
Publication: |
008/490 |
International
Class: |
D06P 5/00 20060101
D06P005/00 |
Claims
1. A process for modifying a textile to improve performance of the
textile, the process comprising: a) contacting a textile comprising
fibers with a treating composition comprising an ionic liquid under
conditions sufficient to modify at least a portion of the surface
of the fibers; b) optionally, contacting the textile with a
composition comprising a benefit agent; and c) at least partially
removing the treating composition from the textile.
2. The process of claim 1, wherein the surface modification
comprises a partial dissolution of at least one outer layer of the
fibers.
3. The process of claim 1, wherein the surface modification results
in crystal structure change in at least the surfaces of the
fibers.
4. The process of claim 1, wherein the treated textile exhibits
improved property selected from the group consisting of: wrinkle
resistance, smoothness, softness, shape retention, and combinations
thereof.
5. The process of claim 1, wherein the surface modification enables
embedding and/or attachment of at least one benefit agent in the
surfaces of the fibers.
6. The process of claim 1, wherein the benefit agent is selected
from the group consisting of perfumes, dyes, dye fixative agents,
sizings, skin conditioning actives, vitamins, enzymes, surfactants,
anti-abrasion agents, wrinkle resistant agents, stain resistant
agents, water resistant agents, flame retardants, antimicrobial
agents, metal bleach catalysts, bleaching agents, fabric softeners,
anti-pilling agents, water repellant agents, ultraviolet protection
agents, brighteners, and mixtures thereof.
7. The process of claim 1, wherein the benefit agent is adapted for
controlled release from the surface of the fiber.
8. The process of claim 1, wherein the treating composition
comprises at least about 50% by weight of the composition of the
ionic liquid.
9. The process of claim 1, wherein the contacting step is conducted
during an additional treatment selected from the group consisting
of sizing, desizing, bleaching, scouring, mercerization, dyeing,
printing, finishing, coating, and combinations thereof.
10. The process of claim 1, wherein the ionic liquid includes an
anionic component comprising one or more anions selected from the
group consisting of alkyl sulfates, alkoxy sulfates, alkyl alkoxy
sulfates, monoesters of sulfosuccinates, diesters of
sulfosuccinates, methyl ester sulfonates, alkylaryl sulfonates,
alkyl glycerol ether sulfonates, diphenyl ethers, linear
carboxylates, cyclic carboxylates, alkyl oxyalkylene carboxylates,
monosulfonates of diphenyl oxides, mid-chain branched alkyl
sulfates, mid-chain branched alkylaryl sulfonates, mid-chain
branched alkyl polyoxyalkylene sulfates, alpha-olefin sulfonates,
paraffin sulfonates, alkyl phosphate esters, sarcosinates,
taurates, sulfated oils and fatty acids, sulfonated oils and fatty
acids, alkyl phenol ethoxy sulfates, alkyl phenol ethoxy
sulfonates, fatty acid ester sulfonates, substituted
salicylanilides, substituted phenol anions, substituted thiophenol
anions, polyamino polycarboxylates, aminopolyphosphates,
sweetener-derived anions, ethoxylated amide sulfates, sodium
tripolyphosphate; dihydrogen phosphate; fluroalkyl sulfonate;
bis-(alkylsulfonyl) amine; bis-(fluoroalkylsulfonyl)amide;
(fluroalkylsulfonyl) (fluoroalkylcarbonyl)amide;
bis(arylsulfonyl)amide; carbonate; tetrafluorborate
(BF.sub.4.sup.-); hexaflurophosphate (PF.sub.6.sup.-); and anionic
bleach activators having the general formula:
R.sub.1-CO--O--C.sub.6H.sub.4-R.sub.2, wherein R.sub.1 is C8-C18
alkyl, C8-C18 amino alkyl, or mixtures thereof, and R.sub.2 is
sulfonate or carbonate, and mixturees thereof.
11. The process of claim 1, wherein the ionic liquid includes a
cationic component comprising one or more cations selected from the
group consisting of amine oxide cations, phosphine oxide cations,
sulfoxide cations, betaines, diester quaternary ammonium (DEQA)
cations, alkylene quaternary ammonium cations, difatty amido
quaternary ammonium cations, C.sub.8-22 quaternary surfactants,
cationic esters, 4,5-dichloro-2-n-octyl-3-isothiazolone, quaternary
amino polyoxyalkylenes, alkyl oxyalkylene cations, alkoxylate
quaternary ammoniums, substituted and unsubstituted pyrrolidinium,
imidazolium, benzimidazolium, pyrazolium, benzpyrazolium,
thiazolium, benzthiazolium, oxazolium, benzoxazolium, isoxazolium,
isothiazolium, imdazolidenium, guanidinium, indazolium,
quinuclidinium, triazolium, isoquinuclidinium, piperidinium,
morpholinium, pyridazinium, pyrazinium, triazinium, azepinium,
diazepinium, pyridinium, piperidonium, pyrimidinium, thiophenium;
and phosphonium, cationic bleach activators having a quaternary
ammonium moiety, cationic anti-microbial agents, alkylated caffeine
cations, alkyl poly amino carboxylates, and mixtures thereof.
12. The process of claim 1, wherein the textile comprises loose
fibers, a yarn, a woven textile, a nonwoven textile, a knitted
textile, or a fabric article.
13. The process of claim 1, wherein the contacting step is
performed by a non-immersive method selected from the group
consisting of spraying, misting, foaming, and combinations
thereof.
14. The process of claim 13, wherein the composition is in the form
of droplets.
15. The process of claim 1, wherein the composition is removed from
the textile by rinsing with water, pressing, squeezing, padding,
centrifugation, vacuum extraction, or combinations thereof.
16. The process of claim 1 further comprising the step of
collecting the composition removed from the textile.
17. The process of claim 1, wherein energy is applied to the
composition prior to or during the contacting step.
18. The process of claim 17, wherein energy is selected from heat,
microwave, infrared, ultrasonic, and combinations thereof.
19. The process of claim 1, wherein pressure is applied during the
contacting step.
Description
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority under 35 U.S.C.
.sctn.119(e) from Provisional Application Serial No. 60/624,053,
filed on Nov. 1, 2004.
FIELD OF THE INVENTION
[0002] The present invention is directed to processes for modifying
textiles which comprise fibers. More particularly, the invention is
directed to such processes which employ ionic liquid-containing
compositions.
BACKGROUND OF THE INVENTION
[0003] In recent years, ionic liquids have been extensively
evaluated as environmental-friendly or "green" alternatives to
conventional organic solvents for a broad range of organic
synthetic applications. Ionic liquids offer some unique
characteristics that distinguish them from conventional organic
solvents, such as no effective vapor pressure, a broad liquid
range, high polarity and charge density, can be either hydrophobic
or hydrophilic, and unique solvating properties.
[0004] One widely studied class of ionic liquids includes
imidazolinium salts, such as butylmethylimidazolinium
hexafluorophosphate, also known as BMIM/PF6. Other well known ionic
liquids include N-1-ethyl 3-methylimidazolinum chloride aluminum
(III) chloride, which is usually referred to as [emim]Cl-AlCl3; and
N-butyl pyridinium chloride aluminum (III) chloride, which is
usually referred to as [Nbupy]Cl-AlCl3. A broad range of ionic
liquids have also been investigated in the following references: WO
03/029329; WO 03/074494; WO 03/022812; WO 2004/016570; US
2004/0035293A1; and U.S. Pat. No. 5,827,602.
[0005] In addition to chemical processes, ionic liquids have also
been used as microbiocides/plant growth regulators, as described in
FR 2434156; as antistatic agents, as described in JP10-265674 and
U.S. Pat. No. 3,282,728; and as fruit and vegetable produce
treating agents, as described in WO 01/19200. Other uses of ionic
liquids are disclosed in U.S. Pat. No. 6,048,388 as a component of
an ink composition; and in J. Am. Chem. Soc., Vol. 124, pp.
4974-4975 (2002), as an agent to dissolve cellulose.
[0006] Published PCT Application WO 2004/003120 discloses ionic
liquid based products suitable for use in surface or air treating
compositions, and ionic liquid cocktails containing three or more
different and charged ionic liquid components. The products are
particularly useful in various consumer product applications, such
as home care, air care, surface cleaning, laundry and fabric care
applications.
[0007] Owing to various unique properties of ionic liquids, it
would be advantageous to employ such materials in additional
applications.
[0008] Accordingly, it is desirable to employ ionic
liquid-containing compositions in textile treating processes.
Particularly, the treating process provides improvements to
textiles which comprise fibers, and to provide such improvements
through the use of ionic liquid-containing compositions. These
processes are advantageous in that they allow provision of improved
properties to textiles while employing materials recognized as
environmentally friendly.
SUMMARY OF THE INVENTION
[0009] The present invention is directed to processes for modifying
a textile to improve its performance which comprise the steps of a)
contacting a textile comprising fibers with a treating composition
comprising an ionic liquid under conditions sufficient to modify at
least a portion of the surface of the fibers, thereby providing a
performance improvement to treated textile; b) optionally,
contacting a textile comprising fibers with a composition
comprising a benefit agent; and c) at least partially removing the
treating composition from the textile. In specific embodiments, the
surface modification comprises a partial dissolution of at least
one outer layer of the fibers and/or crystal structure change in at
least surfaces of the fibers. The surface modification can impart
improvements to the textile or allow embedding or attachment of a
benefit agent in the fibers.
[0010] Additional embodiments and advantages of the processes are
described in further detail in the following detailed
description.
DETAILED DESCRIPTION OF THE INVENTION
[0011] The processes according to the present invention for
modifying a textile which comprises fibers include the steps of a)
contacting the textile with a composition comprising an ionic
liquid under conditions sufficient to modify at least surfaces of
the fibers and provide, or facilitate provision of, a performance
improvement thereto; and b) at least partially removing the
composition from the textile. Within the present context, a textile
which comprises fibers refers to any fiber-containing textile
material or product and includes, but is not limited to, loose or
free fibers, yarns (including threads), woven textiles, nonwoven
textiles, knitted textiles, fabric articles, and the like. Fabric
articles include, but are not limited to, garments, components used
in the manufacture of garments, carpets, upholstery, and the like.
Additionally, the textile fibers may be formed of any natural
(e.g., cellulose), regenerated (e.g., rayon), or synthetic
material, or a combination thereof. In one embodiment, the textile
fibers comprise a cellulosic material. In another embodiment, the
fibers comprise a synthetic material, for example comprising
polyester.
[0012] In some embodiments, the ionic liquid as used herein refers
to a salt that has a melting temperature of about 100.degree. C. or
less, or, in an alternative embodiment, has a melting temperature
of about 60.degree. C. or less, or, in yet another alternative
embodiment, has a melting temperature of about 40.degree. C. or
less. In other embodiments, the ionic liquids exhibit no
discernible melting point (based on DSC analysis) but are
"flowable" at a temperature of about 100.degree. C. or below, or,
in another embodiment, are "flowable" at a temperature of from
about 20 to about 80.degree. C. i.e., the typical fabric or dish
washing temperatures. As used herein, the term "flowable" means
that the ionic liquid exhibits a viscosity of less than about
10,000 mPas at the temperatures as specified above.
[0013] It should be understood that the terms "ionic liquid",
"ionic compound", and "IL" refer to ionic liquids, ionic liquid
composites, and mixtures (or cocktails) of ionic liquids. The ionic
liquid can comprise an anionic IL component and a cationic IL
component. When the ionic liquid is in its liquid form, these
components may freely associate with one another (i.e., in a
scramble). As used herein, the term "cocktail of ionic liquids"
refers to a mixture of two or more, preferably at least three,
different and charged IL components, wherein at least one IL
component is cationic and at least one IL component is anionic.
Thus, the pairing of three cationic and anionic IL components in a
cocktail would result in at least two different ionic liquids. The
cocktails of ionic liquids may be prepared either by mixing
individual ionic liquids having different IL components, or by
preparing them via combinatorial chemistry. Such combinations and
their preparation are discussed in further detail in US
2004/0077519A1 and US 2004/0097755A1. As used herein, the term
"ionic liquid composite" refers to a mixture of a salt (which can
be solid at room temperature) with a proton donor Z (which can be a
liquid or a solid) as described in the references immediately
above. Upon mixing, these components turn into a liquid at about
100.degree. C. or less, and the mixture behaves like an ionic
liquid.
[0014] Some of the properties that ionic liquids possess and make
them attractive alternatives to conventional solvents include: a)
ionic liquids have a broad liquid range; some ionic liquids can be
in the liquid form at a temperature as low as -96.degree. C. and
others can be thermally stable at temperatures up to 200.degree.
C.; this permits effective kinetic control in many organic
reactions and processes; b) ionic liquids have no effective vapor
pressure, thus, they are easy to handle and they reduce safety
concerns where volatility could be an issue; c) ionic liquids are
effective solvents for a broad range of organic and inorganic
materials due to their high polarity; d) ionic liquids are
effective Bronsted/Lewis acids; and e) ionic liquids can be tuned
to the specific application/chemistry desired, for example, they
can be selectively made to have properties ranging from hydrophilic
to hydrophobic. By virtue of their high polarity and charge
density, ionic liquids have unique solvating properties, and may be
used in a variety of processing environments and conditions.
[0015] Nonlimiting examples of anions and cations suitable for use
in the ionic liquids for the present invention are discussed in
details below.
Anions
[0016] Anions suitable for use in the ionic liquids of the present
invention include, but are not limited to, the following materials:
[0017] (1) Alkyl sulfates (AS), alkoxy sulfates and alkyl alkoxy
sulfates, wherein the alkyl or alkoxy is linear, branched or
mixtures thereof; furthermore, the attachment of the sulfate group
to the alkyl chain can be terminal on the alkyl chain (AS),
internal on the alkyl chain (SAS) or mixtures thereof: non-limiting
examples include linear C.sub.10-C.sub.20 alkyl sulfates having
formula: CH.sub.3(CH.sub.2).sub.x+yCH.sub.2OSO.sub.3.sup.-M.sup.+
wherein x+y is an integer of at least 8, preferably at least about
10; M.sup.+ is a cation selected from the cations of the ionic
liquids as described in detail herein; or linear C.sub.10-C.sub.20
secondary alkyl sulfates having formula: ##STR1## wherein x+y is an
integer of at least 7, preferably at least about 9; x or y can be
0, M.sup.+ is a cation selected from the cations of the ionic
liquids as described in detail herein; or C10-C20 secondary alkyl
ethoxy sulfates having formula: ##STR2## wherein x+y is an integer
of at least 7, preferably at least about 9; x or y can be 0,
M.sup.+ is a cation selected from the cations of the ionic liquids
as described in detail herein; non-limiting examples of alkoxy
sulfate include sulfated derivatives of commercially available
alkoxy copolymers, such as Pluronics.RTM. (from BASF); [0018] (2)
Mono- and di-esters of sulfosuccinates: non-limiting examples
include saturated and unsaturated C.sub.12-18 monoester
sulfosuccinates, such as lauryl sulfosuccinate available as
Mackanate LO-100.RTM. (from The McIntyre Group); saturated and
unsaturated C.sub.6-C.sub.12 diester sulfosuccinates, such as
dioctyl ester sulfosuccinate available as Aerosol OT.RTM. (from
Cytec Industries, Inc.); [0019] (3) Methyl ester sulfonates (MES);
[0020] (4) Alkyl aryl sulfonates, non-limiting examples include
tosylate, alkyl aryl sulfonates having linear or branched,
saturated or unsaturated C.sub.8-C.sub.14 alkyls; alkyl benzene
sulfonates (LAS) such as C.sub.11-C.sub.18 alkyl benzene
sulfonates; sulfonates of benzene, cumene, toluene, xylene, t-butyl
benzene, di-isopropyl benzene, or isopropyl benzene; naphthalene
sulfonates and C.sub.6-14 alkyl naphthalene sulfonates, such as
Petro.RTM. (from Akzo Nobel Surface Chemistry); sulfonates of
petroleum, such as Monalube 605.RTM. (from Uniqema); [0021] (5)
Alkyl glycerol ether sulfonates having 8 to 22 carbon atoms in the
alkyl moiety; [0022] (6) Diphenyl ether (bis-phenyl) derivatives:
Non-limiting examples include Triclosan
(2,4,4'-trichloro-2'-hydroxydiphenyl ether) and Diclosan
(4,4'-dichloro-2-hydroxydiphenyl ether), both are available as
Irgasan.RTM. from Ciba Specialty Chemicals; [0023] (7) Linear or
cyclic carboxylates: non-limiting examples include citrate,
lactate, tartarate, succinate, alkylene succinate, maleate,
gluconate, formate, cinnamate, benzoate, acetate, salicylate,
phthalate, aspartate, adipate, acetyl salicylate, 3-methyl
salicylate, 4-hydroxy isophthalate, dihydroxyfumarate,
1,2,4-benzene tricarboxylate, pentanoate and mixtures thereof;
[0024] (8) Alkyl oxyalkylene carboxylates: non-limiting examples
include C.sub.10-C.sub.18 alkyl alkoxy carboxylates preferably
comprising 1-5 ethoxy units; [0025] (9) Alkyl diphenyl oxide
monosulfonate: non-limiting examples include alkyl diphenyl oxide
monosulfonate of the general formula: ##STR3## wherein R.sup.1 is
C.sub.10-C.sub.18 linear or branched alkyl; R.sup.2 and R.sup.3 are
independently SO.sub.3.sup.- or H, provided at least one of R.sup.2
or R.sup.3 is not hydrogen; R.sup.4 is R.sup.1 or H; suitable alkyl
diphenyl oxide monosulfonates are available as DOWFAX.RTM. from Dow
Chemical and as POLY-TERGENT.RTM. from Olin Corp.; [0026] (10)
Mid-chain branched alkyl sulfates (HSAS), mid-chain branched alkyl
aryl sulfonates (MLAS) and mid-chain branched alkyl polyoxyalkylene
sulfates; non-limiting examples of MLAS are disclosed in U.S. Pat.
No. 6,596,680; U.S. Pat. No. 6,593,285; and U.S. Pat. No.
6,202,303; [0027] (11) Alpha olefin sulfonates (AOS) and paraffin
sulfonates, non-limiting examples include C.sub.10-22 alpha-olefin
sulfonates, available as Bio Terge AS-40.RTM. from Stepan Company;
[0028] (12) Alkyl phosphate esters, non-limiting examples include
C.sub.8-22 alkyl phosphates, available as Emphos CS.RTM. and Emphos
TS-230.RTM. from Akzo Nobel Surface Chemistry LLC; [0029] (13)
Sarcosinates having the general formula
RCON(CH.sub.3)CH.sub.2CO.sub.2.sup.-, wherein R is an alkyl from
about C.sub.8-20; non-limiting examples include ammonium lauroyl
sarcosinate, available as Hamposyl AL-30.RTM. from Dow Chemicals
and sodium oleoyl sarcosinate, available as Hamposyl O.RTM. from
Dow Chemical; [0030] (14) Taurates, such as C.sub.8-22 alkyl
taurates, available as sodium coco methyl tauride or Geropon
TC.RTM. from Rhodia, Inc.; [0031] (15) Sulfated and sulfonated oils
and fatty acids, linear or branched, such as those sulfates or
sulfonates derived from potassium coconut oil soap available as
Norfox 1101.RTM. from Norman, Fox & Co. and Potassium oleate
from Chemron Corp.; [0032] (16) Alkyl phenol ethoxy sulfates and
sulfonates, such as C.sub.8-14 alkyl phenol ethoxy sulfates and
sulfonates; non-limiting examples include sulfated nonylphenol
ethoxylate available as Triton XN-45S.RTM. from Dow Chemical;
[0033] (17) Fatty acid ester sulfonates having the formula:
R.sup.1-CH(SO.sub.3.sup.-)CO.sub.2R.sup.2 wherein R.sup.1 is linear
or branched C.sub.8 to C.sub.18 alkyl, and R.sup.2 is linear or
branched C.sub.1 to C.sub.6 alkyl; [0034] (18) Substituted
salicylanilide anions having the formula (I): ##STR4## wherein m is
an integer from 0 to 4; n is an integer from 0 to 5; the sum of m+n
is greater than zero; a is 0 or 1; b is 0 or 1; g is 0 or 1; when b
is 0, one of a and g must be 0; Z and Z' are independently selected
from O and S; X and X', when present, are selected from O, S, and
NR.sup.1, where R.sup.1 is independently selected from the group
consisting of H, C.sub.1-C.sub.16 linear or branched, substituted
or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,
alkaryl, aralkyl, and aryl; T, when present, is selected from
C.dbd.O, C.dbd.S, S.dbd.O, and SO.sub.2; when T is S.dbd.O or
S.sub.2, X and X' may not be S; when either a, b or g is 1 for a
radical R-(X).sub.a-(T).sub.b-(X').sub.g-, R for that radical is
independently selected from the group consisting of H,
C.sub.1-C.sub.16 linear or branched, substituted or unsubstituted
alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl,
aralkyl, and aryl; when a, b and g are all 0 for a radical, R for
that radical may be further selected from the group consisting of
F, Cl, Br, I, CN, R.sub.2N.fwdarw.O, NO.sub.2; when all a, b and g
are 0, at least one R must be non-H; further provided that the
total number of halogen atoms in the molecule excluding any present
in R does not exceed two; R.sup.2 is independently selected from
the group consisting of C.sub.1-C.sub.16 linear or branched,
substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl,
cycloalkenyl, alkaryl, aralkyl, and aryl, and mixtures thereof;
derivatized substituted salicylanilide anions, wherein one or both
aromatic rings comprise additional substituents, are also suitable
for use herein; substituted salicylanilide and derivatives thereof
are disclosed in US 2002/0068014A1 and WO 04/026821; M.sup.+ is a
cation selected from the cations of the ionic liquids as disclosed
herein; [0035] (19) Substituted phenol or thiophenol anions having
the formula (II): ##STR5## wherein m is an integer from 0 to 4; a
is 0 or 1; b is 0 or 1; g is 0 or 1; when b is 0, one of a and g
must be 0; Z is selected from O and S; X and X', when present, are
selected from O, S, and NR.sup.1; when either a, b or g is 1 for a
radical R-(X).sub.a-(T).sub.b-(X').sub.g-, R for that radical is
independently selected from the group consisting of H,
C.sub.1-C.sub.16 linear or branched, substituted or unsubstituted
alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl,
aralkyl, and aryl; when a, b and g are all 0 for a radical, R for
that radical may be further selected from the group consisting of
F, Cl, Br, I, CN, R.sub.2N.fwdarw.O, NO.sub.2; T, when present, is
selected from C.dbd.O, C.dbd.S, S.dbd.O, and SO.sub.2; when T is
S.dbd.O or SO.sub.2, X and X' may not be S; Y is a radical
comprising at least 1 but no more than 20 carbon atoms and
containing a substituent -X''-H, where X'' is selected from O, S,
and N-(T').sub.b'-(X''').sub.a'-R.sup.2, where a' is 0 or 1, b' is
0 or 1, and X''', when present, is selected from O, S, and
NR.sup.2; R.sup.2 is independently selected from the group
consisting of H, C.sub.1-C.sub.16 linear or branched, substituted
or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,
alkaryl, aralkyl, and aryl; T', when present, is selected from
C.dbd.O, C.dbd.S, and SO.sub.2; when T' is SO.sub.2, X''' may not
be S; R.sup.3 is independently selected from the group consisting
of C.sub.1-C.sub.16 linear or branched, substituted or
unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl,
alkaryl, aralkyl, and aryl, and mixtures thereof. The substituted
phenol or thiophenol anions are disclosed in US 2002/0068014A1 and
WO 04/026821; M.sup.+ is a cation selected from the cations of the
ionic liquids as disclosed herein; [0036] (20) Polyamino
polycarboxylates: non-limiting examples include ethylene
ethylene-diamine tetraacetate (EDTA), diamine tetracetates,
N-hydroxy ethyl ethylene diamine triacetates, nitrilo-tri-acetates,
ethylenediamine tetraproprionates, triethylene tetraamine
hexacetates, diethylene triamine pentaacetates, and ethanol
diglycines; [0037] (21) Aminopolyphosphonates: such as
ethylenediamine tetramethylene phosphonate and diethylene triamine
pentamethylene-phosphonate; [0038] (22) Sweetener derived anions:
saccharinate and acesulfamate; ##STR6## wherein M+ is a cation
selected from the cations of the ionic liquids as described herein;
[0039] (23) Ethoxylated amide sulfates; sodium tripolyphosphate
(STPP); dihydrogen phosphate; fluroalkyl sulfonate;
bis-(alkylsulfonyl) amine; bis-(fluoroalkylsulfonyl)amide;
(fluroalkylsulfonyl)(fluoroalkylcarbonyl)amide;
bis(arylsulfonyl)amide; carbonate; tetrafluorborate
(BF.sub.4.sup.-); hexaflurophosphate (PF.sub.6.sup.-); [0040] (24)
Anionic bleach activators having the general formula:
R.sup.1-CO--O--C.sub.6H.sub.4-R.sup.2 wherein R.sup.1 is
C.sub.8-C.sub.18 alkyl, C.sub.8-C.sub.18 amino alkyl, or mixtures
thereof, and R.sup.2 is sulfonate or carbonate; non-limiting
examples such as: ##STR7##
[0041] 4-[N-(nonanoyl)aminohexanoyloxy]hexanoyloxybenzenesulfonate
are disclosed in U.S. Pat. No. 5,891,838; U.S. Pat. No. 6,448,430;
U.S. Pat. No. 5,891,838; U.S. Pat. No. 6,159,919; U.S. Pat. No.
6,448,430; U.S. Pat. No. 5,843,879; U.S. Pat. No. 6,548,467.
Cations
[0042] Cations suitable for use in the ionic liquids of the present
invention include, but are not limited to, the following materials:
[0043] (a) Cations (i.e., in the protonated, cationic form) of
amine oxides, phosphine oxides, or sulfoxides: non-limiting
examples include amine oxide cations containing one C.sub.8-18
alkyl moiety and 2 moieties selected from the group consisting of
C.sub.1-3 alkyl groups and C.sub.1-3 hydroxyalkyl groups; phosphine
oxide cations containing one C.sub.10-18 alkyl moiety and 2
moieties selected from the group consisting of C.sub.1-3 alkyl
groups and C.sub.1-3 hydroxyalkyl groups; and sulfoxide cations
containing one C.sub.10-18 alkyl moiety and a moiety selected from
the group consisting of C.sub.1-3 alkyl and C.sub.1-3 hydroxyalkyl
moieties; in some embodiments, the amine oxide cations have the
following formula: ##STR8## wherein R.sup.3 is an C.sub.8-22 alkyl,
C.sub.8-22 hydroxyalkyl, C.sub.8-22 alkyl phenyl group, and
mixtures thereof; R.sup.4 is an C.sub.2-3 alkylene or C.sub.2-3
hydroxyalkylene group or mixtures thereof; x is from 0 to about 3;
and each R.sup.5 is independently an C.sub.1-3 alkyl or C.sub.1-3
hydroxyalkyl group or a polyethylene oxide group containing an
average of from about 1 to about 3 ethylene oxide groups; the
R.sup.5 groups may be attached to each other, e.g., through an
oxygen or nitrogen atom, to form a ring structure; other exemplary
amine oxide cations include C.sub.10-C.sub.18, C.sub.10,
C.sub.10-C.sub.12, and C.sub.12-C.sub.14 alkyl dimethyl amine oxide
cations, and C.sub.8-C.sub.12 alkoxy ethyl dihydroxy ethyl amine
oxide cations; [0044] (b) Betaines having the general formula:
R-N.sup.(+)(R.sup.1).sub.2-R.sup.2COOH wherein R is selected from
the group consisting of alkyl groups containing from about 10 to
about 22 carbon atoms, preferably from about 12 to about 18 carbon
atoms, alkyl aryl and aryl alkyl groups containing a similar number
of carbon atoms with a benzene ring treated as equivalent to about
2 carbon atoms, and similar structures interrupted by amido or
ether linkages; each R.sup.1 is an alkyl group containing from 1 to
about 3 carbon atoms; and R.sup.2 is an alkylene group containing
from 1 to about 6 carbon atoms; non-limiting examples of betaines
include dodecyl dimethyl betaine, acetyl dimethyl betaine, dodecyl
amidopropyl dimethyl betaine, tetradecyl dimethyl betaine,
tetradecyl amidopropyl dimethyl betaine, dodecyl dimethyl ammonium
hexanoate; and amidoalkylbetaines which are disclosed in U.S. Pat.
Nos. 3,950,417; 4,137,191; and 4,375,421; and British Patent GB No.
2,103,236; in another embodiment, the cation may be a sulfobetaine,
which are disclosed in U.S. Pat. No. 4,687,602; [0045] (c)
Amphodiacetates, such as disodium cocodiacetate, available as
Mackam 2C.RTM. from McIntyre; [0046] (d) Diester quaternary
ammonium (DEQA) cations of the type:
R.sub.(4-m)-N.sup.+-[(CH.sub.2).sub.n-Y-R.sup.1].sub.m wherein each
R substituent is selected from hydrogen; C.sub.1-C.sub.6 alkyl or
hydroxyalkyl, preferably methyl, ethyl, propyl, or hydroxyethyl,
and more preferably methyl; poly(C.sub.1-C.sub.3 alkoxy),
preferably polyethoxy; benzyl; or a mixture thereof; m is 2 or 3;
each n is from 1 to about 4; each Y is --O--(O)C--, --C(O)--O--,
--NR--C(O)--, or --C(O)--NR--; with the proviso that when Y is
--O--(O)C-- or --NR--C(O)--, the sum of carbons in each R.sup.1
plus one is C.sub.12-C.sub.22, preferably C.sub.14-C.sub.20, with
each R.sup.1 being a hydrocarbyl, or substituted hydrocarbyl group;
in one embodiment, the DEQA cation is an alkyl dimethyl
hydroxyethyl quaternary ammonium as discussed in U.S. Pat. No.
6,004,922; in another embodiment, the DEQA cation has the general
formula: R.sub.3N.sup.+CH.sub.2CH(YR.sup.1)(CH.sub.2YR.sup.1)
wherein each Y, R, R.sup.1 have the same meanings as before; in yet
another embodiment, the DEQA cation is [CH.sub.3].sub.3
N.sup.(+)[CH.sub.2CH(CH.sub.2O(O)CR.sup.1)O(O)CR.sup.1] wherein
each R.sup.1 is in the range of C.sub.15 to C.sub.19; [0047] (e)
Alkylene quaternary ammonium cations having the formula:
R.sub.(4-m)-N.sup.+-R.sup.1.sub.m wherein each m is 2 or 3; each R
is independently an alkyl or hydroxyalkyl C.sub.1-C.sub.6 moiety,
preferably methyl, ethyl, propyl or hydroxyethyl, and more
preferably methyl; each R.sup.1 is independently a linear or
branched, saturated or unsaturated C.sub.6-C.sub.22 alkyl or alkoxy
moiety, preferably C.sub.14-C.sub.20 moiety, but no more than one
R.sup.1 being less than about C.sub.12 and then the other R.sup.1
is at least about C.sub.16; or hydrocarbyl or substituted
hydrocarbyl moiety, preferably C.sub.10-C.sub.20 alkyl or alkenyl,
most preferably C.sub.12-C.sub.18 alkyl or alkenyl; in one
embodiment, the cation is dialkylenedimethyl ammonium, such as
dioleyldimethyl ammonium available from Witco Corporation under the
tradename Adogen.RTM. 472; in another embodiment, the cation
monoalkenyltrimethyl ammonium, such as monooleyltrimethyl ammonium,
monocanolatrimethyl ammonium, and soyatrimethyl ammonium; [0048]
(f) Difatty amido quaternary ammonium cations such as:
[R.sup.1-C(O)-NR-R.sup.2-N(R).sub.2-R.sup.3-NR-C(O)-R.sup.1].sup.+
wherein R and R.sup.1 are as defined in cation (e) above, R.sup.2
and R.sup.3 are C.sub.1-C.sub.6 alkylene moieties; for example,
difatty amido quats are commercially available from Witco under the
Varisoft.RTM. tradename; [0049] (g) C.sub.8-22 quaternary
surfactants such as isostearyl ethyl imidonium available in its
ethosulfate salt form as Schercoquat IIS.RTM. from Scher Chemicals,
Inc., quaternium-52 obtainable as Dehyquart SP.RTM. from Cognis
Corporation, and dicoco dimethyl ammonium available in its chloride
salt form as Arquad 2C-75.RTM. from Akzo Nobel Surface Chemistry
LLC; [0050] (h) Cationic esters such as discussed in U.S. Pat. No.
4,228,042, U.S. Pat. No. 4,239,660, U.S. Pat. No. 4,260,529 and
U.S. Pat. No. 6,022,844; [0051] (i)
4,5-dichloro-2-n-octyl-3-isothiazolone, which is obtainable as
Kathon.RTM. from Rohm and Haas; [0052] (j) Quaternary amino
polyoxyalkylene derivatives (choline and choline derivatives);
[0053] (k) Alkyl oxyalkylene cations; [0054] (l) Alkoxylate
quaternary ammoniums (AQA) as discussed in U.S. Pat. No. 6,136,769;
[0055] (m) Substituted and unsubstituted pyrrolidinium,
imidazolium, benzimidazolium, pyrazolium, benzpyrazolium,
thiazolium, benzthiazolium, oxazolium, benzoxazolium, isoxazolium,
isothiazolium, imdazolidenium, Guanidinium, indazolium,
quinuclidinium, triazolium, isoquinuclidinium, piperidinium,
morpholinium, pyridazinium, pyrazinium, triazinium, azepinium,
diazepinium, pyridinium, piperidonium, pyrimidinium, thiophenium;
phosphonium; in one embodiment, the cation is an substituted
imidazolium cation having the formula: ##STR9## wherein each R and
R.sup.1 are as defined in cation (e) above; each R.sup.2 is a
C.sub.1-C.sub.6 alkylene group, preferably an ethylene group; and G
is an oxygen atom or an -NR- group; for example, the cation
1-methyl-1-oleylamidoethyl-2-oleylimidazolinium is available
commercially from the Witco Corporation under the trade name
Varisoft.RTM. 3690; in another embodiment, the cation is
alkylpyridinium cation having the formula: ##STR10##
[0056] wherein R.sup.1 is an acyclic aliphatic C.sub.8-C.sub.22
hydrocarbon group; in another embodiment, the cation is an
alkanamide alkylene pyridinium cation having the formula: ##STR11##
wherein R.sup.1 is a linear or branched, saturated or unsaturated
C.sub.6-C.sub.22 alkyl or alkoxy moiety, or a hydrocarbyl or
substituted hydrocarbyl moiety, and R.sup.2 is a C.sub.1-C.sub.6
alkylene moiety; [0057] (n) Cationic bleach activators having a
quaternary ammonium moiety including but not limited to ##STR12##
these and other cationic bleach activators suitable for use herein
as cations of the ionic liquids are disclosed in U.S. Pat. No.
5,599,781, U.S. Pat. No. 5,686,015, U.S. Pat. No. 5,686,015, WO
95/29160, U.S. Pat. No. 5,599,781, U.S. Pat. No. 5,534,179, EP 1
253 190 A1, U.S. Pat. No. 6,183,665, U.S. Pat. No. 5,106,528, U.S.
Pat. No. 5,281,361, and Bulletin de la Societe Chimique de France
(1973), (3)(Pt. 2), 1021-7; [0058] (o) Cationic anti-microbial
agents, such as cetyl pyridinium, chlorohexidine and domiphen.
[0059] (p) Alkylated caffeine cations, such as ##STR13## wherein
R.sub.1 and R.sub.2 are C1 to C12 alkyl or alkylene groups. [0060]
(q) Alkyl poly amino carboxylates, such as ##STR14## wherein R is
C.sub.8 to C.sub.22 alkyl or alkylene groups or is coco, tallow or
oleyl; non-limiting examples include Ampholak.RTM. 7CX/C,
Ampholak.RTM. 7TX/C, and Ampholak.RTM. XO7/C from Akzo Nobel.
[0061] Thus, the ionic liquids suitable for use herein may have
various anionic and cationic combinations. The ionic species can be
adjusted and mixed such that properties of the ionic liquids can be
customized for specific applications, so as to provide the desired
solvating properties, viscosity, melting point, and other
properties, as desired. These customized ionic liquids have been
referred to as "designer solvents".
[0062] The ionic liquids can be present in various compositions
suitable for use in the processes disclosed herein in any desired
effective amount. Typically, the ionic liquids are present in an
amount ranging from about 0.1% to about 100%, preferably from about
1% to about 85%, and more preferably from about 5% to about 75%, by
weight of the textile treating composition. In some embodiments,
the ionic liquids comprise at least about 50% by weight of the
textile treating composition. In further embodiments, the ionic
liquids comprise at least about 80% by weight of the textile
treating composition, and in yet further embodiments, the ionic
liquids comprise at least about 90% by weight of the textile
treating composition.
[0063] Many ionic liquids are hygroscopic, thus, may contain
appreciable amounts of water (referred to herein as the "innate" or
"bound" water) ranging from about 0.01% to less than about 50% by
weight of the ionic liquid. It should be noted that "free water"
may be added in making the treating composition of the present
invention. A person of ordinary skill in the art would recognize
that once the components (e.g., innate water and free water) are
mixed in a composition, the components can no longer be
distinguished by their origin and will be reported in totality as
percentage of the overall composition. Thus, the textile treating
compositions of the present invention may comprise water,
regardless of its origin, ranging from about 0.01% to about 50%,
preferably from about 1% to about 40%, more preferably from about
5% to about 30% by weight of the composition. The treating
compositions may optionally include a co-solvent. Typical examples
of co-solvents include, but are not limited to, linear or branched
C1-C10 alcohols, diols, and mixtures thereof. In specific
embodiments, co-solvents such as ethanol, isopropanol, propylene
glycol are used in some of the compositions of the present
invention. In additional specific embodiments, the ionic liquid
textile treating composition is substantially free of free water
and/or other organic solvents. These compositions will contain less
than about 10 weight percent, more specifically less than about 5
weight percent, even more specifically less than about 1 weight
percent, free water and/or other organic solvents.
[0064] In some embodiments, the textile treating compositions
containing ionic liquids or cocktails of ionic liquids (undiluted
with adjuncts, co-solvents or free water) employed herein have
viscosities of less than about 2000 mPas, preferably less than
about 750 mPas, as measured at 20.degree. C. In other embodiments,
the viscosity of undiluted ionic liquids are in the range from
about 0.1 to about 500 mPas, preferably from about 0.5 to about 400
mPas, and more preferably from about 1 to about 300 mPas at
20.degree. C. In still another embodiment, the viscosity of textile
treating composition containing ILs lowers to less than about 2000
mPas, preferably less than about 500 mPas, and more preferably less
than about 300 mPas, when heated to a temperature in the range of
about 40.degree. C. to 60.degree. C.
[0065] The viscosities of the ionic fluids and compositions
containing them can be measured on a Brookfield viscometer model
number LVDVII+ at 20.degree. C., with spindle no. S31 at the
appropriate speed to measure materials of different viscosities.
Typically, the measurement is done at a speed of 12 rpm to measure
products of viscosity greater than about 1000 mPas; 30 rpm to
measure products with viscosities between about 500 mPas to about
1000 mPas; and 60 rpm to measure products with viscosities less
than about 500 mPas. The undiluted state is prepared by storing the
ionic liquids or cocktails in a desiccator containing a desiccant
(e.g. calcium chloride) at room temperature for at least about 48
hours prior to the viscosity measurement. This equilibration period
unifies the amount of innate water in the undiluted samples.
[0066] According to the present processes, the textile comprising
fibers is contacted with the composition containing an ionic liquid
(which, as noted above, may comprise a mixture or cocktail of ionic
liquids) under conditions sufficient to modify surfaces of the
fibers and provide, or facilitate provision of, a performance
improvement thereto. A performance improvement is any physical
property which is improved by the ionic liquid treatment. In one
embodiment wherein the textile fibers are in contact with the ionic
liquid-containing composition for a sufficient time such that the
polarity and/or ionic charges, attributable to presence of IL, may
interrupt hydrogen bondings between fibers, thereby crystal
structure changes in at least the surfaces of the fibers may
result. In another embodiment, the textile fibers are contacted by
the ionic liquid-containing composition for a sufficient time such
that partial dissolution of at least one outer layer of the
surfaces of the fibers may result.
[0067] Dissolution of the surface layer(s) and/or changes in
crystal structure can provide various improvements in physical
properties of the fibers, including, but not limited to,
improvements in one or more of the textile's wrinkle resistance,
smoothness, softness, shape retention properties, and the like.
[0068] Further, modifications obtained according to the present
processes, including, but not limited to, partial dissolution of at
least one outer layer of the fibers and/or changes in crystal
structure, can enable embedding and/or attachment of at least one
benefit agent in the surfaces of the fibers, for example, by
further contacting the textile with a composition comprising a
benefit agent, either simultaneously with or subsequent to the
contact with the ionic liquid-containing composition.
Alternatively, the benefit agent may be present, either as an
adjunct or as an ionic liquid active, in the IL-containing
composition.
[0069] In one embodiment, the embedded or attached benefit agent is
released from the fibers in a controlled manner (e.g., a slow and
sustained release over time). In another embodiment, the benefit
agent can be protected or stabilized by the ionic liquids such that
the benefit agent is delivered in a controlled manner (e.g., by
triggering factors, such as copious amount of water, pH change,
heat).
[0070] Suitable benefit agents include, but are not limited to,
perfumes, dyes, dye fixative agents, sizings, skin conditioning
actives, vitamins, enzymes, surfactants, anti-abrasion agents,
wrinkle resistant agents, stain resistant agents, water resistant
agents, flame retardants, antimicrobial agents, metal bleach
catalysts, bleaching agents, fabric softeners, anti-pilling agents,
water repellant agents, ultraviolet protection agents, brighteners,
mixtures thereof (i.e., of two or more of these types of benefit
agents). Additional examples of suitable benefit agents are
disclosed in U.S. Pat. No. 6,488,943, Beerse et al.; U.S. Pat. No.
6,548,470, Buzzaccarini et al.; U.S. Pat. No. 6,482,793, Gordon et
al.; U.S. Pat. No. 6,573,234, Sivik et al.; U.S. Pat. No.
6,525,012, Price et al.; U.S. Pat. No. 6,566,323, Littig et al.;
U.S. Pat. No. 6,090,767, Jackson et al.; U.S. Pat. No. 6,420, 326,
Sherry et al.; U.S. Pat. No. 6,733,538, Panandiker et al.; U.S.
Patent Publication No. 2003/0166495A1, Wang at al.; and U.S. Patent
Publication No. 2004/0121929A1, Wang at al.
[0071] The benefit agents may be included in a textile treating
composition in any desired amount. Typical textile treating
compositions may contain from about 0.001 to about 20 percent by
weight of the benefit agent(s). In more specific embodiments, such
compositions may comprise from about 0.01 to about 10 percent by
weight, and more specifically, from about 0.1 to about 5 percent by
weight, of the benefit agent(s). One skilled in the art will
recognize in view of the foregoing therefore that the modification
may be conducted to any desired depth in the textile fibers and is
not limited to surface modifications.
[0072] The processes according to the invention may be conducted in
any one or combination of continuous, semi-continuous or batch
processing techniques. The contacting step may be achieved in a
manner known in the art, for example, including, but not limited
to, by immersion techniques, or by non-immersion techniques such as
spraying, misting, foaming, padding, or the like. In one
embodiment, the composition is provided in the form of droplets and
the textile fibers are contacted using a non-immersion
technique.
[0073] Additionally, the process may be conducted during textile
mill manufacture or processing, for example in a separate treatment
step or during a conventional processing step, for example during a
treatment such as sizing, desizing, bleaching, scouring,
mercerization, dyeing, printing, finishing, coating, combinations
thereof, or the like. Exemplary textile mill processes which may be
employed are disclosed, for example, in U.S. Patent Application
Publication No. US 2003/0226213; and in "Textile Processing and
Properties: Preparation, Dyeing, Finishing and Performance", by
Vigo, Elsevier, 1994. Alternatively, the process may be conducted
by a consumer on a garment, for example during home laundering or
drying, or other in-home textile/garment treating processes. The
specific physical conditions under which the contacting is
conducted may be varied based on the particular textile fiber to be
treated, the treating composition used and the desired physical
property improvement thereof.
[0074] In one embodiment, energy may be applied to the textile
fibers, either prior to, simultaneous with and/or subsequent to the
contact with the ionic liquid-containing composition, in order to
facilitate achievement and/or durability of the desired
improvement. Energy may be applied in the form of heat and/or
radiation, including, but not limited to microwave, infrared,
ultrasonic, or combinations thereof, and the like. Additionally,
the contacting step may be conducted under increased pressure, at
ambient pressure, or under a reduced pressure vacuum.
[0075] The time which will be sufficient to obtain modification
according to the invention will be dependent on process specifics.
In one embodiment, the contact time is at least about one minute.
In an alternate embodiment, the contact time is at least about five
minutes. After the contacting step has been conducted for a time
sufficient to modify surfaces of the fibers and provide or
facilitate provision of a performance improvement thereto, the
composition is at least partially removed from the textile. In one
embodiment, the composition is substantially fully removed, whereby
the textile comprises less than about 5 weight percent, more
specifically less than about 1 weight percent, and more
specifically less than about 0.1 weight percent of the ionic liquid
after the removal step. The composition may be removed from the
textile by any technique known in the art, including, but not
limited to, rinsing with water, pressing, squeezing, padding,
centrifugation, vacuum extraction, combinations thereof, and the
like. In one embodiment, the composition is collected after it is
removed from the textile, for example for recycle and reuse in the
process.
[0076] All documents cited in the Detailed Description of the
Invention are, in relevant part, incorporated herein by reference;
the citation of any document is not to be construed as an admission
that it is prior art with respect to the present invention.
[0077] While particular embodiments of the present invention have
been illustrated and described, it would be obvious to those
skilled in the art that various other changes and modifications can
be made without departing from the spirit and scope of the
invention. It is therefore intended to cover in the appended claims
all such changes and modifications that are within the scope of
this invention.
* * * * *