CN104685121B - Dye-fixing agent and method - Google Patents
Dye-fixing agent and method Download PDFInfo
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- CN104685121B CN104685121B CN201380048053.4A CN201380048053A CN104685121B CN 104685121 B CN104685121 B CN 104685121B CN 201380048053 A CN201380048053 A CN 201380048053A CN 104685121 B CN104685121 B CN 104685121B
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- 238000000034 method Methods 0.000 title claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 ether compound Chemical class 0.000 claims abstract description 13
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 239000000834 fixative Substances 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- VOSOVMCFUULPKH-UHFFFAOYSA-N 1-chloro-3-(dimethylamino)propan-2-ol Chemical compound CN(C)CC(O)CCl VOSOVMCFUULPKH-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- VJCKDIKJHJHBHY-UHFFFAOYSA-N 1-chloro-3-[ethyl(methyl)amino]propan-2-ol Chemical compound CCN(C)CC(O)CCl VJCKDIKJHJHBHY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- JRLYTGVHVJEPRE-UHFFFAOYSA-N 1-[2-(dimethylamino)ethoxy]-n,n,2-trimethylpropan-2-amine Chemical compound CN(C)CCOCC(C)(C)N(C)C JRLYTGVHVJEPRE-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- 0 CCCC(*)C*(*)(NC(C)(CC)O)N=C Chemical compound CCCC(*)C*(*)(NC(C)(CC)O)N=C 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- WXLFIFHRGFOVCD-UHFFFAOYSA-L azophloxine Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 WXLFIFHRGFOVCD-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- CJIMSAVNVRIJHZ-UHFFFAOYSA-N n-[2-[2-[ethyl(methyl)amino]ethoxy]ethyl]-n-methylpropan-1-amine Chemical compound CCCN(C)CCOCCN(C)CC CJIMSAVNVRIJHZ-UHFFFAOYSA-N 0.000 description 1
- YUZHAOSJYQHGGN-UHFFFAOYSA-N n-ethyl-2-[2-[ethyl(methyl)amino]ethoxy]-n-methylethanamine Chemical compound CCN(C)CCOCCN(C)CC YUZHAOSJYQHGGN-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 description 1
Abstract
What the present invention described is dye-fixing agent, the ether compound of its contained I, including its salt:Wherein, R1C1 C6 alkyl is independently be when occurring every time；R2And R3The C6 alkyl being optionally substituted is independently be when occurring every time；And X independently be Cl, Br or I when occurring every time.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
This application claims priority from U.S. provisional patent application No. 61/704,062, filed on 21/9/2012, which is incorporated herein by reference in its entirety.
Technical Field
The present invention relates generally to textile treatment methods, and more particularly to dye fixative agents (dyefixative agents).
Background
It is well known to form "cationic cotton" by introducing a positive charge into cotton fabric or textile in order to increase dye uptake. One of the most common methods is to use an epoxide-based ammonium compound, such as 3-chloro-2-hydroxypropyltrimethylammonium chloride (commercially available under the trademark CR-2000), to add charge to the cellulosic polymer backbone of cotton.
However, an unmet need in the art is to increase relative dye uptake, generate less waste in cotton fabric processing, and provide lower processing costs compared to conventional additives.
Disclosure of Invention
In one embodiment, the present invention includes a dye fixative agent comprising an ether compound of formula I, including salts thereof:
wherein,
R1independently at each occurrence is a C1-C6 alkyl group;
R2and R3Independently at each occurrence, is an optionally substituted C1-C6 alkyl group; and is
X in each occurrence is independently Cl, Br or I.
By "dye fixative agent" is meant an agent that introduces a positive charge into a cotton fabric or textile so as to increase dye uptake (since the dye particles are anionic). For comparison, the reaction efficiency of CR-2000 is greater than 7% (see example 3), and therefore, compounds of formula I having at least equivalent properties are dye fixatives.
By "optionally substituted" is meant that the group is unsubstituted or substituted with one or more groups, radicals or moieties selected from halogen, hydroxyl, amino or carboxyl. "amino" is intended to include amino further substituted with C1-C3 alkyl, preferably trimethylamino (-N)+(CH3)3). When the group is substituted with more than one substituent, the substituents may be the same or different. In one embodiment, the optional substituents are one or more hydroxyl groups.
"alkyl" means a saturated monovalent straight or branched chain aliphatic hydrocarbon group. Representative examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl and the like.
Salt means the presence of a counter ion, preferably a halogen, more preferably Cl-。
In a preferred embodiment, X is Cl.
In one embodiment, R2And R3Is the same in at least two occurrences. In one embodiment, R2And R3Is not the same in at least two occurrences. In one embodiment, R2And R3The same in all four occurrences.
In one embodiment, the ether compound of formula I is symmetrical. In other words, two times R1Occurrence is identical, two times R2Occurrence is identical, two times R3The occurrences are the same, and the two X occurrences are the same. A non-limiting example of this embodiment is bis [2- (N, N-dimethylamino) ethyl]Reaction product of an ether with epichlorohydrin:
n, N' - (oxybis (ethane-2, 1-diyl)) bis (3-chloro-2-hydroxy-N, N-dimethylpropan-1-amine) chloride
In one embodiment, the ether compound of formula I is asymmetric. In other words, at least one of: two times of R1The occurrence is not the same, two times R2The occurrence is not the same, or two times R3The occurrence is not the same. In one embodiment, when R1When it is-CH 2CH 2-at its first occurrence, it is not-CH 2CH 2-at its second occurrence. One non-limiting example of this embodiment is the reaction of epichlorohydrin with 3- (2- (dimethylamino) ethoxy) -N-N-dimethylpropan-1-amine to produce 3-chloro-N- (3- (2- ((3-chloro-2-hydroxypropyl) dimethylammonium) ethoxy) propyl) -2-hydroxy-N, N-dimethylpropan-1-amine chloride.
3-chloro-N- (3- (2- ((3-chloro-2-hydroxypropyl) dimethylammonium) ethoxy) propyl) -2-hydroxy-N, N-dimethylpropan-1-amine chloride
Another non-limiting example of this embodiment is the reaction of epichlorohydrin with 2, 2 '-oxybis (N-ethyl-N-methylethylamine) to produce N, N' - (oxybis (ethane-2, 1-diyl)) bis (3-chloro-N-ethyl-2-hydroxy-N-methylpropan-1-amine)
N, N' - (oxybis (ethane-2, 1-diyl)) bis (3-chloro-N-ethyl-2-hydroxy-N-methylpropan-1-amine)
Another non-limiting example of this embodiment is the reaction of epichlorohydrin with N- (2- (2- (ethyl (methyl) amino) ethoxy) ethyl) -N-methylpropan-1-amine to produce 3-chloro-N- (2- (2- ((3-chloro-2-hydroxypropyl) (ethyl) (methyl) ammonium) ethoxy) ethyl) -2-hydroxy-N-methyl-N-propylpropan-1-amine chloride.
3-chloro-N- (2- (2- ((3-chloro-2-hydroxypropyl) (ethyl) (methyl) ammonium) ethoxy) ethyl) -2-hydroxy-N-methyl-N-propylpropan-1-amine chloride
Another non-limiting example of this embodiment is the reaction of epichlorohydrin with 1- (2- (dimethylamino) ethoxy) -N, N, 2-trimethylpropan-2-amine to give 3-chloro-N- (2- (2- ((3-chloro-2-hydroxypropyl) dimethylammonium) -methylpropoxy) ethyl) -2-hydroxy-N, N-dimethylpropan-1-amine chloride
3-chloro-N- (2- (2- ((3-chloro-2-hydroxypropyl) dimethylammonium) -2-methylpropoxy) ethyl) -2-hydroxy-N, N-dimethylpropan-1-amine chloride
In use, the dye fixative agents of the present invention are used in a method of treating a fabric, the method comprising applying the dye fixative agents to the fabric.
Detailed Description
Examples of the invention
The following examples illustrate some embodiments of the invention.
Example 1
Bis [2- (N, N-dimethylamino) ethyl ] ether is reacted with epichlorohydrin. The diamine and distilled water were mixed (10.84g diamine (0.07 mole)/23.12 g water) and the pH was adjusted to 8.5 with concentrated HCl. The temperature was adjusted to 25 ℃ and 99.9% epichlorohydrin (20.84g (0.22 mole)) was added over a period of 60 minutes. The temperature was maintained at 25 ℃ for 2 hours, then increased to 50 ℃ for 2 hours. The pH was lowered to < 2.0 with concentrated HCl and the temperature was raised to 70 ℃ for 1 hour. The reaction was then cooled and after the temperature dropped below 50 ℃ the pH was adjusted to 4-6 with 50% NaOH solution. Extraction with dichloromethane was carried out seven times (1 vol: 1 vol) and the residual dichloromethane was then removed conventionally. The active solid of batch 1 was 39.4%.
Of the product13C NMR confirmed the formation of N, N' - (oxybis (ethane-2, 1-diyl)) bis (3-chloro-2-hydroxy-N, N-dimethylpropan-1-amine) chloride, hereinafter referred to as batch 1.
Example 2
For color analysis, cotton samples were treated with a composition substantially in accordance with example 1 (batch 1) and a comparative (CR-2000 available from The Dow Chemical Company).
The treatment contents were approximately the same in terms of molar concentration. Cotton was reacted using an Ahiba IR staining machine and approximately equimolar amounts of each compound compared to the 50g/L CR-2000 treatment. Equimolar amounts of sodium hydroxide and an additional catalytic amount of 0.24 mol NaOH per mole of cotton were used relative to the quaternary ammonium compound (based on 162 g/mol monomer mw). The reaction with cotton was carried out at a liquor ratio of 8: 1 at 70 ℃ for one hour. The treated sample was immersed in a beaker of water, a beaker of 1g/L acetic acid and finally a beaker of water and subsequently dried in an oven at 50 ℃. The amount of sodium hydroxide used is sufficient to cause the chlorohydrin present to become an epoxide, and the additional amount as a catalyst activates some of the hydroxyl groups in the cellulose.
Use ofNitrogen analyzer and method (LECO table # 203-. The theoretical degree of substitution ("Theo DS") is an experimentThe moles of agent divided by the moles of anhydroglucose monomer units in the cotton. Theo DS for CR-2000 was 0.226, and Theo DS for batch 1 was 0.223. Percent nitrogen ("N%") is passed throughThe nitrogen analyzer analyzes the sample to determine. The N% of CR-2000 was 0.135 and the N% of batch 1 was 0.242.
The treated sample was then stained with 1.7g/L acid Red 1. The treated cotton samples were dyed in an Ahiba IR dyeing machine at 80 ℃ for 20 minutes with a deceleration time of 4 ℃/minute. The dyed cotton was rinsed with tap water a total of three times. The first rinse was continued at 30 ℃ for 10 minutes, followed by two hot rinses each at 80 ℃ for 10 minutes. The samples were dried in an oven at 50 ℃ overnight. The stained samples were analyzed by Hunter Lab MiniScan EZ spectrophotometer (model 4500L) to determine L, a, and b. The color values for each sample are shown in table 1:
TABLE 1
| L* | a* | b* | |
| (comparative) CR-2000 treatment | 39.58 | 57.89 | 24.25 |
| Batch 1 processed | 34.54 | 53.61 | 28.58 |
Batch 1 had a darker red hue as compared to CR-2000, as indicated by a lower value of L, indicating the brightness of the color (0 is black and 100 is white).
Example 2
For dye reaction efficiency analysis, cotton samples were treated with the compositions described in table 2:
TABLE 2
The amount of each reagent used in table 2 was adjusted to equal about 0.045 moles/mole cotton (theoretical DS). A treatment protocol substantially in accordance with example 2 was used, including a dye. It was surprising that while the comparative ether and comparative quaternary amine (mono-or diamine) worked reasonably equally, batch 1 (ether coupling two amines) worked significantly better.
"RE" means the efficiency of the reaction and is calculated by dividing the actual degree of substitution by the theoretical degree of substitution. The actual DS means the actual degree of substitution and is the moles of reagent reacted onto the moles of cotton. Theoretical DS means the theoretical degree of substitution and is the moles of reagent that are intended to react to moles of cotton.
Claims (8)
1. A method of treating a fabric comprising applying to the fabric a dye fixative comprising an ether compound of formula I:
wherein,
R1independently at each occurrence is a C1-C6 alkyl group;
R2and R3Independently at each occurrence is optionalA substituted C1-C6 alkyl group; and is
X in each occurrence is independently Cl, Br or I.
2. The method of claim 1, provided that when R is1is-CH at its first occurrence2CH2When is, R1Is not-CH at its second occurrence2CH2-。
3. The method of claim 1, wherein R2And R3Is the same in at least two occurrences.
4. The method of claim 1, wherein R2And R3The same in all four occurrences.
5. The method of claim 1, wherein R2And R3Is not the same in at least two occurrences.
6. The process of claim 1 wherein the ether compound of formula I is symmetrical.
7. The process of claim 1 wherein the ether compound of formula I is asymmetric.
8. The method of claim 1, wherein X is Cl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610985555.5A CN106498780B (en) | 2012-09-21 | 2013-09-18 | A kind of textile fabric |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261704062P | 2012-09-21 | 2012-09-21 | |
| US61/704062 | 2012-09-21 | ||
| PCT/US2013/060275 WO2014047099A1 (en) | 2012-09-21 | 2013-09-18 | Dye fixative agents and methods |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610985555.5A Division CN106498780B (en) | 2012-09-21 | 2013-09-18 | A kind of textile fabric |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104685121A CN104685121A (en) | 2015-06-03 |
| CN104685121B true CN104685121B (en) | 2016-11-30 |
Family
ID=
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB514861A (en) * | 1938-05-17 | 1939-11-20 | Reginald John William Reynolds | Textile treatment agents |
| US4506081A (en) * | 1982-09-02 | 1985-03-19 | Buckman Laboratories, Inc. | Polymeric quaternary ammonium compounds and their uses |
| US4778813A (en) * | 1981-07-07 | 1988-10-18 | Buckman Laboratories International, Inc. | Polymeric quaternary ammonium compounds, their preparation and use |
| CN102573773A (en) * | 2008-02-04 | 2012-07-11 | 莱雅公司 | Cationic surfactant compounds, use thereof as conditioner, cosmetic treatment method, and cosmetic or pharmaceutical compositions comprising same |
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB514861A (en) * | 1938-05-17 | 1939-11-20 | Reginald John William Reynolds | Textile treatment agents |
| US4778813A (en) * | 1981-07-07 | 1988-10-18 | Buckman Laboratories International, Inc. | Polymeric quaternary ammonium compounds, their preparation and use |
| US4506081A (en) * | 1982-09-02 | 1985-03-19 | Buckman Laboratories, Inc. | Polymeric quaternary ammonium compounds and their uses |
| CN102573773A (en) * | 2008-02-04 | 2012-07-11 | 莱雅公司 | Cationic surfactant compounds, use thereof as conditioner, cosmetic treatment method, and cosmetic or pharmaceutical compositions comprising same |
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