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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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- -1 ether compound Chemical class 0.000 claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 239000004744 fabric Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 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
- 239000011780 sodium chloride Substances 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 229920000742 Cotton Polymers 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000005660 chlorination reaction Methods 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-O dimethylaminium Chemical compound C[NH2+]C ROSDSFDQCJNGOL-UHFFFAOYSA-O 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-N,N-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- 210000004369 Blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-O ethyl(methyl)azanium Chemical compound CC[NH2+]C LIWAQLJGPBVORC-UHFFFAOYSA-O 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-MCPD Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-Methylenebis(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-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
- XHXUANMFYXWVNG-ADEWGFFLSA-N Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 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 Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001808 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
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 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
- 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
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 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
- 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
- 239000004753 textile Substances 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
The cross reference of related application
Subject application requires the preferential of the U.S. Provisional Patent Application case the 61/704,062nd of JIUYUE in 2012 submission on the 21st
Power, described application case is incorporated herein in entirety by reference.
Technical field
Present invention below relates generally to yarn fabric processing method, and more particularly to dye-fixing agent (dye
fixative agent)。
Background technology
It is known that form " cation Cotton Gossypii " to increase by being incorporated in bafta or yarn fabric by positive charge
Dye uptake.One of most popular method is to use ammonium compounds based on epoxide, such as chlorination 3-chlorine-2-hydroxyl propyl group front three
Base ammonium (commercially available with trade mark CR-2000), joins electric charge in the cellulosic polymer main chain of Cotton Gossypii.
But, in art, outstanding demand is to increase relative Dye uptake, produces more in bafta processes
Few refuse and processing cost lower compared with conventional additives is provided.
Summary of the invention
In one embodiment, the present invention includes a kind of 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 C1-C6 alkyl being optionally substituted is independently be when occurring every time；And
X independently be Cl, Br or I when occurring every time.
" dye-fixing agent " means to be incorporated into by positive charge in bafta or yarn fabric to increase Dye uptake (because contaminating
Material particle be anion) reagent.In order to compare, the reaction efficiency of CR-2000 is more than 7% (seeing example 3), and therefore, has
The compound of formula I having the most equal performance is dye-fixing agent.
" optionally it is substituted " and means that described group is unsubstituted or through one or more selected from halogen, hydroxyl, amino or carboxyl
Group, atomic group or part replace." amino " it is intended to the amino being further substituted with through C1-C3 alkyl, preferably front three
Base amino (-N+(CH3)3).When described group replaces through more than one substituent group, described substituent group may be the same or different.One
In individual embodiment, optional substituent group is one or more hydroxyl.
" alkyl " means saturated monovalent straight chain or branched aliphatic hydrocarbyl group.Representative example includes, but is not limited to first
Base, ethyl, propyl group, isopropyl, butyl, isobutyl group, the tert-butyl group, sec-butyl, amyl group, isopentyl, neopentyl, hexyl, isohesyl
Deng.
Salt means to there is relative ion, preferably halogen, more preferably Cl-。
In a preferred embodiment, X is Cl.
In one embodiment, R2And R3It is identical when occurring at least twice.In one embodiment, R2And R3?
Differ when occurring at least twice.In one embodiment, R2And R3It is identical when occurring for all four times.
In one embodiment, the ether compound of Formulas I is symmetrical.In other words, twice R1Appearance is identical, twice
R2Appearance is identical, twice R3Appearance is identical, and twice X occurs it being identical.One of this embodiment non-limiting
Example is the product of double [2-(N, N-dimethylamino) ethyl] ether and chloropropylene oxide:
Chlorination N, N '-(epoxide is double (ethane-2,1-diyl)) double (3-chlorine-2-hydroxyl-N, N-dimethyl propylene-1-amine)
In one embodiment, the ether compound of Formulas I is asymmetric.In other words, below at least one: twice
R1Appearance differs, twice R2Appearance differs, or twice R3Appearance differs.In one embodiment, when
R1When being-CH2CH2-when it occurs for the first time, it is not-CH2CH2-when its second time occurs.The one of this embodiment
Individual limiting examples is that chloropropylene oxide reacts with 3-(2-(dimethylamino) ethyoxyl)-N-N-dimethyl propylene-1-amine, produces chlorine
Change the chloro-N-of 3-(3-(2-((3-chlorine-2-hydroxyl propyl group) Dimethyl Ammonium) ethyoxyl) propyl group)-2-hydroxy-n, N-dimethyl propylene-1-
Amine.
The chloro-N-of chlorination 3-(3-(2-((3-chlorine-2-hydroxyl propyl group) Dimethyl Ammonium) ethyoxyl) propyl group)-2-hydroxy-n, N-
Dimethyl propylene-1-amine
Another limiting examples of this embodiment is chloropropylene oxide and 2, and 2 '-epoxide is double (n-ethyl-N-methyl ethamine)
Reaction, produces N, N '-(epoxide is double (ethane-2,1-diyl)) double (3-chloro-N-ethyl-2-hydroxy-N-methvl acrylate-1-amine)
N, N '-(epoxide is double (ethane-2,1-diyl)) double (3-chloro-N-ethyl-2-hydroxy-N-methvl acrylate-1-amine)
Another limiting examples of this embodiment is chloropropylene oxide and N-(2-(2-(ethyl (methyl) amino) ethyoxyl)
Ethyl) reaction of-N-methyl-prop-1-amine, produce the chloro-N-of chlorination 3-(2-(2-((3-chlorine-2-hydroxyl propyl group) (ethyl) (methyl)
Ammonium) ethyoxyl) ethyl)-2-hydroxy-N-methvl-N-propyl group acrylate-1-amine.
The chloro-N-of chlorination 3-(2-(2-((3-chlorine-2-hydroxyl propyl group) (ethyl) (methyl) ammonium) ethyoxyl) ethyl)-2-hydroxyl
Base-N-Methyl-N-propyl acrylate-1-amine
Another limiting examples of this embodiment is chloropropylene oxide and 1-(2-(dimethylamino) ethyoxyl)-N, N, 2-
Trimethyl acrylate-2-amine reacts, and produces the chloro-N-of chlorination 3-(2-(2-((3-chlorine-2-hydroxyl propyl group) Dimethyl Ammonium)-methyl-prop oxygen
Base) ethyl)-2-hydroxy-n, N-dimethyl propylene-1-amine
The chloro-N-of chlorination 3-(2-(2-((3-chlorine-2-hydroxyl propyl group) Dimethyl Ammonium)-2-methyl-prop epoxide) ethyl)-2-hydroxyl
Base-N, N-dimethyl propylene-1-amine
In use, dye-fixing agent of the present invention is for the method that processes fabric, and described method comprises and applies institute to fabric
State dye-fixing agent.
Detailed description of the invention
Example
Following instance explanation some embodiments of the present invention.
Example 1
Double [2-(N, N-dimethylamino) ethyl] ether reacts with chloropropylene oxide.Diamidogen and distilled water are mixed (10.84g bis-
Amine (0.07 mole)/23.12g water), and with concentrated hydrochloric acid by pH regulator to 8.5.Temperature is adjusted to 25 DEG C, and through 60 minutes time
Between add 99.9% chloropropylene oxide (20.84g (0.22 mole)).Temperature is kept 2 hours at 25 DEG C, after being then increased to 50 DEG C
Continue 2 hours.With concentrated hydrochloric acid pH is reduced to ＜ 2.0, and continues 1 hour after temperature is increased to 70 DEG C.Then reaction is cooled down,
And after falling below 50 DEG C at temperature, use 50%NaOH solution by pH regulator to 4-6.Carry out extracting seven times with dichloromethane
(1 volume: 1 volume), removes residual dichloromethane the most routinely.The active solid of batch 1 is 39.4%.
Product13C NMR confirm to be formed chlorination N, N '-(epoxide double (ethane-2,1-diyl)) double (3-chlorine-2-hydroxyl-N,
N-dimethyl propylene-1-amine), hereafter it is referred to as batch 1.
Example 2
For color analysis, cotton samples compositions (batch 1) and comparative substantially depending on example 1 (is purchased from
The CR-2000 of Dow Chemical (The Dow Chemical Company)) process.
With molar concentration meter, process content roughly the same.Cotton Gossypii use Ahiba IR staining machine and with 50g/L CR-2000
Process each compound reaction comparing substantially equimolar amounts.Relative to quaternary ammonium compound use equimolar amounts sodium hydroxide and
0.24 moles of NaOH of additional catalytic amount/mole Cotton Gossypii (based on 162 grams/mol of monomer mw).Reaction with Cotton Gossypii is with 8: 1 liquid
Ratio is carried out one hour at 70 DEG C.The sample of process is immersed in a beaker of water, beaker 1g/L acetic acid and last beaker
In water, it is dried in 50 DEG C of baking ovens subsequently.The amount of sodium hydroxide used be enough to make the chlorhydrin of existence become epoxide, and makees
For some hydroxyls in the additional quantity activated cellulose of catalyst.
Use(LECO table the 203-821-140th, " in yarn fabric, fabric and Cotton Gossypii for blood urea/nitrogen analyzer and method
Carbon and nitrogen (Carbon, and Nitrogen in Textile, Fabric, and Cotton) ", 08/10 rev 2) analyze
The nitrogen percentage ratio of Cotton Gossypii from the process of each material standed for.Theoretical replacement degree (" Theo DS ") be reagent mole divided by
In Cotton Gossypii anhydroglucose monomeric unit mole.The Theo DS of CR-2000 is 0.226, and the Theo DS of batch 1 is
0.223.Nitrogen percentage ratio (" N% ") passes throughAnalyze sample on blood urea/nitrogen analyzer to measure.The N% of CR-2000 is
0.135, and the N% of batch 1 is 0.242.
The sample processed is then with red 1 dyeing of 1.7g/L acid.The cotton samples processed dyes at Ahiba IR at 80 DEG C
To dye the deceleration time of 4 DEG C/min 20 minutes in machine.The Cotton Gossypii of dyeing tap water rinses three times altogether.Rinse for the first time
At 30 DEG C, continue 10 minutes, at each comfortable 80 DEG C of twice heat flush subsequently, continue 10 minutes.Sample is dried in 50 DEG C of baking ovens
Overnight.The sample of dyeing is analyzed by Hunter Lab MiniScan EZ spectrophotometer (model 4500L) to measure L*, a*
And b*.The colour of each sample is shown in Table 1:
Table 1
| L* | a* | b* | |
| (comparison) CR-2000 processes | 39.58 | 57.89 | 24.25 |
| Batch 1 processes | 34.54 | 53.61 | 28.58 |
Batch 1 has deeper red tone compared with CR-2000, as indicated by lower L* value, L* value instruction color
Brightness (0 be black and 100 be white).
Example 2
Dyestuff reaction efficiency is analyzed, cotton samples compositions-treated described in table 2:
Table 2
The amount of each reagent used in table 2 is adjusted to equal to about 0.045 moles/mole Cotton Gossypii (theoretical DS).Use
Substantially depending on the processing scheme of example 2, including dyestuff.Beat all being that while is compared ether and compares quaternary amine (monoamine or two
Amine) the most equally work, but batch 1 (ethers of two amine of coupling) substantially better works.
" RE " means reaction efficiency and calculates divided by theory replacement degree by reality replaces degree.Actual DS means
Actual replacement degree and be the reagent mole being reacted on Cotton Gossypii mole.Theoretical DS means theoretical replacement degree and is attempt to reaction
Reagent mole on Cotton Gossypii mole.
Claims (8)
1. the method processing fabric, it includes applying dye-fixing agent, the contained I of described dye-fixing agent to described fabric
Ether compound:
Wherein,
R1C1-C6 alkyl is independently be when occurring every time；
R2And R3The C1-C6 alkyl being optionally substituted is independently be when occurring every time；And
X independently be Cl, Br or I when occurring every time.
Method the most according to claim 1, its condition is to work as R1It is-CH when it occurs for the first time2CH2-time, R1Its
It not-CH when secondary occurs2CH2-。
Method the most according to claim 1, wherein R2And R3It is identical when occurring at least twice.
Method the most according to claim 1, wherein R2And R3It is identical when occurring for all four times.
Method the most according to claim 1, wherein R2And R3Differ when occurring at least twice.
Method the most according to claim 1, the ether compound of wherein said Formulas I is symmetrical.
Method the most according to claim 1, the ether compound of wherein said Formulas I is asymmetric.
Method the most according to 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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