US4900544A
Expired / Lapsed
US
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Cationic polymers as antistatic additives for hair preparations
Assignee: Henkel AG and Co KGaA
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Filing: 1986-07-08
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Granted: 1990-02-13
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Expires: 2006-07-08
Abstract
Abstract An aqueous hair-treatment preparation containing an antistatic additive imparting an antistatic effect to the hair, characterized in that said antistatic additive is at least one cationic polymer produced by the process of (1) epoxidizing 1,3-diene homopolymers or copolymers (2) reacting the epoxide compound so produced with low molecular weight amines selected from the group consisting of primary amines, secondary amines and tertiary amines, and (3) converting the reaction products into the salt form or into polymeric quaternary ammonium salts. The use of these polymeric amine salts or quaternary ammonium salts in cosmetic hair-treatment preparations provides these preparations with antistatic effects. Preferred cationic polymers are obtained by the epoxidation of polybutadiene, of which more than 50% of the monomer units show the 1,4-cis-configuration, reaction with dimethylamine or morpholine and conversion into the hydrochlorides or alkylation with glycidyl trimethylammonium chloride, 3-chloro-2-hydroxypropyl trimethylammonium chloride or ethylene oxide. The cationic polymers are preferably used in shampoos in quantities of from 0.5 to 5.0% by weight in addition to 5 to 30% by weight of alkylether sulfate tensides and 1 to 5% by weight of a zwitterionic or amphoteric washing-active substance.
Inventors
- 👤 Wolfgang Ritter
- 👤 Rolf Tenhaef
- 👤 Horst Hoffkes
- 👤 Kurt Seidel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:20
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/72; A61K8/84; A61Q; A61Q5/00; A61Q5/02; C; C08; C08C; C08C19/00; C08C19/30; C08C19/34; C08C19/40; C08G; C08G59/00; C08G59/02; C08G59/027; C08G73/00; C08G73/02; C08G73/0273; A61Q5/10
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
253 words
An aqueous shampoo composition for human hair consisting essentially of: (A) anionic surfactant present in an anionic surfactant effective amount; (B) amphoteric or zwitterionic surfactant present in an amphoteric or zwitterionic surfactant effective amount; and (C) cationic antistatic agent present in an antistatic effective amount, which agent is a cationic polymer that is the reaction product from: (1) a 1,3-diene homopolymer or predominantly 1,3-diene copolymer, having at least 10 1,3-diene units per molecule, in which at least 10% of the double bonds present have been epoxidized and which contains about 3-6% by weight of epoxide oxygen and which has been aminated with (2) amine selected from the group consisting of morpholine, piperidine, piperazine, and amines of the formula R 1 NR 2 R 3 , wherein R 1 is a C 1-4 alkyl or a C 2-4 hydroxyalkyl; and R 2 and R 3 are the same or different and are each hydrogen, a C 1-4 alkyl, or a C 2-4 hydroxyalkyl; and then converted to a salt by (3) (a) reacting the aminated epoxidized 1,3-diene polymer with a C 1-7 carboxylic acid or a mineral acid; or (b) alkylating the aminated epoxidized 1,3-diene polymer with 3-chloro-2-hydroxypropyl trimethylammonium chloride, RCl, RBr, or R 2 SO 4 wherein R is methyl or ethyl, to form a quaternary ammonium salt; or (c) quaternizing the aminated epoxidized 1,3-diene polymer with ethylene oxide, propylene oxide, glycidol, or glycidyl trimethylammonium chloride; and then further reacting the resulting product with a C 1-7 carboxylic acid or a mineral acid.
Claim 2
Dependent Claim
253 words
An aqueous shampoo composition for human hair consisting essentially of: (A) anionic surfactant present in an anionic surfactant effective amount; (B) amphoteric or zwitterionic surfactant present in an amphoteric or zwitterionic surfactant effective amount; and (C) cationic antistatic agent present in an antistatic effective amount, which agent is a cationic polymer that is the reaction product from: (1) a 1,3-diene homopolymer or predominantly 1,3-diene copolymer, having at least 10 1,3-diene units per molecule, in which at least 10% of the double bonds present have been epoxidized and which contains about 3-6% by weight of epoxide oxygen and which has been aminated with (2) amine selected from the group consisting of morpholine, piperidine, piperazine, and amines of the formula R 1 NR 2 R 3 , wherein R 1 is a C 1-4 alkyl or a C 2-4 hydroxyalkyl; and R 2 and R 3 are the same or different and are each hydrogen, a C 1-4 alkyl, or a C 2-4 hydroxyalkyl; and then converted to a salt by (3) (a) reacting the aminated epoxidized 1,3-diene polymer with a C 1-7 carboxylic acid or a mineral acid; or (b) alkylating the aminated epoxidized 1,3-diene polymer with 3-chloro-2-hydroxypropyl trimethylammonium chloride, RCl, RBr, or R 2 SO 4 wherein R is methyl or ethyl, to form a quaternary ammonium salt; or (c) quaternizing the aminated epoxidized 1,3-diene polymer with ethylene oxide, propylene oxide, glycidol, or glycidyl trimethylammonium chloride; and then further reacting the resulting product with a C 1-7 carboxylic acid or a mineral acid.
Claim 3
Dependent Claim
40 words
The shampoo composition of claim 1 wherein said 1,3-diene homopolymer or predominantly 1,3-diene copolymer is a homopolymer of 1,3-butadiene, 1,3-pentadiene, isoprene, or chloroprene or a copolymer of 1,3-butadiene, 1,3-pentadiene, isoprene, or chloroprene with ethylene, propylene, styrene, or acrylic acid derivatives.
Claim 4
Dependent Claim
21 words
The shampoo composition of claim 2 wherein more than 50% of the double bonds of said polymer are in a 1,4-cis-configuration.
Claim 5
Dependent Claim
21 words
The shampoo composition of claim 2 wherein said 1,3-diene is a butadiene homopolymer or copolymer which is liquid under ambient conditions.
Claim 6
Dependent Claim
26 words
The shampoo composition of claim 4 wherein said 1,3-diene is a butadiene homopolymer whose viscosity at 20° C. according to DIN 53,015 is approximately 3 poises.
Claim 7
Dependent Claim
18 words
The shampoo composition of claim 1 wherein epoxidation of said 1,3-diene polymer is by reaction with peracetic acid.
Claim 8
Dependent Claim
31 words
The shampoo composition of claim 1 wherein said amine is selected from the group consisting of methylamine, ethylamine, isopropylamine, monoethanolamine, dimethylamine, diethylamine, diethanolamine, morpholine, piperidine, piperazine, trimethylamine, triethylamine, triethanolamine, and N,N-dimethylethanolamine.
Claim 9
Dependent Claim
15 words
The shampoo composition of claim 7 where said amine is dimethylamine, monoethanolamine, methylamine or morpholine.
Claim 10
Dependent Claim
29 words
The shampoo composition of claim 1, wherein item (a) or (c) of part (3) is selected and said acid is acetic acid, lactic acid, glycolic acid, or hydrochloric acid.
Claim 11
Dependent Claim
18 words
The shampoo composition of claim 9 wherein item (3) (c) is selected and quaternization is with ethylene oxide.
Claim 12
Dependent Claim
54 words
The shampoo composition of claim 2, wherein: (1) said amine is selected from the group consisting of methylamine, ethylamine, isopropylamine, monoethanolamine, dimethylamine, diethylamine, diethanolamine, morpholine, piperidine, piperazine, trimethylamine, triethylamine, triethanolamine, and N,N-dimethylethanolamine; and (2) in item (a) or (c) of part (3), said acid is acetic acid, lactic acid, glycolic acid, or hydrochloric acid.
Claim 13
Dependent Claim
83 words
The shampoo composition of claim 1 wherein: (1) said 1,3-diene polymer is a butadiene homopolymer which is liquid under ambient conditions and wherein more than 50% of the double bonds of said polymer are in a 1-4-cis-configuration; (2) said amine is dimethylamine, monoethanolamine, methylamine, or morpholine; and (3) in item (3) (a) or (c) said acid is hydrochloric acid; in item (3) (b), the alkylating agent is 3-chloro-2-hydroxypropyl trimethyl ammonium chloride; and in item (3) (c) the quaternizing agent is glycidyl trimethylammonium chloride.
Claim 14
Dependent Claim
146 words
The shampoo composition of claim 1 wherein said anionic surfactant is: (i) an alkali metal, magnesium, ammonium, or C 1-7 -alkanol salt of a C 8-18 -alkyl sulfuric acid half ester; (ii) a C 8-18 -alkyl poly (1-6) ethylene glycol ether sulfuric acid half ester; (iii) a primary or secondary linear C 10-18 -alkane sulfonate; (iv) a C 10-18 -alkene sulfonate; (v) a hydroxy C 10-18 -alkane sulfonate; (vi) a higher fatty acid alkylol amide sulfate; (vii) a higher fatty acid aklylol amide polyethylene glycol ether sulfate; (viii) a sulfated higher fatty acid monoglyceride; (ix) a sulfosuccinic acid C 8-18 -monoalkyl ester; (x) a sulfosuccinic acid C 6-10 -dialkyl ester; (xi) a C 8-18 -alkyl poly (2-6) ethyleneglycol ether carboxylate; (xii) a C 8-18 -acyl sarcosine; (xiii) a C 8-18 -acyl tauride; (xiv) a C 8-18 -acyl isethionate; or (xv) a mixture thereof or salt thereof.
Claim 15
Dependent Claim
48 words
The shampoo composition of claim 1 wherein said amphoteric or zwitterionic surfactant is: (i) a C 8-18 -alkyl betaine; (ii) a C 8-18 -alkyl aminopropyl betaine; (iii) a C -18 -alkyl imidazolinium betaine; (iv) a C 8-18 alkyl amidocarboxylic acid; or (v) a mixture thereof or salt thereof.
Claim 16
Dependent Claim
48 words
The shampoo composition of claim 13 wherein said amphoteric or zwitterionic surfactant is: (i) a C 8-18 -alkyl betaine; (ii) a C 8-18 -alkyl aminopropyl betaine; (iii) a C -18 -alkyl imidazolinium betaine; (iv) a C 8-18 -alkyl amidocarboxylic acid; or (v) a mixture thereof or salt thereof.
Claim 17
Dependent Claim
23 words
The shampoo composition of claim 14 wherein said anionic surfactant is a C 8-18 -alkyl poly (1-6) ethyleneglycol ether sulfuric acid half ester.
Claim 18
Dependent Claim
22 words
The shampoo composition of claim 13 wherein said amphoteric or zwitterionic surfactant is: cocoalkyl dimethylaminoacetic acid; cocoalkylamidopropyl dimethylaminoacetic acid; or N-hydroxyethyl-N-cocoalkylamidoethyl glycine.
Claim 19
Dependent Claim
50 words
The shampoo composition of claim 16 wherein said anionic surfactant is present in about 5-30% by weight, said amphoteric or zwitterionic surfactant is present in about 1-5% by weight, and said cationic antistatic agent is present in about 0.1-10% by weight, all based upon the total weight of said composition.
Claim 20
Dependent Claim
18 words
The shampoo composition of claim 18 wherein said cationic antistatic agent is present in about 0.5-5% by weight.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-02-12 | 1993-08-14 | 1994-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-02-12 | 1997-08-14 | 1998-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-02-12 | 2001-08-14 | 2002-02-13 | $7700.00 | Window Closed / Lapsed |