GB939148A - Process for the preparation of a permanent wave - Google Patents
Process for the preparation of a permanent waveInfo
- Publication number
- GB939148A GB939148A GB1873/62A GB187362A GB939148A GB 939148 A GB939148 A GB 939148A GB 1873/62 A GB1873/62 A GB 1873/62A GB 187362 A GB187362 A GB 187362A GB 939148 A GB939148 A GB 939148A
- Authority
- GB
- United Kingdom
- Prior art keywords
- epoxy
- compounds
- diglycidyl ether
- water
- hair
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 16
- 239000004593 Epoxy Substances 0.000 abstract 10
- 239000003795 chemical substances by application Substances 0.000 abstract 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 4
- 125000003700 epoxy group Chemical group 0.000 abstract 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- 150000004985 diamines Chemical class 0.000 abstract 3
- -1 e.g. Substances 0.000 abstract 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 abstract 2
- JROOCDXTPKCUIO-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)CCOCC1CO1 JROOCDXTPKCUIO-UHFFFAOYSA-N 0.000 abstract 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 abstract 2
- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 abstract 2
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 abstract 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000004475 Arginine Substances 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 2
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 abstract 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 abstract 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 abstract 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 abstract 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 abstract 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 2
- 239000004472 Lysine Substances 0.000 abstract 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 abstract 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 2
- 239000001361 adipic acid Substances 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract 2
- 229960003121 arginine Drugs 0.000 abstract 2
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 abstract 2
- 229960001927 cetylpyridinium chloride Drugs 0.000 abstract 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 abstract 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 abstract 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract 2
- 229960003067 cystine Drugs 0.000 abstract 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 abstract 2
- 229960003646 lysine Drugs 0.000 abstract 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 2
- 229960003151 mercaptamine Drugs 0.000 abstract 2
- 229960003104 ornithine Drugs 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 2
- 238000009736 wetting Methods 0.000 abstract 2
- 239000000080 wetting agent Substances 0.000 abstract 2
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical class [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 abstract 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 229910001385 heavy metal Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 238000004804 winding Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/02—Resin hair settings
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Abstract
A composition suitable for use in the waving of hair comprises one or more compounds having at least two epoxy groups per molecule and a bifunctional compound containing amino, carboxylic acid and/or mercapto groups and having a curing effect on the epoxy compounds, dissolved in water, a water miscible solvent, e.g. isopropyl alcohol, or a mixture of water with a water-miscible solvent. Suitable epoxy compounds are ethylene glycol diglycidyl ether, 1,3 butane diol diglycidyl ether, 1,4 butane diol diglycidyl ether, glycerin-diglycidyl ether, 1-epoxy ethyl-3,4-epoxy cyclohexane, 3,4 epoxy-6-methyl-cyclohexyl methyl-31,41-epoxy-61-me-thyl cyclohexane carboxylate, dicyclo pentadiene diepoxide, butadiene diepoxide and diglycidyl ether and suitable curing agents are ethylene diamine diethylene triamine, dipropylene triamine, 3,4 diamino benzoic acid, lysine, ornithine, arginine, cystine, N,N1 bishydroxyethylethylene diamine, the hydroxyl group containing diamines prepared by reacting the epoxy compounds specified with ammonia, cysteamine, cystein, maleic acid anhydride and adipic acid. The proportion of epoxy compounds to curing agent is preferably such that one reactive hydrogen atom of the curing agent is available per epoxy group. The composition may also contain compounds having an accelerating action upon the formation of the resin, e.g. resorcinol, heavy metal salts, e.g. CuSO4. 5H2O, thiosemicarbazide and cation active wetting agents, e.g. cetyl pyridinium chloride. After treatment with the composition the hair may be wound upon curlers and dried.ALSO:Hair is permanently waved by wetting it with a solution containing one or more compounds having at least two epoxy groups per molecule and with a curing agent solution which contains bifunctional compounds having amino, carboxylic acid and/or mercapto groups having a curing effect on the epoxy compounds, the epoxy compounds and curing agents being dissolved in water, in mixtures of water with water-miscible solvents, e.g., isopropyl alcohol, or in water-miscible solvents, or by wetting it with a mixture of both such solutions, and then winding it upon curlers and drying. Suitable epoxy compounds are ethylene glycol diglycidyl ether, 1,3butane diol diglycidyl ether, 1,4-butane diol diglycidyl ether, glycerindi-glycidyl ether, 1-epoxy ethyl-3,4-epoxy cyclo-hexane, 3,4-epoxy-6-methyl-cyclohexyl methyl-31,41-epoxy-61-methyl cyclohexane carboxylate, dicyclopentadiene diepoxide, butadiene diepoxide and diglycidyl ether and suitable curing agents are ethylene diamine, diethylene triamine, dipropylene triamine, 3,4-diamino benzoic acid, lysine, ornithine, arginine, cystine, N,N1bis hydroxyethyl-ethylene diamine, the hydroxyl group containing diamines prepared by reacting the epoxy compounds specified with ammonia, cysteamine, cystein, maleic acid anhydride and adipic acid. The proportion of epoxy compounds to curing agent is preferably such that are reactive hydrogen atom of the curing agent is available per epoxy group. The hair may be treated with a dilute solution of the epoxy compound and curing agent which acts while the hair is in curlers and can be reacted under the drier without removal of the surplus or with a concentrated solution which is left to act for a few minutes after which the surplus is removed by rubbing or washing the hair is placed in curlers and dried under the drier. The solutions may contain compounds having an accelerating action upon the formation of the resin, e.g. resorcinol, heavy water salts, e.g. CuSO4.SH2O, thiosemicarbazide and cation-active wetting agents, e.g. cetyl pyridinium chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW29518A DE1154901B (en) | 1961-02-22 | 1961-02-22 | Method of making a permanent hairstyle |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB939148A true GB939148A (en) | 1963-10-09 |
Family
ID=7599252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1873/62A Expired GB939148A (en) | 1961-02-22 | 1962-01-18 | Process for the preparation of a permanent wave |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3250682A (en) |
| DE (1) | DE1154901B (en) |
| GB (1) | GB939148A (en) |
| NL (1) | NL274938A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109252192A (en) * | 2017-07-14 | 2019-01-22 | 罗门哈斯电子材料有限责任公司 | The method of the nickel electroplating composition and electronickelling of copolymer with arginine and di-epoxide |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013787A (en) * | 1971-11-29 | 1977-03-22 | Societe Anonyme Dite: L'oreal | Piperazine based polymer and hair treating composition containing the same |
| LU64371A1 (en) * | 1971-11-29 | 1973-06-21 | ||
| US4635654A (en) * | 1985-11-04 | 1987-01-13 | Redken Laboratories, Inc. | Method for evaluating efficacy of a hair styling product |
| US7001988B2 (en) * | 2001-09-25 | 2006-02-21 | Keraplast Technologies, Ltd. | Methods for controlling peptide solubility, chemically modified peptides, and stable solvent systems for producing same |
| US6914126B2 (en) * | 2002-04-10 | 2005-07-05 | Keraplast Technologies, Ltd. | Methods for producing, films comprising, and methods for using heterogenous crosslinked protein networks |
| US7001987B2 (en) * | 2002-04-22 | 2006-02-21 | Keraplast Technologies, Ltd. | Hydrogel with controllable mechanical, chemical, and biological properties and method for making same |
| WO2003087156A2 (en) * | 2002-04-10 | 2003-10-23 | Keraplast Technologies, Ltd. | Heterogeneous crosslinked protein networks and methods for producing them |
| US6989437B2 (en) * | 2002-04-10 | 2006-01-24 | Keraplast Technologies, Ltd. | Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks |
| US20040120910A1 (en) * | 2002-04-10 | 2004-06-24 | Dyke Mark Van | Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks |
| US20040062793A1 (en) * | 2002-07-05 | 2004-04-01 | Dyke Mark Van | Tissue defect dressings comprising proteinaceous networks |
| US7163321B2 (en) * | 2002-07-25 | 2007-01-16 | Steven Contarino | Emergency vehicle grille |
| US9783905B2 (en) * | 2014-12-30 | 2017-10-10 | Rohm and Haas Electronic Mateirals LLC | Reaction products of amino acids and epoxies |
| CA3182348A1 (en) * | 2020-05-04 | 2021-11-11 | Landa Labs (2012) Ltd. | Compositions, kits and methods for styling hair fibers |
| AU2022268316B2 (en) * | 2020-05-04 | 2024-09-26 | Landa Labs (2012) Ltd. | Compositions, kits and methods for styling hair fibers |
| EP4000599A1 (en) * | 2020-11-17 | 2022-05-25 | Beiersdorf AG | Novel skin moisturizer |
| EP4000692A1 (en) * | 2020-11-17 | 2022-05-25 | Beiersdorf AG | Two component sunscreen |
| EP4000693A1 (en) * | 2020-11-17 | 2022-05-25 | Beiersdorf AG | Two component moisturizer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2070990A (en) * | 1934-06-25 | 1937-02-16 | Shell Dev | Treatment of halogenated polyhydric alcohols |
| US2585115A (en) * | 1945-09-18 | 1952-02-12 | Devoe & Raynolds Co | Amine-epoxide compositions |
| US2510885A (en) * | 1946-03-08 | 1950-06-06 | Devoe & Raynolds Co | Amine-epoxy-phenol compositions |
| US3052650A (en) * | 1953-03-27 | 1962-09-04 | Minnesota Mining & Mfg | Heat-curing epoxy resin compositions |
-
0
- NL NL274938D patent/NL274938A/xx unknown
-
1961
- 1961-02-22 DE DEW29518A patent/DE1154901B/en active Pending
-
1962
- 1962-01-18 GB GB1873/62A patent/GB939148A/en not_active Expired
- 1962-02-15 US US173482A patent/US3250682A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109252192A (en) * | 2017-07-14 | 2019-01-22 | 罗门哈斯电子材料有限责任公司 | The method of the nickel electroplating composition and electronickelling of copolymer with arginine and di-epoxide |
| CN109252192B (en) * | 2017-07-14 | 2020-12-25 | 罗门哈斯电子材料有限责任公司 | Nickel electroplating composition having copolymer of arginine and diepoxide and method of electroplating nickel |
Also Published As
| Publication number | Publication date |
|---|---|
| US3250682A (en) | 1966-05-10 |
| NL274938A (en) | |
| DE1154901B (en) | 1963-09-26 |
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