DE2151739C3 - Verfahren zur Herstellung neuer als haarkosmetische Wirkstoffe brauchbarer Oligopeptidderivate - Google Patents
Verfahren zur Herstellung neuer als haarkosmetische Wirkstoffe brauchbarer OligopeptidderivateInfo
- Publication number
- DE2151739C3 DE2151739C3 DE2151739A DE2151739A DE2151739C3 DE 2151739 C3 DE2151739 C3 DE 2151739C3 DE 2151739 A DE2151739 A DE 2151739A DE 2151739 A DE2151739 A DE 2151739A DE 2151739 C3 DE2151739 C3 DE 2151739C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- active ingredients
- production
- hair cosmetic
- cosmetic active
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 108010038807 Oligopeptides Proteins 0.000 title claims description 6
- 102000015636 Oligopeptides Human genes 0.000 title claims description 6
- 239000004480 active ingredient Substances 0.000 title claims description 4
- 239000002537 cosmetic Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 235000018102 proteins Nutrition 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- -1 fatty acid esters Chemical class 0.000 description 8
- 238000007098 aminolysis reaction Methods 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 108010076119 Caseins Proteins 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 230000003766 combability Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000003531 protein hydrolysate Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- WPOHUQOEJUSLGO-UHFFFAOYSA-N 3,4-dihydroxybutanamide Chemical class NC(=O)CC(O)CO WPOHUQOEJUSLGO-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000011632 Caseins Human genes 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OUQGOXCIUOCDNN-UHFFFAOYSA-N Glycidyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1CO1 OUQGOXCIUOCDNN-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 230000003752 improving hair Effects 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 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
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
- C07K1/126—Aminolysis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Cosmetics (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2151739A DE2151739C3 (de) | 1971-10-18 | 1971-10-18 | Verfahren zur Herstellung neuer als haarkosmetische Wirkstoffe brauchbarer Oligopeptidderivate |
| SE7212355A SE389120B (sv) | 1971-10-18 | 1972-09-25 | Forfarande for framstellning av nya, sasom harkosmetiskt aktiva substanser anvendbara oligopeptidderivat |
| NL7212956A NL7212956A (enExample) | 1971-10-18 | 1972-09-25 | |
| US00294187A US3824228A (en) | 1971-10-18 | 1972-10-02 | Oligopeptide derivatives and process for the preparation thereof using glycidyl esters of carboxylic acids to react with protein-diamine aminolyzates |
| IT30430/72A IT1001508B (it) | 1971-10-18 | 1972-10-13 | Procedimento per la preparazione di derivati di oligopeptidi |
| CH1514972A CH580571A5 (enExample) | 1971-10-18 | 1972-10-17 | |
| GB4775272A GB1364991A (en) | 1971-10-18 | 1972-10-17 | Process for the preparation of oligopeptide derivatives |
| AT889772A AT330804B (de) | 1971-10-18 | 1972-10-17 | Verfahren zur herstellung neuer oligopeptidderivate |
| FR7236848A FR2156780B1 (enExample) | 1971-10-18 | 1972-10-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2151739A DE2151739C3 (de) | 1971-10-18 | 1971-10-18 | Verfahren zur Herstellung neuer als haarkosmetische Wirkstoffe brauchbarer Oligopeptidderivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2151739A1 DE2151739A1 (de) | 1973-04-26 |
| DE2151739B2 DE2151739B2 (de) | 1975-03-20 |
| DE2151739C3 true DE2151739C3 (de) | 1975-10-30 |
Family
ID=5822616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2151739A Expired DE2151739C3 (de) | 1971-10-18 | 1971-10-18 | Verfahren zur Herstellung neuer als haarkosmetische Wirkstoffe brauchbarer Oligopeptidderivate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3824228A (enExample) |
| AT (1) | AT330804B (enExample) |
| CH (1) | CH580571A5 (enExample) |
| DE (1) | DE2151739C3 (enExample) |
| FR (1) | FR2156780B1 (enExample) |
| GB (1) | GB1364991A (enExample) |
| IT (1) | IT1001508B (enExample) |
| NL (1) | NL7212956A (enExample) |
| SE (1) | SE389120B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115548A (en) * | 1974-01-18 | 1978-09-19 | The Procter & Gamble Company | Detergent compositions comprising modified proteins |
| US4076800A (en) * | 1975-01-13 | 1978-02-28 | The Procter & Gamble Company | Protein-containing detergent compositions for protecting keratinous materials |
| DE2945100A1 (de) * | 1979-11-08 | 1981-05-21 | Henkel KGaA, 4000 Düsseldorf | Neuartige tenside, deren herstellung und verwendung in hautfreundlichen spuel-, wasch- und reinigungsmitteln sowie enthaltende hautfreundliche, insbesondere kosmetische zubereitungen |
| CA1166576A (en) * | 1980-08-19 | 1984-05-01 | Lorna C. Staples | Whey protein containing cosmetic formulations |
| US4369037A (en) * | 1980-11-19 | 1983-01-18 | Kao Soap Co., Ltd. | Hair treatment cosmetics containing cationic keratin derivatives |
| EP0109074A1 (en) * | 1982-11-16 | 1984-05-23 | Inolex Chemical Company | Quarternary ammonium derivatives of amino acid units |
| DE3517205A1 (de) * | 1985-05-13 | 1986-11-13 | Henkel KGaA, 4000 Düsseldorf | Oligopeptid-derivate, deren herstellung und deren verwendung als hautfreundliche tenside |
| ES2241430B1 (es) * | 2003-04-04 | 2006-12-01 | Actherm Inc. | Termometro electronico dotado de visualizacion por pantalla de cristal liquido ajustable en orientacion. |
| DE102007033650A1 (de) * | 2007-07-17 | 2009-01-22 | Henkel Ag & Co. Kgaa | Haarbehandlungsmittel mit Oligopeptiden |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138581A (en) * | 1959-10-12 | 1964-06-23 | Swift & Co | Surface active acylated amidated peptides and polypeptides |
| FR1520356A (fr) * | 1961-12-06 | 1968-04-12 | Tech B E T Bureau Et | Procédé de traitement de protéines ainsi que de leurs produits d'hydrolyse et produits ainsi obtenus |
| DE1959651C3 (de) * | 1969-11-28 | 1973-11-15 | Henkel & Cie Gmbh, 4000 Duesseldorf | Verfahren zur Herstellung lag kettiger Alkylol und Acylgruppen ent haltender Oligopeptiddenvate |
-
1971
- 1971-10-18 DE DE2151739A patent/DE2151739C3/de not_active Expired
-
1972
- 1972-09-25 NL NL7212956A patent/NL7212956A/xx not_active Application Discontinuation
- 1972-09-25 SE SE7212355A patent/SE389120B/xx unknown
- 1972-10-02 US US00294187A patent/US3824228A/en not_active Expired - Lifetime
- 1972-10-13 IT IT30430/72A patent/IT1001508B/it active
- 1972-10-17 GB GB4775272A patent/GB1364991A/en not_active Expired
- 1972-10-17 CH CH1514972A patent/CH580571A5/xx not_active IP Right Cessation
- 1972-10-17 AT AT889772A patent/AT330804B/de not_active IP Right Cessation
- 1972-10-18 FR FR7236848A patent/FR2156780B1/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Nichts ermittelt * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2156780A1 (enExample) | 1973-06-01 |
| SE389120B (sv) | 1976-10-25 |
| IT1001508B (it) | 1976-04-30 |
| CH580571A5 (enExample) | 1976-10-15 |
| US3824228A (en) | 1974-07-16 |
| DE2151739A1 (de) | 1973-04-26 |
| AT330804B (de) | 1976-07-26 |
| DE2151739B2 (de) | 1975-03-20 |
| ATA889772A (de) | 1975-10-15 |
| FR2156780B1 (enExample) | 1978-05-26 |
| NL7212956A (enExample) | 1973-04-24 |
| GB1364991A (en) | 1974-08-29 |
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