CA1084845A - Quaternary ammonium derivatives of lanolin acids with branched-chain diol for cosmetic formulations - Google Patents
Quaternary ammonium derivatives of lanolin acids with branched-chain diol for cosmetic formulationsInfo
- Publication number
- CA1084845A CA1084845A CA283,738A CA283738A CA1084845A CA 1084845 A CA1084845 A CA 1084845A CA 283738 A CA283738 A CA 283738A CA 1084845 A CA1084845 A CA 1084845A
- Authority
- CA
- Canada
- Prior art keywords
- branched
- quaternary ammonium
- alkyl
- chain diol
- groups
- 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
- 239000004166 Lanolin Substances 0.000 title claims abstract description 59
- 229940039717 lanolin Drugs 0.000 title claims abstract description 59
- 235000019388 lanolin Nutrition 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 150000002009 diols Chemical class 0.000 title claims abstract description 34
- 239000002253 acid Substances 0.000 title claims abstract description 32
- 150000007513 acids Chemical class 0.000 title claims abstract description 20
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 8
- 238000009472 formulation Methods 0.000 title abstract description 21
- 239000002537 cosmetic Substances 0.000 title abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 claims description 19
- -1 acyl radicals Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 14
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical group 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 10
- 125000000129 anionic group Chemical group 0.000 abstract description 3
- 239000003995 emulsifying agent Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 21
- 210000004209 hair Anatomy 0.000 description 16
- 150000001408 amides Chemical class 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 4
- 229940008406 diethyl sulfate Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- ZZNDQCACFUJAKJ-UHFFFAOYSA-N 1-phenyltridecan-1-one Chemical compound CCCCCCCCCCCCC(=O)C1=CC=CC=C1 ZZNDQCACFUJAKJ-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940075529 glyceryl stearate Drugs 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- FDVKPDVESAUTEE-UHFFFAOYSA-N hexane-1,6-diol;2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O.OCCCCCCO FDVKPDVESAUTEE-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229940099367 lanolin alcohols Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/925—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of animal origin
-
- 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
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- A61Q5/12—Preparations containing hair conditioners
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Zoology (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/711,088 US4069347A (en) | 1976-08-02 | 1976-08-02 | Compositions of quaternary ammonium derivatives of lanolin acids |
| US711,088 | 1985-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1084845A true CA1084845A (en) | 1980-09-02 |
Family
ID=24856724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA283,738A Expired CA1084845A (en) | 1976-08-02 | 1977-07-29 | Quaternary ammonium derivatives of lanolin acids with branched-chain diol for cosmetic formulations |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4069347A (en, 2012) |
| JP (1) | JPS5319983A (en, 2012) |
| AU (1) | AU512426B2 (en, 2012) |
| BE (1) | BE857343A (en, 2012) |
| CA (1) | CA1084845A (en, 2012) |
| CH (1) | CH622698A5 (en, 2012) |
| DE (1) | DE2734654C2 (en, 2012) |
| ES (1) | ES461299A1 (en, 2012) |
| FR (1) | FR2360660A1 (en, 2012) |
| GB (1) | GB1590012A (en, 2012) |
| IT (1) | IT1085428B (en, 2012) |
| NL (1) | NL184994C (en, 2012) |
| PH (1) | PH17824A (en, 2012) |
| SE (1) | SE441801B (en, 2012) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220581A (en) * | 1977-07-01 | 1980-09-02 | Nl Industries, Inc. | Castor based quaternaries |
| US4224312A (en) * | 1978-10-23 | 1980-09-23 | Nl Industries, Inc. | Hair compositions containing castor based quaternaries |
| FR2443497A1 (fr) * | 1978-12-06 | 1980-07-04 | Oreal | Nouveaux agents de surface cationiques, procede pour les preparer et leur emploi |
| US4507280A (en) * | 1979-07-02 | 1985-03-26 | Clairol Incorporated | Hair conditioning composition and method for use |
| US4663158A (en) * | 1979-07-02 | 1987-05-05 | Clairol Incorporated | Hair conditioning composition containing cationic polymer and amphoteric surfactant and method for use |
| JPS5618910A (en) * | 1979-07-24 | 1981-02-23 | Kanebo Ltd | Liquid hair cosmetic |
| JPS5622713A (en) * | 1979-08-01 | 1981-03-03 | Kanebo Ltd | Liquid hair cosmetic |
| US4529586A (en) * | 1980-07-11 | 1985-07-16 | Clairol Incorporated | Hair conditioning composition and process |
| EP0095377B1 (en) * | 1982-05-25 | 1986-10-29 | Edward Sturdy Wilson | Improvements in or relating to iodophors |
| GB8300065D0 (en) * | 1982-05-25 | 1983-02-09 | Wilson E S | Quaternary ammonium compound disinfectants |
| US4631187A (en) * | 1982-09-29 | 1986-12-23 | S.C. Johnson & Son, Inc. | Hair treating composition containing a quaternary ammonium compound containing an erucyl group |
| JPH0617294B2 (ja) * | 1985-04-27 | 1994-03-09 | 三洋化成工業株式会社 | カチオン界面活性剤組成物 |
| JPH02166196A (ja) * | 1988-12-19 | 1990-06-26 | Lion Corp | 液状洗浄剤組成物 |
| US5696292A (en) * | 1995-02-10 | 1997-12-09 | Witco Corporation | Process for producing quarternary ammonium compounds |
| US5634969A (en) * | 1995-02-10 | 1997-06-03 | Rheox, Inc. | Organoclay compositions |
| CA2331668A1 (en) * | 1998-05-12 | 1999-11-18 | Goldschmidt Chemical Corporation | Clear personal care formulations containing quaternary ammonium compounds and other nitrogen-containing compounds |
| AU8383198A (en) * | 1998-06-29 | 2000-01-17 | Procter & Gamble Company, The | Method of conditioning hair |
| US6329353B1 (en) | 1999-05-12 | 2001-12-11 | Goldschmidt Chemical Corporation | Clear personal care formulations containing quaternary ammonium compounds and other nitrogen-containing compounds |
| US6087522A (en) * | 1999-10-12 | 2000-07-11 | Fan Tech Corporation | Silicone lanolin esters |
| DE60127209T2 (de) * | 2000-03-29 | 2007-12-20 | Croda, Inc. | Quaternäre fettsäure auf basis von anti-iso verbindungen |
| DE10126253A1 (de) * | 2001-05-29 | 2002-12-05 | Clariant Gmbh | Neuartig konfektionierte quaternäre Ammoniumverbindungen |
| DE10129225A1 (de) | 2001-06-19 | 2003-01-02 | Clariant Gmbh | Neuartig konfektionierte quaternäre Ammoniumverbindungen |
| BR0215245A (pt) * | 2001-12-21 | 2004-11-16 | Rhodia | Composição e método para fazer uma composição de alta fluidez aquosa de formulação estável, de múltiplas fases, para cuidado pessoal |
| RU2323250C2 (ru) | 2001-12-21 | 2008-04-27 | Родиа Инк. | Устойчивые поверхностно-активные композиции для суспендирования компонентов |
| US7012050B2 (en) | 2002-12-06 | 2006-03-14 | Colgate-Palmolive Company | Skin cleansing composition comprising a quaternized lanolin |
| CN1832720B (zh) * | 2003-07-22 | 2010-05-12 | 罗迪亚公司 | 一种用于个人护理制剂的新型支链硫酸盐 |
| RU2422450C2 (ru) * | 2003-11-19 | 2011-06-27 | Метабазис Терапеутикс, Инк. | Новые фосфорсодержащие тиромиметики |
| CN1997335A (zh) * | 2004-04-15 | 2007-07-11 | 罗迪亚公司 | 结构化表面活性剂组合物 |
| ES2401115T3 (es) * | 2004-08-17 | 2013-04-17 | Rhodia, Inc. | Composiciones tensioactivas estructuradas de pH bajo |
| US20060135627A1 (en) * | 2004-08-17 | 2006-06-22 | Seren Frantz | Structured surfactant compositions |
| EP1890768A2 (en) * | 2005-05-26 | 2008-02-27 | Metabasis Therapeutics, Inc. | Novel phosphinic acid-containing thyromimetics |
| JP2008542301A (ja) | 2005-05-26 | 2008-11-27 | メタバシス・セラピューティクス・インコーポレイテッド | 脂肪性肝疾患の処置のための甲状腺ホルモン様薬剤 |
| CN101641076B (zh) * | 2007-03-23 | 2014-08-06 | 罗迪亚公司 | 结构化表面活性剂组合物 |
| JP2020500199A (ja) | 2016-11-21 | 2020-01-09 | バイキング・セラピューティクス・インコーポレイテッド | グリコーゲン蓄積症の治療方法 |
| EA201992703A1 (ru) | 2017-06-05 | 2020-04-15 | Вайкинг Терапьютикс, Инк. | Композиции для лечения фиброза |
| MX2020009843A (es) | 2018-03-22 | 2020-12-11 | Viking Therapeutics Inc | Formas cristalinas y metodos de produccion de formas cristalinas de un compuesto. |
| US12102646B2 (en) | 2018-12-05 | 2024-10-01 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
| US2583772A (en) * | 1949-02-12 | 1952-01-29 | Dearborn Chemicals Co | Acid and quaternary salts of polyamides |
| US2668165A (en) * | 1951-12-22 | 1954-02-02 | American Cyanamid Co | Condensation products of higher fatty acids, polyalkylene polyamines, and organic halides |
| US2935474A (en) * | 1955-11-28 | 1960-05-03 | Visco Products Co | Process of inhibiting corrosion and corrosion inhibiting compositions |
| US3001996A (en) * | 1957-02-08 | 1961-09-26 | Hans S Mannheimer | Sulfates and sulfonates of n-tertiary amino alkyl-carboxylic acid amides |
| US3060096A (en) * | 1959-07-14 | 1962-10-23 | Colgate Palmolive Co | Cosmetic preparation and process for manufacture thereof |
| US3697644A (en) * | 1966-10-18 | 1972-10-10 | Gillette Co | Cosmetic composition |
| US3766267A (en) * | 1971-03-03 | 1973-10-16 | Dyk & Co Inc Van | Quaternary halides of gluconamides |
| US3970759A (en) * | 1972-12-11 | 1976-07-20 | Exxon Research And Engineering Company | Aliphatic diols as preservatives for cosmetics and related products |
| US3959461A (en) * | 1974-05-28 | 1976-05-25 | The United States Of America As Represented By The Secretary Of Agriculture | Hair cream rinse formulations containing quaternary ammonium salts |
| AU1298876A (en) * | 1975-05-19 | 1977-10-20 | American Cyanamid Co | Rinse |
-
1976
- 1976-08-02 US US05/711,088 patent/US4069347A/en not_active Expired - Lifetime
-
1977
- 1977-07-29 AU AU27460/77A patent/AU512426B2/en not_active Expired
- 1977-07-29 CA CA283,738A patent/CA1084845A/en not_active Expired
- 1977-08-01 DE DE2734654A patent/DE2734654C2/de not_active Expired
- 1977-08-01 IT IT26380/77A patent/IT1085428B/it active
- 1977-08-01 SE SE7708778A patent/SE441801B/xx not_active IP Right Cessation
- 1977-08-01 BE BE1008306A patent/BE857343A/xx not_active IP Right Cessation
- 1977-08-01 PH PH20055A patent/PH17824A/en unknown
- 1977-08-02 GB GB32432/77A patent/GB1590012A/en not_active Expired
- 1977-08-02 FR FR7723771A patent/FR2360660A1/fr active Granted
- 1977-08-02 ES ES461299A patent/ES461299A1/es not_active Expired
- 1977-08-02 CH CH950477A patent/CH622698A5/fr not_active IP Right Cessation
- 1977-08-02 JP JP9220077A patent/JPS5319983A/ja active Granted
- 1977-08-02 NL NLAANVRAGE7708557,A patent/NL184994C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4069347A (en) | 1978-01-17 |
| AU512426B2 (en) | 1980-10-03 |
| ES461299A1 (es) | 1978-08-16 |
| AU2746077A (en) | 1979-02-01 |
| NL184994B (nl) | 1989-08-01 |
| BE857343A (fr) | 1977-12-01 |
| PH17824A (en) | 1985-01-07 |
| JPS5319983A (en) | 1978-02-23 |
| NL184994C (nl) | 1990-01-02 |
| CH622698A5 (en, 2012) | 1981-04-30 |
| GB1590012A (en) | 1981-05-28 |
| DE2734654C2 (de) | 1986-08-07 |
| JPS6360725B2 (en, 2012) | 1988-11-25 |
| FR2360660A1 (fr) | 1978-03-03 |
| IT1085428B (it) | 1985-05-28 |
| FR2360660B1 (en, 2012) | 1982-11-05 |
| DE2734654A1 (de) | 1978-02-09 |
| SE7708778L (sv) | 1978-02-03 |
| NL7708557A (nl) | 1978-02-06 |
| SE441801B (sv) | 1985-11-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1084845A (en) | Quaternary ammonium derivatives of lanolin acids with branched-chain diol for cosmetic formulations | |
| US5939059A (en) | Hair conditioner and 2 in 1 conditioning shampoo | |
| US4734277A (en) | Bis-quaternary ammonium compounds | |
| US6207141B1 (en) | Conditioning compositions | |
| EP0292481B1 (en) | Particulate emulsifiable hair conditioning composition | |
| JP2002523343A (ja) | 毛髪の脱色およびハイライト化を行うための組成物 | |
| US3322676A (en) | Shampoos | |
| US5919743A (en) | Guerbet branched quaternary compounds in personal care applications | |
| JP2003523930A (ja) | オイル、脂肪酸、トリグリセリドのジアルキル第四アンモニウム誘導体及びその身体保護製品における使用 | |
| JP2003528125A (ja) | アンテイソ化合物に基づく脂肪クアット | |
| US4315912A (en) | Cationic surfactants | |
| EP1105093B1 (en) | Conditioning compositions | |
| US3865542A (en) | Hair dyeing compositions containing polyhydroxylated polyether nonionic surfactants | |
| CA2019551A1 (en) | Quaternized nitrogen containing compounds | |
| JP3880186B2 (ja) | 毛髪処理剤 | |
| GB2160421A (en) | Hair and fabric conditioning preparation | |
| JP3142633B2 (ja) | 透明リンス一体型シャンプー | |
| KR800001306B1 (ko) | 수용성 암모늄의 제조방법 | |
| US4224312A (en) | Hair compositions containing castor based quaternaries | |
| JPS6025479B2 (ja) | 香粧品・洗浄剤用界面活性剤組成物 | |
| JP2902797B2 (ja) | ヘアーリンス剤組成物 | |
| JPH1179942A (ja) | 毛髪組成物 | |
| KR20220039389A (ko) | 모발 컨디셔닝용 조성물 | |
| JPS6323843A (ja) | 新規４級アンモニウム化合物及びその用途 | |
| JPH06116123A (ja) | シャンプー組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |