CA1200202A - Salts of n-substituted-2-pyrrolidone-4-carboxylic acids as humectants - Google Patents
Salts of n-substituted-2-pyrrolidone-4-carboxylic acids as humectantsInfo
- Publication number
- CA1200202A CA1200202A CA000406683A CA406683A CA1200202A CA 1200202 A CA1200202 A CA 1200202A CA 000406683 A CA000406683 A CA 000406683A CA 406683 A CA406683 A CA 406683A CA 1200202 A CA1200202 A CA 1200202A
- Authority
- CA
- Canada
- Prior art keywords
- water
- pyrrolidone
- salt
- preparation
- acid
- 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
- 150000003839 salts Chemical class 0.000 title claims description 13
- 239000003906 humectant Substances 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 230000000699 topical effect Effects 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 241000124008 Mammalia Species 0.000 claims abstract description 5
- -1 Alkali metal salts Chemical class 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 6
- 159000000000 sodium salts Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000002253 acid Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008269 hand cream Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- DRMYLINAGHHBNG-UHFFFAOYSA-N 2-oxo-3h-furan-4-carboxylic acid Chemical compound OC(=O)C1=COC(=O)C1 DRMYLINAGHHBNG-UHFFFAOYSA-N 0.000 description 1
- PTVRUHCUZWTSTB-UHFFFAOYSA-N CN1C(CCC1)=O.[Na] Chemical compound CN1C(CCC1)=O.[Na] PTVRUHCUZWTSTB-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241001340526 Chrysoclista linneella Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000357437 Mola Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003788 bath preparation Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- CRPCXAMJWCDHFM-UHFFFAOYSA-M sodium;5-oxopyrrolidine-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1CCC(=O)N1 CRPCXAMJWCDHFM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Paints Or Removers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28144581A | 1981-07-08 | 1981-07-08 | |
| US281,445 | 1981-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1200202A true CA1200202A (en) | 1986-02-04 |
Family
ID=23077330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000406683A Expired CA1200202A (en) | 1981-07-08 | 1982-07-06 | Salts of n-substituted-2-pyrrolidone-4-carboxylic acids as humectants |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0069512B1 (en, 2012) |
| JP (1) | JPS5830330A (en, 2012) |
| KR (1) | KR860000272B1 (en, 2012) |
| AT (1) | ATE20181T1 (en, 2012) |
| AU (1) | AU532114B2 (en, 2012) |
| CA (1) | CA1200202A (en, 2012) |
| DE (1) | DE3271532D1 (en, 2012) |
| DK (1) | DK304682A (en, 2012) |
| ES (1) | ES8307744A1 (en, 2012) |
| FI (1) | FI76925C (en, 2012) |
| GR (1) | GR77255B (en, 2012) |
| IE (1) | IE53203B1 (en, 2012) |
| IL (1) | IL66256A (en, 2012) |
| PH (1) | PH17648A (en, 2012) |
| PT (1) | PT75210B (en, 2012) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3373438D1 (en) * | 1982-05-20 | 1987-10-15 | Stiksack Sts S A | Plastics film and bags and sacks therefrom |
| US4933463A (en) * | 1989-05-08 | 1990-06-12 | Gaf Chemicals Corporation | Polymerizable pyrrolidonyl oxazoline monomers, homopolymers and copolymers |
| US6897100B2 (en) | 1993-11-05 | 2005-05-24 | Semiconductor Energy Laboratory Co., Ltd. | Method for processing semiconductor device apparatus for processing a semiconductor and apparatus for processing semiconductor device |
| GB9826656D0 (en) | 1998-12-03 | 1999-01-27 | Novartis Ag | Organic compounds |
| US6669767B2 (en) | 2002-03-08 | 2003-12-30 | Eastman Kodak Company | Ink jet printing process |
| US6669768B2 (en) | 2002-03-08 | 2003-12-30 | Eastman Kodak Company | Ink jet ink set |
| DE102005006421A1 (de) | 2005-02-12 | 2006-08-24 | Clariant Produkte (Deutschland) Gmbh | Polymere und ihre Herstellung und Verwendung als Gashydratinhibitoren |
| DE102007037017A1 (de) | 2007-08-06 | 2009-02-19 | Clariant International Ltd. | 1-Alkyl-5-oxo-pyrrolidin-3-carbonsäureester mit verbesserter biologischer Abbaubarkeit |
| DE102007037016B4 (de) | 2007-08-06 | 2011-06-30 | Clariant International Limited | Verwendung von 1-Alkyl-5-oxo-pyrrolidin-3-carbonsäureestern als Gashydratinhibitoren mit verbesserter biologischer Abbaubarkeit |
| DE102008003826B4 (de) | 2008-01-10 | 2010-07-22 | Clariant International Limited | Verwendung von Salzen als Korrosionsinhibitoren mit erhöhter biologischer Abbaubarkeit und verminderter Toxizität und diese Salze |
| DE102008003828B3 (de) | 2008-01-10 | 2009-09-03 | Clariant International Limited | Verwendung von Salzen als Korrosionsinhibitoren mit erhöhter biologischer Abbaubarkeit und verminderter Toxizität und diese Salze |
| FR2939310B1 (fr) | 2008-12-08 | 2012-04-20 | Oreal | Compositions cosmetiques comprenant un derive ester de 2-pyrrolidinone 4-carboxy et un filtre lipophile triazine ; utilisation dudit derive comme solvant d'un filtre lipophile triazine |
| FR2939309B1 (fr) | 2008-12-08 | 2010-12-17 | Oreal | Utilisation d'un derive ester de 2-pyrrolidinone 4-carboxy comme solvant dans les compositions cosmetiques ; compositions cosmetiques les contenant |
| FR2939315B1 (fr) | 2008-12-08 | 2011-01-21 | Oreal | Composition cosmetique contenant un derive de dibenzoylmethane et un compose ester de 2-pyrrolidinone 4-carboxy ; procede de photostabilisation du derive de dibenzoylmethane |
| WO2011054387A1 (en) * | 2009-11-05 | 2011-05-12 | L'oreal | Cosmetic compositions comprising an ester derived from 4-carboxy-2-pyrrolidinone and a merocyanin screening agent; use of said derivative as a solvent for a merocyanin screening agent |
| WO2011054388A1 (en) * | 2009-11-05 | 2011-05-12 | L'oreal | Cosmetic compositions comprising an ester derived from 4-carboxy-2-pyrrolidinone and a lipophilic screening agent; use of said derivative as a solvent for a benzophenone lipophilic screening agent |
| FR2961093A1 (fr) * | 2010-06-09 | 2011-12-16 | Oreal | Composition cosmetique comprenant un polymere et un derive de 4-carboxy 2-pyrrolidinone, procede de traitement cosmetique et compose |
| FR2961094B1 (fr) * | 2010-06-09 | 2012-11-16 | Oreal | Utilisation de derive de 4-carboxy 2-pyrrolidinone dans une composition cosmetique comprenant une matiere particulaire |
| FR2961096B1 (fr) * | 2010-06-09 | 2013-01-18 | Oreal | Compositions cosmetiques comprenant un derive de 4- carboxy 2-pyrrolidinone et un filtre uv inorganique ; utilisation dudit derive comme agent dispersant d'un filtre inorganique |
| FR2961101B1 (fr) | 2010-06-09 | 2013-01-25 | Oreal | Composition comprenant au moins une 2-pyrrolidone fonctionnalisee par un radical ester ou amide, et au moins un pigment ou un colorant direct pour la teinture des matieres keratiniques |
| CN101974042B (zh) * | 2010-10-29 | 2013-01-30 | 川渝中烟工业有限责任公司 | 五碳或六碳单糖-(e)-3-(呋喃-2-基)丙烯酸双酯类化合物及其制备方法和用途 |
| CN101974040B (zh) * | 2010-10-29 | 2013-01-30 | 川渝中烟工业有限责任公司 | 五碳或六碳单糖-l-孟氧基乙酸单酯类化合物及其制备方法和用途 |
| CN101974039B (zh) * | 2010-10-29 | 2013-01-30 | 川渝中烟工业有限责任公司 | 五碳或六碳单糖-(e)-3-(呋喃-2-基)丙烯酸单酯类化合物及其制备方法和用途 |
| FR2977153B1 (fr) | 2011-06-29 | 2013-08-02 | Oreal | Composition cosmetique comprenant une huile fonctionnalisee et un solvant et procede de traitement cosmetique |
| WO2013010590A1 (en) | 2011-07-21 | 2013-01-24 | L'oreal | Cosmetic and/or dermatological composition containing a merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities |
| DE102011119545A1 (de) | 2011-11-26 | 2013-05-29 | Clariant International Ltd. | Zusammensetzungen enthaltend ein Tensid aus der Gruppe der Pyrrolidoncarbonsäuren und deren Salzen und ein Betaintensid und deren Verwendung in der Kosmetik sowie in Wasch- und Reinigungsmitteln |
| DE102012017739A1 (de) | 2012-09-07 | 2014-03-13 | Clariant International Ltd. | Verfahren zur Herstellung von N-substituierten Pyrrolidoncarbonsäureestern |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2757125A (en) * | 1952-05-16 | 1956-07-31 | Colgate Palmolive Co | N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith |
| FR1348617A (fr) * | 1961-12-12 | 1964-01-10 | Gillette Co | Compositions solides renfermant l'acide 2-pyrrolidone-5-carboxylique, ses dérivés et leurs sels comme agents humectants |
| US3235457A (en) * | 1962-12-07 | 1966-02-15 | Gillette Co | Humectant |
| GB1323061A (en) * | 1969-06-16 | 1973-07-11 | Castrol Ltd | Functional fluids and additives therefor |
| US3803141A (en) * | 1972-08-14 | 1974-04-09 | Burdick & Jackson Labor Inc | 10-(1-substituted-3-pyrrolidylmethyl)phenothiazines |
| US4253979A (en) * | 1979-02-05 | 1981-03-03 | Exxon Research & Engineering Co. | Lubricating grease composition containing pyrrolidone derivative as grease thickener |
| JPS5835092B2 (ja) * | 1979-05-12 | 1983-07-30 | トヨタ自動車株式会社 | 耐アトリシヨン性粒状体の製造方法 |
-
1982
- 1982-06-25 DE DE8282303312T patent/DE3271532D1/de not_active Expired
- 1982-06-25 EP EP82303312A patent/EP0069512B1/en not_active Expired
- 1982-06-25 AT AT82303312T patent/ATE20181T1/de not_active IP Right Cessation
- 1982-06-30 IE IE1597/82A patent/IE53203B1/en unknown
- 1982-07-05 GR GR68647A patent/GR77255B/el unknown
- 1982-07-06 CA CA000406683A patent/CA1200202A/en not_active Expired
- 1982-07-07 DK DK304682A patent/DK304682A/da not_active Application Discontinuation
- 1982-07-07 AU AU85696/82A patent/AU532114B2/en not_active Ceased
- 1982-07-07 ES ES513791A patent/ES8307744A1/es not_active Expired
- 1982-07-07 KR KR8203025A patent/KR860000272B1/ko not_active Expired
- 1982-07-07 PT PT75210A patent/PT75210B/pt not_active IP Right Cessation
- 1982-07-07 PH PH27532A patent/PH17648A/en unknown
- 1982-07-07 FI FI822414A patent/FI76925C/fi not_active IP Right Cessation
- 1982-07-08 IL IL66256A patent/IL66256A/xx unknown
- 1982-07-08 JP JP57119145A patent/JPS5830330A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GR77255B (en, 2012) | 1984-09-11 |
| FI822414A0 (fi) | 1982-07-07 |
| EP0069512B1 (en) | 1986-06-04 |
| DK304682A (da) | 1983-01-09 |
| FI76925B (fi) | 1988-09-30 |
| PT75210B (en) | 1985-10-04 |
| ATE20181T1 (de) | 1986-06-15 |
| EP0069512A3 (en) | 1984-03-07 |
| KR840000236A (ko) | 1984-02-18 |
| PH17648A (en) | 1984-10-18 |
| IE821597L (en) | 1983-01-08 |
| EP0069512A2 (en) | 1983-01-12 |
| ES513791A0 (es) | 1983-08-01 |
| AU8569682A (en) | 1983-02-03 |
| PT75210A (en) | 1982-08-01 |
| FI822414L (fi) | 1983-01-09 |
| IE53203B1 (en) | 1988-08-31 |
| FI76925C (fi) | 1989-01-10 |
| DE3271532D1 (en) | 1986-07-10 |
| ES8307744A1 (es) | 1983-08-01 |
| IL66256A0 (en) | 1982-11-30 |
| AU532114B2 (en) | 1983-09-15 |
| JPS5830330A (ja) | 1983-02-22 |
| JPH0157615B2 (en, 2012) | 1989-12-06 |
| IL66256A (en) | 1986-03-31 |
| KR860000272B1 (ko) | 1986-03-26 |
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