US3793210A - Keto acid containing compositions - Google Patents
Keto acid containing compositions Download PDFInfo
- Publication number
- US3793210A US3793210A US00177855A US3793210DA US3793210A US 3793210 A US3793210 A US 3793210A US 00177855 A US00177855 A US 00177855A US 3793210D A US3793210D A US 3793210DA US 3793210 A US3793210 A US 3793210A
- Authority
- US
- United States
- Prior art keywords
- acid
- composition
- keto acid
- shampoo
- keto
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 150000004715 keto acids Chemical class 0.000 title claims abstract description 30
- 239000004094 surface-active agent Substances 0.000 claims abstract description 17
- 239000003599 detergent Substances 0.000 claims description 15
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 12
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 10
- 229940040102 levulinic acid Drugs 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 229940107700 pyruvic acid Drugs 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 239000002563 ionic surfactant Substances 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- MKHVZQXYWACUQC-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;dodecyl sulfate Chemical group OCCNCCO.CCCCCCCCCCCCOS(O)(=O)=O MKHVZQXYWACUQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 abstract description 32
- 238000005187 foaming Methods 0.000 abstract description 4
- -1 fatty acid esters Chemical class 0.000 description 21
- 239000006260 foam Substances 0.000 description 9
- 239000008233 hard water Substances 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000003750 conditioning effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008234 soft water Substances 0.000 description 3
- 239000000271 synthetic detergent Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- SPFVNQBOHYXSMM-UHFFFAOYSA-M 1-decylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCC[N+]1=CC=CC=C1 SPFVNQBOHYXSMM-UHFFFAOYSA-M 0.000 description 1
- CSHOPPGMNYULAD-UHFFFAOYSA-N 1-tridecoxytridecane Chemical compound CCCCCCCCCCCCCOCCCCCCCCCCCCC CSHOPPGMNYULAD-UHFFFAOYSA-N 0.000 description 1
- OAVHXBONEDQFLJ-UHFFFAOYSA-N 4-ethoxy-4-oxo-3-sulfobutanoic acid Chemical compound CCOC(=O)C(S(O)(=O)=O)CC(O)=O OAVHXBONEDQFLJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 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
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FKOPCVJGLLMUNP-UHFFFAOYSA-N decylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCN FKOPCVJGLLMUNP-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- PFKRTWCFCOUBHS-UHFFFAOYSA-N dimethyl(octadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH+](C)C PFKRTWCFCOUBHS-UHFFFAOYSA-N 0.000 description 1
- CDMFJJBPEJLFMB-UHFFFAOYSA-M dimethyl-[2-(2-phenoxyethoxy)ethyl]-(1-phenylnonyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1OCCOCC[N+](C)(C)C(CCCCCCCC)C1=CC=CC=C1 CDMFJJBPEJLFMB-UHFFFAOYSA-M 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical class [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 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
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 239000001993 wax Substances 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
- A61Q5/02—Preparations for cleaning 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
Definitions
- the instant invention is directed to novel surfactant and shampoo compositions.
- the instant invention is directed to surfactant and shampoo compositions which contain keto acid.
- shampoos and surfactant compositions there are numerous types of shampoos and surfactant compositions on the market at present. Many of these compositions are based on soaps although there are numerous compositions which contain synthetic detergent preparations. Such detergent preparations contain primarily organic sulfates and sulfonates. These detergent compositions are favored by many consumers because they do an extremely thorough cleaning job and further do not leave dulling lime soaps on the hair when hard water is employed.
- the synthetic detergents are better cleaners in that they effectively remove excess oils from the hair. Furthermore, the hair is more easily washed with said detergents than with soap because the use of soap requires that it be removed as thoroughly as possible from the hair by asubsequent prolonged rinsing treatment with water, which may leave behind an undesirable degree of alkalinity on the scalp.
- a particular ingredient which will impart to the shampoo one or perhaps several of the requisite properties in an outstanding manner will adversely affect one or more of the remaining properties.
- soapbased shampoos in soft water, have excellent cleaning, lathering and hair conditioning properties; however, any hardness in water adversely affects the lathering characteristics and leaves the well known undesirable hard water soap curd.
- Sequestering and curd dispersing additives have improved soap shampoos to some extent but the majority of successful shampoos are based on those non-soap synthetic detergents which lather and clean well in hard or soft water.
- Such non-soap detergents however, have the shortcoming of cleaning so well that the natural oil of the hair, which naturally conditions the hair, is removed leaving it harsh and unmanageable.
- shampoo preparation is designed to preserve much of the natural oil in the hair, the criticism can be voiced that it does an incomplete cleaning job.
- Some shampoos attempt to solve this problem by using a highly effective detergent with a hair conditioning agent which serves as a replacement for the oil removed from the hair.
- hair condioning agents are polyglycols, fatty acid esters of glycols, natural or synthetic waxes, and lanolin derivatives.
- Use of formulations containing excessive amounts of hair conditioning agents of the oily type may cause the hair to have an unpleasant oily appearance and feel.
- Formulations containing certain hair conditioning agents suffer from the additional difficulty that the oily material inhibits sudsing of the shampoo. Most people have come to expect copious lather from their shampoo and are dissatisfied if it is not formed.
- keto acid be generic to encompass not only ketone acids but aldehyde acids as well, i.e., acids containing an oxo-carbonylic group.
- keto acids employed is connection with the instant invention have the general formula:
- keto acids are all well known in the art and may be prepared in a known manner. Suitable keto acids include, but are not limited to, the following:
- fatty imidazolines such as l-coco-5-hydroxyethyl- S-carboxymethyl imidazoline known as Miranol CM
- other similar products made by reacting monocarboxylic fatty acids having chain lengths of to 24 carbon atoms with diethylene triamine and with monohalo monocarboxylic fatty acids having from 2 to 6 carbon atoms
- the fatty beta-alanines such as dodecyl beta-alanine sold under the name dodecyl Deriphat
- betaines such as N- dodecyl-N,N-dimethylaminoacetic acid sold under the name Quatronyx, etc. Mixtures of any two or more of the foregoing may be employed.
- nonionic surface active agents In addition to' ampholytic detergents one may also employ nonionic surface active agents or mixtures thereof.
- useful nonionic surface active agents are the the ethylene oxide ethers of alkyl phenols such as nonylphenol polyoxyethylene ether, the ethylene oxide ethers of fatty alcohols.
- tridecyl alcohol polyoxyethylene ether such as tridecyl alcohol polyoxyethylene ether, the ethylene oxide ethers of alkyl mercaptans such as dodecyl mercaptan polyoxyethylene thioether, the ethylene oxide esters of the fatty acids such as lauric ester of polyethylene glycol and lauric ester of methoxy polyethylene glycol, the ethylene oxide ethers of fatty acid amides, the condensation products of ethylene oxide with partial fatty acid esters of sorbitol. such as the lauric ester of sorbitan polyethylene glycol ether, and other similar materials.
- cationic surface active agents including distearyl dimethyl ammonium chloride, stearyl dimethylbenzyl ammonium chloride, coco dimethylbenzyl ammonium chloride, dicocodimethyl ammonium chloride, cetylpyridinium chloride, cetyltrimethyl ammonium bromide, the stearyl amine salts that are soluble in water such as stearyl amine acetate and stearyl amine hydrochloride, stearyl dimethylamine hydrochloride, distearyl amine hydrochloride, octyl phenoxyethoxyethyl dimethylbenzyl ammonium chloride, decyl pyridinium bromide, the pyridinium chloride derivative of the acetylaminoethyl esters of lauric acid, lauryl trimethyl ammonium chloride, decylamine acetate, lauryl dimethylbenzyl ammonium chlor
- anionic surface active agents such as and including but not limited to the alkyl sulfates such as sodium lauryl sulfate, the fatty taurides such as cocomethyl tauride and tallow methyl tauride, the sulfated monoglycerides, the sulfonated monoglycerides, the alkyl aryl sulfonates, lauryl hydroxy ether lauryl propionate, coconut acid ester of sodium isethionate, dioctyl ester of sodium sulfosuccinic acid, N- octa decyl tetrasodium l,2-dicarboxyl ethyl sulfosuccinate),,.ammonium salt of sulfate ester of an alkyl phenoxy polyoxyethylene ethanol, sodium salt of lauryl polyoxyethylene sulfate, sodium salt of tridecyLether polyoxyethylene sulfate, fatty acid amid
- the instant shampoo compositions also include a solvent such as water, alcohol, isopropanol, glycerine, and the like.
- a solvent such as water, alcohol, isopropanol, glycerine, and the like.
- any of the conventional additives such as preservatives, dyes, pearling agents, perfumes, thickeners, opacifiers andthe like may be included in accordance with conventional compounding practice.
- Fur thermore one may also include UV absorbers, thickeners, formaldehyde and conditioners as are conventionally employed in shampoo compositions.
- compositions of the instant invention may employ in connection with the compositions of the instant invention from about 5 to about 40 percent detergent ingredient.
- the keto acids from aboutO.5 percent to about 10 percent by weight is employedin connection with the compositions.
- keto acids are employed in connection with acidic systems, i.e., surfactant compositions having a pH of from about 3 to about 7, whereupon, in addition to the above aspects, the keto acids also serve to increase the solubility of the detergent systems.
- a surfactant composition was prepared according to the following formulation:
- Triethanolamine lauryl sulfate Alcohol 5.5% Lauryl myristic diethanolamide 5% Phosphoric acid 10% Water
- the pH of the above system was adjusted with sodium hydroxide to a pH of 5.5. 3 grams of the product was mixed with 50 grams of tap water in a 500 milliliter graduated cylinder. The cylinder was stoppered and inverted times and the amount of foam was read in cc's. As a result of this experiment, it was found that the sample had 250 ccs of foam.
- EXAMPLE 2 EXAMPLE 3 The procedure of Example 1 was repeated with the composition of Example 1 with the exception that distilled water was employed instead of tap water. As a result of the experiment the sample was found to produce 225 ccs of foam.
- Example 4 The procedure of Example 2 was repeated with the exception that distilled water was employed instead of tap water. As a result of the experiment the sample was found to produce 275 ccs of foam.
- Example 1 Triethanolamine lauryl sulfate l9% Alcohol 5.5% UV absorber 0.4% Methyl cellulose 0.9% Lauryl myristic diethanolamide 5% Water to l00% The procedure of Example 1 was repeated and as a result the composition was found to produce 325 cos of foam.
- Example 6 The composition of Example 5 was prepared with the exception that 5 percent acetoacetic ethylate was added thereto. As a result of the procedure of Example 5 the composition was found to produce 350 ccs of foam.
- Example 7 The composition of Example 2 was prepared, with the exception that in lieu of 7.3 percent levulinic acid, 9% glyoxylic acid was employed. The procedure of Example 2 was repeated and the sample was found to produce 425 ccs of foam.
- Example 8 The procedure of Example 4 was repeated, with the exception that 5 percent glyoxylic acid was employed instead of 7.3 percent levulinic acid. As a result of the experiment, the sample was found to produce 240 ccs of foam.
- Example 9 The procedure of Example 6 was repeated, with the exception that 2 percent pyruvic acid was employed in lieu of 5 percent acetoethylate. As a result of the experiment, the composition was found to produce 340 ccs of foam.
- a detergent composition consisting essentially of from about 50 to about 94.5 percent water, from about 5 to about 40 percent detergent selected from the group consisting of ampholytic, nonionic, cationic and anionic surfactants and mixtures thereof and from about 0.5 to 10 percent of a keto acid of the formula wherein R is hydrogen or an alkyl group having from 1 to about 20 carbon atoms and n is O to 3.
- keto acid is chosen from the group consisting of levulinic acid, glyoxylic acid and pyruvic acid and mixtures thereof.
- composition of claim 1 wherein said composition has a pH of from about 3 to about 7.
- composition of claim 1 wherein the surfactant is diethanolamine lauryl sulfate.
- a detergent composition consisting essentially of from about 50 to 94.5 percent water, from about 5 to about 40 percent detergent selected from the group consisting of ampholytic, nonionic, cationic and anionic surfactants and mixtures thereof and from about 0.5 to 10 perce'nt of a keto acid of the formula wherein R is hydrogen or a methyl group and n is 0 to 3.
- composition of claim 5 wherein said keto acid is glyoxylic acid.
- composition of claim 5, wherein said keto acid is pyruvic acid.
- keto acid is levulinic acid.
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83525669A | 1969-06-20 | 1969-06-20 | |
| US17785571A | 1971-09-03 | 1971-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3793210A true US3793210A (en) | 1974-02-19 |
Family
ID=26873717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00177855A Expired - Lifetime US3793210A (en) | 1969-06-20 | 1971-09-03 | Keto acid containing compositions |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3793210A (enrdf_load_stackoverflow) |
| FR (1) | FR2046949B1 (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4380549A (en) * | 1975-07-23 | 1983-04-19 | Scott Eugene J Van | Topical treatment of dry skin |
| WO2008046808A1 (de) * | 2006-10-19 | 2008-04-24 | Basf Se | Verwendung von ketosäuren in reinigern zur geruchskontrolle |
| WO2012011892A1 (en) * | 2010-07-19 | 2012-01-26 | Colgate-Palmolive Company | Cleansing composition with decyl and coco glucosides |
| WO2016026710A1 (en) * | 2014-08-21 | 2016-02-25 | Alfa Parf Group S.P.A. | Cosmetic composition for keratin fibres |
| US10865178B2 (en) | 2016-09-30 | 2020-12-15 | Daikin Industries, Ltd. | Carboxylate salt or sulfonate salt, and surfactant |
| US11279814B2 (en) | 2017-03-31 | 2022-03-22 | Daikin Industries, Ltd. | Production method for fluoropolymer, surfactant for polymerization, and use of surfactant |
| US11440875B2 (en) | 2017-03-31 | 2022-09-13 | Daikin Industries, Ltd. | Sulfonic acid, carboxylic acid, and salts thereof |
| US11999681B2 (en) | 2017-03-31 | 2024-06-04 | Daikin Industries, Ltd. | Alkyl sulfate ester or salt of same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129233A (en) * | 1974-09-03 | 1976-03-12 | Kao Corp | Heaarinsuzai soseibutsu |
| GB9026664D0 (en) * | 1990-12-07 | 1991-01-23 | Unilever Plc | Cosmetic composition |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2674580A (en) * | 1950-07-20 | 1954-04-06 | Colgate Palmolive Co | Liquid shampoo |
| US3218234A (en) * | 1962-05-17 | 1965-11-16 | Wilmsmann | Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides |
| US3267136A (en) * | 1963-05-09 | 1966-08-16 | People Of Puerto Rico | Process for producing levulinic acid |
| US3451937A (en) * | 1965-09-23 | 1969-06-24 | Procter & Gamble | Phosphonate compounds |
| US3524877A (en) * | 1966-06-17 | 1970-08-18 | Akademie Der Wissenchaften Zu | Method of producing keto acids |
| US3590122A (en) * | 1967-05-12 | 1971-06-29 | Colgate Palmolive Co | Shampoo composition |
-
1970
- 1970-06-18 FR FR707022562A patent/FR2046949B1/fr not_active Expired
-
1971
- 1971-09-03 US US00177855A patent/US3793210A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2674580A (en) * | 1950-07-20 | 1954-04-06 | Colgate Palmolive Co | Liquid shampoo |
| US3218234A (en) * | 1962-05-17 | 1965-11-16 | Wilmsmann | Treatment of proteinaceous materials with pyruvic acid or glyoxylic acid to remove peroxides |
| US3267136A (en) * | 1963-05-09 | 1966-08-16 | People Of Puerto Rico | Process for producing levulinic acid |
| US3451937A (en) * | 1965-09-23 | 1969-06-24 | Procter & Gamble | Phosphonate compounds |
| US3524877A (en) * | 1966-06-17 | 1970-08-18 | Akademie Der Wissenchaften Zu | Method of producing keto acids |
| US3590122A (en) * | 1967-05-12 | 1971-06-29 | Colgate Palmolive Co | Shampoo composition |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4380549A (en) * | 1975-07-23 | 1983-04-19 | Scott Eugene J Van | Topical treatment of dry skin |
| WO2008046808A1 (de) * | 2006-10-19 | 2008-04-24 | Basf Se | Verwendung von ketosäuren in reinigern zur geruchskontrolle |
| WO2012011892A1 (en) * | 2010-07-19 | 2012-01-26 | Colgate-Palmolive Company | Cleansing composition with decyl and coco glucosides |
| US8877184B2 (en) | 2010-07-19 | 2014-11-04 | Colgate-Palmolive Company | Cleaning composition with decyl and coco glucosides |
| US9504635B2 (en) | 2010-07-19 | 2016-11-29 | Colgate-Palmolive Company | Composition containing 4-oxovaleric acid and leuconostoc/radish root ferment filtrat |
| EP3384896A1 (en) * | 2010-07-19 | 2018-10-10 | Colgate-Palmolive Company | Cleansing composition with 4-oxovaleric acid and leuconostoc/radish root ferment filtrate |
| WO2016026710A1 (en) * | 2014-08-21 | 2016-02-25 | Alfa Parf Group S.P.A. | Cosmetic composition for keratin fibres |
| US10865178B2 (en) | 2016-09-30 | 2020-12-15 | Daikin Industries, Ltd. | Carboxylate salt or sulfonate salt, and surfactant |
| US11279814B2 (en) | 2017-03-31 | 2022-03-22 | Daikin Industries, Ltd. | Production method for fluoropolymer, surfactant for polymerization, and use of surfactant |
| US11440875B2 (en) | 2017-03-31 | 2022-09-13 | Daikin Industries, Ltd. | Sulfonic acid, carboxylic acid, and salts thereof |
| US11999681B2 (en) | 2017-03-31 | 2024-06-04 | Daikin Industries, Ltd. | Alkyl sulfate ester or salt of same |
| US12404387B2 (en) | 2017-03-31 | 2025-09-02 | Daikin Industries, Ltd. | Production method for fluoropolymer, surfactant for polymerization, and use of surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2046949A1 (enrdf_load_stackoverflow) | 1971-03-12 |
| FR2046949B1 (enrdf_load_stackoverflow) | 1973-01-12 |
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