US3642429A - Cosmetic composition for treating hair - Google Patents
Cosmetic composition for treating hair Download PDFInfo
- Publication number
- US3642429A US3642429A US770089A US3642429DA US3642429A US 3642429 A US3642429 A US 3642429A US 770089 A US770089 A US 770089A US 3642429D A US3642429D A US 3642429DA US 3642429 A US3642429 A US 3642429A
- Authority
- US
- United States
- Prior art keywords
- hair
- formula
- compound
- composition
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 239000002537 cosmetic Substances 0.000 title abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000003377 acid catalyst Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229940099500 cystamine Drugs 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- ODJCKHUIAVVZBX-UHFFFAOYSA-N 3-methyl-1,1-dipropylurea Chemical compound CCCN(CCC)C(=O)NC ODJCKHUIAVVZBX-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims description 5
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 4
- ALAKPALWEMXPRD-UHFFFAOYSA-N 1-(diethylamino)-1-ethylurea Chemical compound C(C)N(CC)N(C(=O)N)CC ALAKPALWEMXPRD-UHFFFAOYSA-N 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- RJPIWRMCRBSFHG-UHFFFAOYSA-N [I-].[NH4+].C(C)N(C(N(CC)C)=O)CC Chemical compound [I-].[NH4+].C(C)N(C(N(CC)C)=O)CC RJPIWRMCRBSFHG-UHFFFAOYSA-N 0.000 claims description 4
- XLCDSNFXNIFAJK-UHFFFAOYSA-N 2-sulfanylethylurea Chemical compound NC(=O)NCCS XLCDSNFXNIFAJK-UHFFFAOYSA-N 0.000 claims description 3
- FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- SPGJJOMYARUEPF-UHFFFAOYSA-N CCCN(C)C(N(C)CCC)=O.N Chemical compound CCCN(C)C(N(C)CCC)=O.N SPGJJOMYARUEPF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- -1 methylol amine Chemical class 0.000 abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 14
- 150000001412 amines Chemical group 0.000 abstract description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
- 239000012039 electrophile Substances 0.000 abstract description 3
- 125000003636 chemical group Chemical group 0.000 abstract 1
- 102000011782 Keratins Human genes 0.000 description 8
- 108010076876 Keratins Proteins 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000490 cosmetic additive Substances 0.000 description 4
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 4
- 229950005308 oxymethurea Drugs 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ORGWCTHQVYSUNL-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)thiourea Chemical compound OCNC(=S)NCO ORGWCTHQVYSUNL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960001040 ammonium chloride Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAGFPFWZCJWYRP-UHFFFAOYSA-N 1,1-bis(hydroxymethyl)urea Chemical compound NC(=O)N(CO)CO QAGFPFWZCJWYRP-UHFFFAOYSA-N 0.000 description 2
- QXYJLKUVMPXXKA-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)imidazolidine-2-thione Chemical compound OCN1CCN(CO)C1=S QXYJLKUVMPXXKA-UHFFFAOYSA-N 0.000 description 2
- MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 2
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940107816 ammonium iodide Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000002228 disulfide group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- KTKDYVVUGTXLJK-UHFFFAOYSA-N 1,1-dipropylurea Chemical compound CCCN(C(N)=O)CCC KTKDYVVUGTXLJK-UHFFFAOYSA-N 0.000 description 1
- XKALZGSIEJZJCZ-UHFFFAOYSA-N 1,3-bis(methoxymethyl)urea Chemical compound COCNC(=O)NCOC XKALZGSIEJZJCZ-UHFFFAOYSA-N 0.000 description 1
- QEBHSIIPSMAHJR-UHFFFAOYSA-N 1,3-dimethyl-1,3-dipropylurea Chemical compound CCCN(C)C(=O)N(C)CCC QEBHSIIPSMAHJR-UHFFFAOYSA-N 0.000 description 1
- IUWCYUPLASEVJO-UHFFFAOYSA-N 1-bromo-n,n-diethylethanamine;hydrobromide Chemical compound Br.CCN(CC)C(C)Br IUWCYUPLASEVJO-UHFFFAOYSA-N 0.000 description 1
- NULDEVQACXJZLL-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethylazanium;chloride Chemical compound Cl.NCCSSCCN NULDEVQACXJZLL-UHFFFAOYSA-N 0.000 description 1
- BAEWLQWSDPXZDM-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyldisulfanyl]-n,n-dimethylethanamine Chemical compound CN(C)CCSSCCN(C)C BAEWLQWSDPXZDM-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- BITBMHVXCILUEX-UHFFFAOYSA-N 2-chloroethylurea Chemical compound NC(=O)NCCCl BITBMHVXCILUEX-UHFFFAOYSA-N 0.000 description 1
- HYTCSCBDAFJMIP-UHFFFAOYSA-N 3-ethyl-1,1-dimethylurea Chemical compound CCNC(=O)N(C)C HYTCSCBDAFJMIP-UHFFFAOYSA-N 0.000 description 1
- DNPHEDNKXRMPAX-UHFFFAOYSA-N 3-hydroxypropylurea Chemical compound NC(=O)NCCCO DNPHEDNKXRMPAX-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NXYBSSIUELDEGF-UHFFFAOYSA-N Cl.Cl.CN(CCC)CCC Chemical compound Cl.Cl.CN(CCC)CCC NXYBSSIUELDEGF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- CALBDOUFMLLGQH-UHFFFAOYSA-N hydroxymethylthiourea Chemical compound NC(=S)NCO CALBDOUFMLLGQH-UHFFFAOYSA-N 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
- A61K8/42—Amides
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- 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
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61Q5/04—Preparations for permanent waving or straightening 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
Definitions
- a cosmetic composition for treating hair comprising an electrophile methylol amine and a urein compound, one or both of which contain a chemical group-which has cosmetic properties; and a method of treating hair with this composition.
- Y(NH(l'TNHz)n .s .a.A Y-. X in which n 1 or 2, X is O, S or NH and Y is a disulfide, carboxylic acid, tertiary or quaternary amine or SH group which has cosmetic properties.
- This invention relates to a cosmetic composition which ,makes it possible to improve the condition of human hairand to impart thereto certain properties which are useful when it is to be subjected to a subsequent cosmetic treatment.
- compositions comprising methylol products which are more stable than dimethylolurea and dimethylolthiourea be used, which products yield excellent results due to polymerization in'the keratin chain and condensation of these compounds on the reactive groups of the keratin, thereby in practice imparting to the treated hair greater strength, an improved appearance and, in general, attractive cosmetic properties.
- This phenomenon is particularly valuable when the compound of the urein type contains a cosmetic component attached to the nitrogen which is finally embedded inside the hair when the methylol compounds are polymerized in the keratin in the presence of these particular urein compounds.
- R represents either hydrogen, or a lower alkyl radical
- E represents a radical which is sufficiently electrophile to assure that the entire g'rou molecule
- E is selected from among the following groups:
- urein-type compounds which may be used in the cosmetic compositions according to the invention are:
- the number of urea groups carried by the urein-type compound lies between 0.2 and 3 times and preferably from 0.5 to 1.0 times the number of hydroxyrnethyl or alkoxy methyl groups carried by the methylol compound.
- the composition also contains an acid catalyst, which may bea rnineralor organic acid used in the cosmetic fieldor a salthaving anacid reaction.
- an acid catalyst which may be a rnineralor organic acid used in the cosmetic fieldor a salthaving anacid reaction.
- composition according to the invention may take the form of an aqueous or hydroalcoholic solution and serve as a setting lotion which may comprise any additives conventionallyincluded in such lotions
- the composition according to the'invention may also .take the form of a gel or cream, or be packaged in aerosolf'orm.
- composition according to the invention may also contain any ingredients conventionally used incosmetics, such as dyes, perfumes, surface-active agents, swelling agents, resins, etc.
- the composition may be packaged in two phases, a solid phase containing the methylol compounds, and the urein-type compounds, and a liquid phase which is an aqueous or hydroalcoholic solution, which may contain conventional cosmetic additives and/or an acid catalyst.
- the solid phase contains only the methylol compounds, and the urein-type compounds are in aqueous or hydroalcoholic solution.
- the cosmetic composition according to the invention is prepared at the moment of use by dissolving the solid phase in the liquid phase. This rnethod of packaging makes it possible to avoid the premature polycondensations which may take place during prolonged storage of the composition.
- the solid phase or the aqueous phase of the cosmetic composition packaged in this manner may also contain a salt of sulfurous acid, such as sodium metabisultite.
- a further object of the present invention is to provide a method of treating hair characterized by the fact that the hair is impregnated with the above-described composition, and then dried by heating, after having first been rinsed.
- the cosmetic composition does not itself contain the acid catalyst necessary to bring about polycondensation of the methylol compounds and the urein-type compounds in the keratinic fiber, and this acid catalyst is instead applied to the hair either before or after the composition according to the invention.
- lt is a further object of the present invention to provide the new article of manufacture .which consists of a compound responding to the following formula:
- X represents hydrogen, sulfur, or an NH radical
- Y is a. radical comprising a chemical-functionwhich enables it to serve a cosmeticrpurpose such, for example, as a disulfide function, a carboxylic acid function, a tertiaryor .quatemary amine function, a .fatty chain, or an SH function.
- the present invention has ,as its particular object the production of a new-article of manufactureconsisting of a compound selected from thegroup consisting of:
- N-methyl-dipropylurea (dimethyl-copra-ethylurea)-ammonium-chloride, N,N-carbamyl cystamine, N-carbamyl-cystamine hydrochloride, N,N'-(dimethyl-ethylurea)- cystamine dichloride, (diethyl-methyl-ethylurea)-ammonium iodide, diethylamino ethylurea (dimethyl, .dipropylurea) ammonium methosulfate,and N-carbamyl cysteamine.
- a further object of the present invention is to provide a new method of preparing urein-type compounds as described above, characterizedby the fact that a cyanate or an alkaline thiocyanate .is reacted with amine compounds having a Y- grouprepresenting the cosmetic additive in question attached to the nitrogen.
- the amine which carries the cosmetic additive attached to its nitrogen atom is reacted .with urea, to produce the corresponding urein by elimination of ammonia.
- a tertiary amine having a cosmetic additive attached to its nitrogen atom is reactedwith a halogenoalkylurea.
- EXAMPLE 1 An aqueous solution of the following composition is applied to natural hair which has first been washed and dried:
- the hair is then set in aconventional manner by winding it up on rollers and drying it under a hood at a temperature of 45 -50 C. This attaches to the keratin of the hair an acid compound having the following statistical formula:
- This operation permits the attachment to the keratin of a compound of the disulfide typewhich is soluble in reducing media and has substantially the following composition:
- n lies between 0.5 and l inclusive.
- the hair is strengthened and the set holds well and is sprin- 8% Moreover, the presence of artificial disulfide bonds in the kcrutinic libcr makes it possible to subsequently permanently wave or bleach the hair under improved conditions.
- the hair is then set in a conventional manner, keeping it for about 30 minutes at a temperature between 45 and 50 C.
- monomethylolurea 8 g. (dimethyl-copra-ethylurea)-ammonium chloride 2 g. acetic acid q.s.p. pH 3 water q.s.p. I00 cc.
- EXAMPLE 5 Preparation of (dimethyl-dipropylurea)-amrnonium methosulfate
- the first step is to prepare N-methyl-dipropylurea by reacting potassium cyanate with N-methyl-dipropylamine dihydrochloride in stoichiometric proportions. The reaction is carried out in aqueous solution at a temperature of 90 C. for 2 hours.
- the product is dried by evaporation and then extracted with hot absolute ethanol.
- the result is a white powder titrating 95 a temperature between percent of the theoretical amount of total ry amines.
- N-methyl-dipropylurea is suspended in l liter of absolute ethanol.
- a stoichiometric quantity, or a slight excess, of methyl sulfate is added slowly, while stirring.
- the resulting quaternary compound separates from the alcoholic layer, in the form of a thick oil which is vacuum dried and may be purified by washing with ether. The yield is practically quantitative'.
- the resulting paste is washed with 450 cc. of chloroform, and again dried on phosphoric anhydride.
- the final result is a 98 percent yield of a solid white product titrating about percent of the theoretical value of disulfide and ionized chloride.
- a process for treating human hair which comprises applying to said hair a composition containing in a solvent selected from the group consisting of water and'hydroalcoholic solution:
- X is selected from the group consisting of O, S and NH
- n is l or 2 and when n is 1, Y is selected from the group conand when n is 2, Y is selected from the group consisting of *(CH2)al T( 2)a-, 2)2 H2)Z CH CH said composition containing said compound (I) in a concentration ranging from 0.5 to 12 percent by weight, polycondensing said compound and said urein compound on said hair in the presence of an acid catalyst in amounts sufficient to polycondense said compound and said urein compound, rinsing the hair and then drying the same.
- said acid catalyst is selected from the group consisting of acetic acid, phosphoric acid and hydrochloric acid.
- said urein compound is r a compound having the formula N-carbamyl N-carbamyl cysteamine, cystamine hydrochloride, N,N dimethyl-ethylurea )cystamine dichloride, (diethyl-methyl-ethylurea )-ammonium iodide, diethylamino ethylurea and (dimethyl-dipropylurea)-ammonium methosulfate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU54741 | 1967-10-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3642429A true US3642429A (en) | 1972-02-15 |
Family
ID=19725387
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US770089A Expired - Lifetime US3642429A (en) | 1967-10-26 | 1968-10-23 | Cosmetic composition for treating hair |
Country Status (10)
Country | Link |
---|---|
US (1) | US3642429A (xx) |
AT (1) | AT295752B (xx) |
BE (1) | BE722886A (xx) |
CA (1) | CA933094A (xx) |
CH (1) | CH520503A (xx) |
FR (1) | FR1598172A (xx) |
GB (1) | GB1253235A (xx) |
IT (1) | IT1036013B (xx) |
LU (1) | LU54741A1 (xx) |
NL (1) | NL156598B (xx) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001006994A1 (en) * | 1999-07-23 | 2001-02-01 | Unilever Plc | Method of reducing colour loss from dyed hair using organic amino compounds |
US20090056745A1 (en) * | 2007-08-27 | 2009-03-05 | Applied Materials, Inc. | Wet clean process for recovery of anodized chamber parts |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU461954B2 (en) * | 1970-11-16 | 1975-06-12 | Colgate-Palmolive Company | Cosmetic compositions |
CA1175609A (fr) * | 1980-06-06 | 1984-10-09 | Gerard Lang | Compositions contenant des derives bis-ammonium quaternaire destinees au traitement de matieres keratiniques et de matieres textiles naturelles non- keratiniques ou synthetiques, procede de traitement utilisant lesdites compositions et composes utilises |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3232933A (en) * | 1960-04-30 | 1966-02-01 | Dehydag Gmbh | 1-thiocarbamyl-2-imidazolidinethiones and a process for their preparation |
US3349000A (en) * | 1963-01-24 | 1967-10-24 | Joos Bernhard | Process for treating human nails and hair with dimethylol thiourea compositions |
US3534135A (en) * | 1965-12-23 | 1970-10-13 | Wella Ag | Method for setting hair with dithiourea and derivatives thereof |
-
1967
- 1967-10-26 LU LU54741D patent/LU54741A1/xx unknown
-
1968
- 1968-10-23 US US770089A patent/US3642429A/en not_active Expired - Lifetime
- 1968-10-24 NL NL6815223.A patent/NL156598B/xx not_active IP Right Cessation
- 1968-10-25 BE BE722886D patent/BE722886A/xx not_active Expired
- 1968-10-25 AT AT1043268A patent/AT295752B/de not_active IP Right Cessation
- 1968-10-25 GB GB1253235D patent/GB1253235A/en not_active Expired
- 1968-10-25 IT IT53629/68A patent/IT1036013B/it active
- 1968-10-25 CA CA033604A patent/CA933094A/en not_active Expired
- 1968-10-25 CH CH1598868A patent/CH520503A/fr not_active IP Right Cessation
- 1968-10-25 FR FR1598172D patent/FR1598172A/fr not_active Expired
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3232933A (en) * | 1960-04-30 | 1966-02-01 | Dehydag Gmbh | 1-thiocarbamyl-2-imidazolidinethiones and a process for their preparation |
US3349000A (en) * | 1963-01-24 | 1967-10-24 | Joos Bernhard | Process for treating human nails and hair with dimethylol thiourea compositions |
US3534135A (en) * | 1965-12-23 | 1970-10-13 | Wella Ag | Method for setting hair with dithiourea and derivatives thereof |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001006994A1 (en) * | 1999-07-23 | 2001-02-01 | Unilever Plc | Method of reducing colour loss from dyed hair using organic amino compounds |
US6551361B1 (en) | 1999-07-23 | 2003-04-22 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Method of hair treatment using organic amino compounds |
US20090056745A1 (en) * | 2007-08-27 | 2009-03-05 | Applied Materials, Inc. | Wet clean process for recovery of anodized chamber parts |
Also Published As
Publication number | Publication date |
---|---|
DE1803709A1 (de) | 1969-06-04 |
IT1036013B (it) | 1979-10-30 |
AT295752B (de) | 1972-01-25 |
DE1803709B2 (de) | 1977-07-07 |
CH520503A (fr) | 1972-03-31 |
CA933094A (en) | 1973-09-04 |
GB1253235A (xx) | 1971-11-10 |
FR1598172A (xx) | 1970-07-06 |
NL6815223A (xx) | 1969-04-29 |
LU54741A1 (xx) | 1969-06-27 |
BE722886A (xx) | 1969-04-25 |
NL156598B (nl) | 1978-05-16 |
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