CN102245714B - 聚合物毛发用染料 - Google Patents
聚合物毛发用染料 Download PDFInfo
- Publication number
- CN102245714B CN102245714B CN200980150408.4A CN200980150408A CN102245714B CN 102245714 B CN102245714 B CN 102245714B CN 200980150408 A CN200980150408 A CN 200980150408A CN 102245714 B CN102245714 B CN 102245714B
- Authority
- CN
- China
- Prior art keywords
- group
- dyestuff
- formula
- dye
- hair
- 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 - Fee Related
Links
- 239000000118 hair dye Substances 0.000 title description 9
- 239000000975 dye Substances 0.000 claims abstract description 141
- 210000004209 hair Anatomy 0.000 claims abstract description 53
- 238000004043 dyeing Methods 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims description 63
- -1 bisulfate ion Chemical class 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 30
- 239000000835 fiber Substances 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 20
- 108010039918 Polylysine Proteins 0.000 claims description 13
- 239000011368 organic material Substances 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 229920000656 polylysine Polymers 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- 239000002453 shampoo Substances 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
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- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 3
- 229930182817 methionine Natural products 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
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- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 108010020346 Polyglutamic Acid Proteins 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- 239000006035 Tryptophane Substances 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960002989 glutamic acid Drugs 0.000 claims description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 108010052780 polyasparagine Proteins 0.000 claims description 2
- 229920002643 polyglutamic acid Polymers 0.000 claims description 2
- 229960002429 proline Drugs 0.000 claims description 2
- 229960001153 serine Drugs 0.000 claims description 2
- 229960002898 threonine Drugs 0.000 claims description 2
- 229960004799 tryptophan Drugs 0.000 claims description 2
- 229960004441 tyrosine Drugs 0.000 claims description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 6
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 abstract description 9
- 108010038807 Oligopeptides Proteins 0.000 abstract description 3
- 102000015636 Oligopeptides Human genes 0.000 abstract description 3
- 229920001184 polypeptide Polymers 0.000 abstract description 3
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 3
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 3
- 235000001014 amino acid Nutrition 0.000 abstract description 2
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
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- 239000003795 chemical substances by application Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
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- 238000006243 chemical reaction Methods 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000006193 diazotization reaction Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 241001080929 Zeugopterus punctatus Species 0.000 description 8
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- 239000003513 alkali Substances 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
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- 238000004061 bleaching Methods 0.000 description 5
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- 238000006471 dimerization reaction Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- LGWXIBBJZQOXSO-UHFFFAOYSA-L disodium 5-acetamido-4-hydroxy-3-[(2-methylphenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1C LGWXIBBJZQOXSO-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 210000000720 eyelash Anatomy 0.000 description 1
- 235000019240 fast green FCF Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 231100000640 hair analysis Toxicity 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 230000003806 hair structure Effects 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- YWOITFUKFOYODT-UHFFFAOYSA-N methanol;sodium Chemical compound [Na].OC YWOITFUKFOYODT-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 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
- 239000004530 micro-emulsion Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 235000011929 mousse 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
- 229940115453 n,n-bis(2-hydroxyethyl)-p-phenylenediamine sulfate Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004999 nitroaryl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229940097156 peroxyl Drugs 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 235000020245 plant milk Nutrition 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- DJDYMAHXZBQZKH-UHFFFAOYSA-M sodium;1-amino-4-(cyclohexylamino)-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1CCCCC1 DJDYMAHXZBQZKH-UHFFFAOYSA-M 0.000 description 1
- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- NWKBFCIAPOSTKG-UHFFFAOYSA-M trimethyl-[3-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC([N+](C)(C)C)=C1 NWKBFCIAPOSTKG-UHFFFAOYSA-M 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
-
- 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
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
- A61K2800/4322—Direct dyes in preparations for temporarily coloring the hair further containing an oxidizing agent
Abstract
聚合物染料,包含选自具有至少一种共价键合的阳离子染料的天然或合成氨基酸的寡肽和多肽。在人类毛发上使用这些染料时得到非常好的染色结果。
Description
本发明涉及新型聚合物染料及含有这些化合物的组合物,其制备方法以及其用于有机材料如含角蛋白的纤维、羊毛、皮革、丝、纤维素或聚酰胺染色的用途。
众所周知阳离子化合物对带负电的毛发具有良好的亲合力。这些特征已被用来使毛发与小分子及聚合物接触。
已公开将许多阳离子聚合物染料用作人类毛发的着色剂,例如US4,228,259;US 4,182,612或FR 2 456 764。这些参考文献教导了聚合物结构部分具有阳离子电荷。
惊讶地发现采用其中阳离子电荷位于染料结构部分中的聚合物毛发用染料获得了非常良好的染色结果。
更具体地,惊讶地发现采用其中阳离子电荷位于染料结构部分中的寡肽和多肽获得了非常良好的染色结果和耐洗坚牢度。
因此,本发明涉及包含选自含至少一种共价键合的阳离子染料的天然或合成氨基酸的寡肽和多肽的聚合物染料。
优选这些聚合物染料对应于下式(1a)和(1b):
其中:
A和B相互独立地为选自天然或合成的氨基羧酸的聚合物骨架;
X1和X2相互独立地为选自以下基团的连接基团:-C1-C30亚烷基-、-C2-C12亚链烯基-或-C6-C10亚芳基-,其被一个或多于一个以下基团间隔和/或在一端或两端封端:-O-、-S-、-N-、-N=、-N(R5)-、-S(O)-、-SO2-、-(CH2CH2-O)1-5-、-(CH2CH2CH2-O)1-5-、-C(O)-、-C(O)O-、-OCO-、-CON(R1)-、-C(NR1R2)2-、-(R1)NC(O)-、-C(S)R1-或或任选包含至少一个杂原子且任选取代的饱和或不饱和、稠合或非稠合芳族或非芳族(杂环)二价基团;包含至少一个杂原子的饱和或不饱和、稠合或非稠合芳族或非芳族二价基团,其任选被C1-C30烷基、C1-C30烷氧基、C2-C12链烯基、C5-C10芳基、C5-C10环烷基、C1-C10烷基(C5-C10亚芳基)、羟基或卤素取代;直接键;或式(1c)-(T)t(Z)-的二价基团,其中:
T为-C1-C12亚烷基;-C2-C12亚链烯基-;-C(O)-;-(CH2CH2-O)1-5-;
-(CH2CH2CH2-O)1-5-;-C(O)O-;-OC(O)-;-N(R3)-;-CON(R3)-;
-(R3)NC(O)-;-O-;-S-;-S(O)-;-S(O)2-;-S(O)2N(R3)-或-N+(R3)(R4)-;
Z为式(1d)的双基;
R1、R2、R3、R4和R5相互独立地为氢;未取代或取代、直链或支化、单环或多环、间隔或未间隔的C1-C14烷基;C1-C14烷氧基;C2-C14链烯基;C1-C6烷基氨基;C6-C10芳基;C6-C10芳基-C1-C10烷基;C6-C10芳基-C1-C10烷氧基;或C5-C10烷基(C5-C10芳基);
Ra为氢;C1-C6烷基;C1-C6烷氧基;C1-C6烷基氨基;C6-C10芳氧基;C6-C10-芳基氨基;SO2R3;氯或氟;
Y为Ra;Y1 a+或Y2 b+;
a和b相互独立地为1、2或3;
t为0或1;
Y1和Y2相互独立地为有机染料残基或氢;其中Y1和Y2中至少一个为有机染料残基;
An1和An2相互独立地为阴离子;
a和b相互独立地为1-3的数;
m为0-5000的数;
n为0-5000的数;和
p为1-5000的数;
其中m+n+p之和≥3。
优选如下的式(1a)或(1b)的染料,其中:
A和B相互独立地为选自天然或合成的氨基羧酸的聚合物骨架;
X1和X2相互独立地为选自以下基团的连接基团:-C1-C30亚烷基-和-C2-C12亚链烯基-,其被一个或多于一个以下基团间隔和/或在一端或两端封端:-S-、-N-、-N=、-N(R5)-、-S(O)-、-SO2-、-(CH2CH2-O)1-5-、-(CH2CH2CH2-O)1-5-、-C(O)-、-C(O)O-、-OCO-、-CON(R1)-、-C(NR1R2)2-、-(R1)NC(O)-、-C(S)R1-;或任选包含至少一个杂原子且任选取代的饱和或不饱和、稠合或非稠合芳族或非芳族(杂环)二价基团;包含至少一个杂原子的饱和或不饱和的、稠合或非稠合芳族或非芳族二价基团,其任选由C1-C30烷基、C1-C30烷氧基、C2-C12链烯基、C5-C10芳基、C5-C10环烷基、C1-C10烷基(C5-C10亚芳基)、羟基或卤素取代;直接键;或式(1c)-(T)t(Z)-的二价基团,其中
T为-C1-C12亚烷基;-C2-C12亚链烯基-;-C(O)-;-(CH2CH2-O)1-5-;
-(CH2CH2CH2-O)1-5-;-C(O)O-;-OC(O)-;-N(R3)-;-CON(R3)-;
-(R3)NC(O)-;-O-;-S-;-S(O)-;-S(O)2-;-S(O)2N(R3)-或-N+(R3)(R4)-;
Z为式(1d)的双基;
R1、R2、R3、R4和R5相互独立地为氢;未取代或取代、直链或支化、单环或多环、间隔或未间隔的C1-C14烷基;C1-C14烷氧基;C2-C14链烯基;C1-C6烷基氨基;C6-C10芳基;C6-C10芳基-C1-C10烷基;C6-C10芳基-C1-C10烷氧基或C5-C10烷基(C5-C10芳基);
Ra为氢;C1-C6烷基;C1-C6烷氧基;C1-C6烷基氨基;C6-C10芳氧基;C6-C10-芳基氨基;SO2R3;氯或氟;
Y为Ra;Y1 a+或Y2 b+;
a和b相互独立地为1、2或3;
t为0或1;
Y1和Y2相互独立地为有机染料残基或氢;其中Y1和Y2中至少一个为有机染料残基;
An1和An2相互独立地为阴离子;
a和b相互独立地为1-3的数;
m为0-5000的数;
n为0-5000的数;和
p为1-5000的数;
其中m+n+p之和≥3。
C1-C14烷基例如为甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、环戊基、环己基、正己基、正辛基、1,1′,3,3′-四甲基丁基或2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基或十四烷基。
C2-C14链烯基例如为烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基-丁-2-烯基、正辛-2-烯基、正十二-2-烯基、异十二烯基、正十二-2-烯基或正十八-4-烯基。
C6-C10芳基例如为苯基或萘基。
C1-C30亚烷基例如为亚甲基、亚乙基、亚丙基、亚异丙基、亚正丁基、亚仲丁基、亚叔丁基、亚正戊基、2-亚戊基、3-亚戊基、2,2′-二甲基亚丙基、亚环戊基、亚环己基、亚正己基、亚正辛基、1,1′,3,3′-四甲基亚丁基、2-乙基亚己基、九亚甲基、十亚甲基、十三亚甲基、十四亚甲基、十五亚甲基、十六亚甲基、十七亚甲基、十八亚甲基、十九亚甲基或二十亚甲基。
“阴离子”指例如有机或无机阴离子,例如卤离子,优选为氯离子及氟离子,硫酸根、硫酸氢根、磷酸根离子、四氟化硼离子、碳酸根、碳酸氢根、草酸根或C1-C8烷基硫酸根,特别是甲基硫酸根或乙基硫酸根;阴离子还指乳酸根、甲酸根、乙酸根、丙酸根或配阴离子,例如氯化锌复盐。
在式(1a)和(1b)中,优选:
Y1和Y2相互独立地选自蒽醌、吖啶、偶氮、氮杂次甲基(azamethine)、联亚氨基次甲基、三苯基甲烷、苯并二呋喃酮、香豆素、二酮基吡咯并吡咯、二嗪、二苯基甲烷、甲(formazane)、靛类靛酚、萘二甲酰亚胺、萘醌、硝基芳基、部花青、次甲基、嗪、紫环酮、苝、芘醌、酞菁、吩嗪、醌亚胺、喹吖啶酮、喹酞酮、苯乙烯基、茋、呫吨、噻嗪和噻吨染料。
更优选Y1和Y2相互独立地选自偶氮、偶氮甲碱、联亚氨基次甲基、蒽醌、部花青、次甲基、嗪和苯乙烯基染料。
最优选Y1和Y2具有相同含义。
在式(1a)和(1b)中聚合物骨架(A和B)和有机染料残基(Y1和Y2)优选均具有选自亲电子基团或亲核基团的官能团,所述亲电子基团选自卤离子、甲苯磺酰化物、甲磺酰化物、甲氧基、羧酸、羧酰氯、磺酰氯、环氧化物、酐;所述亲核基团选自胺、胍、羟基和硫醇。
甚至更优选如下式(1a)和(1b)的染料,其中聚合物骨架(A和B)选自组氨酸、精氨酸、半胱氨酸、谷氨酰胺、谷氨酸、赖氨酸、天冬酰胺、丝氨酸、酪氨酸、苏氨酸、色氨酸和脯氨酸。
最优选的聚合物骨架为聚赖氨酸、聚天冬氨酸、聚谷氨酸和聚天冬酰胺。
聚合物染料的分子量优选为400-50000。
最优选为用X1-(Y1 a+)染料结构部分在α和/或ε位改性的聚赖氨酸,其例如对应于下式:
其中
X1、Y1、m、n和a如式(1a)和(1b)中所定义。
该聚合物骨架的部分氨基官能团也可能保持未反应的状态也是可能的。
式(2)的聚合物染料通过如下方法获得:
1.由赖氨酸合成聚赖氨酸,和
2.使聚赖氨酸与式(Y1 a+)-X1-Z的染料反应。Y1.、Z为反应性离去基团如卤离子、甲氧基、甲苯磺酸根:
反应可在溶剂中进行,如水;醇如甲醇、乙醇、2-丙醇或丁醇;腈如乙腈或丙腈;酰胺如二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮;氯化烃如氯仿、氯苯或三氯乙烯;或其他溶剂如二甲亚砜。
通常在起始化合物的混合过程中温度为0-200℃,优选20-110℃。
反应时间通常取决于起始化合物的活性、选择的反应温度和所需转化率。选择的反应时间通常为3小时至7天。
选择的反应压力通常为0.1-10巴,尤其是0.2-3.0巴,更尤其是大气压。
可能需要在催化剂存在下进行各化合物的反应。
合适的催化剂例如为碱金属或过渡金属的C1-C6醇盐如钠、钾或锂的C1-C6醇盐,优选甲醇钠、甲醇钾或甲醇锂,或乙醇钠、乙醇钾或乙醇锂;或仲胺或叔胺如喹啉环、哌啶、N-甲基哌啶、吡啶、三甲基胺、二甲基胺、二乙基胺、三乙基胺、三辛基胺、1,4-二氮杂二环[2.2.2]辛烷、喹啉环、N-甲基哌啶;或碱金属乙酸盐,例如乙酸钠、乙酸钾或乙酸锂。
式(2a)的染料与聚赖氨酸单体的摩尔比通常选择为0.1∶1-3∶1,尤其为0.1∶1-1.5∶1。
根据本发明方法制备的产物可有利地进行后处理和分离,且如果需要的话,提纯。
通常后处理开始于将反应混合物的温度降低至5-80℃,尤其是20-50℃。
在几个小时内缓慢地降低温度可能是有利的。
一般地,通常将反应产物滤出,然后用水、溶剂或盐溶液洗涤并随后干燥。
过滤通常在标准过滤设备,例如瓷漏斗、压滤机、加压吸滤器,优选在真空中进行。
干燥温度取决于施加的压力。干燥通常在50-200毫巴的真空下进行。干燥通常在40-90℃的温度下进行。
在分离后,有利地将该产物通过再结晶而提纯。有机溶剂和溶剂混合物对再结晶是合适的。
本发明式(1a)和(1b)染料适于染色有机材料,例如含角蛋白的纤维、羊毛、皮革、丝、纤维素或聚酰胺、棉或尼龙,优选人类毛发,包括身体毛发像眉毛、睫毛、阴毛、胸毛、腋毛及胡须。也可用本发明的毛发染料将动物毛发染色。
所获得的染色物的特征是其色调深度及其良好的耐洗坚牢度性质,例如耐光、耐洗发剂及耐磨擦坚牢度。
通常合成基毛发染色剂可分成三种:
-暂时性染色剂
-半持久性染色剂,及
-持久性染色剂。
染料色调的多样性可通过与其他染料的组合而增加。
因此,本发明式(1a)和(1b)染料可与相同或其他染料类别的染料组合,尤其是与直接染料、氧化染料的组合;偶合剂化合物与重氮化化合物或封闭的重氮化化合物的染料前体组合;和/或阳离子活性染料。
直接染料为天然来源或可合成制备。它们为未荷电的、阳离子的或阴离子的,例如酸性染料。
式(1a)和(1b)染料可与至少一种不同于式(1a)和(1b)染料的单直接染料组合使用。
直接染料的实例描述于由Ch.Culnan,H.Maibach所编辑的“Dermatology”,Verlag Marcel Dekker Inc.,New York,Basle,1986,第7卷,Ch.Zviak,The Science of Hair Care,第7章,第248-250页中以及可以磁盘形式从Bundesver-band der deutschen Industrie-undHandelsunternehmen für Arzneimittel,Reformwaren unde.V.,Mannheim获得的1996年由The EuropeanCommission所发表的“Inventar der Kosmetikrohstoffe”中。
更优选的可用于与至少一种式(1a)和(1b)的单染料,尤其是半持久性染料组合的直接染料为:2-氨基-3-硝基酚、2-氨基-4-羟乙基氨基茴香醚硫酸酯、2-氨基-6-氯-4-硝基酚、2-氯-5-硝基-N-羟亚乙基对苯二胺、2-羟乙基苦氨酸、2,6-二氨基-3-((吡啶-3-基)-偶氮)吡啶、2-硝基-5-甘油基甲基苯胺、3-甲基氨基-4-硝基苯氧基乙醇、4-氨基-2-硝基二亚苯基胺-2’-甲酸、6-硝基-1,2,3,4,-四氢喹喔啉、4-N-乙基-1,4-二(2’-羟乙基氨基-2-硝基苯盐酸盐、1-甲基-3-硝基-4-(2’-羟乙基)氨基苯、3-硝基对羟基乙基氨基酚、4-氨基-3-硝基酚、4-羟基丙基胺-3-硝基酚、羟基蒽基氨基丙基甲基吗啉代硫酸二甲酯、4-硝基苯基氨基乙脲、6-硝基对甲苯胺、酸性蓝62、酸性蓝9、酸性红35、酸性红87(Eosin)、酸性紫43、酸性黄1、碱性蓝3、碱性蓝6、碱性蓝7、碱性蓝9、碱性蓝12、碱性蓝26、碱性蓝99、碱性棕16、碱性棕17、碱性红2、碱性红22、碱性红76、碱性紫14、碱性黄57、碱性黄9、分散蓝3、分散橙3、分散红17、分散紫1、分散紫4、分散黑9、坚牢绿FCF、HC蓝2、HC蓝7、HC蓝8、HC蓝12、HC橙1、HC橙2、HC红1、HC红10-11、HC红13、HC红16、HC红3、HC红RN、HC红7、HC紫1、HC紫2、HC黄2、HC黄5、HC黄5、HC黄6、HC黄7、HC黄9、HC黄12、HC红8、羟乙基-2-硝基对甲苯胺、N,N-二(2-羟乙基)-2-硝基对苯二胺、HC紫BS、苦氨酸、溶剂绿7。
本发明聚合物毛发染料不需要加入任何氧化剂以显示它们的染色效果。这一事实可以减少毛发损害。此外,通过使用本发明毛发染料可预防已察觉的或已记载的许多目前氧化性毛发染料的缺点,如它们的皮肤刺激性、皮肤敏感性及过敏性。再者,本发明的毛发染料比氧化性毛发染料更容易施用并更容易用于配制剂中,因为当施用于头上后不发生化学反应。特别有利的事实是其染色时间比使用氧化染料染色明显要更短(约5-10分钟)。
此外,式(1a)和(1b)染料可与至少一种阳离子偶氮染料组合,例如,与GB-A-2 319 776中所公开的化合物以及DE-A-299 12 327中所述的嗪染料及其与本文所述的其他直接染料的混合物组合。
式(1a)和(1b)染料也可与酸性染料组合,例如,根据国际命名(染料索引)或商品名称已知的染料。
式(1a)和(1b)染料也可与非荷电染料组合。
此外,式(1a)和(1b)染料也可与氧化染料体系组合使用。
在初始状态时不是染料而是染料前体的氧化染料根据其化学性质分为显色剂和成色剂化合物。
合适的氧化染料例如描述于以下文献中:
-DE 19 959 479,尤其是第2栏第6行至第3栏第11行;
-“Dermatology”,Ch.Culnan,H.Maibach编辑,Verlag Marcel DekkerInc.,New York,Basle,1986,第7卷,Ch.Zviak,The Science of Hair Care,第8章,第264-264页(氧化染料);
优选的显色剂化合物例如为在对位或邻位被取代或未取代的羟基-或氨基残基取代的芳族伯胺;或二氨基吡啶衍生物,杂环腙,4-氨基吡唑衍生物,2,4,5,6-四氨基嘧啶衍生物;或不饱和醛,如DE 19 717 224,尤其是第2页第50-66行和第3页第8-12行所述;或阳离子型显色剂化合物,如WO 00/43367,尤其是第2页第27行至第8页第24行,特别是第9页第22行至第11页第6行所述。
此外,可以以使用其生理相容的酸加成盐形式,如盐酸盐或硫酸盐使用显色剂化合物。具有芳族OH基团的显色剂化合物与碱一起呈其盐形成如碱金属酚盐也是合适的。
优选的显色剂化合物公开于DE 19959479,第2页第8-29行中。
更优选的显色剂化合物为对苯二胺、对甲苯二胺、对-、间-、邻氨基酚、N,N-二(2-羟乙基)对苯二胺硫酸盐、2-氨基-4-羟乙基氨基茴香醚硫酸盐、羟乙基-3,4-亚甲基二氧苯胺、1-(2′-羟乙基)-2,5-二氨基苯、2,6-二甲氧基-3,5-二氨基吡啶、羟基丙基-二(N-羟乙基-对苯二胺)盐酸盐、羟乙基对苯二胺硫酸盐、4-氨基-3-甲基酚、4-甲基氨基酚硫酸盐、2-氨基甲基-4-氨基酚、4,5-二氨基-1-(2-羟乙基)-1H-吡唑、4-氨基-间甲酚、6-氨基-间甲酚、5-氨基-6-氯甲酚、2,4,5,6-四氨基嘧啶、2-羟基-4,5,6-三氨基嘧啶或4-羟基-2,5,6-三氨基嘧啶硫酸盐。
优选的成色剂化合物为间苯二胺衍生物、萘酚、间苯二酚和间苯二酚衍生物、吡唑啉酮和间氨基酚衍生物,最优选的成色剂化合物公开于DE19959479,第1页第33行至第3页第11行。
此外,可自氧化的化合物也可与式(1a)和(1b)染料组合使用。
式(1a)和(1b)染料也可与天然存在的染料组合使用。
此外,式(1a)和(1b)染料也可与封闭的重氮化化合物组合使用。
合适的重氮化化合物例如为WO2004/019897中的式(1)-(4)化合物(连页1和2)及在相同文献中于第3-5页上所公开的相应水溶性偶合组分(I)-(IV)。
此外,本发明染料也可与描述于DE 10 2006 062 435 A1、WO00038638、DE 10241076及WO 05120445中通过反应性羰基化合物和CH-酸性化合物的反应而制备的染料组合使用,
-与描述于DE 10 2006 036898及DE 10 2005 055496的噻二唑染料组合使用,
-与描述于例如WO 07110532及WO 07110542的荧光茋硫染料组合使用,
-与描述于WO 07071684及WO 07071686的四氮杂五次甲基染料组合使用,
-与描述于FR 2879195、FR 2879127、FR 2879190、FR 2879196、FR2879197、FR 2879198、FR 2879199、FR 2879200、FR 2879928、FR2879929及WO 06063869的二聚阳离子染料组合使用,
-与描述于EP 0850636的偶氮和苯乙烯基染料组合使用,
-与描述于FR 2882929的聚合物阴离子染料组合使用,
-与描述于WO 0597051、EP 1647580、WO 06136617的二硫化物染料组合使用,
-与描述于WO 07025889、WO 07039527的硫醇染料组合使用,
-与描述于US 20050050650和US 7217295的导电聚合物组合使用。
本发明还涉及用于染色有机材料的配制剂,该有机材料优选为含角蛋白的纤维,最优选为人类毛发,该配制剂包含至少一种式(1a)和(1b)染料。
优选,将式(1a)和(1b)染料掺入用于处理有机材料的组合物中,优选以组合物总重量计为0.001-5重量%(以下仅以“%”表示),特别为0.005-4%,更特别为0.1-3%的染色量。
在10-200℃,优选18-80℃,最优选20-40℃的温度下将本发明染色组合物施涂在毛发上。
可将配制剂以不同的技术形式施用在含角蛋白的纤维上,优选人类毛发上。
配制剂的技术形式为例如溶液,尤其为增稠含水溶液或含水酒精溶液、乳膏、泡沫、洗发剂、粉末、凝胶或乳液。
染色组合物通常以50-100克的量施用于含角蛋白的纤维。
配制剂的优选形式为即用型组合物或多隔室染色装置或“套组”,或任何具有隔室的多隔室包装系统,例如US 6,190,421的第2栏第16-31行中所述。
即用型染色组合物的pH值通常为2-11,优选5-10。
适合的美容护发配制剂为毛发处理制剂,例如,洗发剂和调理剂形式的洗发制剂、护发制剂(例如,预处理制剂或留置型产品,如喷雾剂、乳膏、凝胶、洗剂、摩丝和油、毛发强壮剂、定型乳膏、定型凝胶、润发脂、护发素、处理包、护发精华素(intensive hair treatment)、毛发结构化制剂(例如,永久性烫发(热烫、温烫、冷烫)用的烫发制剂)、毛发拉直制剂、液体毛发定型剂、毛发用泡沫、毛发用喷雾剂、漂白制剂(例如,过氧化氢溶液)、净亮洗发剂、漂白乳膏、漂白粉、漂白糊或油、暂时性-、半持久性-或持久性毛发着色剂、含自氧化染料的制剂或天然毛发着色剂(如指甲花或春黄菊)。
对于用在人类毛发上,通常可将本发明染色组合物加入含水美容载体中。合适的含水美容载体包括例如W/O、O/W、O/W/O、W/O/W或PIT乳液及所有种类的微乳液、乳膏、喷雾剂、乳液、凝胶、粉末以及适合用于含角蛋白的纤维上的含表面活性剂的起泡溶液,例如,洗发剂或其他制剂。这些使用形式详细描述于Research Disclosure 42448(1999年8月)中。若必要时,也可以将染色组合物掺入无水载体中,例如US-3 369 970中所述,尤其第1栏第70行至第3栏第55行。本发明的染色组合物也非常适用于DE-A-3 829 870中所述的使用染色梳或染色刷的染色法。
含水载体的成分是以通常量存在于本发明的染色组合物中,例如乳化剂可基于染色组合物总重量以0.5-30重量%的浓度存在于染色组合物中,而增稠剂以0.1-25重量%的浓度存在。
用于染色组合物的其他载体例如描述于Ch.Culnan,H.Maibach所编辑的“Dermatology”,Verlag Marcel Dekker Inc.,New York,Basle,1986,第7卷,Ch.Zviak,The Science of Hair Care,第7章第248-250页中,尤其在第243页第1行至第244页第12行中。
如果式(1a)和(1b)染料与氧化染料和/或其与酸的加成盐一起使用,则它们可分开或一起储存。优选将对还原或碱不稳定的氧化染料和直接染料分开储存。
式(1a)和(1b)染料可在液体至糊状制剂(含水或不含水)中或以干粉末形式储存。
当染料分开储存时,将反应性组分在紧临使用前相互充分混合。在干储存的情况下,通常加入确定量的热水(50-80℃),并在使用之前制备均匀的混合物。
本发明染色组合物可包含已知用于这些制剂的任何活性成分、添加剂或辅助剂,如表面活性剂、溶剂、碱、酸、香料、聚合物辅助剂、增稠剂及光稳定剂。
优选将下列辅助剂用于本发明的毛发染色组合物中:非离子聚合物、阳离子聚合物、丙烯酰胺/二甲基二烯丙基氯化铵共聚物、硫酸二乙酯季铵化的甲基丙烯酸二甲基氨基乙酯/乙烯基吡咯烷酮共聚物、乙烯基吡咯烷酮/咪唑啉甲氯化物共聚物、季铵化聚乙烯醇、两性离子聚合物及两性聚合物、阴离子聚合物、增稠剂、结构剂、毛发调理化合物、蛋白水解产物、芳香油、异山梨醇二甲酯和环糊精、加溶剂、抗头皮屑活性成分、用于调节pH值的物质、泛醇、泛酸、尿囊素、吡咯烷酮羧酸及其盐、植物提取物和维生素、胆固醇、光稳定剂及UV吸收剂、稠度调节剂、脂肪和蜡、脂肪链烷醇酰胺、分子量为150-50000的聚乙二醇和聚丙二醇、配位剂、溶胀及渗透物质、遮光剂、珠光剂、推进剂、抗氧化剂、含糖聚合物、季铵盐及细菌抑制剂。
本发明染色组合物通常包含至少一种表面活性剂。合适的表面活性剂为两性离子表面活性剂或两性表面活性剂,或更优选阴离子表面活性剂、非离子表面活性剂和/或阳离子表面活性剂。
本发明另一实施方案涉及含角蛋白纤维的染色。
该方法包括:
(a)用至少一种式(1a)和(1b)染料处理含角蛋白的纤维,和
(b)使纤维静置和然后冲洗纤维。
式(1a)和(1b)染料适于毛发的遍及(all-over)染色(也就是说第一次染色毛发),也适于其后的再次染色,或几绺或部分毛发的染色。
将式(1a)和(1b)染料例如通过用手、梳子、刷子或与梳子或喷嘴组合使用的瓶子按摩而施于毛发上。
在本发明的染色方法中,染色是否在其他染料存在下进行要根据待获得的色调而定。
更优选的是将含角蛋白的纤维染色的方法,其包括用至少一种式(1a)和(1b)染料、碱和氧化剂处理处理含角蛋白的纤维。
用式(1a)和(1b)染料和氧化剂染色含角蛋白的纤维,特别是人类毛发的优选实施方案包括:
a1)用任选含至少一种式(1a)和(1b)染料的氧化剂处理含角蛋白的纤维,
b1)用任选含至少一种式(1a)和(1b)染料且不含氧化剂的组合物处理含角蛋白的纤维;或者
a2)用任选含至少一种式(1a)和(1b)染料且不含氧化剂的组合物处理含角蛋白的纤维;
b2)用任选含至少一种式(1a)和(1b)染料的氧化剂处理含角蛋白的纤维,条件是在至少一个工艺步骤a1)、a2)、b1)或b2)中,存在式(1a)和(1b)染料。
通常,使含氧化剂的组合物在15-45℃下留在纤维上0-45分钟,特别是15-30分钟。
不含氧化剂的组合物经常包含常规辅助剂及添加剂。优选为描述于德国专利申请第3栏第17行至第41行中的那些。
通常,使式(1a)和(1b)染料和不含氧化剂的组合物在15-50℃下留在纤维上5-45分钟,特别为10-25分钟。
该方法的一个优选实施方案是在染色之后用洗发剂和/或弱酸,如柠檬酸或酒石酸清洗毛发。
对还原稳定的式(1a)和(1b)染料可与不含氧化剂的组合物一起储存且可作为单组合物使用。
有利的是对还原不稳定且含式(1a)和(1b)染料的组合物恰在染色方法之前用不含氧化剂的组合物制备。
在另一实施方案中,式(1a)和(1b)染料和不含氧化剂的组合物可同时或依次施用。
含氧化剂的组合物通常以与毛发量相比为足够量而均匀施用,通常为30-200克。
氧化剂例如为过硫酸盐或稀过氧化氢溶液、过氧化氢乳液或过氧化氢凝胶、碱土金属过氧化物、有机过氧化物(如过氧化脲、过氧化三聚氰胺),或如果使用基于半持久性直接毛发染料的调色粉末,则也可使用碱金属溴酸盐固定剂。
其他优选的氧化剂为:
-实现提亮着色的氧化剂,如WO 97/20545所述,尤其为第9页第5-9行,
-呈烫发固定溶液形式的氧化剂,如DE-A-19 713 698(尤其是第4页第52行至第55行及第60行与第61行)或在EP-A-1062940(尤其是第6页第41-47行)(以及其同族专利WO 99/40895)所述。
最优选的氧化剂为过氧化氢,优选以相应组合物重量的约2-30%,更优选约3-20%,最优选6-12%的浓度使用。
氧化剂优选可以以染色组合物总量计为0.01-6%,尤其是0.01-3%的量存在于本发明染色组合物中。
通常,用氧化剂染色在碱存在下进行,例如氨、碱金属碳酸盐、土金属(钾或锂)碳酸盐、链烷醇胺(如单、二或三乙醇胺)、碱金属(钠)氢氧化物、土金属氢氧化物或下式化合物:
其中:
L为亚丙基残基,其可被OH或C1-C4烷基取代;且
R5、R6、R7和R8互相独立或非独立地为氢、C1-C4烷基或羟基-(C1-C4)烷基。
含氧化剂的组合物的pH值通常为约2-7,特别为约2-5。
将包含式(1a)和(1b)染料的配制剂施用至含角蛋白的纤维上(优选为毛发)的优选方法是使用多隔室染色装置或“套组”或任何其他的多隔室包装系统,例如如WO 97/20545的第4页第19-27行所述。
通常在用染色溶液和/或烫发溶液处理之后冲洗毛发。
本发明另一优选的实施方案涉及一种用氧化染料染色毛发的方法,其包括:
a.将至少一种式(1a)和(1b)染料和任选至少一种偶合剂化合物和至少一种显色剂化合物以及任选包含至少一种其他染料的氧化剂混合,和
b.使含角蛋白的纤维与步骤a.中所制备的混合物接触。
为了调节pH值,例如如DE 199 59 479的第3栏第46-53行所述的有机或无机酸是适合的。
此外,本发明涉及一种用式(1a)和(1b)染料和可自氧化的化合物和任选其他染料染色含角蛋白的纤维的方法。
该方法包括:
a.将至少一种可自氧化的化合物和至少一种显色剂化合物和至少一种式(1a)和(1b)染料和任选其他染料混合,和
b.用步骤a.中所制备的混合物处理含角蛋白的纤维。
此外,本发明涉及一种用式(1a)和(1b)染料和封闭的重氮化化合物染色含角蛋白的纤维的方法,其包括:
a.在碱性条件下用至少一种封闭的重氮化化合物和偶合剂化合物和任选的显色剂化合物以及任选的氧化剂,且任选在其他染料存在下及任选用至少一种式(1a)和(1b)染料处理含角蛋白的纤维,和
b.通过用酸,任选在其他染料存在下,以及任选至少一种式(1a)和(1b)染料处理而将pH值调节至6-2,
条件是至少一个步骤a.或b.中存在至少一种式(1a)和(1b)染料。
封闭的重氮化化合物和偶合剂化合物以及任选的氧化剂和显色剂化合物可以任何所需顺序依次或同时施用。
优选封闭的重氮化化合物和偶合剂化合物以单组合物同时施用。
“碱性条件”表示8-10,优选9-10,尤其为9.5-10的pH值,其通过加入碱例如碳酸钠、氨或氢氧化钠而实现。
可将碱加到毛发、加到染料前体、封闭的重氮化化合物和/或水溶性偶合组分,或加到含有染料前体的染色组合物中。
酸例如为酒石酸或柠檬酸、柠檬酸凝胶、具有任选的酸性染料的适当缓冲溶液。
在第一阶段施用的碱性染色组合物的量与在第二阶段施用的酸性染色组合物的量之比优选为1∶3-3∶1,尤其约1∶1。
步骤a.的碱性染色组合物及步骤b.的酸性染色组合物在15-45℃下留在纤维上5-60分钟,特别在20-30℃下留5-45分钟。
此外,本发明涉及一种用式(1a)和(1b)染料和至少一种酸性染料染色含角蛋白的纤维的方法。
下列的实施例用来说明染色方法,而非将所述方法限制于此。除非另有说明,份和百分比基于重量。所述染料量相对于待染色的材料。
制备实施例
实施例A1:
步骤1
制备方法:
将L-赖氨酸HCl盐(50g,274mmol)和KOH(15.36g,274mmol)的混合物引入装有机械搅拌器的3颈敞口圆底烧瓶中。加入5mL水并将该混合物搅拌直至具有浆状稠度,随后加热至150℃。当该混合物溶化时,加入Zr(OnBu)4(4mL,80wt%,3mol%相对于L-赖氨酸单体)作为催化剂并保持0.5小时。
然后将该混合物加热至180℃并保持3小时。
使在聚合过程中生成的水从敞口反应器中逸出。将所得棕色固体溶于水中。
将不溶性杂质通过过滤除去并将水溶液冻干从而以黄棕色固体得到聚合物(A1)。
Mw 2.68k;Mn 1.4k
1H NMR(MeOD-d6):δ[ppm]4.3(br,1H),4.0(br,2H),3.4-3(br,17H包括MeOD),2.8(m,9H),2-1.1(br,111H)
实施例A2:
中间体P1的合成描述于IP.com Journal(2004),4(9),31中。
使2.2g实施例A1中获得的聚赖氨酸·KCl与0.255g氟化物衍生物P1(1mmol)在5ml甲醇中在室温下反应2天。
反应后,过滤除去沉淀的盐并将甲醇溶液在真空(1毫巴)下蒸发以得到2.7g红色聚合物(A2)。
实施例A3:
使2.2g实施例A1中获得的聚赖氨酸·KCl与0.637g氟化物衍生物P1(2.5mmol)在5ml甲醇中在室温下反应7天。
反应后,过滤除去沉淀的盐并将甲醇溶液在真空(1毫巴)下蒸发以得到2.587g红色聚合物(A3)。
1H NMR(MeOD-d6):δ[ppm]8-7.8(br,1H),7.6-7.45(br,1H),6.95-6.75(br,1H),4.6-3.85(br,3.5H),3.7-2.75(br,17H包括溶剂),2.2-0.9(br,13H)
实施例A4:
中间体P2的合成描述于WO 2004/7083312中。
使1.1g实施例A1中获得的聚赖氨酸·KCl与0.133g甲氧基衍生物P2(0.5mmol)在5ml甲醇中在室温下反应2天。
反应后,过滤除去沉淀的盐并将甲醇溶液在真空(1毫巴)下蒸发以得到712mg红色聚合物(A4)。
实施例A5和A6:
实施例A5:
将1.27g如J.Med.Chem 1992,第35卷,第23期,4259-4263所述制备的1,4-二[(3-氯-2-羟丙基)氨基]-9,10-蒽二酮(30mmol)在12.7ml吡啶和12.7ml甲苯中的混合物在100℃下在氮气气氛下加热2天。冷却后,将反应混合物蒸发至干并用二烷和甲醇(1/1)的混合物再结晶。过滤固体并用二烷洗涤。干燥后,以72%收率得到1.08g深蓝色粉末(A5)。
MS(ES+):m/z 465。
1H NMR(dmso-d6):δ[ppm]10.95(s,1H),9.03(d,2H),8.60(t,1H),8.25(m,2H),8.20(t,2H),7.8(m,2H),7.6(dd,2H),6.05-5.75(br,2H),4.9(d,1H),4.5(m,1H),4.2(br,1H),3.9(br,1H),3.8-3.4(br,6H)
实施例A6:
将441mg聚赖氨酸·KCl A1(2meq NH2)和251mg(A5)(1mmol)在3mlDMSO中溶剂化。
将反应混合物在室温下搅拌16小时并在100℃下保持3天。冷却后,将反应混合物在40ml乙酸乙酯中沉淀。滤出固体并用乙酸乙酯洗涤两次。真空干燥后,得到615mg深蓝色粉末(A6)。
1H NMR(MeOD-d6):δ[ppm]9.05(br,2H),8.65(br,1H),8.32(br,1H),8.15(br,3H),7.8(br,2H),7.75-7.5(br,2),4.8-2.9(br,包括MeOD),2-1.3(br,17H)
实施例A7:
实施例A8
步骤1
2.37g 1-氨基-4-(3-二甲氨基丙基)氨基蒽醌(如DE 2927520所述制备)和7.5ml二溴丙烷在30ml氯仿中的溶液氯在60℃下搅拌16小时。在将反应混合物冷却至室温后,滤出产物并在真空,30℃下干燥得到3.25g蓝色粉末(A7)。
MS(ES+):m/z 444,446。
UV/VIS(甲醇):λmax 603nm。
1H NMR(dmso-d6):δ[ppm]10.84(t,H),8.45(br,2H),8.24(m,2H),7.82(m,2H),7.50(d,2H),7.37(d,2H),3.59(m,2H),3.52(m,2H),3.43(m,4H),3.10(s,6H),2.30(m,2H),2.10(m,2H)。
步骤2
在70℃下,将552mg聚赖氨酸·KCl A1(2.5meq NH2)和525mg步骤1中制备的化合物(A7)(1mmol)在2ml甲醇和3ml乙腈的混合物中溶剂化。将反应混合物在70℃下搅拌3天。冷却后,将反应混合物在30ml乙酸乙酯中沉淀。过滤固体并用乙酸乙酯洗涤两次。真空干燥后,得到306mg深蓝色粉末(A8)。
1H NMR(dmso-d6):δ[ppm]10.9(br,1H),8.5-7.8(br,4H),7.65(br,2H),7.35(br,1H),7.2(br,1H),3.8-2.7(br,43H),2.7-2.5(br,2H),2.1-1(br,20H)
实施例A9:
含氟嵌段(P3)的合成描述于专利WO2006136617中。
将552mg聚赖氨酸·KCl A1(2.5meq NH2)和521mg B(1mmol)在5ml甲醇中溶剂化并在室温下搅拌5天。将反应混合物在40ml乙酸乙酯中沉淀。过滤固体并用乙酸乙酯洗涤两次。真空干燥后,得到578mg深蓝色粉末(A9)。
1H NMR(MeOD-d6):δ[ppm]8.56.8br,4.4-3.5br;3.-0.9br
B.应用实施例
毛发样品
对于应用实施例,使用以下毛发类型:
-一束金色毛发(VIRGIN White Hair fro IMHAIR Ltd.,经由G.Verga 8,90134 Palermo(意大利)),
-一束中等金色(middle blonde)毛发(UNA-Europ.,天然毛发,中等金色,来自Fischbach & Miller,Postfach 1163,88461 Laupheim,德国),
-一束漂白的毛发(UNA-Europ.,天然毛发,白色漂白的金色,来自Fischbach & Miller,Postfach 1163,88461 Laupheim,德国)。
染色溶液
将0.2%w/w或1%w/w实施例A1-A5所述染料中的一种溶于Plantaren水溶液(10%w/w Plantacare 200UP(ID:185971.5);用50%柠檬酸溶液或单乙醇胺溶液将pH值调节至9.5)。
根据下列程序使发束染色:
将染色溶液直接施用于干燥毛发,在室温下保持20分钟,然后在自来水下清洗(水温:37℃+/-1℃;水流速:5-6l/分钟)。然后用纸巾压出水并在室温下在玻璃板上干燥过夜。
为了测定耐洗坚牢度,将两组发束在相同条件下染色。将一组染色的发束用市售洗发剂(商品名GOLDWEL,Color & Highlights,护色洗发剂)在自来水下(水温度:37℃+/-1℃;水流速:5-6l/分钟)清洗,每一发束使用约0.5克洗发剂。
最后将发束在自来水下冲洗,用纸巾压出水、梳理并用毛发干燥机或在室温下干燥。重复该步骤10次。
然后,使用根据Herbst & Hunger的“Industrial Organic Pigment”,第2版,第61页,Nr10:DIN 54 001-8-1982,“Herstellung und Bewertungdernderung der Farbe”,ISO 105-A02-1993的灰度色标(1-5,其中5为完全未发生变化)评估经清洗的发束组相对于未清洗的发束组的色彩损失。
表1:染色结果
聚合物染料混合物:
染料乳液,pH=10.5
成分 | w/w% |
如表2和3中所述的染料混合物 | x |
十六/十八醇 | 12.00 |
十六/十八醇聚氧乙烯(20)醚 | 4.50 |
失水山梨醇聚氧乙烯(20)醚硬脂酸酯 | 2.30 |
硬脂酸甘油酯SE | 2.00 |
失水山梨醇硬脂酸酯 | 0.75 |
油基聚氧乙烯(5)醚 | 1.25 |
辛酸/癸酸三甘油酯 | 0.50 |
EDTA二钠 | 0.05 |
单乙醇胺99% | 0.90 |
氢氧化铵29% | 6.60 |
二羟基丙基PEG-5亚油基氯化铵 | 0.50 |
水解大豆蛋白20% | 0.50 |
Fragrance Drom 847 735-Day at the Beach | 0.50 |
去离子水70℃ | 加至100.00 |
使所述染料乳液与1.5wt%的9%过氧化氢溶液混合并将混合物立即施用于棕色毛发。
30分钟后,将毛发清洗,用洗发水洗涤,清洗并干燥。
染色发束的颜色列在表2和3中。
表2:聚合物染料混合物
表3:聚合物染料和直接染料的混合物
Claims (16)
1.下式的聚合物染料:
和
其中:
A和B相互独立地为选自组氨酸、精氨酸、半胱氨酸、谷氨酰胺、谷氨酸、赖氨酸、天冬酰胺、丝氨酸、酪氨酸、苏氨酸、色氨酸和脯氨酸的聚合物骨架;
X1和X2相互独立地为选自如下的连接基团:-C1-C30亚烷基-和-C2-C12亚链烯基,其被一个或多于一个以下基团间隔和/或在一端或两端封端:-S-、-N-、-N=、-N(R5)-、-S(O)-、-SO2-、-(CH2CH2-O)1-5-、-(CH2CH2CH2-O)1-5-、-C(O)-、-C(O)O-、-OCO-、-CON(R1)-、-C(NR1R2)2-、-(R1)NC(O)-、-C(S)R1-;或任选包含至少一个杂原子且任选取代、饱和或不饱和、稠合或非稠合的芳族或非芳族二价基团;包含至少一个杂原子的饱和或不饱和、稠合或非稠合的芳族或非芳族二价基团,其任选被C1-C30烷基、C1-C30烷氧基、C2-C12链烯基、C5-C10芳基、C5-C10环烷基、C1-C10烷基(C5-C10亚芳基)、羟基或卤素取代;直接键;
R1、R2和R5相互独立地为氢;未取代或取代、直链或支化、单环或多环、间隔或未间隔的C1-C14烷基;C1-C14烷氧基;C2-C14链烯基;C1-C6烷基氨基;C6-C10芳基;C6-C10芳基-C1-C10烷基;C6-C10芳基-C1-C10烷氧基或C5-C10烷基(C5-C10芳基);
Y1和Y2相互独立地为选自偶氮、偶氮甲碱、联亚氨基次甲基、蒽醌、部花青、次甲基、嗪和苯乙烯基染料的有机染料的残基;或氢;其中Y1和Y2中至少一个为有机染料残基;
An1和An2相互独立地为选自氯离子和氟离子、硫酸根、硫酸氢根、磷酸根、四氟化硼离子、碳酸根、碳酸氢根、草酸根或C1-C8烷基硫酸根的阴离子;
a和b相互独立地为1-3的数;
m为0-5000的数;
n为0-5000的数;和
p为1-5000的数;
其中m+n+p之和≥3。
2.根据权利要求1的染料,其中:Y1和Y2具有相同含义。
3.根据权利要求1的染料,其中:所述聚合物骨架A和B和有机染料残基Y1和Y2均具有选自亲电子基团或亲核基团的官能团,所述亲电子基团选自卤化物、甲苯磺酰化物、甲磺酰化物、甲氧基、羧酸、羧酰氯、磺酰氯、环氧化物、酐的基团;所述亲核基团选自胺、胍、羟基和硫醇的基团。
4.根据权利要求2的染料,其中:所述聚合物骨架A和B和有机染料残基Y1和Y2均具有选自亲电子基团或亲核基团的官能团,所述亲电子基团选自卤化物、甲苯磺酰化物、甲磺酰化物、甲氧基、羧酸、羧酰氯、磺酰氯、环氧化物、酐的基团;所述亲核基团选自胺、胍、羟基和硫醇的基团。
5.根据权利要求1-4中任一项的染料,其中聚合物主链选自聚赖氨酸、聚谷氨酸和聚天冬酰胺。
6.根据权利要求1-4中任一项的染料,其中所述聚合物染料的分子量为400-50000。
7.根据权利要求1-4中任一项的染料,其对应于用X1-(Y1 a+)染料结构部分在α和/或ε位改性的下式聚赖氨酸:
其中:
X1、Y1、m、n和a如权利要求1所定义。
8.一种组合物,其包含至少一种如权利要求1所定义的式(1a)或(1b)染料。
9.根据权利要求8的组合物,其额外包含至少一种其他单直接染料和/或氧化剂。
10.根据权利要求8或9的组合物,其呈洗发剂、调理剂、凝胶或乳液形式。
11.一种染色有机材料的美容方法,其包括用至少一种根据权利要求1的式(1a)或(1b)染料处理所述有机材料。
12.根据权利要求11的美容方法,其包括用至少一种如权利要求1所定义的式(1a)或(1b)染料和氧化剂以及任选的其他直接染料处理所述有机材料。
13.根据权利要求11的美容方法,其包括用至少一种如权利要求1所定义的式(1a)或(1b)化合物和至少一种单氧化染料处理所述有机材料,或用如权利要求1所定义的式(1a)或(1b)染料和至少一种单氧化染料和氧化剂处理所述有机材料。
14.根据权利要求12的美容方法,其包括用至少一种如权利要求1所定义的式(1a)或(1b)化合物和至少一种单氧化染料处理所述有机材料,或用如权利要求1所定义的式(1a)或(1b)染料和至少一种单氧化染料和氧化剂处理所述有机材料。
15.根据权利要求11-14中任一项的美容方法,其中所述有机材料选自含角蛋白的纤维。
16.根据权利要求15的美容方法,其中所述含角蛋白的纤维为人类毛发。
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