CN107001523A - 乙烯‑(甲基)丙烯酸丙基庚基酯共聚物 - Google Patents
乙烯‑(甲基)丙烯酸丙基庚基酯共聚物 Download PDFInfo
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- CN107001523A CN107001523A CN201580060738.XA CN201580060738A CN107001523A CN 107001523 A CN107001523 A CN 107001523A CN 201580060738 A CN201580060738 A CN 201580060738A CN 107001523 A CN107001523 A CN 107001523A
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 70
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 90
- 239000000203 mixture Substances 0.000 claims abstract description 56
- CPFLCMDQFPWIDI-UHFFFAOYSA-N decan-4-yl 2-methylprop-2-enoate Chemical compound CCCCCCC(CCC)OC(=O)C(C)=C CPFLCMDQFPWIDI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- JLXBJSYBLWOYGV-UHFFFAOYSA-N decan-4-yl prop-2-enoate Chemical compound CCCCCCC(CCC)OC(=O)C=C JLXBJSYBLWOYGV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- RXBOCDZLKBPILN-UHFFFAOYSA-N 2-propylheptyl prop-2-enoate Chemical class CCCCCC(CCC)COC(=O)C=C RXBOCDZLKBPILN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 abstract description 18
- 239000003795 chemical substances by application Substances 0.000 abstract description 18
- 239000002537 cosmetic Substances 0.000 abstract description 18
- 230000000996 additive effect Effects 0.000 abstract description 14
- 238000009472 formulation Methods 0.000 abstract description 13
- 239000006185 dispersion Substances 0.000 abstract description 3
- 230000002708 enhancing effect Effects 0.000 abstract description 3
- -1 propylheptyl ester Chemical class 0.000 description 60
- 239000003921 oil Substances 0.000 description 41
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 35
- 239000000243 solution Substances 0.000 description 27
- 150000002148 esters Chemical class 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
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- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 238000000151 deposition Methods 0.000 description 10
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 238000005882 aldol condensation reaction Methods 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
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- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000007037 hydroformylation reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 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 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DCAYPVUWAIABOU-UHFFFAOYSA-N alpha-n-hexadecene Natural products CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 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 3
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 3
- 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 3
- 239000002245 particle Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 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 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N 2,2,4,6,6-pentamethylheptane Chemical compound CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- AOWJVNTZMBKLQO-UHFFFAOYSA-N 2-propan-2-ylheptan-1-ol Chemical class CCCCCC(CO)C(C)C AOWJVNTZMBKLQO-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005575 aldol reaction Methods 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 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
- 238000005516 engineering process Methods 0.000 description 2
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- 238000005227 gel permeation chromatography Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000002960 margaryl 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])[H] 0.000 description 2
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- 125000002958 pentadecyl 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])[H] 0.000 description 2
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- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8135—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers, e.g. vinyl esters (polyvinylacetate)
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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- A—HUMAN NECESSITIES
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- 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
- A61K2800/10—General cosmetic use
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
本发明涉及由特定量的(a)乙烯和(b)选自丙烯酸丙基庚基酯和甲基丙烯酸丙基庚基酯的单体以及任选地,至少一种其他单体形成的共聚物。所述共聚物可以用作化妆品配制剂的油溶性添加剂以及尤其是冲洗配制剂的油沉积增强剂。
Description
本发明涉及以共聚形式包含乙烯和至少一种丙烯酸或甲基丙烯酸的丙基庚基酯的共聚物。所述共聚物可以用作化妆品配制剂的油溶性添加剂以及尤其用作冲洗配制剂的油沉积增强剂。
化妆品配制剂中的油溶性添加剂与水溶性添加剂相比不太常见。
大多数非水溶性添加剂仅以分散形式存在。该类添加剂的实例包括经由水包油乳液(共)聚合得到的聚合物,如苯乙烯-丁二烯共聚物(例如参见US 4,009,139)、聚丙烯酸酯(例如参见US 6,132,705,US 2007/0218089)、丙烯酸酯-乙酸乙烯酯共聚物、丙烯酸酯-苯乙烯-丁二烯共聚物和乙酸乙烯酯-乙烯共聚物(例如参见US 4,126,144,EP 1634578)。这些种类的聚合物通常仅用于含水配制剂中且不会用于其中需要油和添加剂的纯溶液的情形,因为通过干燥方法制备油溶液的尝试昂贵且可能引起交联。
其他添加剂可以以纯净形式存在且可以直接用作含油化妆品配制剂的添加剂。该类添加剂的实例包括聚丙烯酸酯(例如参见US 6,664,356)和乙烯均聚物(例如参见US 2,628,187,US 3,215,599)。然而,该类添加剂在油中的液体溶液通常呈现不良稳定性。
因此,需要易溶于油中、形成对相分离和不匀性的形成稳定的均匀液体油溶液且可以用于含油液体化妆品配制剂中的添加剂。因此,本发明的目的是要提供该类添加剂。
惊人地发现该目的由具有下述性能的由包含乙烯和(甲基)丙烯酸支化烷基酯的单体形成的本发明共聚物实现。
包含衍生于乙烯和支化丙烯酸酯的单体单元的聚合物例如在US 8,338,344,WO2012/004240和WO 2007/135038中被描述为燃料和抗冲改性剂用冷流改进剂。
本发明提供了由如下单体形成的共聚物:
(a)乙烯,
(b)至少一种选自丙烯酸丙基庚基酯、甲基丙烯酸丙基庚基酯及其混合物的单体,以及
(c)任选地,至少一种不同于(a)和(b)的其他单体,
其中
(i)乙烯单体(a)的量相对于形成该共聚物的单体总重量为75-98重量%;
(ii)单体(a)加(b)的总量相对于形成该共聚物的单体总重量为至少90重量%;以及
(iii)单体(c)的按重量计的量若存在的话小于单体(b)的按重量计的量。
除非另有说明,在本发明上下文中适用下列通用定义:
C1-C3烷基为具有1-3个碳原子的直链或支化烷基。C1-C3烷基的实例为甲基、乙基、正丙基和异丙基。
C1-C4烷基为具有1-4个碳原子的直链或支化烷基。C1-C4烷基的实例为甲基、乙基、正丙基、异丙基、正丁基、2-丁基、异丁基和叔丁基。
C1-C9烷基为具有1-9个碳原子的直链或支化烷基。C1-C9烷基的实例包括甲基、乙基、正丙基、异丙基、正丁基、2-丁基、异丁基、叔丁基、戊基、新戊基、己基、庚基、辛基、2-乙基己基、壬基及其结构异构体。
C1-C20烷基为具有1-20个碳原子的直链或支化烷基。C1-C20烷基的实例包括甲基、乙基、正丙基、异丙基、正丁基、2-丁基、异丁基、叔丁基、戊基、新戊基、己基、庚基、辛基、2-乙基己基、壬基、癸基、2-丙基庚基,4-甲基-2-丙基己基、十一烷基、十二烷基(例如月桂基)、十三烷基、十四烷基(例如肉豆蔻基)、十五烷基、十六烷基、十七烷基、十八烷基(例如硬脂基)、十九烷基、二十烷基及其结构异构体。
C1-C20烷氧基为式-O-R的基团,其中R为本文所述的直链或支化C1-C20烷基。C1-C20烷氧基的实例包括甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、2-丁氧基、异丁氧基(2-甲基丙氧基)、叔丁氧基、戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、2,2-二甲基丙氧基、1-乙基丙氧基、己氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基、1-乙基-2-甲基丙氧基、庚氧基、辛氧基、2-乙基己氧基、壬氧基、癸氧基、2-丙基庚氧基、4-甲基-2-丙基己氧基、十一烷氧基、十二烷氧基、十三烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基、十八烷氧基、十九烷氧基、二十烷氧基及其符合式-O-R的结构异构体。
烷基和烷氧基可以未被取代或者被取代。取代烷基和烷氧基带有一个或不止一个选自包括但不限于羟基、C1-C4烷氧基、-NRaRb和羰基(-C(O)Ra)的组的取代基,其中Ra和Rb各自独立地为H或C1-C4烷基。在本发明上下文中,术语“烷基”优选涉及未被取代的烷基且术语“烷氧基”优选涉及未被取代的烷氧基。
用于生产本发明共聚物的甲基丙烯酸丙基庚基酯和丙烯酸丙基庚基酯单体通常通过用基本纯的2-丙基庚醇或通常通过2-丙基庚醇的工业生产得到且通常也称为“2-丙基庚醇”的丙基庚醇异构体的混合物酯化而制备。
纯2-丙基庚醇可以通过正戊醛的羟醛缩合和所得2-丙基庚烯醛的随后氢化制备,例如如US-A 2921089所述。除了主成分2-丙基庚醇外,市售2-丙基庚醇通常含有2-丙基庚醇的异构体作为副产物,如2-丙基-4-甲基己醇、2-丙基-5-甲基己醇、2-异丙基庚醇、2-异丙基-4-甲基己醇、2-异丙基-5-甲基己醇和/或2-丙基-4,4-二甲基戊醇。还可以存在2-丙基庚醇的其他异构体,如2-乙基-2,4-二甲基己醇、2-乙基-2-甲基-庚醇和/或2-乙基-2,5-二甲基己醇。
为了生产2-丙基庚醇,可以将不同的碳水化合物源用作原料,例如1-丁烯、2-丁烯、萃余液I(在分离丙二烯类、乙炔类和二烯之后由裂化器的C4馏分得到的链烷烃/链烯烃混合物,其除了1-和2-丁烯外仍含有显著量的异丁烯)或萃余液II(通过分离异丁烯由萃余液I得到,其除了1-和2-丁烯外仅含有少量残留异丁烯)。当然可以将萃余液I和萃余液II的混合物用作2-丙基庚醇的生产中的原料。这些烯烃和烯烃混合物可以使用钴或铑催化剂由本领域已知的方法加氢甲酰基化,从而使1-丁烯转化成正戊醛和异戊醛(2-甲基丁醛)的混合物,其中正/异比取决于催化剂和所应用的加氢甲酰基化条件在相对宽的范围内变化。例如,当使用三苯基膦改性的均相铑催化剂(Rh/TPP)时,所形成的正戊醛和异戊醛的正/异比通常为10:1-20:1,而当使用亚磷酸酯配体(例如如US 5,288,918或WO 2005/028407所述)或氨基亚磷酸酯配体(例如如WO 02/083695所述)改性的铑催化剂时几乎仅形成正戊醛。2-丁烯通过Rh/TPP催化剂体系的转化非常缓慢,使得可以从加氢甲酰基化混合物回收最大量的2-丁烯。相反,上述用亚磷酸酯配体或氨基亚磷酸酯配体改性的铑催化剂允许2-丁烯的有效加氢甲酰基化,其中大部分形成正戊醛。基本上所有催化剂体系导致烯属原料中所含异丁烯加氢甲酰基化成2-甲基丁醛以及取决于该催化剂还有少量新戊醛。
可以在羟醛缩合反应之前将C5-加氢甲酰基化产物,即正戊醛或其与异戊醛、2-甲基丁醛和/或新戊醛的混合物(取决于所用原料和催化剂)完全或部分分离成其单一组分。这允许控制本发明共聚物中所用酯单体组合物的C10醇组分的异构体组成。或者,C5-加氢甲酰基化产物可以不预先分离单个异构体而用于羟醛缩合反应中。羟醛缩合可以在碱性催化剂如氢氧化钠或氢氧化钾水溶液存在下进行,例如如EP 0366089、US 4,426,524或US 5,434,313所述。若使用正戊醛,则羟醛缩合得到2-丙基庚醛作为基本唯一缩合产物。若使用C5醛异构体的混合物,则羟醛缩合得到相同醛分子的同缩合产物和不同C5醛异构体的交叉缩合产物的异构体混合物。当然,羟醛缩合可以由单个异构体的定向转化控制,以形成单一羟醛缩合异构体作为主要或基本唯一产物。可以使用本领域已知的氢化催化剂(例如上面作为可以用于醛氢化提到的那些)氢化羟醛缩合的产物以形成相应醇或醇混合物。所述氢化通常在将羟醛缩合产物从反应混合物中分离(优选通过蒸馏)以及需要的话,通过蒸馏提纯之后进行。
当形成本发明共聚物的丙烯酸丙基庚基酯和甲基丙烯酸丙基庚基酯单体由2-丙基庚醇及其异构体的混合物(如上所述)制备时,2-丙基庚醇在所述混合物中的含量相对于该异构体混合物的总重量通常为至少50重量%,尤其是60-98重量%,优选80-95重量%,特别优选85-95重量%。
2-丙基庚醇及其异构体的合适混合物例如包括包含60-98重量%2-丙基庚醇,1-15重量%2-丙基-2-甲基己醇,0.01-20.00重量%2-丙基-5-甲基己醇和0.01-24.00重量%2-异丙基庚醇的混合物,其中所述组分的总和相对于该异构体混合物的总重量优选为100重量%。
2-丙基庚醇及其异构体的优选混合物为包含85-95重量%2-丙基庚醇,5-12重量%2-丙基-4-甲基己醇,0.1-2.0重量%2-丙基-5-甲基己醇和0.01-1.00重量%2-异丙基庚醇的混合物,其中所述组分的总和相对于该异构体混合物的总重量优选为100重量%。
若使用所述异构体丙基庚醇-异构体混合物代替纯2-丙基庚醇来生产用于本发明共聚物的(甲基)丙烯酸丙基庚基酯单体,则用甲基丙烯酸或丙烯酸酯化的丙基庚基的异构体组成基本与用于酯化反应的丙基庚醇-异构体混合物的异构体组成相同。
因此,本文所用术语“丙基庚醇”包括2-丙基庚醇以及如上所述的其结构异构体。同样,本文所用术语“丙烯酸丙基庚基酯”包括2-丙基庚醇的丙烯酸酯以及如上所述的2-丙基庚醇的结构异构体的丙烯酸酯。类似地,本文所用术语“甲基丙烯酸丙基庚基酯”包括2-丙基庚醇的甲基丙烯酸酯以及如上所述的2-丙基庚醇的结构异构体的甲基丙烯酸酯。
根据特殊实施方案,形成本发明共聚物的单体(b)为丙烯酸和/或甲基丙烯酸的2-丙基庚醇酯。
根据其他特殊实施方案,形成本发明共聚物的单体(b)为丙烯酸丙基庚基酯,优选丙烯酸2-丙基庚基酯。
本发明共聚物由如下单体形成:
(a)乙烯单体;
(b)至少一种选自丙烯酸丙基庚基酯、甲基丙烯酸丙基庚基酯以及丙烯酸丙基庚基酯和甲基丙烯酸丙基庚基酯的混合物的单体;
以及任选地,(c)至少一种不同于(a)和(b)的其他单体。
单体(a),即乙烯单体,相对于形成本发明共聚物的单体总重量占75-98重量%(即重量百分数)。优选单体(a)的量相对于形成本发明共聚物的单体总重量为78-97重量%,更优选79.0-96.5重量%,最优选约80-96重量%。
单体(a),即乙烯单体,以及单体(b),即选自丙烯酸丙基庚基酯、甲基丙烯酸丙基庚基酯及其混合物的单体,相对于形成本发明共聚物的单体总重量占至少90重量%。优选单体(a)和(b)的总量相对于形成本发明共聚物的单体总重量为至少91重量%,更优选至少95重量%,至少97重量%或至少98重量%,特别是至少99重量%。
基本由单体(a)和(b)形成的本发明共聚物为本发明的特殊组实施方案。术语“基本”就此而言是指共聚物包含不超过5重量%,优选不超过3重量%,更优选不超过2重量%,尤其不超过1重量%的单体(a)和(b)以外的组分。例如,作为制备的结果可能存在小比例的用作调节剂(链转移剂)的化合物。
当形成本发明共聚物的单体包含单体(a)和(b)以外的单体时,所述单体(本文称为单体(c))按重量计的量小于单体(b)按重量计的量。
合适的单体(c)包括但不限于:
-式M1的单体:
其中
R1、R2和R3各自独立地为H或C1-C4烷基,优选H或甲基,更优选R1、R2和R3中的两个各自为H且另一个为H或甲基,尤其是R1、R2和R3各自为H;以及
R4为C1-C20烷基,优选C1-C9烷基,更优选C1-C3烷基,具体为乙基或甲基,尤其是甲基;
-丙烯酸丙基庚基酯和甲基丙烯酸丙基庚基酯以外的式M2的单体:
其中
R5、R6和R7各自独立地为H或C1-C4烷基,优选H或甲基,更优选R5、R6和R7中的两个各自为H且另一个为H或甲基,尤其是R5、R6和R7各自为H;以及
R8为C1-C20烷基或选自具有4-20个,6-20个,8-20个,尤其是9-20个碳原子的直链和支化烷基,其中优选支化烷基;
-式M3的单体:
其中
R9独立地为H或C1-C4烷基,优选H或甲基,尤其是H;
R10和R11中的一个为-C(O)R13且另一个为H或C1-C4烷基;以及
R12和R13各自独立地为-OH或C1-C20烷氧基;或者
R12和R13一起形成-O-基团;
以及该类单体中两种或更多种的混合物。
单体M1的实例包括但不限于脂族C2-C20羧酸如乙酸,丙酸,丁酸,戊酸,异戊酸,新戊酸,新戊酸,己酸,庚酸,辛酸,壬酸,2-乙基己酸,VersaticTM酸,尤其是新壬酸和新癸酸(例如VeoVaTM=支链烷烃羧酸的乙烯基酯),癸酸,新十一烷酸,月桂酸,十三烷酸,肉豆蔻酸,十五烷酸,棕榈酸,十七烷酸,硬脂酸,十九烷酸和花生酸的乙烯基或丙烯基酯。优选所述羧酸的乙烯基酯,特别优选乙酸乙烯酯。
根据本发明的特殊实施方案,该共聚物由单体(a)、(b)和M1形成,其中单体M1优选为乙酸乙烯酯。根据本发明的更具体实施方案,该共聚物由乙烯单体、丙基庚基单体和乙酸乙烯酯单体形成。
单体M2优选为选自丙烯酸(R5、R6和R7=H)、甲基丙烯酸(R5、R6=H;R7=甲基)、巴豆酸(R6、R7=H;R5=甲基)和异巴豆酸(R5、R7=H;R6=甲基),更优选丙烯酸和甲基丙烯酸,尤其是丙烯酸的α,β-不饱和羧酸的酯。单体M2的实例包括但不限于丙烯酸正丁酯、丙烯酸2-丁基酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正戊酯、丙烯酸新戊酯、丙烯酸异戊酯、丙烯酸己酯、丙烯酸庚酯、丙烯酸辛酯、丙烯酸2-乙基己-1-基酯、丙烯酸壬酯、丙烯酸癸酯、丙烯酸2-丙基庚-1-基酯、丙烯酸4-甲基-2-丙基己-1-基酯、丙烯酸十一烷基酯、丙烯酸月桂酯、丙烯酸十三烷基酯、丙烯酸肉豆蔻基酯、丙烯酸棕榈基酯、丙烯酸硬脂基酯、丙烯酸十九烷基酯和丙烯酸二十烷基酯;以及还有甲基丙烯酸、巴豆酸和异巴豆酸的相应酯,优选丙烯酸酯(丙烯酸的酯)。
单体M3为烯属不饱和脂族1,2-二羧酸的酸酐(R12和R13一起形成-O-基团),烯属不饱和脂族1,2-二羧酸(R12和R13=-OH),C1-C20醇的烯属不饱和脂族1,2-二羧酸单酯(R12和R13中的一个=-OH且另一个为C1-C20烷氧基),或者C1-C20醇的烯属不饱和脂族1,2-二羧酸二酯(R12和R13=C1-C20烷氧基)。优选R9和R10为H,或者R9和R11为H。因此,单体M3优选选自马来酸酐、马来酸、富马酸、C1-C20醇的马来酸单-和二酯以及C1-C20醇的富马酸单-和二酯。单体M3的实例包括但不限于富马酸和马来酸的单甲基、单乙基、单丙基、单异丙基、单正丁基、单仲丁基、单异丁基、单叔丁基、单戊基、单己基、单庚基、单辛基、单-2-乙基己基、单壬基、单癸基、单-2-丙基庚基、单-4-甲基-2-丙基己基、单十一烷基、单十二烷基、单十三烷基、单十四烷基、单十五烷基、单十六烷基、单十七烷基、单十八烷基、单十九烷基、单二十烷基酯,以及相应醇的对称以及混合富马酸和马来酸二酯。
本发明共聚物不是接枝共聚物且没有交联。它们可以是直链或支化的,其中优选由高压聚合得到的具有典型支化结构的共聚物(包括由于CH2基团到绕共聚单体单元的CH2回咬的短链支化)。
本发明共聚物优选具有约1,000-4,800g/mol,更优选1,500-4,500g/mol,最优选2,000-4,000g/mol的数均分子量Mn。
本发明共聚物优选具有1.5-5.0,优选1.8-4.0,尤其是1.9-3.5的Mw/Mn比(=PDI)。
在本发明上下文中所给重均分子量(Mw)、数均分子量(Mn)及其商PDI(=Mw/Mn)的细节优选基于已经借助凝胶渗透色谱法(聚苯乙烯标样)测定的值。
本发明共聚物的粘度(根据Ubbelohde DIN 51562测定)通常为约100-3,000mm2/s,特别是约250-2,750mm2/s,尤其是约500-2,500mm2/s,在每种情况下在120℃的温度下。
共聚物的制备
本发明聚合物或按照本发明使用的聚合物通过本身已知的方法制备,优选由现有技术已知用于不饱和化合物的直接自由基高压共聚的方法(例如参见Ullmann'sEncyclopedia of Industrial Chemistry,第5版:Waxes,第A 28卷,第146页及随后各页,VCH Weinheim,Basle,Cambridge,New York,Tokyo,1996;以及还有EP-A-157106,EP-A-244855,EP-A-0007590,US 6,300,430,US 3,627,838,DE-A-2515805,DE-A-3141507)制备。
聚合物优选在搅拌高压釜中或者更优选在高压管式反应器或这二者的组合中制备。在高压釜中,长度/直径比主要在2:1-30:1,优选5:1-20:1范围内变化。管式反应器主要具有>1,000,优选5,000-30,000的长度/直径比。
高压聚合通常在1,000-3,000巴,优选1,500-2,000巴的压力下进行。反应温度通常为120-320℃,优选140-280℃,更优选140-250℃。
用于调节共聚物分子量的调节剂例如选自通式(I)的脂族醛和脂族酮及其混合物:
其中Ra和Rb相同或不同且选自:
-氢;
-C1-C6烷基,如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、仲戊基、新戊基、1,2-二甲基丙基、异戊基、正己基、异己基、仲己基;更优选C1-C4烷基,如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基;以及
-C3-C12环烷基,如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十一烷基和环十二烷基;优选环戊基、环己基和环庚基;
或者其中Ra和Rb共价相互连接以形成4-13员环。例如,Ra和Rb一起为选自-(CH2)4-、-(CH2)5-、-(CH2)6-、-(CH2)7-、-CH(CH3)-CH2-CH2-CH(CH3)-和-CH(CH3)-CH2-CH2-CH2-CH(CH3)-的亚烷基。
非常特别优选将丙醛或乙基甲基酮用作调节剂。
其他非常合适的调节剂是未支化脂族烃,例如丙烷,或者具有叔氢原子的支化脂族烃,例如异丁烷、异戊烷、异辛烷或异十二烷(2,2,4,6,6-五甲基庚烷)。额外地,可以使用其他调节剂如烯烃(例如丙烯、丁烷、己烯)。
还优选上述调节剂与氢气的混合物或单独的氢气。
调节剂的用量对应于高压聚合方法的常规量。
用于自由基聚合的起始剂可以使常规自由基引发剂,例如有机过氧化物、氧或偶氮化合物。多种自由基引发剂的混合物也是合适的。所用自由基引发剂例如可以是一种或多种选自下列市售物质的过氧化物:
-过氧化二癸酰、2,5-二甲基-2,5-二(2-乙基己酰基过氧)己烷、过氧-2-乙基己酸叔戊酯、过氧化二苯甲酰、过氧-2-乙基己酸叔丁酯、过氧二乙基乙酸叔丁酯、过氧二乙基异丁酸叔丁酯、作为异构体混合物的1,4-二(叔丁基过氧羰基)环己烷、过异壬酸叔丁酯、1,1-二(叔丁基过氧)-3,3,5-三甲基环己烷、1,1-二(叔丁基过氧)环己烷、甲基异丁基酮过氧化物、过氧异丙基碳酸叔丁酯、2,2-二(叔丁基过氧)丁烷、过氧乙酸叔丁酯、过氧新戊酸叔丁酯或过氧新戊酸叔戊酯;
-过氧苯甲酸叔丁酯、过氧化二叔戊基、过氧化二枯基、异构的二(叔丁基过氧异丙基)苯、2,5-二甲基-2,5-二叔丁基过氧己烷、过氧化叔丁级枯基、2,5-二甲基-2,5-二(叔丁基过氧)己-3-炔、过氧化二叔丁基、1,3-二异丙基单氢过氧化物、枯烯氢过氧化物或叔丁基氢过氧化物;
-例如如EP 0813550所述的二聚或三聚酮过氧化物。
特别合适的过氧化物是过氧化二叔丁基、过氧新戊酸叔丁酯、过氧异壬酸叔丁酯或过氧-2-乙基己酸叔丁酯或其混合物。偶氮化合物的实例是偶氮二异丁腈“AIBN”。自由基引发剂以常用于聚合的量计量加入。
根据优选方法,本发明共聚物通过使单体(a)和(b)以及需要的话单体(c)(例如单体M1、M2和M3中的一种或不止一种)单独或者以混合物在调节剂存在下优选连续通过保持在约1,500-2,000巴的压力下(例如在约1,700巴下)和在约120-160℃的温度下(例如在约140℃下)的管式反应器而制备。作为通常溶于合适溶剂,例如异十二烷中的引发剂连续加料的结果,反应混合物的温度升高。控制工艺条件(尤其是引发剂加料速率)以将反应器中的温度保持在所需反应温度,例如200-250℃的温度。存在于流出物中的聚合物可以以常规方式分离或与未转化反应物一起再循环到反应器中。
对该方法的改性当然是可能的且可以没有不可接受的效果地由本领域熟练技术人员进行。仅列举几种示例性改性,例如,单体和调节剂可以分开计量加入反应混合物中和/或反应温度可以在该方法过程中改变。
本发明共聚物通常以基本无规分布包含衍生于单体(a)、单体(b)以及若存在的话,单体(c)的单体单元。然而,由于在给定聚合条件下的不同聚合速率,根据各单体的选择可以形成梯度聚合物。例如,在上述反应条件下丙烯酸酯通常比乙酸乙烯酯更快速聚合,从而例如得到其中丙烯酸酯浓度沿着聚合物主链降低,而乙酸乙烯酯和乙烯基本均匀分布于该链上的共聚物。
高压聚合使得将大量极性单体引入聚乙烯的骨架中。或者可以将中压技术(通常70-300巴)用于聚合,条件是在聚合工艺过程中将溶剂加入反应混合物中。该溶剂例如可以是化妆油。优选高压聚合,因为不要求将溶剂加入单体溶液中(反应混合物中的过量超临界乙烯可以用作溶剂)。
共聚物的油溶液
本发明共聚物在油中可溶且优选用作油的添加剂。
有利的是,本发明共聚物是化妆品可接受的且因此可以用作(尤其液体)化妆品配制剂的添加剂。“化妆品可接受的”是指相应化合物在用于化妆品配制剂中时不引起不希望的反应,如皮肤刺激。
优选将该共聚物用作化妆品配制剂中所用天然油如植物油,即通常呈甘油三酯形式的自然存在于植物中中(通常存在于其含油果实中)的脂肪酸酯的添加剂。基本上所有植物油适合化妆品应用,最常使用大豆油、菜籽油和棕榈油。常用于化妆品中的其他植物油包括摩洛哥坚果油、鳄梨油、玫瑰油、葵花油、橄榄油和椰子油。
本发明共聚物的该类油溶液在室温(或更高温度)下稳定至少1小时并且可以在室温下稳定超过24小时。稳定的共聚物/油溶液在规定的时间期间内(例如在室温下超过1小时或者甚至超过24小时)保持均匀和透明而没有任何相分离、颗粒形成或可见浊度。
天然油通常含有烷基链和极性基团。不希望受理论束缚,假定大部分由乙烯衍生的单体单元构成的共聚物中(甲基)丙烯酸酯衍生的单体单元的存在降低了共聚物的结晶度,并且(甲基)丙烯酸丙基庚基酯衍生的单体单元的支化侧链的存在提高了共聚物在该油中的溶解度并导致分子相互作用强到足以允许本发明共聚物在油中的溶液在室温(或更高温度)下稳定至少1小时。
共聚物在化妆品配制剂中的用途
本文所述共聚物/油溶液可以用于化妆品配制剂中。它们尤其可以用作液体化妆品配制剂的添加剂以及优选用于冲洗化妆品配制剂,例如沐浴、洗发剂和调理剂配制剂。在这些应用中,本发明共聚物用于提高冲洗后留在皮肤或头发上的油量。换言之,本发明共聚物可以用作油沉积增强剂。
本文所述具有油溶液的液体化妆品配制剂,如沐浴和洗发剂配制剂,可以通过将预混的共聚物/油溶液加入液体基础配制剂(如沐浴或洗发剂配制剂)中而制备,例如以约10重量份共聚物/油溶液对约90重量份基础配制剂的比例。
通常而言,含有本发明共聚物(作为与油的预混物加入)的补油液体化妆品配制剂(如沐浴或洗发剂配制剂)在10-50℃下稳定至少1个月,至少3个月,或者甚至6个月和更长。
本发明共聚物可以单独使用或者可以与也具有油沉积提高性能的常规添加剂组合使用。
本发明共聚物有利地基于油溶液的总量以定量比例使用,该定量比例在最终配制剂中呈现基本足够的油沉积提高效果。例如,共聚物以基于该配制剂的总重量为0.01-10.00重量%,优选0.05-6.00重量%,更优选0.1-3.0重量%,具体为0.5-1.5重量%的量使用。
实施例
1)聚合物的制备
总共19种不同聚合物通过相应单体在210-240℃的反应温度和1,600-1,800巴的压力的高压聚合制备。单体及其在所得聚合物的总重量中的量示于表1中。
测定所述聚合物的粘度、数均分子量和PDI(=Mw/Mn)(参见表1)。数均分子量(Mn)和重均分子量(Mw)借助高温凝胶渗透色谱法使用ISO 16014-1:2003(E)和ISO 16014-4:2003(E)中所述方法测定:溶剂1,2,4-三氯苯(TCB),设备和溶液温度135℃以及作为浓度检测器的PolymerChar IR-4红外检测器(适合与TCB使用)。580g/mol至11,600,000g/mol的单分散聚苯乙烯(PS)标样以及十六烷用于分子量校准。所得校准曲线借助根据ISO 16014-2:2003(E)的通用校准方法适用于聚乙烯(PE)。粘度根据Ubbelohde DIN 51562在120℃下测定。
额外地,所得聚合物的单体含量通过使用Bruker AV 501装置(四氯乙烷,373K)的1H-NMR光谱法测定(数据未示出)。单体含量在每种情况下低于1,000ppm。
表1
单体缩写:
E=乙烯 EHA=丙烯酸乙基己基酯
PHA=丙烯酸2-丙基庚基酯 SA=丙烯酸硬脂基酯
PHMA=甲基丙烯酸2-丙基庚基酯 VAC=乙酸乙烯酯
2)油溶液
制备10重量%聚合物在大豆油中的混合物并在搅动下将其缓慢加热。对于每一实施例,确定其中形成均匀且透明溶液而没有任何相分离、颗粒形成或可见浊度的最小温度(参见表2中的“在SBO中的最小溶液温度”)。
此外,监测所述10重量%聚合物/油溶液在室温下的稳定性(参见表2中“SBO溶液的稳定性”)。只要溶液保持均匀而没有任何相分离可见就认为它们是稳定的。
3)化妆品配制剂
将实施例2的预混油(在高于相应最小溶液温度的温度下预热)以10份油溶液对90份基础配制剂的重量比连续分别加入液体沐浴基础配制剂(组成见表2)或液体洗发剂基础配制剂(组成见表3)(各自预热至80℃)中。
表2
沐浴 基础配制剂 | 量[g] |
蒸馏水 | 68.81 |
十三烷基醚硫酸钠 | 14.26 |
椰油酰胺基丙基甜菜碱B | 9.23 |
TDA 3-乙氧基化十三烷醇 | 1.48 |
氯化钠 | 4.75 |
瓜耳胶羟丙基三甲基氯化铵 | 0.48 |
黄原胶 | 0.22 |
丙烯酸酯/丙烯酸C10-30烷基酯交联聚合物 | 0.03 |
Polyox WSR-301 | 0.10 |
无水柠檬酸 | 0.12 |
防腐剂 | 0.52 |
总计 | 100.00 |
表3
将所述补油液体配制剂在25℃下储存并监测其稳定性(参见表4中的“沐浴露的稳定性”和“洗发剂的稳定性”)。只要配制剂保持均匀而没有任何相分离或更大颗粒形成可见就认为它们是稳定的。
此外,使用上述沐浴配制剂评价油沉积效果。测试者将限定量的沐浴配制剂应用于其手上,用水冲洗该配制剂并随后通过感觉评价给予油沉积等级,其中“x”是指在被处理手上基本缺乏可觉察的油沉积,“xx”是指可觉察的油沉积直到中等程度,以及“xxx”是指强烈可觉察的油沉积(参见表4中的“油沉积”)。
表4
当与大豆油混合时,本发明的示例性共聚物1-11呈现相对低得最小溶液温度且形成具有高稳定性的油溶液(>24小时)。额外地,实施例1-11的所述共聚物在用于冲洗沐浴配制剂中时具有显著以及强烈—只有一个例外—的油沉积效果。参考实施例A、B和H的油沉积效果也呈显著到强烈。然而,相应油溶液和化妆品配制剂明显不太稳定且在大豆油中的最小溶液温度比实施例1-11的情形显著要高。其他参考实施例没有显示出任何显著的油沉积效果,并且在大多数情况下也呈现出相应油溶液和化妆品配制剂的不良稳定性。
Claims (9)
1.一种由如下单体形成的共聚物:
(a)乙烯,
(b)至少一种选自丙烯酸丙基庚基酯、甲基丙烯酸丙基庚基酯及其混合物的单体,以及
(c)任选地,至少一种不同于(a)和(b)的其他单体,
其中
(i)乙烯单体(a)的量相对于形成所述共聚物的单体总重量为75-98重量%;
(ii)单体(a)加(b)的总量相对于形成所述共聚物的单体总重量为至少90重量%;以及
(iii)单体(c)的按重量计的量若存在的话小于单体(b)的按重量计的量。
2.权利要求1的共聚物,其中单体(a)加(b)的总量相对于形成所述共聚物的单体总重量为至少95重量%。
3.权利要求1的共聚物,仅由单体(a)和(b)形成。
4.权利要求1-3中任一项的共聚物,其中乙烯单体(a)的量相对于形成所述共聚物的单体总重量为78-97重量%。
5.权利要求1-4中任一项的共聚物,其中单体(b)为丙烯酸丙基庚基酯。
6.权利要求5的共聚物,其中单体(b)为丙烯酸2-丙基庚基酯。
7.权利要求1、2和4-6中任一项的共聚物,其中单体(c)选自式M1的单体:
其中
R1、R2和R3各自独立地为H或C1-C4烷基;以及
R4为C1-C20烷基。
8.权利要求7的共聚物,其中单体(c)为乙酸乙烯酯。
9.权利要求1-8中任一项的共聚物,具有的数均分子量Mn为1,000-4,800g/mol。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14192468 | 2014-11-10 | ||
EP14192468.8 | 2014-11-10 | ||
PCT/EP2015/076039 WO2016075070A1 (en) | 2014-11-10 | 2015-11-09 | Ethylene-propylheptyl(meth-)acrylate copolymers |
Publications (1)
Publication Number | Publication Date |
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CN107001523A true CN107001523A (zh) | 2017-08-01 |
Family
ID=51866088
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN201580060738.XA Withdrawn CN107001523A (zh) | 2014-11-10 | 2015-11-09 | 乙烯‑(甲基)丙烯酸丙基庚基酯共聚物 |
Country Status (8)
Country | Link |
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US (1) | US9914792B2 (zh) |
EP (1) | EP3218419A1 (zh) |
JP (1) | JP2017533331A (zh) |
KR (1) | KR20170084129A (zh) |
CN (1) | CN107001523A (zh) |
BR (1) | BR112017009609A2 (zh) |
CA (1) | CA2965228A1 (zh) |
WO (1) | WO2016075070A1 (zh) |
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US10851323B2 (en) | 2016-03-10 | 2020-12-01 | Basf Se | Aqueous polymer dispersions, a method for their preparation and the use thereof as pour-point depressants for crude oil, petroleum, and petroleum products |
PT3481920T (pt) | 2016-07-05 | 2021-11-10 | Basf Se | Utilização de inibidores de corrosão para combustíveis e lubrificantes |
EP3765529A1 (en) * | 2018-03-16 | 2021-01-20 | Basf Se | A high-pressure polymerization process for liquid ethylene copolymers |
WO2019175300A1 (en) | 2018-03-16 | 2019-09-19 | Basf Se | A lubricant comprising a liquid ethylene copolymer |
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US2628187A (en) | 1950-05-06 | 1953-02-10 | Res Prod Corp | Medicinal mineral oil vehicle thickened with polyethylene |
US2921089A (en) | 1957-11-27 | 1960-01-12 | Eastman Kodak Co | 2-propylheptanol and its esters |
US3215599A (en) | 1963-07-02 | 1965-11-02 | Warner Lambert Pharmaceutical | Process for preparing polymer waxmodified petroleum oil unctuous base |
US3627838A (en) | 1964-12-11 | 1971-12-14 | Exxon Research Engineering Co | Process for manufacturing potent pour depressants |
CA1043048A (en) | 1974-04-17 | 1978-11-21 | Exxon Research And Engineering Company | Copolymers of ethylene and ethylenically unsaturated monomers, process for their preparation and distillate oil containing said copolymers |
DE2430301C3 (de) | 1974-06-24 | 1978-09-07 | Basf Ag, 6700 Ludwigshafen | Trübungsmittel |
US4126144A (en) | 1976-12-30 | 1978-11-21 | Duarte Patricia A | Peelable human nail coatings |
EP0007590B1 (de) | 1978-07-26 | 1981-02-18 | BASF Aktiengesellschaft | Mitteldestillate des Erdöls, die als Dieseltreibstoffe oder leichtes Heizöl geeignet sind, mit verbesserter Filtrierbarkeit |
US4426524A (en) | 1980-09-02 | 1984-01-17 | Fmc Corporation | Heterocyclic substituted benzyl alcohol, insecticidal ester derivatives, and intermediates |
DE3141507A1 (de) | 1981-10-20 | 1983-04-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ethylenpolymerisaten in einem zweizonen-rohrreaktor bei druecken oberhalb 500 bar |
DE3404744A1 (de) | 1984-02-10 | 1985-08-14 | Basf Ag, 6700 Ludwigshafen | Copolymerisate des ethylens mit carboxylgruppenhaltigen comonomeren |
DE3615563A1 (de) | 1986-05-09 | 1987-11-12 | Basf Ag | Verfahren zur herstellung von copolymerisaten des ethylens mit vinylestern in einem roehrenreaktor bei druecken oberhalb 500 bar |
US4969953A (en) | 1988-10-25 | 1990-11-13 | Mitsubishi Kasei Corporation | Alcohol mixture for plasticizer and method for producing the same |
GB9207756D0 (en) | 1992-04-07 | 1992-05-27 | Davy Mckee London | Process |
US5288918A (en) | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
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DE19627204A1 (de) | 1996-07-05 | 1998-01-08 | Basf Ag | Kosmetische oder pharmazeutische Mittel zur Anwendung auf der Haut |
DE19741097A1 (de) | 1997-09-18 | 1999-03-25 | Basf Ag | Verfahren zur Copolymerisation von Ethylen mit Vinylcarboxylaten |
EP1383777B1 (de) | 2001-03-29 | 2005-11-16 | Basf Aktiengesellschaft | Liganden für pnicogenchelatkomplexe mit einem metall der viii. nebengruppe und verwendung der komplexe als katalysatoren für hydroformylierung, carbonylierung, hydrocyanierung oder hydrierung |
US6664356B1 (en) | 2003-01-23 | 2003-12-16 | Isp Investments Inc. | Leach resistant oil based carrier for cosmetically and pharmaceutically active agents |
GB0322247D0 (en) | 2003-09-23 | 2003-10-22 | Exxonmobil Chem Patents Inc | Improvement in or relating to an isobutylene containing stream |
DE102004012576A1 (de) | 2004-03-12 | 2005-09-29 | Basf Ag | Effektstoffe enthaltende wässrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
US20060024338A1 (en) | 2004-07-27 | 2006-02-02 | Hegedus Charles R | Cosmetic compositions incorporating vinyl acetate-ethylene polymers |
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EP1923454A1 (de) | 2006-11-17 | 2008-05-21 | Basf Se | Kaltfliessverbesserer |
KR101838767B1 (ko) | 2010-07-06 | 2018-03-14 | 바스프 에스이 | 화학적 균질성이 높은 공중합체 및 연료유의 저온 유동 특성을 향상시키기 위한 이의 용도 |
US8721744B2 (en) * | 2010-07-06 | 2014-05-13 | Basf Se | Copolymer with high chemical homogeneity and use thereof for improving the cold flow properties of fuel oils |
-
2015
- 2015-11-09 EP EP15791605.7A patent/EP3218419A1/en not_active Withdrawn
- 2015-11-09 JP JP2017524341A patent/JP2017533331A/ja active Pending
- 2015-11-09 CN CN201580060738.XA patent/CN107001523A/zh not_active Withdrawn
- 2015-11-09 US US15/525,084 patent/US9914792B2/en not_active Expired - Fee Related
- 2015-11-09 KR KR1020177014646A patent/KR20170084129A/ko unknown
- 2015-11-09 WO PCT/EP2015/076039 patent/WO2016075070A1/en active Application Filing
- 2015-11-09 CA CA2965228A patent/CA2965228A1/en not_active Abandoned
- 2015-11-09 BR BR112017009609A patent/BR112017009609A2/pt not_active Application Discontinuation
Also Published As
Publication number | Publication date |
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US20170335033A1 (en) | 2017-11-23 |
KR20170084129A (ko) | 2017-07-19 |
BR112017009609A2 (pt) | 2018-04-03 |
JP2017533331A (ja) | 2017-11-09 |
US9914792B2 (en) | 2018-03-13 |
WO2016075070A1 (en) | 2016-05-19 |
EP3218419A1 (en) | 2017-09-20 |
CA2965228A1 (en) | 2016-05-19 |
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