CN1058957C - 被取代的苯丙酸烷氧基亚烷基二醇酯及含有该化合物的组合物 - Google Patents
被取代的苯丙酸烷氧基亚烷基二醇酯及含有该化合物的组合物 Download PDFInfo
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- CN1058957C CN1058957C CN94102648A CN94102648A CN1058957C CN 1058957 C CN1058957 C CN 1058957C CN 94102648 A CN94102648 A CN 94102648A CN 94102648 A CN94102648 A CN 94102648A CN 1058957 C CN1058957 C CN 1058957C
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- 239000002253 acid Substances 0.000 title claims description 23
- 239000003963 antioxidant agent Substances 0.000 title abstract description 9
- 150000002148 esters Chemical class 0.000 title description 15
- -1 ethyleneoxy group Chemical group 0.000 claims abstract description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 14
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 20
- 239000004593 Epoxy Substances 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229920006037 cross link polymer Polymers 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 3
- 239000004695 Polyether sulfone Substances 0.000 claims description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920006393 polyether sulfone Polymers 0.000 claims description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 2
- 229920002050 silicone resin Polymers 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 abstract description 13
- 239000003381 stabilizer Substances 0.000 abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 31
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 20
- 150000001721 carbon Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000007859 condensation product Substances 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 11
- 229940017219 methyl propionate Drugs 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 235000019260 propionic acid Nutrition 0.000 description 10
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 235000006708 antioxidants Nutrition 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 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 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 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 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 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 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- PSEJBIODJNSJNT-UHFFFAOYSA-N CCCCC([O])=O Chemical compound CCCCC([O])=O PSEJBIODJNSJNT-UHFFFAOYSA-N 0.000 description 2
- LFZVVVZIFIRGFT-UHFFFAOYSA-N CCCCCCCCCCC.N1C=CC=CC=C1 Chemical compound CCCCCCCCCCC.N1C=CC=CC=C1 LFZVVVZIFIRGFT-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 238000010934 O-alkylation reaction Methods 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JFHGLVIOIANSIN-UHFFFAOYSA-N dimethyl butanedioate;1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound COC(=O)CCC(=O)OC.CC1(C)CC(O)CC(C)(C)N1CCO JFHGLVIOIANSIN-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000005826 halohydrocarbons Chemical class 0.000 description 2
- 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 2
- 239000003350 kerosene Substances 0.000 description 2
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/172—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
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Abstract
式I化合物:
式中:
R1代表具有1-6个碳原子的烷基;
R2代表具有8-24个碳原子的烷基;
EO代表亚乙基氧基;
PO代表亚丙基氧基;
K是0或1-10的整数;
m是0或1-5的整数;
条件是(k+m)的和大于0而且不大于10;其可用作聚合材料的抗氧化稳定剂。
Description
本发明涉及新的取代苯丙酸烷氧基亚烷基二醇酯及其作为易发生氧化变质的有机物质,如合成的聚合物和树脂的抗氧化稳定剂的用途。
通常必须向由有机聚合物和树脂制成的材料中掺入抗氧化剂以抑制氧化变质的影响。已知各种受阻酚酯,包括某些取代苯基链烷酸的亚烷基二醇酯可被用于该用途。例如英国专利1,376,482公开了带有单一或多个亚烷基二醇烷基单醚的3,5-二烷基-4-羟基苯基链烷酸酯和它们作为抗氧化剂的用途。但这些化合物中的烷基醚部分仅含有1或2个碳原子。
上述这种类型的已知抗氧剂大部分是具有相对高熔点的固体,这在聚合加工厂中会造成若干问题。这些抗氧剂的用量少并且难以保证它们在整个聚合材料中的均匀分散,因此它们可能具有差的可混性。当向一种液体聚合材料,如制备聚氨酯类或涂料的液体多元醇中添加固体抗氧剂时这类可混性问题尤为突出,为此需要易混的液体稳定剂。液体或低熔点固体稳定剂也更适用于现代合成树脂加工厂中的自动计量装置。
在现代聚烯烃加工厂中,固体稳定剂还带来其它问题,因为这些工厂倾向于取消将整体聚合物与稳定剂熔融混而代之以在液相中用稳定剂处理大粒径的聚合物颗粒,然后干燥。
因此需要新的有效的液态或低熔点固态抗氧剂以避免这类问题的干扰。
本发明的一个目的就是提供新的聚亚烷基二醇的取代的苯丙酸酯,这类化合物是聚合有机材料的有效抗氧剂。本发明的另一个目的是提供为液体或低熔点固体而且具有良好的聚合物可混性的这类酯,它们因此易于掺入整个聚合物材料中。本发明的再一个目的是提供具有优良的聚合材料抗氧化稳定剂活性的这类新的酯。
我们惊奇地发现某些单一或多个亚烷基二醇烷基单醚的取代苯丙酸酯(其中的烷基醚部分有8个或8个以上的碳原子)能解决上述问题。这些酯是液体或低熔点固体,具有良好的聚合物混溶性及出众的抗氧化活性,热稳定剂和耐氧化氮性,以及具有低挥发性和对表面迁移的下降趋向,因此本发明的第一个方面是提供下述式(I)化合物式中:
R1代表具有1-6个碳原子的烷基;
R2代表具有8-24个碳原子的烷基;
EO代表亚乙基氧基;
PO代表亚丙基氧基;
K是0或1-10的整数;和
m是0或1-5的整数;条件是(k+m)的和大于0但不超过10。
本发明还提供了含有至少一种上述式(I)化合物作为活性成份的有机聚合材料抗氧化剂。
在上述式(I)中,R1可以是具有1-6个碳原子的直链或支链烷基,如甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、戊基、异戊基、叔戊基、己基或异己基。较优选的R1代表具有1-4个碳原子的烷基;最优选的R1是甲基或叔丁基。
上式式(I)中的R2可以是具有8-24个碳原子的直链或支链烷基,如辛基、2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基或二十四烷基。优选的R2代表具有8-18个碳原子的直链或支链烷基,更优选的R2具有12-18个碳原子,最优选的R2具有16-18个碳原子。
式(I)中的{(EO)k+(PO)m}代表环氧乙烷、聚环氯乙烷、1,2-环氧丙烷或聚1,2-环氧丙烷,或者是一个或多个环氧乙烷基与一个或多个1,2-环氧丙烷基形成的混合加合物。对于这类环氧乙烷/1,2-环氧丙烷的混合加合物,就其环氧乙烷和1,2-环氧丙烷基加成度而言没有限制,指数k和m表示加合物中环氧乙烷和1,2-环氧丙烷单元的平均摩尔数。
式(I)中(k+m)的总和优选的是1-8,更优选的是1-6,最优选1-3。
优选的式(I)化合物的取代基是:
R1代表具有1-4个碳原子的直链或支链烷基;
R2代表具有8-18个碳原子的直链或支链烷基;
及(k+m)的和是1-8。
更为优选式(I)化合物的取代基是:
R1代表甲基或叔丁基:
R2代表具有12-18个碳原子的直链或支链烷基:及
(k+m)的和是1-6。
最为优选式(I)化合物是其式中:
R1代表叔丁基;
R2代表具有16-18个碳原子的直链或支链烷基;及
(k+m)的和是1-3。
式(I)化合物的某些典型实例列于表1,该表中使用的缩写含义如下:
Bu ……丁基 Me ……甲基
t-Bu ……叔丁基 Oc ……辛基
Dcs ……二十二烷基 Ocdc ……十八烷基
Ddc ……十二烷基 PO ……亚丙基氧基
EO ……亚乙基氧基 Pr ……丙基
Et ……乙基 i-Pr ……异丙基
Hx ……己基 Trdc ……十三烷基
Hxdc ……十六烷基 Ttcs ……二十四烷基
Ics ……二十烷基表1化合物.No. R1 [(EO)k+(PO)m] R21 Me [(EO)1] 2-Et-Hx2 Me [(EO)2] 2-Et-Hx3 Et [(EO)2] 2-Et-Hx4 Pr [(EO)2] 2-Et-Hx5 t-Bu [(EO)1] 2-Et-Hx6 t-Bu [(EO)2] 2-Et-Hx7 t-Bu [(EO)4] 2-Et-Hx8 t-Bu [(EO)8] 2-Et-Hx9 t-Bu [(PO)1] 2-Et-Hx10 t-Bu [(PO)2] 2-Et-Hx11 t-Bu [(EO)2+(PO)1] 2-Et-Hx12 t-Bu [(EO)2+(PO)2] 2-Et-Hx13 Me [(EO)1] Oc14 Me [(EO)2] Oc15 t-Bu [(EO)1] Oc16 t-Bu [(EO)2] Oc17 t-Bu [(EO)2] 3,5,5-Me3-Hx18 Me [(EO)1] Ddc19 Me [(EO)2] Ddc20 t-Bu [(EO)1] Ddt21 t-Bu [(EO)2] Ddc22 t-Bu [(EO)4] Ddc23 t-Bu [(EO)8] Ddc24 t-Bu [(PO)2] Ddc25 t-Bu [(EO)2] Trdc26 t-Bu [(PO)2] Trdc27 Me [(EO)1] Hxdc28 Me [(EO)2] Hxdc29 Me [(EO)3] Hxdc30 Me [(EO)4] Hxdc31 Me [(PO)1] Hxdc32 Me [(EO)2+(PO)1] Hxdc33 Et [(EO)2] Hxdc表1(续)化合物.No. R1 [(EO)k+(PO)m] R234 i-Pr [(EO)2] Hxdc35 t-Bu [(EO)1] Hxdc36 t-Bu [(EO)2] Hxdc37 t-Bu [(EO)3] Hxdc38 t-Bu [(EO)4] Hxdc39 t-Bu [(EO)6] Hxdc40 t-Bu [(EO)8] Hxdc41 t-Bu [(PO)1] Hxdc42 t-Bu [(PO)2] Hxdc43 t-Bu [[PO)3] Hxdc44 t-Bu [(EO)2+(PO)1] Hxdc45 t-Bu [(EO)3+(PO)1] Hxdc46 t-Bu [(EO)6+(PO)4] Hxdc47 Me [(EO)1] Ocdc48 Me [(EO)2] Ocdc49 Me [(EO)4] Ocdc50 Me [(PO)2] Ocdc51 Me [(EO)2+(PO)1] Ocdc52 t-Bu [(EO)1] Ocdc53 t-Bu [(EO)2] Ocdc54 t-Bu [(PO)3] Ocdc55 t-Bu [(PO)7] Ocdc56 t-Bu [(EO)8] Ocdc57 t-Bu [(EO)10] Ocdc58 t-Bu [(PO)2] Ocdc59 t-Bu [(PO)3] Ocdc60 t-Bu [(EO)2+(PO)1] Ocdc61 t-Bu [(EO)10+(PO)2] Ocdc62 t-Bu [(EO)2+(PO)2] Ocdc63 t-Bu [(EO)1] Ics64 t-Bu [(EO)2] Ics65 t-Bu [(EO)4] Ics66 t-Bu [(PO)2] Ics续表1化合物No. R1 [(EO)k+(PO)m] R267 t-Bu [(PO)4] Ics68 t-Bu [(EO)2+(PO)1] Ics69 t-Bu [(EO)2] Dcs70 t-Bu [(PO)2] Ttcs
在表1所列的化合物中编号如下的化合物是优选的:
7,8,11,16,18,19,20,21,22,23,24,25,26,27,28,29,31,32,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,62和64:其中编号为8,11,21,22,23,24,28,35,36,37,41,42,43,52,53,54,58和59的化合物更为优选。
本发明的化合物可用制备该类化合物的现有常规方法中的任何一种方法进行制备,这些方法包括各种酯化方法。这类方法中的三种实施例在下述反应路线图中举例说明,分别以方法A,方法B和方法C表示:1)方法A2)方法B3)方法C在上述反应路线图中:
R1,R2,K和m与前面在式(I)中的定义相同;
R3代表具有1-4个碳原子的直链或支链烷基,例如:甲基、乙基、丙基、异丙基、丁基或异丁基,优选代表甲基;
X代表卤原子,例如氯原子或溴原子。
式(II)的原料是亚烷基氧化物与各种醇的加合物,可将其记为亚烷基二醇烷基单醚或O-烷基化亚烷基二醇。可以知道,对于聚烯化氧加合物而言,市售的产品经常是具有变化的环氧乙烷和/或1,2-环氧丙烷单元数的一些单一化合物的混合物;如果该混合物被用做原料,则式(I)的最终产物将由相应的混合物组成。因此可知在这类混合物中,指数K和m可以分别代表环氧乙烷和1,2-环氧丙烷单元的平均数,对于混合物整体而言它们可能是分数。方法A涉及式(II)亚烷基二醇单醚与式(IIIa)取代的苯丙酸酯的酯基转移作用。该反应可根据需要在存在溶剂或没有溶剂及在酯基交换催化剂存在的条件下进行。
如果该反应使用一种溶剂,适宜的惰性溶剂包括:例如,如二异丙基醚,二噁烷和四氢呋喃的醚,如四氯化碳和二氯乙烷的卤代烃,如己烷、庚烷、辛烷、异辛烷、环己烷、甲基环己烷、乙基环己烷和煤油的直链或环脂族烃,如苯、甲苯和二甲苯的芳烃。芳烃是优选的。
适宜的酯基交换催化剂包括:例如,如锂、钠和钾的碱金属,如氨基化锂、氨基化钠和N,N-二异丙基氨基化锂的碱金属氨基化物,如甲醇钠、乙醇钠和叔丁醇钾的碱金属醇盐,如氢氧化锂,氢氧化钠和氢氧化钾的碱金属氢氧化物,如碳酸锂、碳酸钠和碳酸钾的碱金属碳酸盐,如碳酸氢锂、碳酸氢钠和碳酸氢钾的碱金属碳酸氢盐,如四异丙醇钛(IV)和四丁醇酞(IV)的钛(IV)的醇盐,以及如氧化锡的氧化金属盐。优选碱金属醇盐。
反应的温度和时间可依据使用的原料、催化剂和溶剂(如果看的话)而变化。但通常使用的温度为50℃-200℃;更为优选的是80℃-140℃:反应时间通常为2-24小时,更优选的是4-12小时。
酯基交换反应完成后所需的式(I)产物可用常规的技术方法进行分离。例如,用稀无机酸(如稀盐酸或硫酸)洗涤和中和反应混合物,(如用过滤)除去不溶物,所得液体用脱水剂(如无水硫酸镁),干燥并蒸去溶剂。如果需要可通过如减压蒸馏或柱层析提纯所得产物。方法B涉及亚烷基二醇单醚(式(II))与式(IIIb)的取代苯基丙酸的酯化反应。该反应通常在一种惰性溶剂中和在一种酸催化剂存在下进行。
可用于该反应的适宜溶剂包括:例如,如二异丙醚、二噁烷和四氢呋喃的醚,如二氯甲烷,四氯化碳和二氯乙烷的卤代烃,如己烷、庚烷、辛烷、乙基环己烷和煤油的脂族烃,以及如苯、甲苯和二甲苯芳烃。芳烃是优选的。
可用于该反应的酸催化剂包括:例如,如苯磺酸、对-甲苯磺酸、三氟甲磺酸和甲磺酸的磺酸,以及如盐酸和硫酸的无机酸,优选的是无机酸和磺酸,如硫酸这样的无机酸和如对-甲苯磺酸这样的磺酸是更优选的。
反应的温度和时间可依据原料、溶剂和催化剂而变化,但温度通常为60℃-200℃,100℃-150℃更为优选,反应时间通常为3-24小时,更优选的是4-12小时。
酯化反应完成后,可用常规技术分离所需的式(I)产物。例如:用碱的水溶液(如碳酸氢钠水溶液)洗涤和中和反应混合物,除去(如用过滤)不溶物,所得液体用脱水剂(如无水硫酸镁)干燥,蒸去溶剂得到式(I)产物。如果需要,可通过减压蒸馏或柱层析提纯该产物。方法C涉及式(II)亚烷基二醇单醚与式IIIc的取代苯丙酰卤的酯化反应。该反应通常在一种惰性溶剂中和在卤化氢去除剂的存在下进行。
用于该反应的适宜溶剂的实例包括已列于上述方法A的反应中的那些溶剂。
适宜的卤化氢去除剂的实例包括如氢氧化锂、氢氧化钠和氢氧化钾的碱金属氢氧化物,如碳酸锂、碳酸钠和碳酸钾的碳金属碳酸盐,如碳酸氢锂、碳酸氢钠和碳酸氢钾的碱金属碳酸氢盐,如三乙胺、三辛胺、N-甲基吗啉和N,N-二甲基哌嗪的脂族叔胺,以及如吡啶和N,N-二甲基氨基吡啶的吡啶类。优选的是三乙胺和吡啶类。
反应时间和温度可依据原料,溶剂和使用的卤化氢去除剂而变化。但反应温度通常为0℃-120℃;更为优选的为10℃-60℃;反应时间选常为1-12小时,更优选的是4-8小时。
反应完成后可用常规技术方法分离所需的式(I)产物。例如可用稀无机酸(如稀盐酸或硫酸)洗涤反应混合物,除去(如用过滤)不溶物,所得液体用脱水剂(如无水硫酸镁)干燥并蒸去溶剂得到所需产物。如果需要可用如减压蒸馏或柱层析提纯该产物。
我们已经发现式(I)化合物具有出众的聚合物可混性、热稳定性和耐氧化氮性,以及低挥发性和对于表面迁移的下降趋向。这些性能的总和使得它们成为有机材料,如脂肪、润滑油和聚合材料的新的有价值的抗氧化稳定剂。
本发明的抗氧化化合物可用已知技术手段,在任何适当阶段掺入将被稳定化的有机材料中。例如可在聚合前或聚合后或在如注模的加工步骤中将其加入。例如,可将抗氧剂与粒状或粒末状聚合材料混合;或将抗氧剂的溶液或悬浮液与聚合材料混合,并将该混合物干燥;或将该抗氧剂与液体单体,多元醇、异氰酸酯、增塑剂或预聚物混合,然后将所得的预混物与聚合材料混合。本发明的抗氧化剂也可与聚合物技术领域常规使用的其它添加剂一起使用。
适于与本发明的抗氧化稳定剂一起使用的合成树脂和聚合材料包括:烯烃和二烯烃聚合物
烯烃和二烯烃的均聚物(如低密度、线性低密度、高密度和交联聚乙烯、聚丙烯、聚异丁烯、聚甲基丁烯-1、聚甲基戊烯-1、聚异戊二烯和聚丁二烯);这些均聚物的混合物(如聚丙烯和聚乙烯的混合物,聚丙烯和聚异丁烯-1的混合物及聚丙烯和聚异丁烯的混合物);烯烃的共聚物(如乙烯-丙烯共聚物、丙烯-丁烯-1共聚物和乙烯-丁烯-1共聚物);烯烃和二烯烃的共聚物(如乙烯、丙烯和如丁二烯、己二烯、二环戊二烯和亚乙基降冰片烯的二烯烃的三聚物);和天然橡胶;
苯乙烯聚合物
聚苯乙烯、聚α-甲基苯乙烯和苯乙烯或α-甲基苯乙烯的共聚物(如苯乙烯-马来酸酐共聚物、苯乙烯-丁二烯共聚物、苯乙烯-丙烯腈-甲基丙烯酸甲酯共聚物、苯乙烯-丙烯腈-丙烯酸酯共聚物、用丙烯酸酯进行冲击强度改性的苯乙烯-丙烯腈共聚物、用乙烯丙烯二烯单体进行冲击强度改性的苯乙烯聚合物);苯乙烯的接枝聚物[如:苯乙烯和聚丁二烯的接枝共聚物、苯乙烯与丙烯腈对聚丁二烯的接枝共聚物(通常指丙烯腈-丁二烯-苯乙烯聚合物)、这些接枝共聚物与上述苯乙烯共聚物的混合物]和耐热丙烯腈-丁二烯-苯乙烯聚合物与马来酰亚胺衍生物的共聚产物;乙烯基卤、偏二卤乙烯及卤代烯烃聚合物
聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏氟乙烯、氯丁橡胶、氯乙烯-偏二氯乙烯共聚物、氯乙烯-乙酸乙烯酯共聚物、氯乙烯-乙烯共聚物、偏二氯乙烯-乙酸乙烯酯共聚物、氯化聚乙烯、氯化聚丙烯、聚氯三氟乙烯和聚四氟乙烯;α,β不饱和酸及其衍生物的聚合物
聚丙烯酸酯、聚甲基丙烯酸酯、聚丙烯酰胺和聚丙烯腈;不饱和醇和不饱和胺或它们的酰基衍生物或醛缩醇的聚合物
聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯或聚烯丙基三聚氰胺,以及这些单体与其它乙烯基化合物的共聚物(如乙烯-乙酸乙烯酯共聚物);聚亚烷基氧化物和聚亚苯基氧化物
聚氧化亚甲基、氧化亚甲基-环氧乙烷共聚物、聚氧化乙烯、聚氧化丙烯、聚氧化异丁烯和聚苯氧;改性纤维素
乙酸纤维素、乙酸丁酸纤维素、乙酸丙酸纤维素、丙酸纤维素、硝基纤维素和乙基纤维素;聚酰胺和共聚酰胺
由二胺和脂族酸或芳族二元羧酸衍生和/或由氨基羧酸或相应的内酰胺衍生的聚酰胺和共聚酰胺 (如尼龙6,尼龙6/6,尼龙6/10,尼龙11和尼龙12)。聚酯
由二元羧酸和二元醇衍生和/或由羟基酸或相应的内酯衍生的聚酯(如聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚对苯二甲酸环己烷-1,4-二甲酯;聚碳酸酯,聚酯碳酸酯、聚醚酰亚胺、聚醚酮、聚醚砜、聚亚苯基硫化物、聚砜和硅氧烷树脂聚氨酯和聚脲交联聚合物
交联聚合物其由衍生自醛的部分和衍生自苯酚、脲或三聚氰胺的另一部分组成(如酚醛树脂、脲-甲醛树脂、蜜胺-甲醛树脂和邻苯二甲酸二芳基酯树脂);环氧聚合物
环氧化合物的均聚物和共聚物(如聚环氧乙烷);二缩水甘油醚化合物的聚合物;醇酸树脂
丙三醇-邻苯二甲酸树脂及其与蜜胺-甲醛树脂的混合物;不饱和聚酯树脂
由饱和的和不饱和的二元羧酸与多元醇的共聚多酯衍生而来的和用乙烯基化合物做交联剂制得的不饱和聚酯树脂;以及用氯化进行增加阻燃性改性的不饱和聚酯树脂。
为取得所需稳定效果而必须的本发明稳定剂的用量可依据本领域技术人员所清楚的一系列因素而改变。需要考虑的典型因素包括被稳定化的聚合物的种类,性能及预计的用途,特别是是否使用其它添加剂。通常我们优选使用以聚合物重量计的约0.01-约5%(wt)的本发明的稳定剂。
如上所述的优选用量随聚合物种类改变。例如,对于烯烃,二烯烃和苯乙烯聚合物,适宜的稳定剂用量为约0.01-约2.0%(wt),优选的为约0.05-约2.0%(wt);对于氯乙烯和亚乙烯基二氯聚合物,适宜的用量为约0.01-约5.0%(wt):优选用量为约0.05-约2.0%(wt);对于聚氨基甲酸乙酯和聚酰聚合物,适宜的用量为约0.01-约5.0%(wt);优选用量为约0.05-约2.0%(wt);。
可以知道,根据需要可将本发明的两种或两种以上的稳定剂结合使用或与其它添加剂结合使用。
在聚合物技术领域中习惯采用的各种添加剂可适当地与本发明的稳定剂一同被添加或单独被添加。这类适宜的添加剂包括,例如:苯酚抗氧化剂
2,6-二叔丁基-对-甲苯酚;硬脂基-β-(4-羟基-3,5-二叔丁苯基)丙酸酯;二硬脂基(4-羟基-3-甲基-5-叔丁基苄基)丙二酸酯;2,2’-亚甲基双-(4-甲基-6-叔丁基苯酚);4,4-亚甲基双(2,6-二叔丁基苯酚;2,2’-亚甲基双-[6-(1-甲基环己基)-对甲苯酚;双[3,3-双(4-羟基-3-叔丁基苯基)丁酸]乙二醇酯;4,4’-亚甲基双-(6-叔丁基-间-甲苯酚);1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷;1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲苯;3,9-双[1,1-二甲基-2-(3,5-二叔丁基-4-羟基苯基)乙基]-2,4,8,10-四氧杂螺[5.5]十一烷;四-[3-(3,5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯:1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰尿酸酯;1,3,5-三[(3,5-二叔丁基-4-羟基苯基)丙酰基氧乙基]异氰尿酸酯;和双[3-(3,5-二叔丁基-4-羟基苯基)丙酰基]草酰胺。硫酯稳定剂
硫代二丙酸二月桂酯,硫代二丙酸二肉豆蔻酯,硫代二丙酸二硬脂基酯和四(十二烷基硫代丙酸)季戊四醇酯。亚磷酸酯稳定剂
三(2,4 -二叔丁基苯基)亚磷酸酯;亚磷酸三苯酯:亚磷酸三-壬基苯基酯;二硬脂基季戊四醇二亚磷酸酯:4,4亚丁基双(3-甲基-6-叔丁基苯基-二-十三烷基)亚磷酸酯:双(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯;和四(2,4-叔丁基苯基)4,4-亚联苯基亚膦酸酯位阻胺光稳定剂
4-苯甲酰氧基-2,2,6,6-四甲基哌啶;
4-硬脂酰氧基-2,2,6,6-四甲基哌啶;
4-甲基丙烯酰氧基-2,2,6,6-四甲基哌啶;
4-甲基丙烯酰氧基-1,2,2,6,6-五甲基哌啶;
二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯;
二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯;
二(2,2,6,6-四甲基-1-辛氧代-4-哌啶基)癸二酸酯;
2-甲基-2-(2,2,6,6-四甲基-4-哌啶基)亚氨基-N-(2,2,6,6-四甲基-4-哌啶基)丙酰胺;
2-甲基-2-(1,2,2,6,6-五甲基-4-哌啶基)亚氨基-N-(1,2,2,6,6-五甲基-4-哌啶基)丙酰胺;
1-丙烯酰基-4-苄氧基-2,2,6,6-四甲基哌啶;
二(1,2,2,6,6-五甲基-4-哌啶基)-2-丁基-2-(3,5-二叔丁基-4-羟基苄基)丁基丙二酸酯;
8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮;
四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
四(1,2,2,6,6-五甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
十三烷基-三(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
十三烷基-三(1,2,2,6,6-五甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
4-{3-(3,5-二叔丁基-4-羟基苯基)丙酰氧基}-1-[2-{3-(3,5-二叔丁基-4-羟基苯基)丙酰氧基}乙基]2,2,6,6-四甲基哌啶;
二(十三烷基)-二(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
二(十三烷基)-二(1,2,2,6,6-五甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
3,9-二(1,1-二甲基-2-{2,2,6,6-四甲基-4-哌啶氧基羰基)丁基羰氧基}乙基]-2,4,8,10-四氧杂螺[5.5]十一烷;
3,9-二(1,1-二甲基-2-(三-{1,2,2,6,6-五甲基-4-哌啶氧基羰基)丁基羰氧基}乙基]-2,4,8,10-四氧杂螺[5.5]十一烷;
琥珀酸二甲酯4-羟基-1-(2-羟乙基)2,2,6,6-四甲基哌啶缩聚产物;
聚[乙烯{(2,2,6,6-四甲基-4-哌啶基)-亚氨基}六亚甲基{(2,2,6,6-四甲基-4-哌啶基)亚氨基}];
聚[{6(1,1,3,3-四甲基丁基)氨基-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)-亚氨基}-六亚甲基{(2,2,6,6-四甲基-4-哌啶基)-亚氨基}];
聚[{6(环己基氨基)-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亚氨基}六亚甲基{(2,2,6,6-四甲基-4-哌啶基)亚氨基}];
聚[{6(吗啉代)-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亚氨基}六亚甲基{(2,2,6,6-四甲基-4-哌啶基)亚氨基}];
1,6,11-三[{4,6-二(N-丁基-N-(2,2,6,6-四甲基-4-哌啶基)氨基-1,3,5-三嗪-2-基}氨基]氮杂十一烷;
1,6,11-三[{4,6-二(N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)氨基-1,3,5-三嗪-2-基}氨基]氮杂十一烷;
1,5,8,12-四[4,6-二{N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)氨基-1,3,5,-三嗪-2-基]-1,5,8,12-四氮杂十二烷;和
聚甲基丙基-3-氧代[4-(2,2,6,6-四甲基)-哌啶基]硅氧烷。特别优选的是:
二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯;
二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯;
四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯;
四(1,2,2,6,6-五甲基-4-哌啶基)-1,2,3,4,-丁烷四甲酸酯:
琥珀酸二甲酯4-羟基-1-(2-羟乙基)2,2,6,6-四甲基哌啶缩聚产物;
聚[{6(1,1,3,3-四甲基丁基)氨基-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)-亚氨基}-六亚甲基{(2,2,6,6-四甲基-4-哌啶基)-亚氨基}];
聚[{6-吗啉代-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亚氨基}六亚甲基{(2,2,6,6-四甲基-4-哌啶基)亚氨基}];和
1,5,8,12-四{4,6-二(N-1,2,2,6,6-五甲基-4-哌啶基)丁氨基-1,3,5,-三嗪-2-基]-1,5,8,12-四氮杂十二烷。紫外吸收剂
2,4-二羟基二苯酮;2-羟基-4-甲氧基二苯酮;2-羟基-4-甲氧基二苯酮-5-磺酸;2-羟基-4-辛氧代二苯酮;2-羟基-4-十二烷基氧代二苯酮;2-羟基-4-苄基氧代二苯酮;二(5-苯甲酰基-4-羟基-2-甲氧基苯基)甲烷;2,2’-二羟基-4-甲氧基二苯酮;2,2’-二羟基-4,4’-二甲氧基二苯酮;2,2’,4,4’-四羟基二苯酮;2-羟基-4-甲氧基-2’-羧基二苯酮;2-(2’-羟基-5’-甲苯基)苯并三唑;2-[2’-羟基-3’,5’-二(α,α-二甲基苄基)苯基]苯并三唑;2-(2’-羟基-3’,5’-二叔丁基苯基)苯并三唑;2-(2’-羟基-3’-叔丁基-5’-甲基苯基)-5-氯代苯并三唑;2-(2’-羟基-3’,5’-二-叔丁基苯基)-5-氯代苯并三唑;2-(2’-羟基-3’,5’-二-叔戊基苯基)苯并三唑;2-(2’-羟基-5’-叔辛基苯基)苯并三唑;2,2’-亚甲基-二[4-(1,1,3,3-四甲基丁基)-6-(2-N-苯并三唑-2-基)苯酚];甲基-3-[3-叔丁基-5-(2H-苯并三唑-2-基)-4-羟基苯基]丙酸酯和聚乙二醇的缩合产物;和2-(2-羟苯基)苯并三唑共聚物。羟基苯甲酸酯光稳定剂
3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯基酯,
3,5-二叔丁基-4-羟基苯甲酸2,6-二叔丁基苯基酯和3,5-二-叔丁基-4-羟基苯甲酸十六烷基酯。含镍稳定剂
一乙基-3,5-二-叔丁基-4-羟基苄基膦酸镍:丁胺-镍-2,2’-硫代双-(4-叔辛基苯甲酸盐)配合物;二丁基-二硫代氨基甲酸镍;和3,5-二叔丁基-4-羟基苯甲酸镍。高级脂肪酸的金属盐
硬脂酸的钙、镁、钡、锌、镉、铅或镍盐,和月桂酸的钙、镁、镉、钡、或锌盐。
上面所到各种添加剂可根据预计的用途来决定单独使用或两种或两种以上结合使用。
本发明的稳定剂也可与下面这些试剂结合使用,这些试剂如:重金属减活化剂、成核试剂、有机锡化合物、增塑剂、环氧化合物、颜料、涂料、荧光增白剂、填充剂、助剂、起泡剂、抗静电剂、防霉剂或杀菌剂、润滑剂和加工助剂。
掺有本发明稳定剂的聚合物可根据需要以下述形式使用,例如以膜、片、纤维、楔形、挤压成型材料、注模材料、涂敷组合物、密封材料或粘合剂。
现对本发明的实施方案用实施例和对比实施例进行更为完整的说明,但它们并不限定本发明的范围。在这些实施例和对比实施例中,使用的“份”和“%”分别意味着重量份或重量百分比(除非另有说明)。
实施例中使用的原料是烯化氧与各种醇的加合物,可记为亚烷基二醇单醚或O-烷基化亚烷基二醇。这些原料为市售或可用己知方法制备,已知方法如”Synthesis and Applicalions of SurfaceActive Agents”(Ryohei Oda和Kazuhiro Teramura 13th Edition(1972),Maki Publishing Co.Ltd.,Japan.出版)的141-142页所述。如前所释,市售加合物可以是具有变化的环氧乙烷和/或环氧丙烷单元数的若干单一化合物,因此在该化合物中标出的单元数可代表在这样一种混合物中的平均数。
实施例1
2-{2-[2-(2-乙基己氧基)乙氧基]乙氧基}丙基3-(3,5-二叔丁基-4-羟基苯基)丙酸酯
将50ml甲苯、12.51g 3-(3,5-二叔丁基-4-羟基苯基)丙酸,8.29g O-(2-乙基己基)二甘醇与1mol环氧丙烷的加合物,和0.16g对甲苯磺酸组成的混合物在搅拌下回流加热6小时,然后蒸去生成的水。使反应混合物冷却,用5%碳酸钠水溶液和水洗涤。减压下除去甲苯,得到13.6g浅黄色油状标题化合物,nD 20=1.4885。
实施例2
O-(2-乙基己基)八(乙二醇)和3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯的缩合产物
将370ml二甲苯、92.1g 3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯,145.6g的2-乙基己基醇与环氧乙烷(1∶8摩尔比)的加合物和0.5g原钛酸四异丙酯的混合物在搅拌下回流加热3.5小时,然后蒸去形成的甲苯和甲醇混合物。将反应混合物冷却然后用30ml水洗涤。减压除去二甲苯得到浅黄色油状标题化合物215.5g,nD 20=1.4845。
实施例3
O-十二烷基二甘醇和3-(3,5-二叔丁基-4-羟基苯基)丙酸的缩合产物
通过与实施例1相似的方法用十二烷基醇和环氧乙烷(1∶2摩尔比)制得标题化合物,该化合物为浅黄色油状物,nD 20=1.4877。
实施例4
O-十二烷基二亚丙基二醇和3-(3,5-二-叔丁基-4-羟基苯基)丙酸的缩合产物
用与实施例1类似的方法,用十二烷基醇和1,2-环氧丙烷(1∶2摩尔比)制得油状标题化合物,nD 20=1.4831。
实施例5
O-十二烷基八(乙二醇)和3-(3,5-二叔丁基-4-羟基苯基)丙酸酯
将40ml甲苯、1.08g 3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯,2.0g O-十二烷基八(乙二醇)(比重0.889 20/4℃,Wako Pure Chemical Industries,Ltd出品)和0.1g原酞酸四异丙酯组成的混合物在搅拌下加热回流7小时,然后将形成的甲苯和甲醇混合物蒸去。将反应混合物冷却,然后过滤。向滤液中加入水,用20ml乙酸乙酯将反应产物萃取三遍。萃取液用无水硫酸镁干燥并浓缩。用柱层析提纯该残余物(乙酸乙酯/正己烷=1/3洗脱),得到2.15g油状标题化合物,nD 20=1.4823。元素分析:C45H62O11 理论值 C:67.63%;H:10.34%
实验值 C:67.35%;H:10.36%
实施例6
O-十六烷基乙二醇和3-(3,5-二-叔丁基-4-羟基苯基)丙酸的缩合产物
用与实施例1相似的方法,用十六烷基醇和环氧乙烷(1∶1摩尔比)制备,得到油状标题化合物,nD 20=1.4868。
实施例7
O-十六烷基二甘醇与3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯的缩合产物
将150ml甲苯、53.5g 3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯,60.0g的十六烷醇与环氧乙烷(1∶2摩尔比,nD 20=1.4428)加合物和0.9g原钛酸四异丙酯组成的混合物在搅拌下加热回流10小时,蒸去形成的甲苯与甲醇的混合物。向反应混合物中加入水(8.3ml),所得混合物在回流下搅拌1小时,然后蒸去水和甲苯。过滤该反应混合物,减压浓缩滤液得到101.6g淡黄色油状标题化合物,nD 20=1.4867。
实施例8
O-十六烷基三甘醇和3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯的缩合产物
用与实施例7相似的方法,用十六烷基醇和环氧乙烷(1∶3摩尔比)的加合物制得到油状标题化合物,nD 20=1.4850。
实施例9
O-十六烷基二(丙二醇)与3-(3,5-二-叔丁基-4-羟基苯基)丙酸的缩合产物
根据与实施例1相似的方法,用十六烷基醇与1,2-环氧丙烷(1∶2摩尔比)制得淡黄色油状标题化合物,nD20=1.4800。
实施例10
O-十六烷基二甘醇与3-(3-叔丁基-4-羟基-5-甲基苯基)丙酸甲酯的缩合产物
将30ml甲苯、7.5g 3-(3-叔丁基-4-羟基-5-甲基苯基)丙酸甲酯,10g的十六烷醇与环氧乙烷(1∶2摩尔比,nD 45=1.4428)加合物与0.02g甲醇钠组成的混合物在搅拌下加热回流6小时,然后将形成的甲苯和甲醇的混合物蒸去。使反应混合物冷却,然后用5%硫酸水溶液中和,水洗两遍,无水硫酸钠干燥和浓缩,得到15.7g油状标题化合物,nD 20=1.4887。
实施例11
O-十八烷基二甘醇与3-(3,5-二叔丁基-4-羟基苯基)丙酸的缩合产物
用与实施例1相似的方法,用十八烷基醇和环氧乙烷(1∶2摩尔比)的加合物制得到油状标题化合物,nD 20=1.4855。
实施例12
O-十八烷基二(丙二醇)与3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯的缩合产物
用与实施例10相似的方法,用十八烷基醇和 1,2-环氧丙烷(1∶2摩尔比)的加合物制得浅黄色油状标题化合物,nD 20=1.4805。
实施例13
O-十八烷基三(丙二醇)与3-(3,5-二-叔丁基-4-羟基苯基)丙酸的缩合产物
用与实施例1相似的方法,用十八烷基醇和1,2-环氧丙烷(1∶3摩尔比)的加合物制得浅黄色油状标题化合物,nD 20=1.4783。
实施例14
热稳定性试验
将熔体流动速率为约4.0的未稳定化的聚丙烯粉末与0.1%抗氧化剂(列于表2)在200℃下于混合器(LaboplastoTM mill,Toyo Seiki Seisakusho制造)内捏合10分钟至均一。将所得均相制品立即滚压成的2-3mm厚的片(使用水冷水压机)。
将该片的一部分切下并在挤压机中于240℃挤压4分钟制得0.5mm厚的片。从该0.5mm厚的片上切下10×100mm的试验条,将其放置在130℃烘箱中并记录天数,直至氧化降解(变白)发生。所得结果列于表2。
在表2中,本发明的化合物通过参照表1中所列化合物的编号和举例说明其制备的上述实施例进行识别。对比化合1和2是在下述对比实施例1和2中分别到得的化合物,它们构成了GB专利1,376,482公开的现有技术的一部分。表2 实验化合物 实施例
化合物编号
在130℃的耐热(天数)实施例1 No.11 11实施例2 No.8 13实施例3 No.21 10实施例4 No.24 12实施例5 No.20 10实施例6 No.35 18实施例7 No.36 26实施例8 No.37 22实施例9 No.42 25实施例10 No.28 21实施例11 No.53 29实施例12 No.58 26实施例13 No.59 16对比化合物1 5对比化合物2 4
对比实施例1
3-(3,5-二叔丁基-4-羟基苯基)丙酸2-甲氧基乙酯
用90g甲苯、102.4g 3-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯,18.2g乙二醇单甲基醚和0.35g甲醇钠,按照与实施例10类似的方法制得标题化合物42.2g,熔点为62-64℃。
对比实施例2
3-(3,5-二-叔丁基-4-羟基苯基)丙酸2-甲氧基丙酯
用3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯和丙二醇单甲基醚,按照与实施例10相似的方法制得白色粉末状标题化合物,熔点73-74℃。
Claims (10)
2.权利要求1的化合物,其中
R1代表具有1-4个碳原子的烷基;
R2代表具有8-18个的碳原子的烷基;和
(k+m)的和是1-8。
3.权利要求1的化合物,其中:
R1代表甲基或叔丁基;
R2代表具有12-18个的碳原子的烷基;和
(k+m)的和是1-6。
4.权利要求1的化合物,其中:
R1代表叔丁基;
R2代表具有16-18个的碳原子的烷基;和
(k+m)的和是1-3。
R1代表具有1-6个碳原子的烷基;
R2代表具有8-24个碳原子的烷基;
EO代表亚乙基氧基;
PO代表亚丙基氧基;
k是0或1-10的整数;
m是0或1-5的整数;其条件是(k+m)的和大于0并且不大于10。
该聚合物A包括以下聚合物:烯烃聚合物、二烯烃聚合物、苯乙烯聚合物、乙烯基卤、偏二卤乙烯和卤代烯烃聚合物、α、β-不饱和酸的聚合物和它们的衍生物、不饱和醇和不饱和胺或它们的酰基衍生物或醛缩醇的聚合物、聚亚烷基氧化物和聚亚苯基氧化物、改性纤维素、聚酰氨和共聚酰胺、聚酯、聚碳酸酯、聚酯碳酸酯、原醚酰亚胺、聚醚酮、聚醚砜、聚亚苯基硫化物、聚砜和硅氧烷树脂、聚氨酯和聚脲交联聚合物、环氧聚合物、醇酸树脂;和不饱和的聚酯树脂。
6.权利要求5的组合物,其中该聚合材料选自烯烃聚合物、二烯烃聚合物、苯乙烯聚合物、乙烯基卤和偏二卤乙烯聚合物、聚氨酯和聚酰氨。
7.权利要求5的组合物,其含有所述式(I)化合物,其中:
R1代表具有1-4个碳原子的烷基;
R2代表具有8-18个的碳原子的烷基;和
(k+m)的和是1-8。
8.权利要求5的组合物,其含有所述式(I)化合物,其中:
R1代表甲基或叔丁基;
R2代表具有12-18个的碳原子的烷基;和
(k+m)的和为1-6。
9.权利要求5的组合物,其含有所述式(I)化合物,其中:
R1代表叔丁基;
R2代表具有16-18个的碳原子的烷基;和
(k+m)的和为1-8。
10.权利要求5的组合物,其中所含有的式(I)化合物的重量按所述聚合材料的重量计为0.01%-5%。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP8437/93 | 1993-01-21 | ||
JP843793 | 1993-01-21 |
Publications (2)
Publication Number | Publication Date |
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CN1095057A CN1095057A (zh) | 1994-11-16 |
CN1058957C true CN1058957C (zh) | 2000-11-29 |
Family
ID=11693109
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Application Number | Title | Priority Date | Filing Date |
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CN94102648A Expired - Fee Related CN1058957C (zh) | 1993-01-21 | 1994-01-21 | 被取代的苯丙酸烷氧基亚烷基二醇酯及含有该化合物的组合物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5739377A (zh) |
EP (1) | EP0608089B1 (zh) |
KR (1) | KR0183121B1 (zh) |
CN (1) | CN1058957C (zh) |
CA (1) | CA2113852A1 (zh) |
DE (1) | DE69406153T2 (zh) |
HK (1) | HK1002256A1 (zh) |
TW (1) | TW261632B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105968339A (zh) * | 2015-03-10 | 2016-09-28 | 赢创德固赛有限公司 | 用于制备低排放pur 体系的抗氧化剂 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2302707A1 (en) * | 1997-09-30 | 1999-04-08 | Rosemarie A. Boccuzzi | Stabilized polyether polyol and polyurethane foam obtained therefrom |
US6291723B1 (en) | 1999-09-02 | 2001-09-18 | Borden Chemical, Inc. | Diolefin/hydroxyaryl condensates and catalyst therefor |
EP1292560B1 (de) * | 2000-06-23 | 2006-03-15 | Ciba SC Holding AG | Verfahren zur herstellung von hydroxyphenylcarbonsäureestern |
TW589760B (en) * | 2001-08-09 | 2004-06-01 | Sumitomo Chemical Co | Polymer electrolyte composition and fuel cell |
US9117268B2 (en) * | 2008-12-17 | 2015-08-25 | Digimarc Corporation | Out of phase digital watermarking in two chrominance directions |
EP3061746B1 (en) * | 2015-02-24 | 2016-12-07 | Founder Fine Chemical Industry Co., Ltd. | Hydrophilic antioxidant and process for the preparation of the same |
CN114805929B (zh) * | 2021-01-21 | 2023-03-21 | 天津利安隆新材料股份有限公司 | 一种复合液体抗氧剂及其制备方法 |
WO2024170610A1 (en) | 2023-02-17 | 2024-08-22 | Basf Se | Process for the preparation of hydroxyphenylcarboxylic acid esters using catalytic transesterification |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3629354A1 (de) * | 1986-08-28 | 1988-03-03 | Balco Precision Gmbh | Durch galvanoformung hergestelltes sieb fuer zentrifugen |
Family Cites Families (7)
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CH549407A (de) * | 1970-07-06 | 1974-05-31 | Ciba Geigy Ag | Verwendung sterisch gehinderter phenolestern von glykolen als stabilisatoren. |
US4032562A (en) * | 1974-11-05 | 1977-06-28 | Ciba-Geigy Corporation | 3,5-dialkyl-4-hydroxyphenylalkanoic acid esters of polyalkylene glycols |
DE3639354A1 (de) * | 1986-11-18 | 1988-06-01 | Huels Chemische Werke Ag | Ester von 3-tert.-butyl- bzw. 3-tert.-butyl-5-alkyl-4-hydroxyphenyl-(alkan)-carbonsaeuren mit oxethylaten monofunktioneller alkohole und phenole, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren organischer polymerer |
JPH02133374A (ja) * | 1988-11-11 | 1990-05-22 | Hitachi Chem Co Ltd | 炭素製品の製造法 |
US5206414A (en) * | 1990-01-11 | 1993-04-27 | Ciba-Geigy Corporation | Process for the preparation of hydroxyphenylpropionic acid esters |
US5427591A (en) * | 1992-12-18 | 1995-06-27 | Chevron Chemical Company | Poly(oxyalkylene) hydroxyaromatic esters and fuel compositions containing the same |
TW406127B (en) * | 1992-12-21 | 2000-09-21 | Ciba Sc Holding Ag | Novel liquid phenolic antioxidants |
-
1994
- 1994-01-17 EP EP94300291A patent/EP0608089B1/en not_active Expired - Lifetime
- 1994-01-17 DE DE69406153T patent/DE69406153T2/de not_active Expired - Fee Related
- 1994-01-20 CA CA002113852A patent/CA2113852A1/en not_active Abandoned
- 1994-01-21 CN CN94102648A patent/CN1058957C/zh not_active Expired - Fee Related
- 1994-01-21 KR KR1019940001121A patent/KR0183121B1/ko not_active IP Right Cessation
- 1994-01-21 TW TW083100522A patent/TW261632B/zh active
-
1995
- 1995-04-07 US US08/418,883 patent/US5739377A/en not_active Expired - Fee Related
-
1998
- 1998-02-18 HK HK98101255A patent/HK1002256A1/xx not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3629354A1 (de) * | 1986-08-28 | 1988-03-03 | Balco Precision Gmbh | Durch galvanoformung hergestelltes sieb fuer zentrifugen |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105968339A (zh) * | 2015-03-10 | 2016-09-28 | 赢创德固赛有限公司 | 用于制备低排放pur 体系的抗氧化剂 |
CN105968339B (zh) * | 2015-03-10 | 2020-03-27 | 赢创运营有限公司 | 用于制备低排放pur体系的抗氧化剂 |
Also Published As
Publication number | Publication date |
---|---|
KR940018350A (ko) | 1994-08-16 |
EP0608089B1 (en) | 1997-10-15 |
KR0183121B1 (ko) | 1999-05-15 |
DE69406153D1 (de) | 1997-11-20 |
CN1095057A (zh) | 1994-11-16 |
US5739377A (en) | 1998-04-14 |
DE69406153T2 (de) | 1998-05-20 |
EP0608089A1 (en) | 1994-07-27 |
TW261632B (zh) | 1995-11-01 |
HK1002256A1 (en) | 1998-08-07 |
CA2113852A1 (en) | 1994-07-22 |
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