CN1045102A - 四甲基哌啶基终止的三嗪低聚酯和酰胺 - Google Patents
四甲基哌啶基终止的三嗪低聚酯和酰胺 Download PDFInfo
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- CN1045102A CN1045102A CN89108964A CN89108964A CN1045102A CN 1045102 A CN1045102 A CN 1045102A CN 89108964 A CN89108964 A CN 89108964A CN 89108964 A CN89108964 A CN 89108964A CN 1045102 A CN1045102 A CN 1045102A
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- -1 Tetramethyl piperidyl Chemical group 0.000 title claims description 65
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000002148 esters Chemical class 0.000 title description 6
- 150000001408 amides Chemical class 0.000 title description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229920001059 synthetic polymer Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000001924 fatty-acyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- 230000006866 deterioration Effects 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 35
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 5
- 229920000620 organic polymer Polymers 0.000 claims 3
- 125000006309 butyl amino group Chemical group 0.000 claims 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 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 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- 238000005286 illumination Methods 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 6
- 230000000996 additive effect Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000005855 radiation Effects 0.000 abstract description 3
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- 150000005690 diesters Chemical class 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000000034 method Methods 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LUPBEAVDFFJJCT-UHFFFAOYSA-N 4-(4-chloro-1,3,5-triazin-2-yl)morpholine Chemical class ClC1=NC=NC(N2CCOCC2)=N1 LUPBEAVDFFJJCT-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920001542 oligosaccharide Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- XQQBZYGZRQYLBS-UHFFFAOYSA-N 4-tert-butyl-6-chloro-1,3,5-triazin-2-amine Chemical class C(C)(C)(C)C1=NC(=NC(=N1)Cl)N XQQBZYGZRQYLBS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 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 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 229920005613 synthetic organic polymer Polymers 0.000 description 5
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NRFOJVLXQQSBAQ-UHFFFAOYSA-N 3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propanoic acid Chemical compound CC1(C)CC(NCCC(O)=O)CC(C)(C)N1 NRFOJVLXQQSBAQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003490 Thiodipropionic acid Substances 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 235000019303 thiodipropionic acid Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000012434 nucleophilic reagent Substances 0.000 description 2
- 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 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- 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 2
- 238000010189 synthetic method Methods 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- RKSHALMLSDTBQX-UHFFFAOYSA-N 2-[(4-chloro-1,3,5-triazin-2-yl)amino]ethanol Chemical class OCCNC1=NC=NC(Cl)=N1 RKSHALMLSDTBQX-UHFFFAOYSA-N 0.000 description 1
- MUTDXQJNNJYAEG-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(dimethylamino)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)N(C)C MUTDXQJNNJYAEG-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- RSBKCGUHRMQUFJ-UHFFFAOYSA-N 2-chloro-4-(2-methoxyethoxy)-1,3,5-triazine Chemical class COCCOC1=NC=NC(Cl)=N1 RSBKCGUHRMQUFJ-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
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- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- DQKZTBYQBNVCJL-UHFFFAOYSA-N C(C(=C)C)(=O)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[P] Chemical compound C(C(=C)C)(=O)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[P] DQKZTBYQBNVCJL-UHFFFAOYSA-N 0.000 description 1
- DJRCMVCFUPOPKC-UHFFFAOYSA-N CCCCCCCCCCCC(=NO)C1=CC=C(C)C=C1O Chemical compound CCCCCCCCCCCC(=NO)C1=CC=C(C)C=C1O DJRCMVCFUPOPKC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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- 229940123457 Free radical scavenger Drugs 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L101/00—Compositions of unspecified macromolecular compounds
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- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
三嗪终止的含多个四甲基哌啶基的低聚物可作为聚合物添加剂使聚合物在暴露于光化辐射时具有抗降解性能。
Description
本发明涉及当暴露于光化辐射时具有抗降解和抗褪色性能的聚合物组合物。具体讲,它涉及用有效量的含2,2,6,6-四烷基哌啶部分的低聚三嗪基化合物稳定化的树脂如聚丙烯、聚乙烯等。本发明还涉及一组新的用作合成聚合物添加剂来延缓光降解作用的物质。
许多合成的有机聚合物当暴露于阳光时都发生迅速劣化。为了防止这种迅速降解,人们已用各种添加剂来稳定这些树脂以抗有害辐射。这些添加剂包括UV吸收剂如羟基二苯甲酮类和羟苯基苯并三唑类、可用来淬灭受激状态的有机镍配合物、以及最新的受阻胺光稳定剂(HALS)。HALS具有最通常取代在4-位的2,2,6,6-四烷基哌啶基,它作为自由基消除剂,由此抑制降解过程。对一种作为有效的光稳定剂的化合物有许多要求,它必须能与掺有它的树脂相容、具有足够的非挥发性以便在高温加工过程中或加工之后仍保留在树脂中、并且它能抵抗水提取作用。
尽管先有技术化合物通常是合成有机聚合物的有效的光稳定剂,但没有一种化合物能完全满足各种形式和用途的聚合物的稳定要求。对于用于薄型制品如纤维和薄膜的那些聚合物材料来说更是如此。由于这些缺陷,所以就需要一些能更全面地满足所述要求的物质。
本发明涉及把有效量的新的含多烷基哌啶部分的三嗪化合物掺入合成聚合物中来稳定该合成聚合物的方法。本发明的三嗪基HALS可选自式(Ⅰ)所述的化合物:
式中T为二价基:
式中A为:
R1选自氢和含1-5个碳原子的烷基如甲基、乙基、正丙基等,优选为氢和甲基,最优选为氢;
R2选自氢,氧,羟基,含1-18个碳原子的直链或支链的烷基如甲基、乙基、辛基、十八烷基或2-乙基己基,含2-18个碳原子的链烷酰基如乙酰基、丙酰基、丁酰基、异戊酰基或硬脂酰基,含3-4个碳原子的链烯基,含3-6个碳原子的链烯酰基,含3-6个碳原子的炔基如炔丙基或2-丁炔基,氰甲基,含7-15个碳原子的取代或未取代的苄基如3,5-二叔丁基-4-羟基苄基、3-叔丁基-4-羟基-5-甲基苄基,基团-CH2-CH(OR3)-R4;
R3选自氢,含1-18个碳原子的脂族基,如上述R2中的那些脂族基,芳脂基如苄基和苯乙基,以及含2-18个碳原子的脂酰基,如R2中的那些脂酰基;
R4选自氢,含1-16个碳原子的烷基,及苯基;
R5和R6可相同或不同,选自氢,含1-18个碳原子的烷基如甲基、乙基、异丙基,丁基、辛基、十二烷基及十八烷基,含5-12个碳原子的环烷基,含7-11个碳原子的芳烷基如苄基和丁基苄基,含3-12个碳原子的、可在链中连有一个-O-或-N(R9)-的烷基,含2-4个碳原子的羟基烷基,含3-15个碳原子的酰氧基烷基,式(A)中R1和R2为上述基团的基团,或R5和R6与它们所连接的N-原子一起形成杂环如吡咯烷子基、哌啶子基或形成的环可以有一个-O-链节形成吗啉代基;
R7选自含1-18个碳原子的烷基,含3-12个碳原子的链烯基,含5-12个碳原子的环烷基,含7-11个碳原子的芳烷基,含3-12个碳原子的、在链中具有-O-或-N(R9)-的烷基,或含6-14个碳原子的芳基如苯基、萘基、2,4-二甲基苯基;
R8和R9选自含1-4个碳原子的烷基如甲基、乙基、丙基等;
B为含1-10个碳原子的亚烷基;
Y选自-O-,-N(H)-及-N(R10)-,其中R10表示含1-20个碳原子的烷基或式(A)基团;
X选自氢,卤素,羟基,含1-18个碳原子的直链或支链烷基,含5-12个碳原子的环烷基,含6-18个碳原子的取代的或未取代的芳基,含7-18个碳原子的芳烷基,-N(R5)(R6),-OR7,-SR7或-P(O)(OR8);
R为含2-20个碳原子的直链或支链的亚烷基,其中亚烷基可被-O-、-S-或-N(R11)-间断,其中R11选自氢,含1-20个碳原子的烷基,含5-12个碳原子的环烯基,及选自下述基团的二价基;
含6-12个碳原子的亚芳基,或含8-14个碳原子的亚芳烷基;
R11为含1-18个碳原子的烷基,含5-12个碳原子的环烯基或基团A;
R12为基团X1,R13选自氢和三嗪基:
式中X如上面所限定,X1与X可相同或不同;
m为约1-40的整数,最好为2-10。
式(Ⅰ)化合物通常在溶剂如二恶烷、甲苯、二甲苯或任何其它适于反应发生的溶剂存在下,由式(Ⅱ)的取代三嗪(参见结构式表,其中卤素指Br,Cl或Ⅰ)与式(Ⅲ)的二胺反应制备。通常Ⅲ与Ⅱ的化学计量比为约1∶1。该反应可在约25-200℃之间进行,但通常更方便地是在所用溶剂的回流温度下进行。该反应也可在碱如氢氧化物、碳酸盐、或胺如三乙胺等存在下进行,碱的作用是清除所生成的HCl、使反应能进行完全。虽然对于该反应的进行来说,使用碱不是必需的,但由于中间体卤化氢加成盐可从溶液中沉淀出来,所以使用碱确实能加快达到反应完全的速度、最初低聚后连在三嗪环上的剩余的卤素可由粗产物与所需的亲核试剂如胺或醇反应除去。
式(Ⅱ)所示的一类2-取代-4,6-二卤代-1,3,5-三嗪制备方法在文献中和先有技术中是众所周知的。这些化合物通常可在低温如0-5℃下、在惰性溶剂如二噁烷或丙酮存在下、由适当的胺、醇、硫醇、磷酸盐或其它亲核试剂进行有规加成得到。在胺加成情况下,可用清除碱与反应中形成的卤化氢反应。所述清除碱可是上述清除碱中的任何一种。该反应产物一般可通过过滤并干燥方法分离。
式(Ⅱ)化合物的说明性实例包括下述化合物,但不限于下述化合物:
2,4-二氯-6-叔丁基氨基-1,3,5-三嗪,
2,4-二氯-6-叔辛基氨基-1,3,5-三嗪,
2,4-二氯-6-吗啉代-1,3,5-三嗪,
2,4-二氯-6-甲氧基-1,3,5-三嗪,
2,4-二氯-6-苄基氨基-1,3,5-三嗪,
2,4-二氯-6-(2-羟基乙基氨基)-1,3,5-三嗪,
2,4-二溴-6-环己基氨基-1,3,5-三嗪,
2,4-二溴-6-二异丙基氨基-1,3,5-三嗪,
2,4-二氯-6-(2-甲氧基乙氧基)-1,3,5-三嗪,
2,4-二氯-6-(二(2,2,6,6-四甲基-4-哌啶基氨基))-1,3,5-三嗪,
2,4-二氯-6-乙氧羰基亚甲基氨基-1,3,5-三嗪,
2,4-二氯-6-(2-丙烯基氧基)-1,3,5-三嗪,
2,4-二溴-6-环己基氧基-1,3,5-三嗪,
2,4-二氯-6-甲硫基-1,3,5-三嗪,
2,4-二氯-6-十二烷硫基-1,3,5-三嗪,
2,4-二氯-6-(2-乙酰氧基乙基氨基)-1,3,5-三嗪,
2,4-二氯-6-二甲基膦酰基-1,3,5-三嗪等。
式(Ⅲ)化合物可由式(Ⅳ)化合物与化合物H-Y-R-Y-H(其中B、Y和R如上限定,R14为低级烷基如甲基或乙基)反应制备。该反应可在100-200℃温度范围内在无溶剂存在下用碱性催化剂如氨化锂、异丙氧基钛(Ⅳ)等来进行,并随后除去反应产生的醇。该反应也可以在惰性溶剂如二甲苯、甲苯等中、在或低于溶剂的回流温度下进行。一些式(Ⅳ)化合物已描述在先有技术中:如GB2,136,805(1983),DE3,512,634(1986),美国专利4,578,472及美国专利4,670,488。
通常,这些化合物的合成方法包括用所需卤代酸(或盐)或卤化酯对式(Ⅴ)化合物进行迈克尔加成反应。可用来制备这些化合物的其它方法包括化合物(Ⅴ)与所需要的醛如OHC(B)CO R15(其中R15为氢或低级烷基)的还原胺化反应或涉及式(Ⅵ)化合物与所需要的式(Ⅶ)氨基酸或氨基酸酯的反向还原胺化反应。
式(Ⅲ)化合物的说明性实例包括(但不限于)下述化合物:
2,2,6,6-四甲基-4-哌啶基氨基乙酸与乙二醇形成的二酯(m.p.75-80℃),
2,2,6,6-四甲基-4-哌啶基氨基乙酸与1,4-丁二醇形成的二酯,
3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸与1,6-己二醇形成的二酯,
1,2,2,6,6-五甲基-4-哌啶基氨基乙酸与1,6-己二醇形成的二酯,
2,2,6,6-四甲基-4-哌啶基氨基乙酸与1,6-己二醇形成的二酯(m.p.90-92℃),
1,2,2,6,6-五甲基-4-哌啶基氨基乙酸与2,2-二甲基-1,3-丙二醇形成的二酯,
2,2,6,6-四甲基-4-哌啶基氨基乙酸与2,2-二甲基-1,3-丙二醇形成的二酯(m.p.85-88℃),
2,2,6,6-四甲基-4-哌啶基氨基乙酸与1,2-乙二胺形成的二酰胺(m.p.153-158℃),
2,2,6,6-四甲基-4-哌啶基氨基乙酸与1,6-二(2,2,6,6-四甲基-4-哌啶基氨基)己烷形成的二酰胺,
2,2,6,6-四甲基-4-哌啶基氨基乙酸与2,2′-二羟基乙醚形成的二酯,
2-甲基-3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸与乙二醇形成的二酯,
4-(2,2,6,6-四甲基-4-哌啶基氨基)丁酸与2,2-二甲基-1,3-丙二醇形成的二酯,
2,2,6,6-四甲基-4-哌啶基氨基乙酸与N,N-二(2-羟基乙基)-4-氨基-2,2,6,6-四甲基哌啶形成的二酯,
2,2,6,6-四甲基-4-哌啶基氨基乙酸与1,4-环己二甲醇形成的二酯,
3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸与1,6-己二胺形成的二酰胺,
3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸与2,2-二甲基-1,3-丙二醇形成的二酯(m.p.128-130℃),
11-(2,2,6,6-四甲基-4-哌啶基氨基)十一烷酸与乙二醇形成的二酯,
6-(2,2,6,6-四甲基-4-哌啶基氨基)己酸与2,2-二甲基-1,3-丙二醇形成的二酯等等。
从美国专利3,684,765已知,用以转变成本发明化合物的中间体4-氨基多烷基哌啶是已知化合物,并且它们通常可用氨或有关的胺对相应的酮进行还原胺化制备。
式(Ⅵ)4-氧代哌啶可由氨与脂族酮反应制备。氨与丙酮生成三丙酮胺的反应是众所周知的,文献中给出了它的多种制备方法。氨与甲乙酮的反应已由W.Traube描述在Chem.Ber.41,777(1908)中。
在2-位和6-位带有其它烷基取代基的式(Ⅵ)化合物可分两步按Helv.Chem.Acta 30,1114(1947)和Monatsh.Chem.88,464(1957)中概述的方法反应,然后水解所得嘧啶来制备。
在本发明的实例中,当R2不是氢时,可很容易地对式(Ⅵ)化合物进行另外的衍生反应。通常,引入R2的反应可容易地通过适当的转化反应如对母体N-H化合物进行烷基化或氧化,然后通过还原胺化引入4-氨基取代基完成。
还原胺化反应可以按先有技术和主要文献中已很好地描述过的方法进行。通常可以使用催化氢化反应中常用的任何催化剂。较好的催化剂有Pd/C和Pt/C。该反应通常在溶剂存在下进行。合适的溶剂有甲醇和乙醇及其它溶剂。氢化反应通常在1-10个大气压的氢压下和完成还原所必需的温度下进行。通常还原可在环境温度下进行,但有时得使用高达约100℃的温度。
引入烷基、链烯基、炔基及芳烷基的反应可通过最初制备的含游离的哌啶N-H的式(Ⅵ)酮或式(Ⅰ)衍生的三嗪与合适的卤化物反应完成。合适的卤化物实例包括碘甲烷、氯甲烷、溴乙烷、十二烷基氯、十八烷基氯、烯丙基溴、甲基烯丙基氯、丁烯基氯、炔丙基氯、苄基氯、苯乙基溴及表氯醇。生成的卤化氢可通过于反应混合物中加入无机碱如碳酸盐或氢氧化物或加入有机胺如三乙胺来除去。
引入链烷酰基或链烯酰基的反应可通过用合适的酰卤或方便时用酸酐对N-H基进行酰化来完成。如果使用酰卤,产生的卤化氢可通过上述同样方法除去。合适的酰化试剂有乙酰氯、乙酐、丙酐、己酰氯、十二烷酰氯及十八烷酰氯。
引入基团-CH2CH(O-R3)-R4时,取代基可由母体N-H化合物与相应的氧化烯如氧化乙烯、氧化丙烯和氧化苯乙烯的反应来引入。所得羟基化合物可按通常先有技术中已知的方法用合适的酰卤酰化,并且可通过形成烷氧化物并与所需烷基卤反应进行烷基化。
当R2为氧或羟基时,可将母体N-H化合物在催化剂如钨酸钠存在下用氧化剂如过氧化氢处理,或用过氧羧酸如间氯过氧苯甲酸处理,若所需的是羟基,则接着用催化氢化法来还原氧基。
本发明化合物是合成有机聚合物的有效光稳定剂。提供下述实例是用来说明本发明,而不是对本发明范围的限制:
2,4-二氯-6-叔丁基氨基-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和2,2-二甲基-1,3-丙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-叔辛基氨基-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和2,2-二甲基-1,3-丙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-吗啉代-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和2,2-二甲基-1,3-丙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-叔辛基氨基-1,3,5-三嗪与3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸和2,2-二甲基-1,3-丙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-吗啉代-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和1,6-己二醇所形成的二酯形成的低聚物;
2,4-二氯-6-吗啉代-1,3,5-三嗪与3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸和乙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-叔丁基氨基-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和乙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-甲氧基-1,3,5-三嗪与3-(1,2,2,6,6-五甲基-4-哌啶基氨基)丙酸和2,2-二甲基-1,3-丙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-(烯丙基)氨基-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和乙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-吗啉代-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和1,2-二氨基乙烷所形成的二酰胺形成的低聚物;
2,4-二氯-6-十二烷硫基-1,3,5-三嗪与1,2,2,6,6-五甲基-4-哌啶基氨基乙酸和1,6-己二胺所形成的二酰胺形成的低聚物;
2,4-二氯-6-吗啉代-1,3,5-三嗪与4-(2,2,6,6-四甲基-4-哌啶基氨基)乙酸和1,6-己二醇所形成的二酯形成的低聚物;
2,4-二氯-6-(2,2,6,6-四甲基-4-哌啶基氨基)-1,3,5-三嗪与5-(2,2,6,6-四甲基-4-哌啶基氨基)戊酸和乙二醇所形成的二酯形成的低聚物;
2,4-二氯-6-叔辛基氨基-1,3,5-三嗪与2,2,6,6-四甲基-4-哌啶基氨基乙酸和1,6-己二醇所形成的二酯形成的低聚物等等。
本发明的化合物是合成有机聚合物的有效的光稳定剂,除了它们的有效的光稳定性质外,一些本发明化合物也表现出优良的热稳定性能。可用本发明化合物稳定化的合成有机聚合物中包括聚烯烃类,它包括烯烃均聚物如聚乙烯、高和低密度聚乙烯、聚丙烯、聚丁二烯、聚苯乙烯等;和烯烃与其它乙烯型不饱和单体的共聚物如乙烯-丙烯共聚物、乙烯-丁烯共聚物、乙烯-醋酸乙烯共聚物、苯乙烯-丁二烯共聚物等;三元共聚物如丙烯腈-丁二烯-苯乙烯共聚物等;聚氯乙烯,聚偏二氯乙烯,氯乙烯和偏二氯乙烯与醋酸乙烯或其它乙烯型不饱和单体的共聚物;聚缩醛如聚甲醛和聚氧化乙烯;聚酯如聚对苯二甲酸乙二醇酯;聚酰胺如聚酰胺6,聚酰胺6,6,聚酰胺6,10;聚氨酯和由不饱和酸及其衍生物得到的聚合物;聚碳酸酯;聚丙烯酸酯和聚甲基丙烯酸酯,聚丙烯酰胺和聚丙烯腈,以及丙烯酸和其一种或几种衍生物与三聚氰胺-甲醛树脂形成的共聚物。
在上述各组聚合物中,特别重要的是对聚烯烃的稳定作用。本发明化合物可很好地用于该聚烯烃的稳定化,通常,按所要稳定的聚合物重量的0.01-5.0%(重量)的量把本发明的稳定剂加到要稳定的聚合物中。优选地,稳定剂用量为0.05-1%(重量)。
本发明化合物还可与其它稳定剂结合来制备稳定的树脂组合物。所述其它添加剂可以是抗氧化剂,辐助光稳定剂如受阻胺、金属减活剂等,颜料,着色剂,填料,阻燃剂,抗静电剂等。
合适的抗氧剂包括受阻酚型抗氧剂如2,6-二叔丁基对甲酚;4,4′-双(2,6-二异丙基苯酚);2,4,6-三叔丁基苯酚;2,2′-硫双(4-甲基-6-叔丁基酚);2-(3′,5′-二叔丁基-4′-羟基苯基)丙酸十八烷基酯;四(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)异氰脲酸酯;1,3,5-三(3,5′-二叔丁基-4′-羟基苯基)丙酸酯)异氰脲酸酯;1,3,5-三(3,5′-二叔丁基-4′-羟基苄基)-2,4,6-二甲基苄基)-均三嗪-2,4,6-(1H,3H,5H)-三酮;硫二丙酸酯如硫二丙酸二月桂酯和硫二丙酸二硬脂基酯等;亚磷酸酯如亚磷三苯酯、亚磷酸三壬酯、二亚磷酸二(十二烷醇)季戊四醇酯、亚磷酸二苯基癸基酯、亚磷酸三(2,4-二叔丁基苯基)酯、二亚磷酸二(2,4-二叔丁基苯酚)季戊四醇酯等;辐助光稳定剂包括,例如,苯并三唑类,包括2-(2′-羟基-5′-叔辛基苯基)苯并三唑;2-(2′-羟基-3′,5′-二叔丁基)-5-氯苯并三唑;2-(2′-羟基-5′-甲基苯基)苯并三唑;2-(2′-羟基-3′-叔丁基-5′-甲基苯基)苯并三唑;2-(2′-羟基-3′,5′-二叔戊基苯基)苯并三唑;羟基二苯甲酮类如2-羟基-4-甲氧基二苯甲酮;2-羟基-4-辛氧基二苯甲酮;受阻酚类如3,5-二叔丁基-4-羟基苯甲酸正十六烷基酯和3,5-二叔丁基-4-羟基苯甲酸2′,4′-二叔丁基苯基酯;金属配合物如2,2′-硫二(4,6-辛基苯酚)镍配合物;二丁基氨荒酸镍;4-羟基-3,5-二叔丁基苄基膦酸单烷基酯镍盐,其中烷基为甲基、乙基等;以及2-羟基-4-甲基苯基十一烷基酮肟的镍配合物。
其它的合适的辅助光稳定剂的实例可参见美国专利3,488,290和3,496,134。
下述实例用来说明本发明,而不以任何方式限制本发明的性质或范围。每一实例的NMR分析表明,所得光谱与所期望的低聚混合物的一致。各实例的FAB-MS分析表明n值为1-8。
实例1
将2,4-二氯-6-吗啉代-1,3,5-三嗪(1.52g,6.48mmol)和2,2,6,6-四甲基-4-哌啶基氨基乙酸与乙二醇所形成的二酯(2.95g,6.48mmol)的混合物在二噁烷(25ml)中加热回流约18小时。反应完毕,除去二恶烷,将残留物溶于二氯甲烷,依次用稀氢氧化钠和水洗涤。然后将该溶液干燥并浓缩,得到浅黄色粘稠残留物。处理后得到米色固体(m.p.110-114℃),重约4.0g。
实例2
按基本与实例1的合成方法相同的方法制备由2,4-二氯-6-叔辛基氨基-1,3,5-三嗪(1.97g)和2,2,6,6-四甲基-4-哌啶基氨基乙酸与新戊二醇所形成的二酯(3.55g)衍生的低聚混合物。后处理后,得到米色泡沫固体状产物(4.37g),m.p.47-54℃。
实例3
于按类似于上述方法制备的实例2产物的样品(5.0g)中加入30ml甲苯和约2g叔辛胺。将混合物回流18小时,然后冷却并加水和盐水进行分配,反洗后干燥(Na SO)并浓缩,得到黄色残留物。真空处理后,得到可发出嘎吱嘎吱声的泡沫(3.8g),m.p.59-62℃。
实例4
按与实例1相同的方法制备由2,4-二氯-6-叔丁基氨基-1,3,5-三嗪(1.71g)和2,2,6,6-四甲基-4-哌啶基氨基乙酸与新戊二醇所形成的二酯(3.85g)衍生的低聚混合物。后处理后和分离,得到2.97g米色泡沫状产物,瘪泡温度50-55℃。
实例5
按与实例4相同的方法用2,6-二氯-6-吗啉代-1,3,5-三嗪代替2,4-二氯-6-叔丁基氨基-1,3,5-三嗪,制备低聚混合物。反应物用量为:1.78g上述三嗪和3.77g二酯。回流6小时后进行后处理,分离产物,得米色泡沫状物质3.42g,瘪泡温度50-
实例6
按与实例1相同的方法制备由2,4-二氯-6-吗啉代-1,3,5-三嗪(1.53g)和2,2,6,6-四甲基-4-哌啶基氨基乙酸与乙二胺所形成的二酰胺(2.94g)衍生的低聚混合物。回流约18小时后,在CH2Cl2和水之间进行分配,将有机溶液干燥并浓缩,得到3.93g米色泡沫,瘪泡温度55-60℃。
实例7
按相似于实例6的方法制备由2,4-二氯-6-叔丁基氨基-1,3,5-三嗪(1.10g)和2,2,6,6-四甲基-4-哌啶基氨基乙酸与乙二胺所形成的二酰胺(2.26g)衍生的低聚混合物。在该实例中,反应中使用了粉状K2CO3(1.38g),而不是在后处理时进行氢氧化钠洗。和实例6一样,后处理所得产物为米色泡沫(2.84g),瘪泡温度55-60℃。
实例8
按实例7的方法制备由2,4-二氯-6-吗啉代-1,3,5-三嗪(1.40g)和2,2,6,6-四甲基-4-哌啶基氨基乙酸与1,6-己二胺所形成的二酰胺(3.08g)衍生的低聚混合物。该实例中也使用了K2CO3(1.64g)。反应完毕,如实例7进行后处理,得到4.16g产物,软化点90-93℃。
实例9
将2,4-二氯-6-叔辛基氨基-1,3,5-三嗪(1.9g,6.85mmol)和3-(2,2,6,6-四甲基-4-哌啶基氨基)丙酸与2,2-二甲基-1,3-丙二醇所形成的二酯(3.6g,6.85mmol)的混合物在二噁烷(25ml)中加热回流约18小时。反应完毕,除去二噁烷。残留物溶于二氯甲烷中,先后用稀氢氧化钠水溶液和水洗涤。将该溶剂干燥并浓缩,得黄色粘稠残留物。
实例10-14
为了进一步说明上述化合物作为光稳定剂的效果,把实例2-5所述的低聚物分别掺到市售的由Hercules Corporation生产的商品Pro-Fax 6301 Polypropylene Resin中。用混有二氯甲烷的溶剂把光稳定剂按总树脂组合物重量的0.25%的量掺到聚丙烯中。加入主要抗氧剂(β-3.5-二叔丁基-4-羟基苯基丙酸硬脂基酯(用量为0.2%)。然后将树脂在200℃挤塑并在6,000psi和188℃压塑,得到厚度为5密耳的薄膜。按同样的步骤生产不含该光稳定剂的对照薄膜。将每种薄膜在阿特拉斯天候老化仪中暴露于氙弧光中,直到IR羰基增加0.5,此时被认为是破损点。
表1
实例号 稳定剂 破损时间(hrs)
10 对照 400
11 化合物2 3050
12 化合物3 2300
13 化合物4 3625
14 化合物5 3290
Claims (17)
1、式I所示的化合物,
式中T为二价基:
R1选自氢和含1-5个碳原子的烷基;
R2选自氢,氧,羟基,含1-18个碳原子的直链或支链烷基,含2-18个碳原子的链烷酰基,含3-4个碳原子的链烯基,含3-6个碳原子的链烯酰基,含3-6个碳原子的炔基,氰甲基,含7-15个碳原子的苄基和基团-(CH2-CH(OR3)-R4;
R3选自氢,含1-18个碳原子的脂族基,芳脂基及脂酰基;
R4选自氢,含1-16个碳原子的烷基及苯基;
X选自氢,卤素,羟基,含1-18个碳原子的烷基,含5-12个碳原子的环烷基,含6-18个碳原子的取代的或未取代的芳基,含7-18个碳原子的芳烷基,-N(R5)(R6),-OR7,-SR7或-PO(OR8)2;
R5和R6可相同或不同,选自氢,含1-18个碳原子的烷基,含5-12个碳原子的环烷基,含7-11个碳原子的芳烷基,含3-12个碳原子的、可在链中含有一个-O-或-N(R9)-的烷基,含2-4个碳原子的羟基烷基,含3-15个碳原子的酰氧烷基,式(A)基团,或R5和R6与它们所连的N-原子一起形成杂环如吡咯烷子基、哌啶子基或形成的环可具有一个-O-环节形成吗啉代基;
R7选自含1-18个碳原子的烷基,含3-12个碳原子的链烯基,含5-12个碳原子的环烷基,含7-11个碳原子的芳烷基,或含3-12个碳原子的、在链中具有-O-或-N(R9)-的烷基,或含6-14个碳原子的芳基;
R3和R9选自含1-4个碳原子的烷基;
B为含1-11个碳原子的亚烷基;
Y选自-O-,-N(H)-,及-N(R10)-,其中R10表示含1-20个碳原子的烷基或基团(A);
R选自含2-20个碳原子的直链或支链的亚烷基,其中亚烷基可间有-O-、-S-或-N(R11),其中R11选自氢,含1-20个碳原子的烷基,基团(A),含5-12个碳原子的环烯基,选自下列各式的二价基:
含6-12个碳原子的亚芳基,或含8-14个碳原子的亚芳烷基;
R11为含1-18个碳原子的烷基,含5-12个碳原子的环烯基或基团(A);
R12为基团X1,R13选自氢和三嗪基
式中X如上所限定,X1与X可相同或不同,以及
m为1-40的整数。
2、根据权利要求1的化合物,其中R1为氢。
3、根据权利要求2的化合物,其中B为亚甲基。
4、根据权利要求3的化合物,其中Y为-O-或-NH-。
5、根据权利要求4的化合物,其中m为1-10。
6、根据权利要求2的化合物,其中B选自亚甲基和亚乙基,R2为氢。
7、根据权利要求6的化合物,其中X为叔丁基氨基,Y为-O-,及R为2,2-二甲基-1,3-亚丙基。
8、根据权利要求6的化合物,其中X为叔辛基氨基,Y为-O-,B为亚甲基,及R为2,2-二甲基-1,3-亚丙基。
9、根据权利要求6的化合物,其中X为吗啉代基,Y为-O-,B为亚甲基,及R为2,2-二甲基-1,3-亚甲基。
10、根据权利要求6的化合物,其中X为吗啉代基,Y为-NH-,及R为1,6-亚己基。
11、根据权利要求6的化合物,其中X为吗啉代基,Y为-O-,及R为1,2-亚乙基。
12、根据权利要求6的化合物,其中X为叔辛基氨基,Y为-NH-,及R为1,2-亚乙基。
13、根据权利要求6的化合物,其中X为叔丁基氨基,B为亚乙基,Y为-O-,及R为2,2-二甲基-1,3-亚丙基。
14、根据权利要求6的化合物,其中X为吗啉代基,B为亚甲基,Y为-NH-,及R为1,2-亚乙基。
15、一种对光诱导的降解稳定的合成聚合物组合物,它包含一种通常受光照易劣化的有机聚合物和0.01-5%重量的权利要求1中通式所示的化合物。
16、根据权利要求15的组合物,其中有机聚合物为聚烯烃均聚物或共聚物。
17、根据权利要求16的组合物,其中所述的有机聚合物为丙烯均聚物或共聚物。
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US07/284,583 US4889882A (en) | 1988-12-15 | 1988-12-15 | Tetramethyl piperidyl terminated triazine oligomeric esters and amides |
US284,583 | 1988-12-15 |
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CN89108964A Pending CN1045102A (zh) | 1988-12-15 | 1989-12-15 | 四甲基哌啶基终止的三嗪低聚酯和酰胺 |
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US (1) | US4889882A (zh) |
EP (1) | EP0373892A1 (zh) |
JP (1) | JP2863576B2 (zh) |
KR (1) | KR0139910B1 (zh) |
CN (1) | CN1045102A (zh) |
AU (1) | AU616080B2 (zh) |
BR (1) | BR8906519A (zh) |
CA (1) | CA2005235C (zh) |
DK (1) | DK636589A (zh) |
FI (1) | FI895989A0 (zh) |
GB (1) | GB8928102D0 (zh) |
NO (1) | NO894670L (zh) |
ZA (1) | ZA898929B (zh) |
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DE4108029A1 (de) * | 1991-03-13 | 1992-09-17 | Bayer Ag | Triazinyl-substituierte acrylsaeureester |
US5211302A (en) * | 1992-07-16 | 1993-05-18 | Paolo Tiramani | Cosmetic organizer |
IT1263892B (it) * | 1993-02-11 | 1996-09-05 | Graziano Vignali | Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici |
US6046304A (en) * | 1995-12-04 | 2000-04-04 | Ciba Specialty Chemicals Corporation | Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials |
US7582690B2 (en) * | 2004-11-19 | 2009-09-01 | Eastman Chemical Company | Stabilized aliphatic polyester compositions |
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US31261A (en) * | 1861-01-29 | Window stop and fastener | ||
US3485764A (en) | 1964-05-22 | 1969-12-23 | American Cyanamid Co | Polymeric photochromic compositions stabilized with ultraviolet light absorbers |
US3496134A (en) | 1967-06-20 | 1970-02-17 | American Cyanamid Co | Stabilization of rigid poly(vinylchloride) plastics with bis-amides and ultraviolet absorbers |
US3684765A (en) | 1970-01-08 | 1972-08-15 | Sankyo Co | Stabilization of synthetic polymers |
USRE31261E (en) | 1976-07-28 | 1983-05-31 | Adeka Argus Chemical Co., Ltd. | 2,2,6,6-Tetrasubstituted-4-piperidyl carboxy heterocyclic compounds as stabilizers for synthetic polymers |
DE2933078A1 (de) * | 1979-08-16 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | Neue triazinderivate, ihre herstellung und ihre verwendung als stabilisatoren fuer synthetische polymere |
US4331586A (en) * | 1981-07-20 | 1982-05-25 | American Cyanamid Company | Novel light stabilizers for polymers |
US4348493A (en) * | 1981-07-20 | 1982-09-07 | American Cyanamid Company | Novel light stabilizers for polymers |
IT1198355B (it) * | 1982-02-10 | 1988-12-21 | Apital Prod Ind | Derivati piperidinici e loro uso come stabilizzanti per polimeri |
DE3408948C2 (de) | 1983-03-21 | 1995-07-27 | Sandoz Ag | 4-Amino-polyalkylpiperidinverbindungen |
CA1266272A (en) | 1983-05-27 | 1990-02-27 | Masakatsu Yoshimura | A 2,2,6,6-tetramethylpiperidine derivative, its production and a stabilizer for synthetic resins containing the same |
JPS61155368A (ja) | 1984-12-28 | 1986-07-15 | Sumitomo Chem Co Ltd | ピペリジン誘導体、その製造方法およびこれを有効成分とする有機物質用安定剤 |
DE3512634A1 (de) | 1985-04-06 | 1986-10-16 | Sandoz-Patent-GmbH, 7850 Lörrach | Neue 4-amino-polyalkylpiperidinverbindungen |
DE3852742T3 (de) * | 1987-09-21 | 2005-02-10 | Ciba Speciality Chemicals Holding Inc. | N-substituierte sterisch gehinderte Amin-Stabilisatoren. |
ES2060124T3 (es) * | 1989-06-06 | 1994-11-16 | Ciba Geigy Ag | Nuevas sulfonilureas. |
-
1988
- 1988-12-15 US US07/284,583 patent/US4889882A/en not_active Expired - Fee Related
-
1989
- 1989-11-22 ZA ZA898929A patent/ZA898929B/xx unknown
- 1989-11-23 NO NO89894670A patent/NO894670L/no unknown
- 1989-11-28 AU AU45628/89A patent/AU616080B2/en not_active Ceased
- 1989-12-12 CA CA002005235A patent/CA2005235C/en not_active Expired - Fee Related
- 1989-12-12 GB GB898928102A patent/GB8928102D0/en active Pending
- 1989-12-12 EP EP89312987A patent/EP0373892A1/en not_active Withdrawn
- 1989-12-14 FI FI895989A patent/FI895989A0/fi not_active Application Discontinuation
- 1989-12-14 KR KR1019890018584A patent/KR0139910B1/ko not_active IP Right Cessation
- 1989-12-14 JP JP1324855A patent/JP2863576B2/ja not_active Expired - Lifetime
- 1989-12-15 DK DK636589A patent/DK636589A/da not_active Application Discontinuation
- 1989-12-15 CN CN89108964A patent/CN1045102A/zh active Pending
- 1989-12-15 BR BR898906519A patent/BR8906519A/pt not_active IP Right Cessation
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Publication number | Publication date |
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JP2863576B2 (ja) | 1999-03-03 |
EP0373892A1 (en) | 1990-06-20 |
NO894670L (no) | 1990-06-18 |
JPH02218678A (ja) | 1990-08-31 |
DK636589A (da) | 1990-06-16 |
ZA898929B (en) | 1990-11-28 |
CA2005235C (en) | 1999-09-21 |
FI895989A0 (fi) | 1989-12-14 |
DK636589D0 (da) | 1989-12-15 |
AU4562889A (en) | 1990-06-21 |
KR0139910B1 (ko) | 1998-12-01 |
BR8906519A (pt) | 1990-08-21 |
AU616080B2 (en) | 1991-10-17 |
GB8928102D0 (en) | 1990-02-14 |
CA2005235A1 (en) | 1990-06-15 |
US4889882A (en) | 1989-12-26 |
NO894670D0 (no) | 1989-11-23 |
KR900009771A (ko) | 1990-07-05 |
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