CN1036760A - 四甲基哌啶子基-s-三嗪类化合物 - Google Patents
四甲基哌啶子基-s-三嗪类化合物 Download PDFInfo
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- CN1036760A CN1036760A CN89101832A CN89101832A CN1036760A CN 1036760 A CN1036760 A CN 1036760A CN 89101832 A CN89101832 A CN 89101832A CN 89101832 A CN89101832 A CN 89101832A CN 1036760 A CN1036760 A CN 1036760A
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- alkyl
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 title description 20
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 title description 4
- 150000003918 triazines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 146
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 239000011368 organic material Substances 0.000 claims abstract description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
- -1 4Be hydrogen Chemical class 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000006839 xylylene group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000004306 triazinyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical class CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004050 enoyl group Chemical group 0.000 claims description 2
- 125000005628 tolylene group Chemical group 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 229920000620 organic polymer Polymers 0.000 claims 1
- 239000001301 oxygen Substances 0.000 abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 105
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 83
- 239000002585 base Substances 0.000 description 74
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- 239000000047 product Substances 0.000 description 58
- 239000000203 mixture Substances 0.000 description 53
- 239000000243 solution Substances 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 23
- 238000001953 recrystallisation Methods 0.000 description 23
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 22
- 230000008020 evaporation Effects 0.000 description 22
- 238000000034 method Methods 0.000 description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 17
- 238000002425 crystallisation Methods 0.000 description 17
- 230000008025 crystallization Effects 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 16
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229920002554 vinyl polymer Polymers 0.000 description 10
- 229910004298 SiO 2 Inorganic materials 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229960003742 phenol Drugs 0.000 description 9
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 150000000182 1,3,5-triazines Chemical class 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002943 EPDM rubber Polymers 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229940014772 dimethyl sebacate Drugs 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 210000002741 palatine tonsil Anatomy 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 150000003053 piperidines Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CCKCWUJSVQMZNX-UHFFFAOYSA-N 2-chloro-4-propan-2-yloxy-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine Chemical class CC(C)OC1=NC(Cl)=NC(N2C(CCCC2(C)C)(C)C)=N1 CCKCWUJSVQMZNX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 229940017219 methyl propionate Drugs 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- XDNYQCMETGDICR-UHFFFAOYSA-N 1-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)-2,2,6,6-tetramethylpiperidin-4-one Chemical class CC1(C)CC(=O)CC(C)(C)N1C1=NC(N2CCOCC2)=NC(N2CCOCC2)=N1 XDNYQCMETGDICR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 238000000605 extraction Methods 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000003381 stabilizer 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical group O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- KABSHHVPLKAOQN-UHFFFAOYSA-N 1-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical class CC1(C)CC(O)CC(C)(C)N1C1=NC(N2CCOCC2)=NC(N2CCOCC2)=N1 KABSHHVPLKAOQN-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- RPRRJFJXNUQLGT-UHFFFAOYSA-N n,n-dibutyl-4-propan-2-yloxy-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazin-2-amine Chemical class CCCCN(CCCC)C1=NC(OC(C)C)=NC(N2C(CCCC2(C)C)(C)C)=N1 RPRRJFJXNUQLGT-UHFFFAOYSA-N 0.000 description 1
- PREAKWXFNPWNEG-UHFFFAOYSA-N n-butyl-n-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide Chemical class CCCCN(C(C)=O)C1CC(C)(C)NC(C)(C)C1 PREAKWXFNPWNEG-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- UZUCIYYGGBSFAB-UHFFFAOYSA-N n-hexyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCCCNC1CC(C)(C)NC(C)(C)C1 UZUCIYYGGBSFAB-UHFFFAOYSA-N 0.000 description 1
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- 125000005574 norbornylene group Chemical group 0.000 description 1
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- 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 1
- 239000012044 organic layer Substances 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
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- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
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- 150000003921 pyrrolotriazines Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
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- 229910052895 riebeckite Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 150000003335 secondary amines Chemical class 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
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- 239000003351 stiffener Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical class CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
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- 239000001043 yellow dye Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
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- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- C08K5/00—Use of organic ingredients
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- 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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- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
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- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/3924—Heterocyclic
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Abstract
含有至少一个式I基团的化合物,
Description
本发明涉及含有至少一个四甲基哌啶子基的新的三嗪衍生物,它们用作有机物的稳定剂。
在其分子中含有至少一个三嗪基和一个2,2,6,6-四甲基-4-哌啶基的化合物,就是通常所说的有机物的稳定剂。这样的化合物或者仅含有-个三嗪基,例如在US-A-3,925,376中所叙述的化合物,或者含有若干个三嗪基,例如在US-A-4,108,826中所叙述的化合物。他们也可是低聚物或具有重复的三嗪基的聚合物,例如在US-A-4,086,204中所叙述的化合物。在所有这些化合物中,哌啶基通过4-位与三嗪环相连。
现在已发现的化合物中,2,2,6,6-四甲基哌啶基通过1-位(氮原子)连接到三嗪环上。两种这样的化合物在DE-A-2,025,080中描述,并在该文中推荐作为药物,而没有提到用作稳定剂。
本发明涉及含有至少一个式I基团的化合物,其中X是完成其环使之形成哌啶环的基,而2-(2,2,6,6-四甲基-1-哌啶子基)-4,6-双(2,4,4-三甲基-2-戊基氨基)三嗪和2,4-二氯-6-(2,2,6,6-四甲基-1-哌啶子基)-三嗪除外。
优选的化合物含有至少一个式1基团,其中X不是CH2。
这样的基团可存在于大部分不同种类的化合物中。本发明最重要的化合物种类如下:
1)式II化合物其中:n是1至6的整数,R1是下式基或是Cl、OH、-OR3、-SR3或-NR4R5,其中R3是C1-C18烷基、烯丙基、环己基、苄基、苯基或式A基R4是氢、C1-C12烷基、2-羟乙基、烯丙基、环己基、苄基或式A基,R5是C1-C12烷基、2-羟乙基、烯丙基、环己基、苄基、苯基、被卤素、C1-C4烷基或C1-C4烷氧基取代的苯基、式A基或式C基其中:D是由 断开的C2-C20亚烷基,Ra和Rb是C1-C12烷基、C5-C6环烷基、C6-C10芳基或C7-C9苯烷基,而Ra也可是氢,或R4和R5在一起是由-O-或-N(R8)-断开的C4-C8亚烷基,其中R8是氢、C1-C4烷基或乙酰基,R6是氢、C1-C12烷基、C7-C9苯烷基、C3-C5链烯基、C2-C4烷酰基、C3-C5烯酰基、-O、-OH或-OR7,且R7是C1-C18烷基、C5-C8环烷基、C7-C9苯烷基、苯2-C18烷酰基或苯甲酰基,R2,如果n=1,是Cl、OH、-OR3、-SR3或-NR4R5,如果n=2,R2是-O-R9-O-、-S-R9-S-、-N(R10)-R9-N(R10)-、-O-R9-N(R10)-、 或-NH-NH-,其中R9是可被一个或多个-O-、-N(R8)-或-OOC-R17-COO-断开的C2-C20亚烷基、C4-C8亚烷基、C5-C8亚环烷基、亚二甲苯基、亚苯基或亚甲代苯基,R10是氢、C1-C12烯丙基2-羟基乙基、苄基、苯基或式A基,如果n=3,R2是或 其中a是2或3,Q是-O-、-S-或-N(R10)-,和T是C3-C20烷烃三基或或 其中AIK是C2-C12亚烷基,如果n=4,R2是C(CH2O-)4或 其中a是2或3和b是2-12,如果n=5,R2是如果n=6,R2是 y是下面的基: 或 其中:m是0、1或2,q是5-11的整数,R11是氢、C1-烷基、C3-C7链烯基、C5-C8环烷基、C7-C11芳烷基或-CO-R18,R12是氢、C1-C12烷基、C3-C6链烯基、C5-C8环烷基、C7-C11芳烷基、C2-C4羟烷基、C3-C8烷氧基烷基、C4-C20二烷基氨基烷基、C3-C14烷氧基羰基烷基或式A基,R13是C1-C12烷基、C2-C4羟烷基、C2-C7链烯基、C5-C8环烷基、苯基、被卤素、C1-C4烷基或C1-C4烷氧基取代的苯基、C2-C20烷酰基、C3-C8烯酰基、苯甲酰基、苯乙酰基或式B的三嗪基或R12和R13在一起是可由-O-或-N(R8)-断开的C4-C8亚烷基,或R12和R13在一起是下式基其中:R21是C1-C18烷基,R14是C1-C18烷基、C5-C8环烷基或C7-C9苯烷基,或二个R14基在一起是C2-C6亚烷基、邻亚苯基或邻亚二甲苯基,R15是氢、C1-C12烷基、C3-C5链烯基、C7-C9苯烷基、C2-C4羟烷基、C3-C8烷氧基烷基或C3-C14烷氧基羰基烷基,R16是氢、C1-C12烷基、烯丙基或苄基,R17是C1-C12亚烷基、亚乙烯基、亚环己基、亚二甲苯基或C6-C12亚芳基,R18是C1-C16烷基、C2-C6链烯基、C5-C8环烷基、C7-C9苯烷基、苯基或被卤素、硝基、C1-C4烷基、羟基或C1-C4烷氧基取代的苯基、或被羟基和C1-C4烷基取代的C7-C9苯烷基,R19定义同R1,和R20是Cl、-OH、-OR3、-SR3或-NR4R5。
如果取代基是烷基,该烷基可是直链的或支链的,其例子是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异戊基、正己基、正庚基、正辛基、2-乙基己基、异癸基、正十二烷基、正十六烷基或正十八烷基。在上下文中作为羟烷基的R12、R18和R15可以是如2-羟丙基、3-羟丙基或2-羟丁基,而特别是2-羟乙基。
作为烷氧基烷基的R12和R15可以是如2-甲氧基乙基、2-乙氧基乙基、2-甲氧基丙基、2-丁氧基丙基或2-己氧基乙基。作为二烷基氨基烷基的R12可以是如2-二甲基氨基乙基、2-二丁基氨基乙基、2-二乙基氨基丙基或2-二己基氨基乙基。
作为C2-C8链烯基的R18特别可以是乙烯基或2-丙烯基。作为链烯基的R12、R13和R15可以特别是烯丙基或甲代烯丙基。
作为C7-C9苯烷基的R6、R7、R14、R16、R17和R18特别可以是苄基或苯乙基。作为C7-C12芳烷基的R12可以是如苄基、苯乙基或萘甲基。
作为环烷基的R7、R11、R12、R13、R14和R18特别可以是环己基。
作为烷酰基的R6、R7、R13和R17可以是直链的或支链的,其实例为乙酰、丙酰、异丁酰、己酰、辛酰、月桂酰或硬脂酰。作为烷酰基的R6特别可是丙烯酰或甲基丙烯酰。
作为亚烷基的R9可以是直链的或支链的,或由杂原子断开的。其实例是二、三、四、六、八、十或十二亚甲基,2,2-二甲基三亚甲基,或2,2,4-三甲基四亚甲基,3-氧杂五亚甲基,3-氮杂五亚甲基,2-甲基氮杂五亚甲基,4-丁基氮杂七亚甲基或3,6-二氮杂八亚甲基。
R4和R5在一起以及R12和R13在一起可以是由-O-或-N(R8)-断开的C4-C8亚烷基,这样,它们与其键合的N原子在一起形成最好是5元或6元杂环。其实例是吡咯烷、哌啶、2,6-二甲基哌啶、吗啉、哌嗪、4-甲基哌嗪或4-乙酰基哌嗪。
作为亚烯基的R9特别可以是1,4-亚丁-2-烯基。作为亚环烷基的R9特别可以是1,4-亚环己基。
如果R2是C3-C20烷烃三基,这种基可以是直链的或支链的。其实例是丙烷-1,2,3-三基、丁烷-1,3,4-三基、戊烷-1,3,5-三基或2-甲基戊烷-1,3,5-三基。
式II中那些优选的化合物中n为1-4的整数,R1是Cl、-OR8或-NR4R5,其中R3、R4和R5定义同前,如果n=1,R2为Cl、OR3或-NR4R5,如果n=2,R2为基-N(R10)-R9-N(R10)-或 其中R9和R10定义同前,如果n=3,R2为下式基:和如果n=4,R2为下式基:其中a是2或3和b是2至8,和y为下式基:或
其中R11、R12、R13和R14定义同前。
在这些化合物中,式II中优选的那些化合物中n=1,且R1和R2相同。
特别优选的式II化合物中n=1,相互无关的R1和R2是Cl或-NR4R5,R4是氢或C1-C12烷基,R5是C1-C12烷基,或R4和R5在一起是五亚甲基或3-氧杂五亚甲基,和y是下式基:或 其中R11是氢、C1-C12烷基或-CO-R18,且R18是C1-C18烷基或苯基,R14是C1-C14烷基和R15是氢或C1-C12烷基。
由n当量的XV与化合物R2-(H)n反应,可在第三反应步骤中得到式II的目的化合物。
在不分离中间产物XIV和XV的情况下,可进行各个反应步骤。所有三个反应步骤最好在补加作为HCl夹带剂的碱的惰性溶剂中进行。
适合的溶剂的例子是苯、甲苯或二甲苯。适合的碱的例子是叔胺,如三丁胺或二甲基苯胺,或碱金属氢氧化物,如NaOH或KOH,或碱金属碳酸盐,如Na2CO3或K2CO3。过量的哌啶XII也可作为HCl的夹带剂。
反应最好在加热反应混合物的时进行。当反应进行时,碱最好是连续加到该物料中。反应的进行,如可通过分析结合和/或电离氯来控制。检查反应的另一种可能的方法是色谱分析反应混合物。
为了分离产物,适于将碱的盐过滤出去或用水萃取,并蒸发有机溶液。如果洗涤分离中间产物,使用相同的方法。
用另一种方法,中间产物XIV可首先与R2(H)n反应,接着与R1H反应。如果R1和R2是相同的,则第二和第三反应步骤可通过XIV与2当量R1H反应而合并。
显而易见的是在第一步中使用在反应条件下其y基对氰尿酰氯是情性的那些化合物XIII。特别是y不应含有游离的OH、NH、SH基。接着II的三步合成:原来(情性)的y基可在另一反应或接着的反应中转化成另一个y基。例如原来的缩酮基 可水解成酮基 酮基可还原成 H基,该基可再醚化或酯化,同时形成 酮基 可通过还原胺化转化成氨基CH-NHR12,然后,通过相应的N-取代作用可将上述氨基CH-NHR12转化成 基。
用相似的方法,可使用其他已知反应转化y基。
式II各个化合物的实例是下述化合物:
n R1 R2 Y1 -N(C2H5)2 1 (C4H9)2N- -N(CH2CH2OH)2 1 =R1 1 HOCH2CH2MH- =R1 2 C4H9NH- -NH-(CH2)6-NH- 2 MOCH2CH2NH- -NH-(CH2)6-NH- 2 (C4H9)2N- -NH-CH2CH2-NH- 3 C4H9NH- 1 (C2H9)2N- 1 HOCH2CH2NH- =R1 1 (C4H9)2N- =R1
n R1 R2 Y1 (C2H9)(CH3)N- =R1 1 (C4H9)(CH3)N- =R1 1 -NHC5H17 1 (CH3)2N- =R1 1 C4H9NH- =R1 1 (CH3)2N- =R1 1 C4H9NH- =R1 1 (C2H5)2N- =R1 1 (CH3)2N- =R1 1 (C4H9)2N- =R1
n R1 R2 Y1 (C4H9)(CH3)N- =R1 1 (C4H9)2N- =R1 1 C4H17NH- =R1 1 (CH3)2N- =R1 1 (C4H9)2N- =R1 1 =R1 2 C4H9NH- -NHCH2CH2OOC-(CH2)4-COOCH2CH2NH-
2)式III化合物其中p是2、3或4,R19和R20定义同前,并且如果p=2,Z是如下基团之一其中:R22是C2-C12亚烷基、C4-C8亚烯基、亚二甲苯基或-CO-,R23是C1-C12亚烷基、亚乙烯基、亚环己烯基、亚二甲苯基、C6-C12亚芳基或被卤素、硝基或C1-C4烷基取代的或直接键合的亚苯基,R24是氢、C1-C12烷基、C5-C8环烷基、C7-C9苯烷基、C3-C7链烯基、C2-C18烷酰基、C3-C7烯酰基或苯甲酰基,R25是C2-C12亚烷基、由NH或O断开的C4-C16亚烷基、C4-C8亚烯基、亚二甲苯基或亚环己基,R26是氢、C1-C12烷基、C5-C8环烷基或式A基,R27定义同R28或是-NH-R28-NH-基,R28是C2-C12亚烷基或可被C1-C4烷基取代的C6-C12亚芳基,R29是氢、C1-C12烷基、C2-C18烷酰基或式B的三嗪基,和R1与开始定义相同,且如果P=3,Z是下述基团之一其中R30是C3-C18烷烃三基或C6-C12芳烃三基,如果P=4,Z是下述基团之一其中R31是C4-C16烷烃四基或C6-C12芳烃四基。
如果R24、R26或R29是C1-C12烷基,则其可以是直链或支链的烷基,如甲基、乙基、异丙基、正丁基、仲丁基、异戊基、正己基、正辛基、2-乙基己基、正癸基或正十二烷基。作为C3-C7链烯基的R24特另可以是烯丙基。
作为C5-C8环烷基的R24和R26特别可以是环己基。作为C7-C9苯烷基的R24特别可以是苄基。
作为C2-C18烷酰基的R24和R29可以是直链或支链的,其实例且阴!⒈!⒍□!⑿刘!⒃鹿瘐;蛴仓!W魑狢3-C7烯酰基的R24特别可以是丙烯酰或甲基丙烯酰。
作为C2-C12亚烷基的R22、R25和R28可以是直链的或支链的,其实例是二、三、四、六、八、十或十二亚甲基、2,2-二甲基三亚甲基、二乙基亚甲基或2,2,4-三甲基四亚甲基。并且,作为C1-C14亚烷基的R23也可以是如亚甲基或十四亚甲基。作为断开的亚烷基的R25可以是如3-氧杂五亚甲基、3-氮杂五亚甲基、3-甲基氮杂五亚甲基或4-氧杂五亚甲基。作为C4-C8亚烯基的R22特别可以是1,4-亚丁-2-烯基。
作为C6-C12亚芳基的R23和R28可以是如亚苯基、二亚苯基或亚萘基。
作为三价基的R30可以是如丙烷-1,2,3-三基、丁烷-1,2,4,-三基、苯-1,2,4-三基或萘-1,4,6-三基。
作为四价基的R31可以是如丁烷-1,2,3,4-四基、苯-1,2,4,5-四基或萘-1,4,5,8-四基。
式III的那些优选的化合物中P为2,3或4,且相互无关的R19和R20是-OR3或-NB4R5,其中R3、R4和R5定义同前,如果P=2,Z是下述基团之一
其中R28、R24、R25和R26定义同前,如果P=3,Z是下述基团之一或 其中R30是C3-C8烷烃三基或C6-C12芳烃三基和R26定义同前,以及如果P=4,Z是下式基其中R31是C4-C12烷烃四基或C6-C12芳烃四基。
在这些化合物中,优选的式III化合物中R10和R20是相同的。
为制备式III化合物,在第一步中P当量的氰尿酰氯可与二、三或四哌啶化合物XVI反应。
然后在二个另外的反应步骤中,中间产物XVII可与R19H和R20H反应。如果R19和R20是相同的,它们可在一步中引入。
各个反应步骤指的是在三嗪环上逐步取代三个氯原子。它们可按照前面合成II所叙述的方法进行。
用另一种方法,式XVIII化合物可按照制备II所叙述的方法制备,上述化合物可与二、三或四价反应物XIX反应。例如,如果y是 基,化合物Hal-R22-Hal、ClCO-R28 COCl、AlkOOC-R28,-COOAlk 或
可用作二价反应物XIV。化合物(ClCO)3R30、(AlkOOC)3R30或氰尿酰氯可用作三价反应物XIX,和化合物(ClCO)4R31或(AlkOOC)4R31可用作四价反应物XIX,其中Hal是卤原子和Alk是C1-C4烷基。
p R19 R20 Z2 iso-C3H7NH- =R19 2 C4H9NH- =R19 2 (C2H5)2N- =R19 2 (CH3)2N- =R19 2 -NHC4H9 2 C8H17NH- =R19 2 C4H9NH- =R19 2 (C2H5)2N- =R19 2 (C4H9)(CH3)N- =R19
p R19 R20 Z2 (C4H9)(CH3)N- =R19 3 (C4H9)2N- =R1 4 C4H9NH- -N(CH3)2 2 (CH3)2CHNH- =R19 4 C4H9O- =R19 2 =R19
3)式IV化合物其中:r具有3至50的数值,相互无关的Q和Q′是-O-、-S-或-N(R10)-,且Y、R9和R10定义同前,或其中-Q-R9-Q′-是基-NHNH-、或 最好r具有3至25的数值,Q和Q′是-O-或-N(R10)。
这些化合物可通过二氯代三嗪XIV与化合物HQ-R9-Q′H反应来制备。后面的化合物可以是如二醇、二硫醇、二胺或羟基胺。根据两种离析物的摩尔比,而得到具有高或低缩聚度r的产物。在用于结合形成的HCl的碱的存在下,进行缩聚作用。
式IV化合物的实例是如下化合物:
Y Q Q R9 NH NH -(CH2)6- O O -(CH2)4- NH NH -(CH2)6- NH NH -CH2CH2OCC(CH2)2COOCH2CH2- O O NH NH -CH2CH2NHCH2CH2-(C4H9)2N NH NH -(CH2)3-O-(CH2)3-
其中:r具有3至50的数值,y和R1定义同前,An是C2-C4亚烷基,且R23定义同前。
这些化合物可由式XV的一氯代三嗪与化合物HN(AnOH)2反应,并接着与二羧酸二烷基酯缩聚来制备。其中Alk是C1-C4烷基。An最好为-CH2CH2-。这里缩聚度r亦可随着离析物摩尔比的变化而改变。可使用的二羧酸二烷基酯的实例是琥珀酸二甲酯、己二酸二乙酯、癸二酸二甲酯、对苯二酸二甲酯或间苯二酸二乙酯。
式V化合物的实例是如下化合物:
Y R1 An R23 -N(C4H9)2 -CH2CH2- -CH2CH2- -Cl2CH2- -N(C2H5)2 -CH2CH2- -(CH2)4- -NHC4H9 -(CH2)8 -CH2CH2- -CH2CH2-
其中q、R16、R22、R23、R24、R25、R26、R27和R29定义同前。
这些化合物可首先通过如(1)中所述的逐步取代氰尿酰氯制备式XX化合物,其中y含有OH或NH基,。然后,将其与双官能反应物反应来制备。例如,如果Y是CH-OH基,化合物Hal-R22-Hal或AlkOOC-R23-COOAlk可用作双官能反应物。
式VI化合物的实例是如下化合物:
-N(C4H9)2
6)式VII化合物其中:S是0或1,t是0或2,而u具有5至100的数值,Q″是-O-、-NH或-N(C1-C4烷基)-,R34是氢或甲基,相互无关的R35和R36是-OR3、-SR3或-NR4R5,和这种化合物与(甲基)丙烯酸、(甲基)丙烯酸烷基酯、(甲基)丙烯酸羟烷基酯或马来酐的共聚物。
该化合物可通过下式XXIII单体聚合或通过XXIII与(甲基)丙烯酸、(甲基)丙烯酸烷基酯、(甲基)丙烯酸羟烷基酯或马来酐共聚合来制备。使用游离基聚合反应引发剂,如有机过氧化物或偶氮化合物,进行聚合反应。单体XXIII可通过如(1)中所叙的逐步取代氰尿酰氯的方法来制备。
式VIII的那些优选的化合物中S=1,t=0和Q″是-O-。
其中:r具有3至50的数值,t是0或2,Q和Q′定义同前,Q″是-O-、-NH-或-N(C1-C4烷基)-,且R9、R35和R36定义同前。
这些化合物可通过式XXIV化合物在两当量碱存在下,与双官能化合物HQ-R9-Q′H缩聚来制备。离析物XXIV可通过如(1)中所述的逐步取代氰尿酰氯的方法来制备。
式VIII中那些优选的化合物中t=0。
8)式IX化合物其中:V具有2至30的数值,t是0或2,R35和R36定义同前,R37是C2-C8亚烷基、C4-C8亚烯基、亚二甲苯基、-CH2-CH(OH)-CH2-或-CH2CH(OH)CH2-O-R39-O-CH2CH(CH)CH2-,R38定义同R37或是 或 R39是C2-C8亚烷基、亚苯基或和R27定义同前。
如果R38同R37,式IX化合物可由下式XXVI伯胺与Hal-R37-Hal、表氯醇或二环氧甘油醚XXVa反应来制备。离析物XXV和XXVI可通过如(1)或(2)中所叙述的逐步取代氰尿酰氯的方法来制备。
式IX化合物的实例是:
9)式X化合物
其中:t是0或2,V具有2至30的数值,An是C2-C4亚烷基,且R19、R20和R23定义同前。
与二羧酸二烷基酯AlkOOC-R28-COOAlk缩聚来制备。式X的那些优选的化合物中t是0和An是-CH2CH2-。
离析物XXVII可通过如(1)中所叙述的逐步取代氰尿酰氯来制备。
10)式XI化合物
与一当量下式化合物
离析物XXVIII和XXVIIIa可通过(1)中所叙述的逐步取代氰尿酰氯的方法来制备。
为制备这些化合物,式XXIX双哌啶化合物
式IV至X和XII化合物是聚合物,其中的结构式表示重复的分子单元。这些聚合物的端基可以是来自离析物或聚合催化剂的相应基团。将聚合产物限定在所希望的分子量范围内是通过在制备(聚合)中添加单官能化合物或链终止剂来达到的。在这种情况下,也可形成相应于这些添加剂的端基。
本发明的化合物可用作为抗由光、氧和热而造成损伤的有机材料的稳定剂。这种被稳定的材料可以是,如油、脂肪、腊、化妆品、生物杀伤剂、或照相的或重印材料。在存在于塑料、橡胶、油添或粘合剂的聚合材料中使用具有特别的意义。如此稳定的聚合物的实例如下:
1.单和二烯烃聚合物,例如聚丙烯、聚异丁烯、聚丁-1-烯、聚甲基戊-1-烯、聚异戊二烯或聚丁二烯和环烯烃聚合物,如环戊烯或降冰片烯;此外,聚乙烯(交联的或非交联的),如高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)和线性低密度聚乙烯(LLDPE)。
2.上述1)中的聚合物的混合物,例如聚丙烯与聚异丁烯的混合物、聚丙烯与聚乙烯的混合物(如pp/HDPE、pp/LDPE)和各种聚乙烯型的混合物(如LDPE/HDPE)。
3.单和二烯烃相互间的或与其他乙烯基单体的共聚物。例如乙烯-丙烯共聚物、线性低密度聚乙烯(LLDPE)和它与低密度聚乙烯(LDPE)的混合物、丙烯-丁-1-烯共聚物、丙烯-异丁烯共聚物、乙烯-丁-1-烯共聚物、乙烯-己烯共聚物、乙烯-甲基戊烯共聚物、乙烯-庚烯共聚物、乙烯-辛烯共聚物、丙烯-丁二烯共聚物、异丁烯-异戊二烯共聚物、乙烯-丙烯酸烷基酯共聚物、乙烯-甲基丙烯酸烷基酯共聚物、乙烯-乙酸乙烯酯共聚物或乙烯-丙烯酸共聚物和它们的盐(离聚物);也可是乙烯与丙烯和二烯的三元共聚物,二烯类如己二烯、二环戊二烯或亚乙基降冰片烯;此外,这些共聚物相互之间和与1)中所述聚合物的混合物,例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-乙酸乙烯酯共聚物、LDPE/乙烯-丙烯酸共聚物、LLDPE/乙烯-乙酸乙烯酯共聚物和LLDPE/乙烯-丙烯酸共聚物。
3a.烃类树脂(例如C5-C9),包括它的氢化改性物(例如粘性树脂)。
4.聚苯乙烯、聚(对甲基苯乙烯)、聚(α-甲基苯乙烯)。
5.苯乙烯或α-甲基苯乙烯与二烯烃或丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丙烯腈、苯乙烯-甲基丙烯酸烷基酯、苯乙烯-丁二烯-丙烯酸烷基酯、苯乙烯-马来酐、苯乙烯-丙烯腈-丙烯酸甲基酯;耐冲击强度苯乙烯共聚物和其他聚合物的混合物,如聚丙烯酸酯、二烯聚合物或乙烯-丙烯-二烯三元聚合物;也可是苯乙烯的嵌段共聚物,如苯乙烯-丁二烯-苯乙烯、苯乙烯-异戊二烯-苯乙烯、苯乙烯-乙烯/丁烯-苯乙烯或苯乙烯-乙烯/丙烯-苯乙烯。
6.苯乙烯或α-甲基苯乙烯接枝共聚物,例如在聚丁二烯上的苯乙烯、在聚丁二烯-苯乙烯上的或聚丁二烯-丙烯腈共聚物上的苯乙烯、在聚丁二烯上的苯乙烯和丙烯腈(或甲基丙烯腈);在聚丁二烯上的苯乙烯、丙烯腈和甲基丙烯酸甲酯;在聚丁二烯上的苯乙烯和马来酐;在聚丁二烯上的苯乙烯、丙烯腈和马来酐或马来酰亚胺;在聚丁二烯上的苯乙烯和马来酰亚胺、在聚丁二烯上的苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯、在乙烯-丙烯-二烯三元共聚物上的苯乙烯和丙烯腈、在聚(丙烯酸烷基酯)或聚(甲基丙烯酸烷基酯)上的苯乙烯和丙烯腈、在丙烯酸酯-丁二烯共聚物上的苯乙烯和丙烯腈,也可以是它与上述5)中共聚物的混合物,这些已是公知的,例如被称为ABS、MBS、ASA或AES聚合物。
7.含有卤素的聚合物,例如聚氯丁橡胶、氯化橡胶、氯化或氯磺化聚乙烯、表氯醇的均聚物和共聚物,特别是含有卤素的乙烯基化合物的聚合物,例如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏氟乙烯;也可以是它们的共聚物,如氯乙烯-1,1-二氯乙烯、氯乙烯-醋酸乙烯酯或1,1-二氯乙烯-醋酸乙烯酯。
8.由α、β未饱和酸和它们的衍生物衍生出来的聚合物,如聚丙烯酸酯和聚甲基丙烯酸酯、聚丙烯酰胺和聚丙烯腈。
9.上述8)中的单体相互之间或与其他未饱和的单体的共聚物,例如丙烯腈-丁二烯共聚物、丙烯腈-丙烯酸烷基酯共聚物、丙烯腈-丙烯酸烷氧基烷基酯共聚物、丙烯腈-乙烯基卤化物共聚物或丙烯腈-甲基丙烯酸烷基酯-丁二烯三元聚合物。
10.由未饱和醇和胺或它们的酰基衍生物或乙缩醛衍生出来的聚合物,如聚乙烯醇、聚乙酸乙烯酯、硬脂酸酯、苯甲酸酯或马来酸酯、聚乙烯醇缩丁醛、聚(邻苯二甲酸烯丙酯)、聚烯丙基三聚氰胺;和它们与上述1中烯烃的共聚物。
11.环醚的均聚物和共聚物,如聚(亚烷基)二醇、聚环氧乙烷、聚环氧丙烷或它与双缩水甘油醚的共聚物。
12.聚缩醛,如聚甲醛、和也可是含有共聚用单体,如环氧乙烷的那些聚甲醛;热塑性聚氨基甲酸乙酯、丙烯酸酯或MBS改性了的聚缩醛。
13.聚苯氧化物和硫化物及其与苯乙烯聚合物或聚酰胺的混合物。
14.由带有末端羟基和同时带有脂族或芳族的聚异氰酸酯的聚醚、聚酯和聚丁二烯衍生出来的聚氨基甲酸乙酯,和它们的前体。
15.由二胺和二羧酸和/或氨基羧酸或相应的内酰胺衍生出来的聚酰胺和共聚酰胺,例如聚酰胺4、聚酰胺6、聚酰胺6/6、6/10、6/9、6/12、4/6、聚酰胺11、聚酰胺12、由间二甲苯、二胺和己二酸而得到的芳族聚酰胺;由六亚甲基二胺和间和/或对苯二酸和,当需要时,作为改性剂的高弹体而制备的聚酰胺,例如聚-2,4,4-三甲基六亚甲基对苯二酰胺和聚间亚苯基间苯二酰胺。上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合的或接枝高弹体的嵌段共聚物;或者是与聚醚、如聚乙二醇、聚丙二醇或聚丁二醇的嵌段共聚物。此外,与EPDM或ABS改性的聚酰胺或共聚酰胺的嵌段共聚物;和也可是在工艺过程中缩合了的聚酰胺(“RIM聚酰胺体系”)。
16.聚脲、聚酰亚胺、聚酰胺-聚酰亚胺和聚苯并咪唑。
17.由二羧酸和二醇和/或由羟基羧酸或相应的内酯衍生的聚酯,例如聚对苯二甲酸乙酯、聚对苯二甲酸丁酯、聚-1,4-二甲基醇环己烷对苯二甲酸酯、聚羟基苯甲酸酯,也可以是由具有羟基端基的聚醚衍生出来的嵌段聚醚酯;此外,具有聚碳酸酯或MBS改性的聚酯。
18.聚碳酸酯和聚酯碳酸酯。
19.聚砜、聚醚砜和聚醚酮。
20.由醛、同时也由酚、脲或密胺而衍生得到的交联聚合物,如苯酚-甲醛、脲-甲醛和密胺-甲醛树脂。
21.干燥和非干燥的醇酸树脂。
22.未饱和聚酯树脂,它是由饱和和未饱和二羧酸与多元醇的共聚酯衍生得到的,也可以用乙烯化合物作为交联剂,并也可含有卤素、不可燃的变体。
23.交联丙烯酸树脂,它是由取代的丙烯酸酯衍生而得到的,例如环氧丙烯酸酯、聚氨酯丙烯酸酯或聚酯丙烯酸酯。
24.与密胺树脂、脲树脂、聚异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂和丙烯酸树脂。
25.交联环氧树脂,它是由聚环氧化合物,如二缩水甘油基醚或由环脂族二环氧化物衍生而得到的。
26.天然聚合物,如纤维素、天然橡胶、明胶和也可是它们的化学衍生出的聚合同系衍生物,如乙酸纤维素、丙酸酯和丁酸酯,或纤维素醚,如甲基纤维素;也可是松香树脂和衍生物。
27.前面提到的聚合物的混合物(复合高聚物),例如PP/EPDM、聚酰胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/热塑性PUR、PC/热塑性PUR、POM/丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA6.6和共聚物、PA/HDPE、PA/PP和PA/PPO。
聚烯烃和粘合剂对于油漆的稳定作用是特别重要的。
将稳定剂以0.01~5%重量(以被稳定的材料为准计算)适量地添加到有机材料中,优选使用0.1~2%(重量)。甚至可在制备过程中(聚合)添加到聚合物质中,最好是在聚合物成型之前或成型期间加入。
在某种情况下,使用二种或多种本发明的稳定剂的混合物是有利的。
其他的稳定剂或各种通常的添加剂也可以与本发明的稳定剂一起加入到有机物质中。该实例是以下添加物:
1。 抗氧剂
1.1.烷基化的单酚,例如2,6-二叔丁基-4-甲基酚、2-叔丁基-4,6-二甲基酚、2,6-二叔丁基-4-乙基酚、2,6-二叔丁基-4-正丁基酚、2,6-二叔丁基-4-异丁基酚、2,6-二环戊基-4-甲基酚、2-(α-甲基环己基)-4,6-二甲基酚、2,6-二辛基-4-甲基酚、2,4,6-三环己基酚、2,6-二叔丁基-4-甲氧基甲基酚、2,6-二壬基-4-甲基酚。
1.2.烷基化的氢醌,如2,6-二叔丁基-4-甲氧基酚、2,5-二叔丁基-氢醌、2,5-二叔戊基-氢醌、2,6-二苯基-4-十八烷氧基酚。
1.3.羟基化的二苯基硫醚,例如2,2′-硫代-双(6-叔丁基-4-甲基酚)、2,2′-硫代-双(4-辛基酚)、4,4′-硫代-双(6-叔丁基-3-甲基酚)、4,4′-硫代-双(6-叔丁基-2-甲基酚)。
1.4.亚烷基双酚,例如2,2′-亚甲基-双(6-叔丁基-4-甲基酚)、2,2′-亚甲基-双(6-叔丁基-4-乙基酚)、2,2′-亚甲基-双〔4-甲基-6-(α-甲基环己基)酚〕、2,2′-亚甲基-双(4-甲基-6-环己基酚)、2,2′-亚甲基-双(6-壬基-4-甲基酚)、2,2′-亚乙基-双(4,6-二叔丁基酚)、2,2′-亚乙基-双(4,6-二叔丁基酚)、2,2′-亚乙基-双(6-叔丁基-4-异丁基酚)、2,2′-亚甲基-双〔6-(α-甲苄基)-4-壬基酚〕、2,2′-亚甲基-双〔6-(α,α-二甲苄基)-4-壬基酚〕、4,4′-亚甲基-双(2,6-二叔丁基酚)、4,4′-亚甲基-双(6-叔丁基-2-甲基酚)、1,1-双(5-叔丁基-4-羟基-2-甲苯基)丁烷、2,6-双(3-叔丁基-5-甲基-2-羟苄基)-4-甲基酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基酚)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲苯基)-3-正十二烷巯基丁烷、乙二醇-双〔3,3-双-(3′-叔丁基-4′-羟苯基)丁基酯〕、双(3-叔丁基-4-羟基-5-甲苯基)二环戊二烯、双〔2-(3′-叔丁基-2′-羟基-5′-甲-苄基)-6-叔丁基-4-甲苯基〕对苯二酸酯。
1.5.苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟苄基)-2,4,6-三甲基苯、双(3,5-二叔丁基-4-羟苄基)硫、3,5-二叔丁基-4-羟苄基巯基乙酸异辛酯、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二酸酯、1,3,5-三(3,5-二叔丁基-4-羟苄基)异氰脲酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酯、3,5-二叔丁基-4-羟苄基次磷酸双十八烷基酯、3,5-二叔丁基-4-羟苄基-膦酸单乙基酯的Ca盐、1,3,5-三(3,5-二环己基-4-羟苄基)异氰脲酯。
1.6.酰氨基酚,例如4-羟基-月桂酰苯胺、4-羟基硬脂酰苯胺、2,4-双(辛基巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-S-三嗪、N-(3,5-二叔丁基-4-羟苯基)氨基甲酸辛酯。
1.7.β-(3,5-二叔丁基-4-羟基苯基)丙酸与-元或多元醇的酯,例如与甲醇、十八醇、1,6-己二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰脲酯、N,N′-双(羟乙基)草酸胺。
1.8.β-(5-叔丁基-4-羟基-3-甲苯基)丙酸与-元或多元醇的酯,例如与甲醇、十八醇、1,6-己二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰脲酯、N,N′-双(羟乙基)草酰胺的酯。
1.9.β-(3,5-二环己基-4-羟苯基)丙酸与一元或多元醇的酯,例如与甲醇、十八醇、1,6-己二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰脲酯、N,N′-双(羟乙基)草酸酰胺的酯。
1.10.β-(3,5-二叔丁基-4-羟苯基)丙酸的酰胺,例如N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)六亚甲基二胺、N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)三亚甲基二胺、N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)肼。
2.UV吸收剂和光稳定剂
2.1。2-(2′-羟苯基)苯并三唑,例如5′-甲基、3′,5′-二叔丁基、5′-叔丁基、5′-(1,1,3,3-四甲基丁基)、5-氯-3′,5′-二叔丁基、5-氯-3′-叔丁基-5′-甲基、3′-仲丁基-5′-叔丁基、4′-辛氧基、3′,5′-二叔戊基、3′,5′-双(α,α-二甲苄基)衍生物。
2.2. 2-羟基二苯酮,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2′,4′-三羟基、2′-羟基-4,4′-二甲氧基衍生物。
2.3.取代或未取代的苯甲酸酯,例如水杨酸4-叔丁基苯酯、水杨酸苯酯、水杨酸辛苯酯、二苯甲酰基间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯、3,5-二叔丁基-4-羟基苯甲酸十六烷基酯。
2.4。丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙酯或异辛酯、α-甲酯基-肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸甲酯或丁酯、α-甲酯基-对甲氧基肉桂酸甲酯、N-(β-甲酯基-β-氰基乙烯基)-2-甲基-二氢吲哚。
2.5.镍化合物,例如2,2′-硫代-双〔4-(1,1,3,3-四甲基丁基)酚〕的镍配合物,如1∶1或1∶2的配合物,如果需要可外加配位体,如正丁胺、三乙醇胺或N-环己基二乙醇胺;二丁基二硫代氨基甲酸镍;4-羟基-3,5-二叔丁基苄基膦酸单烷基酯(如甲酯或乙酯)的镍盐;酮肟(如2-羟基-4-甲苯基十一烷基酮肟)的镍配合物;1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,如果需要,可外加配位体。
2.6。位阻胺,例如双(2,2,6,6-四甲基哌啶基)癸二酸酯、双(1,2,2,6,6-五甲基哌啶基)癸二酸酯、双(1,2,2,6,6-五甲基哌啶基)正丁基-3,5-二叔丁基-4-羟苄基丙二酸酯、由1-羟乙基-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩合物、由N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛氨基-2,6-二氯-1,3,5-S-三嗪的缩合物、三(2,2,6,6-四甲基-4-哌啶基)次氮三乙酸酯、四(2,2,6,6-四甲基-4-哌啶基)1,2,3,4-丁烷四羧酸酯、1,1′-(1,2-亚乙基)-双(3,3,5,5-四甲基哌啶酮)。
2.7.草酰胺,例如4,4′-二辛氧基-N,N′-草酰二苯胺、2,2′-二辛氧基-5,5′-二叔丁基-N,N′-草酰二苯胺、2,2′-双十二烷氧基-5,5′-二叔丁基-N,N′-草酰二苯胺、2-乙氧基-2′-乙基-N,N′-草酰二苯胺、N,N′-双(3-二甲氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2′-乙基-N,N′-草酰二苯胺和它与2-乙氧基-2′-乙基-5,4′-二叔丁基-N,N′-草酰二苯胺的混合物、邻和对甲氧基及邻和对乙氧基二取代的N,N′-草酰二苯胺的混合物。
2.8。2-(2-羟苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛氧苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧苯基)-4,6-双(2,4-二甲苯基)-1,3,5-三嗪、2-(2,4-二羟苯基)-4,6-双(2,4-二甲苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙氧苯基)-6-(2,4-二甲苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧苯基)-4,6-双(4-甲苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧苯基)-4,6-双(2,4-二甲苯基)-1,3,5-三嗪。
3.金属减活剂,例如N,N′-二苯基草酰胺、N-水杨醛-N′-水杨酰肼、N,N′-双(水杨酰)肼、N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)肼、3-水杨酰氨基-1,2,4-三唑、双(亚苄基)草酸二肼。
4.亚磷酸酯和次膦酸配,例如亚磷酸三苯酯、亚磷酸二苯基烷基酯、亚磷酸苯基二烷基酯、亚磷酸三(壬苯基)酯、亚磷酸三月桂酯、亚磷酸-三-十八烷基酯、二硬脂酰基-季戊四醇二亚磷酸酯、三(2,4-二叔丁苯基)亚磷酸酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二叔丁苯基)季戊四醇二亚磷酸酯、三硬脂酰基-山梨糖醇三亚磷酸酯、四(2,4-二叔丁苯基)-4,4′-亚联苯二次膦酸酯、3,9-双(2,4-二叔丁苯基)-2,4,8,10-四氧杂-3,9-二磷杂螺〔5,5〕十一烷。
5。过氧化物-破坏化合物,例如β-硫代-二丙酸酯,如月桂基、硬脂酰基、十四烷基或十三烷基酯;巯基苯并咪唑;2-巯基苯并咪唑的锌盐;二丁基二硫代氨基甲酸锌;双十八烷基二硫;季戊四醇-四(β-十二烷基巯基)丙酸脂。
6.聚酰胺稳定剂,例如与碘化物和/或磷化合物共同结合的铜盐和二价镁的盐。
7.碱性共稳定剂,例如密胺、聚乙烯吡咯烷酮、双氰胺、氰尿酸三烯丙基酯、尿素衍生物、肼的衍生物、胺、聚酰胺、聚氨基甲酸乙酯、高级脂肪酸的碱金属和碱土金属的盐,如硬脂酸钙、硬脂酸锌、硬脂酸镁、蓖麻醇酸钠、棕榈酸钾、邻苯二酚酸氧锑或邻苯二酚酸锡。
8.成核剂,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸。
9。填充剂和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨。
10。各种添加剂,例如软化剂、润滑剂、乳化剂、颜料、荧光增白剂、阻燃剂、抗静电剂、推进剂。
由于另外使用了这样的共稳定剂,可以产生协同效应,特别是在另外使用UV吸收剂时,情况更是这样。
当本发明化合物用于作为照相材料的稳定剂时,使用在感光层上,如在胶片上或照相纸上特别有意义。
本发明的某些化合物也可以在本发明的其他化合物的制备中用作中间体,特别是将其应用到在三嗪环上具有氯原子的化合物上。在三嗪基上不含有氯原子的那些化合物可作为优选的稳定剂。
在以下的实施例中,更详细地说明了本发明化合物的制备和使用。在这些实施例中,份数和百分数都是以重量计的,给出的温度是摄氏温度。
实施例1:2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在400ml的二甲苯中,在120℃下,将92.2g的氰尿酰氯和142.6g 2,2,6,6-四甲基哌啶搅拌10小时。冷却至室温后,从生成的2,2,6,6-四甲基哌啶盐酸盐中过滤出溶液,后者用100ml二甲苯洗涤。每次用100ml水将二甲苯溶液从黄色到棕色洗涤三次,经硫酸钠干燥,再与5g Tonsiloptimum(漂白土)和5g骨炭搅拌10分钟,澄清并在真空下蒸发。得到的残余物适宜用另外加有3g Tonsil的300ml己烷中重结晶,得到2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪无色晶体,熔点为129°。
实施例2:2,4-二氯-6-(2,2,6,6-四甲基-4-苯甲酰氧基哌啶-1-基)-1,3,5-三嗪。
46.1g氰尿酰氯和136.0g 2,2,6,6-四甲基-4-苯甲酰氧基哌啶,在300ml的二甲苯中,按上述实施例1所述的方法进行反应和处理。由异丙醇重结晶后,得到2,4-二氯-6-(2,2,6,6-四甲基-4-苯甲酰氧基哌啶-1-基)-1,3,5-三嗪的无色晶体,熔点为145°。
实施例3:2-氯-4-乙氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在室温下,将15g 70%的乙胺水溶液添加到在250ml乙醇的28。9g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(按实施例1制备)的溶液中,温度迅速升至约35°。接着在55°下将混合物搅拌12小时,加入25ml水,将混合物冷却至5°。过滤出得到的沉淀物,用200ml水洗涤,并干燥。由乙腈结晶得到2-氯-4-乙氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪无色晶体,熔点为148°。
实施例4:2-氯-4-二乙氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
用15g二乙胺代替乙胺溶液,其他按实施例3所述的方法制备,得到2-氯-4-二乙氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪无色物质,熔点为77°。
实施例5:2,4-双-异丙氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
43.4g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪与200ml二甲苯中的39.0g异丙胺一起在反应釜中加热至160°,保持8小时。冷却至室温后,每次用100ml水将反应釜中物料洗涤三次,硫酸钠干燥浅黄色二甲苯溶液,并与5%Tonsil Optimum(漂白土)一起搅拌10分钟,过滤并蒸发,得到2,4-双-异丙氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪不能结晶的浅黄色树脂。
实施例6:2,4-双-二丁氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
将57.8g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,在室温下悬浮于200ml的二甲苯中,在15分钟内向其中滴加25.8g的二丁基胺,并使温度升至40°。在约15分钟内,把40ml水中的8.8g氢氧化钠溶液加到反应混合物中,接着,在60°下搅拌2小时。然后分离出水相,并把28.4g二丁基胺和在20ml水中的9.6g氢氧化钠溶液加到透明的有机相中。然后在水分离器中加热该混合物直到内部温度约达135°,并在该温度下搅拌12小时。使烧瓶中的物料冷至90°,并加入100ml水的3g氢氧化钠溶液,在90°下,强力搅拌该混合物30分钟。然后分出水相,每次用100ml水将二甲苯溶液洗涤5次,并在真空下蒸发。在高真空下蒸馏淡黄色油状残余物,得到2,4-双-二丁氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪无色油状物,在6.5pa下的沸点为173°。
实施例7:2,4-二吗啉代-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
用36.6g吗啉(第一部份:17.4g;第二部份19.2g)代替二丁基胺,其他按实施例6所述的步骤,得到2,4-二吗啉代-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,用乙醇结晶后,其熔点为147-48°。
实施例8:2,4-二丁氨基-6-(2,2,6,6-四甲基-4-苯甲酰氧基哌啶-1-基)-1,3,5-三嗪。
20.5g 2,4-二氯-6-(2,2,6,6-四甲基-4-苯甲酰氧基哌啶-1-基)-1,3,5-三嗪(按实施例2制备)在200ml二甲苯中与8.0g正丁胺一起回流4小时,并把4.4g粉状的氢氧化钠添加到反应混合物中,在回流下进一步搅拌15小时。烧瓶中的物料被冷至室温,加入100ml水后,剧烈搅拌直到沉淀的盐完全进入到溶液中为止。分出水相,每次用100ml水将二甲苯溶液洗涤三次,在真空下蒸发。在100°和13pa下干燥油状残余物,得到2,4-二丁氨基-6-(2,2,6,6-四甲基-4-苯甲酰基哌啶-1-基)-1,3,5-三嗪淡黄色粘性物。
实施例9:2,4-双丁氨基-6-(2,2,6,6-四甲基-4-羟基哌啶-1-基)-1,3,5-三嗪。
10g 2,4-二丁氨基-6-(2,2,6,6-四甲基-4-苯甲酰氧基哌啶-1-基)-1,3,5-三嗪(按实施例8制备)与50ml甲醇和50ml 20%的氢氧化钠溶液一起在回流下加热6小时。在真空下,从反应混合物中蒸馏出甲醇。将100ml甲苯和50ml水加到残余物中,充份摇动后,分离出水相,每次用50ml水将甲苯溶液洗涤三次。蒸发甲苯溶液后,得到2,4-二丁氨基-6-(2,2,6,6-四甲基-4-羟基哌啶-1-基)-1,3,5-三嗪淡黄色粘性物,由乙腈结晶得到熔点为90°的无色晶体。
实施例10:2,4-二氯-6-(2,2,6,6-四甲基-4-己氧基哌啶-1-基)-1,3,5-三嗪。
将62.7g 4-己氧基-2,2,6,6-四甲基哌啶在搅拌下添加到100ml甲苯的23.9g氰尿酰氯的溶液中,接着把混合物加热到80°,保持24小时。在此期间形成了哌啶盐酸盐的白色沉淀,冷却后,过滤出沉淀物,再用2N盐酸洗涤甲苯溶液数次,经Na2SO4干燥并蒸发。由乙腈重结晶残余物,产物的熔点为49-51°。
实施例11:2,4-二吗啉代-6-(2,2,6,6-四甲基-4-己氧基哌啶-1-基)-1,3,5-三嗪。
将从实施例10得到的9.7g产物与50ml吗啉在回流下加热3小时。将桔色的反应混合物倾入水中,在此期间沉淀的粗产物溶于乙酸乙酯中,并用SiO2柱色谱提纯,提纯后的产物是粘性物。
分析:计算值C=63.64% H=9.44% N=17.12%
实验值C=63.64% H=9.29% N=17.08%
实施例12:用二异丁胺代替实施例11中的吗啉,其他步骤完全与实施例11相同,得到2,4-双(二异丁氨基)-6-(2,2,6,6-四甲基-4-己氧基哌啶-1-基)-1,3,5-三嗪粘性液体。
分析:计算值:C=75.12% H=12.35% N=10.51%
实验值:C=75.36% H=12.08% N=10.54%
实施例13:用二丁胺代替实施例11中的吗啉,其他步骤同实施例11,得到2,4-二(二丁氨基)-6-(2,2,6,6-四甲基-4-己氧基哌啶-1-基)-1,3,5-三嗪粘性物。
分析:计算值:C=71.02% H=11.57% N=14.61%
实验值:C=71.09% H=10.96% N=14.69%
实施例14:2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪和六亚甲基二胺的缩聚物。
在100°下,将50ml二甲苯中的10.5g(90mmol)六亚甲基二胺溶液,在搅拌的同时,缓慢地滴加到50ml二甲苯中的12.4g(43mmol)2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪溶液中,在回流下,反应混合物搅拌22小时。冷却后,过滤混合物,滤液用50ml水洗涤两次,并加入足量的己烷直至不再有沉淀发生为止。过滤出沉淀物,滤液用50ml水洗涤三次,经硫酸镁干燥并蒸发。残物在50°真空下干燥,得到分子量 Mn=1029/ Mw=1545(凝胶渗透色谱法)的树脂聚合物。
实施例15:2,4-二氯-6-(1,3,8-三氮杂-2,4-二氧代-3,7,7,9,9-五甲基螺〔4,5〕癸-1-基)-1,3,5-三嗪。
在0-5°下,将200ml二甲苯的35.1g(0.19mol)氰尿酰氯溶液,在搅拌的同时滴加到500ml二甲苯的90.9g(0.38mol)1,3,8-三氮杂-2,4-二氧代-3,7,7,9,9-五甲基螺〔4,5〕癸烷溶液中。接着将混合物加热至回流保持24小时。冷却后,过滤出沉淀物,并洗涤滤液,首先用由乙酸调至PH为5的水洗涤,然后用NaSO4溶液洗涤,最后用水洗涤。过滤二甲苯溶液,经Na2SO4干燥并在真空下蒸发。残余物由70ml乙腈重结晶,得到熔点为237-242℃的棕色粉末。
分析:计算值:C=46.52% H=21.70% N=5.21%
实验值:C=46.40% H=21.85% N=5.22%
实施例16:2,4-二吗啉代-6-(1,3,8-三氮杂-2,4-二氧代-3,7,7,9,9-五甲基螺〔4,5〕癸-1-基)1,3,5-三嗪。
在冰冷的同时,将5.4g吗啉缓慢地加到由实施例15制备的6g产物中。然后另外加入30ml吗啉并将反应混合物加热至回流,在回流加热38小时后,冷却混合物并加入50ml水,过滤出在此期间析出的沉淀物,用水洗涤并干燥。产物由二氯甲烷/己烷重结晶,得到熔点为319-321℃(可同时分解)的白色粉末。
分析:计算值:C=56.54% H=22.93% N=7.43%
实验值:C=56.55% H=22.88% N=7.53%
实施例17:2,4-二氯-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在搅拌和冷至0-5°的同时,将300ml二甲苯中的55.3g(0.3mol)氰尿酰氯的溶液滴加到100ml二甲苯中的119.6g(0.6mol)4,4-亚乙氧基-2,2,6,6-四甲基哌啶的溶液中,接着将混合物加热至回流并在沸点下保持26小时。加入150ml二甲苯后,使混合物冷却,并过滤出沉淀物,在真空下蒸发滤液。残余物由300ml乙腈重结晶,得到的产物是熔点为169-172°的棕色粉末。
分析:计算值:C=48.43% H=16.41% N=5.81%
实验值:C=48.49% H=16.20% N=5.66%
实施例18:2-氯-4-二异丙基氨基-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在搅拌的同时将26.1g(258mmol)二异丙胺加到100ml甲苯中的由实施例17得到的产物29.9g(86mmol)的溶液中,将混合物加热到回流并在此温度下保持24小时。冷却后,加入21ml水的4.1g NaOH溶液。滤出固体产物和由25ml甲苯重结晶,得到熔点为179-184℃的淡黄色粉末。
分析:计算值:C=58.31% H=17.00% N=8.32%
实验值:C=58.34% H=16.97% N=8.42%
实施例19:2-辛氨基-4-二异丙基氨基-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
将由实施例18得到的15g(36.4mmol)的产物与36ml辛胺一起加热至120°,保持3小时。冷却后,加入40ml水和使用30ml二氯甲烷将混合物萃取三次,用水洗涤CH2Cl2溶液,经Na2SO4干燥和蒸发。油性残余物溶解在己烷/丙酮中,并用SiO2色谱柱提纯,其主馏分是粘性物。
分析:计算值:C=66.63% H=16.65% N=10.38%
实验值:C=66.76% H=16.48% N=10.30%
实施例20:2,4-二吗啉代-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在冰冷的同时,将40g吗啉加到由实施例17得到的40g产物中,在加入另外的100g吗啉后,在搅拌的同时,将混合物缓慢加热至130°并回流6小时。冷却至室温后,加入150ml水,过滤形成的沉淀物,用水洗涤,并由乙腈重结晶,得到的产物熔点为216-221°。
分析:计算值:C=58.91% H=18.74%
N=8.09%
实验值:C=58.93% H=18.88%
N=8.01%
实施例21:2,4-二吗啉代-6-(4-氧代-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
将由实施例20得到的29.6g产物,在搅拌下加到200ml1∶1的四氢呋喃和水的混合物中的1.26g的对甲苯磺酸溶液中,在添加另外的60ml四氢呋喃后,将混合物加热至50°,保持5小时。然后,再加入1.26g甲苯磺酸,并在50°下进一步搅拌14小时。冷却后,用50ml的二氯甲烷萃取混合物五次,用水洗涤合并的CH2Cl2溶液,经Na2SO4干燥和蒸发。残余物由80ml乙腈重结晶,得到熔点为188-192°的白色晶体。
分析:计算值:C=59.38% H=20.78% N=7.97%
实验值:C=59.58% H=20.57% N=7.93%
实施例22:2,4-二氯-6-(2,2,6,6-四甲?4-十二烷基氧基哌啶-1-基)-1,3,5-三嗪。
用等摩尔当量的4-十二烷基氧基-2,2,6,6-四甲基哌啶代替在实施例10中所述的4-己氧基-2,2,6,6-四甲基哌啶,且其它步骤完全与实施例10相同,得到浅黄色油状的上述化合物。
分析:计算值:C=60.88% H=8.94% N=11.83%
Cl=14.97%
实验值:C=61.14% H=8.69% N=11.62%
Cl=14.66%
实施例23:2,4-二氯-6-(2,2,6,6-四甲基-4-烯丙氧基哌啶-1-基)-1,3,5-三嗪。
用等摩尔当量的4-烯丙氧基-2,2,6,6-四甲基哌啶代替在实施例10中所述的4-己氧基-2,2,6,6-四甲基哌啶,且其它步骤完全与实施例10相同。得到由乙醇重结晶的上述化合物的晶体产物,熔点为53-55°。
实施例24:用二(2-乙己基)胺代替实施例11中的吗啉,且其它步骤与实施例11完全相同,得到2,4-双〔二(2-乙己基)氨基〕-6-(2,2,6,6-四甲基-4-己氧基哌啶-1-基)-1,3,5-三嗪浅黄色油状物。
分析:计算值:C=75.12% H=12.35% N=10.51%
实验值:C=75.36% H=12.08% N=10.54%
实施例25:用4-丁氨基-2,2,6,6-四甲基哌啶代替实施例11中的吗啉,且其它步骤与实施例11完全相同,得到可由乙腈重结晶的2,4-双〔N-(2,2,6,6-四甲基哌啶-4-基)-丁氨基〕-6-(2,2,6,6-四甲基-4-己氧基哌啶-1-基)-1,3,5-三嗪白色晶体,熔点:135-137℃。
实施例26:2-氯-4-二异丙氨基-6-(2,2,6,6-四甲基哌啶-4-己氧基哌啶-1-基)-1,3,5-三嗪。
用等摩尔当量的实施例10制备的化合物代替2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪和一摩尔当量的二异丙胺代替实施例3中的乙胺溶液,其它步骤完全与实施例3相同。得到无色油状的上述化合物。
分析:计算值:C=63.47% H=9.76% N=15.42%
Cl=7.80%
实验值:C=63.64% H=9.73% N=15.47%
Cl=7.80%
实施例27:N,N′-双〔4-二异丙氨基-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-三嗪-2-基〕六亚甲基二胺。
在100°下,将2.07g(17mmol)1,6-二氨己烷和4ml水中的1.36g(34mmol)氢氧化钠溶液加到40ml二甲苯中的14mg(34mmol)的实施例18的产物的溶液中。在蒸出水的同时,其内部温度升至135°。21小时后,加入0.1g 1,6-二氨己烷并使之在同样温度下进一步反应6小时。冷却混合物到70℃,加入溶于7.4ml水中的0.26g氢氧化钠。混合物搅拌30分钟,并分离出两相,有机相用水洗三次,经Na2SO4干燥和蒸发。其残余物溶于氯仿中,并用SiO2色谱柱提纯,在充分干燥后,可得到作为主馏份的上述产物,熔点为145-147°。
分析:计算值:C=63.71% H=9.53% N=19.38%
实验值:C=64.13% H=9.52% N=19.01%
实施例28:2,4-二氯-6-(1,3,8-三氮杂-2,4-二氧代-3-十二烷基-7,7,9,9-四甲基螺〔4,5〕癸-1-基)-1,3,5-三嗪。
用一摩尔当量的1,3,8-三氮杂-2,4-二氧代-3-十二烷基-7,7,9,9-四甲基螺〔4,5〕癸烷代替实施例15中所述的1,3,8-三氮杂-2,4-二氧代-3,7,7,9,9-五甲基螺〔4,5〕癸烷,其他步骤与实施例15相同。在制备出的产物溶于己烷/丙酮中并用SiO2色谱柱提纯后,得到熔点为109-115°的上述产物。
实施例29:2,4-二吗啉代-6-(1,3,8-三氮杂-2,4-二氧代-3-十二烷基-7,7,9,9-四甲基螺〔4,5〕癸-1-基)-1,3,5-三嗪。
用实施例28中所述的一摩尔当量的2,4-二氯-6-(1,3,8-三氮杂-2,4-二氧代-3-十二烷基-7,7,9,9-四甲基螺〔4,5〕癸-1-基)-1,3,5-三嗪代替实施例15中所述的2,4-二氯-6-(1,3,8-三氮杂-2,4-二氧代-3,7,7,9,9-五甲基螺〔4,5〕癸-1-基)-1,3,5-三嗪,其它步骤与实施例16相同。可得到上述产物,其熔点为185-188°。
分析:计算值:C=63.52% H=9.09% N=17.43%
实验值:C=63.39% H=9.20% N=17.38%
实施例30:2,4-双-N-丁基甲氨基-6-(1,3,8-三氮杂-2,4-二氧代-3-十二烷基-7,7,9,9-四甲基螺〔4,5〕癸-1-基)-1,3,5-三嗪。
其步骤与实施例29相同,只是用一摩尔当量的N-丁基甲氨基代替吗啉,得到熔点为93-96°的上述化合物。
分析:计算值:C=67.25% H=10.35% N=17.43%
实验值:C=67.05% H=10.26% N=17.55%
实施例31:2,4-双-N-丁基甲氨基-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在冰冷的同时,将24ml N-丁基甲胺添加到由实施例17制备的15g产物中,加入另外的50ml N-丁基甲胺后,在搅拌的同时将混合物缓慢加热到88°,并回流24小时。冷至室温后,加入150ml水和若干HCl直到pH为2。然后用二氯甲烷进行摇动萃取,有机相经Na2SO4干燥,蒸发和再干燥,此时得到浅黄色油状的上式产物。
分析:计算值:C=64.25% H=9.89% N=18.73%
实验值:C=64.58% H=10.17% N=18.51%
实施例32:2,4-双-二丁氨基-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
用一摩尔当量的二丁胺代替实施例31中所述的N-丁基甲胺,其他步骤与实施例31完全相同,最后将产物溶于甲苯/己烷中并在SiO2柱上进行色谱提纯,得到无色油状的上述产物。
分析:计算值:C=67.63% H=10.59% N=15.77%
实验值:C=61.27% H=10.37% N=15.45%
实施例33:2,4-双-N-丁基甲氨基-6-(4-氧代-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
用实施例31中所述的一摩尔当量的2,4-双-N-丁基甲氨基-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪代替实施例21中所述的2,4-二吗啉代-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,且其他步骤完全与实施例31相同。最后将产物溶于己烷/丙酮中,并用SiO2柱色谱提纯,可得到无色油状的上述产物。
分析:计算值:C=65.31% H=9.97% N=20.77%
实验值:C=65.11% H=9.86% N=20.53%
实施例34:2,4-二吗啉代-6-(4-羟基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
使用雷尼镍作为催化剂,在60°和压力100bar下,将5g 2,4-二吗啉代-6-(4-氧代-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(由实施例21得到的产物)在100ml的四氢呋喃中进行氢化,直到反应终止。过滤反应混合物,蒸发溶液,其残余物由20ml甲苯重结晶,得到熔点为202-204°的白色晶体的上述物质。
分析:计算值:C=59.09% H=8.43% N=20.67%
实验值:C=59.27% H=8.35% N=20.54%
实施例35:2-氯-4-(1-乙酰基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
将43.4g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例1的产物)溶于175ml甲苯中,此后加入42.1g粉状KOH、1g碳酸钾和3.4g硫酸氢四丁铵,然后滴加110ml甲苯溶液中的29.9g 1-乙酰基-2,2,6,6-四甲基-4-羟基哌啶,用冰浴保持内部的温度为10°。搅拌3.5小时后,加入100ml的水,经Na2SO4干燥并蒸发,由己烷重结晶后,得到白色粉末状的上述产物,其熔点为114-116°。
分析:计算值:C=61.11% H=8.47% N=15.49%
实验值:C=61.46% H=8.50% N=15.27%
实施例36:2-氯-4-(1-羟基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
一摩尔当量的1-羟基-2,2,6,6-四甲基-4-羟基哌啶代替实施例35中所述的1-乙酰基-2,2,6,6-四甲基-4-羟基哌啶,且其它步骤与实施例35相同,产物最后由乙腈重结晶,得到淡红粉末状的上述产物,其熔点为152-153°。
分析:计算值:C?9.35% H=8.30% N=16.48%
实验值:C=59.08% H=8.29% N=16.65%
实施例37:N,N′-双〔4-(1-乙酰基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-三嗪-2-基〕-六亚甲基二胺。
60ml二甲苯、2.1g 1,6-二氨基己烷和在5ml水中的1.8g氢氧化钠溶液添加到20g 2-氯-4-(1-乙酰基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(由实施例35得到的产物)。然后将混合物加热,用蒸馏法除去水。当温度保持恒定时,在回流下将混合物搅拌24小时。冷却后,加入若干氢氧化钠溶液,此后分出相层,有机相经Na2SO4干燥和蒸发,用氯仿/己烷重结晶后,将产物溶于氯仿/甲醇中,并用SiO2柱进行色谱提纯,得到白色粉末的上述产物,其熔点为201-202°。
分析:计算值:C=65.93% H=9.58% N=17.74%
实验值:C=65.78% H=9.73% N=17.67%
实施例38:2-吗啉代-4-(1-羟基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
在回流下,将5g 2-氯-4-(1-羟基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(由实施例36得到的产物)与50ml吗啉搅拌3小时。在冷至20°后,加入200ml水并过滤出沉淀物,用石油醚重结晶后,得到淡红色晶体的上述化合物,其熔点为153-157°。
分析:计算值:C=63.13% H=9.11% N=17.67%
实验值:C=62.94% H=9.27% N=17.42%
实施例39:2-(1-乙酰基-2,2,6,6-四甲基哌啶-4-氧基)-4-(1-羟基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
将4g 2-氯-4-(1-羟基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(由实施例36得到的产物)溶于30ml甲苯中,此后加入2.6g粉末KOH、1g碳酸钾和0.15g硫酸氢四丁基铵后,在搅拌的同时加入1.95g1-乙酰基-2,2,6,6-四甲基-4-羟基哌啶。将混合物加热到60°,保持17小时。冷却后,加入30ml水,分离相层,有机相经Na2SO4干燥和蒸发,用二氯甲烷/己烷重结晶后,将产物溶于己烷/乙酸中,并在SiO2柱上进行色谱提纯,得到上述产物,其熔点为175-176°。
分析:计算值:C=65.38% H=9.43% N=14.30%
实验值:C=65.42% H=9.45% N=14.04%
实施例40:2-氯-4-〔N-双(2,2,6,6-四甲基哌啶-4-基)-氨基〕-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪。
将溶于60ml甲苯中的29.5g双(2,2,6,6-四甲基哌啶-4-基)胺添加到溶于130ml甲苯中的28.9g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(由实施例1得到的产物)中,回流搅拌26小时后并使之冷却,加入5.6g粉状KOH和30ml水,分离相层,有机相经Na2SO4干燥和蒸发。用乙腈重结晶,得到白色粉末的上述产物,其熔点为240-242°。
分析:计算值:C=65.72% H=9.93% N=17.88%
实验值:C=65.69% H=9.89% N=17.69%
实施例41
N,N′-双{4-〔N-双(2,2,6,6-四甲基哌啶
-4-基)-氨基〕-6-(2,2,6,6-四甲基哌啶-
1-基)-三嗪-2-基}-六亚甲基二胺
用实施例40中描述的摩尔当量的产物代替实施例37中描述的2-氯-4-(1-乙酰基-2,2,6,6-四甲基哌啶-4-氧基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,另外,操作步骤与实施例37中描述的相同。得到上面产物,白色粉末,熔点216-218°。
分析:计算值:C=69.55% H=10.79% N=19.66%
实验值:C=69.43% H=10.67% N=19.44%
实施例42
下式的化合物
将溶于500ml二甲苯中的66g氰尿酰氯在0°加入悬浮于300ml二甲苯中的150g 2,2,4,4,14,14,16,16-八甲基-7,11,18,21-四氧杂-3,15-二氮杂三螺〔5,2,2,5,2,2〕二十一烷中。在回流下搅拌51小时后,使混合物稍微冷却,过滤,蒸发液相。在溶于丙酮/氯仿/二氧甲烷中以后用SiO2柱色谱法提纯,从甲苯中重结晶,得到上面结构的化合物,熔点277-278°。
分析:计算值:C=49.30% H=5.71% N=15.86%
实验值:C=49.16% H=5.68% N=15.70%
实施例43
用实施例42中描述的摩尔当量的四氯化合物代替实施例31中使用的2,4-二氯-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,另外,操作步骤与实施例31中给出的相同。从丙酮中重结晶后得到上面结构的化合物,熔点141-143°。
分析:计算值:C=64.72% H=9.75% N=18.48%
实验值:C=64.66% H=9.79% N=18.37%
实施例44
2-氯-4-吗啉代-6-(4,4-亚乙二氧基-2,2,
6,6-四甲基哌啶-1-基)-1,3,5-三嗪
将3.8g吗啉加入30g 2,4-二氯-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例17中得到的产物)的100ml甲苯的溶液中,15分钟后,加入1.7g NaOH的5ml水溶液。然后,将混合物加热到60°,45分钟后再加入3.8g吗啉和1.7g NaOH的5ml水溶液。再进行1.5小时后反应结束。冷却后加入200ml甲苯,分离各相。有机相用Na2SO4干燥,并蒸发。从乙腈中重结晶,得到上面结构的化合物,熔点154-156°(白色粉末)。
分析:计算值:C=54.33% H=7.09% N=17.60%
实验值:C=54.58% H=7.18% N=17.70%
实施例45
2-〔双-(2-羟乙基)-氨基〕-4-吗啉代-6-
(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1
1-基)-1,3,5-三嗪
将5.3g二乙醇胺和1g NaOH的3ml水溶液加入20g2-氯-4-吗啉代-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(由实施例44得到的产物)的50ml二甲苯溶液中。在回流下搅拌1.75小时后再加1g NaOH的3ml水溶液。14小时后加入7.9g二乙醇胺,然后,混合物在回流下再搅拌28小时。使混合物冷却,用水洗,分离出有机相。用Na2SO4干燥后,蒸发,从甲苯中重结晶两次,得到上面产物,白色粉末,熔点135-140°。
分析:计算值:C=56.63% H=8.21% N=18.01%
实验值:C=56.67% H=8.13% N=17.90%
实施例46
2-〔双-(2-羟乙基)-氨基〕-4-吗啉代-6-
(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-
1-基)-1,3,5-三嗪和琥珀酸二乙酯的缩聚物
将3.5ml琥珀酸二乙酯和0.4g原钛酸四丁酯(单体)加入9.8g 2-〔双-(2-羟乙基)-氨基〕-4-吗啉代-6-(4,4-亚乙二氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例45的产物)的50ml甲苯溶液中。混合物加热24小时,以便通过蒸馏很缓慢地除去甲苯。稍微冷却后通过漂白土过滤产物,蒸发。剩余物在80°进行真空干燥。得到聚合物树脂,分子量 Mn=966/ Mw=1409(凝胶渗透色谱法)
实施例47
2,4-二吗啉代-6-(4-丁基氨基-2,2,6,6
-四甲基哌啶-1-基)-1,3,5-三嗪
在6g丁基胺和0.25g对-甲苯磺酸存在下,用5%钯/炭作为催化剂,在温度40°和压力80巴,在120ml甲醇和60ml乙酸乙酯中,将12g 2,4-二吗啉代-6-(4-氧代-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例21的产物)进行加氢,直到反应结束。反应混合物过滤并蒸发。将剩余物溶于二氯甲烷中后用水洗。有机相用Na2SO4干燥并蒸发。剩余物溶于甲苯/丙酮,用SiO2柱色谱法提纯。几天后油状产物结晶,熔点82-87°。
分析:计算值:C=62.44% H=9.39% N=21.24%
实验值:C=62.88% H=9.39% N=20.45%
实施例48
下式的化合物
将8g 2,4-二吗啉代-6-(4-丁基氨基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例47的产物)的30ml丙酮溶液冷却到0℃,逐滴加入3.2g氰尿酰氯的40ml丙酮溶液中。加入0.8g NaOH的2ml水溶液后,混合物在0°搅拌3小时,然后,加入60ml水。过滤出沉淀的产物,从乙腈中重结晶。得到上面结构化合物的白色结晶,熔点198-203°。
分析:计算值:C=53.20% H=6.94% N=22.98%
实验值:C=53.32% H=6.93% N=22.92%
实施例49
下式的化合物
由实施例48得到的化合物和六亚甲基二胺的缩聚物
用摩尔当量实施例48中描述的二氯化物代替实施例14中描述的2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,另外,操作步骤与实施例14中描述的相同。得到可以粉化的聚合物,分子量 Mn=1520/ Mw=1985(凝胶渗透色谱法)。
实施例50
2,4-二吗啉代-6-(4-异丁烯酰氧基-2,2,6,
6-四甲基哌啶-1-基)-1,3,5-三嗪
10.2g 2,4-二吗啉代-6-(4-羟基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例34的产物)与6.9ml异丁烯酸乙酯,0.04g 2,6-二叔丁基-对-甲苯酚和0.04ml原钛酸四丁酯(单体)一起加热到120°,用蒸馏缓慢除去一些液体。使混合物反应50小时,随后按时加入一些异丁烯酸乙酯和催化剂。反应结束后,产物用漂白土过滤,蒸发。残余物溶于甲苯/丙酮中,用SiO2柱色谱法提纯,得到上面的产物,无色树脂。
分析:计算值:C=60.74% H=8.07% N=17.71%
实验值:C=60.60% H=8.10% N=17.10%
实施例51
2,4-二吗啉代-6-(4-异丁烯酰氧基-2,2,6,
6-四甲基哌啶-1-基)-1,3,5-三嗪的均聚物
6g 2,4-二吗啉代-6-(4-异丁烯酰氧基-2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例50的产物)和0.13g十二烷硫醇和0.1gα,α′-偶氮二异丁腈一起在氮气保护下在25ml异丙基甲基酮中加热到75°计12小时。混合物蒸发后,剩余物在60°真空干燥72小时,得到可以粉化的白色聚合物,分子量 Mn=3188/ Mw=12064(凝胶渗透色谱法)。
实施例52
N,N′-双〔1-(2,4-二吗啉代-1,3,5-三嗪
-6-基)-2,2,6,6-四甲基哌啶-4-基〕-六亚
甲基二胺
用摩尔当量的1,6-二氨基己烷代替实施例47中使用的丁基胺,另外,操作步骤与实施例47中给出的相同。得到上面的化合物,白色粉末,熔点198-202°。
分析:计算值:C= % H= % N= %
实验值:C= % H= % N= %
实施例53
2-氯-4,6-双-(2,2,6,6-四甲基哌啶-1
-基)-1,3,5-三嗪
18.4g氰尿酰氯和113g 2,2,6,6-四甲基哌啶在300ml高压釜中在180°加热10小时,然后,在210°加热10小时。高压釜的内容物溶于500ml水中,用吸滤过滤出不溶的残余物,用水洗,干燥。棕色残余物从石油醚中结晶。得到2-氯-4,6-双-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,无色结晶,熔点188°。
实施例54
2,4-二氯-6-〔2,2,6,6-四甲基-4-(N
-乙酰基-丁基氨基)哌啶-1-基)-1,3,5-三嗪
正如实施例1中所描述的那样,9.2g氰尿酰氯和26.7g2,2,6,6-四甲基-4-(N-乙酰基-丁基氨基)哌啶在100ml二甲苯中反应,并进行处理。得到2,4-二氯-〔2,2,6,6-四甲基-4-(N-乙酰基-丁基氨基)-哌啶-1-基)-1,3,5-三嗪,无色结晶,熔点131-133°。
实施例55
2-氯-4-异丙氧基-6-(2,2,6,6-四甲基哌啶
-1-基)-1,3,5-三嗪
正如实施例1中所描述的那样,104.0g 2,4-二氯-6-异丙氧基-1,3,5-三嗪和148.3g 2,2,6,6-四甲基哌啶在300ml二甲苯中反应,并进行处理。从己烷中结晶,得到2-氯-4-异丙氧基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,无色结晶,熔点111-112°。
实施例56
2,4-二异丙氧基-6-(2,2,6,6-四甲基哌啶
-1-基)-1,3,5-三嗪
首先,将12.5g 2-氯-4-异丙氧基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(实施例55的产物),11.2g精细粉碎的氢氧化钾和0.7g硫酸氢四丁基铵加入60ml甲苯中。在15分钟内将2.6g异丙醇逐滴加入这个橙色的悬浮液中,反应轻微放热使温度升至约30°。烧瓶中的浅棕色内容物在60 °搅拌8小时,冷却至0-5°,用80ml水稀释,然后用40ml甲苯稀释。把棕色水相和无色有机相分开,后者用水洗四次,每次用80ml水,用硫酸钠干燥,用真空完全蒸发。得到浅黄色油状物,过一会儿就固化,得到2,4-二异丙氧基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,熔点范围70-98°。
实施例57
2-异丙氧基-4-正-辛氧基-6-(2,2,6,6
-四甲基哌啶-1-基)-1,3,5-三嗪
用5.7g 1-辛醇代替实施例56中的异丙醇,另外,操作步骤与实施例56中描述的相同。得到2-异丙氧基-4-正辛氧基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,浅黄色树脂。
分析:计算值:13.78%N,实验值:13.87%N
实施例58
2-异丙氧基-4-二丁基氨基-6-(2,2,6,6
-四甲基哌啶-1-基)-1,3,5-三嗪
12.5g 2-氯-4-异丙氧基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪和5.5g二丁基胺溶于100ml二甲苯中。加入1.8g氢氧化钠的10ml水溶液后,在微量氮气流下,在水分离器中用蒸馏缓慢地除去水。其后,烧瓶中的内容物在135°搅拌16小时。使混合物稍微冷却,将50ml水加入烧瓶的内容物中,混合物激烈搅拌10分钟。分离出水相,有机层用水洗四次,每次用50ml水,用硫酸钠干燥,用真空完全蒸发。得到2-异丙氧基-4-二丁基氨基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,浅黄色树脂。
分析:计算值:17.27%N,实验值:17.29%
实施例59
下式的化合物
正如在实施例5 8中描述的那样,18.8g 2-氯-4-异丙氧基-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,3.6g 1,6-二氨基己烷和2.6g氢氧化钠的10ml水溶液在100ml二甲苯中进行反应。从二甲苯中结晶,得到上式的化合物,无色结晶,熔点224-226°。
实施例60
2,4-双(2-羟乙基氨基)-6-(2,2,6,6-四
甲基哌啶-1-基)-1,3,5-三嗪
用26.9g乙醇胺(第一部分:12.2g,第二部分:14.7g)代替二丁基胺,其他步骤与实施例6中描述的相同。从甲苯中结晶后,得到2,4-双-(2-羟乙基氨基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪,熔点147-148°。
实施例61
下式的聚合物
正如在实施例6中所描述的那样,在200ml二甲苯中含有6.8g氢氧化钠的溶液存在下,23.1g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪和31.4g 1,6-双(2,2,6,6-四甲基-4-哌啶基氨基)-己烷进行反应。得到微黄色树脂,分子量1330。
实施例62
首先,将57.8g 2,4-二氯-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪加入200ml二甲苯中。在15分钟内逐滴加入17.4g N-甲基丁基胺。温度升至50°。8.8g氢氧化钠的30ml水溶液在10分钟内逐滴加入反应混合物中。混合物在60°搅拌2小时。然后,分离出水相,加入41.4g1,6-双(2,2,6,6-四甲基-4-哌啶基氨基)-己烷,混合物加热到90°,加入9.6g氢氧化钠的30ml水溶液。在微量氮气流下在水分离器中用蒸馏缓慢地除去水,烧瓶中的内容物在135°搅拌18小时。稍微冷却后,将100ml水加入反应混合物中,激烈搅拌10分钟。分离出水相,有机溶液用水洗三次,每次用50ml水,用硫酸钠干燥,真空蒸发。从甲乙酮中结晶剩余物,得到上式的化合物,熔点137-138°。
实施例63
正如实施例62中描述的那样,28.9g 2,4-二氯-6-(2,2,6,6-(四甲基哌啶-1-基)-1,3,5-三嗪和12.9g二丁基胺反应,然后与1.6g二氨基己烷反应。从乙腈中结晶后,得到上式的化合物,熔点93-94°。
实施例64
下式的化合物
在微量氮气流下,在150ml二甲苯中加入0.2g氨基化锂后,19.0g 2,4-二丁基氨基-6-(2,2,6,6-四甲基-4-羟基哌啶-1-基)-1,3,5-三嗪(根据实施例9制备的)和5.8g癸二酸二甲酯一起加热至回流计12小时,用蒸馏除去生成的甲醇。反应混合物冷却至约100°,加入5g TonsilOptimum(漂白土),混合物搅拌5分钟,过滤。蒸出溶剂,得到上式的化合物,微黄色树脂。
分析:计算值:18.20%N,实验值:18.51%N
实施例65
下式的化合物
用3.6g琥珀酸二甲酯代替癸二酸二甲酯,操作步骤与实施例64中描述的相同。从乙腈中结晶后,得到上式的化合物,无色结晶,熔点131°。
实施例66
下式的化合物
用4.8g对苯二甲酸二甲酯代替癸二酸二甲酯,操作步骤与实施例64中描述的相同。从二甲苯中结晶后,得到上式的化合物,无色结晶,熔点181°。
实施例67
2,4-二丁基氨基-6-{2,2,6,6-四甲基-4-
〔2-(3,5-二叔丁基-4-羟基苯基)-丙酰氧基〕
-哌啶-1-基}-1,3,5-三嗪
用14.6g 2-(3,5-二叔丁基-4-基苯基)丙酸甲酯代替癸二酸二甲酯,操作步骤与实施例6 4中描述的相同。得到2,4-二丁基氨基-6-(2,2,6,6-四甲基-4-〔2-(3,5-二叔丁基-4-羟基苯基)-丙酸氧基〕-哌啶-1-基}-1,3,5-三嗪,浅黄色树脂。
分析:计算值:13.51%N,实验值:13.56%N
实施例68
在微量氮气流下,在100ml二甲苯中,加入0.2g氨基锂后,16.9g 2,4-二(2-羟乙基氨基)-6-(2,2,6,6-四甲基哌啶-1-基)-1,3,5-三嗪(根据实施例26制备的)和29.2g β-(3,5-二叔丁基-4-羟基苯基)-丙酸甲酯一起加热至回流计12小时,用蒸馏除去生成的甲醇。反应混合物冷却到约100°,加入5g Tonsil Optimum(漂白土),混合物搅拌5分钟,过滤。除出溶剂后得到上式的化合物,黄色树脂。
分析:计算值:9.78% N,实验值:9.67% N
实施例69
下式的化合物
用25.0gβ-(3-甲基-4-羟基-5-叔丁基苯基)丙酸甲酯代替β-(3,5-二叔丁基-4-羟基苯基)丙酸甲酯,操作步骤与实施例6 8中描述的相同。得到上式的化合物,可以粉碎的黄色树脂。
分析:计算值:10.84%N,实验值10.57%N
实施例70
2-氯-4-〔N-(2,2,6,6-四甲基-4-哌啶基)
-正丁基氨基〕-6-(2,2,6,6-四甲基-4-己氧基
哌啶-1-基)-1,3,5-三嗪
由实施例10得到的二氯衍生物与1当量4-丁基氨基-2,2,6,6-四甲基哌啶反应,这时的操作步骤与实施例26中描述的相同。得到标题化合物,无色油状物。
分析:计算值:14.87%N,实验值:14.74%N
实施例71
N,N′,N″-三{2-(2,2,6,6-四甲基-4
-己氧基哌啶-1-基)-4-〔N-(2,2,6,6-
四甲基哌啶-4-基)-丁基氨基〕-1,3,5-三嗪-
6-基}二亚乙基三胺
将溶于3ml水中的0.71ml二乙基三胺和0.9g NaOH加入溶于50ml甲苯中的由实施例70得到的10.6g-氯衍生物。加热到100°后开始蒸出溶剂。加入50ml甲苯,1g聚乙二醇1000和0.9g NaOH,混合物在搅拌下回流加热14小时。冷却后,反应混合物用100ml乙酸乙酯稀释,该溶液用水洗四次。有机溶液用Na2SO4干燥,蒸发。剩余物溶于50ml甲醇中,用200g硅胶过滤,用500ml甲醇洗。蒸发甲醇溶液,剩余物是接近无色的树脂。
分析:计算值:17.4%N,实验值:17.4%N
实施例72
涂二道清漆的稳定剂
通过混合下列组分制备透明清漆:
58.3份丙烯酸树酯(Viacryl_VC373,Vianova AG)
27.3份密胺树脂(Maprenal_MF590,Hoechst AG)
4.0份芳香溶剂混合物(Solvesso_150)
5.4份二甲苯
4.0份丁基乙二醇乙酸酯
1.0份进料控制助剂(Baysilon_A,Bayer AG)
表1所示的光稳定剂加入该清漆中。用乙酸丁酯和二甲苯的1∶1的混合物稀释清漆,直至可喷涂,喷漆在涂有金属银基层的铝片上。然后,试样在130℃硬化30分钟。得到透明清漆层厚度40-45μm。
这样制备的试样在UVCON_曝光设备(Atlas Corp.)中进行老化试验,该设备的一个工作周期在70℃有8小时UV照射,在50℃有4小时雾化。
各种情况下400小时老化后,根据DIN67530测定试样20°光泽。结果列于表1中。
表1
老化后的20°光泽光稳定剂1) 0 400 800 1200小时无 85 83 192)1%实施例5的化合物 86 84 67 282)1%实施例6的化合物 87 85 75 431%实施例7的化合物 88 86 74 401%实施例13的化合物 86 85 78 311%实施例24的化合物 87 86 80 35
1)相对于清漆固体含量的数据
2)形成裂纹
实施例73
涂二道漆清漆的露天空气老化
正如实施例70中描述的那样,制备涂二道漆的试样。试样在佛罗里达中暴露在空气中老化54个月。根据DIN67530每12个月测定20°光泽。结果列于表2中。
表2
空气老化后20°光泽光稳定剂1) 月 数
0 12 24 36 48 54无 93 70 49 362) 16 -1%实施例4的化合物 94 73 76 69 57 532)1%实施例5的化合物 95 72 73 69 64 67
1)相对于清漆固体含量的数据
2)形成裂纹
实施例74
将0.087g下式的黄色成色剂
溶于2.0ml表3所示的稳定剂的乙酸乙酯溶液(2.25g/100ml)中。9.0ml pH调至6.5并含有1.744g/L下式的湿润剂的2.3%明胶水溶液加入1.0ml上述溶液中。
银含量6.0g/l的2ml溴化银乳剂和1.0ml 0.7%下式的硬化剂的水溶液加入5.0ml这样得到的成色剂乳剂中,将其倒在13×18cm涂塑料的纸上。硬化7天后,试样暴露在银梯级光楔后的125勒克司中,接着用Kodak Ektaprint方法处理。
得到的黄色光楔在Atlas Weather Ometer中用在UV滤光器(Kodak 2C)后面的2500W氙灯以60千焦尔/cm2的总能量照射。
没有稳定剂的试样作为标准试样同时进行处理。
下面表3给出了在以黄色染料最大吸收的照射期间出现的彩色密度损失,用Macbeth TR924A密度计测定。
从彩色密度损失看出光稳定剂的作用是明显的。密度损失越少,光稳定剂的效果就越高。
表3
稳定剂 | 彩色密度损失(%) |
无 | 35 |
实施例68的产物 | 18 |
实施例69的产物 | 14 |
实施例75
9.0ml pH调至6.5并含有0.872g/L湿润剂二丁基萘磺酸钠的2.3%明胶水溶液加入1.0ml上述溶液中。
然后,正如实施例72中所描述的那样,用有乳剂的方法,但是不同的是溴化银乳剂中银含量为3g/L。
得到的彩色梯级光楔在Atlas Weather Ometer中用在UV滤光器(Kodak)后面的2500W的氙灯以60千焦尔/cm2的总能量照射,然后,正如在实施例72中所描述的那样,测定彩色密度损失。
结果总结于下面的表4中。
稳定剂 | 彩色密度损失(%) |
无 | 43 |
实施例68的化合物 | 22 |
实施例69的化合物 | 23 |
Claims (16)
1.包括至少一个化合物作为稳定剂的有机材料,上述化合物至少含有一个式I的基团,其中X是完成其环使之形成哌啶环的基。
2.根据权利要求1的有机材料,其包括至少一个式II化合物,其中n是1至6的整数,R1是下式基或是Cl、OH、-OR3、-SR3或-NR4R5,其中R3是C1-C18烷基、烯丙基、环己基、苄基、苯基或式A基,R4是氢、C1-C12烷基、2-羟乙基、烯丙基、环己基、苄基或式A基,R5是C1-C12烷基、2-羟乙基、烯丙基、环己基、苄基、苯基、被卤素、C1-C4烷基或C1-C4烷氧基取代的苯基、式A基或式C基其中D是由 断开的C2-C10亚烷基,Ra和Rb是C1-C12烷基、C5-C6环烷基、C6-C10芳基或C7-C9苯烷基,且Ra也可是氢,或R4和R5在一起是由-O-或-N(R8)-断开的C4-C8亚烷基,其中R8是氢、C1-C4烷基或乙酰基,R6是氢、C1-C12烷基、C7-C9苯烷基、C3-C5链烯基、C2-C4烷酰基、C3-C5烯酰基、-O、-OH或-OR7,且R7是C1-C18烷基、C5-C8环烷基、C7-C9苯烷基、苯基、C2-C18烷酰基或苯甲酰基,如果n=1,R2是Cl、OH、-OR3、-SR3或-NR4R5,如果n=2,R2是-O-R9-O-、-S-R9-S-、-N(R10)-R93、-SR-O-R9-N(R10)-, 或-NH-NH-,其中R9是可被一个或多个-O-、-N(R8)-或-OOC-R17-COO-断开的C2-C20亚烷基、C4-C8亚烷基、C5-C8亚环烷基、亚二甲苯基、亚苯基或亚甲代苯基,R10是氢、C1-C12烷基、烯丙基、2-羟乙基、苄基、苯基或式A基,如果n=3,R2是下式基:或
其中a是2或3,Q是-O-、-S-或-N(R10)-,和T是C3
-C20烷烃三基或下式基:或 其中Alk是C2-C12亚烷基,如果n=4,R2是C(CH2O)4或其中a是2或3和b是2-12,如果n=5,R2是如果n是6,R2是y是下面的基:其中:m是0、1或2,q是5-11的整数,R11是氢、C1-C16烷基、C3-C7链烯基、C5-C8环烷基、C7-C11芳烷基或-CO-R18基,R12是氢、C1-C12烷基、C3-C7链烯基、C5-C8环烷基、C7-C11芳烷基、C2-C4羟烷基、C3-C6烷氧基烷基、C4-C20二烷基氨基烷基、C3-C14烷氧基羰基烷基或式A基,R13是C1-C12烷基、C2-C4羟烷基、C3--C7链烯基、C5-C8环烷基、苯基、被卤素、C1-C4烷基或C1-C4烷氧基取代的苯基、C2-C20烷酰基、C3-C8烯酰基、苯甲酰基、苯乙酰基或式B的三嗪基或R12和R13在一起是可由-O-或-N(R8)-断开的C4-C9亚烷基,或R12和R13在一起是下式基其中:R21是C1-C18烷基,R14是C1-C18烷基、C5-C8环烷基或C7-C9苯烷基,或二个R14基在一起是C2-C6亚烷基、邻亚苯基或邻亚二甲苯基,R15是氢、C1-C12烷基、C3-C5链烯基、C7-C9苯烷基、C2-C4羟烷基、C3-C8烷氧基烷基或C3-C14烷氧基羰基烷基,R16是氢、C1-C12烷基、烯丙基或苄基,R17是C1-C12亚烷基、亚乙烯基、亚环己基、亚二甲苯基或C6-C12亚芳基,R18是C1-C18烷基、C2-C6链烯基、C5-C8环烷基、C7-C9苯烷基、苯基或被卤素、硝基、C1-C4烷基、羟基或C1-C4烷氧基取代的苯基,或被羟基和C1-C4烷基取代的C7-C9苯烷基,R19定义同R1,和R20是Cl、-OH、-OR3、-SR3或-NR4R5。
3。根据权利要求1的有机材料,其含有至少一个式III化合物其中P是2、3或4,R19和R20如同权利要求2中定义,如果P是2。Z是如下基团之一:其中:R22是C2-C12亚烷基、C4-C8亚烯基、亚二甲苯基、或-CO-,R23是C1-C12亚烷基、亚乙烯基、环己烯基、亚二甲苯基、C6-C12亚芳基或被卤素、硝基或C1-C4烷基取代的或直接键合的亚苯基,R24是氢、C1-C12烷基、C5-C8环烷基、C7-C9苯烷基、C3-C7链烯基、C2-C18烷酰基、C3-C7烯酰基或苯甲酰基,R25是C2-C12亚烷基、由NH或O断开的C4-C16亚烷基、C4-C8亚烯基、亚二甲苯基或环己烯基,R26是氢、C1-C12烷基、C5-C8环烷基或式A基,R27定义同R23或是-NH-R28-NH-基,R28是C2-C12亚烷基或可被C1-C4烷基取代的C6-C12亚芳基,R20是氢、C1-C12烷基、C2-C18烷酰基或式B的三嗪基,R1、A和B如同权利要求2中定义,如果P是3,Z是下述基团之一:其中R30是C3-C18烷烃三基或C6-C12芳烃三基,如果P是4,Z是下述基团之一:或
其中R31是C4-C16烷烃四基或C6-C12芳烃四基。
5.根据权利要求1的有机材料,其包括至少一个式V化合物,其中r具有3至50的数值,y和R1如同权利要求2中的定义,An是C2-C4亚烷基,R23如同权利要求3中的定义。
7.根据权利要求1的有机材料,其包括至少一个式VII化合物,其中S是0或1,t是0或2,u具有5至100的数值,Q″是-O-、-NH-或-N(C1-C4烷基)-,R34是氢或甲基,相互无关的R35和R36是-OR3、-SR3或-NR4R5,其中R3、R4和R5如同权利要求2中的定义,和这种化合物与(甲基)丙烯酸、烷基(甲基)丙烯酸酯、羟烷基(甲基)丙烯酸酯或马来酐的共聚物。
8.根据权利要求1的有机材料,其包括至少一个式VIII化合物,其中r具有3至50的数值,t是0或2,Q和Q′如同权利要求4中的定义, Q″是-O-,-NH-或-N(C1-C4烷基)-,R35和R36如同权利要求7中的定义。
11.根据权利要求1的有机材料,其包括至少一个式XI化合物,其中n是1至6的整数,t是0或2,R2如同权利要求2中的定义,Q″、R35和R36如同权利要求7中的定义,R40或者如同R1的定义或者是下式基
13.根据权利要求1的有机材料,其是有机聚合物。
14.根据权利要求1的有机材料,其是油漆。
15.根据权利要求1的有机材料,其是感光层。
16.根据权利要求15的感光层,其还包括位阻酚。
Applications Claiming Priority (2)
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CH44088 | 1988-02-08 | ||
CH440/88-1 | 1988-02-08 |
Publications (1)
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CN1036760A true CN1036760A (zh) | 1989-11-01 |
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CN89101832A Pending CN1036760A (zh) | 1988-02-08 | 1989-02-07 | 四甲基哌啶子基-s-三嗪类化合物 |
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Country | Link |
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US (1) | US5059689A (zh) |
EP (1) | EP0328024B1 (zh) |
JP (1) | JP2782449B2 (zh) |
KR (1) | KR890012997A (zh) |
CN (1) | CN1036760A (zh) |
AT (1) | ATE116311T1 (zh) |
AU (1) | AU621082B2 (zh) |
BR (1) | BR8900532A (zh) |
CA (1) | CA1339783C (zh) |
DD (1) | DD283411A5 (zh) |
DE (1) | DE58908808D1 (zh) |
ZA (1) | ZA89928B (zh) |
Cited By (2)
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CN101394831B (zh) * | 2005-12-15 | 2012-11-14 | 卢塞迪奥·格莱西 | 氮氧化物抗氧化剂的合成和在化妆用和皮肤病用组合物中的使用方法 |
CN107709522A (zh) * | 2015-08-07 | 2018-02-16 | Dic株式会社 | 液晶组合物和使用其的液晶显示元件 |
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ES2058309T3 (es) * | 1987-10-30 | 1994-11-01 | Sankyo Co | Derivados de piperidiltriazina y su utilizacion como agentes estabilizadores para polimeros. |
GB9024617D0 (en) * | 1989-12-05 | 1991-01-02 | Ici Plc | Heterocyclic compounds |
US5238980A (en) * | 1992-10-13 | 1993-08-24 | Phillips Petroleum Company | Corrosion inhibition of stereoregular, branched-mono-1-olefin polymers |
IT1264945B1 (it) * | 1993-07-16 | 1996-10-17 | Ciba Geigy Spa | Composti piperidinici atti all'impiego come stabilizzanti per materiali organici |
US5730906A (en) * | 1996-07-12 | 1998-03-24 | Exxon Research And Engineering Company | Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406) |
WO2002060882A2 (en) * | 2001-01-31 | 2002-08-08 | Roche Vitamins Ag | Process for the preparation of 2-(disubstituted-amino)-4,6-diaryl triazines |
JP2011256367A (ja) * | 2010-05-10 | 2011-12-22 | Natoko Kk | オリゴマー被覆金属酸化物微粒子 |
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NL277028A (zh) * | 1961-04-19 | |||
BR6915234D0 (pt) * | 1969-05-22 | 1973-06-07 | American Cyanamid Co | Novos derivados de melamina e processo para sua preparaca |
US3576805A (en) * | 1969-05-22 | 1971-04-27 | American Cyanamid Co | N**2,n**4,n**6-trisubstituted melamines |
GB1393551A (en) * | 1972-04-21 | 1975-05-07 | Ciba Geigy Ag | Piperidine derivatives |
CH582231A5 (zh) * | 1973-12-10 | 1976-11-30 | Sandoz Ag | |
IT1052501B (it) * | 1975-12-04 | 1981-07-20 | Chimosa Chimica Organica Spa | Composti politriazinici utilizzabili per la stabilizzazione di polimeri sintetici e procedimento per la loro preparazione |
IT1060458B (it) * | 1975-12-18 | 1982-08-20 | Chimosa Chimica Organica Spa | Composti piperidil triazinici adatti per la stabilizzazione di polimeri sintetici e procedimento per la loro preparazione |
DE3208570A1 (de) * | 1981-03-20 | 1982-09-30 | Sandoz-Patent-GmbH, 7850 Lörrach | N-ss-aminoaethylpiperidin-verbindungen |
CH653019A5 (de) * | 1981-03-20 | 1985-12-13 | Sandoz Ag | N-beta-aminoaethylpiperidinverbindungen. |
EP0080431B1 (de) * | 1981-10-16 | 1986-09-24 | Ciba-Geigy Ag | Synergistisches Gemisch von niedermolekularen und hochmolekularen Polyalkylpiperidinen |
US4722806A (en) * | 1982-02-19 | 1988-02-02 | The B. F. Goodrich Company | Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines and UV light stabilized compositions |
IT1169843B (it) * | 1983-09-23 | 1987-06-03 | Chimosa Chimica Organica Spa | Composti polimerici contenenti radicali piperidinici, processo per la loro preparazione e loro impiego quali stabilizzanti per polimeri sintetici |
DE3581002D1 (de) * | 1984-06-22 | 1991-02-07 | Ilford Ag | Hydroxyphenyltriazine, verfahren zu ihrer herstellung und ihre verwendung als uv-absorber. |
JPS624733A (ja) * | 1985-07-02 | 1987-01-10 | Mitsubishi Petrochem Co Ltd | 無機フイラ−含有ポリオレフイン組成物 |
DE3524543A1 (de) * | 1985-07-10 | 1987-01-22 | Hoechst Ag | Verfahren zur herstellung von 1-oxa-3,8-diaza-4-oxo-spiro-(4,5)decan- verbindungen |
DE3524542A1 (de) * | 1985-07-10 | 1987-01-22 | Hoechst Ag | 1-oxa-3-oxo-4,8-diaza-spiro-(4,5)decan- verbindungen |
US4629752A (en) * | 1985-07-22 | 1986-12-16 | The B. F. Goodrich Company | Substituted oxo-piperazinyl-triazines and UV light stabilized compositions |
JPH0625109B2 (ja) * | 1985-09-04 | 1994-04-06 | 旭電化工業株式会社 | 四級アンモニウム塩化合物 |
CA1290884C (en) * | 1985-10-17 | 1991-10-15 | Kunio Yamada | Polyolefin composition |
IT1197466B (it) * | 1986-08-25 | 1988-11-30 | Ciba Geigy Spa | Metodo per la stabilizzazione di polimeri oleofinici mediante composti triazinici |
-
1989
- 1989-01-25 AU AU28774/89A patent/AU621082B2/en not_active Ceased
- 1989-01-30 US US07/303,217 patent/US5059689A/en not_active Expired - Fee Related
- 1989-02-03 BR BR898900532A patent/BR8900532A/pt unknown
- 1989-02-06 DE DE58908808T patent/DE58908808D1/de not_active Expired - Fee Related
- 1989-02-06 EP EP89102019A patent/EP0328024B1/de not_active Expired - Lifetime
- 1989-02-06 DD DD89325550A patent/DD283411A5/de not_active IP Right Cessation
- 1989-02-06 CA CA000590189A patent/CA1339783C/en not_active Expired - Fee Related
- 1989-02-06 AT AT89102019T patent/ATE116311T1/de not_active IP Right Cessation
- 1989-02-07 CN CN89101832A patent/CN1036760A/zh active Pending
- 1989-02-07 ZA ZA89928A patent/ZA89928B/xx unknown
- 1989-02-08 KR KR1019890001409A patent/KR890012997A/ko not_active Application Discontinuation
- 1989-02-08 JP JP1029589A patent/JP2782449B2/ja not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101394831B (zh) * | 2005-12-15 | 2012-11-14 | 卢塞迪奥·格莱西 | 氮氧化物抗氧化剂的合成和在化妆用和皮肤病用组合物中的使用方法 |
CN107709522A (zh) * | 2015-08-07 | 2018-02-16 | Dic株式会社 | 液晶组合物和使用其的液晶显示元件 |
Also Published As
Publication number | Publication date |
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BR8900532A (pt) | 1989-10-03 |
ATE116311T1 (de) | 1995-01-15 |
ZA89928B (en) | 1989-10-25 |
CA1339783C (en) | 1998-03-31 |
EP0328024A1 (de) | 1989-08-16 |
DE58908808D1 (de) | 1995-02-09 |
DD283411A5 (de) | 1990-10-10 |
KR890012997A (ko) | 1989-09-20 |
US5059689A (en) | 1991-10-22 |
EP0328024B1 (de) | 1994-12-28 |
AU621082B2 (en) | 1992-03-05 |
JP2782449B2 (ja) | 1998-07-30 |
AU2877489A (en) | 1989-09-14 |
JPH01294672A (ja) | 1989-11-28 |
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