CN1130625A - 2-羟基苯基三嗪 - Google Patents
2-羟基苯基三嗪 Download PDFInfo
- Publication number
- CN1130625A CN1130625A CN95117220A CN95117220A CN1130625A CN 1130625 A CN1130625 A CN 1130625A CN 95117220 A CN95117220 A CN 95117220A CN 95117220 A CN95117220 A CN 95117220A CN 1130625 A CN1130625 A CN 1130625A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- phenyl
- alkenyl
- independently
- another
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 239000011368 organic material Substances 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 259
- -1 1-adamantyl Chemical group 0.000 claims description 166
- 229910052799 carbon Inorganic materials 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 68
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 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 44
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 39
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 31
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 24
- 125000005466 alkylenyl group Chemical group 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000007334 copolymerization reaction Methods 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 8
- 229910052728 basic metal Inorganic materials 0.000 claims description 8
- 150000003818 basic metals Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 7
- 239000012964 benzotriazole Substances 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 229920000620 organic polymer Polymers 0.000 claims description 5
- 238000012644 addition polymerization Methods 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229920001577 copolymer Polymers 0.000 abstract description 17
- 229920001519 homopolymer Polymers 0.000 abstract description 13
- 239000006096 absorbing agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 134
- 239000000203 mixture Substances 0.000 description 113
- 229910052757 nitrogen Inorganic materials 0.000 description 85
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 49
- 239000000126 substance Substances 0.000 description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- 239000000460 chlorine Substances 0.000 description 45
- 239000007787 solid Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 38
- 239000000243 solution Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 238000001914 filtration Methods 0.000 description 23
- 238000005259 measurement Methods 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 18
- 229960003742 phenol Drugs 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 13
- 238000012986 modification Methods 0.000 description 13
- 230000004048 modification Effects 0.000 description 13
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 12
- 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 11
- 238000010521 absorption reaction Methods 0.000 description 11
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 11
- NPSSWQJHYLDCNV-UHFFFAOYSA-N prop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=C NPSSWQJHYLDCNV-UHFFFAOYSA-N 0.000 description 11
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 10
- 238000013019 agitation Methods 0.000 description 10
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 8
- 239000004926 polymethyl methacrylate Substances 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 5
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 5
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 150000002429 hydrazines Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 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 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- 239000004925 Acrylic resin Substances 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- SHESFHIAOWKQPJ-UHFFFAOYSA-N C1=NC=NC=N1.C1=CC=CC=C1C1=CC=CC=C1 Chemical class C1=NC=NC=N1.C1=CC=CC=C1C1=CC=CC=C1 SHESFHIAOWKQPJ-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 229940051250 hexylene glycol Drugs 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 229920000092 linear low density polyethylene Polymers 0.000 description 4
- 239000004707 linear low-density polyethylene Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- GXFQBBOZTNQHMW-UHFFFAOYSA-N n'-(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound CC1(C)CC(NCCCCCCN)CC(C)(C)N1 GXFQBBOZTNQHMW-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
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- BYYFPVDBAHOLDX-UHFFFAOYSA-N n-dodecyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCCCCC)C1=CC=CC=C1 BYYFPVDBAHOLDX-UHFFFAOYSA-N 0.000 description 1
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- HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
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- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000012994 photoredox catalyst Substances 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
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- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 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
- 239000001294 propane Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- 235000010234 sodium benzoate Nutrition 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
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- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- BDIOXGVXNCWLPL-UHFFFAOYSA-N thiolane;thiolane 1,1-dioxide Chemical compound C1CCSC1.O=S1(=O)CCCC1 BDIOXGVXNCWLPL-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- 239000012745 toughening agent Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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- 235000004835 α-tocopherol Nutrition 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
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Classifications
-
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Abstract
本发明涉及新的2-羟基苯基三嗪及可由其制备的均聚合物和共聚合物,详细描述见说明书;此新化合物可作为有机材料中的UV吸收剂。
Description
本发明涉及新的2-羟基苯基三嗪,其制备方法,及其在有机材料中作为UV吸收剂的用途。
EP-A-043608公开了羟基苯基三嗪类UV吸收剂,特别是与具空间位阻的胺的合剂。此类化合物还见于US-A-5189084,EP-A-0530135,US-A-5364749和US-A-5300414。
羟基苯基三嗪类也可作为如表面涂料的UV吸收剂。US-3423360中描述了聚羟基苯基三嗪丙烯酸酯及甲基丙烯酸酯及其在表面涂料中的用途。
但是,已知的UV吸收剂常有不良的性质,如对光,热及潮湿的固有稳定性不够,迁移或挥发,乳化抗性,成晶或成块。
现发现一组2-羟基苯基三嗪UV吸收剂能很大程度上惊人地满足工业要求。
新的2-羟基苯基三嗪与其他类型的UV吸收剂的合剂,如与苯酮,苯并***,具空间位阻的胺类,N,N’-苯酰二苯胺,氰基丙烯酸酯,水杨酸酯,丙烯腈或噻唑啉的合剂,也适于稳定有机材料。
本申请即涉及通式I的2-羟基苯基三嗪 其中A为-C(=O)-CR5=CH-R6;R1为-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2或-C(=O)-O-CH2-C(=CH2)-R10;及当R3为-O-R8R8’-(CH2)L-XA时,R1还可为C1-C18的烷基或中间有-O-,-CO-O-或-O-CO-的C3-C20的烷基;及当E1为通式Ia,其中R2和R14都不是氢时,R1还可为-A,-CH2-CH(XA)-CH2O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-XA,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA及-CR8R8’-(CH2)L-C(C=O)-XA;及当E1为式Ib基团时,R1还可为-CH2-CH(XA)-CH2-O-R7;
R2彼此独立为H,C1-C12烷基,环己基,C3-C6链烯基,卤素,苯基或三氟甲基;
R2’彼此独立为C1-C18烷氧基,C3-C18链烯氧基,-OH或-O-CO-R12;
R3和R3’彼此独立为H,-OH,-O-CH2-CH(XA)-CH2-O-R7,,-O-CH2-C(=CH2)-R10,-O-(CH2)p-SiR11R11’-CH=CH2,-O-C(=O)-(CH2)q-CH=CH2,-O-C(=O)-O-CH2-C(=CH2)-R10,-O-CR8R8’-(CH2)1-XA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,-O-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,
-O-CR8R8’-(CH2)L-C(C=O)-XA,C1-C18烷基,C6-C12环烷基,C3-C18链烯基,-OR131,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C18烷基,C3-C6链烯基,-OR131,卤素,三氟甲基,苯基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基;C5-C12环烷基;C3-C18链烯基;苯基;取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;苯基-C1-C4-烷基;中间有1个或多个-O-的C3-C50烷基;1-金刚烷基;2-金刚烷基;降冰片基;2-甲基降冰片基或-C(=O)-R12;
R8和R8’彼此独立为H,C1-C18烷基,苯基,苯基-C1-C8-烷基,或取代有1-3个C1-C4烷基,C3-C8链烯氧基,C1-C8烷氧基,卤素或CF3的苯基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为H,C1-C18烷基,C2-C18链烯基,苯基,苯基-C1-C4烷基,C5-C12环烷基,C1-C12烷氧基,苯氧基,降冰片-2-基,5-降冰片烯-2-基或1-金刚烷基;
R13为C1-C18烷基,C3-C18链烯基,苯基,C5-C12环烷基,中间有1个或多个-O-的C3-C50烷基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基,1-金刚烷基,2-金刚烷基,降冰片基,2-甲基降冰片基;
R14和R15,彼此独立为H,C1-C18烷基,C3-C18链烯基,C6-C12环烷基,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-,苯基-S(=O)t-或OR131;
R131为C1-C18烷基,C3-C18链烯基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,C3-C6链烯氧基,卤素,-COOR13,-CONH2,-CONHR132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,苯氧基和/或C1-C18烷基,C1-C18烷氧基或卤素取代的苯氧基的C1-C18烷基;或C3-C18链烯基;C6-C12环烷基;C1-C4烷基和/或-OCOR12取代的C6-C12环烷基;中间有一个或多个-O-无取代或取代有OH或O-CO-R12的C3-C50烷基;苯在;苯基-C1-C4烷基;-COR12或-SO2R12;
R132和R133彼此独立为C1-C12烷基,C3-C12烷氧基烷基,C4-C16二烷基氨基烷基或C5-C12环烷基;或
R132和R133一起为C3-C9亚烷基,C3-C9氧杂亚烷基或氮杂亚烷基;
X为-NR8-,-O-,-NH-(CnH2n)-NH-或-O-(CKH2K)-NH-;
k为2至4;
l为0至19;
m为2至8;
n为0至4;
p为0至10;
q为1至8;
r为0至18;
t为0,1或2。
通式I的化合物的最多18个碳原子的烷基取代基为如甲基,乙基,丙基,丁基,戊基,己基,庚基,辛基,壬基,癸基,十一烷基,十二烷基,十四烷基,十六烷基或十八烷基,或其相应的支链异构体。
通式I的化合物的最多18个碳原子的烷氧基取代基为如甲氧基或乙氧基,或与上述烷基取代基对应的取代基。
通式I的化合物的最多18个碳原子的链烯基取代基为如乙烯基,丙-1-烯基(-CH=CH-CH3)或丙-2-烯基(-CH2-CH=CH2),或与上述烷基取代基对应的取代基。
通式I的化合物的最多18个碳原子的链烯氧基取代基为如丙-1-烯氧基(-O-CH=CH-CH3)或丙-2-烯氧基(-O-CH2- CH=CH2),或与上述烷基取代基对应的取代基。
通式I化合物的卤素取代基为氟,氯,溴或碘。
R2优选H,C1-C4烷基,C3链烯基,F,Cl或苯基;特别优选H,-CH3或Cl;更特别优选H或-CH3;
R2’优选为-OH,C1-C4烷氧基,或C3链烯氧基;特别优选-OH,C1-C2烷氧基或C3链烯氧基;并更特别优选-OH。
R3和R3’优选-O-CH2-CH(OA)-CH2-O-R7, ,-O-CR8R8’-(CH2)l-OA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,H,-OH,C1-C4烷基,环己基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯氧基,苄基,苄氧基或-CN;特别优选H,-OH,-O-CH2-CH(OA)-CH2-O-R7,
,-O-CH2-(CH2)1-OA,-CH3,C1-C4烷氧基,C3链烯氧基,F,Cl,苯基,苯氧基或-CN;并特别优选H,-OH,-O-CH2-CH(OA)-CH2-O-R7,,-O-CH2-(CH2)l-OA,-CH3,-OCH3,Cl,苯基或-CN。
R4,R4’及R4”优选H,C1-C4烷基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯基-C1-C3烷基或-CN;特别优选H,-CH3,C3链烯基,-OCH3,C3链烯氧基,F,Cl,苯基-C3烷基或-CN;并更特别优选H或-CH3。
R5优选为H或-CH3。
R6优选H,-COOR13,-CH3或苯基;并特别优选H或-CH3。
R7优选为C1-C8烷基,环己基,C3-C8链烯基,苯基,取代有1至3个C1-C4烷基或C1-C4烷氧基的苯基,或苄基,并特别优选C1-C8烷基,环己基,C3链烯基,苯基,或苄基。
R8和R8’优选彼此独立的为H或C1-C8烷基。
R10优选为H。
R11和R11’彼此独立优选为C1-C4烷基或苯基,特别是甲基。
X优选-O-或-NR8-,特别是氧原子。
l的数值优选1-15。
因此按本发明可使用的式I化合物符合如通式Ic
其中
A为-C(=O)-CR5=CH-R6;
及当R2’为OH或OA时,R1还可为-CH2-CH(OA)-CH2-O-R7;
R2和R2’彼此独立为H,-OH,-OA,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C2-C18链烯氧基,卤素,苯基或三氟甲基;
R9和R3’彼此独立为H,-OH,-OA,上述-OR1,-O-CHR8-(CH2)l-OA,-O-CH2-CH(OA)R9,-O-CH2-CH(OH))CH2-OA,-O-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C12烷基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基,环己基,C3-C18链烯基,苯基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C2-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基或-C(=O)-R12;
R8为H或C1-C18烷基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为C1-C18烷基,C2-C18边烯基或苯基;
R13为H,C1-C18烷基,C3-C18链烯基或苯基;
l为0至19;
p为0至10;
q为1至8
r为0至18;
t为0,1或2。
通式(I)化合物的优选形式,其中
R2为H,C1-C4烷基,C3链烯基,F,Cl或苯基;
R2’为C1-C4烷氧基,C3链烯氧基,-O-CO-R12或-OH;
R3和R3’彼此独立为H,-OH,-O-CH2-CH(XA)-CH2-O-R7,,-O-CHR8-(CH2)l-XA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,C1-C4烷基,环己基,C3链烯基,-OR131,F,Cl,三氟甲基,苯基,苄基,或-CN;
R4’及R4”彼此独立为H,C1-C4烷基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯基-C1-C3烷基或-CN;
R5为H,或-CH3。
R6为H,-COOR13,CH3或苯基;
R7为C1-C8烷基,环己基,C3-C8链烯基,苯基,取代有1至3个C1-C4烷基或C1-C4烷氧基苯基,或苄基;
R9为C1-C10烷基,苯基或苄基;
R11和R11’彼此独立为C1-C4烷基或苯基;
R12为C1-C18烷基,C2-C3链烯基,苯基,苯基C1-C4烷基或环己基;
R13为C1-C4烷基,C3链烯基,环己基,苯基C1-C4烷基或苯基;
R4,R14和R15,彼此独立为H,C1-C8烷基,F,Cl,C1-C4烷氧基,CF3,苯基,或CN;
R131为C1-C18烷基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,-COOR13,-CONH2,-CONHR132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,和/或苯氧基的C3-C18烷基;或C3链烯基;C6-C12环烷基;中间有一个或多个-O-可取代有OH或O-CO-R12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
X为-O-或-NR8-;
l为1-19;及
r为0至10。
这其中,通式(I)化合物特别优选形式为,其中E1和E2彼此独立为通式Ia或Ib且
其中
R1为或当R3’为-O-R8R8’-(CH2)l-XA时,R1还可为C1-C12的烷基或中间有-O-,-CO-O-或-OCO-的C6-C18的烷基;和当E1为通式Ib基团时,R1还可为-CH2-CH(XA)-CH2-O-R7;及当E1为式Ia,其中R2和R14都不是氢时,R1还可为-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,及-CH2-CH(OH)-CH2-XA;
R2为H,-CH3或Cl;
R2’为-OH;
R3为H,-CH3,C1-C4烷氧基,C3链烯氧基,F,Cl,苯基,苄氧基,或-CN;
-O-CH2-(CH2)l-XA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,或-OR131;
R4,R14,R15彼此独立为H,F,Cl,OCH3或CH3;
R4’及R4”,在三嗪环的间位位置,彼此独立为H,-CH3,C3链烯基,-OCH3,C3链烯氧基,F,Cl,苯基-C3烷基或-CN;
R5为H,CH3;
R6为H;
R7为C1-C8烷基,环己基,C3链烯基,苯基或苄基;
R8和R8’为H;
R9为C1-C10烷基;
R12为C1-C18烷基,苯基或环己基;
R131为C3-C18烷基,或取代有OH,C1-C18烷氧基,-NHCOR12和/或-O-CO-R12的C3-C18烷基;且
l为0至19。
其中
其中
A为-C(=O)-CR5=CH-R6;
R1彼此独立为-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)l-XA,-CH2-CH(OA)-R9,
-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,-CR8R’8-(CH2)l-C(=O)-XA或-C(=O)-O-CH2-C(=CH2)-R10;及当E1为式If基团,其中R2和R14都不为氢时,R1还为-A或-CH2-CH(OH)-CH2-XA;
R2彼此独立为,C1-C18烷氧基,C5-C12环烷基,C3-C6链烯基,卤素,苯基或三氟甲基;
R2’彼此独立为C1-C18烷氧基,C2-C18链烯氧基,-OH或-O-CO-R12;
R3和R3’彼此独立为H,-OH,OR1,-OR131,C1-C18烷基,C3-C18烷基,C9-C12环烷基,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C18烷基,C3-C6链烯基,-OR131,卤素,三氟甲基,苯基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基,C5-C12环烷基,C3-C18链烯基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基,中间有1个或多个-O-的C3-C50烷基,1-金刚烷基,2-金刚烷基,降冰片基,2-甲基降冰片基或-C(=O)-R12或-A;
R8或R8’彼此独立为H,C1-C18烷基,苯基,苯基-C1-C4-烷基,或取代有1-3个C1-C8烷基,C1-C8烷氧基,CX-C8链烯氧基,卤素或CF3的苯基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为H,C1-C18烷基,苯基,苯基-C1-C4烷基,C5-C12环烷基,C1-C12烷氧基,苯氧基,降冰片-2-基,5-降冰片烯-2-基或1-金刚烷基;
R13为H,C1-C18烷基,C3-C18链烯基,苯基,C5-C12环烷基,中间有1个或多个-O-的C3-C50烷基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基,2-金刚烷基,降冰片基,2-甲基降冰片基;
R14和R15,彼此独立为H,C1-C18烷基,C3-C18链烯基,C6-C12环烷基,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t,苯基-S(=O)t-或OR131;
R131为C1-C18烷基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,C3-C6链烯氧基,卤素,-COOR13,-CONH2,-CONHR132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,苯氧基和/或被C1-C18烷基,C1-C18烷氧基或卤素取代的苯氧基的C1-C18烷基;或C3-C18链烯基;C6-C12环烷基;C1-C4烷基和/或-OCOR12取代的C6-C12环烷基;中间有一个或多个-O-可取代有OH或O-CO-R12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
R132和R133彼此独立为C1-C12烷基,C3-C12烷氧基烷基,C4-C16二烷基氨基烷基或C5-C12环烷基;或
R132和R133一起为C3-C9亚烷基,C3-C9氧杂亚烷基或氮杂亚烷基;
X为-NR8-,-O-,-NH-(CnH2n)-NH-或-O-(CkH2k)-NH-;
K为2至4;
l为0至19;
m为2至8;
n为0至4;
p为0至10;
q为1至8;
r为0至18;及
t为0,1或2。
作为通式(Id)的UV吸收剂的相应聚合物叙述如下。
所述基团的实例见上述通式(I)化合物。
式Id聚合UV吸收剂中,特别令人感兴趣的是下述式Id化合物聚合得到的那些化合物,其中R1为-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,-CR8R’8-(CH2)l-C(=O)-XA或-C(=O)-O-CH2-C(=CH2)-R10,及,如果E1或E1和E2为衍生自二(2-羟基苯基)-三嗪或三(2-羟基苯基)-三嗪的通式Ig基团时,R1还包括-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-XA;及当E1为其中R2和R14都不为氢的式If基团时,R1还包括-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-XA或-A;特别是那些R1为如下基团的化合物,其中R1为-(CH2)p-SiR11R11’-CH=CH2,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,-CR8R’8-(CH2)l-C(=O)-XAor-C(=O)-O-CH2-C(=CH2)-R10,及当E1或E1和E2为式Ig基团,R1还包括-CH2-(C=CH2)-R10,-C(=O)-(CH2)q-CH=CH2,-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-XA;和当E1为其中R2和R14都不为氢的式If基团时,R1还包括-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-XA或-A。
这些化合物中特别优选其中E1为式If基团且E2为式Ig基团(衍生自二(2-羟基苯基)-三嗪)的化合物。
A为-C(=O)-CR5=CH-R6;
R1彼此独立为-CH2-CH(OA)-CH2-O-R7,-CHR8-(CH2)L-OA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-OA,
,-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA或-C(=O)-O-CH2-C(=CH2)-R10;
R2和R2’彼此独立为H,-OH,-OA,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C2-C18链烯氧基,卤素,苯基或三氟甲基;
R3和R3’彼此独立为H,-OH,-OA,-OR1,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C12烷基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基一C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基,环己基,C3-C18链烯基,苯基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C1-烷基或-C(=O)-R12;
R8为H或C1-C18烷基;
R9为C2-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为C1-C18烷基,C2-C18链烯基或苯基;
R13为H,C1-C18烷基,C3-C18链烯基或苯基;
l为0至19;
p为0至10;
q为1至8;
r为0至18;
t为0,1或2。
通式Id基团的优选形式如下:
R1优选为-CH2-CH(XA)-CH2-O-R7,-CR8R’8-(CH2)l-XA,-CH2-CH(OA)-R9,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA;特别优选-CH2-CH(OA)-CH2-O-R7,-CHR8-(CH2)l-OA,-CH2-CH(OA)-R9,或-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA;尤其优选-CH2-CH(OA)-CH2-O-R7,-CHR8-(CH2)l-OA,-CH2-CH(OA)-R9或
R2优选H,C1-C4烷基,C3链烯基,F,Cl或苯基;特别优选H,-CH3或Cl;更特别优选H或-CH3。
R2’优选为-OH,C1-C4烷氧基,或C3链烯氧基;特别优选-OH,或C1-C2烷氧基。
R3和R3’优选H,-OH,-OR1,-OR131,C1-C4烷基,环己基,C3链烯基,F,Cl,三氟甲基,苯基,苄基或-CN;特别优选H,-OH,-OR1,-CH3,C1-C12烷氧基,C2-C6烷酰氧基取代的C2-C18烷氧基,C3链烯基,F,Cl,苯基,苯氧基或-CN;并特别优选H,-OH,-OR1,-CH3,C1-C12烷氧基,Cl,苯基或-CN;
R3’通常为-OH,-OR1,OR131,且R3不包括-OR1。
R4,R4’及R4”优选H,C1-C4烷基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯基-C1-C3烷基或-CN;特别优选H,-CH3,C3链烯基,-OCH3,C3链烯氧基,F,Cl,苯基-C3烷基或-CN;并更特别优选H或-CH3。
R5优选为H,-CH3。
R6优选H,-COOR13,CH3或苯基;并特别优选H或-CH3。
R7优选为C1-C8烷基,环己基,C3-C8链烯基,苯基,取代有1至3个C1-C4烷基或C1-C4烷氧基的苯基,或苄基,并特别优选C1-C8烷基,环己基,C3链烯基,苯基,或苄基。
R8和R8’优选彼此独立的H或C1-C8烷基。
R10优选为H。
R11和R11’彼此独立优选为C1-C4烷基或苯基,特别是甲基。
X优选-O-或-NR8-,特别是氧原子。
l的数值优选1-15。
通式(Id)化合物的优选形式为,其中
-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA;
R2为H,C1-C4烷基,C3链烯基,F,Cl或苯基;
R2’为C1-C4烷氧基,C3链烯氧基,-OA,-O-COR12或-OH;
R3和R3’彼此独立为H,-OH,-OR1,-OR131,C1-C4烷基,环己基,C3链烯基,F,Cl,三氟甲基,苯基,苄基或-CN;
R4’及R4”彼此独立为H,C1-C4烷基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯基-C1-C3烷基或-CN;
R5为H,-CH3。
R6为H,-COOR13,CH3或苯基;
R7为C1-C8烷基,环己基,C3-C8链烯基,苯基,取代有1至3个C1-C4烷基或C1-C4烷氧基的苯基,或苄基;
R8和R8’为彼此独立的H或C1-C18烷基。
R9为C1-C10烷基,苯基或苄基;
R12为H,C1-C18烷基,苯基,苯基C1-C4烷基或环己基;
R13为C1-C4烷基,C3链烯基,环己基,苯基-C1-C4烷基或苯基;
R4,R14和R15,彼此独立为H,F,Cl,C1-C4烷氧基,CF3,苯基,CN或C1-C8烷基;
R131为C1-C18烷基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,-COOR13,-CONH2,-CONHR132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,和/或苯氧基的C3-C18烷基;或C3链烯基;C6-C12环烷基;中间有一个或多个-O-可取代有OH或O-CO-R12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
X优选-O-或-NR8-;
l为1-19;及
r为0至10。
包括通式(Id)单位的聚合物的特别优选形式为,其中
A为-C(=O)-CR5=CH-R6;
R2为H,-CH3,-OCH3,C3链烯氧基或Cl;
R2’为-OH;
R3为H,-CH3,C1-C4烷氧基,C3链烯氧基,F,Cl,苯基,苄氧基或-CN;
R3’为-OR1,-OR131;
R4,R14和R15,彼此独立为H,F,Cl,苯基,CH,OCH3或CH3;
R4’及R4”彼此独立为H,-CH3,C3链烯基,-OCH3,C3链烯氧基,F,Cl,苯基-C3烷基或-CN;
R5为H或-CH3。
R6为H或-CH3;
R7为C1-C8烷基,环戊基,环己基,C3链烯基,苯基或苄基;
R8为H或C1-C8烷基。
R9为C1-C10烷基或苯基;
R12为C1-C18烷基,苯基或环己基;
R131为C3-C18烷基,或取代有C1-C18烷氧基,OH,苯氧基,-NHCOR12和/或-OCOR12的C3-C18烷基;且
l为1-19;
更特别优选的形式为,其中
A为-C(=O)-CR5=CH-R6;
R1彼此独立为-CH2-CH(OA)-CH2-O-R7,-CH2-CH(OA)-R9,
R2为H或CH3;
R2’为-OH;
R3为H,-CH3,Cl,苯基;
R3’为-OR1或-OR131;
R4为H或CH3;
R4’及R4”,R14和R15为H;
R5为H或-CH3;
R6为H;
R7为C1-C8烷基;
R9为C1-C10烷基;
R12为C1-C8烷基;
R131为C3-C18烷基,或取代有-OCOR12的C3-C18烷基;且
l为1-10。
特别优选通式(Id)化合物,其中R3和R3基团至少一个为-OR1。
本发明更进一步涉及,特别是包含通式Id单位的新聚合物,其中E1为通式If且E2为通式Ig。这其中,特别优选有混合取代基的化合物其中R3或R3’都不是-OR1;特别是那些R2’为OH且R3’为C1-C18烷氧基或中间有-O-或-OCOR12和/或取代有C1-C18烷氧基或C5-C12环烷氧基的C2-C18烷氧基,其中R12为C1-C18烷基,苯基,苯基-C1-C4烷基或C5-C12环烷基,特别是那些其中R1为-CR8R8’-(CH2)l-XA的化合物。
均聚物和共聚物都是合适的,其中共聚物可由至少两个不同的通式(Id)化合物(结构单元)或至少一个通式(Id)化合物与一个其它共聚用单体(乙烯不饱和化合物)合成。通式I的化合物可用以制备新的均聚物和共聚物。
通式(Id)的至少两个不同化合物共聚反应制得的聚合化合物也有特别的技术特征。
适合的其它共聚用单体(与通式(Id)化合物不同的共聚用单体)包括丙烯酸,甲基丙烯酸,丙烯酸酯,甲基丙烯酸酯,丙烯酸酰胺,甲基丙烯酸酰胺,乙烯醚,苯乙烯,苯乙烯衍生物,乙烯基吡啶,丙烯腈,甲基丙烯腈,乙类基吡咯烷酮,乙烯基吡咯酮烷衍生物,及具空间位阻胺类的乙烯不饱和衍生物,2-(2’-羟苯基)苯并***,2-羟基苯酮及具空间位阻的苯酚。
特别重要的是使用其它可共聚稳定剂,例如具空间位阻胺类乙烯不饱和衍生物(HALS),2-(2’-羟苯基)苯并***,2-羟基苯酮及具空间位阻的苯酚。
对于共聚物,除至少一个通式Id化合物的单元,也可进一步含其它共聚用单体且其可作为光稳定剂,进而共聚用单体:通式Id单体的比率优选10∶1以内,特别是在1∶1至5∶1的范围内。
可用作共聚用单体的相应HALS通常以结构单元为特征,其中3个自由键可被H或有机取代基饱和,且分子含有至少一个可聚合的乙烯不饱和双键;相应的化合物描述于US-A-4942238,US-A-4983737和EP-A-0634399,及其所引文献。
US-A-5 099 027,US-A-4 528 311,US-A-5 147 902,ResearchDisclosure 32 592,US-A-4 785 063,US-A-4 892 915,US-A-4611 061,EP-A-0 190 003,EP-A-0 508 744,US-A-4 716 234,US-A-3 493 539,US-A-5 234 807,US-A-5 256 359,US-A-5 385 815,US-A-5 372 922,JP-A-03-139 590,EP-A-0 431 868,JP-A-03-8547,GB-A-2 232 667,EP-A-0 282 294,EP-A-0 343 996,EP-A-0 133 164,EP-A-0 131 468,J.Macromol.Sci.,Pure Appl.Chem.A30(9-10),741(1993)and Polym.Bull.12(5),375(1984)及其所引文献。
可用作共聚用单体的相应2-羟基苯酮通常以结构单元为特征,其中四个自由键可以H或有机取代基饱和,且分子含有至少一个可聚合的乙烯不饱和双键;相应的化合物描述于CH-B-383001和CH-B-376899,及其所引文献。
可用作共聚用单体的相应具空间位阻的苯酚通常以结构单元为特征,其中三个自由键可以有机取代基饱和,且分子含有至少一个可聚合的乙烯不饱和双键,通常在羟基的对位取代基中;相应的化合物描述于US-A-370850及其所引文献。
其它共聚用单体(与通式(Id)化合物不同的共聚用单体)优选如下通式(II)-(VII)的化合物
(II) R18-CH=C(R17)-C(=O)-X’-R20,
其中X’是-O-或-NR19-;
R17是H,C1-C4烷基,-CH2-COOR21,-Cl或-CH;
R18是H,-COOR21或-CH3;
R19为H,C1-C8烷基,C4-C12环烷基,-N(Rx)2取代的C1-C4烷基,-S(=O)-RX,-C(CH3)2-CH2-C(=O)-CH3,-C(CH3)2-CH2-SO3M,-(CH2)s-SO3M或
R20为H,C1-C18烷基,C2-C18链烯基,中间有一个或多个O原子的C2-C18烷基,后者可取代有OH,-(CH2)s-SO3M,,-CH2F,-CH2Cl,-CH2CN,-CH2CH2Cl,-CH2CH2CN,-CH2CH2-COORX,C7-C11苯基烷基,萘基,-N(RX)2取代的C1-C4烷基,金刚烷基或C6-C12环烷基;
R21为H,C1-C18烷基,苯基或C2-C18链烯基;
RX为C1-C4烷基或苯基;
RY为H,C1-C12烷基,苯基,-CO-ORX,-CN,-F,或-Cl;
M为H或碱金属;且
s为1至5。
(III) R22-C(=O)-O-CH=Ch2,
其中R22为C1-C19烷基或苯基。
(IIIa) R22a-O-CH=CH2,
其中R23为H或-CH3;
R24为H,-CR23=CH2,-C(O)-苯基或-SO3M;且
其中R25为H或-CH3。
(VI) -CH2=CR26-R27,
R26为H,-F,-Cl或-CH3
及上述可聚合的具空间位阻胺类的乙烯不饱和衍生物(HALS),2-(2’-羟苯基)苯并***,2-羟基苯酮及具空间位阻的苯酚。
能式(II)-(VII)的共聚用单体优选:
(II) R18-CH=C(R17)-C(=O)-X-R20,
其中R17是H,CH3,-CH2-COOR21或-CN;
R18是H,-COOR21或-CH3;
R19为H,C1-C4烷基,-C(CH3)2-CH2-C(=O)-CH3,-C(CH3)-CH2-SO3M,或-(CH2)s-SO3M;
R20为H,C1-C18烷基,中间有一个或多个O原子的C2-C30烷基,或-(CH2)5-SO3M
R21为H,C1-C18烷基,苯基或C2-C18链烯基
X是-O-或-NR19-;
M为H或碱金属;且
s为1至5。
(III) R22-C(=O)-O-CH=CH2,
其中R22为C1-C19烷基或苯基
(IIIa) R22a-O-CH=CH2,
其中R22a为C1-C18烷基;
其中R23为H或-CH3;
R24为H,-CR23=CH2,-C(O)-苯基或SO3M;且
M为H或碱金属。
其中R25为H或-CH3。
通式(II)-(VII)取代基的可能的含义对应于通式(I)或(Id)化合物的定义。
上述通式中任一18个碳原子以内的,中间有一个或多个O原子的取代基为如-(CH2-CH2O)1-8-CH3,-(CH2-(CH2-O)1-8-C2H5或-(CH2-CH2-CH2-O)1-5-CH3。
上述通式中的任一碱金属取代基为Li,Na或K。
特别优选的其它共聚用单体(与通式(Id)不同的共聚用单体)为通式(II)-(IV)和(VII)的化合物。
优选以至少一种优选的通式(Id)化合物与至少一种通式(II)-(VII)的共聚用单体聚合反应制得的共聚物。
特别优选以至少一种特别优选的通式(Id)化合物与至少一种通式(II)-(IV)或(VII)的共聚用单体聚合反应制得的共聚物。
更特别优选以至少一个更特别优选的通式(Id)化合物与至少一个通式(II)-(IV)或(VII)的共聚用单体聚合反应制得的共聚物,
其中R17是H或CH3;
R18是H或-CH3;
R19为H,C1-C4烷基,-C(CH3)-CH2-SO3M,或-(CH2)s-SO3M;
R20为H,C1-C8烷基,中间有一个或多个O原子的C2-C20烷基;
R22为CH3;
R22a为C1-C4烷基;
R23和R24为H;
M为H,Li,Na,或K;
X是-O-或-NR19-;及
s为2或3。
通式(I)或(Id)的化合物为已知的或原则上可通过已知方法制备。以下的反应方案例举了制备由三嗪基单间苯二酚衍生的通式(I)或(Id)的化合物的基础的二步(a+b)方法。二或三间苯二酚衍生的化合物也可用相似方法制备。可能的制备方法详见EP-A-0434608。a)间苯二酚基团的对位羟基烷基化(通过如缩水甘油基醚或ω-溴代醇): (Ar=取代或无取代的苯基;R=如烷基) (Ar=取代或无取代的苯基;i=1-20)b)脂肪羟基的丙烯酰化或甲基丙烯酰化: (Ar=取代或无取代的苯基;R=如烷基;R1=H或-CH3)(Ar=取代或无取代的苯基;i:1-20;R1=Hor-CH3)
通式为的三嗪基间苯二酚用作起始化合物,其可以按已知方法或类似的方法制备(EP-A-0434608;H.Brunetti and C.E.Luthi,Helv.Chim.Acta55,1566(1972);EP-A-0577559;GB-A-884802)。
通式(Id)的单体化合物之一的聚合反应(加成聚合反应)可由自由基、阴离子或阳离子引发剂引发。优选自由基引发剂,其由于热分解为自由基,例如,有机过氧化物或氢过氧化物,偶氮化合物或氧化还原催化剂。聚合反应也可由高能辐射引发。聚合反应可在溶液,乳液,分散体系中或本体中完成。这些方法对本领域技术人员是已知的。合适的聚合反应方法也描述于EP-A—0577122,第9页第46行至第10页第35行。
通式(I)化合物的实例如下:No. L1,L3(202) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-CH=CH2(207) L1=n-C6H13,L3=-(CH2)11-O-C(O)-C(CH3)=CH2(208) L1=-(CH2)11-O-C(O)-CH3,L3=-(CH2)11-O-C(O)-C(CH3)=CH2 No. L1(300) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-CH=CH2(n-C4H9:正丁基)No. L1 No. L1,L3(500) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-CH=CH2(501) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-C(CH3)=CH2(502) -(CH2)11-O-C(O)C(CH3)=CH2(503) -CH2-CH(n-C4H9)-O-C(O)-C(CH3)=CH2(504) L1=n-C6H13,L3=-(CH2)11-O-C(O)-C(CH3)=CH2 (506) L1=n-C6H13,L3=-(CH2)11-O-C(O)-CH=CH2(507) -CH2-CH(OH)-CH2-O-C(O)-C(CH3)=CH2
除以上提及的以外,式(Id)单体的实例还有下列化合物:No. L1(100) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-CH=CH2(n-C4H9:n-butyl)(101) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-C(CH3)=CH2(102) -(CH2)11-O-C(O)-CH=CH2(103) -(CH2)11-O-C(O)-C(CH3)=CH2(104) -CH2-CH(n-C4H9)-O-C(O)-C(CH3)=CH2(106) -CH2-CH2-O-C(O)-C(CH3)=CH2 No. L1(200) -CH2-CH2-O-C(O)-CH=CH2 No. L1,L3(201) -CH2-CH2-O-C(O)-C(CH3)=CH2(203) -(CH2)11-O-C(O)-CH=CH2(204) -(CH2)11-O-C(O)-C(CH3)=CH2(205) -CH2-CH(n-C4H9)-O-C(O)-C(CH3)=CH2(206) -CH2-CH(n-C4H9)-O-C(O)-CH=CH2 No. L1(301) -(CH2)11-O-C(=O)-CH=CH2(302) -(CH2)11-O-C(=O)-C(CH3)=CH2 No. L1(400) -CH2-CH(CH2-O-n-C4H9)-O-C(O)-C(CH3)=CH2(401) -(CH2)11-O-C(O)-CH=CH2(402) -(CH2)11-O-C(O)-C(CH3)=CH2(403) -CH2-CH(n-C4H9)-O-C(O)-C(CH3)=CH2(404) -CH2-CH2-O-C(O)-C(CH3)=CH2
由通式(Id)化合物制备的聚合物的实例如下:
(600)化合物(204)的均聚物
(601)化合物(204)和丙烯酸正丁酯以摩尔比1∶4的共聚物
(602)化合物(207)的均聚物
(603)化合物(207)和丙烯酸正丁酯以摩尔比1∶4的共聚物
(604)化合物(504)的均聚物
(605)化合物(504)和丙烯酸正丁酯以摩尔比1∶4的共聚物
(606)化合物(504)和丙烯酸正十二烷基酯以摩尔比1∶的共聚物
(607)化合物(102)的均聚物
(608)化合物(102)和丙烯酸正-丁基酯以摩尔比1∶4的共聚物
(609)化合物(402)的均聚物
(610)化合物(402)和丙烯酸正丁基酯以摩尔比1∶2的共聚物
(611)化合物(103)的均聚物
(612)化合物(103)和丙烯酸酯正丁基酯以摩尔比1∶2的共聚物
(613)化合物(400)的均聚物
(614)化合物(400)和丙烯酸正-丁基酯以摩尔比1∶2的共聚物
(615)化合物(105)和丙烯酸正-丁基酯以摩尔比1∶2的共聚物
(616)化合物(405)和丙烯酸正-丁基酯以摩尔比1∶2的共聚物
除上述新的共聚物外,通式(I)化合物通过共聚反应结合到乙烯不饱和单体聚合反应制备的聚合物上。这些单体包括,例如6以下单体;丙烯酸,甲基丙烯酸,丙烯酸和甲基丙烯酸的酯,丙烯酸和甲基丙烯酸酰胺,丙烯腈,苯乙烯,α-甲基苯乙烯,丁二烯,异戊二烯,马来酸酐,马来酸的酯、酰胺和酰亚胺,氯乙烯,亚氯乙烯,醋酸乙烯酯,乙烯基丁醛,乙烯基烷基醚及N-乙烯基吡咯烷。优选结合到由丙烯酸,甲基丙烯酸,丙烯酸和甲基丙烯酸的酯或酰胺,苯乙烯或丙烯腈制得的聚合物上。聚合物可由一个或多个这样的单体聚合而成。通式(I)不饱和化合物在聚合反应时加入,以发生共聚反应。
聚合反应可由自由基、阴离子或阳离子引发剂引发。优选自由基引发剂,其由于热分解为自由基,例如,有机过氧化物或氢过氧化物,偶氮化合物或氧化还原催化剂。聚合反应也可由高能辐射引发。例如,在可辐射固化的涂料(UV-固化或ESR-固化)。此时,可共聚的羟基苯基-s-三嗪在薄膜形成时结合到涂料基质中。
特别适合此共聚反应的方法为基团转移聚合反应,其中通过特定引发剂形成“活”聚合物。适合此目的的引发剂的实例为1-三甲基甲硅烷氧基-1-烷氧基-2-甲基丙烯。此基团转移聚合反应方法的建立已有一些年了并请见如US-A-4695607和US-A-4414372。
聚合反应可在溶液、乳液、分散体系或在本体中完成。这些方法对本领域技术人员是已知的。
适合于通过共聚缩合反应或共聚加成反应结合的通式(I)的化合物特别是含有两个官能团的。如果参与共聚缩合反应或共聚加成反应的通式(I)化合物的量很少,则合适的通式(I)化合物也可只含有一个官能团。
通式(I)的单官能团、双官能团或三官能团化合物可结合到,例如,聚脂,聚醚脂,聚酰胺,聚氨基甲酸酯,聚碳酸酯,环氧树脂,酚醛树脂,密胺树脂或聚酯树脂中。通过为此目的的本领域技术人员已知的方法,在制备缩合或加成聚合物时完成加成结合。
此结合也可发生在低聚物或多聚物中间体上。例如,通式(I)的不饱和化合物可加入于不饱和的聚酯树脂和其与其它乙烯化合物的混合物中,此混合物再以自由基引发剂来固化。或低聚环氧树脂可与通式(I)的功能化合物反应并随后以环氧化物固化剂处理该产物。再者,通式(I)的OH-功能化合物可与密胺树脂反应,随后以丙烯酸酯树脂加成固化所得化合物。
在树脂的最终固化前使用前体结合于聚氨酯,酚醛树脂或聚酯树脂上是可能的。也可以酸或碱催化固化树脂而不影响三嗪化合物。
进一步结合的可能包括通式(I)的化合物与含有合适官能团的聚合物反应。例如,含羟基,羧基,酸酐,氨基,环氧基或异氰酸酯基的聚合物。其实例为丙烯酸和甲基丙烯酸,羟基烷基(甲基)丙烯酸酯,缩水甘油(甲基)丙烯酸酯的共聚物,部分水解的聚乙烯乙酸酯或乙烯-乙酸乙烯酯共聚物,部分酯化的纤维素,部分水解的聚烷基(甲基)丙烯酸酯,含有活性末端基团的聚脂或聚氨脂,环氧树脂或马来酸、马来酸酐或马来酸单酯或单酰胺的共聚物。
适合于反应的通式(I)的化合物为含有可与聚合物官能团反应的官能团的化合物。这些可以是,例如,羟基,羧基,酯,氨基,环氧化基团或异氰酸酯基团。如果需要,例如,通过通式(I)化合物修饰含OH基的聚合物,可使用如含有至少一个异氰酸酯基,环氧化基团,羧基或酯基的通式(I)化合物。含有环氧基团的聚合物可与,例如,含有至少一个羟基、羧基或氨基的通式(I)的化合物反应。马来酸酐的共聚物可与,例如,含有羟基、氨基或环氧基团的通式(I)的化合物反应。
这些反应可通过聚合物-同系反应的常规方法完成。反应优选在溶液中进行。与聚合物所有的官能团或只是其中一些反应都是可能的。这依赖于反应所使用通式(I)化合物的量。这些反应的详细材料在实施例中给出。
结合到聚合物的特定方法是通式(I)的乙烯不饱和衍生物接枝到碳水聚合物上。含有乙烯不饱和基团的通式(I)化合物已非常详细地加以定义。碳氢聚合物可以是饱和的或不饱和的。前者包括聚烯烃,例如,聚乙烯,聚丙烯,聚丁烯和聚异丁烯。后者包括二烯聚合物和其与烯烃的共聚物,例如,聚丁二烯,聚异戊二烯,丙烯-丁二烯和乙烯-丙烯-丁二烯。优选接枝到聚烯烃上,特别优选聚乙烯。
接枝反应可在溶液中或在本体中进行。催化剂可用自由基形成物,也可用于不饱和化合物的均聚反应或共聚合反应。
通式(I)化合物结合到聚合物上的所有这些方法可使用相对小量的三嗪完成,例如,基于改性后的聚合物使用量比为0.05-5%。此用量使聚合物对光,氧化和热破坏有耐性,且此稳定性不会由于稳定剂的迁移或洗脱而丧失。为此目的,优选使用0.1-3%量比的通式(I)化合物。
但是,此方法也可使用大量的三嗪,如基于改性后的聚合物使用量比为5-50%。如果需要使用如此改性的聚合物作为聚合稳定剂这是合适的。这些聚合稳定剂可以加到有机材料中,特别是有机聚合物中。但是,聚合稳定剂也可作为塑料模具的薄层保护层,如溶解形式或共挤压,例如,US—A—4676870描述的。
本方法的进一步应用是通式(I)的化合物结合于聚合物微粒上。EP—A—0226538描述了通过共聚加成反应或共聚缩合反应结合光稳定剂到可用作涂料分散相的微粒上。在此方案中基于改性的聚合物,量比0.1—30%,优选量比0.5—10%的通式(I)的化合物结合到微粒上。
在微粒上的结合较好的是使用基团转移聚合方法完成,如EP—A—0293871中的描述。
本发明还涉及通过所述方法制备的改性聚合物,其含有所述量比的化学键合形式的通式(I)的化合物,使其对光,氧和热破坏稳定。
可以按聚合物技术中的常规方法,将式I和式Id的新稳定剂和按本发明改性的聚合物与各种添加剂混合。这些添加剂可以是稳定剂或制备助剂或色素或其它添加剂。添加剂的实例如下:
1.抗氧剂
1.1 烷基化的一元酚,例如2,6-二叔丁基-4-甲基苯酚,2-叔丁基-4,6-二甲基苯酚,2,6-二叔丁基-4-乙基苯酚,2,6-二叔丁基-4-正丁基苯酚,2,6-二叔丁基-4-异丁基苯酚,2,6-二环戊基-4-甲基苯酚,2-(α-甲基环己基)-4,6-二甲基苯酚,2,6-二(十八烷基)-4-甲基苯酚,2,4,6-三环己基苯酚,2,6-二叔丁基-4-甲氧基甲基苯酚,壬基苯酚,其侧链为直链或支链,如2,6-二壬基-4-甲基苯酚,2,4-二甲基-6-(1’-甲基十一烷-1’-基)苯酚,2,4-二甲基-6-(1’-甲基十七烷-1’-基)苯酚,2,4-二甲基-6-(1’-甲基十三烷-1’-基)苯酚及其混合物。
1.2 烷基硫基甲基苯酚,例如,2,4-二辛硫基甲基-6-叔丁基苯酚,2,4-二辛硫基甲基-6-甲基苯酚,2,4-二辛硫基甲基-6-乙基苯酚,2,6-二-十二烷硫基甲基-4-壬基苯酚。
1.3 对苯二酚和烷基化的对苯二酚,例如,2,6-二叔丁基-4-甲氧基苯酚,2,5-二叔丁基对苯二酚,2,5-二叔戊基对苯二酚,2,6-二苯基-4-十八烷氧基苯酚,2,6-二叔丁基对苯二酚,2,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯基硬脂酸酯,双-(3,5-二叔丁基-4-羟基苯基)己二酸酯。
1.4 生育酚,例如α-生育酚,β-生育酚,γ-生育酚,δ—生育酚及其混合物(维生素E)。
1.5 羟基化的硫代二苯基醚,例如,2,2’-硫代双(6-叔丁基-4-甲基苯酚),2,2’-硫代双(4-辛基苯酚),4,4’-硫代双(6-叔丁基-2-甲基苯酚),4,4’-硫代双(6-叔丁基-2-甲基苯酚),4,4’-硫代双-(3,6-二仲戊基苯酚),4,4’-双(2,6-二甲基-4-羟基苯基)二硫化物。
1.6 亚烷基二苯酚,例如2,2’-亚甲基二(6-叔丁基-4-甲基苯酚),2,2’-亚甲基二(6-叔丁基-4-乙基苯酚),2,2’-亚甲基二[4-甲基-6-(2-甲基环己基)苯酚],2,2’-亚甲基二(4-甲基-6-环己基苯酚),2,2’-亚甲基二(6-壬基-4-甲基苯酚),2,2’-亚甲基二(4,6-二叔丁基苯酚),2,2’-亚乙基二(4,6-二叔丁基苯酚),2,2’-亚乙基二(6-叔丁基-4-异丁基苯酚),2,2’-亚甲基二[6-(α-甲基苄基)-4-壬基苯酚],2,2’-亚甲基二[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4’-亚甲基二(2,6-二叔丁基苯酚),4,4’-亚甲基二(6-叔丁基-2-甲基苯酚),1,1-二(5-叔丁基-4-羟基-2-甲基苯基)丁烷,2,6-二(3-叔丁基-5-甲基-2-羟基苄基)-4甲基苯酚,1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷,1,1-二(5-叔丁基-4-羟基-2-甲基-苯基)-3-正十二烷基巯基丁烷,乙二醇二[3,3-二(3’-叔丁基-4’-羟基苯基)丁酸酯],二(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯,二[2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯,1,1-二(3,5-二甲基-2-羟基苯基)丁烷,2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷,2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷,1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7 O-,N-和S-苄基化合物,例如,3,5,3’,5’-四-叔丁基-4,4’-二羟基二苄基醚,十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯,十三烷基-4-羟基-3,5-二叔丁基苄基巯基乙酸酯,三(3,5-二叔丁基-4-羟基苄基)胺,二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯,二(3,5-二叔丁基-4-羟基苄基)硫化物,异辛基-3,5-二叔丁基-4-羟基苄基巯基乙酸酯。
1.8 羟苄基化的丙二酸酯,例如,双十八烷基-2,2-二(3,5-二叔丁基-2-羟基苄基)丙二酸酯,双十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)-丙二酸酯,双十二烷基巯基乙基-2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸酯,二[4-(1,1,3,3-四甲基丁基)苯基]-2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸酯。
1.9 芳香族羟苄基化合物,例如,1,3,5-三(3,5-二叔丁基-4-羟苄基)-2,4,6-三甲基苯,1,4-二(3,5-二叔丁基-4-羟苄基)-2,3,5,6-四甲基苯,2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯酚。
1.10 三嗪化合物,例如,2,4-二(辛基巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-二(3,5-二叔丁基-4-羟基-苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-二(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪,2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪,1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯,1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯,2,4,6-三(3,5-二叔丁基-4-羟基苯基乙基)-1,3,5-三嗪,1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰)-六氢-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟苄基)异氰脲酸酯。
1.11 苄基膦酸酯,例如,2,5-二叔丁基-4-羟基苄基膦酸二甲酯,3,5-二叔丁基-4-羟基苄基膦酸二乙酯,3,5-二叔丁基-4-羟基苄基膦酸双十八烷基酯,5-叔丁基-4-羟基-3-甲基苄基膦酸双十八烷基酯,3,5-二叔丁基-4-羟基苄基膦酸单乙基酯的钙盐。
1.12 酰氨基苯酚,例如,4-羟基月桂酰苯胺,4-羟基硬脂酰苯胺,N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13 β-(3,5-二叔丁基-4-羟基苯基)丙酸与单或多元醇形成的酯,例如与下列醇形成的酯:甲醇,乙醇,正辛醇,异辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,1,2-乙二醇,1,2-丙二醇,新戊二醇,硫代二甘醇,二甘醇,三甘醇,季戊四醇,三(羟乙基)异氰脲酸酯,N,N’-二(羟乙基)常酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂二环[2,2,2]-辛烷。1.14 β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与单或多元醇形成的酯,如与下列醇形成的酯,甲醇,乙醇,正辛醇,异辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,1,2-乙二醇,1,2-丙二醇,新戊二醇,硫代二甘醇,二甘醇,三甘醇,季戊四醇,三(羟乙基)异氰脲酸酯,N,N’-二(羟乙基)草酰胺,3-硫杂十一醇,3-硫杂十五醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂2,6,7-三氧杂二环[2,2,2]辛烷。1.15 β-(3,5-二环己基-4-羟基苯基)丙酸与单或多元醇形成的酯,如与下列醇形成酯,甲醇,乙醇,辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,1,2-乙二醇,1,2-丙二醇,新戊二醇,硫代二甘醇,二甘醇,三甘醇,季戊四醇,三(羟乙基)异氰脲酸酯,N,N’-二(羟乙基)草酰胺,3-硫杂十一醇,3-硫杂十五醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂2,6,7-三氧杂二环[2,2,2]辛烷。1.16 3,5-二叔丁基-4-羟基苯基乙酸与单或多元醇形成的酯,如,与下列醇形成的酯,甲醇,乙醇,辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,1,2-乙二醇,1,2-丙二醇,新戊二醇,硫代二甘醇,二甘醇,三甘醇,季戊四醇,三(羟乙基)异氰脲酸酯,N,N’-二(羟乙基)草酰胺,3-硫杂十一醇,3-硫杂十五醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂二环[2,2,2]辛烷。1.17 β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺,如N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二胺,N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二胺,N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰基)肼。1.18 抗坏血酸(维生素C)1.19 胺抗氧剂,例如,N,N’-二异丙基-对-苯二胺,N,N’-二仲丁基-对-苯二胺,N,N’-二(1,4-二甲基戊基)-对-苯二胺,N,N’-二(1-乙基-3-甲基戊基)-对-苯二胺,N,N’-二(1-甲基庚基)-对-苯二胺,N,N’-二环己基-对-苯二胺,N,N’-二苯基-对-苯二胺,N,N’-二(2-萘基)-对-苯二胺,N-异丙基-N’-苯基-对-苯二胺,N-(1,3-二甲基丁基)-N’-苯基-对苯二胺,N-(1-甲基庚基)-N’-苯基-对苯二胺,N-环己基-N’-苯基-对苯二胺,4-(对甲苯氨磺酰)-二苯胺,N,N’-二甲基-N,N’-二仲丁基-对苯二胺,二苯胺,N-烯丙基二苯胺,4-异丙氧基二苯胺,N-苯基-1-萘胺,N-(4-叔辛基苯基)-1-萘胺,N-苯基-2-萘胺,辛基化的二苯胺,如P,P’-二叔辛基二苯胺,4-正丁基氨基苯酚,4-丁酰氨基苯酚,4-壬酰氨基苯酚,4-十二烷酰氨基苯酚,4-十八烷酰氨基苯酚,二(4-甲氧苯基)胺,2,6-二叔丁基-4-二甲基氨基甲基苯酚,2,4’-二氨基二苯基甲烷,4,4’-二氨基二苯基甲烷,N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷,1,2-二[(2-甲基苯基)氨基]乙烷,1,2-二(苯基氨基)丙烷,邻甲苯基双胍,二[4-(1’,3’-二甲基丁基)苯基]胺,叔辛烷基化的N-苯基-1-萘胺,单和二烷基化的叔丁基/叔辛基二苯胺的混合物,单和二烷基化的壬基二苯基胺的混合物,单和二烷基化的十二烷基二苯胺的混合物,单和二烷基化的异丙基/异己基二苯胺的混合物,单和二烷基化的叔丁基二苯胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,单和二烷基化的叔丁基/叔辛基吩噻嗪的混合物,单和二烷基化的叔辛基吩噻嗪的混合物,N-烯丙基吩噻嗪,N,N,N’,N’-四苯基-1,4-二氨基丁-2-烯,N,N-二(2,2,6,6-四甲基-哌啶-4-基-六亚甲基二胺,二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯,2,2,6,6-四甲基哌啶-4-酮,2,2,6,6-四甲基哌啶-4-醇。2.UV吸收剂和光稳定剂2.1 2-(2’-羟基苯基)苯并***,例如,2-(2’-羟基-5’-甲基苯基)-苯并***,2-(3’,5’-二叔丁基-2’-羟基苯基)苯并***,2-(5’-叔丁基-2’-羟苯基)苯并***,2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并***,2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯-苯并***,2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯-苯并***,2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并***,2-(2’-羟基-4’-辛氧苯基)苯并***,2-(3’,5’-二叔戊基-2’-羟基苯基)苯并***,2-(3’,5’-二(2,2-二甲基苄基)-2’-羟苯基)苯并***,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧羰基乙基)苯基)-5-氯-苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)-羰基乙基]-2’-羟苯基)-5-氯-苯并***、2-(3-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基-5-氯-苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并***、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并和2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基苯并***的混合物,2,2’-亚甲基-二[4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧羰基乙基)-2’-羟基苯基]-2H-苯并***与聚乙二醇300的酯基转化产物;[R-CH2-CH2-COO(CH2)3]2,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并***-2-基-苯基。2.2 2-羟基苯酮,例如,4-羟基,4-甲氧基,4-辛氧基,4-癸氧基、4-十二烷氧基,4-苯甲氧基,4,2’,4’-三羟基和2’-羟基-4,4’-二甲氧基衍生物。
2.3 取代和未取代苯甲酸的酯,例如,4-叔丁基-苯基水杨酸酯,水杨酸苯酯,辛基苯基水杨酸酯,联苯甲酰间苯二酚,二(4-叔丁基苯甲酰基)间苯二酚,苯甲酰基间苯二酚,2,4-二叔丁基苯基3,5-二叔丁基-4-羟基苯甲酸酯,3,5-二叔丁基-4-羟基苯甲酸十六烷基酯,3,5-二叔丁基-4-羟基苯甲酸十八烷基酯,2-甲基-4,6-二叔丁基苯基3,5-二叔丁基-4-羟基苯甲酸酯。
2.4 丙烯酸酯,例如,α-氰基-β,β-3-二苯基丙烯酸乙酯,α-氰基-β,β-二苯基丙烯酸异辛酯,α-甲酯基肉桂酸甲酯,α-氰基-β-甲基-对甲氧肉桂酸甲酯,2-氰基-β甲基-对甲氧基-肉桂酸丁酯,2-甲酯基-对甲氧基肉桂酸甲酯和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-二[4-(1,1,3,3-四甲基丁基)苯酚]的镍复合物,如1∶1或1∶2的复合物,有或没有附加的配体如正丁基胺,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的单烷基酯的镍盐,如甲基或乙基酯,酮肟的镍复合物,如2-羟基-4-甲基苯基十一烷基酮肟,1-苯基-4-月桂酰-5-羟基吡唑的镍复合物,有或没有附加的配体。2.6 位阻胺,例如二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯,1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩合物,N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺与4-叔辛基氨基-2,6-二氯-1,3,5-***的缩合物,三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷-四羧酸酯,1,1’-二(1,2-乙烷二基)二(3,3,5,5-四甲基哌嗪酮,4-苯甲酰基-2,2,6,6-四甲基哌啶,4-硬脂酰氧-2,2,6,6-四甲基哌啶,二(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯,3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4,5]癸-2,4-二酮,二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯,N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的缩合物,2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物,2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4,5]癸烷-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮,3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷二酮,4-十六烷酰氧基和4-硬脂酰氧基-2,2,6,6-四甲基哌啶的混合物,N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合产物,1,2-二(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合产物以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6]);N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺,N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺,2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代-螺[4.5]癸烷,7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷与3-氯-1,2-环氧丙烷的反应产物。2.7 草酰胺,例如,4,4’-二辛氧基N,N’-草酰二苯胺,2,2’-二乙氧基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’-二-十二烷氧基-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’-二(3-二甲基氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2’-乙基-N,N’-草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁基-N,N’-草酰二苯胺的混合物及邻和对甲氧基二取代的N,N’-草酰二苯胺的混合物和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-羟基苯基)-1,3,5-三嗪,例如,2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-十三烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-[2-羟基-4-(2-羟基-3-丁氧基-丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪,2-[2-羟基-4-(2-羟基-3-辛基氧基-丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪,2-[4-十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基-苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-[2-羟基-4-(2-羟基-3-十二烷氧基-丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪,2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪,2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基-丙氧基)苯基]-1,3,5-***,2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪。3.金属减活化剂,例如,N,N’-二苯基草酰胺,N-水杨醛-N’-水杨酰肼,N,N’-二(水杨酰)肼,N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰)肼,3-水杨酰氨基-1,2,4-***,二(亚苄基)草酰二肼,N,N’-草酰二苯胺,异邻苯二甲酰二肼,癸二酰二苯基肼,N,N’-二乙酰己二酰二肼,N,N’-二(水杨酰)草酰二肼,N,N’-二(水杨酰)-硫代丙酰二肼。4.亚磷酸酯和膦酸酯,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(壬基苯基)酯,亚磷酸三月桂基酯,亚磷酸三(十八烷基)酯,二硬脂基季戊四醇二亚磷酸酯,三(2,4-二叔丁基苯基)亚磷酸酯,二异癸基季戊四醇二亚磷酸酯,二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯,二(2,6-二叔丁基-4-甲基苯基)-季戊四醇二亚磷酸酯,二异癸氧基季戊四醇二亚磷酸酯,二(2,4-二叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯,二(2,4,6-三叔丁基苯基)季戊四醇二亚磷酸酯,三硬脂酰山梨醇三亚磷酸酯,四(2,4-二叔丁基苯基)4,4’-二亚苯基二磷酸酯,6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧磷英(Phosphocin),6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧磷英,二(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯,二(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯。5.羟胺,例如,N,N-二苄基羟胺,N,N-二乙基羟胺,N,N-二辛基羟胺,N,N-二月桂基羟胺,N,N-双十四烷基羟胺,N,N-双十六烷基羟胺,N,N-双十八烷基羟胺,N-十六烷基-N-十八烷基羟胺,N-十七烷基-N-十八烷基羟胺,由氢化的脂胺衍生的N,N-二烷基羟胺。
6.硝酮,例如,N-苯甲基-α-苯基-硝酮,N-乙基-α-甲基硝酮,N-辛基-α-庚基硝酮,N-月桂基-α-十一烷基硝酮,N-十四烷基-α-十三烷基硝酮,N-十六烷基-α-十五烷基硝酮,N-十八烷基-α-十七烷基-硝酮,N-十六烷基-α-十七烷基-硝酮,N-十八烷基-α-十五烷基-硝酮,N-十七烷基-α-十七烷基-硝酮,N-十八烷基-α-十六烷基硝酮,由氢化脂胺衍生的N,N-二烷基羟胺衍生的硝酮。7.硫代增效剂,例如,二月桂基硫代二丙酸酯或二硬脂基硫代二丙酸酯。8.过氧化物清除剂,例如,β-硫代二丙酸的酯,如月桂基、硬脂基、肉豆寇基或十三烷基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫代氨基甲酸锌,双十八烷基二硫化物,季戊四醇四(β-十二烷基巯基)丙酸酯。9.聚酰胺稳定剂,例如,与碘化物和/或磷化合物组合的铜盐和二价锰盐。10.碱性辅助稳定剂,例如,三聚氰胺,聚乙烯吡咯烷酮,双氰胺,三烯丙基氰脲酸酯,脲衍生物,肼衍生物,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盐,如,硬脂酸钙,硬脂酸锌,山萮酸镁,硬脂酸镁,蓖麻酸钠和棕榈酸钾,焦儿茶酚酸锑(antimong Py-rocatecholate)或焦化茶酚酸锡。11.成核剂,例如,无机物如滑石,金属氧化物如二氧化钛或氧化镁,(优选)碱土金属的磷酸、碳酸或硫酸盐;有机化合物如单或多元羧酸及其盐,如4-叔丁基苯甲酸,己二醇,二苯基乙酸,琥珀酸钠或苯甲酸钠;聚合物如离子性共聚物(“离子聚合物”)。12.填充剂和增强剂,例如,碳酸钙,硅酸盐,玻璃纤维,玻璃球,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,木粉和其它天然产物的粉或纤维,合成纤维。13.其它添加剂,如增塑剂,润滑剂,乳化剂,色素,流变学中的添加剂,催化剂,流动控制剂,光学增亮剂,耐光剂,抗静电剂和发泡剂。14.苯并呋喃酮(benzofuranone)和二氢吲哚酮(indolinone),例如在美国专利432 5863,4338244,5175312,5216052,5252643,德国专利4316611,4316622,4316876,欧洲专利0589839或0591102中公开的那些化合物或3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二叔丁基-苯并呋喃-2-酮,5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮,3,3’-二[5,7-二叔丁基-3-(4-[2-羟基乙氧基]-苯基)苯并呋喃-2-酮],5,7-二叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮,3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基-苯并呋喃-2-酮,3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二叔丁基苯并呋喃-2-酮。
特别重要的是位阻胺的加入(上文中的2.6节),因为这些化合物给予改性聚合物特别有效的光稳定性。
如果添加剂是稳定剂,优选以0.05到5%重量比的总量加入。
在本发明的进一步具体实施方案中,除式(I)化合物外,也将其它稳定剂结合到聚合物中。特别感兴趣是另外结合位阻胺。依据是否使用含有乙烯式不饱和基团或另一个功能基的位阻胺,可通过共聚缩合或共聚加成或通过与含合适功能基的聚合物反应来进行结合。
含有烯式不饱和基团和适于本发明共聚合的们阻胺是,例如,美国专利3705166中描述的2,2,6,6-四甲基哌啶的丙烯酸和甲丙烯酸衍生物及其N-烷基和N-烷氧基衍生物。在美国专利4210612和欧洲专利0389420中也描述了四甲基哌啶的可共聚合衍生物。
可与功能性聚合物反应的位阻胺的实例是含有羟在的那些化合物,例如,2,2,6,6-四甲基-4-哌啶醇,1,2,2,6,6-五甲基-4-哌啶醇,1-羟乙基-2,2,6,6-四甲基-4-哌啶醇和美国专利4087404和欧洲专利0389419中所描述的化合物;或含有氨基的那些化合物,例如4-氨基-2,2,6,6-四甲基哌啶或美国专利3904581中描述的4-氨基哌啶。
可在式(I)的三嗪结合前、结合时或结合后进行这些位阻胺的结合。用于该目的的方法与三嗪的结合方法是相同的。详情还可从下文实施例中获得。
如果,除式(I)三嗪化合物之外,还要在聚合物中掺入位阻胺时,后者优选的使用量为改性的聚合物的0.1到15%重量比。在含有式Id单元的新的共聚物中使用相同的量。
可以聚合物的常用形式使用本发明的改性的聚合物,例如模具、管、片、膜、纤维、铸模树脂、粘合剂或涂料。他们优选用作表面涂料(加颜料和不加颜料均可)的粘合剂。
如上所述,式(I)或(Id)化合物和改性的聚合物还可被用作有机材料(主要为聚合物)的稳定剂。为此,所使用的改性的聚合物优选为至少含5%(例如5-50%)的结合形式的式(I)或(Id)化合物的那些。新的稳定剂的优选使用量为0.01到10%重量比,尤其0.5到5%重量比(基于被稳定的有机材料来计算)。新的化合物可被用于稳定有机材料,例如油、脂肪、蜡、化妆品、油漆或涂料,尤其是稳定有机聚合物。下列是可按该方法稳定的聚合物的实例:
1.单烯类和二烯类聚合物,例如聚丙烯,聚异丁烯,聚丁-1-烯,聚-4-甲基戊-1-烯,聚异戊二烯或聚丁二烯,以及环烯类聚合物,例如环戊烯或降冰片烯的聚合物,聚乙烯(它可交联也可不交联),例如高密度聚乙烯(HDPE),高密度高分子量聚乙烯(HDPE-HMW),高密度超高分子量聚乙烯(HDPE-UHMW),中密度聚乙烯(MDPE),低密度聚乙烯(LDPE),线状低密度聚乙烯(LLDPE),分支状低密度聚乙烯(NBLDPE)。
稀类聚合物,即在上段中例举的单烯类的聚合物,优选聚乙烯和聚丙烯,可通过不同方法,特别是通过下列方法来制备:
a)游离基聚合(通常在高压和升高的温度下)。
b)用催化剂催化聚合,催化剂通常含有一个或多个周期表中IVb、Vb,VIb或VIII族的金属。这些金属通常具有一个或多个配基,通常为氧化物,卤化物,醇化物,酯,醚,胺,烷基,烯基和/或芳基,他们可以π-或δ-配位。这些金属复合物可以是游离形式或固定在底物上,通常在活化的氯化镁,氯化钛(III),氧化铝或氧化硅上。这些催化剂在聚合介质中可以是溶解的或不溶的。在聚合中,可使用催化剂本身或者还可以使用其它活化剂,通常为金属烷基化物,金属氢化物,金属烷基卤化物,金属烷基氧化物或金属烷基噁烷化物,所述金属为周期表中Ia,IIa和/或IIIa族元素。该活化剂还可用酯,醚,胺或硅醚基团来进行常规的修饰。这些催化剂***通常称为Phillips,Standard Oil Indiana,Ziegler(-Nattal),TNZ(DuPont),金属茂或单位点催化剂(SSC)。2.在1)下所提及的聚合物的混合物,例如聚丙烯与聚异丁烯的混合物,聚丙烯和聚乙烯的混合物(如PP/HDPE,PP/LDPE)和不同类型聚乙烯的混合物(如LDPE/HDPE)。3.单烯烃和二烯烃相互共聚物或与其它乙烯单体的共聚物,例如,乙烯/丙烯共聚物,线状低密度聚乙烯(LLDPE)及其与低密度聚乙烯(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/乙酸乙烯酯共聚物及其与一氧化碳的共聚物或乙烯/丙烯酸共聚物及其盐(离子聚合物)以及乙烯与丙烯和二烯如己二烯,二环戊二烯或亚乙基-降冰片烯的三元共聚物。和这些共聚物的相互混合物和这些共聚物与上文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(EVA),LDPE/乙烯-丙烯酸共聚物(EAA),LLDPE/EVA,LLDPE/EAA和交替的或随机的聚烯烃/一氧化碳共聚物及其与其它聚合物如聚酰胺的混合物。4.烃类树脂(如C5-C9),包括其氢化的酸改性物(如粘合剂)和聚烯烃和淀粉的混合物。5.聚苯乙烯,聚(对甲基苯乙烯),聚(α-甲基苯乙烯)。6.苯乙类或α-甲基苯乙烯和二烯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/丁二烯/甲基丙烯酸烷基酯,苯乙烯/马来酐,苯乙烯/丙烯腈/丙烯酸甲酯;高冲击强度苯乙烯共聚物和另一种聚合物,例如聚丙烯酸酯,二烯聚合物或乙烯/丙烯/二烯三元共聚物的混合物,和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。7.苯乙烯或α-甲基苯乙烯接枝共聚物,例如,聚丁二烯上接苯乙烯,聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上接苯乙烯,聚丁二烯上接苯乙烯和丙烯腈(或甲丙烯腈);聚丁二烯上接苯乙烯、丙烯腈和甲丙烯酸甲酯,聚丁二烯上接苯乙烯和马来酸酐;聚丁二烯上接苯乙烯,丙烯腈和马来酸酐或马来酰亚胺;聚丁二烯上接苯乙烯和马来酰亚胺,聚丁二烯上接苯乙烯和丙烯酸或甲丙烯酸烷基酯;乙烯/丙烯/二烯三元聚合物上接苯乙烯和丙烯腈;聚丙烯酸烷基酯或聚甲丙烯酸烷基酯上接苯乙烯和丙烯腈;丙烯酸酯/丁二烯共聚物上接苯乙烯和丙烯腈,及其与6)下所列共聚物的混合物,例如,称为ABS,MBS,ASA或AES聚合物的共聚物混合物。8.含卤原子的聚合物,如聚氯戊二烯,氯化橡胶,异丁烯-异戊二烯的氯化或溴化共聚物(卤化丁基橡橡),氯化或氯磺化聚乙烯,乙烯和氯化乙烯的共聚物,表氯醇均聚物和共聚物,尤其含卤原子乙类化合物的聚合物,例如聚氯乙烯,聚偏二氯乙烯,聚氟乙烯,聚偏二氟乙烯,及其共聚物,如氯乙烯/偏二氯乙烯,氯乙烯/乙酸乙烯酯或偏二氯乙烯/乙酸乙烯酯共聚物。9.从α,β-不饱和酸及其衍生物衍生的聚和物,如聚丙烯酸酯和聚甲基丙烯酸酯;聚甲基丙烯酸甲酯,聚丙烯酰胺和聚丙烯腈,用丙烯酸丁酯冲击改性过。
10.在9)中提到的单体彼此或与其它不饱和单体的共聚物,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或丙烯腈/乙烯卤化物共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
11.从不饱和酸和胺或酰基衍生物或其缩醛衍生的聚合物,例如聚乙烯醇,聚乙酸乙烯酯,聚硬脂酸乙烯酯,聚苯甲酸乙烯酯,聚马来酸乙烯酯,聚乙烯醇缩丁醛,聚邻苯二甲酸烯丙酯或聚烯丙基蜜胺;及其与上述1)提到的烯烃的共聚物。12.环醚的均聚物和共聚物,如聚亚烷基二醇,聚环氧乙烷,聚环氧丙烷或其与二缩水甘油醚的共聚物。13.聚缩醛,如聚甲醛和含环氧乙烯作为共聚用单体的聚甲醛;用热塑的聚氨酯,丙烯酸酯或MBS改性的聚缩醛。14.聚苯氧和硫,及聚苯氧与苯乙烯聚合物或聚酰胺的混合物。15.由羟基结尾的聚醚,聚酯或聚丁二烯的一方脂肪或芳香聚异氰酸酯为另一方衍生的聚亚胺酯及其前体物。16.由二胺和二羧酸和/或由氨基羧酸或相应的内酰胺衍生的聚酰胺和共聚酰胺,例如,聚酰胺4,聚酰胺6,聚酰胺6/6,6/10,6/9,6/12,4/6,12/12,聚酰胺11,聚酰胺12,由间二甲苯二胺和己二酸起始的芳香聚酰胺;由六亚甲基二胺和间苯二酸和/或对苯二酸具有或没有高弹体作为改性剂制备的聚酰胺,例如,聚-2,4,4-三甲基六亚甲基对苯二酰胺或聚间亚苯基间苯二酰胺,以及前述聚酰胺与聚烯烃、烯烃共聚物、离子聚合物或化学键合的或接枝的高弹体形成的嵌段共聚物;或与聚醚,如与聚乙二醇,聚丙二醇或聚四亚甲基乙醇,及用EPDM或ABS改性的聚酰胺或共聚酰胺,和制备期间缩合的聚酰胺(RIM聚酰胺体系)。17.聚脲,聚酰亚胺,聚酰胺-酰亚胺,聚醚-酰亚胺,聚酯-酰亚胺,聚乙内酰脲(Polyhydantoin)和聚苯并咪唑。18.由二羧酸和二醇和/或由羟羧酸或相应的内酯衍生的聚酯,例如,聚对苯二甲酸乙二醇酯,聚对苯二甲酸丁二醇酯,聚-1,4-二甲醇己烷对苯二甲酸酯和聚羟基苯甲酸酯,以及由羟基结尾的聚醚衍生的嵌段共聚醚酯;和由聚碳酸酯或MBS改性的聚酯。19.聚碳酸酯和聚酯碳酸酯。20.聚砜,聚醚砜和聚醚酮。21.由醛为一方而酚、脲和三聚氰胺为另一方衍生的交联的聚合物,如苯酚/甲醛树脂,脲/甲醛树脂和三聚氰胺/甲醛树脂。22.干燥和非干燥聚酯树脂。23.由饱和和不饱和二羧酸与多元醇的共聚酯并以乙类化合物作为交联剂衍生的不饱和聚酯树脂,以及其含卤原子的低可燃性改性物。24.由取代的丙烯酸酯例如,环氧丙烯酸酯,衍生的可交联丙烯酸树脂,脲烷(Urethane)丙烯酸酯或聚酯丙烯酸酯。25.与三聚氰胺树脂、尿素树脂、异氰酸酯、异氰脲酸酯、聚异氰酸酯或环氧树脂交联的醇醛树脂、聚酯树脂和丙烯酸酯树脂。26.由脂族、环脂族、杂环或芳香缩水甘油基化合物衍生的交联环氧树脂,如双酚A和双酚F的缩水甘油基醚产物,在有或没有促进剂下,双酚A和双酚F与常规的硬化剂如酐或胺交联。27.天然聚合物如纤维素,橡胶,明胶及其化学改性的同系衍生物,例如,纤维素乙酸酯,纤维素丙酸酯和纤维素丁酸酯或纤维素醚如甲基纤维素;以及松香及其衍生物。28.前述聚合物的复合物(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及共聚物,PA/HDPE,PA/PP,PA/PPO,PBT/PC/ABS或PBT/PET/PC。
因此,本发明也涉及使有机材料对光线、氧和/或热损害稳定的方法,它包括向其中加入作为稳定剂的式(I)化合物或由式(Id)单体和需要时的其它单体构建的聚合物,并涉及将这些化合物用于稳定有机材料的用途。
所使用的稳定剂的量取决于被稳定的有机材料和被稳定材料的用途。通常,新的组合物中,每100份重量的被稳定材料含有0.01到15份重量的稳定剂,尤其是0.05到10份,特别是0.1到5份重量的稳定剂。
经加成来将新的化合物掺入有机材料,例如合成的有机材料,尤其是热塑性聚合物中,如果需要,还可通过本领域常规方法掺入添加剂。在成型前或成型期间迅速进行掺合,例如混合粉碎的成分或将稳定剂加到聚合物的熔液或溶液中,或将溶解或分散的化合物加到聚合物中,如果需要,随后蒸去溶剂。在高弹体情况下,这些化合物也可稳定晶格。将新的化合物掺入聚合物中的另一方法包括在相应单体聚合前或聚合期间或交联之前加入它们。
也可以母炼胶的形式,将新的化合物或其混合物加到被稳定的塑料中,该母炼胶例如以2.5到25%重量比的浓度含有这些化合物。
通过下列方法,可方便地掺入新的化合物:
—作为乳剂或分散液(如混入聚合物的晶格或乳剂)
—在附加成分或聚合物混合物混合期间作为干混合物加入
—直接加到制备装置中(如,挤压机,密闭式混合机等)。
—作为溶液或熔液。
以此方法获得的稳定的聚合物组合物可通过常规方法,如热压,喷丝,挤压或注塑转化为成型制品,如纤维、膜、狭带、片、夹心板、容器、管和其它外形。
所以,本发明还涉及将新的聚合物组合物用于生产成型制品。
在多层体系中的应用也是有益的。在这种情况下,将具有较高式(I)或含式(Id)单体和需要时的其它单体的聚合物的稳定剂含量,如5-15%(重量比)的新聚合物组合物以薄膜(10-100μm)涂于由含少量或不含式(I)或(Id)稳定剂的聚合物制成的成型制品上。可在制品成型的同时进行涂膜,例如同时挤压。然后,也可在待成形制品上进行涂膜,例如用膜层压或用溶液涂覆。外层或成品层具有UV过滤功能,可使制品内层防止UV光。外层优选含有5—15%重量比,尤其是5—10%重量比的至少一种式(I)或(Id)稳定剂。
用新的聚合物组合物生产多层体系因此也代表了本发明的另一主题,它的厚度为2—100μm的外层含有新的聚合物组合物,而内层却含少量或不含式(I)或(Id)稳定剂。
特别有意义的是,用组分A为聚碳酸酯的新聚合物组合物来生产多层体系。
以此方法稳定的聚合物具有杰出的高抗老化性,尤其是高抗UV光性能。因此,它们保持其机械特性及其色泽,甚至在户外长期使用时,也是如此。
该稳定剂也可以是两种或两种以上新化合物的混合物。稳定涂料组合物或有机材料的新的组合物除含式(I)或(Id)稳定剂外,也可含有其它稳定剂或其它添加剂,例如抗氧剂,其它光稳定剂,金属失活剂,亚磷酸酯或膦酸酯。其实例是上文所述的抗氧剂,光稳定剂及其它添加剂(3.—11.)。
下文实施例更详细地描述本发明的主题,但不表示对本发明的限制。在实施例中,份是重量份且%是重量%。如果在实施例中提及室温,其温度范围为20—25℃。这些定义用在各种飞速下,除非另有描述。直接跟在化学符号后的数表示化学式的指数,甚至不为下标时也如此。
使用下列缩写:THF 四氢呋喃AIBN α,α’-偶氮(二)异丁腈abs. 绝对(无不的)m.p. 熔点或熔解范围mmHg 托(1mmHg=133,322Pa)MALDI Matrix assisted Laser Desorption Ionization
(基质辅助激光解吸电离)MS 质谱NMR 核磁共振GC 气相色谱GPC 凝胶渗透色谱DSC 示差扫描量热法Mn 数均分子量(单位g/mol)Mw 重均分子量(单g/mol)Tg 玻璃化温度实施例1:在氮保护下,将14.2g(30mmol)2,4-二苯基-6-[2-羟基-4-(3-正丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪,3.5g(38mmol)丙烯酰氯和0.4g(5mmol)吡啶在100ml甲苯中的混合物在70℃加热24小时,加入4.5g(44mmol)三乙胺,并将混合物在70℃再加热6小时。冷却该混合物,并滤除固体残留物((CH3CH2)3N·HCl)。蒸发滤液,得到17.5g树脂状的粗品。柱色谱法(硅胶60;230-400目;洗脱液CH2Cl2/CH3OH 95/5)得到12.5g(产率79%)浅黄色树脂2,4-二苯基-6-[2-羟基-4-(3-正丁氧基-2-丙烯酰氧基丙氧基)苯基]-1,3,5-三嗪(化合物100)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。
C31H31N3O5(525.60)的元素分析:理论值: C:70.84 H:5.94 N:7.99%实测值 C:70.80 H:5.85 N:8.02%实施例2:在氮保护下,将14.2g(30mmol)2,4-二苯基-6-[2-羟基-4-(3-正丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪,8.0g(76mmol)甲基丙烯酰氯和0.4g(5mmol)吡啶在100ml甲苯中的混合物在80℃加热48小时。在旋转蒸发器上除去过量的甲基丙烯酰氯和甲苯。加入100ml甲苯和4.5g(44mmol)三乙胺,并将混合物在75℃加热5小时。冷却该混合物,滤除固体残留物((CH3CH2)3N·HCl)。蒸发滤液,得到18.4g粗品。柱色谱法(硅胶60;230—400目;直径8cm,h=30cm;洗脱液CH2Cl2)得到8.5g浅黄色树脂2,4-二苯基-6-[2-羟基-4-(3-正丁氧基-2-甲基丙烯酰氧基丙氧基)苯基]-1,3,5-三嗪(化合物101)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。
C32H33N3O5(539.63)的元素分析:理论值: C:71.22 H:6.16 N:7.79%实测值: C:70.42 H:6.28 N:7.57%实施例3的中间体:2-[2-羟基-4-(11-羟基-十一烷氧基)-苯基]-4,6-二苯基-1,3,5-三嗪。
在氮保护下进行本反应。
将170.7g(0.5mol)2-(2,4-二羟基苯基)-4,6-二苯基-1,3,5-三嗪、28.1g(0.5mol)粉状KOH(Flura,785%)在1000ml二甘醇二甲醚(Flura,99%)中的混合物在80℃加热。向该黄色溶液中加入155.4g(0.6mol)11-溴-1-十一烷醇(Flura,97%)。将该昆合物在100℃加热40小时,趁热滤除固体并将滤液冷却至0℃。滤出结晶固体,用己烷洗涤并在50℃/70mmHg下干燥。得到219.5g(产率85.84%)浅黄色固体2-[2-羟基-4-(11-羟基-十一烷氧基-)苯基]-4,6-二苯基-1,3,5-三嗪。F.131-132℃元素分析: C32H37N3O3 计算: C76.12 H7.29 N8.21
在氮保护下进行本反应。
向51.2g(0.1mol)2-[2-羟基-4-(11-羟基-十一烷氧基)-苯基]-4,6-二苯基]-1,3,5-三嗪,22.2g(0.2mol)三乙胺,500ml甲苯(Merck,99.5%)的混合物中,滴加13.3g(0.105mol)3-氯丙酰氯。滴加时间:在15—20℃20分钟。混合物变成白色悬浮液。滤除固体。用水洗涤溶液,用Na2SO4干燥并蒸发。通过Kieselgel 60过滤得到固体,并用甲苯洗脱。得到44.8g(产率79.2%)白色固体2-[2-羟基-4-(11-丙烯酰氧基-十一烷氧基)-苯基]-4,6-二苯基-1,3,5-三嗪(化合物102).F.123—125℃。分析:C35H39N3O4 计算:C:74.31 H:6.95 N:7.43
按实施例3所述方法制备标题化合物(化合物103);熔点94-96℃。实施例4b:2-[2-羟基-4-(3-乙烯苯甲氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪和2-[2-羟基-4-(4-乙烯苯氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪的混合物。
按实施例8b所述方法制备标题化合物(化合物105);熔点158—160℃。实施例4C:2-[2-羟基-4-(2-甲基丙烯酰氧基乙氧基)苯基]-4,6-二苯基-1,3,5-三嗪
按实施例3所述方法得到白色固体的标题化合物(化合物106)。
分析:C27H23N3O4(453.50)计算: C:71.57 H:5.11 N:9.27%实测: C:70.70 H:5.38 N:9.00%实施例5:2,4-双(2,4-二甲基苯基)-6-[2-羟基-4-(3-正丁氧基-2-甲基丙烯酰氧基丙氧基)苯基]-1,3,5-三嗪
按实施例2所述方法得到熔点为3℃的标题化合物(化合物400)。实施例6的中间体:2-[2-羟基-4-(11-羟基-十一烷氧基)苯基]-4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪
在氮保护下进行本反应。
将79.5g(0.2mol)2-(2,4-二羟基苯基)-4,6-(2,4-二甲基苯基)-1,3,5-三嗪,11.2g(0.2mol)粉状KOH(Flura,78.5%)在500ml二甘醇二甲醚(Flura,99%)中的混合物在80℃加热。向该黄色溶液中加入59.6g(0.23mol)11-溴-1-十一烷醇(Flura,97%)。将该混合物在100℃加热46小时。趁热滤除固体并将滤液冷却至0℃。滤出结晶,用己烷洗涤并在50℃/70mmHg下干燥。得到81.0g(产率71.4%)浅黄色固体2-[2-羟基-4-(11-羟基-十一烷氧基)苯基]-4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪。F.95-96℃。分析: C36H45N3O3 计算: C:76.16 H:7.99 N:7.40
(567.78) 实测: C:75.42 H:7.92 N:7.39实施例6:2-[2-羟基-4-(11-丙烯酰氧基-十一烷氧基)苯基]-4。6-双-(2,4-二甲基苯基)-1,3,5-三嗪(化合物401)。
在氮保护下进行本反应。
将56.8g(0.1mol)2-[2-羟基-4-(11-羟基-十一烷氧基)苯基]-4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪,12.4g(0.133mol)丙烯酰氯(Fluka,97%),0.4g氢醌(Fluka,98%),2.0ml吡啶在500ml甲苯(Merck,99.5%)中的混合物在80℃加热30小时。将溶液冷却至50℃并加入21.3ml(0.154mol)三乙胺,并在70℃加热6小时。滤除固体。除去溶剂并通过Kieselgel 60过滤黄色固体,并用甲苯洗脱。用异丙醇重结晶产物。得到47.0g(产率75.5%)白色固体2-[2-羟基-4-(11-丙烯酰氧基-十一烷氧基)苯基]-2,4-双-(2,4-二甲基苯基)-1,3,5-三嗪(化合物401);F.81-83℃。分析: C39H47N3O4 计算: C:75.33 H:7.62 N:6.76
(621.82) 实测: C:74.18 H:7.75 N:6.54实施例7:2,4-双(2,4-二甲基苯基)-6-[2-羟基-4-(11-甲基丙烯酰氧基十一烷氧基)-苯基]-1,3,5-三嗪
按实施例6所述方法得到熔点为71—73℃的标题化合物(化合物402)。实施例8a:2,4-双-(2,4-二甲基苯基)-6-[2-羟基-4-(2-甲基丙烯酰氧基乙氧基)苯基]-1,3,5-三嗪
按实施例3所述方法得到熔点为132—133℃的标题化合物(化合物404)。实施例8b:2-[2-羟基-4-(3-乙烯基苯甲氧基)-苯基-]-4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪和2-[2-羟基-4-(4-乙烯基苯甲氧基)-苯基-]4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪的混合物(405号化合物)。
在氮保护下进行本发应。
将19.9g(0.05mol)2-[2,4-二羟基-苯基]-4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪,8.4g(0.055mol)乙烯基苄基氯(Tluka,98%;异构体混合物:70%间位,30%对位),3.1g(0.55mol)氢氧化钾和100ml二甘醇二甲醚的混合物在100℃下加热3小时。冷却悬浮液,加入1升水,滤出固体并在异丙醇中重结晶。得到19.6g(产率76.3%)浅黄色固体2-[2-羟基-4-(3-/或4-乙烯基苯甲氧基)-苯基-]-2,4-双-(2,4-二甲基苯基)-1,3,5-三嗪(405号化合物);F.11O—114℃。分析: C34H31N3O2 计算值: C:79.51 H:6.08 N:8.18
(513.64) 实测值: C:79.53 H:5.98 N:7.98实施例9:在氮保护下,将5.0g(11mmol)2-苯基-4,6-双[2-羟基-4-(2-羟乙氧基)苯基]-1,3,5-三嗪,3.4g(33mmol)甲基丙烯酰氯和1.1g(14mmol)吡啶在35ml甲苯中的混合物在80℃下加热16小时。在60℃/60mmHg下,除去过量的甲基丙烯酰氯和甲苯。加入40ml甲苯和3.8g(38mmol)三乙胺,并将混合物在80℃下加热4小时。冷却混合物,滤除固体残留物。柱色谱法(硅胶60:230—400目;直径8cm,h=30cm;洗脱液:甲苯/乙酸乙酯1/1)得到3.84g粗品,用180ml乙酸乙酯重结晶,得到1.64g浅黄色固体2-苯基-4,6-双[2-羟基-4-(2-甲基丙烯酰氧基乙氧基)苯基]-1,3,5-三嗪(化合物201)(熔点:154—159℃)。
1H-NMR谱(CDCl3,300MHz)与所要求的产物一致。
C33H31N3O8(597.62)的元素分析:理论值: C:66.32 H:5.23 N:7.03%实测值: C:66.04 H:5.37 N:7.03%实施例10:在氮保护下,将12.79g(20mmol)2-苯基-4,6-双-[2-羟基-4-(3-正-丁氧基-2-羟丙氧基)苯基]-1,3,5-三嗪,4.3g(46mmol)丙烯酰氯和0.4g(5mmol)吡啶在80ml甲苯中的混合物在70℃下加热16小时。冷却至50℃并加入8.0g(80mmol)三乙胺后,将混合物在80℃下加热6小时。冷却该混合物,滤除固体残留物((CH3CH2)3N·HCl)。蒸发滤液,并将残留物溶解在200ml二氯甲烷中。通过硅胶层过滤该溶液(硅胶60;230—400目),并用450ml二氯甲烷洗脱。除去溶剂并在80℃干燥,得到8.8g(理论值的59%)橙色树脂2-苯基-4,6-双[2-羟基-4-(3-正-丁氧基-2-丙烯酰氧基丙氧基)苯基]-1,3,5-三嗪(化合物202)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。
C41H47N3O10(741.84)的元素分析:理论值: C:66.38 H:6.39 N:5.66%实测值: C:66.09 H:6.50 N:5.40%
实施例11和12起始化合物的制备:在氮保护下,将32.4g(128mmol)11-溴-1-十一烷醇在80℃下加到20.0g(54mmol)2-苯基-4,6-双(2,4-二羟基苯基)-1,3,5-三嗪,6.6g(109mmol)氢氧化钾和150ml二甘醇二甲醚的溶液中。将混合物在100℃加热14小时并趁热过滤,将滤液冷却至0℃。滤除其中结晶固体,压紧,在减压下(60mmHg,60℃)干燥24小时,得到27.6g(产率72%)熔点为126—135℃的浅黄色固体2-苯基-4,6-双[2-羟基-4-(11-羟基十一烷氧基)苯基]-1,3,5-三嗪。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。实施例11:在氮保护下,将10.8g(15mmol)2-苯基-4,6-双[2-羟基-4-(11-羟基十一烷氧基)苯基]-1,3,5-三嗪,3.6g(40mmol)丙烯酰氯,0.2g氢醌和0.3g(3.8mmol)吡啶在80ml甲苯中的混合物在78℃下加热16小时。在旋转蒸发器中除去过量的丙烯酰氯和甲苯。将残留物溶解在100ml甲苯中,加入16.2g(160mmol)三乙胺,并将混合物在80℃加热5小时。冷却该混合物,并滤除固体残留物(CH3CH2)3N·HCl)。蒸发滤液并溶解在50ml二氯甲烷中。通过硅胶(硅胶60;230—400目,直径6cm,h=4cm)过滤该溶液,并用400ml二氯甲烷洗脱,除去溶剂并且残留物干燥2小时后(80℃/0.1mmHg),得到10.7g(产率86%)浅黄色固体2-苯基-4,6-双[2-羟基-4-(11-丙烯酰氧基十一烷氧基)苯基]-1,3,5-三嗪(化合物203)(熔点93.3℃,用DSC测定)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。实施例12:在氮保护下,将10.8g(15mmol)2-苯基-4,6-双[2-羟基-4-(11-羟基十一烷氧基)苯基]-1,3,5-三嗪,4.0g(38mmol)甲基丙烯酰氯,0.2g氢醌和0.3g(3.8mmol)在80ml甲苯中的混合物在80℃加热16小时。在旋转蒸发器上除去过量的甲基丙烯酰氯和甲苯。将残留物溶解在100ml甲苯中,加入8.1g(80mmol)三乙胺和0.1g氢醌,并将该混合物在70℃加热4小时。冷却混合物,滤除固体残留物((CH3CH2)3N·HCl)。蒸发滤液并溶解在50ml二氯甲烷中。通过硅胶(硅胶60;230—400目;直径6cm,h=4cm)过滤该溶液并用400ml二氯甲烷洗脱,除去溶剂并将残留物干燥2小时(80℃/0.1mmHg)后,得到10.9g(产率85%)浅黄色固体2-苯基-4,6-双[2-羟基-4-(11-甲基丙烯酰氧基十一烷氧基)苯基]-1,3,5-三嗪(熔点68.3℃,用DSC测定)。
1II NMR谱(CDCl3,300MHZ)与所要求产物一致。实施例13:按实施例11所述方法制备化合物(205)Tg=17℃。分析:C41H47N3O8 计算值: C:69.37 H:6.67 N:5.92%
(709.84) 实测值: C:68.54 H:6.67 N:6.03%实施例14:按实施例11所述方法制备化合物(206)Tg=15℃。分析:C39H43N3O8 计算值: C:68.71 H:6.36 N:6.16%
(681.79) 实测值: C:68.65 H:6.44 N:6.49%实施例15的中间物:2-苯基-4-(2-羟基-4-正-己氧基-苯基)-6-[2-羟基-4-(11-羟基-十一烷氧基)苯基]-1,3,5-三嗪。
在氮保护下进行反应。
将37.3g 2-苯基-4,6-双-(2,4-二羟基-苯基)-1,3,5-三嗪(0.100mol),6.6g粉状KOH(Fluka,>85%,0.100mol),25.9g11-溴-1-十一烷醇(Fluka,97%,0.103mol)和0.6g(3.6mmol)碘化钾(Merck,99.5%)在160ml二甘醇二甲酯(Diglyme,Fluka,99%)中的混合物在搅拌下,在110℃加热4小时30分钟。冷却至50℃后,加入6.6g(0.100mol)粉状KOH(Fluka,>85%)和17.0g(0.103mol)正溴己烷(Fluka,98%)。将混合物在搅拌下在105℃加热14小时。趁热过滤该混合物并蒸发滤液(旋转蒸发)。所得产物经过柱色谱法处理[Kieselgel 60,230—400目;10cm直径;h=30cm;洗脱液CH2Cl2]最初洗脱的流份为二己基衍生物,第二个洗脱的为所要求的标题产物而第三个洗脱流份为由两组11-羟基-十一烷基二烷基化的产物。
在60℃/60mmHg下干燥24小时后,得到22.5g浅黄色固体2-苯基-4-(2-羟基-4-正己氧基-苯基)-6-[2-羟基-4-(11-羟基-十一烷氧基)-苯基]-1,3,5-三嗪,F.96—99℃。
1H-NMR(CDCl3,300MHz)谱与所要求产物一致。分析C38H49N3O5 计值值:C:72.70 H:7.87 N:6.69%
(627.83) 实测值:C:72.19 H:8.01 N:6.88%实施例15:2-苯基-4-(2-羟基-4-正己氧基-苯基)-6-[2-羟基-4-(11-甲基丙烯酰基氧基十一烷氧基)苯基]-1,3,5-三嗪(化合物207)。
在氮保护下进行该反应。
将22.0g(35.0mmol)2-苯基-4-(2-羟基-4-正己氧基-苯基)-6-[2-羟基-4-(11-羟基-十一烷氧基)苯基]-1,3,5-三嗪,4.4g(42.0mmol)甲基丙烯酰氯(Fluka,97%),0.5g(6.3m-mol)吡啶在100ml甲苯(Merck,99.5%)中的混和物在80—85℃下加热21小时。冷却至55℃后,加入8.9g(87.5mmol)三乙胺(Fluka,99.5%)。将混合物在80℃再加热7小时趁热过滤。蒸发滤液。将粗品(25.7g)溶解在120ml CH2Cl2中,通过Kieselgel 60过滤(230、400目,6.5cm直径;h=5cm)并用380ml CH2Cl2洗脱。除去溶剂并在80℃/0.1mmHg下干燥2小时30分,得到22.3g(产率91.4%)橙色树脂2-苯基-4-(2-羟基-4-己氧基苯基)-6-[2-羟基-4-(11-甲基丙烯酰基氧基十一烷氧基)-苯基]-1,3,5-三嗪,Tg=-13℃(DSC)。
1H-NMR(CDCl3,300MHz)谱与所要求产物一致。分析:C42H53N3O6 计算值: C:72.49 H:7.68 N:6.04%
(695.90) 实施值: C:72.14 H:7.48 N:5.98%实施例16:2-苯基-4-[2-羟基-4-(11-乙酰氧基-十一烷氧基)苯基]-6-[2-羟基-4-(11-甲基丙烯酰氧基-十一烷氧基)苯基]-1,3,5-三嗪(化合物208)。
在氮保护下进行该反应。
将20.0g(28.0mmol)2-苯基-4,6-双-[2-羟基-4-(11-羟基-十一烷氧基)苯基]-1,3,5-三嗪(实施例11和12的中间体),3.1g(29.4mmol)甲基丙烯酰氯(Fluka,97%),0.2g氢醌(Fluka,98%),0.3g(3.8mmol)吡啶在115ml甲苯中的混合物在第一步反应中于80℃搅拌下加热5小时,然后冷却至60℃,加入4.62g(58.8mmol)乙酰氯并在60℃再加热18小时。分出溶剂和过量的乙酰氯后(旋转蒸发),将残留物溶解在100ml甲苯中。加入7.1g(70mmol)三乙胺并在搅拌下,在70℃加热6小时。冷却后,滤除固体([H5C2]3N·HCl)并将滤液浓缩至干。将粗品溶解在100ml CH2Cl2中,通过Kieselgel 60层(230—400目)过滤并用100ml CH2Cl2/甲醇混合物(95∶5)洗脱。分出溶剂并在40℃/60mmHg下干燥48小时,得到20.8g(90.1%产率)黄色固体化合物(208),F.70—76℃。实施例17:在氮保护下,将7.0g(14.1mmol)2-(4-氯苯基)-4,6-双[2-羟基-4-(2-羟基乙氧基)苯基]-1,3,5-三嗪,8.52g(94.1mmol)丙烯酰氯和0.3g(3.8mmol)吡啶在180ml甲苯中的混合物在75℃下加热14小时。在旋转蒸发器上除去过量的丙烯酰氯和甲苯。加入100ml甲苯和5.0g(48mmol)三乙胺后,将混合物在90℃加热14小时。冷却该混合物,并滤除固体残留物((CH3CH2)3N·HCl)。蒸发滤液并用乙酸乙酯重结晶,得到4.4g(产率52%)浅黄色固体2-(4-氯苯基)-4,6-双[2-羟基-4-(2-丙烯酰氧基乙氧基)苯基]-1,3,5-三嗪(化合物200)(熔点115—120℃)
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。
C31H26ClN3O8(604.02)元素分析:理论值: C:61.64 H:4.34 N:6.96 Cl:5.87%实测值: C:61.36 H:4.49 N:6.98 Cl:6.02%实施例18—22b的中间体:
(i)2-基-4,6-二氯-1,3,5,-三嗪
将109.5g(0.55mol)2-溴代(纯度98%)的150ml abs THF(纯度99.5%)溶液在氮保护下,经过1.5小时加到搅拌的、保持在60℃的14.6g(0.6mol)镁屑(纯度99.8%)在已先加入碘结晶的100ml abs THF中的悬浮液中。随后将该混合物保持在回流温度(68℃)30分钟。
冷却后,将产生的格氏试剂转移到滴液漏斗中并滴加到96.0g(0.52mol)氰尿酰氯(98%)的270ml THF溶液中。滴加过程中(共用1.5小时),通过冷却保持温度在15—30℃。随后将混合物在25℃下搅拌2小时,并倾入含80ml 32%HCl(0.81mol)的2升的冰/水混合液中。将该混合液搅拌1小时并过滤。将滤饼悬浮在100ml水中,搅拌30分钟并再过滤。该操作重复两次。在25℃和60mmHg压力(8000Pa)下,滤饼在P2O5上干燥24小时。接着将171.0g粗品溶解在甲苯中,趁热过滤并通过加入己烷并冷却至0℃来结晶。过滤并干燥得到82.8g标题产物(i),熔点85—91℃。
1H-NMR(CDCl3,300MHz):δ2.22(S,6H);2.32(S,3H);6.95(S,2H)。
(ii)2-基-4,6-双(2,4-二羟基苯基)-1,3,5-三嗪。
将148.7g(1.21mol)无水三氯化铝(纯度98%)在搅拌下加到130.0g(0.485mol)2-基-4,6-二氯-1,3,5-三嗪(i)在300ml沸点范围为110—140℃的石油醚和385ml四氢噻吩砜形成的悬浮液中。加入过程中,混合物升温至45℃。在45分钟内,将133.5g(1.21mol)间苯二酚(纯度98%)的150ml四氢噻吩砜溶液加到该混合物中。该混合物在80—85℃温热5小时30分并放出HCl。除去上相(石油醚),并将下面粘稠相趁热转移到搅拌的2.1升甲醇和2.1升水的混合液中。将混合液搅拌14小时后,滤除固体,在2.2升1摩尔HCl中搅拌1小时并再过滤。将滤饼悬浮在1000ml水中,搅拌30分钟再过滤。该操作重复两次。在80℃和60mmHg压力(8000Pa)下,将滤饼干燥24小时,得到170.5g标题产物,其结构式为:熔点:230—234℃。实施例18:按实施例10所述方法制备化合物(500),得到黄色树脂,Tg:9℃。分析: 计算: C 67.42 H 6.81 N 5.36%(C44H53N3O10):(783.92) 实测: C 67.27 H 6.91 N 5.66%实施例19:按实施例10所述方法制备化合物(501),得到黄色树脂,Tg:-2℃。分析: 计算: C 68.04 H 7.08 N 5.18%(C46H57N3O10):(811.98) 实测: C 68.01 H 7.10 N 4.92%实施例20:按实施例12所述方法制备化合物(502),得到树脂。分析: 计算: C 72.70 H 8.25 N 4.71%(C54H73N3O8):(892.19)
实测: C 71.69 H 8.09 N 4.75%实施例21:按实施例9和11所述方法制备化合物(503),得到黄色树脂,Tg:22℃。分析: 计算: C 70.28 H 7.11 N 5.59%(C44H53N3O8):(751.92) 实测: C 69.81 H 6.87 N 5.67%实施例22和22b的中间体:2-基-4-(2-羟基-4-正己氧基-苯基)-6-(2-羟基-4-(11-羟基-十一烷氧基)苯基]-1,3,5-三嗪。
在氮保护下进行该反应。
将83.0g(0.200mmol)2-基-4,6-双-(2,4-二羟基-苯基)-1,3,5-三嗪,13.2g(0.200mol)粉状KOH(Fluka,>85%),51.8g(0.206mol)11-溴-1-十一烷醇(Fluka,97%)和1.2g(7.2mmol)碘化钾(Merck,99.5%)在300ml二甘醇二甲醚(Diglyme,Fluka,99%)中的混合物在搅拌下于120℃加热3小时。冷却至60℃后,加入13.2g粉状KOH和34.0g正溴己烷(0.206mol,Fluka,98%)。将混合物在搅拌下在110℃加热16小时。趁热过滤该混合物并蒸发滤液(旋转蒸发)。所得产物(152.1g)经过柱色谱处理[Kieselgel 60;230—400目;10cm直径;h=30cm;洗脱液:甲苯/甲醇98∶2]从第二个流份中分出产物。第一洗脱流份为二己基衍生物,第二洗脱馏分为所要求的产物并且第三馏分为用两组11-羟基-十一烷基二烷基化的产物。
在110℃/0.1mmHg下干燥2小时后,得到55.2g(产率41.2%)在25℃缓慢结晶的黄色树脂2-基-4-(2-羟基-4-正己氧基-苯基)-6-[2-羟基-4-(11-羟基-十一烷氧基)-苯基]-1,3,5-三嗪。
1H-NMR(CDCl3,300MHz)谱与所要求产物一致。分析(C41H55N3O5): 计算:C:73.51 H:8.27 N:6.27%
(669.91) 实测:C:73.55 H:8.47 N:6.29%实施例22:2-基-4-(2-羟基-4-正己氧基苯基)-6-[2-羟基-4-(11-甲基丙烯酰氧基-十一烷氧基)-苯基]-1,3,5-三嗪(化合物504)。
在氮保护下进行本反应。
将10.9g(16.0mmol)2-基-4-(2-羟基-4-正己氧基苯基)-6-[2-羟基-4-(11-羟基-十一烷氧基)-苯基]-1,3,5-三嗪,2.0g(19.2mmol)甲基丙烯酰氯(Fluka,97%)和0.4g(5.0mmol)吡啶在70ml甲苯(Merck,99.5%)中的混合物在80—85℃加热16小时。冷却至55℃后,加入4.1g(40.0mmol)三乙胺(Fluka,99.5%)。将该混合物在80℃再加热6小时并趁热过滤。蒸发滤液。将粗品(13.6g)溶解在100ml CH2Cl2中,通过Kieselgel 60(230—400目)柱(6.5cm直径;h=4cm)并用380ml CH2Cl2洗脱。除去溶剂并在80℃/0.1mmHg下干燥2小时30分,得到22.3g(产率91.4%)黄色树脂2-基-4-(2-羟基-4-己氧基苯基)-6-[2-羟基-4-(11-甲基丙烯酰氧基-十一烷氧基)-苯基]-1,3,5-三嗪(化合物504),Tg:-10℃(DSC)。
1H-NMR(CDCl3,300MHz)谱与所要求产物一致。分析(C45H59N3O6):计算: C:73.24 H:8.06 N:5.69%
(737.98) 实测: C:73.01 H:7.76 N:5.61%实施例22a:按实施例8b所述方法制备化合物(505)得到橙色树脂,Tg:13.3℃(DSC)。分析(C42H37N3O4):计算: C:77.88 H:5.76 N:6.49%
(647.78) 实测: C:77.64 H:5.76 N:5.66%实施例22b:2-基-4-(2-羟基-4-正己氧基苯基)-6-[2-羟基-4-(11-丙烯酰氧基-十一烷氧基)-苯基]-1,3,5-三嗪(化合物506)
在氮保护下进行本反应。
将27.3g(40.8mmol)2-基-4-(2-羟基-4-正己氧基苯基)-6-[2-羟基-4-(11-羟基-十一烷氧基)-苯基]-1,3,5-三嗪,4.4g(49.0mmol)丙烯酰氯(Fluka,97%),0.1g(0.9mmol)氢醌(Fluka,99%)和0.75g(9.5mmol)吡啶的搅拌下在170ml甲苯(Merck,99.5%)中的混合物在70—75℃加热17小时。冷却至50℃后,加入20.0g(197.6mmol)三乙胺(Fluka,99.5%)。将该混合物在85℃再加热6小时并趁热过滤。蒸发滤液。将粗品溶解在100ml甲苯/甲醇(98∶2)中,通过Kieselgel 60(230—400目筛)柱(6.5cm直径;h=5cm)过滤并用400ml甲苯/甲醇(98∶2)洗脱。除去溶剂并在80℃/0.1mmHg下干燥3小时,得到24.3g(产率82.3%)黄色树脂。
2-基-4-(2-羟基-4-己氧基苯基)-6-[2-羟基-4-(11-丙烯酰氧基-十一烷氧基)苯基]-1,3,5-三嗪(化合物506);Tg:-14.2℃(DSC)。
1H-NMR(CDCl3,300MHz)谱与所要求产物一致。分析C44H57N3O6: 计算: C:73.00 H:7.94 N.5.80%
(723.96) 实测: C:72.81 H:7.70 N:5.53%实施例23:在氮保护下,将15.9g(20mmol(2,4,6-三[2-羟基-4-(3-正丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪,7.3g(80mmol)丙烯酰氯和0.4g(5mmol)吡啶在120ml甲苯中的混合物在75℃搅拌下加热24小时。在旋转蒸发器上除去过量丙烯酰氯和甲苯。将残留物溶解在100ml甲苯中,加入10.1g(100mmol)三乙胺,并将混合物在80℃下搅拌6小时。冷却该混合物,并滤除固体残留物((CH3CH2)2N·HCl)。蒸发滤液并溶解在100ml二氯甲烷中。通过硅胶层(硅胶60;230—400目;直径10cm,h=5cm)过滤溶液并用2000ml二氯甲烷洗脱,除去溶剂并将残留物干燥(90℃/0.5mmHg)后,得到12.0g(产率63%)浅黄色树脂2,4,6-三[2-羟基-4-(3-正丁氧基-2-丙烯酰氧基丙氧基)苯基]-1,3,5-三嗪(化合物300)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。
C51H63N3O15(958.07)的元素分析:理论值: C:63.94 H:6.63 N:4.39%实测值: C:63.24 H:6.57 N:4.02%实施例24和25起始化合物的制备:在氮保护下,将42.9g(170mmol)11-溴-1-十一烷醇在80℃下加到20.3g(50mmol)2,4,6-三(2,4-二羟基苯基)-1,3,5-三嗪、9.3g(141mmol)氢氧化钾和150ml二甘醇二甲醚的溶液中。将该混合物在100℃加热16小时并趁热过滤,并将滤液冷却至0℃。滤除结晶固体,压紧,在减压下(60mmHg,70℃)干燥48小时,得到24.3g(产率53%)浅黄色树脂状固体2,4,6-三[2-羟基-4-(11-羟基十一烷氧基)苯基]-1,3,5-三嗪。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。实施例24:在氮保护下,将10.1g(11mmol)2,4,6-三[2-羟基-4-(11-羟基十一烷氧基)苯基]-1,3,5-三嗪,3.6g(40mmol)丙烯酰氯,0.2g氢醌和0.3g(3.8mmol)吡啶在80ml甲苯中的混合物在80℃加热18小时。在旋转蒸发器上除去过量的丙烯酰氯和甲苯。将残留物溶解在100ml甲苯中,加入16.2g(160mmol)三乙胺和0.1g氢醌,将混合物在78℃下搅拌5小时。冷却该混合物,并滤除固体残留物((CH3CH2)3N·HCl)。蒸发滤液并溶解在100ml二氯甲烷中。通过硅胶层(硅胶60;230—400目;直径6cm;h=4cm)过滤该溶液并用400ml二氯甲烷洗脱,除去溶剂并将残留物干燥2小时(70℃/0.1mmHg)后,得到7.7g(产率65%)浅黄色固体2,4,6-三[2-羟基-4-(11-丙烯酰氧基十一烷氧基)苯基]-1,3,5-三嗪(化合物301)(熔点72.8℃,用DSC测定)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。实施例25:在氮保护下,将10.1g(11mmol)2,4,6-三[2-羟基-4-(11-羟基十一烷氧基)苯基]-1,3,5-三嗪,4.2g(40mmol)甲基丙烯酰氯,0.2g氢醌和0.3g(3.8mmol)吡啶在80ml甲苯中的混合物在80℃加热18小时。在旋转蒸发器上除去过量的甲基丙烯酰氯和甲苯。将残留物溶解在100ml甲苯中,加入8.1g(80mmol)三乙胺和0.1g氢醌,并将混合物在70℃下搅拌5小时。冷却该混合物,并除去固体残留物。蒸发滤液并溶解在100ml二氯甲烷中。通过硅胶层(硅胶60;230—400目;直径6cm;h=4cm)过滤该溶液并用400ml二氯甲烷洗脱,除去溶剂并将残留物干燥2小时(70℃/0.1mmHg)后,得到7.7g(产率65%)浅黄色固体2,4,6-三[2-羟基-4-(11-甲基丙烯酰氧基十一烷氧基)苯基]-1,3,5-三嗪(化合物302)(熔点60.2℃,用DSC测定)。
1H-NMR谱(CDCl3,300MHz)与所要求产物一致。实施例28:2-苯基-4-(2-羟基-4-己氧基苯基)-6-[2-羟基-4-(11-甲基丙烯酰氧基十一烷氧基)苯基]-1,3,5-三嗪的均聚物(化合物602)。
在100ml三颈烧瓶中。在氩气保护下,用40mg(0.22mmol)α,α’-偶氮二异丁腈(AIBN,Fluka,98%)和70mg(0.75mmol)正丁基硫醇(Fluka,97%)处理5.2g(7.5mmol)2-(苯基)-4-(2-羟基-4-己氧基苯基)-6-(2-羟基-11-甲基丙烯酰氧基十一烷氧基苯基)-1,3,5-三嗪(化合物207)的40ml甲苯(Fluka,99.5%)溶液。
将混合物在搅拌下保持85℃16小时。冷却后,将净黄色溶液在搅拌下滴加到400ml乙腈中(Fluka,99.5%)。
将沉淀物倾析出来并溶解在30ml甲苯中。除去溶剂并在80℃/0.1mmHg下干燥2小时,得到3.35g(64%)标题产物(化合物602);Tg:29.9℃。
1H-NMR(CDCl3,300MHz)谱与所要求产物一致(无乙烯基-H信号)。
MALDI—MS Mn=1698
Mw=3251实施例29:2-苯基-4-(2-羟基-4-己氧基苯基)-[2-羟基-4-(11-甲基丙烯酰氧基十一烷氧基)苯基]-1,3,5-三嗪和丙烯酸正丁基酯以摩尔比为1∶4的共聚物。
在100ml三颈烧瓶中,在氩气保护下,用200mg(1.12mmol)α,α’-偶氮二异丁腈(AIBN,Fluka,98%)和300mg(3.75mmol)正丁基硫醇(Fluka,97%)处理5.2g(7.5mmol)2-苯基-4-(2-羟基-4-己氧基苯基)-6-(2-羟基-11-甲基丙烯酰氧基十一烷氧基苯基)-1,3,5-三嗪(化合物207)和3.8g(30mmol)丙烯酸正丁基酯(Fluka,99%)的40ml甲苯(Fluka,99.5%)溶液。
将该混合物在搅拌下保持85℃17小时。冷却后,将净黄色溶液在搅拌下滴加到400ml乙腈(Fluka,99.5%)中。
倾析出沉淀物并溶解在30ml甲苯中;过滤除去固体杂质。除去溶剂并在80℃/0.1mmHg下干燥2小时,得到6.60g(73%)标题产物(化合物603);Tg:-3.5℃。
MALDI—MS Mn=2905
Mw=4199实施例30:按实施例28所述方法制备化合物(604),得到桔黄色树脂Tg=49.8℃。
[C45H59N3O6](737.98)计算: C:73.24 H:8.06 H:5.69%实测: C:72.57 H:8.43 N:5.49%
Mn=1920
Mw=4198(MALDI—MS)实施例31:按实施例29所述方法制备化合物(605),得到橙色树脂,Tg=-4.2℃。[C45H59N3O6],[C7H12O2]4计算: C:70.11 H:8.62 N:3.36%实测: C:70.71 H:8.74 N:3.67%
Mn=3238
Mw=4923(MALDI—MS)实施例31a:按实施例29所述方法制备化合物(606),但用30mmol甲基丙烯正十二烷基酯代替丙烯正丁基酯;Tg,-33.4℃。
MALDI—MS Mn=2023
Mw=3661实施例32:按实施例28所述方法制备化合物(607),得到白色固体:
[C35H39N3O4](565.71)计算: C:74.31 H:6.95 N:7.43%实测: C:74.13 H:7.16 N:7.27%
Mn=1938
Mw=3054(MALDI—MS)实施例33:按实施例29所述方法制备化合物(608)
[C35H39N3O4][C7H12O2]4计算: C:70.17 H:8.13 N:3.90%实测: C:70.70 H:8.33 N:4.60%
Mn=2310
Mw=3341(MALDI—MS)实施例34:按实施例28所述方法制备化合物(609),得到黄色树脂。
[C40H49N3O4](635.85)计算: C:75.56 H:7.77 N:6.61%实测: C:74.02 H:8.06 N:6.06%
Mn=1781
Mw=3669(MALDI—MS)实施例35:按实施例29所述方法制备化合物(610),但仅用一半量的丙烯酸正丁基酯。
[C40H49N3O4]、[C7H12O2]2计算: C:72.70 H:8.25 N:4.71%实测: C:71.81 H:8.41 N:4.68%
Mn=1908
Mw=3111(GPC)实施例36:按实施例28所述方法制备化合物(611),得到熔点为85.7℃(DSC)的黄色固体。
[C36H41N3O4](579.74)计算: C:74.58 H:7.13 N:7.25%实测: C:73.90 H:7.15 N:7.03%
Mn=2405
Mw=3701(MALDI—MS)实施例37:按实施例35所述方法制备化合物(612),得到黄色树脂,Tg=15.8℃。
[C36H41N3O4],[C7H12O2]2计算: C:71.83 H:7.84 N:5.03%实测: C:71.71 H:7.61 N:5.19%
Mn=3241
Mw=4920(MALDI—MS)实施例38:按实施例28所述方法制备化合物(613),得到黄色固体,Tg=59.1℃。
[C36H41N3O5](595.74)计算: C:72.58 H:6.94 N:7.05%实测: C:72.25 H:6.95 N:6.63%
Mn=2405
Mw=5533(MALDI—MS)实施例39:按实施例35所述方法制备化合物(614),得到橙色树脂,Tg=35.7℃。
[C36H41N3O5],[C7H12O2)2计算: C:70.48 H:7.69 N:4.93%实测: C:70.61 H:7.76 N:5.35%
Mn=3612
Mw=5264(MALDI—MS)实施例40:按实施例35所述方法制备化合物(615),Tg=66.5℃。
Mn=2111
Mw=3174(MALDI—MS)实施例41:按实施例35所述方法制备化合物(616),Tg=59.8℃
[C34H31N3O2],[C7H12O2]2
Mn=2223
Mw=3634(MALDI—MS)实施例42:甲基丙烯酸甲酯和化合物(103)的共聚物
按下列方法将甲基丙烯酸甲酯与1%重量的化合物103聚合:
通过在60℃加热,将70.0g甲基丙烯酸甲酯,0.7g化合物(103)和0.07g月桂酰基过氧化物的混合物预先聚合成糖浆状,仍然可以铸型的稠度。将共聚物注入模子12个玻璃盘160×210×6mm,PVC线d=1.5mm,6个金属夹子)中,在60℃水浴中聚合6小时。最后在循环空气中,在120℃固化3小时。得到约1.5mm厚的盘。
将0.3g生成的改性聚甲基丙烯酸甲酯(PMMA)溶解在CHCl3(溶液I;0.06g PMMA/L)中,测定UV谱。随后,通过加入甲醇来沉淀该聚合物,滤出沉淀,干燥并重新溶解在CHCl3(溶液II;0.04g PP-MA/L)中,也记录溶液II的UV谱。
基于单体的分子量,计算342nm处的摩尔消光系数:
溶液I: E342=20700
溶液II:E342=22200
两溶液的恒定消光系数显示,单体(103)已并入聚合物。实施例43:甲基丙烯酸甲酯和化合物(402)的共聚物
按实施例42所述方法,将甲基丙烯酸甲酯与1%重量的化合物402聚合。按实施例42所述,研究所得到的聚合物样品中单体的掺入情况。从UV谱计算下列数据:
溶液I.E339=21600
溶液II:E339=22200
两种溶液的恒定消光系数显示,单体(402)已并入聚合物中。B)应用实施例B1:改性PMMA
将5g实施例42和43得到的改性聚甲基丙烯酸甲酯(分别含1%的共聚稳定剂[103]和[402])在室温下溶解在30g二氯甲烷中。从该溶液后玻璃板上施以薄膜,蒸发掉溶剂并在真空干燥后,这些薄膜厚30μm。为了进行比较,从未稳定化的聚甲基丙烯酸甲酯(Plex8704,Romh & Haas,AG)中制备类似的薄膜。
将薄膜从玻璃板上揭下并夹在卡纸板(6×3cm)上。在UV曝光装置上,用安放在样品上方20cm处的5TL/09荧光灯和5TL/12灯(波长范围295—400nm)照射这些样品。通过测定泛黄度指数(Yel-lowness Index)(YI,Method ASTM D1925),在一定时间间隔检查样品的退色。表1显示其结果。
表1:含1%共聚形式稳定剂的PMMA的YI
YI稳定剂 前 照射
无 -0.8化合物(103) 3.8化合物(402) 3.2
本发明稳定剂实际上不引起底物退色。实施例B6:将新的UV吸收剂(化合物(202),(600)和(601)]预先溶解在约5—10g二甲苯中并混合到含有下列成分的清漆中:
Uracron 2263×B(50%)1) 54.5
Cymel327(90%)2) 16.3
丁基乙二醇乙酸酯 5.5
二甲苯 19.4
正丁醇 3.3
BaysilonA(1%二甲苯液)3) 1
100.0
1)丙烯酸酯树脂(DSM,NL)
2)密胺树脂(American Cyanamid,USA)
3)流量控制剂(Bayer,D)
按本方法,用丁基乙二醇乙酸酯/正丁醇/二甲苯(1/6/13)将如此制备的清漆稀释到可喷涂的稠度并施用于备好的底物上(用铝片包着的线圈,自动填充器,银金属基包衣)。干燥约15分钟后,将涂层在130℃烘30分钟,得到厚度约为40—45μm的干燥薄膜。
所用对照物为用同样方法制备但不含UV吸收剂的清漆。
在UVCONR装置中(Atlas Corp.)将样品风干(UVB—313灯,周期:8h UV,70℃;4h Cond,50℃)。
测定20°下的光泽(DIN 67530)。稳定化样品比未稳定化对照样品显示更好的光泽保留性能。
Claims (19)
其中,E1和E2彼此独立为通式Ia或Ib的基团
其中
A为C-(=O)-CR5=CH-R6;
R1为-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2或-C(=O)-O-CH2-C(=CH2)-R10;及当R3’为-O-R8R8’-(CH2)L-XA时,R1还可为C1-C18烷基或中间有-O-、-CO-O-或-O-CO-的C3-C20的烷基;及当E1为通式Ia基团,其中R2和R14都不是氢时,R1还可为-A,-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-XA,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CHX-OA及-CR8R8’-(CH2)L-C(C=O)-XA;及,当E1为式Ib基团时,R1还可为-CH2-CH(XA)-CH2-O-R7;
R2彼此独立为H,C1-C12烷基,环己基,C3-C6链烯基,卤素,苯基或三氟甲基;
R2’彼此独立为C1-C18烷氧基,C3-C18链烯氧基,-OH或-O-CO-R12;
R3和R3’彼此独立为H,-OH,-O-CH2-CH(XA)-CH2-O-R7,,-O-CH2=C(=CH2)-R10,-O-(CH2)p-SiR11R11’-CH=CH2,-O-C(=O)-(CH2)q-CH=CH2,-O-C(=O)-O-CH2-C(=CH2)-R10,-O-CR8R8’-(CH2)1-XA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,-O-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,
-O-CR8R8’-(CH2)l-C(C=O)-XA,C1-C18烷基,C6-C12环烷基,C3-C18链烯基,-OR131,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(-O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C18烷基,C3-C6链烯基,-OR131,卤素,三氟甲基,苯基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基;C5-C12环烷基;C3-C18链烯基;苯基;取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;苯基-C1-C4-烷基;中间有1个或多个-O-的C3-C50烷基;1-金刚烷基;2-金刚烷基;降冰片基;2-甲基降冰片基或-C(=O)-R12;
R8和R8’彼此独立为H,C1-C18烷基,苯基,苯基-C1-C8-烷基,或取代有1-3个C1-C4烷基,C3-C8链烯氧基,C1-C8烷氧基,卤素或CF3的苯基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为H,C1-C18烷基,C2-C18链烯基,苯基,苯基-C1-C4烷基,C5-C12环烷基,C1-C12烷氧基,苯氧基,降冰片-2-基,5-降冰片烯-2-基或1-金刚烷基;
R13为H,C1-C18烷基,C3-C18链烯基,苯基,C5-C12环烷基,中间有1个或多个-O-的C3-C50烷基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基,1-金刚烷基,2-金刚烷基,降冰片基,2-甲基降冰片基;
R14和R15,彼此独立为H,C1-C18烷基,C3-C18链烯基,C6-C12环烷基,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-,苯基-S(=O)t-或OR131;
R131为C1-C18烷基,C3-C18链烯基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,C3-C6链烯氧基,卤素,-COOR13,-CONH2,-CONHR132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,苯氧基和/或由C1-C18烷基,C1-C18烷氧基或卤素取代的苯氧基的C1-C18烷基;或C3-C18链烯基;C6-C12环烷基;C1-C4烷基和/或-OCOR12取代的C6-C12环烷基;中间有一个或多个-O-无取代或取代有OH或O-CO-R12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
R132和R133彼此独立为C1-C12烷基,C3-C12烷氧基烷基,C4-C16二烷基氨基烷基或C5-C12环烷基;或
R132和R133一起为C3-C9亚烷基,C3-C9氧杂亚烷基或氮杂亚烷基;
X为-NR8-,-O-,-NH-(CnH2n)-NH-或-O-(CKH2K)-NH-;
k为2至4;
l为0至19;
m为2至8;
n为0至4;
p为0至10;
q为1至8;
r为0至18;
t为0,1或2。
其中
A为-C(=O)-CR5=CH-R6;
,-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,
-C(=O)-(CH2)q-CH=CH2或-C(=O)-O-CH2-C(=CH2)-R10;当R2’为OH或OA时,R1还可为-CH2-CH(OA)-CH2-O-R7;
R2和R2’彼此独立为H,-OH,-OA,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C2-C18链烯氧基,卤素,苯基或三氟甲基;
R3和R3’彼此独立为H,-OH,-OA,上述-OR1,-O-CHR8-(CH2)L-OA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)CH2-OA,-O-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C12烷基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基,环己基,C3-C18链烯基,苯基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C2-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C1-烷基或-C(=O)-R12;
R8为H或C1-C18烷基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为C1-C18烷基,C2-C18链烯基或苯基;
R13为H,C1-C18烷基,C3-C18链烯基或苯基;
l为0至19;
p为0至10;
q为1至8
r为0至18;
t为0,1或2。
3.权利要求1的通式(I)的化合物,其中
R2为H,C1-C4烷基,C3链烯基,F,Cl或苯基;
R2’为C1-C4烷氧基,C3链烯氧基,-O-CO-R12或-OH;
R3和R3’彼此独立为H,-OH,-O-CH2-CH(XA)-CH2-O-R7,,-O-CHR8-(CH2)1-XA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,C1- C4烷基,环己基,C3链烯基,-OR131,F,Cl,三氟甲基,苯基,苄基,或-CN;
R4’及R4”彼此独立为H,C1-C4烷基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯基-C1-C3烷基或-CN;
R5为H,或-CH3。
R6为H,-COOR13,CH3或苯基;
R7为C1-C8烷基,环己基,C3-C8链烯基,苯基,取代有1至3个C1-C4烷基或C1-C4烷氧基的苯基,或苄基;
R9为C1-C10烷基,苯基或苄基;
R11和R11’彼此独立为C1-C4烷基或苯基;
R12为C1-C18烷基,C2-C3链烯基,苯基,苯基C1-C4烷基或环己基;
R13为C1-C4烷基,C3链烯基,环己基,苯基C1-C4烷基或苯基;
R4,R14和R15,彼此独立为H,C1-C8烷基,F,Cl,C1-C4烷氧基,CF3,苯基,或CN;
R131为C1-C18烷基;取代有OH、C1-C18烷氧基、C5-C12环烷氧基、-COOR13、-CONH2、-COHNR132、-CON(R132)(R133),-NHCOR12,-CN,-OCOR12和/或苯氧基的C3-C18烷基;或C3链烯基;C6-C12环烷基;中间有一个或多个-O-可取代有OH或O-CO-R12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
X为-O-或-NR8-;
l为1-19;及
r为0至10。
4.权利要求1的化合物,其通式为(I),其中E1和E2彼此独立为通式Ia或Ib的基团,且其中
R1为或当R3’为-O-R8R8’-(CH2)L-XA时,R1还可为C1-C12的烷基或中间有-O-,-CO-O-或-O-CO-的C6-C18的烷基;及当E1为Ib基团时,R1还可为-CH2-CH(XA)-CH2-O-R7;并当E1为通式Ia,其中R2和R14都不是氢时,R1还可为-CH2-CH (XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH (OA)-R9,及-CH2-CH(OH)-CH2-XA;
R2为H,-CH3或Cl;
R2’为-OH;
R3为H,-CH3,C1-C4烷氧基,C3链烯氧基,F,Cl,苯基,苄氧基,或-CN;
-O-CH2-(CH2)1-XA,-O-CH2-CH(OA)-R9,-O-CH2-CH(OH)-CH2-XA,或-OR131;
R4,R14,R15彼此独立为H,F,Cl,OCH3或CH3;
R4’及R4”,在三嗪环的间位位置,彼此独立为H,-CH3,C3链烯基,-OCH3,C3链烯氧基,F,Cl,苯基-C3烷基或-CN;
R5为H,CH3;
R6为H;
R7为C1-C8烷基,环己基,C3链烯基,苯基或苄基;
R8和R8’为H;
R9为C1-C10烷基;
R12为C1-C18烷基,苯基或环己基;
R131为C3-C18烷基,或取代有OH,C1-C18烷氧基,-NHCOR12和/或-OCOR12的C3-C18烷基;且
l为0至19。
其中
其中
A为-C(=O)-CR5=CH-R6;
R1彼此独立为-CH2-CH(XA)-CH2-O-R7,-CR8R8’-(CH2)L-XA,-CH2-CH(OA)-R9,-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA,-CR8R’8-(CH2)l-C(=O)-XA或-C(=O)-O-CH2-C(=CH2)-R10;及,当E1为式If基团,其中R2和R14都不为氢时,R1还可为-A或-CH2-CH(OH)-CH2-XA;
R2彼此独立为C1-C12烷基,C5-C12环烷基,C3-C6链烯基,卤素,苯基或三氟甲基;
R2’彼此独立为C1-C18烷氧基,C2-C18链烯氧基,-OH或-O-COR12;
R3和R3’彼此独立为H,-OH,OR1,-OR131,C1-C18烷基,C3-C18链烯基,C6-C12环烷基,卤素,三氟甲基,苯基;苯基C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C18烷基,C3-C6链烯基,-OR131,卤素,三氟甲基,苯基,苯基-C1-C4烷基,一至三个C1- C4烷基取代的苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基,C5-C12环烷基,C3-C18链烯基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基,中间有1个或多个-O-的C3-C50烷基,1-金刚烷基,2-金刚烷基,降冰片基,2-甲基降冰片基或-C(=O)-R12或-A;
R8或R8’彼此独立为H,C1-C18烷基,苯基,苯基-C1-C4-烷基,或取代有1-3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或CF3的苯基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为H,C1-C18烷基,苯基,苯基-C1-C4烷基,C5-C12环烷基,C1-C12烷氧基,苯氧基,降冰片-2-基,5-降冰片烯-2-基或1-金刚烷基;
R13为H,C1-C18烷基,C3-C18链烯基,苯基,C5-C12环烷基,中间有1个或多个-O-的C3-C50烷基,取代有1至3个C1-C8烷基,或C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基,2-金刚烷基,降冰片基,2-甲基降冰片基;
R14和R15,彼此独立为H,C1-C18烷基,C3-C18链烯基,C6-C12环烷基,卤素,三氟甲基,苯基,苯基-C1-C4烷基,-CN,C1-C18烷基-S(=O)t,苯基-S(=O)t-或OR131;
R131为C1-C18烷基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,C3-C6链烯氧基,卤素,-COOR13,-CONH2,-COHN-R132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,苯氧基和/或被C1-C18烷基,C1-C18烷氧基或卤素取代的苯氧基的C1-C18烷基;或C3-C18链烯基;C6-C12环烷基;C1-C4烷基和/或-OCOR12取代的C6-C12环烷基;中间有一个或多个-O-可取代有OH或-O-COR12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
R132和R133彼此独立为C1-C12烷基,C3-C12烷氧基烷基,C4-C16二烷基氨基烷基或C5-C12环烷基;或
R132和R133一起为C3-C9亚烷基,C3-C9氧杂亚烷基或氮杂亚烷基;
X为-NR8-,-O-,-NH-(CnH2n)-NH-或-O-(CKH2K)-NH-;
k为2至4;
l为0至19;
m为2至8;
n为0至4;
p为0至10;
q为1至8;
r为0至18;及
t为0,1或2。
6.权利要求5的聚合化合物,其可通过至少一种通式(Ih)的化合物或至少一种通式(Ih)的化合物和至少一种其它乙烯不饱和化合物加成聚合制得
A为-C(=O)-CR5=CH-R6;
R1彼此独立为-CH2-CH(OA)-CH2-O-R7,-CHR8-(CH2)L-OA,
-CH2-CH(OA)-R9,-CH2-CH(OH)-CH2-OA,
,-CH2-C(=CH2)-R10,-(CH2)p-SiR11R11’-CH=CH2,-C(=O)-(CH2)q-CH=CH2,-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA或-C(=O)-O-CH2-C(=CH2)-R10;
R2和R2’彼此独立为H,-OH,-OA,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C2-C18链烯氧基,卤素,苯基或三氟甲基;
R3和R3’彼此独立为H,-OH,-OA,-OR1,C1-C12烷基,环己基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R4,R4’及R4”,彼此独立为H,C1-C12烷基,C3-C6链烯基,C1-C18烷氧基,C3-C18链烯氧基,卤素,三氟甲基,苯基,苯氧基,苯基-C1-C4烷基,一至三个C1-C4烷基取代的苯基-C1-C4烷基,苯基-C1-C4烷氧基,-CN,C1-C18烷基-S(=O)t-或苯基-S(=O)t-;
R5为H,-CH2-COOR13,C1-C4烷基或-CN;
R6为H,-COOR13,C1-C17烷基或苯基;
R7为C1-C18烷基,环己基,C3-C18链烯基,苯基,取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基,苯基-C1-C4-烷基或-C(=O)-R12;
R8为H或C1-C18烷基;
R9为C1-C18-烷基,苯基或苯基-C1-C4烷基;
R10为H或-CH3;
R11和R11’彼此独立为C1-C4烷基或苯基或取代有1至3个C1-C8烷基,C1-C8烷氧基,C3-C8链烯氧基,卤素或三氟甲基的苯基;
R12为C1-C18烷基,C2-C18链烯基或苯基;
R13为H,C1-C18烷基,C3-C18链烯基或苯基;
l为0至19;
p为0至10;
q为1至8;
r为0至18;及
t为0,1或2。
7.权利要求5的聚合化合物,其中
R1彼此独立为-CH2-CH(XA)-CH2-CO-R7,-CR8R8’-(CH2)L-XA,,-CH2-CH(OA)-R9,
或-CHR8-(CH2)r-C(=O)-O-CH2-CH(OH)-CH2-OA;
R2为H,C1-C4烷基,C3链烯基,F,Cl或苯基;
R2’为C1-C4烷氧基,C3链烯氧基,-OA,-O-COR12或-OH;
R3和R3’彼此独立为H,OH,OR1,-OR131,C1-C4烷基,环己基,C3链烯氧基,F,Cl,三氟甲基,苯基,苄基或-CN;
R4’及R4”彼此独立为H,C1-C4烷基,C3链烯基,C1-C4烷氧基,C3链烯氧基,F,Cl,三氟甲基,苯基,苯基-C1-C3烷基或-CN;
R5为H或-CH3。
R6为H,-COOR13,CH3或苯基;
R7为C1-C8烷基,环己基,C3-C8链烯基,苯基,取代有1至3个C1-C4烷基或C1-C4烷氧基的苯基,或苄基;
R8和R8’为彼此独立的H或C1-C18烷基。
R9为C1-C10烷基,苯基或苄基;
R12为H,C1-C18烷基,苯基,苯基-C1-C4烷基或环己基;
R13为C1-C4烷基,C3链烯基,环己基,苯基-C1-C4烷基或苯基;
R4,R14和R15,彼此独立为H,F,Cl,C1-C4烷氧基,CF3,苯基,CN或C1-C8烷基;
R131为C1-C18烷基,取代有OH,C1-C18烷氧基,C5-C12环烷氧基,-COOR13,-CONH2,-COHNR132,-CON(R132)(R133),-NHCOR12,-CN,-OCOR12,和/或苯氧基的C3-C18烷基;或C3链烯基;C6-C12环烷基;中间有一个或多个-O-可取代有OH或O-COR12的C3-C50烷基;苯基;苯基-C1-C4烷基;-COR12或-SO2R12;
X优选-O-或-NR8-;
l为1-19;及
r为0至10。
8.权利要求5的聚合化合物,其中
A为-C(=O)-CR5=CH-R6;
R2为H,-CH3,-OCH3,C3链烯氧基或Cl;
R2’为-OH;
R3为H,-CH3,C1-C4烷氧基,C3链烯氧基,F,Cl,苯基,苄氧基或-CN;
R3’为-OR1,-OR131;
R4,R14和R15,彼此独立为H,F,Cl,苯基,CH,OCH3或CH3;
R4’及R4”彼此独立为H,-CH3,C3链烯基,-OCH3,C3链烯氧基,F,Cl,苯基-C3烷基或-CN;
R5为H或-CH3。
R6为H或-CH3;
R7为C1-C8烷基,环戊基,环己基,C3链烯基,苯基或苄基;
R8为H或C1-C8烷基。
R9为C1-C10烷基或苯基;
R12为C1-C18烷基,苯基或环己基;
R131为C3-C18烷基,或取代有C1-C18烷氧基,OH,苯氧基,-NHCOR12和/或-OCOR12的C3-C18烷基;且
l为1-19;
10.权利要求5的聚合化合物,其可通过至少一种权利要求5的通式(Id)的化合物和至少一种其它共聚用单体共聚而制得,其中其它共聚用单体选自丙烯酸,甲基丙烯酸,丙烯酸酯,甲基丙烯酸酯,丙烯酸酰胺,甲基丙烯酸酰胺,乙烯醚,苯乙烯,苯乙烯衍生物,乙烯基吡啶,丙烯腈,甲基丙烯腈,乙烯基吡咯烷酮,乙烯基吡咯烷酮衍生物,和具空间位阻的胺类的乙烯不饱和衍生物,2-(2,-羟基苯基)苯并***,2-羟基苯酮和具空间位阻的苯酚。
11.权利要求10的聚合化合物,其中其它共聚用单体为通式(II)-(VII):
(II) R18-CH-C(R17)-C(=O)-X’-R20,
其中X’是-O-或-NR19-;
R17是H,C1-C4烷基,-CH2-COOR21-Cl或-CH;
R18是H,-COOR21或-CH3;
R19为H,C1-C8烷基,C4-C12环烷基,-N(Rx)2取代的C1-C4烷基,-S(=O)-RX,-C(CH3)2-CH2-C(=O)-CH3,-C(CH3)2-CH2-SO3M,-(CH2)s-SO3M或
R20为H,C1-C18烷基,C3-C18链烯基,中间有一个或多个O原子可取代有OH的C2-C18烷基,或-(CH2)s-SO3M,,-CH2F,-CH2Cl,-CH2CN,-CH2CH2Cl,-CH2CH2CN,-CH2CH2-COORX,C7-C11苯基烷基,萘基,-N(RX)2取代的C1-C4烷基,金刚烷基或C6-C12环烷基;
R21为H,C1-C18烷基,苯基或C3-C18链烯基;
RX为C1-C4烷基或苯基;
RY为H,C1-C12烷基,苯基,-CO-ORX,-CN,-F,或-Cl;
M为H或碱金属;且
s为1至5。
(III) R22-C(=O)-O-CH=CH2,
其中R22为C1-C19烷基或苯基。
(IIIa) R22a-O-CH=CH2,
其中R22a为C1-C18烷基。其中R23为H或-CH3;
R24为H,-CR23=CH2,-C(O)-苯基或-SO3M;且
其中R25为H或-CH3。
(VI) CH2=CR26-R27,
R26为H,-F,-Cl或-CH3
且R27为-Cl、-Br,-F或-CN。
12.权利要求11的聚合化合物,其可通过至少一个通式(Id)的化合物与至少一个权利要求11的通式(II)-(IV)和(VII)之一的其它共聚用单体共聚合反应制得,
其中R17是H或CH3;
R18是H或-CH3;
R19为H,C1-C4烷基,-C(CH3)2-CH2-SO3M,或-(CH2)s-SO3M;
R20为H,C1-C8烷基,或中间有一个或多个O原子的C2-C20烷基;
R22为CH3;
R22a为C1-C4烷基;
R23和R24为H;
M为H,Li,Na,或K;
X是-O-或-NR19-;及
s为2或3。
13.结合2-羟基苯基三嗪至有机聚合物上的方法,其中包括在制备聚合物过程通过共聚缩合反应或共聚加成反应结合权利要求1的通式(I)化合物,或者权利要求1的通式(I)化合物与含有适当官能团的聚合物反应。
14.可根据权利要求13制得的有机聚合物,其中包含0.05-50%重量比的通式(I)化合物。
15.一种有机材料,其包含权利要求1的通式(I)化合物或权利要求5的聚合化合物作为抗光、氧和/或热损害作用的稳定剂。
16.权利要求15的有机材料,其为一种有机聚合物。
17.权利要求15的有机材料,其为涂料组合物的粘合剂。
18.一种稳定有机材料抗光、氧和/或热损害作用的方法,其中包括向其中加入作为稳定剂的权利要求1的通式(I)化合物或权利要求5的聚合化合物。
19.权利要求1的通式(I)化合物或权利要求5的聚合化合物的用途,用其稳定有机材料抗光、氧和/或热损害作用的用途。
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CH484695A (de) * | 1962-10-30 | 1970-01-31 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Ultraviolettschutzmittel ausserhalb der Textilindustrie |
NL130993C (zh) * | 1963-02-07 | |||
CH469053A (de) * | 1963-07-26 | 1969-02-28 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Schutzmittel gegen Ultraviolettstrahlung für nichttextile organische Materialien |
CH485484A (de) * | 1964-12-04 | 1970-02-15 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Schutzmittel gegen Ultraviollettstrahlung für organische Materialien ausserhalb der Textilindustrie |
CH481954A (de) * | 1965-11-09 | 1969-11-30 | Ciba Geigy | Verfahren zur Herstellung von gegen die Einwirkung ultravioletter Strahlen geschützten Polymeren |
US3641213A (en) * | 1969-02-27 | 1972-02-08 | American Cyanamid Co | Synergistic uv absorber combination for polypropylene-polyvinylpyridine blend |
ES2100878T3 (es) * | 1989-12-05 | 1997-07-01 | Ciba Geigy Ag | Material organico estabilizado. |
US5189084A (en) * | 1989-12-21 | 1993-02-23 | Ciba-Geigy Corporation | Process for incorporating o-hydroxyphenyl-s-triazines in organic polymers |
DE59009628D1 (de) * | 1989-12-21 | 1995-10-12 | Ciba Geigy Ag | Verfahren zum Einbau von O-Hydroxyphenyl-S-triazinen in organische Polymere. |
EP0530135A1 (de) * | 1991-06-03 | 1993-03-03 | Ciba-Geigy Ag | UV-Absorber enthaltendes photographisches Material |
EP0520938B1 (de) * | 1991-06-03 | 1997-09-24 | Ciba SC Holding AG | UV-Absorber enthaltendes photographisches Material |
DE59208885D1 (de) * | 1991-09-05 | 1997-10-16 | Ciba Geigy Ag | UV-Absorber enthaltendes photographisches Material |
-
1995
- 1995-09-28 US US08/535,406 patent/US5672704A/en not_active Expired - Lifetime
- 1995-10-02 SK SK1230-95A patent/SK123095A3/sk unknown
- 1995-10-02 DE DE19536730A patent/DE19536730A1/de active Granted
- 1995-10-02 CZ CZ952556A patent/CZ255695A3/cs unknown
- 1995-10-02 CA CA002159694A patent/CA2159694A1/en not_active Abandoned
- 1995-10-02 GB GB9520046A patent/GB2293823B/en not_active Expired - Fee Related
- 1995-10-03 FR FR9511598A patent/FR2725204B1/fr not_active Expired - Fee Related
- 1995-10-03 IT IT95MI002019A patent/IT1281195B1/it active IP Right Grant
- 1995-10-03 AU AU33049/95A patent/AU698297B2/en not_active Ceased
- 1995-10-03 AT AT0163695A patent/AT405515B/de not_active IP Right Cessation
- 1995-10-04 CN CN95117220A patent/CN1070186C/zh not_active Expired - Fee Related
- 1995-10-04 BE BE9500822A patent/BE1008871A5/fr not_active IP Right Cessation
- 1995-10-04 JP JP28261895A patent/JP4126400B2/ja not_active Expired - Lifetime
- 1995-10-04 ES ES09501914A patent/ES2106684B1/es not_active Expired - Fee Related
- 1995-10-04 BR BR9504276A patent/BR9504276A/pt not_active IP Right Cessation
- 1995-10-04 KR KR1019950034446A patent/KR960014109A/ko not_active Application Discontinuation
- 1995-10-04 NL NL1001338A patent/NL1001338C2/xx not_active IP Right Cessation
-
1997
- 1997-05-29 US US08/865,148 patent/US5869588A/en not_active Expired - Lifetime
-
2003
- 2003-04-14 KR KR1020030023506A patent/KR100496131B1/ko not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101743261B (zh) * | 2007-07-13 | 2013-04-03 | 昭和电工株式会社 | 含有三嗪环的高分子化合物和使用该高分子化合物的有机发光元件 |
US8426037B2 (en) | 2007-07-13 | 2013-04-23 | Showa Denko K.K. | Triazine ring-containing polymer compound and organic light-emitting element using the polymer compound |
CN110678448A (zh) * | 2017-05-25 | 2020-01-10 | 株式会社Adeka | 三嗪化合物、固化性组合物、固化物的制造方法及其固化物 |
CN107935952A (zh) * | 2017-12-01 | 2018-04-20 | 北京天罡助剂有限责任公司 | 一种三嗪‑5的制备方法 |
CN107935952B (zh) * | 2017-12-01 | 2019-11-15 | 北京天罡助剂有限责任公司 | 一种三嗪-5的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
ITMI952019A1 (it) | 1997-04-03 |
US5672704A (en) | 1997-09-30 |
CA2159694A1 (en) | 1996-04-05 |
ES2106684B1 (es) | 1998-07-01 |
SK123095A3 (en) | 1996-06-05 |
DE19536730A1 (de) | 1996-04-11 |
JPH08259545A (ja) | 1996-10-08 |
AU698297B2 (en) | 1998-10-29 |
ES2106684A1 (es) | 1997-11-01 |
AT405515B (de) | 1999-09-27 |
US5869588A (en) | 1999-02-09 |
FR2725204A1 (fr) | 1996-04-05 |
NL1001338C2 (nl) | 1996-04-12 |
FR2725204B1 (fr) | 1997-06-06 |
AU3304995A (en) | 1996-04-18 |
GB2293823A (en) | 1996-04-10 |
JP4126400B2 (ja) | 2008-07-30 |
NL1001338A1 (nl) | 1996-04-04 |
CN1070186C (zh) | 2001-08-29 |
IT1281195B1 (it) | 1998-02-17 |
KR100496131B1 (ko) | 2005-06-17 |
BR9504276A (pt) | 1996-10-01 |
GB9520046D0 (en) | 1995-12-06 |
CZ255695A3 (en) | 1996-04-17 |
GB2293823B (en) | 1997-01-22 |
ATA163695A (de) | 1999-01-15 |
ITMI952019A0 (zh) | 1995-10-03 |
KR960014109A (ko) | 1996-05-22 |
BE1008871A5 (fr) | 1996-08-06 |
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