CN1890335A - 包含由硝酰基介导的聚合制备的流平剂的涂料组合物 - Google Patents
包含由硝酰基介导的聚合制备的流平剂的涂料组合物 Download PDFInfo
- Publication number
- CN1890335A CN1890335A CNA2004800368770A CN200480036877A CN1890335A CN 1890335 A CN1890335 A CN 1890335A CN A2004800368770 A CNA2004800368770 A CN A2004800368770A CN 200480036877 A CN200480036877 A CN 200480036877A CN 1890335 A CN1890335 A CN 1890335A
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- China
- Prior art keywords
- alkyl
- acid
- alkyl ester
- coating composition
- ester
- 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.)
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 94
- 239000008199 coating composition Substances 0.000 title claims abstract description 53
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 230000001404 mediated effect Effects 0.000 title claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 66
- 238000000576 coating method Methods 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 239000000843 powder Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 27
- 229920000642 polymer Polymers 0.000 claims abstract description 17
- -1 alkyl acrylamide Chemical compound 0.000 claims description 274
- 229910052757 nitrogen Inorganic materials 0.000 claims description 74
- 229920005989 resin Polymers 0.000 claims description 63
- 239000011347 resin Substances 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 60
- 239000011248 coating agent Substances 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 53
- 239000011230 binding agent Substances 0.000 claims description 41
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 39
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 38
- 125000005907 alkyl ester group Chemical group 0.000 claims description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000003999 initiator Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 238000004132 cross linking Methods 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 21
- 239000000470 constituent Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000003973 paint Substances 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000010526 radical polymerization reaction Methods 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 239000012634 fragment Substances 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 12
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 8
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000003292 glue Substances 0.000 claims description 7
- 230000014509 gene expression Effects 0.000 claims description 6
- 230000007246 mechanism Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000004584 polyacrylic acid Substances 0.000 claims description 4
- 230000005670 electromagnetic radiation Effects 0.000 claims description 3
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 230000003750 conditioning effect Effects 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 abstract description 13
- 229920001577 copolymer Polymers 0.000 abstract description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 3
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 34
- 150000002148 esters Chemical class 0.000 description 31
- 239000002585 base Substances 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 23
- 150000001721 carbon Chemical group 0.000 description 23
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 20
- 229920000728 polyester Polymers 0.000 description 20
- 238000005227 gel permeation chromatography Methods 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 239000012965 benzophenone Substances 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 238000003760 magnetic stirring Methods 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 229940059574 pentaerithrityl Drugs 0.000 description 11
- 229910052723 transition metal Inorganic materials 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 10
- 239000001272 nitrous oxide Substances 0.000 description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 230000002194 synthesizing effect Effects 0.000 description 10
- 150000003624 transition metals Chemical class 0.000 description 10
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 9
- 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 9
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 9
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 8
- 241000723346 Cinnamomum camphora Species 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229930008380 camphor Natural products 0.000 description 8
- 229960000846 camphor Drugs 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000003351 stiffener Substances 0.000 description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- 229920000877 Melamine resin Polymers 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- 230000000977 initiatory effect Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000012628 flowing agent Substances 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 5
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 5
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 150000003851 azoles Chemical class 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
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- 150000002460 imidazoles Chemical class 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- 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 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 239000004640 Melamine resin Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D157/00—Coating compositions based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
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Abstract
本发明涉及包含聚合物或共聚物流平剂的涂料组合物,其中该流平剂由硝酰基介导的聚合制备。本发明还进一步涉及制备平滑表面涂料的方法和该聚合物或共聚物作为涂料组合物中流平剂的用途。另一方面,本发明还涉及具体的烯属不饱和单体组合物,从该组合物可以由原子转移自由基聚合或硝酰基介导的聚合获得共聚物,其中该共聚物用作涂料组合物中的流平剂。另一方面,本发明还涉及聚丙烯酸叔丁酯或聚甲基丙烯酸叔丁酯作为粉末涂料组合物中流平剂的用途。
Description
本发明涉及包含聚合物或共聚物流平剂的涂料组合物,其中该流平剂由硝酰基介导的聚合制备。本发明还进一步涉及制备平滑表面涂料的方法和该聚合物或共聚物作为涂料组合物中流平剂的用途。另一方面,本发明还涉及具体的烯属不饱和单体组合物,从该组合物可以由原子转移自由基聚合或硝酰基介导的聚合获得共聚物,其中该共聚物用作涂料组合物中的流平剂。另一方面,本发明还涉及聚丙烯酸叔丁酯或聚甲基丙烯酸叔丁酯作为粉末涂料组合物中流平剂的用途。
在本发明的上下文中理解术语涂料组合物定义有机涂料组合物。
由于不仅仅提供美观也提供保护功能,对于几乎所有的涂料应用要求平滑和无焰口表面。在涂料不均匀和一些部分表面没有,或仅非常薄地涂覆的情况下得到差的保护。为达到平滑表面,将流平剂加入所有种类的涂料。合适的流平剂是,例如衍生自烯属不饱和单体,如丙烯酸酯或甲基丙烯酸酯的聚合物或共聚物。在液体涂料配制剂的情况下,大量流平剂是已知并可从市场中购得。只要涂料配制剂的粘度低,可以采用这些常规流平剂获得足够的流平。当粘度增加时观察到问题逐渐增多,如对于高固体涂料或特别对于粉末涂料的情况。特别地在可热或辐射固化的粉末涂料的情况下,对改进涂料流平的添加剂有着强烈需求。
因此进行尝试以通过控制聚合物构造而改进流平剂在热固性涂料中的作用。例如US6,197,883公开了包含流平剂的热固性涂料组合物,该流平剂使用原子转移自由基聚合技术(ATRP)聚合。
WO03/027155进一步描述了由ATRP工艺制备并包含具有硅氧烷或全氟烷基部分的共聚物流平剂的热固性涂料组合物。
然而,仍然需要改进的流平剂,它提供不同和改进的性能平衡,如关于流平性能,变黄倾向性和处理性能。因此聚合物构造的优化控制显现为改进的关键。
本发明涉及包含流平剂的涂料组合物,该流平剂由硝酰基介导的自由基聚合(NO·和NOR)合成。取决于使用硝酰基醚或硝酰基的官能度和反应性,可以采用各种单体获得线性,支化,渐变和接枝结构。此类型的受控自由基聚合允许合成分子量和窄分子量分布定义较好的聚合物或共聚物。通过调节分子量,可以获得液体或固体(共)聚合物。
特别地,对于粉末涂料固体,流平剂具有极大的优点。通常必须通过在各自的粉末涂料中制备母料,将其吸收到二氧化硅上或施加另一种固体载体将液体流平剂配制成固体产品的形式。这导致生产成本以及原料保持的增加。由于化合物不再是100%活性的,必须向涂料配制剂中加入更高的数量。固体活性材料缓解了不同母料的原料保持问题,并允许向配制剂中加入更低的数量。采用本发明可以配制粉末涂料,该粉末涂料包含例如具有窄分子量分布和玻璃化转变温度Tg或熔融温度Tm高于30℃的各种丙烯酸酯/甲基丙烯酸酯单体的均聚物或共聚物,使得可以将材料作为固体化合物处理为固体复合物,而不需要进一步的配制。
对于许多涂料应用,例如透明涂层或白色固体遮光物,没有或仅轻微淡黄色外观是可容忍的。令人惊奇地发现与现有技术流平剂相比,本发明的流平剂导致涂料的显著降低变黄。
本发明的一方面是一种涂料组合物,该组合物包括:
a1)一种或多种物理干燥成膜粘结剂树脂;
a2)一种或多种热交联成膜粘结剂树脂;
a3)一种或多种可辐射固化的成膜粘结剂树脂;
a4)一种或多种自氧化干燥成膜粘结剂树脂;或
a5)选自a1)、a2)、a3)或a4)的具有至少两种不同交联机理的粘结剂树脂的组合;
b)由硝酰基介导的受控自由基聚合获得的通式(I)In-[(M)x-(E)y]n(I)的聚合物或共聚物流平剂,其中
In是开始聚合反应的引发剂片段;
M是选自如下的至少一种单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C22)烷基酯、丙烯酸(C1-C22)羟烷基酯、甲基丙烯酸(C1-C22)烷基酯、甲基丙烯酸(C1-C22)羟烷基酯、丙烯酸(C1-C22)烷基酯或甲基丙烯酸(C1-C22)烷基酯,其由氨基、(C1-C22)烷基氨基、(C1-C22)二烷基氨基、-SO3H、环氧、氟、全氟或硅氧烷基团取代、苯乙烯、取代的苯乙烯、丙烯酰胺和甲基丙烯酰胺、N-单(C1-C22)烷基丙烯酰胺、N,N-二(C1-C22)烷基丙烯酰胺,和具有两个或多个烯属不饱和键的多官能单体;
条件是未取代丙烯酸(C1-C22)烷基酯或/和甲基丙烯酸(C1-C22)烷基酯的数量大于30wt%,基于总单体混合物的重量;
E是带有至少一个稳定硝酰基自由基的基团,其通过氧原子结合到聚合物或共聚物;或来自连接的稳定硝酰基自由基的取代或消除反应的基团;
x是单体单元的总数目,它是5-5000的数;
y是1或大于1的数,指示连接到单体序列(M)x的端基E的平均数目;
n是1-20的数;和
c)任选地水或/和一种或多种有机溶剂。
C1-C22烷基可以是线性或支化的。这样烷基的例子是甲基、乙基、丙基、异丙基、丁基、2-丁基、异丁基、叔丁基、戊基、2-戊基、己基、庚基、辛基、2-乙基己基、叔辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十六烷基、十八烷基和二十烷基。优选是C1-C18烷基。
按照a1)提及的成膜物理干燥粘结剂树脂典型地衍生自α,β-不饱和酸及其衍生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。例子是热塑性聚丙烯酸酯(TPA)。
另一类例如衍生自天然聚合物,如乙酸或丁酸纤维素。也合适的是物理干燥醇酸树脂或硝基纤维素漆。
按照a2)提及的热交联成膜粘结剂树脂例如是以下给出的那些。
1.一方面衍生自醛另一方面衍生自酚、脲和蜜胺的交联聚合物,如苯酚/甲醛树脂、脲/甲醛树脂和蜜胺/甲醛树脂。
2.干燥和非干燥醇酸树脂。
3.衍生自饱和及不饱和二羧酸与多元醇和作为交联剂的乙烯基化合物的共聚酯的不饱和聚酯树脂,和同样低可燃性的其含卤素改性物。
4.衍生自取代丙烯酸酯,例如环氧丙烯酸酯、尿烷丙烯酸酯或聚酯丙烯酸酯的可交联丙烯酸类树脂。这些树脂典型地与蜜胺树脂或(多)异氰酸酯树脂交联和已知为热固性丙烯酸类。
5.由蜜胺树脂、脲树脂、异氰酸酯、异氰脲酸酯、多异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂和丙烯酸酯树脂。
6.衍生自脂族、环脂族、杂环或芳族缩水甘油基化合物的交联的环氧树脂,如双酚A和双酚F的二缩水甘油醚产物,它与通常的硬化剂如酸酐或胺交联,采用或不采用促进剂。
可以用作本发明中成膜粘结剂树脂的交联醇酸树脂是常规烘漆,该烘漆特别用于涂覆汽车(汽车涂饰漆),例如基于醇酸/蜜胺树脂和醇酸/丙烯酸类/蜜胺树脂的漆(参见H.Wagner和H.F.Sarx,″Lackkunstharze″(1977),99-123页)。其它交联剂包括甘脲树脂,封端的异氰酸酯或环氧树脂。
涂料组合物可以在木材、金属或塑料衬底上施加。
本涂料组合物特别适于金属涂饰涂料和汽车的固体遮光物涂饰两者,特别地在修整涂饰的情况下,以及各种线圈涂覆应用。本发明的涂料组合物优选以常规的方式应用在两种方法中,即单涂层方法或双涂层方法。在后者的方法中,将含颜料的基础涂层首先施加,然后在它之上覆盖透明漆的涂层。
当需要水溶性、水混溶或可水分散涂料时,形成树脂中存在的酸基团的铵盐。粉末涂料组合物可以如以下说明的通过反应甲基丙烯酸缩水甘油酯与选择的醇组分而制备。
当在涂料组合物中不存在有机溶剂或水时,组分b)流平剂是特别有用的。这典型地是对于粉末涂料的情况。
粉末涂料是已知技术,并在例如″Ullmann′工业化学百科全书,第五完全修正版,A18卷″,438-444页(1991)中被公开。在粉末涂料工艺中,通常通过空气的供应将粉末流化,带静电和施加到接地的优选金属衬底。随后加热衬底,在其过程中粘合粉末熔融、聚结,并在金属表面上形成粘附膜。由于粉末涂料不要求溶剂,因此该技术对环境是特别有益的。
粉末涂料表示热塑性或可烘烤、可交联聚合物,将该聚合物以粉末形式施加到主要金属衬底。其中将粉末与要涂覆的工件接触的方式是各种施加技术的特征,例如采用电晕或摩擦电喷枪的静电粉末喷涂,静电流化床烧结或通过使用磁性刷技术。
用于本发明的粉末涂料组合物的优选有机成膜粘合剂是基于,例如环氧树脂、聚酯-羟烷基酰胺、聚酯-甘脲、环氧-聚酯树脂、聚酯-异氰脲酸三缩水甘酯、羟基官能聚酯-封端的多异氰酸酯、羟基官能聚酯-脲二酮、丙烯酸酯树脂与硬化剂或这样树脂的混合物的烘烤体系。也感兴趣的是具有热塑性性能的成膜粘合剂,例如聚乙烯、聚丙烯、聚酰胺、聚氯乙烯、聚偏二氯乙烯或聚偏二氟乙烯。
一般来说,聚酯是羟基或羧基官能的,并通常由二元醇和二羧酸的缩合来制备。加入多元醇和/或多元酸产生支化聚酯,该支化聚酯然后在交联剂存在下烘烤时,得到网络结构,该网络结构向涂料赋予所需的物理性能,如耐擦划性,冲击强度和挠曲强度。代替多官能酸也可以使用酸酐或酰氯,例如马来酸酐、衣康酸酐、邻苯二甲酸酐、对苯二甲酸酐、六氢对苯二甲酸酐、1,2,4-苯三酸酐、苯均四酸二酐或琥珀酸酐。也可以使用简单酯,例如对苯二甲酸二甲酯,聚合通过酯交换与消除挥发性醇的消除而进行。同样可实施的是通过酯交换和缩合的组合来制备。此外,聚酯可以由羟基羧酸,例如12-羟基硬脂酸和羟基新戊酸,或对应的内酯,例如ε-己内酯的缩聚来制备。二羧酸和多元酸的例子包括对苯二甲酸、间苯二甲酸、己二酸、壬二酸、癸二酸、1,12-十二烷二酸、1,2,4,5-苯四酸、3,6-二氯邻苯二甲酸、琥珀酸、1,3-环己烷二羧酸和1,4-环己烷二羧酸。二元醇和多元醇的例子包括乙二醇、丙二醇、甘油、己三醇、己烷-2,5-二醇、己烷-1,6-二醇、季戊四醇、山梨醇、新戊二醇、三羟甲基乙烷、三羟甲基丙烷、三-1,4-环己烷二甲醇、三甲基戊二醇、2,2-二乙基-1,3-丙二醇、2-甲基-2-丁基-1,3-丙二醇、Esterdiol 204(羟基新戊酸和新戊二醇的酯)、氢化双酚A、双酚A、羟基新戊酸、羟基新戊酸酯、2-丁基-2-乙基-1,3-丙二醇、1,4-丁二醇、2-丁烯-1,4-二醇、2-丁炔-1,4-二醇或2-甲基-1,3-丙二醇。
用于羧基官能聚酯的合适交联剂是环氧化合物,例如Novolac-环氧树脂、双酚A的二缩水甘油基醚、氢化双酚A和通过与,例如脂族二羧酸的反应而改性的双酚A。也合适的是反应性环氧化合物,如三缩水甘油基三唑烷-3,5-二酮、多元酸的缩水甘油基酯,例如对苯二甲酸二缩水甘油酯和六氢对苯二甲酸二缩水甘油酯、乙内酰脲环氧化物(US-A-4 402 983)和,非常特别地异氰脲酸三缩水甘油酯和脂族多环氧化合物,例如AralditPT910(以前Ciba SpecialtyChemicals)和同样环氧化多饱和脂肪酸酯,例如Uranox(DSM)。用于羧基官能聚酯的其它交联剂是羟基烷基酰胺(参见US-A-4 076917),例如己二酸的主四官能羟基烷基酰胺衍生物(Rohm & Haas生产的PrimidXL552和PrimidQM 1260)。也发现由低分子量醇烷基化的蜜胺、苯并胍和甘脲的衍生物同样是合适的。例子是四甲基甲氧基甘脲(Powderlink1174,购自American Cyanamid)。其它已知的交联剂是双-和三唑烷,例如1,4-双唑烷并苯。
近来的物质是羧基官能聚酯,该聚酯包括化学结合环氧基团,因此能够自身交联(Molhoek等人,22nd Fatipec Congress,15.-19.5.95,Budapest,Vol.1,119-132)。
交联反应中环氧基团或缩水甘油基与羧基或酸酐反应的所有体系中,可以采用催化剂。例子是胺或金属化合物,例如乙酰丙酮铝或辛酸锡。
作为用于羟基官能聚酯的交联剂,多异氰酸酯交联剂是特别重要的。为防止由于异氰酸酯的高反应性而造成的过早交联和为获得熔融粉末的良好流平,将多异氰酸酯封端(内部作为脲二酮或作为与封端剂的加合物)。
最通常采用的封端剂是己内酰胺、甲基乙基酮肟或丁酮肟。用于异氰酸酯的其它合适封端剂描述于出版物,G.B.Guise,G.N.Freeland和G.C.Smith,J.Applied Polymer Science,23,353(1979)和M.Bock和H.-U.Maier-Westhuesin″粉末涂料技术的产物开发中的进展,XIXthInt.Conf.on Organic Coatings,Science和Technol.,Athens,12-16 July″,1993。封端和未封端多异氰酸酯的例子包括2-甲基戊烷1,5-二异氰酸酯、2-乙基丁烷1,4-二异氰酸酯、3(4)-异氰酸根合甲基-1-甲基环己基异氰酸酯、3-异氰酸根合甲基-3,5,5-三甲基环己烷二异氰酸酯、三(异氰酸根合甲基)苯、4,4′-二异氰酸根合二环己基甲烷、1,4-双(异氰酸根合甲基)环己烷、间四甲基二甲苯二异氰酸酯、对四甲基二甲苯二异氰酸酯和特别地,异佛尔酮二异氰酸酯。对于未封端二异氰酸酯的反应,通常将金属催化剂,例如辛酸锡、氧化二丁基锡或二月桂酸二丁基锡加入到多异氰酸酯配制剂。
用于羟基官能聚酯的进一步合适交联剂是酸酐,例如1,2,4-苯三酸酐和其与二元醇和二元胺的反应产物。这样交联剂的进一步例子由T.A.Misev描述于″粉末涂料:化学和技术″,J.Wiley & Sons,Chichester,123和124页。
通常含有羟基、羧基或缩水甘油基官能度的聚丙烯酸酯也用作粉末涂料的粘结剂,它们由通常的方法,主要从单体,例如苯乙烯和丙烯酸或甲基丙烯酸的线性或支化C1-C8烷基酯制备。其它烯属不饱和化合物,例如二乙烯基苯、丙烯酰胺、甲基丙烯酰胺、丁氧基甲基丙烯酰胺、丙烯腈或丁二烯也可以加入和共聚。羟基官能度由羟基官能单体,例如丙烯酸羟乙酯、甲基丙烯酸羟乙酯、丙烯酸羟丙酯、甲基丙烯酸羟丙酯的共聚保证。对于羧基官能度,使用烯属不饱和酸和酸酐,例如丙烯酸、甲基丙烯酸、衣康酸、巴豆酸、马来酸酐、衣康酸酐、丙烯酸酐或甲基丙烯酸酐(US-A-3 836 604)。缩水甘油基官能度,如在EP-A-0 256 369和US-A-3 876 578中所教导,由单体如丙烯酸缩水甘油酯和甲基丙烯酸缩水甘油酯的共聚提供。作为用于具有羟基或羧基官能度的聚丙烯酸酯的交联剂,原则上可以使用与对于具有羟基或羧基官能度的聚酯所述相同的化合物。进一步合适的交联剂是US-A 0 045 040的环氧化合物。用于具有缩水甘油基官能度的聚丙烯酸酯的合适交联剂是二羧酸,例如癸二酸、1,12-十二烷二羧酸和酸酐,例如双1,2,4-苯三酸酐,和在US-A-3 880 946中所述的化合物。此外,来自DE-A-3 310 545的自交联聚丙烯酸酯也是已知的。
用于粉末涂料的环氧树脂大部分是Novolac-环氧树脂或特别地,基于芳族多元醇的环氧树脂,特别地基于双酚如双酚A的环氧树脂。也已知的是来自JP-A-58 187 464(1982)的改性双酚-环氧树脂。环氧树脂与来自固体脂族胺、固体芳族胺、胺加合物、酚醛树脂,多元酸和已经所述的羧基官能聚酯类别的交联剂结合采用。要非常特别提及作为硬化剂的是双氰胺,其通常与催化剂如路易斯酸、三氟化硼-胺配合物、金属配合物、叔胺或季铵和咪唑啉衍生物,如2-甲基咪唑啉一起采用。
在本发明的粉末涂料组合物中精明地以大约化学计量数量采用树脂和交联剂。化学计量数量偏差超过30%在大多数情况下导致固化的涂料膜所需物理性能,例如柔韧性、冲击强度、粘合、耐候性或耐溶剂性的降低。
优选的粉末涂料组合物包括,作为进一步添加剂的,一种或多种如下的组分:颜料、染料、填料、蜡、流平助剂、脱气剂、电荷控制剂、荧光增白剂、粘合促进剂、抗氧剂、光稳定剂、固化催化剂或光敏引发剂。粉末涂料组合物也可包括缓蚀剂,例如抗腐蚀颜料,如含磷酸酯或硼酸酯的颜料或金属氧化物颜料,或其它有机或无机缓蚀剂,例如硝基间苯二甲酸、磷酸酯、技术级胺或取代的苯并三唑的盐。
用于可辐射固化的粉末涂料组合物的合适光敏引发剂,其中该组合物例如采用UV光固化,是基于二苯酮、乙醛酸苯酯、双-和/或单-酰基膦氧化物、α-羟基酮或苯偶酰二甲基缩酮的那些。作为光源精明地采用中压或高压汞灯。以下给出可辐射固化的涂料组合物的更详细描述。
脱气剂的例子是如在EP-A-0 471 409中描述的脂肪酸酰胺、ε-己内酰胺、间苯二甲酸甲酯和间苯二甲酸二甲酯(EP-A-284 996)和非常特别地苯偶姻。
常规流平助剂的例子是环氧化脂肪酸、松香醇、聚甲基丙烯酸月桂酯、聚丙烯酸月桂酯、聚二甲基硅氧烷-聚烯化氧嵌段共聚物或特别地,丙烯酸C1-C8烷基酯或甲基丙烯酸烷基酯的低分子量聚合物和共聚物。
粘合促进剂基于,例如改性硅烷、钛酸酯或锆酸酯。
荧光增白剂的例子是UvitexOB(Ciba Specialty Chemicals)。
颜料是,例如二氧化钛、氧化铁、炭黑、铝青铜、酞菁蓝或氨基蒽醌。
填料的例子是滑石、氧化铝、硅酸铝、磷酸铝、重晶石、云母、锌钡白、二氧化硅、碳酸钙或碳酸镁、氧化镁、氧化锌、碳酸锌、磷酸锌或其混合物。
按照a3)提及的可辐射固化的成膜粘结剂树脂除上述粉末涂料以外,典型地以下给出烯属不饱和单体或低聚物例子。
可辐射固化组合物的不饱和化合物可包含一个或多个烯属不饱和双键。它们可以是更低分子量(单体类)或更高分子量(低聚物类)。含有双键的单体的例子是丙烯酸和甲基丙烯酸羟烷基酯,如丙烯酸或甲基丙烯酸2-羟乙酯。进一步的例子是丙烯酰胺、甲基丙烯酰胺、N-取代(甲基)丙烯酰胺和丙烯酸或甲基丙烯酸。
含有多于一个双键的单体的例子是二丙烯酸丙二醇酯、二丙烯酸二丙二醇酯、二丙烯酸碱丙二醇酯、二丙烯酸新戊二醇酯、二丙烯酸六亚甲基二醇酯、三丙烯酸季戊四醇酯、三(羟乙基)异氰脲酸酯三丙烯酸酯(Sartomero 368;Cray Valley)。
也可以在可辐射固化体系中使用烷氧基化多元醇的丙烯酸酯,例如甘油乙氧基化物二丙烯酸酯、甘油丙氧基化物二丙烯酸酯、季戊四醇丙氧基化物三丙烯酸酯、季戊四醇丙氧基化物四丙烯酸酯、新戊二醇乙氧基化物二丙烯酸酯或新戊二醇丙氧基化物二丙烯酸酯。使用的多元醇的烷氧基化程度可变化。
另外含有极性基团,如-OH、-COOH或NH2的更高分子量(低聚物类)多不饱和化合物的例子是丙烯酸酯环氧树脂、含丙烯酸酯或乙烯基醚或环氧基团的聚酯、聚氨酯和聚醚。不饱和低聚物的进一步例子是不饱和聚酯树脂,其通常从马来酸,邻苯二甲酸和一种或多种二元醇生产,而且分子量为500-3000。此外也可以使用乙烯基醚单体和低聚物,和同样含有聚酯、聚氨酯、聚醚、聚乙烯基醚和环氧化物主链的马来酸酐封端的低聚物。特别地,如在WO90/01512中所述的带有乙烯基醚基团的低聚物和聚合物的组合是非常合适的,但也可考虑由马来酸和乙烯基醚官能化的单体的共聚物。这样的不饱和低聚物也可以称为预聚物。
特别合适的是,例如烯属不饱和羧酸和多元醇或聚环氧化物的酯,和在链或侧基中含有烯属不饱和基团的聚合物,如不饱和聚酯、聚酰胺和聚氨酯及其共聚物。
不饱和羧酸的例子是丙烯酸、甲基丙烯酸、巴豆酸、衣康酸、肉桂酸和不饱和脂肪酸如亚麻酸或油酸。优选是丙烯酸和甲基丙烯酸。
合适的多元醇是芳族和特别地脂族和环脂族多元醇。芳族多元醇的例子是对苯二酚、4,4′-二羟基二苯基、2,2-二(4-羟基苯基)丙烷、酚醛清漆和甲阶段酚醛树脂。聚环氧化物的例子是基于该多元醇,特别是芳族多元醇和环氧氯丙烷。也合适作为多元醇的是在聚合物链或侧基中包含羟基的聚合物和共聚物,如聚乙烯醇及其共聚物,或聚甲基丙烯酸羟烷基酯或其共聚物。进一步合适的多元醇是含有羟基端基的低聚酯。
脂族和环脂族多元醇的例子包括优选含有2-12个碳原子的亚烷基二醇,如乙二醇、1,2-或1,3-丙二醇、1,2-、1,3-或1,4-丁二醇、戊二醇、己二醇、辛二醇、十二烷二醇、二甘醇、三甘醇、分子量优选为200-1500的聚乙二醇、1,3-环戊烷二醇、1,2-、1,3-或1,4-环己烷二醇、1,4-二羟基甲基环己烷、甘油、三(β-羟乙基)胺、三羟甲基乙烷、三羟甲基丙烷、季戊四醇、二季戊四醇和山梨醇。
多元醇由一种或不同饱和羧酸部分酯化。
酯的例子是:
季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯、二季戊四醇丙烯酸酯、二季戊四醇三丙烯酸酯、二季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、季戊四醇二甲基丙烯酸酯、季戊四醇三甲基丙烯酸酯、二季戊四醇二甲基丙烯酸酯、二季戊四醇四甲基丙烯酸酯、季戊四醇二衣康酸酯、二季戊四醇三衣康酸酯、山梨醇三丙烯酸酯、山梨醇四丙烯酸酯、季戊四醇改性的三丙烯酸酯、山梨醇四丙烯酸酯、山梨醇五丙烯酸酯、低聚酯丙烯酸酯和甲基丙烯酸酯、甘油二丙烯酸酯。
也合适作为组分的是相同或不同不饱和羧酸和优选含有2-6个,特别是2-4个氨基的芳族、环脂族和脂族多元胺的酰胺。这样多元胺的例子是乙二胺、1,2-或1,3-丙二胺、1,2-、1,3-或1,4-丁二胺、1,5-戊二胺、1,6-己二胺、辛二胺、十二烷二胺、1,4-二氨基-环己烷、异佛尔酮二胺、苯二胺、双苯二胺、二-β-氨基乙基醚、二亚乙基三胺、三亚乙基四胺和二(β-氨基乙氧基)-和二(β-氨基丙氧基)-乙烷。进一步合适的多元胺是在侧链中含有另外氨基的聚合物和共聚物及含有氨基端基的低聚酰胺。这样不饱和酰胺的例子是:亚甲基双丙烯酰胺、1,6-六亚甲基双丙烯酰胺、二亚乙基三胺三甲基丙烯酰胺、双(甲基丙酰氨基丙氧基)乙烷、β-甲基丙烯酰氨基乙基甲基丙烯酸酯和N-[(β-羟基乙氧基)乙基]-丙烯酰胺。
特别优选是丙烯酸、单丙烯酸己二醇酯、三丙烯酸季戊四醇酯、二丙烯酸季戊四醇酯、单丙烯酸季戊四醇酯、丙烯酸2-羟乙酯、丙烯酸羟丙酯、三(丙二醇)甘油化物二丙烯酸酯、丙烯酸2,3-二羟丙酯、丙烯酸2,3-二羟丙酯、甘油1,3-二甘油化物二丙烯酸酯、单丙烯酸山梨醇酯、N-(2,3,4,5,6-五羟基-己基)-丙烯酰胺和对应的甲基丙烯酸及衍生物。
在本发明的上下文中术语(甲基)丙烯酸酯包括丙烯酸酯和甲基丙烯酸酯两者。丙烯酸酯或甲基丙烯酸酯化合物特别用作单或多烯属不饱和化合物。
适用于本发明的方法的光敏引发剂原则上是用电磁波照射时形成一个或多个自由基的任何化合物或混合物。这些包括含有多种引发剂的引发剂体系或彼此独立或协同起作用的体系。除助引发剂,例如胺、硫醇、硼酸酯、烯醇化物、膦、羧酸酯和咪唑以外,也可以使用敏化剂,例如吖啶、不吨、噻嗪、香豆素、噻吨酮、三嗪和染料。所述化合物和引发剂体系的描述可以发现于,如Crivello J.V.,DietilkerK.K.,(1999);涂料,油墨&油漆的UV & EB配制的化学&技术,以及Bradley G.(ed.)Vol.3:自由基和阳离子聚合的光敏引发剂第2版,John Wiley & Son Ltd。在步骤b)中适于本发明方法的光敏引发剂可以是含有或不含有不饱和基团的引发剂。
这样的化合物和衍生物是,例如衍生自如下类别的化合物:苯偶姻、苯偶酰缩酮、苯乙酮、苯羟烷基酮、苯氨基烷基酮、酰基膦氧化物、酰基膦硫化物、酰氧基亚氨基酮、烷基氨基取代的酮,如米希勒酮、过氧化合物、二腈化合物、氢化苯乙酮、苯基乙醛酸酯、二聚体苯基乙醛酸酯、二苯酮、肟和肟酯、噻吨酮、香豆素、二茂铁、钛茂、盐、锍盐、碘盐、重氮盐、硼酸酯、三嗪、双咪唑、聚硅烷和染料。也可以使用来自所提及类别化合物的化合物与彼此的组合,以及与对应助引发剂体系和/或敏化剂的组合。
以下提及单个光敏引发剂的典型例子,它们可以单独或与彼此的混合物使用。例如,二苯酮、二苯酮衍生物、苯乙酮、苯乙酮衍生物,例如α-羟基-环烷基苯基酮或2-羟基-2-甲基-1-苯基-丙酮、二烷氧基苯乙酮、α-羟基-或α-氨基-苯乙酮,例如(4-甲基硫代苯甲酰基)-1-甲基-1-吗啉代-乙烷、(4-吗啉代-苯甲酰基)-1-苄基-1-二甲基氨基-丙烷,(4-甲基-硫代苯甲酰基)-1-甲基-1-吗啉代-乙烷、(4-吗啉代-苯甲酰基)-1-(4-甲基-苄基)-1-二甲基氨基-丙烷、4-芳酰基-1,3-二氧戊环,苯偶姻烷基醚和苯偶酰缩酮,如苯偶酰二甲基缩酮、苯基乙醛酸酯及其衍生物、二聚体苯基乙醛酸酯、单酰基膦氧化物,例如(2,4,6-三甲基苯甲酰基)-苯基-膦氧化物、双酰基膦氧化物,例如双(2,6-二甲氧基苯甲酰基)-(2,4,4-三甲基-戊-1-基)膦氧化物、双(2,4,6-三甲基苯甲酰基)-苯基-膦氧化物或双(2,4,6-三甲基苯甲酰基)-(2,4-二戊氧基苯基)膦氧化物、三酰基膦氧化物、二茂铁化合物或钛茂,例如二环戊二烯基-双(2,6-二氟-3-吡咯并-苯基)-钛和硼酸盐。
作为助引发剂可以考虑,例如转换或加宽光谱敏感性和因此带来光聚合促进的敏化剂。它们特别是芳族羰基化合物,例如二苯酮、噻吨酮,特别是异丙基噻吨酮、蒽醌和3-酰基香豆素衍生物、三联苯、苯乙烯基酮,和3-(芳酰基亚甲基)-噻唑啉、樟脑醌,以及曙红、若丹明和赤藓红染料。
当根据本发明接种上的光敏引发剂层包含二苯酮或二苯酮衍生物时,例如胺可以考虑为光敏化剂。
光敏化剂的进一步例子是
1.噻吨酮
噻吨酮、2-异丙基噻吨酮、2-氯噻吨酮、2-十二烷基噻吨酮、2,4-二乙基噻吨酮、2,4-二甲基噻吨酮、1-甲氧基羰基噻吨酮、2-乙氧基-羰基噻吨酮、3-(2-甲氧基乙氧基羰基)-噻吨酮、4-丁氧基羰基噻吨酮、3-丁氧基羰基-7-甲基噻吨酮、1-氰基-3-氯噻吨酮、1-乙氧基-羰基-3-氯噻吨酮、1-乙氧基羰基-3-乙氧基噻吨酮、1-乙氧基羰基-3-氨基噻吨酮、1-乙氧基羰基-3-苯基磺酰基噻吨酮、3,4-二[2-(2-甲氧基-乙氧基)乙氧基羰基]噻吨酮、1-乙氧基羰基-3-(1-甲基-1-吗啉代乙基)-噻吨酮、2-甲基-6-二甲氧基甲基-噻吨酮、2-甲基-6-(1,1-二甲氧基苄基)-噻吨酮、2-吗啉代甲基噻吨酮、2-甲基-6-吗啉代甲基噻吨酮、N-烯丙基噻吨酮-3,4-二羧酰胺、N-辛基噻吨酮-3,4-二羧酰胺、N-(1,1,3,3-四甲基丁基)-噻吨酮-3,4-二羧酰胺、1-苯氧基噻吨酮、6-乙氧基羰基-2-甲氧基噻吨酮、6-乙氧基羰基-2-甲基噻吨酮、噻吨酮-2-聚乙二醇酯、2-羟基-3-(3,4-二甲基-9-氧代-9H-噻吨酮-2-基氧基)-N,N,N-三甲基-1-氯化丙烷胺;
2.二苯酮
二苯酮,4-苯基二苯酮,4-甲氧基二苯酮,4,4′-二甲氧基二苯酮,4,4′-二甲基二苯酮,4,4′-二氯二苯酮,4,4′-二甲基氨基-二苯酮,4,4′-二乙基氨基二苯酮,4-甲基二苯酮,2,4,6-三甲基-二苯酮,4-(4-甲基硫代苯基)-二苯酮,3,3′-二甲基-4-甲氧基二苯酮,甲基-2-苯甲酰基苯甲酸酯,4-(2-羟基乙基硫代)-二苯酮,4-(4-甲苯基硫代)-二苯酮、4-苯甲酰基-N,N,N-三甲基苯氯化甲烷胺、2-羟基-3-(4-苯甲酰基苯氧基)-N,N,N-三甲基-1-氯化丙烷胺一水合物、4-(13-丙酰氧基-1,4,7,10,13-五氧杂十三烷基)-二苯酮,4-苯甲酰基-N,N-二甲基-N-[2-(1-氧代-2-丙烯基)氧]乙基-苯甲烷胺氯化物。
3.3-酰基香豆素
3-苯甲酰基香豆素、3-苯甲酰基-7-甲氧基香豆素、3-苯甲酰基-5,7-二(丙氧基)香豆素、3-苯甲酰基-6,8-二氯香豆素、3-苯甲酰基-6-氯香豆素、3,3’-羰基-双[5,7-二(丙氧基)香豆素]、3,3’-羰基-双(7-甲氧基香豆素)、3,3’-羰基-双(7-二乙基氨基香豆素)、3-异丁酰基香豆素、3-苯甲酰基-5,7-二甲氧基香豆素、3-苯甲酰基-5,7-二乙氧基香豆素、3-苯甲酰基-5,7-二丁氧基香豆素、3-苯甲酰基-5,7-二(甲氧基乙氧基)香豆素、3-苯甲酰基-5,7-二(烯丙氧基)香豆素、3-苯甲酰基-7-二甲基氨基香豆素、3-苯甲酰基-7-二乙基氨基香豆素、3-异丁酰基-7-二甲基氨基香豆素、5,7-二甲氧基-3-(1-萘甲酰基)-香豆素、5,7-二甲氧基-3-(1-萘甲酰基)-香豆素、3-苯甲酰基苯并[f]香豆素、7-二乙基氨基-3-噻吩酰基香豆素、3-(4-氰基苯甲酰基)-5,7-二甲氧基香豆素;
4.3-(芳酰基亚甲基)-噻唑啉
3-甲基-2-苯甲酰基亚甲基-β-萘并噻唑啉,3-甲基-2-苯甲酰基亚甲基-苯并噻唑啉、3-乙基-2-丙酰基亚甲基-β-萘并噻唑啉;
5.其它羰基化合物
苯乙酮、3-甲氧基苯乙酮、4-苯基苯乙酮、苯偶酰、2-乙酰基萘、2-萘醛、9,10-蒽醌、9-芴酮、二苯并环庚酮、不吨酮、2,5-双(4-二乙基氨基亚苄基)环戊酮、α-(对二甲基氨基亚苄基)-酮,如2-(4-二甲基氨基-亚苄基)-茚满-1-酮或3-(4-二甲基氨基-苯基)-1-茚满-5-基-丙酮、3-苯基硫代邻苯二甲酰亚胺、N-甲基-3,5-二(乙基硫代)邻苯二甲酰亚胺、N-甲基-3,5-二(乙基硫代)邻苯二甲酰亚胺。
典型的单个光敏引发剂浓度为0.01%-5wt%,基于粘结剂树脂和单体的重量。
作为组分c)可以存在任选地水和/或有机溶剂。合适的有机溶剂原则上是其中粘合剂组分是可溶的任何物质。在水的情况下,提供乳液或分散体。合适的溶剂是,例如醇,如乙醇、丙醇、异丙醇、丁醇、乙二醇,酮,如丙酮、甲乙酮、乙腈,芳族烃,如甲苯和二甲苯,酯和醛,如乙酸乙酯、甲酸乙酯、脂族烃,如石油醚、戊烷、己烷、环己烷,卤代烃,如二氯甲烷、氯仿,或者油、天然油、蓖麻油、植物油和同样合成油。此描述不是穷举和仅通过例子给出。
优选是包括如下物质的涂料组合物:
a2)一种或多种热交联成膜粘结剂树脂;或
a3)一种或多种可辐射固化的成膜粘结剂树脂。
进一步优选是包括如下物质的涂料组合物:
a2)一种或多种热交联成膜粘结剂树脂。
特别优选是包括如下物质的涂料组合物:
a2)一种或多种热交联成膜粘结剂树脂没有水和有机溶剂,它的形式为固体粉末。
此类型的涂料方便地称为已经说明的粉末涂料。
如上所述强制的是通式(I)的聚合物或共聚物组分b)流平剂由硝酰基介导的受控自由基聚合(CFRP)制备。Solomon等人在US4,581,429中首先描述了这样的方法。U.S.4,581,429公开了通过受控或″活″聚合物链生长的自由基聚合方法,其产生确定的低聚物均聚物和共聚物,包括嵌段和接枝共聚物。其中公开了部分通式R′R″N-O-X的引发剂的用途。在聚合方法中,产生了自由基R′R″N-O·和·X。·X是能够聚合包含亚乙基的单体单元的自由基基团,如叔丁基或氰基异丙基。
以上方法的变化公开于US 5 322 912,其中描述了自由基引发剂和基础结构R′R″N-O·的稳定自由基剂用于合成均聚物和嵌段共聚物的组合用途。
这些方法用于制备均聚物、无规、嵌段、渐变、接枝或梳形(共)聚合物,它们具有窄分子量分布和低的多分散性指数。
如先前所述必要的是(共)聚合物由硝酰基介导的受控自由基聚合(CFRP)获得。基本存在两种合适的途径:
b1)在含有结构组元
的烷氧基胺引发剂/调节剂化合物存
在下的聚合;和
合适的硝酰基醚和硝酰基自由基主要从US-A-4 581 429或EP-A-621 878中可知是已知的。特别有用的是在WO98/13392、WO99/03894和WO00/07981中描述的开链化合物,在WO99/67298和GB2335190中描述的哌啶衍生物或在GB2342649和WO96/24620中描述的杂环化合物。进一步合适的硝酰基醚和硝酰基自由基描述于WO02/4805和WO02/100831。
在分子中含有多于一个硝酰基的硝酰基醚和硝酰基自由基例如描述于US6,573,347、WO01/02345和WO03/004471中当制备支化、星型或梳形(共)聚合物时,这些化合物理想地是合适的。在此情况下上述通式(I)中的y和/或n大于1。
在本发明的上下文中,术语烷氧基胺和硝酰基醚用作同等物。
优选结构组元
和
是5或6-元杂环的一部分,该杂
环在环体系中含有另外的氮或氧原子。取代哌啶、吗啉和哌嗪衍生物是特别有用的。
其中G1,G2,G3,G4独立地是C1-C6烷基或G1和G2或G3和G4,或G1、G2、G3和G4一起形成C5-C12环烷基;
G5,G6独立地是H、C1-C18烷基、苯基、萘基或基团COOC1-C18烷基;
X选自-CH2-苯基、CH3CH-苯基、(CH3)2C-苯基、(C5-C6环烷基)2CCN、(CH3)2CCN、
-CH2CH=CH2、CH3CH- CH=CH2(C1-C4烷基)CR20-C(O)-苯基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷氧基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-N-二(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH2,其中
R20是氢或(C1-C4)烷基,和
*表示化合价。
特别地通式(II)的结构组元具有为A,B或O,
其中
m是1,
R是氢、未间隔或由一个或多个氧原子间隔的C1-C18烷基、氰基乙基、苯甲酰基、缩水甘油基、含有2-18个碳原子的脂族羧酸的单价基团、含有7-15个碳原子的环脂族羧酸的单价基团、或含有3-5个碳原子的α,β-不饱和羧酸的单价基团或含有7-15个碳原子的芳族羧酸的单价基团;
p是1;
R101是C1-C12烷基、C5-C7环烷基、C7-C8芳烷基、C2-C18烷酰基、C3-C5烯酰基或苯甲酰基;
R102是C1-C18烷基、C5-C7环烷基、未取代或由氰基、羰基或脲基团取代的C2-C8烯基,或是缩水甘油基、通式-CH2CH(OH)-Z的基团或通式-CO-Z或-CONH-Z的基团,其中Z是氢、甲基或苯基;
G6是氢,以及G5是氢或C1-C4烷基,
G1和G3是甲基和G2和G4是乙基或丙基,或G1和G2是甲基及G3和G4是乙基或丙基;和
X选自-CH2-苯基、CH3CH-苯基、(CH3)2C-苯基、(C5-C6环烷基)2CCN、(CH3)2CCN、
-CH2CH=CH2、CH3CH-CH=CH2(C1-C4烷基)CR20-C(O)-苯基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷氧基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-N-二(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH2,其中
R20是氢或(C1-C4)烷基。
以上化合物和它们的制备描述于GB2 335 190和GB2 361 235中。
另一组优选的硝酰基醚是通式(IIc)、(IId)、(IIe)、(IIf)、(IIg)或(IIh)的那些
其中R201,R202,R203和R204彼此独立地是C1-C18烷基、C3-C18烯基、C3-C18炔基、由OH、卤素或基团-O-C(O)-R205取代的C1-C18烷基、C3-C18烯基、C3-C18炔基,由至少一个O原子和/或NR205基团间隔的C2-C18烷基、C3-C12环烷基或C6-C10芳基或R201和R202和/或R203和R204与连接碳原子一起形成C3-C12环烷基;
R205,R206和R208独立地是氢、C1-C18烷基或C6-C10芳基;
R208是氢、OH、C1-C18烷基、C3-C18烯基、C3-C18炔基、由一个或多个OH、卤素或基团-O-C(O)-R205取代的C1-C18烷基、C3-C18烯基、C3-C18炔基、由至少一个O原子和/或NR205基团间隔的C2-C18烷基、C3-C12环烷基或C6-C10芳基、C7-C9苯基烷基、C5-C10杂芳基、-C(O)-C1-C18烷基、-O-C1-C18烷基或-COOC1-C18烷基;
R209,R210,R211和R212独立地是氢、苯基或C1-C18烷基;和
X选自-CH2-苯基、CH3CH-苯基、(CH3)2C-苯基、(C5-C6环烷基)2CCN、(CH3)2CCN、
-CH2CH=CH2、CH3CH-CH=CH2(C1-C4烷基)CR20-C(O)-苯基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷氧基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-N-二(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH2,其中
R20是氢或(C1-C4)烷基。
更优选在通式(Ic)、(Id)、(Ie)、(f)、(Ig)和(Ih)中,R201、R202、R203和R204的至少两个是乙基、丙基或丁基和剩余的是甲基;或
R201和R202或R203和R204与连接碳原子一起形成C5-C6环烷基,以及一个剩余的取代基是乙基、丙基或丁基。
最优选X是CH3CH-苯基。
以上化合物和它们的制备描述于GB2342649。
进一步合适的化合物是通式(III)的4-亚氨基化合物
其中G11、G12、G13和G14独立地是C1-C4烷基,或G11和G12一起及G13和G14一起,或G11和G12一起或G13和G14一起是五亚甲基;
G15和G16每个彼此独立地是氢或C1-C4烷基;
X如以上1所定义;
k是1、2、3或4
Y是O、NR302,或当n是1和R301表示烷基或芳基时,Y另外是直接键;
R302是H、C1-C18烷基或苯基;
如果k是1,
R301是H、直链或支化C1-C18烷基、C3-C18烯基或C3-C18炔基,其可以是未取代的或由一个或多个OH、C1-C8烷氧基、羧基、C1-C8烷氧基羰基取代,是C5-C12环烷基或C5-C12环烯基;
苯基、C7-C9苯基烷基或萘基,其可以是未取代的或由一个或多个C1-C8烷基、卤素、OH、C1-C8烷氧基、羧基、C1-C8烷氧基羰基取代;
-C(O)-C1-C36烷基、或含有3-5个碳原子的α,β-不饱和羧酸或含有7-15个碳原子的芳族羧酸的酰基部分;
-SO3-Q+、-PO(O-Q+)2、-P(O)(OR2)2、-SO2-R2、-CO-NH-R2、-CONH2、COOR2、或Si(Me)3,其中Q+是H+、铵或碱金属阳离子;
如果k是2,
R301是C1-C18亚烷基、C3-C18亚烯基或C3-C18亚炔基,其可以是未取代的或由一个或多个OH、C1-C8烷氧基、羧基、C1-C8烷氧基羰基取代;
或苯二甲基;或
R301是含有2-36个碳原子的脂族二羧酸,或含有8-14个碳原子的环脂族或芳族二羧酸的双酰基部分;
如果k是3,
R301是脂族、环脂族或芳族三羧酸的三价基团;和
如果k是4,R301是脂族、环脂族或芳族四羧酸的四价基团。
优选G16是氢,G15是氢或C1-C4烷基,特别是甲基,G11和G13是甲基及G12和G14是乙基或丙基,或G11和G12是甲基及G13和G14是乙基或丙基。
通式V的4亚氨基化合物可以例如根据E.G.Rozantsev,A.V.Chudinov,V.D.Sholle.:lzv.Akad.Nauk.SSSR,Ser.Khim.(9),2114(1980),从对应的4-氧代氧化亚氮开始在与羟基胺的缩合反应和OH基团的随后反应中制备。化合物描述于WO02/100831。
优选是化合物,其中通式(II′)的结构组元具有通式A′,B′或O′,
其中
m是1,
R是氢、未间隔或由一个或多个氧原子间隔的C1-C18烷基、氰基乙基、苯甲酰基、缩水甘油基、含有2-18个碳原子的脂族羧酸的单价基团、含有7-15个碳原子的环脂族羧酸的单价基团、或含有3-5个碳原子的α,β-不饱和羧酸的单价部分或含有7-15个碳原子的芳族羧酸的单价部分;
p是1;
R101是C1-C12烷基、C5-C7环烷基、C7-C8芳烷基、C2-C18烷酰基、C3-C5烯酰基或苯甲酰基;
R102是C1-C18烷基、C5-C7环烷基、未取代或由氰基、羰基或脲基团取代的C2-C8烯基,或是缩水甘油基、通式-CH2CH(OH)-Z或通式-共-Z或-CONH-Z的基团,其中Z是氢、甲基或苯基;
G6是氢,和G5是氢或C1-C4烷基,
G1和G3是甲基及G2和G4是乙基或丙基,或G1和G2是甲基及G3和G4是乙基或丙基。
也合适的是化合物,其中结构组元
具有通式(III′)
其中G11、G12、G13和G14独立地是C1-C4烷基,或G11和G12一起及G13和G14一起,或G11和G12一起或G13和G14一起是五亚甲基;
G15和G16每个彼此独立地是氢或C1-C4烷基;
k是1、2、3或4
Y是O、NR302,或当n是1和R301表示烷基或芳基时,Y另外是直接键;
R302是H、C1-C18烷基或苯基;
如果k是1,
R301是H、直链或支化C1-C18烷基、C3-C18烯基或C3-C18炔基,其可以是未取代的或由一个或多个OH、C1-C8烷氧基、羧基、C1-C8烷氧基羰基取代,是C5-C12环烷基或C5-C12环烯基;
苯基、C7-C9苯基烷基或萘基,其可以是未取代的或由一个或多个C1-C8烷基、卤素、OH、C1-C8烷氧基、羧基、C1-C8烷氧基羰基取代;
-C(O)-C1-C36烷基、或含有3-5个碳原子的α,β-不饱和羧酸或含有7-15个碳原子的芳族羧酸的酰基部分;
-SO3-Q+、-PO(O-Q+)2、-P(O)(OR2)2、-SO2-R2、-CO-NH-R2、-CONH2、COOR2、或Si(Me)3,其中Q+是H+、铵或碱金属阳离子;
如果k是2,
R301是C1-C18亚烷基、C3-C18亚烯基或C3-C18亚炔基,其可以是未取代的或由一个或多个OH、C1-C8烷氧基、羧基、C1-C8烷氧基羰基取代;
或苯二甲基;或
R301是含有2-36个碳原子的脂族二羧酸,或含有8-14个碳原子的环脂族或芳族二羧酸的双酰基部分;
如果k是3,
R301是脂族、环脂族或芳族三羧酸的三价基团;和
如果k是4,R301是脂族、环脂族或芳族四羧酸的四价基团。
各种取代基中的烷基可以是线性或支化的。包含1-18个碳原子的烷基的例子是甲基、乙基、丙基、异丙基、丁基、2-丁基、异丁基、叔丁基、戊基、2-戊基、己基、庚基、辛基、2-乙基己基、叔辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十六烷基和十八烷基。
3-18个碳原子的烯基是线性或支化基团,例如丙烯基、2-丁烯基、3-丁烯基、异丁烯基、n-2,4-戊二烯基、3-甲基-2-丁烯基、n-2-辛烯基、n-2-十二碳烯基、异十二碳烯基、油基、n-2-十八碳烯基或n-4-十八碳烯基。
优选是3-12个碳原子,特别优选3-6个碳原子的烯基。
3-18的炔基是线性或支化基团,例如丙炔基(-CH2-C≡CH)、2-丁炔基、3-丁炔基、n-2-辛炔基、或n-2-十八碳炔基。优选是3-12个碳原子,特别优选3-6个碳原子的炔基。
羟基取代的烷基的例子是羟基丙基、羟基丁基或羟基己基。
卤素取代的烷基的例子是二氯丙基、单氯丁基或三氯己基。
由至少一个O原子间隔的C2-C18烷基是例如-CH2-CH2-O-CH2-CH3、-CH2-CH2-O-CH3-或-CH2-CH2-O-CH2-CH2-CH2-O-CH2-CH3-。其优选衍生自聚乙二醇。通用描述是-((CH2)a-O)b-H/CH3,其中a是1-6的数字和b是2-10的数字。
由至少一个NR5基团间隔的C2-C18烷基可以描述为-((CH2)a-NR5)b-H/CH3,其中a,b和R5如上所定义。
C3-C12环烷基典型地是环丙基、环戊基、甲基环戊基、二甲基环戊基、环己基、甲基环己基或三甲基环己基。
C6-C10芳基例如是苯基或萘基,但也是C1-C4烷基取代苯基、C1-C4烷氧基取代苯基、羟基、卤素或硝基取代苯基。烷基取代苯基的例子是乙苯、甲苯、二甲苯和其异构体、1,3,5-三甲苯或异丙苯。卤素取代苯基例如是二氯苯或溴甲苯。
烷氧基取代基典型地是甲氧基、乙氧基、丙氧基或丁氧基和它们的对应异构体。
C7-C9苯基烷基是苄基、苯基乙基或苯基丙基。
C5-C10杂芳基例如是吡咯、吡唑、咪唑、2,4二甲基吡咯、1-甲基吡咯、噻吩、呋喃、糖醛、吲哚、苯并呋喃、唑、异唑、异噻唑、三唑、呲啶、α-甲基呲啶、哒嗪、呲嗪或嘧啶。
如果R是羧酸的单价基团,其例如是乙酰基、丙酰基、丁酰基、戊酰基、己酰基、硬脂酰基、月桂酰基、丙烯酰基、甲基丙烯酰基、苯甲酰基、肉桂酰基或β(3,5-二-叔丁基-4-羟基苯基)丙酰基。
C1-C18烷酰基是例如,甲酰基、丙酰基、丁酰基、辛酰基、十二烷酰基,但优选是乙酰基,以及C3-C5烯酰基特别是丙烯酰基。
特别地聚合工艺b1)是非常合适的。当使用工艺b1)时,根据以上说明的结构,硝酰基醚在O-X键之间断开。通式(I)中的片段(E)则对应于O-N片段和引发片段(In)对应于基团X的C中心基团。
特别合适的硝酰基醚和硝酰基自由基是如下通式的那些:
在本发明的具体实施方案中,聚合物或共聚物流平剂采用通式
(O1)的化合物制备
当选择根据途径b2)的方法时,引发片段(In)对应于衍生自自由基引发剂的基团。途径b2)的自由基引发剂优选是偶氮化合物、过氧化物、过酸酯或氢过氧化物。
具体优选的基源是2,2′-偶氮二异丁腈,2,2′-偶氮双(2-甲基-丁腈)、2,2′-偶氮双(2,4-二甲基戊腈)、2,2′-偶氮双(4-甲氧基-2,4-二甲基戊腈)、1,1′-偶氮双(1-环己烷腈)、2,2′-偶氮双(异丁酰胺)二水合物、2-苯基偶氮-2,4-二甲基-4-甲氧基戊腈、二甲基-2,2′-偶氮二异丁酸酯、2-(氨基甲酰基偶氮)异丁腈、2,2′-偶氮双(2,4,4-三甲基戊烷)、2,2′-偶氮双(2甲基丙烷)、2,2′-偶氮双(N,N′-二亚甲基异丁酰脒),游离碱或盐酸盐、2,2′-偶氮双(2-脒基丙烷)、游离碱或盐酸盐,2,2′-偶氮双{2-甲基-N-[1,1-双(羟基甲基)乙基]丙酰胺}或2,2′-偶氮双{2-甲基-N-[1,1-双(羟基甲基)-2-羟基乙基]丙酰胺;乙酰基环己烷磺酰基过氧化物、过氧二碳酸二异丙酯、过新癸酸叔戊酯、过新癸酸叔丁酯、过新戊酸叔丁酯、过新戊酸叔戊酯、双(2,4-二氯苯甲酰基)过氧化物、二异壬酰基过氧化物、二癸酰基过氧化物、二辛酰基过化物、二月桂酰基过氧化物、双(2-甲基苯甲酰基)过氧化物、二琥珀酸过氧化物、过氧化二乙酰、过氧化二苯甲酰、过2-乙基己酸叔丁酯、双-(4-氯苯甲酰基)-过氧化物、过异丁酸叔丁酯、过马来酸叔丁酯、1,1-双(叔丁基过氧)3,5,5-三甲基环己烷、1,1-双(叔丁基过氧)环己烷,叔丁基过氧异丙基碳酸酯、过异壬酸叔丁酯、2,5-二甲基己烷2,5-二苯甲酸酯、过乙酸叔丁酯、过苯甲酸叔戊酯、过苯甲酸叔丁酯、2,2-双(叔丁基过氧)丁烷、2,2双(叔丁基过氧)丙烷、过氧化二枯基、2,5-二甲基己烷-2,5-二-叔丁基过氧化物、3-叔丁基过氧3-苯基苯酞、过氧化二叔戊基、α,α′-双(叔丁基过氧异丙基)苯、3,5-双(叔丁基过氧)3,5-二甲基1,2-二氧戊环、二-叔丁基过氧化物、2,5-二甲基己炔-2,5-二-叔丁基过氧化物、3,3,6,6,9,9-六甲基1,2,4,5-四氧杂环壬烷、对薄荷烷氢过氧化物、蒎烷氢过氧化物、二异丙基苯单-α-氢过氧化物、氢过氧化枯烯或氢过氧化叔丁基。
基团E不必须是稳定硝酰基自由基,其通过氧原子结合到聚合物或共聚物。它也可以是来自如下方式的基团:连接的稳定硝酰基自由基的取代或消除反应。
为了在链端另一个基团的引入或使硝酰基封端的聚合物为非反应性的,存在几种可能性以除去或交换氧化亚氮(NO*)。以下给出一些具体的例子。
氧化亚氮链端可以如由化合物的使用而交换,该化合物可以在均裂时产生自由基如四苯基乙烷类产物。氧化亚氮链端的交换通过如下方式进行:在如四苯基乙烷衍生物的存在下加热聚合物直到在开放和密闭链端之间的平衡是活性的温度。氧化亚氮和均裂四苯基乙烷衍生物的交换发生。例如,Beyou,E.;Jarroux,N.;Zydowicz,N.;Chaumont,P.Macromol.Chem.Phys.2001,202,974-79(氧化亚氮-或溴封端的聚苯乙烯的官能端基交换)对此进行了描述。
氧化亚氮链端也可以由Zn/乙酸的使用在链端的OH基团形成下除去。Chessa,G.;Scrivanti,A.;Matteoli,U.;Castelvetro,V.Polymer2001,42,9347-53(通过活/受控自由基聚合合成三和六臂聚苯乙烯)对此进行了描述。
进一步的可能性是使用不能容易地通过自由基聚合而均聚的不饱和化合物。例子是单体,如马来酸酐、马来酰亚胺、n-取代马来酰亚胺、马来酸酯、富马酸酯、α-甲基苯乙烯、富马酸二烷基酯,或非活化烯烃,如异丁烯、环己烯、1-辛烯或异构体、烷基烯丙基醚、烷基酯。将这样的不饱和化合物优选在单体的消耗和/或除去之后加入NO*-封端的聚合物,其在硝酰基介导的聚合中是反应性的。然后将NO*-封端的聚合物和非聚合反应性不饱和化合物加热到如100-150℃的高温足以使聚合物对进一步的链增长为非活性的时间。不受任何理论约束,相信由采用非反应性单体的后处理,所有或大多数NO*-基团从聚合物断裂,以及一个或仅几个非反应性不饱和化合物的单元在聚合物链端插入。用于这样后处理官能化的具体例子是在双键的形成下采用马来酸酐和马来酰亚胺的反应,Harth,E.;Hawker,C.J.;Fan,W;Waymouth,R.M.Macromolecules 2001,34(12),3856-62(氧化亚氮-介导的″活″自由基聚合中的链端官能化)对此进行了描述。
然而另一种可能性是使用可以在链端诱导碎裂的化合物,如通过在氧化亚氮介导的自由基聚合中使用甲基丙烯酸酯。丙烯酸类聚合物的氧化亚氮链端可以由如下方式除去:采用如过量甲基丙烯酸甲酯在开放和密闭链端之间的平衡是活性的温度下加热。链端的双键形成和氧化亚氮的脱除可以观察到,如由Cheng,C.;Yang,N.-L.PolymerPreprints 2003,41(1),1010-11 C.Burguiere,M.-A.Dourges,B.Charleux,J.-P.Vairon,Macromolecules,1999,32,3883-3890描述。
从由氧化亚氮介导的受控自由基聚合制备的聚合物消除NO*的简单方法是在反应性单体的脱除之后加热到高温。这导致聚合物,它对于进一步硝酰基介导的聚合是非活性的。不由理论约束,相信由这样的热后处理将NO*基团消除或从聚合物交换。
由各种方法引入的基团的例子是-OH、-CR=CR2、-O-C(O)-CR=CH2。
优选组分b)流平剂的多分散性为1.0-2.0,更优选1.1-1.5。
例如组分b)流平剂的玻璃化转变温度为20℃-200℃,特别地30℃-150℃。
在优选的实施方案中组分b)流平剂包含至少30%丙烯酸叔丁酯和/或甲基丙烯酸叔丁酯,基于总单体的重量,特别地大于50wt%。
例如组分b)流平剂是线性聚合物或共聚物,即在通式(I)中n是1。
优选在通式(I),组分b)中,y是1。
例如组分b)流平剂的分子量为1000-100000,优选3000-50000g/mol(道尔顿)。
优选是涂料组合物其中组分b)流平剂包含至少30%,更优选至少50wt%丙烯酸叔丁酯和/或甲基丙烯酸叔丁酯,和0.5-50%,更优选1-20%官能单体,该官能单体选自丙烯酸、甲基丙烯酸、丙烯酸(C1-C6)羟烷基酯、甲基丙烯酸(C1-C6)羟烷基酯、丙烯酸(C1-C6)烷基酯和甲基丙烯酸(C1-C6)烷基酯,它们由氨基、(C1-C6)烷基氨基、(C1-C6)二烷基氨基、环氧、氟、全氟或硅氧烷基团取代。
在本发明的具体实施方案中组分b)流平剂包含至少50wt%丙烯酸叔丁酯和/或甲基丙烯酸叔丁酯和在室温下为固体。
优选组分b)流平剂存在的数量为0.1-15%,更优选0.1-10%和最优选0.1-3wt%,基于成膜粘结剂树脂,组分a)的重量。
在其它优选的实施方案中,组分b)流平剂包括至少两种不同的单体M和结构组元(M)x中的序列结构是不同单体的二嵌段,多嵌段或渐变嵌段状布置。
仍然在另一个优选的实施方案中,组分b)流平剂包括至少一种多官能单体,由该多官能单体结构组元(M)x中的聚合物链导致支化聚合物链结构和y>1。在可辐射固化的涂料的上下文中提及典型的多官能单体。
多官能单体包括具有至少两个不饱和双键的化合物,它能够在受控的自由基聚合期间共聚。依赖于多官能单体的反应性和使用数量,这导致从引发剂片段In生长的聚合物链(M)x的各种支化程度。
多官能单体的典型例子是二丙烯酸乙二醇酯、二甲基丙烯酸乙二醇酯、二丙烯酸1,4-丁二醇酯、二甲基丙烯酸1,4-丁二醇酯、三羟甲基丙烷三丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、甲基丙烯酸烯丙酯、1,4-二乙烯基苯、二丙烯酸1,6-己二醇酯、二丙烯酸三丙二醇酯、乙氧基化三羟甲基丙烷三丙烯酸酯、乙氧基化双酚-A二丙烯酸酯。
涂料组合物可包含另外的添加剂,如光稳定剂,热稳定剂,颜料和填料。以下给出另外添加剂的例子。
1.抗氧剂
1.1.烷基化一元酚,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,在侧链中是线性或支化的壬基苯酚,例如2,6-二-壬基-4-甲基苯酚,2,4-二甲基-6-(1′-甲基十一碳-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十七碳-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十三碳-1′-基)苯酚及其混合物。
1.2.烷基硫代甲基苯酚,例如2,4-二辛基硫代甲基-6-叔丁基苯酚,2,4-二辛基硫代甲基-6-甲基苯酚,2,4-二辛基硫代甲基-6-乙基苯酚,2,6-二-十二烷基硫代甲基-4-壬基苯酚。
1.3.对苯二酚和烷基化对苯二酚,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-3-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.烷叉基双酚,例如2,2′-亚甲基双(6-叔丁基-4-甲基苯酚),2,2′-亚甲基双(6-叔丁基-4-乙基苯酚),2,2′-亚甲基双[4-甲基-6-(α-甲基环己基)-苯酚],2,2′-亚甲基双(4-甲基-6-环己基苯酚),2,2′-亚甲基双(6-壬基-4-甲基苯酚),2,2′-亚甲基双(4,6-二-叔丁基苯酚),2,2′-亚乙基双(4,6-二-叔丁基苯酚),2,2′-亚乙基双(6-叔丁基-4-异丁基苯酚),2,2′-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚],2,2′-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4′-亚甲基双(2,6-二-叔丁基苯酚),4,4′-亚甲基双(6-叔丁基-2-甲基苯酚),1,1-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷,2,6-双(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-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷,乙二醇双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸酯,双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯,双[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-双-(3,5-二甲基-2-羟基苯基)丁烷,2,2-双(3,5-二-叔丁基-4-羟基苯基)丙烷,2,2-双-(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,双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯,双(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.羟基苄基化丙二酸酯,例如双十八烷基-2,2-双( 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,二-十二烷基巯基乙基-2,2-双(3,5-二-叔丁基-4-羟基苄基)丙二酸酯,双[4-(1,1,3,3-四甲基丁基)苯基]-2,2-双(3,5-二-叔丁基-4-羟基苄基)丙二酸酯。
1.9.芳族羟基苄基化合物,例如1,3,5-三(3,5-二-叔丁基-4-羟基-苄基)-2,4,6-三甲基苯,1,4-双(3,5-二-叔丁基-4-羟基苄基)-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-双(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-双(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-双(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-苯基丙酰基)-六氢-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟基苄基)异氰脲酸酯。
1.11.苄基膦酸酯,例如二甲基-2,5-二-叔丁基-4-羟基苄基膦酸酯,二乙基-3,5-二-叔丁基-4-羟基苄基膦酸酯,双十八烷基3,5-二-叔丁基-4-羟基苄基膦酸酯,双十八烷基-5-叔丁基-4-羟基-3-甲基苄基膦酸酯,3,5-二-叔丁基-4-羟基苄基膦酸的单乙基酯的钙盐。
1.12.酰基氨基苯酚,例如4-羟基月桂酰苯胺,4-羟基硬脂酰苯胺,辛基N-(3,5-二-叔丁基-4-羟基苯基)氨基甲酸酯。
1.13.β-(3,5-二-叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯,如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇,1,9-壬二醇、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(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基1-丙烷,4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯;
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯,如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇,1,9-壬二醇、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(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基1-丙烷,4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷;3,9-双[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5.5]-十一烷的酯。
1.15.β-(3,5-二环己基-4-羟苯基)丙酸与一元醇或多元醇的酯,如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇,1,9-壬二醇、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(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基1-丙烷,4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯;
1.16.3,5-二-叔丁基-4-羟苯基乙酸与一元醇或多元醇的酯,如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇,1,9-壬二醇、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(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基1-丙烷,4-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯。
1.17.β-(3,5-二-叔丁基-4-羟苯基)丙酸的酰胺如N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺,N,N′-双(3,5-二-叔丁基-4-羟基-苯基丙酰基)三亚甲基二酰胺,N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)酰肼,N,N′-双[2-(3-[3,5-二-叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺(Nau-gardXL-1,提供商Uniroyal)。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧剂,例如N,N′-二-异丙基-对苯二胺,N,N′-二-仲丁基-对苯二胺,N,N′-双(1,4-二甲基戊基)-对苯二胺,N,N′-双(1-乙基-3-甲基戊基)-对苯二胺,N,N′-双(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′-双(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-(对甲苯氨磺酰基)二苯基胺,N,N′-二甲基-N,N′-二-仲丁基-对苯二胺,二苯基胺,N-烯丙基二苯基胺,4-异丙氧基二苯基-胺,N-苯基-1-萘基胺,N-(4-叔辛基苯基)-1-萘基胺,N-苯基-2-萘基胺,辛基化二苯基胺,例如p,p′-二-叔辛基二苯基胺,4-正丁基-氨基苯酚,4-丁酰基氨基苯酚,4-壬酰基氨基苯酚,4-十二烷酰基氨基苯酚,4-十八烷酰基氨基苯酚,双(4-甲氧基苯基)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-双[(2-甲基苯基)氨基]乙烷,1,2-双(苯基-氨基)丙烷,(邻甲苯基)双胍,双[4-(1′,3′-二甲基丁基)苯基]胺,叔辛基化N-苯基-萘基胺、单和二烷基化叔丁基/叔辛基二苯基胺的混合物、单和二烷基化壬苯二苯基胺的混合物、单和二烷基化十二烷基二苯基胺的混合物、单和二烷基化异丙基/异己基二苯基胺的混合物、单和二烷基化叔丁二苯基胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单和二烷基化叔丁基/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-双(2,2,6,6-四甲基哌啶-4-基六亚甲基二胺、双(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′-羟苯基)苯并三唑,例如2-(2′-羟基-5′-甲基苯基)苯并三唑,2-(3′,5′-二-叔丁基-2′-羟基苯基)苯并三唑,2-(5′-叔丁基-2′-羟基苯基)苯并三唑,2-(2′-羟基-5′-(1,1,3,3-四甲基丁基)苯基)苯并三唑,2-(3′,5′-二-叔丁基-2′-羟基苯基)-5-氯苯并三唑,2-(3′-叔丁基-2′-羟基-5′-甲基苯基)-5-氯苯并三唑,2-(3′-仲丁基-5′-叔丁基-2′-羟基苯基)苯并三唑,2-(2′-羟基-4′-辛氧基苯基)苯并三唑,2-(3′,5′-二-叔戊基-2′-羟基苯基)苯并三唑,2-(3′,5′-双(α,α-二甲基苄基)-2’-羟苯基)苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并三唑,2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟苯基)-5-氯苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)苯并三唑,2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟苯基)苯并三唑,2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并三唑,2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基苯并三唑,2,2’-亚甲基双[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;d中R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-2-基苯基,2-[2’-羟基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)苯基]苯并三唑;2-[2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)苯基]苯并三唑。
2.2.2-羟基二苯酮,例如4-羟基,4-甲氧基,4-辛氧基,4-癸氧基,4-十二烷氧基,4-苄氧基,4,2’,4’-三羟基和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,例如水杨酸4-叔丁基苯酯,水杨酸苯酯,水杨酸辛基苯酯,二苯甲酰基间苯二酚,双(4-叔丁基苯甲酰基)间苯二酚,苯甲酰基间苯二酚,3,5-二-叔丁基-4-羟基苯甲酸2,4-二-叔丁基苯酯,3,5-二-叔丁基-4-羟基苯甲酸十六烷基酯,3,5-二-叔丁基-4-羟基苯甲酸十八烷基酯,3,5-二-叔丁基-4-羟基苯甲酸2-甲基-4,6-二-叔丁基苯酯。
2.4.丙烯酸酯,例如α-氰基-β,β-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-对甲氧基肉桂酸甲酯,α-氰基-β-甲基-对甲氧基肉桂酸丁酯,α-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′-硫代双[4-(1,1,3,3-四甲基-丁基)苯酚]的镍配合物,如1∶1或1∶2配合物,采用或不采用另外的配体如正丁基胺,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,如甲基或乙基酯的镍盐,酮肟,如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物,1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,采用或不采用另外的配体。
2.6.位阻胺,例如双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,双(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,双(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-羟基哌啶和琥珀酸的缩合物,N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二-氯-1,3,5-三嗪的线性或环状缩合物,三(2,2,6,6-四甲基-4-哌啶基)次氨基三乙酸酯,四(2,2,6,6-四-甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1′-(1,2-乙烷二基)-双(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-硬脂酰氧基-2,2,6,6-四甲基-哌啶,双(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]癸烷-2,4-二酮,双(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,双(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯,N,N′-双(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-1,3,5-三嗪的线性或环状缩合物,2-氯-4,6-双(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(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-双(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-2,5-二酮,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′-双(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-1,3,5-三嗪的缩合物,1,2-双(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS Reg.No.[136504-96-6])的缩合物;1,6-己烷二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁基胺和4-丁基氨基-2,2,6,6-四甲基哌啶(CAS Reg.No.[192268-64-7])的缩合物;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]癸烷和环氧氯丙烷的反应产物,1,1-双(1,2,2,6,6-五甲基-4-哌啶氧基羰基)-2-(4-甲氧基苯基)乙烷,N,N′-双-甲酰基-N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺,4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯,聚[甲基丙基-3-氧-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷,马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
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′-双(3-二甲基氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙基N,N’-草酰二苯胺和它与2-乙氧基-2′-乙基-5,4′-二-叔丁基N,N’-草酰二苯胺的混合物,邻-和对-甲氧基-二取代N,N’-草酰二苯胺的混合物及邻-和对-乙氧基-二取代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-双(2,4-二甲基苯基)-1,3,5-三嗪,2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪,2,4-双(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-双(4-甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-十二烷氧基苯基)-4,6-双(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-双(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-双(2,4-二甲基)-1,3,5-三嗪,2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-双(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-双(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-双(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]-1,3,5-三嗪,2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪,2-{2-羟基-4-[3-(2-乙基己-1-氧基)-2-羟基丙氧基]苯基}-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属减活剂,例如N,N′-二苯基草酰胺,N-水杨醛-N′-水杨酰基肼,N,N′-双(水杨酰基)肼,N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)肼,3-水杨酰基氨基-1,2,4-三唑,双(亚苄基)草酰基二酰肼,N,N’-草酰二苯胺,间苯二甲酰基二酰肼,癸酰基双苯基酰肼,N,N′-二乙酰基己二酰基二酰肼,N,N′-双(水杨酰基)草酰基二酰肼,N,N′-双(水杨酰基)硫代丙酰基二酰肼。
4.亚磷酸酯和亚膦酸酯,例如三苯基亚磷酸酯,二苯基烷基亚磷酸酯,苯基二烷基亚磷酸酯,三(壬基苯基)亚磷酸酯,三月桂基亚磷酸酯,三-十八烷基亚磷酸酯,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,双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯,双(2,4-二枯基苯基)季戊四醇二亚磷酸酯,双(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,双(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯,双(2,4,6-三(叔丁基苯基)季戊四醇二亚磷酸酯,三硬脂基山梨醇三亚磷酸酯,四(2,4-二-叔丁基苯基)4,4′-双亚苯基二亚膦酸酯,6异辛氧基-2,4,8,10-四-叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂phosphocin,双(2,4-二-叔丁基-6-甲基苯基)甲基亚磷酸酯,双(2,4-二-叔丁基-6-甲基苯基)乙基亚磷酸酯,6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂phosphocin,2,2′,2″-次氨基-[三乙基三(3,3′,5,5′-四-叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯],2-乙基己基(3,3′,5,5′-四-叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯,5-丁基-5-乙基-2-(2,4,6-三-叔丁基苯氧基)-1,3,2-二氧杂phosphirane。
特别优选是如下亚磷酸酯:三(2,4-二-叔丁基苯基)亚磷酸酯(Irgafos168,Ciba-Geigy),三(壬基苯基)亚磷酸酯,
5.羟基胺,例如N,N-二苄基羟基胺,N,N-二乙基羟基胺,N,N-二辛基羟基胺,N,N-二月桂基羟基胺,N,N-二-十四烷基羟基胺,N,N-二-十六烷基羟基胺,N,N-二-十八烷基羟基胺,N-十六烷基-N-十八烷基羟基胺,N-十七烷基-N-十八烷基羟基胺,衍生自氢化牛脂胺的N,N-二烷基羟基胺。
6.硝酮,例如N-苄基-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-四癸基-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-十七烷基硝酮,衍生自N,N-二烷基羟基胺的硝酮,该N,N-二烷基羟基胺衍生自氢化牛脂胺。
7.硫代增效剂,例如硫代二丙酸二月桂酯或硫代二丙酸二硬脂酯。
8.过氧化物清除剂,例如β-硫代丙酸的酯,例如月桂基,硬脂基1,肉豆蔻基或十三烷基酯,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,二-十八烷基二硫化物,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/或磷化合物结合的铜盐和二价镁盐。
10.碱性助稳定剂,例如蜜胺,聚乙烯吡咯烷酮,双氰胺,氰脲酸三烯丙酯,脲衍生物,肼衍生物,胺,聚酰胺,聚氨酯,高级脂肪酸的碱金属和碱土金属盐,例如硬脂酸钙,硬脂酸锌,二十二烷酸镁,硬脂酸镁,蓖麻油酸钠和棕榈酸钾,焦儿茶酚锑或焦儿茶酚锌。
11.成核剂,例如无机物质,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盐,碳酸盐或硫酸盐;有机化合物,如单或多羧酸及其盐,如4-叔丁基苯甲酸,乙二酸,二苯基乙酸,琥珀酸钠或苯甲酸钠;聚合物化合物,如离子共聚物(离聚物)。特别优选是1,3:2,4-双(3′,4′-二甲基亚苄基)山梨醇,1,3:2,4-二(对甲基二亚苄基)山梨醇,和1,3:2,4-二(亚苄基)山梨醇。
12.填料和增强剂,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,例如增塑剂,润滑剂,乳化剂,颜料,流变添加剂,催化剂,流动控制剂,荧光增白剂,阻燃剂,抗静电剂和发泡剂。
14.苯并呋喃酮和吲哚满酮,例如在U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839或EP-A-0591102中公开的那些或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′-双[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,3-(3,4-二甲基苯基-5,7-二-叔丁基苯并呋喃-2-酮,3-(2,3-二甲基苯基)5,7-二-叔丁基苯并呋喃-2-酮。
本发明的进一步方面是一种改进上述涂料组合物的流平的方法,该方法包括如下步骤:
施加涂料组合物到衬底和将它曝露于热能或电磁辐射以获得均匀固体涂料。
本发明的仍然另一方面是由硝酰基介导的受控自由基聚合获得的通式(I),In-[(M)x-(E)y]n(I)的聚合物或共聚物作为涂料组合物的流平剂的用途,其中
In是开始聚合反应的引发剂片段;
M是选自如下的至少一种单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C22)烷基酯、丙烯酸(C1-C22)羟烷基酯、甲基丙烯酸(C1-C22)烷基酯、甲基丙烯酸(C1-C22)羟烷基酯、丙烯酸(C1-C22)烷基酯或甲基丙烯酸(C1-C22)烷基酯,它由氨基、(C1-C22)烷基氨基、(C1-C22)二烷基氨基、-SO3H、环氧、氟、全氟或硅氧烷基团取代、苯乙烯、取代苯乙烯、丙烯酰胺和甲基丙烯酰胺、N-单(C1-C22)烷基丙烯酰胺、N,N-二(C1-C22)烷基丙烯酰胺、和具有两个或多个烯属不饱和键的多官能单体;
条件是未取代丙烯酸(C1-C22)烷基酯或/和甲基丙烯酸(C1-C22)烷基酯的数量大于30wt%,基于总单体混合物的重量;
E是带有至少一个稳定硝酰基自由基的基团,它通过氧原子结合到聚合物或共聚物;或来自连接的稳定硝酰基自由基的取代或消除反应的基团;
x是单体单元的总数目,它是5-5000的数目;
y是1或大于1的数目,指示连接到单体序列(M)x的端基E的平均数目;
n是1-20的数目;
该涂料组合物包括
a1)一种或多种物理干燥成膜粘结剂树脂;
a2)一种或多种热交联成膜粘结剂树脂;
a3)一种或多种可辐射固化的成膜粘结剂树脂;
a4)一种或多种自氧化干燥成膜粘结剂树脂;或
a5)选自a1)、a2)、a3)或a4)的具有至少两种不同交联机理的粘结剂树脂的组合。
曝露以上涂料组合物于热能以获得均匀固体涂料意味着优选加热它到60℃-180℃,更优选80℃-150℃的温度。在热固性粉末涂料的情况下优选的温度范围是150℃-200℃。
曝露涂料于电磁辐射意味着优选对UV辐射的曝露以进行涂料的固化。
也可以结合两种曝露,例如首先采用UV辐射固化组合物和其次施加热处理以进行后固化。
在可辐射固化涂料的情况下固化时间可以为仅几秒,在热固性涂料的情况下为1分钟-60分钟或在自氧化干燥涂料的情况下为几小时。
本发明的进一步方面是一种涂料组合物,该组合物包括:
a1)一种或多种物理干燥成膜粘结剂树脂;
a2)一种或多种热交联成膜粘结剂树脂;
a3)一种或多种可辐射固化的成膜粘结剂树脂;
a4)一种或多种自氧化干燥成膜粘结剂树脂;或
a5)选自a1)、a2)、a3)或a4)的具有至少两种不同交联机理的粘结剂树脂的组合;
b)由原子转移自由基聚合获得的通式(X)的聚合物或共聚物流平剂,In-[(M)x-(E)y]n(X)
其中
In是开始聚合反应的引发剂片段;
M是选自如下的至少一种单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C22)烷基酯、丙烯酸(C1-C22)羟烷基酯、甲基丙烯酸(C1-C22)烷基酯、甲基丙烯酸(C1-C22)羟烷基酯、丙烯酸(C1-C22)烷基酯或甲基丙烯酸(C1-C22)烷基酯,它由氨基、(C1-C22)烷基氨基、(C1-C22)二烷基氨基、-SO3H、环氧、氟、全氟或硅氧烷基团取代、苯乙烯、取代苯乙烯、丙烯酰胺和甲基丙烯酰胺、N-单(C1-C22)烷基丙烯酰胺、N,N-二(C1-C22)烷基丙烯酰胺、和具有两个或多个烯属不饱和键的多官能单体;
条件是未取代丙烯酸(C1-C22)烷基酯或/和甲基丙烯酸(C1-C22)烷基酯的数量大于30wt%,基于总单体混合物的重量;
E是Cl、Br或由Cl或Br的亲核取代诱导的基团;
x是单体单元的总数目,它是5-5000的数目;
y是1或大于1的数目,指示连接到单体序列(M)x的端基E的平均数目;
n是1-20的数目;和
c)任选地水或/和一种或多种有机溶剂。
原子转移自由基聚合(ATRP)描述于,例如WO96/30421。WO96/30421公开了通过采用ATRP方法,烯属不饱和单体如苯乙烯或(甲基)丙烯酸酯的受控或″活″聚合工艺。根据此方法在不同氧化态的过渡金属,如Cu(i)和Cu(II)的氧化还原体系存在下采用产生自由基原子如·Cl的引发剂,提供″活″或受控自由基聚合。
合适的引发化合物具有通式(XI),具有可自由基转移的原子或基团·Hal的
如在WO96/30421和WO98/01480中所述。优选的可自由基转移原子或基团·Hal是·Cl或·Br,它从引发剂分子作为自由基断裂。
[In]表示能够引发单体或低聚物的聚合的通式(XI)的聚合引发剂的聚合引发剂片段,
该聚合引发剂选自C1-C8-烷基卤、C6-C15-芳烷卤、C2-C8α-卤代烷基酯、芳烃磺酰氯、卤代烷烃腈、α-卤代丙烯酸酯、和卤代内酯,和
p和q表示1。
具体的引发剂选自α,α′-二氯-或α,α′-二溴二甲苯、对甲苯磺酰氯(PTS)、六-(α-氯-或α-溴甲基)-苯、2-氯-或2-溴丙酸、2-氯-或2-溴异丁酸、1-苯乙基氯或溴、2-氯-或2-溴丙酸甲酯或乙酯、乙基-2-溴-或乙基-2-氯异丁酸酯、氯-或溴乙腈2-氯-或2-溴丙腈、α-溴-苯并乙腈和α-溴-γ-丁内酯(=2-溴-二氢-2(3H)-呋喃酮)。
用于本发明的方法中可氧化过渡金属配合物催化剂盐中的过渡金属在氧化还原体系的低氧化态下存在为可氧化配合物离子。这样氧化还原体系的优选例子选自V(B),VI(B),VII(B),VIII,IB和IIB元素,如Cu+/Cu2+,Cu0/Cu+,Fe0/Fe2+,Fe2+/Fe3+,Ru2+/Ru3+,Ru3+/Ru4+,Os2+/Os3+,Vn+/N(n+1)+,Cr2+/Cr3+,Co+/Co2+,Co2+/Co3+,Ni0/Ni+,Ni+/Ni2+,Ni2+/Ni3+,Mn0/Mn2+,Mn2+/Mn3+,Mn3+/Mn4+或Zn+/Zn2+。
离子电荷由过渡金属配合物化学中通常已知的阴离子配体等衡,这样的氢阴离子(H-)或衍生自无机或有机酸的阴离子,例子是卤根,如F-、Cl-、Br-或I-,类型BF4 -,PF6 -,SbF6 -或AsF6 -的氟配合物,含氧酸,醇盐或乙酰基化物的阴离子或环戊二烯的阴离子。
含氧酸的阴离子是,例如硫酸根、磷酸根、高氯酸根、高溴酸根、高碘酸根、锑酸根、砷酸根、硝酸根、碳酸根,C1-C8羧酸的阴离子,如甲酸根、乙酸根、丙酸根、丁酸根、苯甲酸根、苯基乙酸根、单-,二-或三氯-或-氟乙酸根、磺酸根,例如甲基磺酸根、乙基磺酸根、丙基磺酸根、丁基磺酸根、三氟甲基磺酸根(三氟甲磺酸根)、未取代或C1-C4烷基-、C1-C4烷氧基-或卤代-,特别地氟-,氯-或溴-取代苯基磺酸根或苄基磺酸根,例如甲苯磺酸根、甲磺酸根、对溴苯磺酸根、对甲氧基-或对乙氧基苯基磺酸根、五氟苯基磺酸根或2,4,6-三异丙基磺酸根、膦酸根,例如甲基膦酸根、乙基膦酸根、丙基膦酸根、丁基膦酸根、苯基膦酸根、对甲基苯基膦酸根或苄基膦酸根、衍生自C1-C8羧酸的羧酸根,例如甲酸根、乙酸根、丙酸根、丁酸根、苯甲酸根、苯基乙酸根、单-,二-或三氯-或-氟乙酸根,和同样C1-C12醇盐,如直链或支化C1-C12醇盐,如甲醇盐或乙醇盐。
阴离子配体和中性配体也可以存在直到配合物阳离子的优选配位数,特别地四个,五个或六个。另外的负电荷由阳离子,特别地单价阳离子如Na+,K+,NH4 +或(C1-C4烷基)4N+等衡。
合适的中性配体是过渡金属的配合物化学中通常已知的无机或有机中性配体。它们通过σ-,π-,μ-,η-类型键合或其任何组合配位到金属离子直到配合物阳离子的优选配位数。合适的无机配体选自水(H2O)、氨基、氮、一氧化碳和硝酰基。合适的有机配体选自膦,如(C6H5)3P、(i-C3H7)3P、(C5H9)3P或(C6H11)3P、二-、三-、四-和羟基胺,如乙二胺、乙二胺四乙酸酯(EDTA)、N,N-二甲基-N’,N’-双(2-二甲基氨基乙基)-乙二胺(Me6TREN)、儿茶酚、N,N’-二甲基-1,2-苯二胺、2-(甲基氨基)苯酚、3-(甲基氨基)-2-丁醇或N,N’-双(1,1-二甲基乙基)-1,2-乙烷二胺、N,N,N’,N’,N’-五甲基二乙基三胺(PMD-ETA)、C1-C8二醇或甘油酯,如乙二醇或丙二醇或其衍生物,如二-,三-或四甘醇二甲醚、和单齿或双齿杂环e-给体配体。
杂环e-给体配体,例如衍生自如下的未取代或取代杂芳烃:呋喃、噻吩、吡咯、吡啶、双吡啶、吡啶甲基亚胺、g-吡喃、g-噻喃、菲咯啉、嘧啶、双嘧啶、吡嗪、吲哚、苯并呋喃、硫茚、咔唑、二苯并呋喃、二苯并噻吩、吡唑、咪唑、苯并咪唑、唑、噻唑、双噻唑、异唑、异噻唑、喹啉、异喹啉、双异喹啉、吖啶、色烯、吩嗪、吩嗪、吩噻嗪、三嗪、噻蒽、嘌呤、双咪唑和双唑。
可氧化的过渡金属配合物催化剂可以在单独的初步反应步骤中从它的配体形成或优选从它的过渡金属盐,如Cu(I)Cl原位形成,然后通常加入对应于配合物催化剂中存在的配合的化合物,如通过加入乙二胺、EDTA、Me6TREN或PMDETA将它转移成配合物化合物。
优选过渡金属配合物盐中的可氧化过渡金属在氧化还原体系的低氧化态中存在为过渡金属配合物离子。
更优选过渡金属配合物离子是Cu(I)/Cu(II)体系中的Cu(I)配合物离子。
通式(XI)的引发剂,
和可氧化过渡金属例如存在的数量为1∶10-1∶100,相对于单体。可氧化过渡金属对通式(III)的引发剂的总数量是例如0.05∶1-2∶1,特别地0.2∶1-0.5∶1。所有的比例是重量比。
由ATRP方法的梳形共聚物的制备例如描述于WO01/51534。
当使用ATRP技术时结合到聚合物末端的氯或溴原子可以除去和/或由官能团,如-ON(R)(R)基团、NH2、-N(R)(R)、OH或-O-C(O)-CR=CH2取代。这样取代的例子在WO01/51534,WO00/18807,WO93/43719或WO 98/40415中给出。
本发明的仍然另一方面是聚丙烯酸叔丁酯或聚甲基丙烯酸叔丁酯和为粉末涂料组合物中流平剂的用途。
对于以上涂料组合物给出的定义和优选也适用于本发明的其它方面。
如下实施例说明本发明。
实施例A:流平剂的聚合
使用的缩写:
PD=多分散性
GPC=凝胶渗透色谱
PS-标准物=聚苯乙烯标准物
PMA=乙酸丙氧基甲酯
THF=四氢呋喃
DEGDA=二丙烯酸二甘醇酯
Zonyl-TM=甲基丙烯酸2-(全氟烷基)乙酯
DMAEMA=甲基丙烯酸二甲基氨基乙酯
PMDETA=N,N,N′,N″-五亚甲基三亚乙基三胺
实施例1A:合成线性高分子量聚(n-BA)。采用化合物O1的聚合
化合物O1
根据GB2335190的实施例24制备
在具有磁力搅拌棒,温度计,冷却器和隔膜的3-颈250mL圆底烧瓶中将80.0g丙烯酸正丁酯(n-BA,128.17g/mol),0.4g化合物O1(317.48g/mol)和2.5g PMA混合在一起,采用N2/真空脱气3次和在N2下在145℃下聚合6h。将残余单体和溶剂在120℃和7mbar下蒸馏出。收率:39%;GPC(THF,PS-标准物,Mn=19500g/mol;PD=1.38),粘性液体。
实施例2A:合成线性高分子量聚(t-BMA-共-n-BA)。
在具有磁力搅拌棒,温度计,冷却器和隔膜的3-颈50mL圆底烧瓶中,将19.0g甲基丙烯酸叔丁酯(t-BMA,142.2g/mol),4.3g丙烯酸正丁酯(n-BA,128.17g/mol),0.5g化合物O1(317.48g/mol)和23.3g PMA混合在一起,采用N2/真空脱气3次和在N2下在120℃下聚合7h。将残余单体和溶剂在120℃和7mbar下蒸馏出。收率49%,GPC(THF,PS-标准物:Mn=8000g/mol,PD=1.62),固体。随后将样品从二烷中的30w%冷冻干燥以获得自由流动粉末。
实施例3A:合成线性高分子量聚(t-BA)。
在具有磁力搅拌棒,滴液漏斗,冷却器和隔膜的3-颈50mL圆底烧瓶中,将25.6g丙烯酸叔丁酯(t-BA,128.17g/mol),1.9g化合物O1(317.48g/mol)和20g PMA混合在一起,采用N2/真空脱气3次和在N2下在145℃下聚合1h。将51.9g丙烯酸叔丁酯加入混合物并在120-145℃下持续聚合6h。将残余单体在120-145℃和7mbar下蒸馏出。收率:75%,GPC(THF,PS-标准物,Mn=8600g/mol,PD=1.28),固体。
实施例4A:合成星型支化高分子量聚(n-BA)。
在具有磁力搅拌棒,温度计,冷却器和隔膜的3-颈100mL圆底烧瓶中,将2.7g二丙烯酸二甘醇酯(DEGDA,214.22g/mol),0.2g化合物O1(317.48g/mol)和55g PMA加入,采用N2/真空脱气3次和在N2下在145℃下聚合6h。将溶剂和残余二丙烯酸酯在减压下蒸馏出。收率69%。将38.6g 丙烯酸正丁酯(n-BA,128.17g/mol)和40g PMA加入,采用N2/真空脱气3次和在N2下在145℃下聚合6h。将残余单体在120℃和7mbar下蒸馏出。收率17%,GPC(THF,PS标准物,Mn=14200,PD=2.83),粘性液体。
通过冷冻干燥在使用二烷的粘合剂体系中母料30w%制备测试样品。
实施例5A:合成线性高分子量聚(t-BA-共-Zonyl-TM)。
在具有磁力搅拌棒,滴液漏斗,冷却器和隔膜的3-颈250mL圆底烧瓶中,将12.8g丙烯酸叔丁酯(t-BA,128.17g/mol),2.8gZonyl-TM(534g/mol),0.95g化合物O1(317.48g/mol)和12g PMA加入,采用真空脱气三次和在N2下在145℃下聚合1h。通过滴液漏斗将25.65g丙烯酸叔丁酯和5.63g Zonyl-TM的混合物缓慢加入反应混合物。反应在N2下在145℃下持续12h。将残余单体和溶剂在120-145℃和7mbar下蒸馏出。收率58%,GPC(THF,PS-标准物,Mn=7400g/mol,PD=1.34),固体。
实施例6A:合成线性高分子量聚(t-BA-共-n-BA-共-t-BMA)。
在具有磁力搅拌棒,滴液漏斗,冷却器和隔膜的3-颈250mL圆底烧瓶中,将3.0g丙烯酸正丁酯(n-BA,128.17g/mol),15.0g丙烯酸叔丁酯(t-BA,128.17g/mol),13.3g甲基丙烯酸叔丁酯(t-BMA,142.2g/mol),2.2g化合物O1(317.48g/mol)和24g PMA加入,采用N2/真空脱气3次和在N2下在145℃下聚合1h。将30.06g丙烯酸叔丁酯,6.01g丙烯酸正丁酯和26.7g甲基丙烯酸叔丁酯的混合物采用滴液漏斗缓慢加入反应混合物。反应在N2下在145℃下持续6h。将残余单体和溶剂在120-145℃和7mbar下蒸馏出。收率58%,GPC(THF,PS-标准物,Mn=7000g/mol,PD=1.59),固体。
实施例7A:合成线性高分子量聚(t-BA-共-t-BMA)。
在具有磁力搅拌棒,冷却器和隔膜的3-颈250mL圆底烧瓶中,将32.04g丙烯酸叔丁酯(t-BA,128.17g/mol),35.55g甲基丙烯酸叔丁酯(t-BMA,128.17g/mol),1.59g化合物O1(317.48g/mol)和20g PMA加入,采用N2/真空脱气3次和在N2下在135℃下聚合7h。将残余单体和溶剂在120-145℃和7mbar下蒸馏出。收率68%,GPC(THF,PS-标准物,Mn=8800g/mol,PD=1.40),固体。
实施例8A:合成线性高分子量聚(t-BA-共-t-BMA)。
在具有磁力搅拌棒,冷却器,计量泵和隔膜的3-颈500mL圆底烧瓶中,将63.3g丙烯酸叔丁酯(t-BA,128.17g/mol),3.7g甲基丙烯酸叔丁酯(t-BMA,142.2g/mol),4.95g化合物O1(317.48g/mol)和51.5g PMA加入,采用N2/真空脱气3次和在N2下在轻微回流(120-130℃)下聚合直到达到约40%的转化率。将7.4g甲基丙烯酸叔丁酯和126.7g丙烯酸叔丁酯的混合物由计量泵(1g/min)加入反应容器。反应在轻微回流和N2下持续另外33h。将残余单体和溶剂在120-145℃和7mbar下蒸馏出。收率53%,GPC(THF,PS-标准物,Mn=6300g/mol,PD=1.41),固体。
实施例9A:合成线性高分子量聚(t-BA-共-DMAEMA)。
在具有磁力搅拌棒,冷却器和隔膜的3-颈500mL圆底烧瓶中将38.45g丙烯酸叔丁酯(t-BA,128.17g/mol),2.51g甲基丙烯酸二甲基氨基乙酯(DMAEMA,157.21g/mol),0.95g化合物O1(317.48g/mol)和10.0g PMA加入,采用N2/真空脱气3次和在N2下在135℃下聚合7h。将残余单体和溶剂在120-145℃和7mbar下蒸馏出。收率60%,GPC(THF,PS-标准物,Mn=8500g/mol,PD=1.34),固体。
实施例10A:合成含有溴端基的线性高分子量聚(t-BA)。
进料:
128.2g(1mol)丙烯酸叔丁酯(t-BA,Fluka,purum)
2.39g(14.3mmol)甲基-2-溴丙酸酯(MBP,Fluka,purum)
0.82g(5.7mmol)Cu(I)Br(Fluka,purum,采用乙酸洗涤和干燥)
0.064g(0.29mmol)Cu(II)BR2(Fluka,purum)
0.99g(5.71mmol)PMDETA(Fluka,purum)
36.3ml丙酮(Fluka,puriss p.a.)
将Cu(I)Br和Cu(II)BR2加入具有机械搅拌和N2和真空的入口/出口的350ml 3-颈反应容器。将容器抽空和采用N2清洗3次,随后加入在丙酮中的单体t-BA。将反应混合物再次抽空和采用N2清洗4次和由机械搅拌均化。将配体前体PMDETA现在采用注射器通过隔膜加入,均化和加入引发剂MBP。在均化之后,将混合物在搅拌下加热到60℃。转化率由1H-NMR监测:在1.5h之后18%,在19h之后81%,在26h之后88%。将反应混合物冷却到室温,采用150ml乙酸乙酯稀释和通过2部分70g Al2O3搅拌30min。将混合物过滤和在真空(p<0.1mbar)中在90℃下在1h期间干燥。收率:103g。
分析数据:
GPC(THF,PS-标准物s):Mn:7750,Mw:9320,PDI=1.20(Mn(calc.):8050。
DSC(10℃/min):Tg=39℃。
TGA(10℃/min):重量损失:在T=170-220℃下44%
固体测试仪:当在200℃下放置10min时13%重量损失
实施例11A:合成含有吗啉端基的线性高分子量聚(t-BA)。
进料:
50.0g(6.2mmol端基)聚(丙烯酸叔丁酯)(来自Ex.10A)
5.4g(62mmol)吗啉(Fluka,puriss.p.a.)
50ml甲苯
将聚合物加入具有机械搅拌和N2和真空的入口/出口的350ml 3-颈反应容器。将容器抽空和采用N2清洗3次,随后加入吗啉。将反应混合物在预热到130℃的油浴上加热。一旦反应混合物的温度达到100℃开启机械搅拌。将混合物在130℃下加热4 h,冷却到90℃和加入50ml甲苯。在冷却到R.T.之后将反应混合物过滤和在真空(p<0.1mbar)中在90℃下在1h期间干燥。收率:47.7g。
分析数据:
GPC(THF,PS-标准物):Mn:5950,Mw:8075,PD=1.36。
N-含量(Kjeldahl分析):0.18%(calc.:0.17%)。
TGA(10℃/min):重量损失:在T=220-250℃下的47%
固体测试仪:当在200℃下放置10min时0.6%重量损失
实施例12A:合成线性高分子量聚(t-BA)。
在具有磁力搅拌棒,滴液漏斗,冷却器和隔膜的3-颈50mL圆底烧瓶中,将25.6g丙烯酸叔丁酯(t-BA,128.17g/mol),1.9g化合物O1(317.48g/mol)和20g PMA一起混合,采用N2/真空脱气3次和在N2下在轻微回流下聚合1h。将51.9g计量入混合物和聚合在120-130℃下持续另外6h。将残余单体在120-145℃和7mbar下蒸馏出。收率:45%,GPC(THF,PS-标准物,Mn=6400g/mol,PD=1.32),固体。
实施例13A:合成线性高分子量聚(t-BA-共-DMAEMA)。
在具有磁力搅拌棒,冷却器和隔膜的3-颈250mL圆底烧瓶中,将38.45g丙烯酸叔丁酯(t-BA,128.17g/mol),0.95g化合物O1(317.48g/mol)和10.0g PMA加入,采用N2/真空脱气3次和在N2下在135℃下聚合6h。将2.51g甲基丙烯酸二甲基氨基乙酯(DMAEMA,157.21g/mol)加入烧瓶和在145℃下反应另外一小时。将残余单体和溶剂在120-145℃和7mbar下蒸馏出。收率57%,GPC(THF,PS-标准物,Mn=7900g/mol,PD=1.29),固体。
实施例14A:合成聚(t-BA-b-StearylA)。
在具有磁力搅拌棒,滴液漏斗,冷却器和隔膜的3-颈500mL圆底烧瓶中,将24.0g丙烯酸叔丁酯(t-BA,128.17g/mol),7.2g丙烯酸十八烷基酯(ODA,324..55g/mol),2.7g化合物O1(317.48g/mol)和25g乙酯乙基己酯一起混合,采用N2/真空脱气3次和在N2下在轻微回流下聚合1h。将56g t-BA和18.11g ODA计量入混合物和聚合在135℃下持续另外6h。将残余单体在120-145℃和7mbar下蒸馏出。收率:65%,GPC(THF,PS-标准物,Mn=8600g/mol,PD=1.35),固体。
实施例15A:合成聚(t-BA-b-BehenvIA)。
在具有磁力搅拌棒,滴液漏斗,冷却器和隔膜的3-颈500mL圆底烧瓶中,将34.61g丙烯酸叔丁酯(t-BA,128.17g/mol),11.42g丙烯酸二十二烷基酯(BhA,324..55g/mol),3.85g化合物O1(317.48g/mol)和40g乙酸乙基己酯一起混合,采用N2/真空脱气3次和在N2下在轻微回流下聚合1h。将80.74g t-BA和26.64g BhA计量入混合物,并在135℃下持续聚合另外6h。将残余单体在120-145℃和7mbar下蒸馏出。加入0.3g过辛酸叔丁酯和在90℃下加热4h。收率:49%,GPC(THF,PS-标准物,Mn=6400g/mol,PD=1.23),固体。
B应用实施例:粉末涂料实施例
实施例1B:基于羧基官能聚酯和作为硬化剂的羟基烷基酰胺的非着色粉末涂料
粉末涂料组合物基于羧基官能聚酯,组分1-4(没有流平剂的配制剂)或组分1-5(包含流平剂的配制剂),如表1所示。
表1:配制剂
组分 | 实施例(以克计的数量) | ||
1.1对比 | 1.2-1.4 | 1.5对比 | |
1.Crylcoat2532a) | 960 | 960 | 960 |
2.PrimidXL552b) | 35 | 35 | 35 |
3.Ceridust9615c) | 3 | 3 | 3 |
4.苯偶姻 | 2 | 2 | 2 |
5.流平剂 | - | 10 | 10e) |
总计: | 1000 | 1010 | 1010 |
a)Crylcoate2532,羧基官能聚酯,购自比利时Drogenbos的UCBS.A.公司
b)PrimidXL 552,N,N,N′,N′-四(2-羟基乙基)己二酰二胺,购自瑞士Domat的EMS公司
c)Ceridust9615,蜡,购自瑞士Muttenz的Cariant AG公司
d)苯偶姻,购自Fluka AG
e)Modaflow P3,购自UCB Surface Specialties,USA商业流平剂。
使用行星混合机混合组分。然后将混合物在棱柱挤出机上在300转/分钟和110℃下挤出和展开。将粉末涂料组合物使用台架切割机粗糙粉碎,并在具有0.75mm环状穿孔筛的Retsch ZM-1超离心碾磨机中在15,000转/分钟下研磨。最后,将粉末通过平均粒度为30-50μm的离心筛分机上的125μm筛。
使用ESB-Wagner电晕杯枪在60kV下将完成的粉末涂料组合物静电喷涂70-80μm涂层厚度到铝盘上。将涂覆的盘在电烘箱中在180℃下固化10分钟。
测定如下参数:
1)黄度:b*ISO 7724(ASTM D2244)。大的b*数值指示强烈变黄。
2)根据制造商建议的操作方法采用BYK Gardner光雾度-光泽测量光泽@20°。高光泽值指示涂料膜的高反射比。
3)根据制造商建议的操作方法采用BYK Gardner波扫描DOI来测定DOI(反射图像清晰度)。DOI数值为零表示完美的扩散,而DOI数值为100表示完美的镜面图像,指示非常平滑的表面。
4)根据制造商建议的操作方法采用BYK Gardner波扫描DOI来测定长波。更小数量的长波值指示具有更平滑外观的涂层。
表2:在180℃下固化10分钟之后的结果
实施例 | 流动剂 | b* | 光泽@20° | 长波 | DOI |
1.1B | - | 7 | - | - | - |
1.2B | 实施例10A | 9 | 84 | 33 | 87 |
1.3B | 实施例1A | 5 | 90 | 31 | 85 |
1.4B | 实施例4A | 9 | 91 | 56 | 81 |
1.5B | ModaflowP3 | 17 | 83 | 28 | 87 |
实施例2B:基于羧基官能聚酯和作为硬化剂的羟基烷基酰胺的着白色粉末涂料
如在实施例1B中所述制备所有的粉末涂料和测定它们的参数。配制剂在表3中给出。
表3:配制剂
组分 | 实施例(以克计的数量) | ||
2.1对比 | 2.2-2.3 | 2.4对比 | |
1.Crylcoat2532a) | 670 | 670 | 670 |
2.PrimidXL552b) | 25 | 25 | 25 |
3.Ceridust9615c) | 3 | 3 | 3 |
4.苯偶姻 | 2 | 2 | 2 |
5.Kronos2160e) | 300 | 300 | 300 |
6.流平剂 | - | 10 | 10f) |
总计: | 1000 | 1010 | 1010 |
a)Crylcoate2532,羧基官能聚酯,购自比利时DrogenbosUCB S.A.公司
b)PrimidXL 552,N,N,N′,N′-四(2-羟基乙基)己二酰胺,购自瑞士DomatEMS公司
c)Ceridust9615,蜡,购自瑞士Muttenz的Cariant AG公司
d)苯偶姻,购自Fluka AG
e)Kronos 2160(TiO2),购自德国Kronos的
f)Modaflow P3,购自UCB Surface Specialties,USA商业流平剂。
表4:在180℃下固化10分钟之后的结果
实施例 | 流动剂 | b* | 光泽@20° | 长波 | |
2.1B | - | 4 | - | - | - |
2.2B | 实施例10A | 3 | 82 | 61 | 82 |
2.3B | 实施例1A | 4 | 80 | 67 | 79 |
2.4B | Modaflow P3 | 4 | 81 | 56 | 83 |
实施例3B:基于GMA-丙烯酸类和作为硬化剂的DDDA的非着色粉末涂料
如在实施例1B中所述制备所有的粉末涂料和测定它们的参数。
表5:配制剂
组分 | 实施例(以克计的数量) | ||
3.1对比 | 3.2 | 3.3对比 | |
1.AlmatexPD7610a) | 790 | 790 | 790 |
2.DDDAb) | 170 | 170 | 170 |
3.Tinuvin144c) | 10 | 10 | 10 |
4.Tinuvin405d) | 20 | 20 | 20 |
5.WorleeADD 902e) | 10 | 10 | 10 |
6.流平剂 | - | 10 | 10f) |
总计: | 1000 | 1010 | 1010 |
a)AlmatexePD7610,GMA-丙烯酸类树脂,购自USA的Anderson
b)DDDA是十二烷二酸,购自德国DuPont的
c)Tinuvin144是位阻胺光稳定剂,购自瑞士Basel的CibaSpecialty Chemicals
d)Tinuvin405是UV-吸收剂,购瑞士Basel的Ciba SpecialtyChemicals
e)WorleeADD 902,购自德国的Worlee Chemie
f)AdditolXL490,商业流动剂,购自美国的UCB SurfaceSpecialties,
表6:在160℃下固化30分钟之后的结果
实施例 | 流动剂 | b* | 光泽@20° | 长波 | DOI |
3.1B | - | 0.3 | - | - | - |
3.2B(DFT=70μM) | 实施例10A | 0.2 | 79 | 4 | 92 |
3.3B(DFT=70μM) | AdditolXL 490 | 0.4 | 79 | 5 | 91 |
3.2B(DFT=40μM) | 实施例10A | -0.1 | 79 | 14 | 91 |
3.3B(DFT=40μM) | AdditolXL 490 | -0.1 | 78 | 18 | 89.5 |
DFT=干燥膜厚度
实施例4B:基于GMA-丙烯酸类和作为硬化剂的DDDA的非着色粉末涂料
如在实施例1B中所述制备所有的粉末涂料和测定它们的参数。
表7:配制剂
组分 | 实施例(以克计的数量) | ||
4.1对比 | 4.2-4.8 | 4.9对比 | |
1.AlmatexPD7610 | 795 | 790 | 790 |
2.DDDA | 170 | 170 | 170 |
3.Tinuvin144 | 10 | 10 | 10 |
4.Tinuvin405 | 20 | 20 | 20 |
5.苯偶姻 | 5 | 10 | 10 |
6.流平剂 | - | 10 | 10e) |
总计: | 1000 | 1010 | 1010 |
e)Powdermate468CFL,商业流平剂,购自荷兰的Troy ChemicalCompany BV
表8:在170℃下固化20分钟之后的结果
实施例 | 流动剂 | b* | 光泽@20° | 长波 | DOI |
4.1B | - | 2.5 | - | - | - |
4.2B | 实施例11A | 2.6 | 80 | 10 | 86.5 |
4.3B | 实施例3A | 2.8 | 81 | 11 | 85 |
4.4B | 实施例12A | 3.6 | 80 | 11 | 84 |
4.5B | 实施例13A | 3 | 82 | 15 | 84 |
4.6B | 实施例8A | 2.8 | 83 | 11 | 84 |
4.7B | 实施例6A | 2.5 | 83 | 16 | 84 |
4.8B | 实施例5A | 2.6 | 84 | 17 | 85 |
4.9B | Powdermate486CFL | 2.9 | 82 | 25 | 85.5 |
实施例5B:基于GMA-丙烯酸类和作为硬化剂的DDDA的非着色粉末涂料
如在实施例1B中所述制备所有的粉末涂料和测定它们的参数。
表9:配制剂
组分 | 实施例(以克计的数量) | |
5.1对比 | 5.2-5.3 | |
1.AlmatexPD7610 | 549 | 545 |
2.DDDA | 119 | 119 |
3.Tinuvin1 44 | 7 | 7 |
4.Tinuvin405 | 25 | 14 |
5.苯偶姻 | 3.5 | 3.5 |
6.流平剂 | 7.5a) | 11.5 |
总计: | 700 | 700 |
a)Additol XL 490
表10:在160℃下固化30分钟之后的结果
实施例 | 流动剂 | b* | 光泽@20° | 长波 | DOI |
5.1B | -Additiol XL 490 | 1.9 | 83.1 | 8.8 | 91.3 |
5.2B | 实施例14A | 2.0 | 84.9 | 8.2 | 91.8 |
5.3B | 实施例15A | 2.1 | 85.3 | 12.6 | 91.5 |
Claims (20)
1.一种涂料组合物,包含:
a1)一种或多种物理干燥成膜粘结剂树脂;
a2)一种或多种热交联成膜粘结剂树脂;
a3)一种或多种可辐射固化的成膜粘结剂树脂;
a4)一种或多种自氧化干燥成膜粘结剂树脂;或
a5)选自a1)、a2)、a3)或a4)的具有至少两种不同交联机理的粘结剂树脂的组合;
b)由硝酰基介导的受控自由基聚合获得的通式(I)In-[(M)x-(E)y]n(I)的聚合物或共聚物流平剂,其中
In是开始聚合反应的引发剂片段;
M是选自如下的至少一种单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C22)烷基酯、丙烯酸(C1-C22)羟烷基酯、甲基丙烯酸(C1-C22)烷基酯、甲基丙烯酸(C1-C22)羟烷基酯、丙烯酸(C1-C22)烷基酯或甲基丙烯酸(C1-C22)烷基酯,其由氨基、(C1-C22)烷基氨基、(C1-C22)二烷基氨基、-SO3H、环氧、氟、全氟或硅氧烷基团取代、苯乙烯、取代的苯乙烯、丙烯酰胺和甲基丙烯酰胺、N-单(C1-C22)烷基丙烯酰胺、N,N-二(C1-C22)烷基丙烯酰胺,和具有两个或多个烯属不饱和键的多官能单体;
条件是未取代丙烯酸(C1-C22)烷基酯或/和甲基丙烯酸(C1-C22)烷基酯的数量大于30wt%,基于总单体混合物的重量;
E是带有至少一个稳定硝酰基自由基的基团,其通过氧原子结合到聚合物或共聚物;或来自连接的稳定硝酰基自由基的取代或消除反应的基团;
x是单体单元的总数目,其是5-5000的数;
y是1或大于1的数,指示连接到单体序列(M)x的端基E的平均数目;
n是1-20的数;和
c)任选地水或/和一种或多种有机溶剂。
2.根据权利要求1的涂料组合物,包含
a2)一种或多种热交联成膜粘结剂树脂;或
a3)一种或多种可辐射固化的成膜粘结剂树脂。
3.根据权利要求1的涂料组合物,包含
a2)一种或多种热交联成膜粘结剂树脂。
4.根据权利要求1的涂料组合物,包含
a2)一种或多种没有水和有机溶剂的热交联成膜粘结剂树脂,其形式为固体粉末。
5.根据权利要求1的涂料组合物,其中通式(I)的聚合物或共聚物流平剂由如下方式获得:
b1)在含有结构组元
的烷氧基胺引发剂/调节剂存在下的聚合;或
b2)在含有结构组元
的稳定硝酰基自由基和自由基引发剂存在下的聚合。
其中G1,G2,G3,G4独立地是C1-C6烷基或G1和G2或G3和G4,或G1和G2和G3和G4一起形成C5-C12环烷基;
G5,G6独立地是H、C1-C18烷基、苯基、萘基或基团COOC1-C18烷基;
X选自-CH2-苯基、CH3CH-苯基、(CH3)2C-苯基、(C5-C6环烷基)2CCN、(CH3)2CCN、
-CH2CH=CH2、CH3CH-CH=CH2(C1-C4烷基)CR20-C(O)-苯基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷氧基、(C1-C4)烷基-CR20-C(O)-(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-N-二(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH(C1-C4)烷基、(C1-C4)烷基-CR20-C(O)-NH2,其中
R20是氢或(C1-C4)烷基和
*表示化合价。
7.根据权利要求6的涂料组合物,其中通式(II)的结构组元是通式(O1)的化合物
8.根据权利要求1的涂料组合物,其中组分b)流平剂的多分散性为1.0-2.0。
9.根据权利要求1的涂料组合物,其中组分b)流平剂的玻璃化转变温度为20℃-200℃。
10.根据权利要求1的涂料组合物,其中组分b)流平剂包含至少30wt%丙烯酸叔丁酯和/或甲基丙烯酸叔丁酯,基于总单体的重量。
11.根据权利要求1的涂料组合物,其中组分b)流平剂是线性聚合物或共聚物,即在通式(I)中n是1。
12.根据权利要求1的涂料组合物,其中在组分b)通式(I)中,y是1。
13.根据权利要求1的涂料组合物,其中组分b)流平剂的分子量为3000-50000g/mol(道尔顿)。
14.根据权利要求1的涂料组合物,其中组分b)流平剂包含至少30wt%丙烯酸叔丁酯和/或甲基丙烯酸叔丁酯,和0.5-50%选自如下的官能单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C6)羟烷基酯、甲基丙烯酸(C1-C6)羟烷基酯、丙烯酸(C1-C6)烷基酯和甲基丙烯酸(C1-C6)烷基酯,其由氨基、(C1-C6)烷基氨基、(C1-C6)二烷基氨基、环氧、氟、全氟或硅氧烷基团取代。
15.根据权利要求1的涂料组合物,其中组分b)流平剂包含至少50wt%丙烯酸叔丁酯和/或甲基丙烯酸叔丁酯,并且在室温下为固体。
16.根据权利要求1的涂料组合物,其中组分b)流平剂存在的量为0.1-15wt%,基于组分a)一种或多种成膜粘结剂树脂,的重量。
17.一种改进根据权利要求1的涂料组合物的流平的方法,该方法包括如下步骤:
施加涂料组合物到衬底和将它曝露于热能或电磁辐射以获得均匀固体涂料。
18.由硝酰基介导的受控自由基聚合获得的通式(I),In-[(M)x-(E)y]n(I)的聚合物或共聚物作为用于流平剂涂料组合物的的用途,其中
In是开始聚合反应的引发剂片段;
M是选自如下的至少一种单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C22)烷基酯、丙烯酸(C1-C22)羟烷基酯、甲基丙烯酸(C1-C22)烷基酯、甲基丙烯酸(C1-C22)羟烷基酯、丙烯酸(C1-C22)烷基酯或甲基丙烯酸(C1-C22)烷基酯,其由氨基、(C1-C22)烷基氨基、(C1-C22)二烷基氨基、-SO3H、环氧、氟、全氟或硅氧烷基团取代、苯乙烯、取代的苯乙烯、丙烯酰胺和甲基丙烯酰胺、N-单(C1-C22)烷基丙烯酰胺、N,N-二(C1-C22)烷基丙烯酰胺和具有两个或多个烯属不饱和键的多官能单体;
条件是未取代的丙烯酸(C1-C22)烷基酯或/和甲基丙烯酸(C1-C22)烷基酯的数量大于30wt%,基于总单体混合物的重量;
E是带有至少一个稳定硝酰基自由基的基团,其通过氧原子结合到聚合物或共聚物;或来自连接的稳定硝酰基自由基的取代或消除反应的基团;
x是单体单元的总数目,其是5-5000的数;
y是1或大于1的数,指示连接到单体序列(M)x的端基E的平均数目;
n是1-20的数;
该涂料组合物包括
a1)一种或多种物理干燥成膜粘结剂树脂;
a2)一种或多种热交联成膜粘结剂树脂;
a3)一种或多种可辐射固化的成膜粘结剂树脂;
a4)一种或多种自氧化干燥成膜粘结剂树脂;或
a5)选自a1)、a2)、a3)或a4)的具有至少两种不同交联机理的粘结剂树脂的组合。
19.一种涂料组合物,包括:
a1)一种或多种物理干燥成膜粘结剂树脂;
a2)一种或多种热交联成膜粘结剂树脂;
a3)一种或多种可辐射固化的成膜粘结剂树脂;
a4)一种或多种自氧化干燥成膜粘结剂树脂;或
a5)选自a1)、a2)、a3)或a4)的具有至少两种不同交联机理的粘结剂树脂的组合;
b)由原子转移自由基聚合获得的通式(X)的聚合物或共聚物流平剂,In-[(M)x-(E)y]n (X)
其中
In是开始聚合反应的引发剂片段;
M是选自如下的至少一种单体:丙烯酸、甲基丙烯酸、丙烯酸(C1-C22)烷基酯、丙烯酸(C1-C22)羟烷基酯、甲基丙烯酸(C1-C22)烷基酯、甲基丙烯酸(C1-C22)羟烷基酯、丙烯酸(C1-C22)烷基酯或甲基丙烯酸(C1-C22)烷基酯,其由氨基、(C1-C22)烷基氨基、(C1-C22)二烷基氨基、-SO3H、环氧、氟、全氟或硅氧烷基团取代、苯乙烯、取代的苯乙烯、丙烯酰胺和甲基丙烯酰胺、N-单(C1-C22)烷基丙烯酰胺、N,N-二(C1-C22)烷基丙烯酰胺和具有两个或多个烯属不饱和键的多官能单体;
条件是丙烯酸叔丁酯的数量大于30wt%,基于总单体混合物的重量;
E是Cl、Br或由Cl或Br的亲核取代诱导的基团;
x是单体单元的总数目,它是5-5000的数;
y是1或大于1的数,指示连接到单体序列(M)x的端基E的平均数目;
n是1-20的数;和
c)任选地水或/和一种或多种有机溶剂。
20.聚丙烯酸叔丁酯或聚甲基丙烯酸叔丁酯作为粉末涂料组合物中流平剂的用途。
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JP4778535B2 (ja) * | 2007-04-06 | 2011-09-21 | 大阪瓦斯株式会社 | フェノール樹脂およびその製造方法 |
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WO2005059048A8 (en) | 2005-09-01 |
RU2395551C2 (ru) | 2010-07-27 |
DE602004008967D1 (de) | 2007-10-25 |
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ATE373056T1 (de) | 2007-09-15 |
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US7829643B2 (en) | 2010-11-09 |
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