CN101522745A - 以封闭异氰酸酯为基础的体系的光潜碱 - Google Patents
以封闭异氰酸酯为基础的体系的光潜碱 Download PDFInfo
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- CN101522745A CN101522745A CNA2007800362458A CN200780036245A CN101522745A CN 101522745 A CN101522745 A CN 101522745A CN A2007800362458 A CNA2007800362458 A CN A2007800362458A CN 200780036245 A CN200780036245 A CN 200780036245A CN 101522745 A CN101522745 A CN 101522745A
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 40
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 119
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 239000000852 hydrogen donor Substances 0.000 claims abstract description 12
- -1 methene compound Chemical class 0.000 claims description 122
- 238000000576 coating method Methods 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 239000011248 coating agent Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
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- 239000003513 alkali Substances 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 26
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000975 dye Substances 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 18
- 239000012965 benzophenone Substances 0.000 claims description 18
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- 125000003700 epoxy group Chemical group 0.000 claims description 11
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 11
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 239000008393 encapsulating agent Substances 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000001409 amidines Chemical class 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004327 boric acid Substances 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 238000004382 potting Methods 0.000 claims description 5
- 150000003217 pyrazoles Chemical class 0.000 claims description 5
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- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 150000003949 imides Chemical class 0.000 claims description 4
- 239000000206 moulding compound Substances 0.000 claims description 4
- 229920006295 polythiol Polymers 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 claims description 3
- OSWDNIFICGLKEE-UHFFFAOYSA-N 2-acetylcyclopentan-1-one Chemical compound CC(=O)C1CCCC1=O OSWDNIFICGLKEE-UHFFFAOYSA-N 0.000 claims description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 150000007945 N-acyl ureas Chemical class 0.000 claims description 3
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- 150000003997 cyclic ketones Chemical class 0.000 claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 3
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000999 acridine dye Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000001022 rhodamine dye Substances 0.000 claims 1
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- 239000000976 ink Substances 0.000 description 54
- 239000002585 base Substances 0.000 description 53
- 239000000463 material Substances 0.000 description 47
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
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- 239000000654 additive Substances 0.000 description 15
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- 125000000217 alkyl group Chemical class 0.000 description 14
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 12
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
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- 125000001624 naphthyl group Chemical group 0.000 description 9
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- 229940059574 pentaerithrityl Drugs 0.000 description 9
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- 150000003254 radicals Chemical class 0.000 description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 description 9
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
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- 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
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- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-N sodium;2-hydroxypropanoic acid Chemical compound [Na+].CC(O)C(O)=O NGSFWBMYFKHRBD-UHFFFAOYSA-N 0.000 description 1
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- 229910052682 stishovite Inorganic materials 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
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- 150000003512 tertiary amines Chemical group 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
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- 229910052905 tridymite Inorganic materials 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical group OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
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Abstract
本发明涉及包括以下组分的组合物:(a)光潜碱;(b)封闭异氰酸酯或封闭异硫氰酸酯和(c)氢给体化合物;和它的应用。
Description
本发明涉及包含光潜(photolatent)碱的封闭异氰酸酯或异硫氰酸酯组合物。
包含封闭异氰酸酯化合物、氢给体化合物和催化剂的组合物在现有技术中是已知的,例如从WO 95/04093中已知。该组合物通常经由热过程来交联,例如通过使用热潜催化剂。
以异氰酸酯/氢供体例如多元醇为基础的涂料和粘合剂体系,配制剂显示出差的稳定性,在室温下几个小时内发生凝胶化。以封闭异氰酸酯和氢供体为基础的未催化的体系在低温下提供稳定的配制剂。在利用热和/或催化剂的作用的该体系中异氰酸酯被解封闭或另外封闭用基团以提供交联的方式进行反应。因此在加热步骤之前、过程中或之后允许氢供体化合物加成到异氰酸酯组分上。因此,稳定的体系导致在高温下(通常在120℃和140℃之间)交联的形成。催化剂有助于降低此类体系的烘烤温度,有时不利地影响配制剂的稳定性。
提供稳定的配制剂同时降低烘烤温度是本领域中公认的。
现已发现,某些光潜催化剂的添加提供稳定的配制剂,同时在催化剂的光活化之后降低封闭异氰酸酯/氢供体混合物的烘烤温度。
本发明的目的因此是组合物,该组合物包括
(a)光潜碱;
(b)封闭异氰酸酯或封闭异硫氰酸酯和
(c)氢给体化合物。
令人吃惊地该组合物具有改进的稳定性,同时在光活化之后显示出类似的反应活性,与非潜在催化剂相比。以封闭异氰酸酯为基础的稳定配制剂在曝光之后显示出快速固化。
在本发明中光潜碱(a用作使封闭异氰酸酯组分(b)与氢给体组分(c)进行交联用的催化剂。
光潜碱的例子包括式II的化合物,
Z-A (II),
其中
Z是对光不稳定基团;和
A是碱前体基团,以共价键键接于Z。
作为碱前体基团的A例如是
作为对光不稳定基团的Z例如是
前提条件是,在式II的化合物中,基团A1与基团Z1相结合;基团A2与基团Z2相结合;和基团A3与基团Z3相结合;
R1是芳族或杂芳族基团,它能够吸收在200-650nm的波长范围内的光,并且它是未被取代的或被一个或多个C1-C20-烷基,C2-C20-链烯基,C2-C18-炔基,C1-C20-卤代烷基,NR10R11,CN,OR10,SR10,COR11,COOR12,卤素或以下取代基所取代:
或R1是
R2和R3彼此独立地是氢,C1-C18-烷基,C1-C18-链烯基,C3-C18-炔基或苯基,该苯基是未被取代的或被一个或多个C1-C18-烷基,CN,OR10,SR10,卤素,或C1-C18-卤代烷基取代;
R5是C1-C18-烷基或NR10R11;
R4,R6和R7彼此独立地是氢或C1-C18-烷基;或
R4和R6一起形成C2-C12-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;或
R5和R7,与R4和R6独立地,一起形成C2-C12亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;或,如果R5是NR10R11,R7和R11一起形成C2-C12-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;
R10,R11和R12彼此独立地是氢或C1-C18烷基;
R13是芳族或杂芳族基团,它能够吸收在200-650nm波长范围内的光并且它是未被取代的或被一个或多个的取代基C1-C18-烷基,C2-C18-链烯基,C2-C18-炔基,C1-C18-卤代烷基,NR10R11,CN,OR10,SR10,COR11,COOR12,或卤素取代;
R14是氢或C1-C18-烷基;
R15是氢,C1-C18-烷基或苯基,该苯基是未被取代的或被一个或多个C1-C18-烷基,乙烯基,C3-C18-链烯基,C3-C18-炔基,C1-C18-卤代烷基,苯基,NR10R11,CN,OR10,SR10,COR11,COOR12,或卤素取代;
Ar1是具有式V、VI、VII或VIII的芳族基团
U是O,S或N(R32);
V具有对于U给出的含义中的一种或是CO,CH2,CH2CH2,C2-C6-烷叉基或直接键;
W是C1-C7-亚烷基或C2-C6-烷叉基;
R16和R17各自彼此独立地是环戊基,环己基,未被取代的C1-C12-烷基;被OH,C1-C4-烷氧基,SH,CN,(CO)O(C1-C8-烷基),O(CO)C1-C4-烷基,苯氧基,卤素和/或苯基取代的C1-C12烷基;
或R16和R17是未被取代的或被卤素、C1-C12-烷基和/或C1-C12-烷氧基取代的苯基;
或R16和R17是
或R16和R17一起是C2-C9-亚烷基或C3-C9-氧杂亚烷基,或一起形成下式的基团:
p是0或1;
q是0,1,2,或3;
y是1或2;
Ar2是苯基,萘基,噻吩基或呋喃基,它们中的每一个是未被取代的或被卤素,OH,C1-C12-烷基,C1-C12-烷氧基,(OCH2CH2)xOH,(OCH2CH2)xOCH3,C1-C8-烷硫基,苯氧基,(CO)O(C1-C18-烷基),CO(OCH2CH2)xOCH3,苯基或苯甲酰基取代;
或基团苯基,萘基,噻吩基或呋喃基被C1-C4-烷基取代,该烷基被OH,卤素,C1-C12-烷氧基,(CO)O(C1-C18-烷基),CO(OCH2CH2)xOCH3和/或OCO(C1-C4-烷基)取代;
或基团苯基,萘基,噻吩基或呋喃基被C1-C4-烷氧基取代,后者被(CO)O(C1-C18-烷基)或CO(OCH2CH2)xOCH3取代;
x是1-20;
R18是C1-C12-烷基,C3-C5-链烯基,C5-C12-环烷基,苯基-C1-C3-烷基或被OH、C1-C4-烷氧基、CN和/或(CO)O(C1-C4-烷基)取代的C2-C4-烷基;
R19是C1-C12-烷基,C3-C5-链烯基,C5-C12-环烷基,苯基-C1-C3-烷基或被OH、C1-C4-烷氧基、CN和/或(CO)O(C1-C4-烷基)取代的C2-C4-烷基;
或R19是未被取代的或被C1-C12-烷基、C1-C4-烷氧基或(CO)O(C1-C4-烷基)取代的苯基;
或R19与R17一起是C1-C7-亚烷基,苯基-C1-C4-亚烷基,邻-亚二甲苯基,2-亚丁烯基或C2-C3-氧杂亚烷基;
或R18和R19与它们所连接到的氮原子一起形成5-,6-或7-员环,该环任选被O,S,CO或NR37***;
或R18和R19一起是C3-C7-亚烷基,后者任选被OH,C1-C4-烷氧基和/或(CO)O(C1-C4-烷基)取代;
R26,R27,R28,R29和R30各自彼此独立地是氢,卤素,C1-C12-烷基,环戊基,环己基,苯基,苄基,苯甲酰基,OR32,SR37,SOR37,SO2R37,N(R38)(R39),NH-SO2R42或
Y是O,S,N(R40),N(R40)-R41-N(R40)或
R31是氢,C1-C12-烷基,卤素或C2-C8-链烷酰基;
R32是氢,C1-C12-烷基,(CO)O(C1-C4-烷基),(CH2CH2O)xH,C2-C8-链烷酰基,C3-C12-链烯基,环己基,羟基环己基,苯基-C1-C3-烷基,Si(C1-C8-烷基)r(苯基)3-r或者被SH,CN,OH,C1-C4-烷氧基,C3-C6-链烯氧基,OCH2CH2CN,OCH2CH2COO(C1-C4-烷基),COOH和/或未取代或被SH取代的O(CO)-C1-C4-烷基所取代的C2-C6-烷基;
或R32是未被取代的或被卤素,C1-C12-烷基和/或C1-C4-烷氧基取代的苯基;
r是1,2或3;
R33是氢,C1-C6-烷基或苯基;
R34,R35和R36各自彼此独立地是氢或C1-C4-烷基,或R34和R35一起是C3-C7-亚烷基;
R37是氢,C1-C12-烷基,C3-C12-链烯基,环己基,苯基-C1-C3-烷基,OCH2CH2COO(C1-C4-烷基)或被SH,OH,CN,COOH,(CO)O(C1-C4-烷基),C1-C4-烷氧基,OCH2CH2CN和/或未被取代的或被SH取代的O(CO)-C1-C4-烷基所取代的C2-C12-烷基;或R37是被S或O***的C1-C12-烷基;或R37是未被取代的或被卤素,SH,C1-C12烷基和/或C1-C4-烷氧基取代的苯基;
R38和R39各自彼此独立地是C1-C12-烷基,C2-C4-羟烷基,C2-C10-烷氧基烷基,C3-C5-链烯基,C5-C12-环烷基,苯基-C1-C3-烷基,C2-C3-链烷酰基,苯甲酰基,O(CO-C1-C8)o-OH或未被取代的或被卤素,C1-C12-烷基和/或C1-C4-烷氧基取代的苯基;
或R38和R39一起是任选被O、N(R43)或S***的C2-C8-亚烷基,或R38和R39一起是任选被羟基、C1-C4-烷氧基和/或(CO)O(C1-C4-烷基)取代的C2-C8-亚烷基;
o是1-15的整数;
R40是C1-C8-烷基,C3-C5-链烯基,苯基-C1-C3-烷基,C1-C4-羟烷基或苯基;
R41是任选被一个或多个O或S***的C2-C16-亚烷基;
R42是C1-C18-烷基,未被取代的或被卤素,C1-C12-烷基和/或C1-C8-烷氧基取代的萘基或苯基;和
R43是C1-C8-烷基,苯基-C1-C3-烷基,CH2CH2-COO(C1-C8-烷基),CH2CH2CN,CH2CH2-COO(CH2CH2O)o-H或
Ar3是
R20,R21,R22,R23,R24,R25,R44,R45,R46,R47和R48彼此独立地是选自氢,烷基,芳基,芳基-烷基,卤素,烷基-O-,芳基-O-,芳基-烷基-O-,芳基-N-,烷基-N-,芳基-烷基-N-,烷基-S-,芳基-S-,芳基-烷基-S-,NO-,氰基,羧酸酯,羧酰胺,酮或醛中的基团和其中R20,R21,R22和/或R23任选形成环结构和其中R24,R25,R44,R45,R46,R47和R48任选与R20,R21,R22和R23之间独立地形成一个或多个环结构。
因此,在本发明的上下文中适合作为光潜碱的是式IIa、IIb和IIc的化合物
A1-Z1(IIa) A2-Z2(IIb) A3-Z3(IIc),
其中A1,A2,A3,Z1,Z2和Z3如以上所定义。
显然光潜碱化合物可以单独使用或彼此以任何结合方式使用。
作为芳族或杂芳族基团的R1和R13是遵循Hückel 4n+2规则的基团。
例子是苯基,联苯基,萘基,菲基,蒽基,芘基,5,6,7,8-四氢-2-萘基,5,6,7,8-四氢-1-萘基,噻吩基,苯并[b]噻吩基,萘并[2,3-b]噻吩基,噻蒽基,二苯并呋喃基,苯并吡喃基,呫吨基,噻吨基,氧硫杂蒽基(phenoxathiinyl),吡咯基,咪唑基,吡唑基,吡嗪基,嘧啶基,哒嗪基,吲嗪基,异吲哚基,吲哚基,吲唑基,嘌呤基,喹嗪基,异喹啉基,喹啉基,2,3-二氮杂萘基,萘啶基,喹喔啉基,喹唑啉基,噌啉基,喋啶基,咔唑基,β-咔啉基,菲啶基,吖啶基,萘嵌间二氮杂苯基,菲咯啉基,吩嗪基,异噻唑基,吩噻嗪基,异噁唑基,呋咱基,三联苯基,茋基,芴基和吩噁嗪基。优选的是苯基,联苯基,萘基,菲基,蒽基,尤其是苯基。全部上述基团是未被取代的或被以上定义的基团取代。
C1-C20烷基是线性或支链的并且例如是C1-C18-,C1-C14-,C1-C12-,C1-C8-,C1-C6-或C1-C4烷基。例子是甲基,乙基,丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,戊基,己基,庚基,2,4,4-三甲基戊基,2-乙基己基,辛基,壬基,癸基,十二烷基,十四烷基,十五烷基,十六烷基,十八烷基和二十烷基。
C1-C18烷基,C1-C14烷基,C1-C12烷基,C1-C8烷基,C1-C6烷基和C1-C4烷基具有以上对于至多相应数量的C原子的C1-C20烷基所给出的相同含义。
苯基-C1-C3烷基例如是苄基,苯基乙基,α-甲基苄基或α,α-二甲基苄基,尤其是苄基。取代的苯基-C1-C3烷基被取代一至四次,例如一次,两次或三次,尤其两次或三次,优选在苯基环上。
C1-C12烷氧基是线性或支链的并且例如是C1-C10-,C1-C8-,C1-C6-或C1-C4-烷氧基。例子是甲氧基,乙氧基,丙氧基,异丙氧基,正丁氧基,仲丁氧基,异丁氧基,叔丁氧基,戊氧基,己氧基,庚氧基,2,4,4-三甲基戊氧基,2-乙基己氧基,辛氧基,壬氧基,癸氧基或十二烷氧基,尤其是甲氧基,乙氧基,丙氧基,异丙氧基,正丁氧基,仲丁氧基,异丁氧基,叔丁氧基,尤其是甲氧基。
C1-C12羟烷基例如是如上所述的但被OH单-或多取代的C1-C10-,C2-C10-,C1-C8-,C2-C8-,C2-C4-或C1-C4烷基。
C1-C20卤代烷基是被卤素单-或多-取代的线性或支链的C1-C18-,C1-C14-,C1-C12-,C1-C10-,C1-C8-,C1-C6-或C1-C4-烷基,该烷基例如是以上定义的。该烷基例如是单-或多-卤化的,至多全部H-原子被卤素所交换。被一个或多个卤素取代的C1-C20烷基例如是Cn[HxHaly]2n+1,其中x+y之和=2n+1和Hal是卤素,优选F。例子是氯甲基,三氯甲基,三氟甲基或2-溴丙基,尤其是三氟甲基或三氯甲基。
C5-C12环烷基例如是环戊基,环己基,环辛基,环十二烷基,尤其是环戊基和环己基,优选环己基。
在本申请的上下文中的C5-C12环烷基被理解为至少包括一个环的烷基。例如环丙基,甲基-环戊基,环戊基,环己基,甲基-或二甲基环己基,环辛基,尤其是环戊基和环己基,优选环己基也是所指。其它例子是例如如下结构:
例如
以及桥连或稠合的环体系,例如
也表示被该术语覆盖。
C1-C8烷硫基是线性或支链的并且例如是C1-C6-或C1-C4烷硫基。例子是甲硫基,乙硫基,丙硫基,异丙硫基,正丁硫基,仲丁硫基,异丁硫基,叔丁硫基,戊硫基,己硫基,庚硫基,2,4,4-三甲基戊硫基,2-乙基己硫基或辛硫基,尤其是甲硫基,乙硫基,丙硫基,异丙硫基,正丁硫基,仲丁硫基,异丁硫基,叔丁硫基,优选甲硫基。
C2-C20-链烯基例如是单或多不饱和的,线性或支链的并且例如是C2-C18-,C2-C10-,C2-C8-,C2-C6-或C2-C4链烯基。例子是烯丙基,甲基烯丙基,乙烯基,1,1-二甲基烯丙基,1-丁烯基,3-丁烯基,2-丁烯基,1,3-戊二烯基,5-己烯基或7-辛烯基,尤其是烯丙基或乙烯基。
C2-C18-炔基是单或多不饱和的,线性或支链的并且例如是C2-C8-,C2-C6-或C2-C4炔基。例子是乙炔基,丙炔基,丁炔基,1-丁炔基,3-丁炔基,2-丁炔基,戊炔基,己炔基,2-己炔基,5-己炔基,辛炔基,等等。
C1-C20亚烷基是线性或支链的,例如C1-C18-,C1-C12-,C1-C10-,C1-C8-,C1-C6-,C1-C4亚烷基,例如亚甲基,亚乙基,亚丙基,1-甲基亚乙基1,1-二甲基亚乙基,亚丁基,1-甲基亚丙基,2-甲基-亚丙基,亚戊基,亚己基,亚庚基,亚辛基,亚壬基,亚癸基,亚十二烷基,亚十四烷基,亚十六烷基或亚十八烷基。
被O或S***一次或多次的C2-C20亚烷基是线性或支链的并且例如被O或S***1-9次,例如1-7次或一次或两次。这产生例如下列结构单元:CH2-O-CH2,CH2-S-CH2,CH2CH2-O-CH2CH2,等等。该***原子是非连续的。
卤素是氟,氯气,溴和碘,尤其是氟,氯和溴,优选氟和氯。
如果R4和R6一起形成C2-C12-亚烷基桥;或
R5和R7,与R4和R6之间独立地,一起形成C2-C12亚烷基桥,例如形成下面的结构:
如果R18和R19与它们所连接到的氮原子一起形成任选被O,S,CO或NR37***的5-,6-或7-员环;则形成饱和或不饱和的环,例如氮杂环丙烷,吡咯,吡咯烷,噁唑,吡啶,1,3-二嗪,1,2-二嗪,哌啶或吗啉,优选吗啉。
光潜碱化合物的制备是已知并且例如描述在WO 98/32756,WO98/41524和WO 03/33500。这些说明书还提供了此类化合物的具体例子。
也适合作为光潜碱给体的是描述在EP 898202中的α-氨基酮化合物,例如(4-吗啉代苯甲酰基)-1-苄基-1-二甲基氨基-丙烷或(4-甲硫基苯甲酰基)-1-甲基-1-吗啉代-乙烷和公开在WO 05/007637中的化合物。
式Z3-A3的光潜碱的制备和使用例如公开在WO 97/31033中。
其它光碱产生剂的概述以综述的形式由M.Shirai和M.Tsunooka给出在Prog.Polym.Sci.,Vol.21,1-45(1996).和由J.Crivello,K.Dietliker给出在“Photoinititiators for Free Radical Cationic & AnionicPhotopolymerisation”,第2版,“Chemistry & Technology of UV & EBFormulation for Coatings,Inks & Paints”系列中的卷III,John Wiley/SITATechnology Limited,London,1998,Chapter IVI(p.479-544)。
特别适合的组合物是其中光潜碱具有式(I)的组合物
其中
R1是芳族或杂芳族基团,它能够吸收在200-650nm的波长范围内的光并且它是未被取代的或被一个或多个C1-C18-烷基,C2-C18-链烯基,C2-C18-炔基,C1-C18-卤代烷基,NR8R9,CN,OR10,SR10,COR11,COOR12,卤素或以下基团所取代:
或R1是
R2和R3彼此独立地是氢,C1-C18-烷基,C1-C18-链烯基,C3-C18-炔基或苯基,该苯基是未被取代的或被一个或多个C1-C18-烷基,CN,OR12,SR12,卤素,或C1-C18-卤代烷基取代;
R5是C1-C18-烷基或NR10R11;
R4,R6,R7,R8和R9彼此独立地是氢或C1-C18-烷基;或
R4和R6一起形成C2-C12-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;或
R5和R7,与R4和R6独立地,一起形成C2-C12亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;或,如果R5是NR10R11,R7和R11一起形成C2-C12-亚烷基桥基,这一桥基是未被取代的或被一个或多个C1-C4-烷基取代;
R10,R11和R12彼此独立地是氢或C1-C18烷基;
R13是芳族或杂芳族基团,它能够吸收在200-650nm波长范围内的光并且它是未被取代的或被一个或多个的取代基C1-C18-烷基,C2-C18-链烯基,C2-C18-炔基,C1-C18-卤代烷基,NR8R9,CN,OR10,SR10,COR11,COOR12,或卤素取代;
R14是氢或C1-C18-烷基;
R15是氢,C1-C18-烷基或苯基,该苯基是未被取代的或被一个或多个C1-C18-烷基,乙烯基,C3-C18-链烯基,C3-C18-炔基,C1-C18-卤代烷基,苯基,NR8R9,CN,OR10,SR10,COR11,COOR12,或卤素取代。
优选的是作为光潜碱(a)的如上所述的组合物,它包括式(I)化合物:
其中
R1是苯基,联苯基,萘基,蒽基或蒽醌基,它们全部是未被取代的或被一个或多个C1-C4-烷基,C2-C4-链烯基,CN,OR10,SR10,COOR12,卤素或以下基团所取代:
或R1是
R2和R3彼此独立地是氢或C1-C6-烷基;
R4和R6一起形成C2-C6-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;
R5和R7一起形成C2-C6-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;
R10,R11和R12彼此独立地是氢或C1-C6-烷基;
R13是苯基,联苯基,萘基,蒽基或蒽醌基,它们全部是未被取代的或被一个或多个C1-C4-烷基,C2-C4-链烯基,CN,OR10,SR10,COOR12,或卤素所取代;
R14是氢;和
R15是氢或C1-C4-烷基。
基团的含义如上所述。
取代的苯基,联苯基,萘基,蒽基或蒽醌基例如被取代一次到四次,例如一次,两次或三次,尤其是两次或三次。在苯基环上的取代基优选在2位上或在苯基环上的2,6或2,4,6构型。
萘基表示1-萘基和2-萘基。
术语“和/或”用来表达以下事实:不只一个所定义的备选方案(取代基)可以存在,而且同样可能一起有在所定义的那些当中的两种或多种不同的备选方案(取代基),即不同的备选方案(取代基)的混合物。
术语“至少”用于定义一个或一个以上,例如一个或两个或三个,优选一个或两个。
在说明书和权利要求中,词“包括”被理解为指包括了所定义的主题或所定义组的主题,但不排除没有明确地提到的任何其它物质,除非另外特意描述。
因此,适合作为组合物中的光潜碱的化合物是式(Ia)的化合物,
其中
x是1-5的整数;
y和z彼此独立地是0-6的整数;
R8和R9彼此独立地是C1-C4烷基;
R1,R2和R3如上所定义。
如果在式Ia的上述化合物中存在一个以上的R20或R21,则该基团的定义不需要相似。换句话说:一个R20可以表示C1烷基,而另一个R20可以是C4烷基,等等。
因此特别令人感兴趣的是包括式Ia化合物的如上所述的组合物。
必须强调式(Ib),(Ic)和(Id)的化合物,
其中R1,R2和R3如上所定义。
尤其令人感兴趣的是式(Ib)的化合物。
更令人感兴趣的是式(Ie)的化合物
其中R2,R3,R13,R14和R15如上所定义。
尤其优选的是
特别是
其它光潜碱的例子是(4-吗啉代苯甲酰基)-1-苄基-1-二甲基氨基-丙烷,(4-甲硫基苯甲酰基)-1-甲基-1-吗啉代-乙烷,(3,4-二甲氧基苯甲酰基)-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-(2-羟乙基氨基)苯甲酰基)-1-苄基-1-二甲基氨基-丙烷,
其中1是约1-10的整数,k是约2-10的整数,尤其是5,h是1-10的整数,尤其是2或
本发明的实施方案涉及以上定义的式II的化合物或以上定义的式I的化合物作为光潜碱催化剂(a)用于包含(b)封闭异氰酸酯和H-给体(c)的组合物的固化中的用途。
封闭异氰酸酯在现有技术中是已知的并且例如在综述文章中由D.A.Wicks,Z.W.Wicks在Progress in Organic Coatings,41(2001),1-83,以及由C.Gürtler,M.Homann,M.Mager,M.Schelhaas,T.Stingl,Farbe+Lack2004,110(12),34进行描述;两个文件被引入这里供参考。
术语“异氰酸酯”和“异硫氰酸酯”这里指单-和多异氰酸酯和指单-和多异硫氰酸酯。
一般该术语复盖了含有一个或多个-N=C=Y基团的任何化合物,其中Y是氧或硫。适合于本发明的多异氰酸酯的例子包括脂族化合物如三亚甲基,四亚甲基,五亚甲基,六亚甲基,1,2-亚丙基,1,2-亚丁基,2,3-亚丁基,1,3-亚丁基,次乙基和丁叉基二异氰酸酯。另外,亚环烷基二异氰酸酯也能够使用,如1,3-环戊烷,1,4-环己烷和1,2-环己烷二异氰酸酯。芳族二异氰酸酯也是合适的,如间亚苯基,对亚苯基,4,4’-二苯基,1,5-亚萘基和1,4-亚萘基二异氰酸酯以及脂族-芳族二异氰酸酯如4,4’-二亚苯基甲烷,2,4-或2,6-甲代亚苯基或它们的混合物,4,4’-甲苯胺和1,4-亚二甲苯基二异氰酸酯。取代的芳基或芳族二异氰酸酯也可以使用,如联甲氧基苯胺二异氰酸酯,4,4’-二苯基醚二异氰酸酯和氯二亚苯基二异氰酸酯,1,8-二异氰酸根合-甲烷,1-甲基-2,4-二异氰酸根合环己烷,氯亚苯基二异氰酸酯,二苯甲烷-4,4’-二异氰酸酯和萘-1,5-二异氰酸酯。另外,三异氰酸酯如三苯基甲烷-4,4’,4”-三异氰酸酯,1,3,5-三异氰酸酯苯和2,4,6-三异氰酸酯甲苯也能够使用。其它四异氰酸酯都可以使用,例如4,4’-联苯酚-二甲基甲烷-2,2’,5,5’-四异氰酸酯以及其它异氰酸酯如亚二甲苯基-二异硫氰酸酯,异丙基苯-二异氰酸酯和聚合多异氰酸酯如甲苯二异氰酸酯二聚体和三聚物;联甲氧基苯胺二异氰酸酯(CAS登记No.91-93-0);甲苯胺二异氰酸酯(CAS登记No.91-97-4);六亚甲基二异氰酸酯的缩二脲(CAS登记No.4035-89-6);异佛尔酮二异氰酸酯(CAS登记No.4098-71-9);聚合物联苯酚乙烷二异氰酸酯(CAS登记No.9016-87-9)或4,4’-二环己基甲烷二异氰酸酯。异氰酸酯的各种混合物也可使用,尤其是两种,三种或四种组分混合物。
有机多异氰酸酯也可以是从多元醇和多异氰酸酯得到的预聚物,这样多元醇含有异氰酸酯基团,其中多元醇包括聚醚多醇或聚酯多元醇或简单的多元醇如二醇,其中包括乙二醇和丙二醇以及甘油,三羟甲基丙烷,己烷三醇,季戊四醇,等等。
合适的异氰酸酯组分的以上概述不应该理解为限制本发明,但仅仅是举例说明的例子而已。
正如这里所指出,本发明的组分(b)的异氰酸酯包括封闭的异氰酸酯,也就是说反应活性的异氰酸酯基团与任何合适的封闭剂反应。
组分(b)的例子还可以是双(环脲)。这些是封闭的脂族二异氰酸酯并且在一些实施方案中是优选的,因为在反应活性异氰酸酯基团释放时没有形成副产物。这些化合物能够称为自封闭的异氰酸酯。这些双环脲的例子已描述在Ulrich,ACS Svmm.Ser.172 519(1981,Sherwood,J.Coat.Technol.54(689),61(1982)和Kirk-Othmer Encyclopedia of ChemicalTechnology,第3版,23卷,p.584,它们全部被引入这里供参考。
特别适合作为组分(b)的是选自脂族或芳族多异氰酸酯,二异氰酸酯,三异氰酸酯和四异氰酸酯中的化合物。
异氰酸酯的合适封闭剂是现有技术中已知的那些,例如醇,酚,胺,酰亚胺,酰胺,胍,脒,***,吡唑,活性亚甲基化合物,酮肟,肟,丙二酸酯,乙酰乙酸烷基酯,甲酸酯,内酰胺,咪唑,***,吡唑,CH-酸性环酮和硫醇。
例子是脂族,脂环族,芳族,或烷基一元醇或酚类化合物,例如,低级脂族醇,其中包括甲醇,乙醇,氯乙基醇,丙醇,丁醇,戊醇,己醇,庚醇,辛醇,壬醇,癸醇和月桂醇,3,3,5-三甲基己醇等等。芳族烷基醇包括例如苯甲醇和乙基苯基甲醇。二醇醚也可以使用,如乙二醇单乙基醚,乙二醇单丁基醚和它们的等同物。可使用的酚类化合物的例子包括苯酚,取代的酚类如甲酚,二甲苯酚,硝基酚,氯苯酚,乙基苯酚,叔丁基苯酚和2,5-二-叔丁基-4-羟基甲苯。
可使用的其它封闭剂的例子包括叔羟胺,如二乙基乙醇胺,内酰胺如己内酰胺和肟如甲基乙基酮肟,丙酮肟和环己酮肟。
具体的例子是丁酮肟,二异丙基胺,1,2,4-***,二甲基-1,2,4-***,咪唑,丙二酸和乙酸的乙基化物,丙酮肟,3,5-二甲基吡唑,ε-己内酰胺,N-甲基-,N-乙基,N-(异)丙基,N-正丁基,N-异丁基-,N-叔丁基苄基胺,或1,1-二甲基苄基胺,N-烷基-N-1,1-二甲基甲基苯基胺;苄基胺和具有活化双键的化合物如丙二酸酯的加合物,N,N-二甲基氨基丙基苄基胺和包含叔胺基团的其它化合物,若合适的话取代的苄基胺和/或二苄基胺。
肟和酚在一些情况下的使用是所希望,因为用这些肟或酚封闭的一些具体多异氰酸酯在较低温度下解封闭。
合适CH-酸性酮的例子已给出在WO 04/058849中并引入这里供参考。优选的是环戊酮-2-羧基甲基酯,环戊酮-2-羧基乙基酯,环戊酮-2-甲腈,环己酮-2-羧基甲基酯,环己酮-2-羧基乙基酯,环戊酮-2-羰基甲烷,尤其是环戊酮-2-羧基甲基酯,环戊酮-2-羧基乙基酯,环己酮-2-羧基甲基酯和环己酮-2-羧基乙基酯,尤其是环戊酮-2-羧基乙基酯和环己酮-2-羧基乙基酯。
因此本发明的主题是如上所述的组合物,其中封闭剂是环戊酮-2-羧基甲基酯,环戊酮-2-羧基乙基酯,环戊酮-2-甲腈,环己酮-2-羧基甲基酯,环己酮-2-羧基乙基酯,环戊酮-2-羰基甲烷。
显然,不同的封闭剂的混合物也可使用并且可用于目前所要求的组合物中的封闭异氰酸酯可具有不同的封闭基团。
本发明的主题因此是组合物,其中异氰酸酯的封闭剂选自醇,酚,胺,酰亚胺,酰胺,胍,脒,***,吡唑,活性亚甲基化合物,酮肟,肟,甲酸酯,内酰胺,咪唑,CH-酸性环酮,优选环戊酮-2-羧基乙基酯,和硫醇。
尤其优选的封闭剂是CH-酸性酮。
合适的封闭剂是醇,酚,胺,酰亚胺,酰胺,胍,脒,***,吡唑,活性亚甲基化合物,酮肟,肟,甲酸酯,内酰胺,咪唑和硫醇。
本发明的封闭的反应活性异氰酸酯或异硫氰酸酯与含有活性氢的官能化合物或官能组分反应,该活性氢由描述在J.Am.Chem.Soc.,Vol.49,p.3181(1927)中的泽列维季诺夫(Zerewitinoff)方法测定。含有活性氢原子的这些化合物或组分包括用于制造前面所述的多异氰酸酯预聚物的化合物,例如包括聚醚多醇或聚酯多元醇(也就是说含有羟基的化合物)在内的多元醇。
另外,含有氨基的化合物也包括在属于含有活性氢的官能组分的那些材料之内。再次,一般来说,由泽列维季诺夫(Zerewitinoff)方法测定对于活性氢给出正试验结果的全部化合物均是合适的。
这些化合物或组分包括但不限于醇,酚,硼酸,羧酸,过羧酸(percarboxylic acids)和磺酸等等。也包括在这一组内的是含有氮-氢键的化合物,如胺,酰胺,内酰胺,脲,尿烷,脲基甲酸酯,缩二脲,酰基脲,硫脲,腙,肟,脒,羟胺,腙,异羟肟酸,硝胺,重氮氨基化合物和磺酰胺。
含有硫-氢键的化合物也包括在内,如硫醇,苯硫酚和硫代酸。包括在内的其它化合物是卤素酸,含有活性亚甲基的化合物和能够形成烯醇的化合物如丙酮,丙二酸酯,乙酰乙酸酯,乙酰丙酮和硝基甲烷及混杂的含活性氢的化合物如炔属化合物和膦酸二烷基酯。
早已描述的含有两个或多个或任何一个或混合的活性氢基团的化合物也包括在内。
合适的其它组分(c)是聚醚多元醇,例如具有300-20000,尤其1000-12000,优选2000-6000的分子量。
所述较高分子量的聚醚多元醇一般从普通的聚氨酯化学中获知并且由已知方法通过合适起始剂分子的烷氧基化来制备。
起始剂分子的例子是常见的多元醇,如乙二醇,1,2-或1,3-丙二醇,1,4-丁二醇,1,6-己二醇,新戊基二醇,2-乙基己二醇-1,3,甘油,三羟甲基丙烷,季戊四醇,山梨醇,以及此类多元醇与包含羟基的脂族或芳族二羧酸的低分子量酯。其它例子是此类多元醇或此类改性或未改性醇的任何混合物,水,具有至少两个N-H键的有机多元胺或此类起始剂分子的任何混合物的乙氧基化和丙氧基化反应的低分子产物。
适合于烷氧基化的是环醚如四氢呋喃(THF)和/或环氧烷烃如环氧乙烷,环氧丙烷,环氧丁烷,苯乙烯氧化物或表氯醇,尤其是环氧乙烷和/或环氧丙烷,它们用于烷氧基化反应的任何混合物或序列中。
所考虑的其它组分(c)是胺,例如每分子具有至少两个伯胺基团和任选另外具有仲氨基团的多元胺。该多元胺例如具有60到500的平均分子量。合适的是例如乙二胺,1,2-和1,3-二氨基丙烷,1,4-二氨基丁烷,2,2,4-和/或2,4,4-三甲基六亚甲基二胺,异构化二甲苯二胺,1,4-二氨基环己烷,4,4’-二氨基二环己基甲烷,1,3-二氨基环戊烷,4,4’-二氨基二环己基砜,4,4’-二氨基环己基丙烷-1,3,4,4’-二氨基环己基丙烷-2,2,3,3’-二甲基-4,4’-二氨基二环己基甲烷,3-氨基甲基-3,3,5-三甲基环己基胺(异佛尔酮二胺),3(4)-氨基甲基-1-甲基环己基胺,(工业级)双氨基甲基三环癸烷,八氢-4,7-甲撑茚-1,5-二甲烷胺或除了至少两个氨基之外还包含任何仲氨基团的胺,例如二亚乙基三胺或三亚乙基四胺。
尤其合适的是多胺,尤其上述分子量的二胺,它包含一个或多个脂环族环。例子是以上所述的的那些。
适合作为组分(c)的此外是含硫醇基的化合物,它一般通过含羟基的化合物与含硫醇基的酸进行反应来制备。典型地,合适的硫醇是单体的、低聚的脂族或芳族硫醇。
包含至少一个硫醇基的异氰酸酯反应活性化合物(c)的例子包括包含至少两个硫醇官能团的硫醇官能化化合物和包含至少一个硫醇官能团和一个羟基官能团的化合物。这些化合物的混合物也可用于本发明的组合物中。
合适的含硫醇基的化合物一般通过含羟基的化合物与含硫醇基的酸如3-巯基丙酸、2-巯基丙酸、硫代水杨酸、巯基琥珀酸、巯基乙酸或半胱氨酸进行反应来制备。合适的含羟基的化合物的例子是二醇,三醇,和四醇,如1,4-丁烷二醇,1,6-己烷二醇,2,2-二甲基-1,3-丙烷二醇,2-乙基-2-丙基-1,3-丙烷二醇,1,2-,1,3-和1,4-环己烷二醇,和相应的环己烷二甲醇,1,1,1-三羟甲基丙烷,1,2,3-三羟甲基丙烷,和季戊四醇。根据此类方法制备的化合物的例子包括季戊四醇四(3-巯基丙酸酯),季戊四醇四(2-巯基乙酸酯),三羟甲基丙烷三(3-巯基丙酸酯),三羟甲基丙烷三(2-巯基丙酸酯),和三羟甲基丙烷三(2-巯基乙酸酯)。用三羟甲基丙烷三(3-巯基丙酸酯)和季戊四醇四(3-巯基丙酸酯)已经获得良好的结果。根据此类方法制备的化合物的其它例子包括以起始剂多元醇例如三羟甲基丙烷和二羟甲基丙酸为基础的高度支化多元醇芯。这一多元醇随后用3-巯基丙酸和异壬酸进行酯化。这些方法例如已描述在欧洲专利申请EP448224和国际专利申请WO 93/17060中。
制备包括至少两个硫醇官能团的化合物的其它合成方法包括(i)芳基或烷基卤与NaHS反应分别将侧挂硫醇基引入到烷基和芳基化合物中;(ii)格利雅试剂与硫反应,从而将侧挂硫醇基引入结构中;(iii)聚硫醇与聚烯烃根据迈克尔加成反应、亲核反应、亲电子反应或自由基反应进行反应;(iv)硫醇官能化醇和异氰酸酯官能化合物的反应,和(v)二硫化物的还原。
包含至少一个硫醇官能团和一个羟基官能团的化合物可以例如具有根据下式的结构:T[(C3H3O)nCH2CHOHCH2SH]3,其中T是三醇如三羟甲基丙烷或甘油。此类化合物的例子能够以商标Henkel Capcure3/800从Henkel商购。
二者择一地,包含至少一个硫醇基的异氰酸酯反应活性化合物(c)是具有例如聚酯树脂,聚氨酯树脂,聚丙烯酸酯树脂,或聚醚树脂作为骨架的树脂。这些异氰酸酯反应活性化合物也可包括羟基。包含至少一个硫醇基的异氰酸酯反应活性化合物例如是从(1)至少一种多羧酸或它的反应活性衍生物,(2)至少一种多元醇,和(3)至少一种硫醇官能化羧酸制备的聚酯。该聚酯优选具有支链结构。支链聚酯通常通过多羧酸或它的反应活性衍生物,如相应酸酐或低级烷基酯,与多元醇之间的缩合反应来获得,当至少一种反应物具有至少3个官能团时。合适多羧酸或它的反应活性衍生物的例子是四氢化邻苯二甲酸,四氢邻苯二甲酸酐,六氢邻苯二甲酸,六氢邻苯二甲酸酐,甲基六氢邻苯二甲酸,甲基六氢邻苯二甲酸酐,环己烷二甲酸二甲基酯,1,4-环己烷二甲酸,1,3-环己烷二甲酸,邻苯二甲酸,邻苯二甲酸酐,间苯二酸,对苯二甲酸,5-叔丁基间苯二酸,偏苯三酸酐,马来酸,马来酸酐,富马酸,琥珀酸,琥珀酸酐,十二烷基琥珀酸酐,琥珀酸二甲基酯,戊二酸,己二酸,己二酸二甲酯,壬二酸,和它们的混合物。
合适多元醇的例子包括三羟甲基丙烷,三羟甲基乙烷,甘油,1,2,6-己烷三醇,乙二醇,1,2-丙二醇,1,3-丙二醇,2-甲基丙烷-1,3-二醇,新戊二醇,2-丁基-2-乙基-1,3-丙烷二醇,环己烷-1,4-二甲醇,新戊二醇和羟基特戊酸的单酯,氢化双酚A,1,5-戊烷二醇,3-甲基戌烷二醇,1,6-己烷二醇,2,2,4-二甲基戊烷-1,3-二醇,二羟甲基丙酸,季戊四醇,双三羟甲基丙烷,双季戊四醇,和它们的混合物。
合适硫醇的具体例子包括季戊四醇四(巯基乙酸酯),季戊四醇四(巯基丙酸酯),4,4’-硫代双苯硫醇,二硫苏糖醇,巯基乙醇,十二烷硫醇,巯基乙酸,3-巯基丙酸,或乙二醇二巯基乙酸酯。
组分(c)也可包括含环氧基的树脂或属于伯胺和/或仲胺与含环氧基的树脂的加合物的树脂或属于胺-酸盐与聚环氧化物的加合物的树脂。
单独使用的或用于形成加合物的环氧材料能够是任何单体或聚合化合物或每分子平均具有一个或多个环氧基的化合物的混合物。特别有用种类的聚环氧化物是多酚如双酚A的聚缩水甘油基醚或从线型酚醛树脂或类似多酚树脂生产的聚环氧化物。这些环氧树脂尤其适合于以伯或仲胺和尤其是仲胺为基础的环氧树脂的胺加合物的制备并且其中该加合物进一步与酸反应以便在加合物中提供阳离子基团。
多元醇的其它聚缩水甘油基醚可以使用,如以乙二醇和类似物为基础的那些,以及多羧酸的聚缩水甘油基酯。
从烯属不饱和脂环族化合物的环氧化得到的聚环氧化物也能够使用。可使用的其它含环氧基的化合物和树脂包括含氮的双环氧化合物,如公开在US 3365471;US 3391097;US 3450711;US 3312664;US3503979和GB 1172916中的那些,它们全部被引入这里供参考。
可使用的另一类型的聚环氧化物是通过聚合不饱和的含环氧基的单体例如缩水甘油基丙烯酸,缩水甘油丙烯酸酯或甲基丙烯酸酯,含羟基的不饱和单体如丙烯酸或甲基丙烯酸的羟烷基酯以及至少一种其它不饱和单体如苯乙烯,α-甲基苯乙烯,乙烯基甲苯和类似物或烯烃酸和丙烯酸或甲基丙烯酸的酯如丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸甲酯和类似物所形成的丙烯酸类聚合物。这些环氧树脂尤其适合于具有季铵盐基团的增溶化聚环氧化物加合物的制备,例如具有从烯属不饱和缩水甘油基化合物、丙烯酸或甲基丙烯酸的羟烷基酯和至少一种其它烯属不饱和单体的互聚反应得到的骨架的那些。多酚的聚缩水甘油基醚也可用作在具有季铵盐基团的增溶化聚环氧化物加合物的制备中的环氧树脂。
属于伯胺和/或仲胺的加合物的环氧树脂例如通过此类环氧树脂与胺如水溶性氨基化合物进行反应而获得,该水溶性氨基化合物包括单-和二烷基胺如甲基胺,乙基胺,丙胺,丁基胺,二甲胺,二乙基胺,二丙基胺,二丁基胺,甲基丁基胺,和类似物。更高分子量的单胺也可使用,其中优选的是分子是更柔性的。此外,低分子量和高分子量胺类的混合物也可用于改进树脂性能。
含季铵基团的环氧树可通过聚环氧化物与胺-酸盐,优选叔胺-酸盐,进行反应以形成含季胺盐基团的树脂来获得。伯和仲胺-酸盐都可以使用,但是叔胺-酸盐是优选的。可使用胺-酸盐的例子包括硼酸或离解常数大于硼酸的离解常数的酸和优选离解常数大于约1×10-5的有机酸的胺盐,如乳酸,乙酸,甲酸,丙酸,丁酸,盐酸,磷酸,硫酸和类似物。该胺-酸盐和聚环氧化物在水存在进行反应和因此获得加合物。
含环氧基的树脂的此类胺加合物的其它例子已描述在US 4031050,US 4017438中以及通过聚环氧化物与胺的反应所制备的含活性氢原子和季铵基团的树脂的例子已描述在US 4101486中,这些专利全部被引入这里供参考。
可与封闭异氰酸酯(c)反应的官能化组分例如也是以具有至少一个活性胺氢的酮亚胺封闭胺为基础的多官能化合物,其中酮亚胺封闭胺与环氧化合物反应。这些化合物例如通过二亚乙基三胺和甲基异丁基酮的二酮亚胺与聚环氧化物反应来获得。
例如根据本发明所使用的各种具体的异氰酸酯和硫异氰酸酯材料以及含有活性氢的官能化合物或组分进一步描述在US 3084177;US3240730;US 339212和US 3392153中,它们全部被引入这里供参考。
因此所关注的是如上所述的组合物,其中氢供体组分(c)是选自醇,多元醇,酚类,硼酸,羧酸类,磺酸,胺,酰胺,内酰胺,脲,尿烷,脲基甲酸酯,缩二脲,酰基脲,硫脲,腙,肟,脒,羟胺,腙,异羟肟酸,硝胺,重氮氨基化合物,磺酰胺,硫醇,多硫醇,苯硫酚,硫代酸,卤素酸和含环氧基的化合物之中,尤其选自醇,多元醇,多硫醇,苯酚,胺,酰胺,羟胺和含环氧基的化合物之中的至少一种化合物。
尤其,适合作为组分(c)的是胺,羟基官能化合物和硫醇化合物。
组合物含有光潜碱,组分(a),含量例如是基于总组合物的0.01-20wt%,优选0.01-10wt%。
组合物含有封闭异氰酸酯,组分(b),含量例如是基于总组合物的5-95wt%,优选20-80wt%。比值(b):(c)例如是约2:1-1:2,优选1.2:1-1:1.2。封闭异氰酸酯的分子量MW例如是约100-50000,尤其200-20000。
除光潜碱(a)之外,该光可聚合的组合物可包括各种添加剂(d)。
添加剂(d)例如是使光谱灵敏度位移或增宽的附加助引发剂或增感剂。一般这些是芳族羰基化合物,例如二苯甲酮,噻吨酮,蒽醌和3-酰基香豆素衍生物或染料如曙红,若丹明和赤藓红染料,它们例如通过能量转移或电子转移改进整个量子产量。能够作为助引发剂添加的合适染料的例子是三芳基甲烷,例如孔雀绿,二氢吲哚,噻嗪,例如亚甲基蓝,呫吨酮,噻吨酮,噁嗪,吖啶或吩嗪,例如番红,和下式的若丹明:
其中R是烷基或芳基和R′是氢或烷基或芳基,例如若丹明B,若丹明6G或紫胺R,以及磺基若丹明B或磺基若丹明G。同样合适的是荧光酮,例如5,7-二碘-3-丁氧基-6-荧光酮。
适合作为组分(d)的光敏剂的其它具体例子是
1.噻吨酮类
噻吨酮,2-异丙基噻吨酮,2-氯噻吨酮,1-氯-4-丙氧基噻吨酮,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-苯基硫基噻吨酮,3,4-二-[2-(2-甲氧基乙氧基)乙氧基羰基]-噻吨酮,1,3-二甲基-2-羟基-9H-噻吨-9-酮2-乙基己基醚,1-乙氧基羰基-3-(1-甲基-1-吗啉基乙基)-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-3,4-二甲酰亚胺,N-辛基噻吨酮-3,4-二甲酰亚胺,N-(1,1,3,3-四甲基丁基)-噻吨酮-3,4-二甲酰亚胺,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-羧酸聚乙二醇酯,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-丙铵氯化物;
2.二苯甲酮类
二苯甲酮,4-苯基二苯甲酮,4-甲氧基二苯甲酮,4,4’-二甲氧基二苯甲酮,4,4’-二甲基二苯甲酮,4,4’-二氯二苯甲酮,4,4’-双(二甲基氨基)二苯甲酮,4,4’-双(二乙基氨基)二苯甲酮,4,4’-双(甲基乙基氨基)二苯甲酮,4,4’-双(对-异丙基苯氧基)二苯甲酮,4-甲基二苯甲酮,2,4,6-三甲基二苯甲酮,4-(4-甲基硫基苯基)-二苯甲酮,3,3’-二甲基-4-甲氧基二苯甲酮,2-苯甲酰基苯甲酸甲基酯,4-(2-羟乙基硫基)-二苯甲酮,4-(4-甲苯基硫基)二苯甲酮,1-[4-(4-苯甲酰基-苯基硫基)-苯基]-2-甲基-2-(甲苯-4-磺酰基)-丙烷-1-酮,4-苯甲酰基-N,N,N-三甲基苯甲铵氯化物,2-羟基-3-(4-苯甲酰基苯氧基)-N,N,N-三甲基-1-丙铵氯化物一水合物,4-(13-丙烯酰基-1,4,7,10,13-五氧杂十三烷基)-二苯甲酮,4-苯甲酰基-N,N-二甲基-N-[2-(1-氧代-2-丙烯基)氧基]乙基-苯甲铵氯化物;
3.香豆素类
香豆素1,香豆素2,香豆素6,香豆素7,香豆素30,香豆素102,香豆素106,香豆素138,香豆素152,香豆素153,香豆素307,香豆素314,香豆素314T,香豆素334,香豆素337,香豆素500,3-苯甲酰基香豆素,3-苯甲酰基-7-甲氧基香豆素,3-苯甲酰基-5,7-二甲氧香豆素,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,5,7-二乙氧基-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-噻吩甲酰基香豆素,3-(4-氰基苯甲酰基)-5,7-二甲氧香豆素,3-(4-氰基苯甲酰基)-5,7-二丙氧基香豆素,7-二甲基氨基-3-苯基香豆素,7-二乙基氨基-3-苯基香豆素,公开在JP 09-179299-A和JP 09-325209-A中的香豆素衍生物,例如7-[{4-氯-6-(二乙基氨基)-S-三嗪-2-基}氨基]-3-苯基香豆素;
4.3-(芳酰基亚甲基)-噻唑啉类
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.若丹宁类
4-二甲基氨基苯亚甲基若丹宁,4-二乙基氨基苯亚甲基若丹宁,3-乙基-5-(3-辛基-2-苯并噻唑啉叉基)-若丹宁,公开在JP 08-305019A中的式[1],[2],[7]的若丹宁衍生物;
6.其它化合物
乙酰苯,3-甲氧基乙酰苯,4-苯基乙酰苯,苯偶酰,4,4’-双(二甲基氨基)苯偶酰,2-乙酰基萘,2-萘醛,1-二甲胺基萘-5-磺酸衍生物,9,10-蒽醌,蒽,芘,氨基芘,苝,菲,菲醌,9-芴酮,二苯并环庚酮,酸性黄,呫吨酮,硫代米蚩酮,α-(4-二甲基氨基苄叉基)酮,例如2,5-双(4-二乙基氨基苄叉基)环戊酮,2-(4-二甲基氨基-苄叉基)-茚满-1-酮,3-(4-二甲基氨基-苯基)-1-茚满-5-基-丙烯酮,3-苯基硫代邻苯二甲酰亚胺,N-甲基-3,5-二(乙硫基)-邻苯二甲酰亚胺,N-甲基-3,5-二(乙硫基)邻苯二甲酰亚胺,吩噻嗪,甲基吩噻嗪,胺,例如N-苯基甘氨酸,4-二甲基氨基苯甲酸乙基酯,4-二甲基氨基苯甲酸丁氧基乙基酯,4-二甲基氨基乙酰苯,三乙醇胺,甲基二乙醇胺,二甲氨基乙醇,苯甲酸2-(二甲基氨基)乙酯,4-(二甲基氨基)苯甲酸聚(丙二醇)酯。
在本文上下文中同样合适的是染料与硼酸盐的结合物,按照例如在US 4772530,GB 2307474,GB 2307473,GB 2307472和EP 775706中所述。
根据本发明的组合物可以包括作为其它添加剂(d)的光还原性染料,例如,呫吨-,苯并呫吨-,苯并噻吨-,噻嗪-,派若宁-,紫菜碱-或吖啶染料,和/或能够被辐射所***的三卤甲基化合物。类似的组合物例如已描述在EP 445624中。
特别优选的是取代的二苯甲酮或噻吨酮。合适二苯甲酮的例子是二苯甲酮,4,4’-双(二甲基氨基)二苯甲酮,4,4’-双(二乙基氨基)二苯甲酮,4,4’-双(乙基甲基氨基)二苯甲酮,4,4’-二苯基二苯甲酮,4,4’-二苯氧基二苯甲酮,4,4’-双(对-异丙基苯氧基)二苯甲酮,4-甲基二苯甲酮,2,4,6-三甲基二苯甲酮,4-苯基二苯甲酮,2-甲氧基羰基二苯甲酮,4-苯甲酰基-4’-甲基二苯基硫醚,4-甲氧基-3,3’-甲基二苯甲酮,异丙基噻吨酮,氯噻吨酮,1-氯-4-丙氧基噻吨酮,2,4-二甲基噻吨酮,2,4-二乙基噻吨酮,1,3-二甲基-2-(2-乙基己氧基)噻吨酮。
同样优选的是二苯甲酮和/或噻吨酮的混合物,例如二苯甲酮和4-甲基二苯甲酮的混合物或4-甲基二苯甲酮和2,4,6-三甲基二苯甲酮的混合物。
因此所关注的也可以是包含作为其它添加剂(d)的光敏剂的如上所述组合物,该光敏剂选自二苯甲酮和它的衍生物,噻吨酮和它的衍生物,蒽醌和它的衍生物或香豆素和它的衍生物或染料如噁嗪,吖啶,吩嗪和若丹明,尤其二苯甲酮和它的衍生物,噻吨酮和它的衍生物,蒽醌和它的衍生物或香豆素和它的衍生物。相应衍生物的例子被收集在以上列举中。
其它常用添加剂(d),取决于预期用途,是荧光增白剂,填料,颜料,染料,润湿剂,流平剂,抗静电剂,流动改进剂和粘合促进剂,抗氧化剂,光稳定剂,例如UV吸收剂,例如羟基苯并***、羟苯基-二苯甲酮、草酰胺或羟苯基-s-三嗪型的那些。这些化合物能够在有或没有位阻胺(HALS)的情况下单独或以混合物使用。
组合物也可包括染料和/或白色和有色颜料。取决于应用的类型,使用有机和无机颜料。此类添加剂是所属技术领域的专业人员已知的,一些例子是二氧化钛颜料,例如金红石型或锐钛矿型的二氧化钛颜料,炭黑Russ,氧化锌,如锌白,氧化铁,如氧化铁黄,氧化铁红,铬黄,铬绿,钛镍黄,群青,钴蓝,钒酸铋,镉黄或镉红。有机颜料的例子是单-或双偶氮颜料,以及它们的金属配合物,酞花青颜料,多环颜料,如苝-,蒽醌-,硫靛蓝-,吖啶酮(chinacridone)-或三苯基甲烷颜料,以及二酮基吡咯并吡咯-,异二氢吲哚酮-,例如四氯异吲哚啉酮-,异吲哚啉-,二噁嗪-,苯并咪唑酮-和chinophthalone颜料。
这些颜料根据本发明的组合物可以单独使用或相结合使用。
取决于预期用途,颜料以本领域中通常的量使用,例如以基于整个配制剂的1-60wt%,或10-30wt%的量使用。
组合物也可包括不同类型的有机染料。例子是偶氮染料,甲川型染料,蒽醌染料或金属配合物染料。通常的浓度例如是基于整个配制剂的0.1-20%,尤其是1-5%。
添加剂的选择根据应用领域和这一领域所需要的性能来进行。如上所述的添加剂是本领域中常用的并且因此是按照在各种应用中常用的量添加。
在某些情况下可能有利的是使用光潜碱化合物(a)中的两种或多种的混合物。
除包含组分(a)、(b)和(c)的上述碱可催化(可固化)配制剂之外,该组合物同样还可包括其它基料。其它烯属不饱和化合物的添加例如是可能的。
因此,包含组分(a)、(b)和(c)的组合物例如与自由基可固化的组分(不饱和化合物)和任选的自由基引发剂例如热引发剂或光引发剂掺混使用。
不饱和化合物例如包括一个或多个烯属双键。它们具有低分子量(单体的)或高分子量(低聚的)。具有双键的单体的例子是烷基或羟烷基的丙烯酸酯或甲基丙烯酸酯如甲基、乙基、丁基、2-乙基己基或2-羟乙基的丙烯酸酯,丙烯酸异冰片基酯,甲基丙烯酸甲基酯或甲基丙烯酸乙酯。聚硅氧烷丙烯酸酯也是所考虑的。其它例子是丙烯腈,丙烯酰胺,甲基丙烯酰胺,N-取代的(甲基)丙烯酰胺,乙烯基酯如乙酸乙烯酯,乙烯基醚如异丁基乙烯醚,苯乙烯,烷基-和卤苯乙烯,N-乙烯基吡咯烷酮,氯乙烯或偏二氯乙烯。
具有两个或多个双键的单体的例子是乙二醇,丙二醇,新戊二醇,己二醇或双酚A的二丙烯酸酯,4,4’-双(2-丙烯酰氧基乙氧基)二苯基丙烷,三羟甲基丙烷三丙烯酸酯,季戊四醇三丙烯酸酯或四丙烯酸酯,丙烯酸乙烯基酯,二乙烯基苯,琥珀酸二乙烯基酯,邻苯二甲酸二烯丙酯,磷酸三烯丙基酯,异氰脲酸三烯丙基酯或异氰脲酸三(2-丙烯酰基乙基)酯。
较高分子量的多不饱和化合物(低聚物)的例子是丙烯酸化环氧树脂,丙烯酸化聚酯或含有乙烯基醚基团或环氧基的聚酯,聚氨酯和聚醚。不饱和低聚物的其它例子是主要从马来酸、邻苯二甲酸和一种或多种二醇制备的并具约500-3000的分子量的不饱和聚酯树脂。另外还有可能使用乙烯基醚单体和低聚物,以及具有聚酯、聚氨酯、聚醚、聚乙烯醚和环氧树脂主链的马来酸酯终端的低聚物。尤其,已描述在WO 90/01512中的乙烯基醚官能化低聚物和聚合物的结合物是非常合适的。然而,也合适的是乙烯基醚和马来酸官能化单体的共聚物。这一类型的不饱和低聚物也被称作预聚物。
特别合适的例子是烯属不饱和羧酸和多元醇或聚环氧化物的酯,和在链中或在侧基中具有烯属不饱和基团的聚合物,如不饱和聚酯、聚酰胺和聚氨酯和它们的共聚物,醇酸树脂,聚丁二烯和丁二烯共聚物,聚异戊二烯和异戌二烯共聚物,在侧链中具有(甲基)丙烯酸基团的聚合物和共聚物,和一种或多种此类聚合物的混合物。
如果,另外,使用此类自由基可固化的单体、低聚物/聚合物,则合适的是添加可离解成自由基的引发剂。合适的是热引发剂或,当组合物是光可固化的组合物时,光引发剂。
因此,固化过程能够通过添加在热状态下形成自由基的组分来协助,例如偶氮化合物如2,2’-偶氮双(4-甲氧基-2,4-二甲基戊腈),三氮烯,重氮硫化物,五氮杂二烯烃(pentazadiene)或过氧化合物,例如氢过氧化物或过碳酸酯,例如叔丁基过氧化氢,按照例如在EP 245639中所述。
合适的光引发剂是本领域中已知的并且在工业上生产。例子是二苯甲酮,二苯甲酮衍生物类,如2,4,6-三甲基二苯甲酮和4-甲基二苯甲酮,乙酰苯,乙酰苯衍生物类,例如α-羟基环烷基苯基酮,尤其α-羟基环己基苯基酮,2-羟基-2-甲基-1-苯基丙酮,1-[4-(2-羟基乙氧基)-苯基]-2-羟基-2-甲基-1-丙烷-1-酮,2-羟基-1-{4-[4-(2-羟基-2-甲基-丙酰基)-苄基]-苯基}-2-甲基-丙烷-1-酮,2-羟基-1-{4-[4-(2-羟基-2-甲基-丙酰基)-苯氧基]-苯基}-2-甲基-丙烷-1-酮,二烷氧基乙酰苯类,例如2,2-二甲氧基-1,2-二苯基乙烷-1-酮,α-氨基苯乙酮类,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,2-二甲基氨基-2-(4-甲基-苄基)-1-(4-吗啉-4-基-苯基)-丁-1-酮,2-苄基-1-(3,4-二甲氧基-苯基)-2-二甲基氨基-丁-1-酮,4-芳酰基-1,3-二氧戊环,苯偶姻烷基醚和苯偶酰酮缩醇类,如苯偶酰二甲基酮缩醇,苯基乙醛酸酯类和它们的衍生物,二聚苯基乙醛酸酯类,例如氧代-苯基-乙酸2-[2-(2-氧代-2-苯基-乙酰氧基)-乙氧基]-乙基酯;单酰基膦氧化物类,如(2,4,6-三甲基苯甲酰基)苯膦氧化物,双酰基膦氧化物,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,三酰基膦氧化物类,肟酯类,例如1,2-辛二酮1-[4-(苯硫基)苯基]-2-(O-苯甲酰基肟);乙酮1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]-1-(O-乙酰基肟),9H-噻吨-2-缩醛9-氧代-2-(O-乙酰基肟),乙酮1-[9-乙基-6-(4-吗啉代苯甲酰基)-9H-咔唑-3-基]-1-(O-乙酰基肟);二茂铁化合物或二茂钛,如二环戊二烯基双(2,6-二氟-3-吡咯并苯基)钛。
例子已在EP 284561指定。其中固化/交联通过不同机理来进行的这一类型的聚合物体系也被称作混杂体系。
本发明的组合物还可以在它们之中添加非反应活性的基料,如果光可聚合的化合物是液体或粘性物质,则是特别理想的。非反应活性基料的量例如是整个固体含量的5-95wt%,优选10-90wt%和,尤其是40-90wt%。非反应活性基料的选择是根据应用领域和这一应用所需的性能来进行的,例如在含水和有机溶剂体系中的显影(development)的可能性,对基材的粘合性,和对氧气的敏感性。
合适基料的例子是具有约5000-2,000,000,优选10,000-1,000,000的分子量的聚合物。例子是:均聚和共聚的丙烯酸酯和甲基丙烯酸酯,例如甲基丙烯酸甲酯/丙烯酸乙酯/甲基丙烯酸的共聚物,聚(甲基丙烯酸烷基酯),聚(丙烯酸烷基酯);纤维素酯类和醚类,如乙酸纤维素,乙酸丁酸纤维素,甲基纤维素,乙基纤维素;聚乙烯醇缩丁醛,聚乙烯醇缩甲醛,环化橡胶,聚醚类如聚氧化乙烯,聚氧化丙烯,聚四氢呋喃;聚苯乙烯,聚碳酸酯,聚氨酯,氯化聚烯烃,聚氯乙烯,氯乙烯/偏二氯乙烯的共聚物,偏二氯乙烯与丙烯腈的共聚物,甲基丙烯酸甲酯和乙酸乙烯酯,聚乙酸乙烯酯,共聚(乙烯/乙酸乙烯),聚合物类如聚己内酰胺和聚(己二酰六亚甲基二胺)和聚酯类如聚(对苯二甲酸乙二醇酯)和聚(丁二酸己二醇酯)。
如果另外使用此类自由基可固化单体、低聚物/聚合物,则光可聚合的组合物可以包括各种添加剂。这些的例子是热(聚合)抑制剂,它用来防止过早的聚合反应,例子是氢醌,氢化奎宁衍生物,对-甲氧基苯酚,β-萘酚或空间位阻酚类,如2,6-二-叔丁基-对甲酚。为了提高在黑暗中贮存稳定性,有可能例如使用铜化合物,如铜的环烷酸盐、硬脂酸盐或辛酸盐,磷化合物,例如三苯基膦,三丁基膦,亚磷酸三乙基酯,亚磷酸三苯酯或亚磷酸三苄基酯,季铵化合物类,例如四甲铵氯化物或三甲基苄基铵氯化物,或羟胺衍生物类,例如N-二乙基羟基胺。为了在聚合过程中排除大气氧,有可能添加链烷烃或类似的蜡状物质,它们在聚合物中具有不足够的溶解度,在聚合反应的开始迁移至表面并形成透明的表面层,后者防止空气进入。还有可能施涂氧气不渗透性层。能够以少量添加的光稳定剂是UV吸收剂,例如属于羟苯基苯并***,羟苯基-二苯甲酮,草酰胺或羟苯基-s-三嗪型的那些。这些化合物能够在有或没有位阻胺(HALS)的情况下单独或以混合物使用。
此类UV吸收剂和光稳定剂的例子已公开在WO 04/074328Case22841,第12页,9行至第14页,23行,该公开物被引入供参考。
为了促进光聚合反应,有可能添加胺类,例如三乙醇胺,N-甲基二乙醇胺,对-二甲基氨基苯甲酸酯或米蚩酮。胺的活性能够通过二苯甲酮型的芳族酮的添加来增强。能够用作氧清除剂的胺类的例子是取代N,N-二烷基苯胺,如在EP 339841中所述。其它促进剂,助引发剂和自动氧化剂是硫醇,硫醚,二硫化物,膦盐,膦氧化物或膦类,已描述在例如EP 438123,GB 2180358和JP Kokai Hei 6-68309中。
此外还有可能将本领域中常用的链转移剂添加到根据本发明的组合物中。例子是硫醇类,胺类和苯并噻唑。
在一些情况下理想的是在暴露于光的过程中或之后进行加热。以这种方法有可能在很多情况下促进该交联反应。
本发明的组合物能够用于各种目的,例如作为印刷油墨,作为透明清漆,作为白漆,例如用于木材或金属,作为涂料,特别用于纸、木材、金属或塑料,作为粉末涂料,作为对建筑物和道路作标记的日光可固化外用涂料,用于摄影复制方法中,用于全息照相记录材料,用于影象记录方法或用于能够使用有机溶剂或含水碱性介质中显影的印刷版的生产,用于丝网印刷用的掩模的生产,作为补牙材料,作为粘合剂,其中包括压敏粘合剂在内,用于密封,作为层压树脂,作为蚀刻光刻胶或永久性光刻胶和作为电子电路的焊剂遮盖层,用于铸封用组分,用于模制品,用于由密封固化(在透明模具中的UV固化)或由立体平版印刷方法(按照在例如US 4575330中所述)所进行的三维制品的生产,用于复合材料(例如苯乙烯聚酯,它可以含有玻璃纤维和/或其它纤维和其它助剂)和其它厚层组合物的制备,用于电子组件的涂布或包封或作为光学纤维的涂料。
特别理想的是本发明组合物用于制备装饰涂料,如在全部类型的基材(例如建筑物、围墙、刨花板)上的外用涂料,和用作石头、混凝土或金属上的涂料,用于车辆例如小汽车、铁路或飞机的涂料,的用途。该组合物可同样地用于汽车OEM涂饰和汽车再涂饰,以及用于汽车车身的涂饰,小汽车的塑料零件和装在车身上的汽车部件。本发明的引发剂能够在多涂层体系中用于面漆层,底涂层或透明涂层。它们在含颜料的外涂层中的使用也是可能的。
在表面涂层中,通常使用由预聚物与也含有单不饱和单体的多不饱和单体组成的混合物。这里预聚物主要负责涂膜的性能,并且通过改变它可让本领域中技术人员影响固化涂膜的性能。多不饱和的单体用作交联剂,它致使涂膜变得不可溶。单不饱和的单体用作活性稀释剂,因此无需使用溶剂就可降低粘度。
本发明的光可固化的组合物例如适合作为全部类型的基材的涂料,该基材的例子是木材,纺织品,纸,陶瓷,玻璃,塑料如聚酯,聚对苯二甲酸乙二醇酯,聚烯烃或乙酸纤维素,特别呈现膜的形式,以及金属如Al,Cu,Ni,Fe,Zn,Mg或Co和GaAs,Si或SiO2,在这些基材之上希望施涂保护涂层或,通过成像方式曝光的途径,施加图像。
该基材能够通过施涂液体组合物,溶液或悬浮液到基材上来涂布。溶剂和浓度的选择主要取决于组合物的类型和涂布方法。溶剂应该是惰性的:换句话说,它不应该与组分之间发生任何化学反应并且应该能够在涂布操作之后在干燥过程中再次被除去。合适溶剂的例子是酮,醚和酯,如甲基乙基酮,异丁基甲基酮,环戊酮,环己酮,N-甲基吡咯烷酮,二噁烷,四氢呋喃,2-甲氧基乙醇,2-乙氧基乙醇,1-甲氧基-2-丙醇,1,2-二甲氧基乙烷,乙酸乙酯,乙酸正丁酯和3-乙氧基丙酸乙基酯。
通过使用已知的涂布方法,溶液被均匀地施涂到基材上,例如通过旋涂法,浸渍涂布法,刮刀涂布法,幕涂,刷涂,喷雾涂布-尤其是静电喷涂-和逆辊涂布和通过电泳淀积法。还有可能将光敏层施涂于临时、柔性的载体上,然后经由层合法利用层转移来涂布最终的基材,例如镀铜的电路板。
施涂的量(层厚度)和基材的性质(层载体)是所希望的应用领域决定的。层厚度的范围一般包括约0.1μm到大于100μm。
根据本发明的组合物也适合用于UV固化型粘合剂。该粘合剂能够是热熔性粘合剂以及水性或溶剂型粘合剂。尤其合适的是压敏粘合剂(PSA),例如UV可固化的热熔压敏粘合剂。所述粘合剂例如包括至少一种橡胶组分,至少一种树脂组分(作为增粘剂)和至少一种油组分,例如按照重量比30:50:20。合适增粘剂是天然或合成树脂。所属技术领域的专业人员知道合适的相应化合物以及合适的油组分或橡胶。
含有封闭异氰酸酯的预聚合的粘合剂能够例如在高温下加工并且在热熔粘过程之后被涂布到基材上,然后通过牵涉到封闭异氰酸酯的附加固化步骤实现完全固化,这一完全固化通过光潜催化剂的光活化来实现。
热熔粘合剂令人感兴趣的作为压敏粘合剂并适合于代替溶剂基础组合物(base compositions)的使用,其从环境考虑是不希望的。为了实现高流动性粘度,热熔挤出过程需要高的使用温度。包括封闭异氰酸酯的本发明的组合物适合在热熔涂料的制备中用作交联剂,其中交联剂与(甲基)丙烯酸酯PSA的官能化共聚用单体进行化学反应。在涂布操作之后,该PSA首先进行热交联,或进行双交联机理,该PSA随后用UV光交联。取决于UV光引发剂,UV交联辐射利用在200-400nm的波长范围内的短波紫外线辐射来进行。此类体系和方法例如已描述在US2006/0052472中,它的公开内容被引入这里供参考。
根据本发明的组合物也适合用于电沉积漆或底漆:电沉积漆一般由作为基础树脂的含有羟基的树脂和作为固化剂的用封闭剂封闭的多异氰酸酯化合物组成。电沉积步骤能够例如通过将包含用于电沉积漆的树脂组合物的电沉积浴的温度通常调节至15-35℃在50-400kV的负载电压条件下进行,该组合物已经用去离子水等稀释至约5-40wt%的固体含量浓度并且体系的pH调节在4-9范围内。
通过使用用于电沉积漆的树脂组合物可形成的电沉积涂膜的膜厚度没有特别限制。优选它一般在10-40μm范围内,基于固化膜厚度。通过涉及到封闭异氰酸酯和氢供体的附加固化步骤来实现完全固化,该完全固化是通过光潜催化剂的光催化作用来实现。取决于UV光引发剂,UV交联辐射利用在200-400nm的波长范围内的短波紫外线辐射来进行。还有可能同时或之后让电沉积涂层进行热固化步骤。此类涂的例子已描述在US 2005/0131193和US 2001/0053828,两者被引入这里供参考。
本发明的组合物也用于“粉末涂料组合物”或“粉末涂料”,属于热固化型或辐射可固化的固化型。至于“粉末涂料组合物”或“粉末涂料”是指在“Ullmann′s Encyclopedia of Industrial Chemistry,5th,完全修改版(Completely Revised Edition),Vol.A18”,438至444页(1991)3.4节中所述的定义。它是通过热塑性或可烘烤、可交联的聚合物形成的,它以粉末形式被施涂于(主要为金属)基材上。粉末与所要涂布的工件接触的方式代表了各种涂布技术,如静电粉末喷雾,静电流化床熔结,固定层烧结,流化床熔结,旋转熔结或离心熔结。
粉末涂料组合物的优选的有机成膜基料是烘漆体系,后者基于例如环氧树脂,聚酯-羟基烷基酰胺,聚酯-甘脲,聚环氧-聚酯树脂,聚酯-三缩水甘油基异氰脲酸酯,羟基官能化聚酯-封闭多异氰酸酯,羟基官能化聚酯-脲二酮,有硬化剂的丙烯酸酯树脂,或此类树脂的混合物。
辐射可固化粉末涂料例如基于固体树脂和含有反应活性双键的单体,例如马来酸酯,乙烯基醚,丙烯酸酯,丙烯酰胺和它们的混合物。自由基方式UV可固化的粉末涂料-与本发明的组合物掺混-能够例如通过将不饱和聚酯树脂与固体丙烯酰胺(例如甲基丙烯酰胺基乙醇酸甲基酯),丙烯酸酯,甲基丙烯酸酯或乙烯基醚和自由基光引发剂混合来配制,此类配制剂例如已描述在论文“Radiation Curing of Powder Coating”,Conference Proceedings,Radtech Europe 1993,M.Wittig和Th.Gohmann。粉末涂料也可包括描述在例如DE 4228514中和在EP 636669中的基料。
粉末涂料可以另外包括白色或有色颜料。例如,优选金红石型二氧化钛能够以最高达50wt%的浓度使用,为的是得到良好遮盖力的固化粉末涂层。该程序通常包括将粉末的静电喷雾或摩擦静电喷雾到基材例如金属或木材上,加热熔化粉末,和在形成光滑膜之后,涂层用紫外线和/或可见光进行辐射固化。
本发明的组合物另外可用于印刷油墨的制备。印刷油墨一般为所属技术领域的专业人员所已知,在现有技术中已广泛使用并且已描述在文献中。它们例如是含有颜料的印刷油墨和用染料着色的印刷油墨。
印刷油墨例如是包括着色剂(颜料或染料),连接料以及任选的溶剂和/或任选的水和添加剂的液体或浆料形式分散体。在液体印刷油墨中,该连接料和如果可适用的话添加剂一般被溶于溶剂中。对于液体印刷油墨,在布鲁克费尔德(Brookfield)粘度计中的常规粘度例如是20-5000mpa·s,例如20-1000mpa·s。对于浆料形式印刷油墨,该数值范围例如是1-100Pa·s,优选5-50Pa·s。所属技术领域的专业人员熟悉印刷油墨的成分和组成。
用于现有技术常用的印刷油墨配制剂中的印刷油墨用合适颜料一般是已知的并且广泛地描述过。印刷油墨包括,有利地,例如0.01-40wt%,优选1-25wt%,尤其5-10wt%的浓度的颜料,以印刷油墨的总重量为基础。
该印刷油墨能够例如用于在材料上的凹版印刷,橡胶版轮转印刷,丝网印刷,胶版印刷,平版印刷或连续或滴加式喷墨印刷,该材料已根据本发明的方法通过使用一般已知(例如在出版、包装或运输中,在后勤中,在广告中,在保密印刷中或在办公设备的领域中)的配制剂进行预处理。
合适的印刷油墨可以是溶剂型印刷油墨和水性型印刷油墨。
合适的是例如以水性丙烯酸酯为基础的印刷油墨。此类油墨被理解为包括可通过含有基团-(C=CH2)-(C=O)-O-或-(C=CH2)-(C=O)-N-的至少一种单体的聚合反应获得的并且溶于水或含水的有机溶剂中的聚合物或共聚物。合适的有机溶剂是所属技术领域的专业人员常用的水混溶性溶剂,例如醇类,如甲醇、乙醇和丙醇、丁醇和戊醇的异构体,乙二醇和它的醚,如乙二醇甲基醚和乙二醇乙基醚,和酮类,如丙酮,乙基甲基酮或环状,例如异丙醇。水和醇是优选的。
合适的印刷油墨包括例如作为连接料,主要地丙烯酸酯聚合物或共聚物以及溶剂,例如选自水,C1-C5醇,乙二醇,2-(C1-C5烷氧基)-乙醇,丙酮,乙基甲基酮和它们的任何混合物。
除连接料之外,该印刷油墨还可包括常用浓度的为所属技术领域的专业人员所已知的常规添加剂。
对于凹版印刷或橡胶版轮转印刷,印刷墨水通常通过印刷油墨浓缩物的稀释来制备并且因此根据本身已知的方法来使用。
该印刷油墨例如还可包括氧化干燥性的醇酸树脂体系。
该印刷油墨按照现有技术中常用的已知方式进行干燥,任选对涂层加热。
合适的水性印刷油墨组合物包括例如颜料或颜料的结合物,分散剂和连接料。
所述分散剂包括例如通常的分散剂,如以一种或多种芳基磺酸/甲醛缩合产物为基础或以一种或多种水溶性烷氧基化酚类、非离子分散剂或聚合酸为基础的水溶性分散剂。
该芳基磺酸/甲醛缩合产物例如可通过芳族化合物如萘本身或含有萘的混合物的磺化以及所得芳基磺酸与甲醛的后续缩合来获得。此类分散剂是已知并且已描述在例如US 5186846和DE 19727767中。合适的烷氧基化酚类同样是已知的并且已描述在例如US 4218218和DE 19727767中。合适的非离子的分散剂是例如烯化氧加合物,乙烯基吡咯烷酮、乙酸乙烯酯或乙烯醇的聚合产物以及乙烯基吡咯烷酮与乙酸乙烯酯和/或乙烯醇的二元共聚物或三元共聚物。
还有可能例如使用同时用作分散剂和连接料的聚合酸类。
可提及的合适连接料组分的例子包括含丙烯酸酯基团、乙烯基团的和/或环氧基的单体、预聚物和聚合物和它们的混合物。其它例子是蜜胺丙烯酸酯和聚硅氧烷丙烯酸酯。该丙烯酸酯化合物也可以是非离子改性(例如提供有氨基)或离子改性(例如提供有酸基或铵基团)并以含水的分散体或乳液形式使用(例如EP 704469,EP 12339)。此外,为了获得所希望的粘度该无溶剂的丙烯酸酯聚合物能够与所谓的活性稀释剂(例如含乙烯基团的单体)混合。其它合适的连接料组分是含环氧基团的化合物。
该印刷油墨组合物还可包括,作为附加组分,例如具有持水作用的试剂(湿润剂),例如多元醇,聚(亚烷基)二醇,它使组合物尤其适合于喷墨印刷。
可以理解的是,印刷油墨可以包括其它助剂,如尤其是(水性)喷墨印刷油墨常用和在印刷和涂料工业中常用的那些,例如防腐剂(如戊二醛和/或四羟甲基乙炔脲,抗氧化剂,脱气剂/消泡剂,粘度调节剂,流动改进剂,防沉剂,光泽改进剂,润滑剂,粘合促进剂,抗结皮剂,消光剂,乳化剂,稳定剂,疏水剂,光稳定剂,处置(handle)改进剂和抗静电剂。当此类试剂存在于组合物中时,它们的总量一般≤1wt%,以制剂的重量为基础。
合适的印刷油墨包括例如包含染料的那些(染料总含量为例如1-35wt%,以油墨的总重量为基础)。
此类印刷油墨可以包括有机溶剂,例如水混溶性有机溶剂,例如C1-C4醇类,酰胺类,酮类或酮醇类,醚类,含氮的杂环化合物,聚(亚烷基)二醇,C2-C6亚烷基二醇和硫甘醇,其它多元醇,例如甘油和多元醇的C1-C4烷基醚,通常含量为印刷油墨总重量的2-30wt%.
该印刷油墨还可例如包括增溶剂,例如α-己内酰胺。
特别为了调节粘度的目的,该印刷油墨可以包括天然或合成的增稠剂。增稠剂的离子包括商购的海藻酸盐增稠剂,淀粉醚或角豆荚果粉醚。印刷油墨包括例如0.01-2wt%的此类增稠剂,以印刷油墨的总重量为基础。
印刷油墨还有可能包含例如0.1-3wt%的缓冲物质,例如硼砂,硼酸盐,磷酸盐,聚磷酸盐或柠檬酸盐,为的是建立例如4-9,尤其是5-8.5的pH值。
作为附加添加剂,此类印刷油墨可以包括表面活性剂或湿润剂。可考虑的表面活性剂包括商购的阴离子和非离子型表面活性剂。所考虑的湿润剂包括例如脲,或乳酸钠(有利地以50-60%水溶液形式)与甘油和/或丙二醇的混合物,它在印刷油墨中的含量是例如0.1-30wt%,尤其是2-30wt%。
此外,该印刷油墨还可包括通常的添加剂,例如消泡剂剂或尤其抑制真菌和/或细菌生长的物质。此类添加剂的通常用量是印刷油墨总重量的0.01-1wt%。
印刷油墨也可以通常的方式通过将各组分一起混合在例如所需量的水中来制备。
正如早已提到的那样,根据使用的性质,需要该印刷油墨的例如粘度或其它物理性能因此被调节,尤其影响印刷油墨对所述基材的亲合性的那些性能。
该印刷油墨也合适用于例如某些类型的记录***中,在该类型中印刷油墨以液滴形式从小孔中挤出,该液滴被引导至所要形成图像的基材。合适的基材是例如根据本发明的方法预处理的纺织纤维材料,纸张,塑料或铝箔。合适的记录***例如是商购的喷墨印刷机。
优选的是采用水性印刷油墨的印刷方法。
本发明的辐射敏感性组合物也能够以成图像的方式进行曝光。在这种情况下它们用作负性抗蚀剂。它们适合用于电子设备(电致抗蚀剂,抗蚀刻剂和阻焊剂),用于印刷版如胶版印刷版、苯胺印刷版和凸版或丝网印刷版的生产,用于压印模的生产,和能够用于化学打磨或在集成电路的生产中用作微抗蚀剂。在可能的层状载体中和在涂布基材的加工条件中有相应的宽范围变化。
术语“以成像方式”曝光同时涉及通过含有预定图案的光掩模例如滑动片(slide)的曝光方法,通过激光束进行曝光的方法,该激光束在计算机控制下移动(例如在涂布基材的表面之上)和因此产生图像,和用计算机控制的电子束的辐射方法。
在材料的以成像方式曝光之后和在显影之前,理想的是进行简单的热处理,其中仅仅曝光部分被热固化。使用的温度一般是50-150℃和优选80-130℃;热处理的持续时间一般是在0.25分钟和10分钟之间。
光固化的其它应用领域是金属涂层,例如金属板和罐、罐或瓶顶的表面涂层,和在(例如以PVC为基础的地板或墙面覆盖层(coverings)的)聚合物涂层上的光固化的应用领域。
纸张涂料的光固化的例子是标记,记录套筒(sleeves)或书封皮的无色清漆涂饰。
本发明组合物用于制备从复合材料组合物制造的成形制品的用途同样是所考虑的。该复合材料组合物由自支持基质材料(例如玻璃纤维织物),或例如植物纤维组成。[参见K.-P.Mieck,T.Reussmann inKunststoffe 85(1995),366-370],它用光固化型配制剂浸渍。从根据本发明的组合物生产的成形制品具有高的机械稳定性和耐机械作用性能。本发明的组合物还可以用于模塑、浸渍和涂料型组合物,如在例如EP007086中所述。此类组合物的例子是对固化活性和耐泛黄性能有严格要求的精细涂料树脂,或纤维增强的模制品,如平面或纵向或横向波纹的光散射板。
该新型组合物对辐射的敏感性一般从约190nm延伸贯穿UV区域并进入到红外区(约20,000nm,尤其1200nm),尤其190nm-650nm,因此覆盖了非常宽的范围。合适的辐射例如存在于太阳光或来自人造光源的光线中。因此,许多的非常不同类型的光源都可以使用。点光源和阵列光源(“灯地毯”)是合适的。例子是碳弧灯,氙弧灯,中压-,超高-,高压-和低压-水银灯,可能有金属卤化物掺杂(金属-卤素灯),微波刺激的金属蒸气灯,受激准分子灯,超光化性日光灯,荧光灯,氩气白炽灯,电子手电筒,照相用散光灯排,电子束和X射线。在灯与根据本发明所要曝光的基材之间的距离可以根据预期应用和灯的类型和输出额来改变,并且可以是例如2cm-150cm。激光源,例如准分子激光器,如在248nm下曝光的氪F激光器,也是合适。在可见光谱区中的激光也可以使用。
另外地,该光化辐射由发光二极管(LED)或有机发光二极管(OLED)提供,例如UV光发射二极管(UV-LED)。该LED允许辐射源的瞬时接通和关闭。此外,UV-LED一般具有窄的波长分布并提供了设定峰值波长的可能性和还提供了电能至紫外线辐射的有效转换。
取决于所使用的光源,在很多情况下理想的是使用如上所述的增感剂,它的吸收光谱尽可能接近地与辐射源的发射光谱相符。
本发明因此还提供了使封闭异氰酸酯(b)和H-给体(c)交联的方法,这通过将这些组分与在权利要求2中定义的式I的光潜碱催化剂(a)混合和用200-650nm的波长范围的光辐射该组合物来进行。
本发明的主题另外是如上所述的组合物在粘合剂,涂料,密封剂,铸封组分,印刷油墨,模塑料,或光结构化层的制备中的用途。
以及如上所述的制备粘合剂,涂料,密封剂,铸封组分,印刷油墨,模塑料,或光结构化层的方法。
本发明的另一个实施方案是在至少一个表面上涂布了如上所述的组合物的涂布基材;以及如上所述的聚合或交联的组合物。
下面的实施例用于更详细地举例说明本发明,但不限定权利要求的范围。份和百分数,在说明书的剩余部分中和在权利要求中,是按照重量计,除非另有说明。当在实施例中涉及到具有三个以上碳原子的烷基且没有具体异构体的任何提及时,在各情况下该烷基指正异构体。
封闭异氰酸酯是根据报道在WO 03/004545(Bayer AG)中的程序制备的。
产物1的制备
在装有机械搅拌器、温度计、回流冷凝器和滴液漏斗的250ml三颈烧瓶中,将42.7g(0.3mol)2-氧代环戊烷甲酸甲酯(Fluka 29785)溶于20g乙酸丁酯中。将1g的2-乙基己酸锌(在矿物油中80%,锌含量17-19%)作为催化剂添加到溶液中。随后在快速搅拌下经过45分钟的时间将58.5g(0.3val异氰酸酯)的三异氰酸酯Desmodur N 3300(Bayer AG)在81g乙酸丁酯中的溶液滴加到这一溶液中。随着轻微的气体逸出,反应混合物的温度慢慢地从室温升高至34℃。当添加完成时,温度提高至50℃,并将浅黄色溶液在这一温度下保持五小时。在这一段时间之后小样品的分析显示了异氰酸酯的完全反应(在IR谱中在2273cm-1的异氰酸酯键的消失)。反应混合物被冷却到室温并作为封闭异氰酸酯在乙酸丁酯中的约50wt%溶液来使用。
实施例1:
通过混合下列组分来制备UV可固化的配制剂:
0.4wt%作为增感剂的异丙基噻吨酮;DAROCUR ITX,由CibaSpecialty Chemicals提供
5.2wt%带有羟基的支链聚酯;DESMOPHEN 1100,由Bayer AG提供
2.0wt%作为溶剂的乙酸丁酯;由Al drich提供
7.7wt%产物1,如以上所述方法制备。
该配制剂被施涂到BaF2晶体上并曝光于UV光(在两个Hg汞灯AETEK International(80W/cm)下以5m/min的速度移动的传送带上通过1次)。在120℃下加热20分钟之前和之后测量IR谱。
重复实验但没有UV曝光。
通过监测在1525cm-1处的CNH双峰来跟踪反应程度。1534cm-1CNH归属于封闭异氰酸酯,1546cm-1归属于在解封闭之后在羟基和异氰酸酯之间的反应所得到的CNH键。两个峰的高度比因此允许定量该反应程度。这一比值越高,反应程度越高。结果报道在表1中。从这些数据清楚地看出,与没有UV曝光所获得的结果相比,UV曝光增加了尿烷键的量。
进一步测定的是配制剂的稳定性。结果收集在表2中。
表1:表征反应程度的尿烷和封闭NCO峰的比值
处理 | 比值尿烷/封闭NCO |
用UV | 0.79 |
用UV+20min 120℃ | 0.89 |
没有UV | 0.67 |
没有UV+20min 120℃ | 0.72 |
表2:有和没有催化剂及有光潜催化剂的含有封闭异氰酸酯和OH-组分的配制剂的贮存期
处理 | 贮存期 |
没有催化剂 | 至少14天 |
有1,5-二氮杂双环[4.3.0]酮-5-烯(DBN) | 1小时 |
有光潜碱 | 至少14天 |
Claims (16)
1.一种组合物,它包括
(a)光潜碱;
(b)封闭异氰酸酯或封闭异硫氰酸酯和
(c)氢给体化合物。
2.根据权利要求1的组合物,其中光潜碱是式II的化合物,
Z-A (II),
其中
Z是对光不稳的基团;和
A是碱前体基团,以共价键键接于Z。
3.根据权利要求1或2中任何一项的组合物,其中光潜碱具有式(I)
其中
R1是芳族或杂芳族基团,它能够吸收在200-650nm的波长范围内的光并且它是未被取代的或被一个或多个C1-C18-烷基,C2-C18-链烯基,C2-C18-炔基,C1-C18-卤代烷基,NR8R9,CN,OR10,SR10,COR11,COOR12,卤素或以下基团所取代:
或R1是
R2和R3彼此独立地是氢,C1-C18-烷基,C1-C18-链烯基,C3-C18-炔基或苯基,该苯基是未被取代的或被一个或多个C1-C18-烷基,CN,OR12,SR12,卤素,或C1-C18-卤代烷基取代;
R5是C1-C18-烷基或NR10R11;
R4,R6,R7,R8和R9彼此独立地是氢或C1-C18-烷基;或
R4和R6一起形成C2-C12-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;或
R5和R7,与R4和R6独立地,一起形成C2-C12亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;或,如果R5是NR10R11,R7和R11一起形成C2-C12-亚烷基桥基,该桥基是未被取代的或被一个或多个C1-C4-烷基取代;
R10,R11和R12彼此独立地是氢或C1-C18烷基;
R13是芳族或杂芳族基团,它能够吸收在200-650nm波长范围内的光并且它是未被取代的或被一个或多个取代基C1-C18-烷基,C2-C18-链烯基,C2-C18-炔基,C1-C18-卤代烷基,NR8R9,CN,OR10,SR10,COR11,COOR12或卤素取代;
R14是氢或C1-C18-烷基;
R15是氢,C1-C18-烷基或苯基,该苯基是未被取代的或被一个或多个C1-C18-烷基,乙烯基,C3-C18-链烯基,C3-C18-炔基,C1-C18-卤代烷基,苯基,NR8R9,CN,OR10,SR10,COR11,COOR12或卤素取代。
5.根据权利要求1的组合物,其中封闭异氰酸酯选自脂族或芳族多异氰酸酯,二异氰酸酯,三异氰酸酯和四异氰酸酯。
6.根据权利要求5的组合物,其中异氰酸酯的封闭剂选自醇,酚,胺,酰亚胺,酰胺,胍,脒,***,吡唑,活性亚甲基化合物,酮肟,肟,甲酸酯,内酰胺,咪唑,CH-酸性环酮,和硫醇。
7.根据权利要求5的组合物,其中封闭剂是环戊酮-2-羧基甲基酯,环戊酮-2-羧基乙基酯,环戊酮-2-甲腈,环己酮-2-羧基甲基酯,环己酮-2-羧基乙基酯,或环戊酮-2-羰基甲烷。
8.根据权利要求1的组合物,其中氢供体组分(c)是选自醇,多元醇,酚,硼酸,羧酸,磺酸,胺,酰胺,内酰胺,脲,尿烷,脲基甲酸酯,缩二脲,酰基脲,硫脲,腙,肟,脒,羟胺,腙,异羟肟酸,硝胺,重氮氨基化合物,磺酰胺,硫醇,多硫醇,苯硫酚,硫代酸,卤素酸和含环氧基的化合物的至少一种化合物。
9.根据权利要求1的组合物,除包含组分(a),(b)和(c)之外,还包括选自二苯甲酮和它的衍生物,噻吨酮和它的衍生物,蒽醌和它的衍生物,香豆素和它的衍生物,噁嗪染料,吖啶染料,吩嗪染料和若丹明染料的化合物(d)。
10.根据权利要求1的组合物,其中组分(a)是以基于总组合物的0.01-20wt%,尤其0.01-10wt%的量存在。
11.在权利要求2中定义的式II的化合物或在权利要求3中定义的式I的化合物作为用于固化包含(b)封闭异氰酸酯和H-给体(c)的组合物的光潜碱催化剂(a)的用途。
12.使封闭异氰酸酯(b)和H-给体(c)交联的方法,这通过将所述组分与在权利要求2中定义的式II的光潜碱催化剂(a)或在权利要求3中定义的式I的化合物混合和用200-650nm波长范围的光辐射该组合物来进行。
13.根据权利要求1的组合物用于制备粘合剂,涂料,密封剂,铸封组分,印刷油墨,模塑料,或光结构化层的用途。
14.根据权利要求12的方法,用于制备粘合剂,涂料,密封剂,铸封组分,印刷油墨,模塑料,或光结构化层。
15.在至少一个表面上涂有根据权利要求1的组合物的涂布基材。
16.根据权利要求1的聚合或交联的组合物。
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PCT/EP2007/059865 WO2008037635A1 (en) | 2006-09-29 | 2007-09-19 | Photolatent bases for systems based on blocked isocyanates |
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- 2007-09-19 RU RU2009115962/04A patent/RU2009115962A/ru not_active Application Discontinuation
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RU2009115962A (ru) | 2010-11-10 |
JP2010505013A (ja) | 2010-02-18 |
KR20090077936A (ko) | 2009-07-16 |
BRPI0717655A2 (pt) | 2014-04-29 |
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