CN100575384C - 用于低温固化的促进剂体系 - Google Patents
用于低温固化的促进剂体系 Download PDFInfo
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- CN100575384C CN100575384C CN200480010048A CN200480010048A CN100575384C CN 100575384 C CN100575384 C CN 100575384C CN 200480010048 A CN200480010048 A CN 200480010048A CN 200480010048 A CN200480010048 A CN 200480010048A CN 100575384 C CN100575384 C CN 100575384C
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- alkyl
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- group replaces
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- 238000013035 low temperature curing Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 29
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 beta naphthal compound Chemical class 0.000 claims abstract description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003822 epoxy resin Substances 0.000 claims abstract description 14
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 14
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 238000005266 casting Methods 0.000 claims abstract description 4
- 238000000748 compression moulding Methods 0.000 claims abstract description 4
- 239000000843 powder Substances 0.000 claims abstract description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 3
- 238000005538 encapsulation Methods 0.000 claims abstract description 3
- 238000002347 injection Methods 0.000 claims abstract 2
- 239000007924 injection Substances 0.000 claims abstract 2
- 239000004593 Epoxy Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical group 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 3
- 238000005554 pickling Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 2
- 238000007598 dipping method Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000003860 storage Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 150000004780 naphthols Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000004693 imidazolium salts Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000009756 wet lay-up Methods 0.000 description 3
- UZUIHIHIXOLGDL-UHFFFAOYSA-N 1-methylnaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(C)=C(C=O)C=CC2=C1 UZUIHIHIXOLGDL-UHFFFAOYSA-N 0.000 description 2
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- IYDJTTMEODZPPB-UHFFFAOYSA-N 3-chloro-2,6-diethyl-4-methylaniline Chemical compound CCC1=CC(C)=C(Cl)C(CC)=C1N IYDJTTMEODZPPB-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 206010009866 Cold sweat Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 230000002650 habitual effect Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000008442 polyphenolic compounds Polymers 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- OIXUMNZGNCAOKY-UHFFFAOYSA-N 2,6-diethyl-4-methylaniline Chemical compound CCC1=CC(C)=CC(CC)=C1N OIXUMNZGNCAOKY-UHFFFAOYSA-N 0.000 description 1
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- TWFDUASEWSCMRO-UHFFFAOYSA-N 2-[(2-propylphenoxy)methyl]oxirane Chemical compound CCCC1=CC=CC=C1OCC1OC1 TWFDUASEWSCMRO-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- MHXYCLFSHMBXSD-UHFFFAOYSA-N 3-methyl-4-phenylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=CC=C1 MHXYCLFSHMBXSD-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
- OZUBMBIDHPBIDL-UHFFFAOYSA-N 4-Propylcyclohexylamine Chemical compound CCCC1CCC(N)CC1 OZUBMBIDHPBIDL-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- BRUPWFGTGIGWFT-UHFFFAOYSA-N 4-methyl-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC(C)=CC(C(C)C)=C1N BRUPWFGTGIGWFT-UHFFFAOYSA-N 0.000 description 1
- YVPZFPKENDZQEJ-UHFFFAOYSA-N 4-propylcyclohexan-1-ol Chemical compound CCCC1CCC(O)CC1 YVPZFPKENDZQEJ-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- AJBXRBRVQMZREG-UHFFFAOYSA-N OC(CC)(C1=CC=CC=C1)O.OC1=CC=C(C=C1)CCC Chemical compound OC(CC)(C1=CC=CC=C1)O.OC1=CC=C(C=C1)CCC AJBXRBRVQMZREG-UHFFFAOYSA-N 0.000 description 1
- 229920001079 Thiokol (polymer) Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- NICOYOFWFUEZOI-UHFFFAOYSA-N aniline;methane Chemical compound C.NC1=CC=CC=C1 NICOYOFWFUEZOI-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- AWMNXQXKGOSXDN-UHFFFAOYSA-N ethylideneurea Chemical compound CC=NC(N)=O AWMNXQXKGOSXDN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 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
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
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Abstract
包含以下组分的组合物：组分A)一种通式(I)的1-咪唑甲基-取代的2-萘酚化合物，其中R1，R2和R3相互独立地分别为H；C1-17烷基；C3-12环烷基，任选被C1-4烷基基团取代；C4-20环烷基-烷基，任选被C1-4烷基基团取代；C6-10芳基，任选被1-3个C1-4烷基基团取代；C7-15苯烷基，任选被1-3个C1-4烷基基团取代；C3-17烯基；C3-12炔基；或芳族或脂肪族C3-12酰基；R4，R5，R6，R7，R8，和R9相互独立地分别为H；C1-12烷基；C3-12环烷基，任选被C1-4烷基基团取代；C4-20环烷基-烷基，任选被C1-4烷基基团取代；C6-10芳基，任选被1-3个C1-4烷基基团取代；C7-15苯烷基，任选被1-3个C1-4烷基基团取代；C3-17烯基；C3-12炔基；C1-12烷氧基；或OH；以及组分B)一种室温下为液态的酚，组分A)与组分B)的重量比为10∶90-80∶20。在用作压塑材料，烧结粉末，封铸体系，浇铸树脂，或在浸渍方法或注射法生产具有优良层间剪切强度的半固化片和层压制品，或在生产元部件，特别是大表面积部件的可固化环氧树脂组合物中用作促进剂。
Description
本发明涉及新颖的曼尼希碱1-咪唑甲基-取代的2-萘酚化合物，还涉及其作为环氧树脂体系促进剂的用途，它可使层压制品有高的ILS值，特别适合湿铺叠法和其它浸渍法进行的浸渍。另外，所述促进剂还适用于200℃以下，特别是150-180℃范围内进行的烧结粉末，浇铸树脂和压塑材料的生产。
化合物1-咪唑甲基-2-萘酚和与环氧树脂有关的其它咪唑催化剂以及促进剂是已知的。
然而，常用的咪唑化合物如咪唑，1-甲基咪唑，2-甲基咪唑，2-乙基-4-甲基咪唑或2-苯基咪唑在用于预浸渍料坯配方时会产生室温下半固化片储存稳定性(简称放置时间)不足的问题。
过去人们尝试用有机酸或无机酸与咪唑化合物反应形成盐来降低其反应性以解决该问题，例如可参看US3,356,645和US5,001,212。尽管那些情况下半固化片的放置时间得到了改进，但仍不能满足很多应用的要求。
另一种提高半固化片放置时间的方法是使咪唑化合物与金属盐反应形成咪唑配合物，例如可参看US4,101,514和US4,487,914。一般来说，用这种方法来改进放置时间是以提高工艺温度为代价的。此外，存在于已固化环氧树脂体系中的金属配合物会导致介电值的劣化，同时也导致吸水性的增加。然而在很多应用中都要求吸水性基本不变，否则会造成玻璃化转变温度降低，从而导致浸渍化合物机械性能、电性能和热性能的大幅改变。
EP0 761 709描述了作为催化剂的1-咪唑甲基-取代的2-萘酚化合物，基本上避免了上述引证文献所描述的缺点。环氧树脂体系中所含的上述化合物是稳定的曼尼希碱，可以显著提高进整个体系在室温下的放置时间。含有该催化剂的配方在110℃到150℃的温度范围内可迅速固化。这种材料显示了良好的机械性能和相对高的玻璃化转变范围。含有这种催化剂的半固化片在室温下可毫无问题地储存16天并加工成层压制品。
生产价格看好的大表面积部件的既定方法包括湿铺叠法和其它的浸渍方法。基于成本的考虑，浸渍操作应在100℃以下进行。为了更容易操作，用该法制造的半成品(半固化片)在室温下应有相对长的储存稳定性，这就意味着半固化片必须在储存一段时间，侧如4天或更多天后，能够无故障地转变成层压制品。
当该法制备的层压制品用于能量发生装置，层压制品在使用过程中将发生转动运动并受到相当大的剪切力时，必须保证层压制品各层间的粘附力不能低于某一最低值。度量这种粘附力的一种方式称作层间剪切强度，也简称为ILS，可按照ASTM标准(ASTM D 2344-84)测定。因此实现该应用的目标是获得最大ILS值。
目前已发现在半固化片配方中加入1-(咪唑基-2-甲基)-2-萘酚确实可以显著提高半固化片在室温时的储存稳定性，但却不能获得很高的层间剪切强度值。不管是在60℃下固化4小时，还是在75℃下固化4小时或甚至8小时，或在140℃下固化30分钟，可获得的最大值约为22MPa。
现在令人吃惊地发现，由1-咪唑甲基-取代的2-萘酚化合物与酚组成的特定组合物用作环氧树脂体系的促进剂时具有优良的性能，特别是采用湿铺叠法和其它浸渍法生产时。特别是用该法可使ILS值最高增至50MPa。
据此，本发明首先提供了包含下述组分的组合物：组分A)一种通式(I)的1-咪唑甲基-取代的2-萘酚化合物
其中
R1，R2和R3相互独立地分别为H；C1-17烷基；
C3-12环烷基，任选被C1-4烷基基团取代；
C4-20环烷基-烷基，任选被C1-4烷基基团取代；
C6-10芳基，任选被1-3个C1-4烷基基团取代；
C7-15苯烷基，任选被1-3个C1-4烷基基团取代；
C3-17烯基；C3-12炔基；或芳族或脂肪族C3-12酰基；
R4，R5，R6，R7，R8，和R9相互独立地分别为H；C1-12烷基；
C3-12环烷基，任选被C1-4烷基基团取代；
C4-20环烷基-烷基，任选被C1-4烷基基团取代；
C6-10芳基，任选被1-3个C1-4烷基基团取代；
C7-15苯烷基，任选被1-3个C1-4烷基基团取代；
C3-17烯基；C3-12炔基；C1-12烷氧基；或OH；以及
组分B)一种室温下(RT＝15-35℃)为液态的酚，组分A)与组分B)的重量比(重量％表示)为10∶90-80∶20，优选为20∶80-70∶30，更优选为25∶75-50∶50。
作为组分A)，优选的通式(I)化合物为其中的基团R1，R2和R3相互独立地分别为H；C1-12烷基；苯基；或C7-15苯烷基，任选被1-3个C1-4烷基基团取代；特别优选的化合物为其中的R2和R3分别为H；同时R1为C1-12烷基；苯基；或C7-15苯烷基，任选被1-3个C1-4烷基基团取代。
作为组分A)，特别优选的通式(I)化合物为其中的基团R2到R9为氢原子，同时基团R1为C1-4烷基(甲基，乙基，正，异-丙基，正，异，叔-丁基)或苯基，由1-3C1-4烷基任选取代基。
作为组分B)，优选使用1，4-正-戊基-，-正-己基-，-正-庚基-，-正-辛基-，-正-壬基-和-正-癸基酚，特别优选使用O，O’-二烯丙基-双酚A。
为了避免由于酚的加入而导致固化配方的玻璃化转变范围的大幅下降，应当优选加入至少占组分A)和B)组成的组合物重量20％的萘酚衍生物部分。
制备本发明组合物时首先要制备1-咪唑甲基-取代的2-萘酚，例如可采用EP0 761 709所描述的方法来制备。优选先加入所选的酚(组分B)，然后再向酚中加入萘酚，在高温下如160℃，密切搅拌混合物4-6小时。根据所选的组分和混合比例不同，产物为发粘的高粘液体或固体。所获得的组合物的性质也可被描述为萘酚在酚中的固体溶液。向萘酚中加入至少约20重量％的酚时，被“改性”萘酚的特性就已发生重大改变，从而使此类组合物具有足以优选应用于半固化片的特性。已发现酚略微过量到显著过量(以重量％表示)的组合物都是特别优选的组合物。
正如开始时所提到的，本发明的组合物适合用作可固化环氧树脂体系的促进剂。
困此本发明进一步提供了可固化的环氧树脂组合物，包含：
a)环氧化物含量为0.1-1.1，优选为0.1-2.2环氧当量/kg的环氧树脂，
b)包含以下组分的组合物：组分A)一种上述通式(I)的1-咪唑甲基-取代的2-萘酚化合物和组分B)一种在室温下(RT＝15-35℃)为液态的酚，如正-戊基-，正-己基-，正-庚基-，正-辛基-，正-壬基-，正-癸基酚，特别是O，O’-二烯丙基-双酚A，组分A)与组分B)的重量比(重量％)为10∶90-80∶20，优选为20∶80-70∶30，更优选为25∶75-50∶50，
c)用于环氧树脂的固化剂，以及任选的
d)环氧树脂工艺中惯用的添加剂。
原则上讲，所有的环氧树脂都适合做组分(a)。
合适的实例包括脂环族多元醇，例如2，2-双(4’-羟基环己基)丙烷的二缩水甘油醚或聚缩水甘油醚，多羟基酚，如间苯二酚，双(4’-羟苯基)甲烷(双酚F)，2，2-双(4’-羟苯基)丙烷(双酚A)，2，2-双(4’-羟基-3’，5’-二溴苯基)丙烷，1，1，2，2-四(4’-羟苯基)乙烷的二缩水甘油醚或聚缩水甘油醚，或酚与甲醛的缩合产物，如酚酚醛树脂和甲酚酚醛树脂；另外还有上述引用的多元醇和聚酚的二-或聚(β-甲基缩水甘油)醚，多元羧酸如邻苯二甲酸，对苯二酸，四氢邻苯二甲酸和六氢邻苯二甲酸的聚缩水甘油醚和聚(β-甲基缩水甘油)醚；氨基酚的缩水甘油衍生物，如三缩水甘油-对-氨基酚；胺，酰胺和杂环氮碱，如N，N-二缩水甘油苯胺，N，N--二缩水甘油甲苯胺，N，N，N，N-四缩水甘油-双(4-氨基苯)甲烷，三缩水甘油异氰尿酸酯，N，N-二缩水甘油-N，N’-亚乙基脲，N，N’-二缩水甘油-5，5-二甲基乙内酰脲，N，N’-二缩水甘油-5-异丙基乙内酰脲，N，N’-二缩水甘油-5，5-二甲基-6-异丙基-5，6-二氢尿嘧啶的N-缩水甘油衍生物；多官能环氧树脂，如EP-A 205409和EP-A 204659所描述的2，6-二取代4-环氧丙苯基缩水甘油醚及其加成物；由两个缩水甘油氧基团和2，3-环氧丙基基团取代的双酚，如GB 828364中所描述的2，2-双(3’-环氧丙基-4’-环氧丙苯基)丙烷；四羟甲基取代的环己醇，环己酮、环戊醇和环戊酮的缩水甘油衍生物，如US 4,549,008中所描述的化合物；缩水甘油氧取代的二苯甲酮；以及缩水甘油氧二酮，US 4,649,181中所描述的化合物。
一般而言，也可以使用两种或两种以上环氧树脂的混合物作为本发明配方中的组分。
适合的环氧树脂优选包括缩水甘油醚如双酚A或F，缩水甘油酯，芳族或杂环化合物的N-缩水甘油衍生物和N，O-缩水甘油衍生物，以及脂环族缩水甘油化合物。优选具有官能度0.1-2.2环氧当量/kg的环氧树脂。
原则上讲，环氧树脂化学领域所惯用的所有固化剂都能用作本发明的固化剂，或组分(c)，例如胺，双氰胺，氰基胍，三聚氰胺，酚醛，例如包括甲酚-酚醛，多元醇和酸酐。
优选使用的固化剂为胺和聚胺，例如Jeffamine类，及其它的胺和聚胺。可提及的具体实例包括邻-，间-，和对-，苯二胺；二氨基甲苯，如2，4-甲苯二胺，1，4-二氨基-2-甲氧基苯，2，5-二氨基二甲苯，1，3-二氨基-4-氯苯，4，4’-二氨基二苯基甲烷，4，4’-二氨基二苯基醚，4，4’-二氨基二苯基硫醚，4，4’-二氨基二苯基砜，2，2’-二氨基苯甲酮，1，8-或1，5-二氨基萘，2，6-二氨基吡啶，1，4-哌嗪，2，4-二氨基嘧啶，2，4-二氨基-s-三嗪，二-，三-，四-，六-，七-，八-，和十-亚甲基二胺，3-甲基环庚烷-1，6-二胺，3-甲氧基六亚甲基二胺，2，11-二氨基十二烷，2，2，4-和2，4，4-三甲基六亚甲基二胺，1，2-双(3-氨基丙氧基)乙烷，N，N’-二甲基乙二胺，N，N’-二甲基-1，6-二氨基己烷以及分子式为H2N(CH2)3O(CH2)2O(CH2)3-NH2和H2N(CH2)3S(CH2)3NH2的二胺，1，4-二氨基环己烷，1，4-双(2-甲基-4-氨苯基)苯，1，4-双(氨甲基)苯。
另外适用的胺有碳环-芳族二胺，特别是取代的双核二胺，如双(3，5-二异丙基-4-氨苯基)甲烷，双(2-氯-3，5-二乙基-4-氨苯基)甲烷，双(3-乙基-4-氨基-5-仲-丁苯基)甲烷，双(2-氯-3，5-二乙基-4-氨苯基)甲烷和双(3，5-二乙基-4-氨苯基)甲烷。
另外适用的胺有丙烷-1，3-二胺，间-二甲苯二胺，双(4-氨基环己基)丙烷，3-氨甲基-3，5，5-三甲基环己基胺(异佛尔酮二胺)，聚氨基酰胺，例如包含脂肪族聚胺和脂肪酸的二聚或三聚物的聚氨基酰胺；多酚，如间苯二酚，对苯二酚，双酚A和酚/乙醛树脂，以及聚硫醇如″Thiokols”。
特别优选的是二胺或聚胺，氨基封端的聚亚烷基二醇和聚环氧丙二胺(如Jeffamine胺，此处用Jeffamine D-230，氨基-多-四氢呋喃)或聚氨基酰胺，特别是含氨基封端的基丙二醇和乙二醇的二聚物或共聚物，分子量为150-5000，优选200-600的氨基封端的聚丁二烯。
对于任选组分d)，可选用环氧树脂工艺中惯用的添加剂。即涉及特殊应用时本领域技术人员所知道和使用的那些常用助剂和添加剂。实例包括有机或无机的填料和颜料，脱模剂，以及影响粘度的添加剂。
在制备本发明的可固化组合物时，预先将本发明的促进剂在普通高温下溶解到固化剂中：例如使用一种固化剂时，在大约80℃下溶解促进剂。然后将溶液冷却到40℃，再与环氧树脂混合。该混合物可直接用做浸渍溶液。另外也可以预先将本发明的促进剂均匀地分散在环氧树脂中，例如采用适合的搅拌方法进行分散，如采用Ultra-Turrax或三辊磨。
按包括环氧树脂、固化剂、促进剂以及添加剂(若选用)总组成计，优选加入5-40份重的本发明化合物，特别优选加入5-30份，特别优选加入5-20份。固化剂按惯用量加入，因此可按平均每个环氧基团加入0.5-1.5，优选0.8-1.2个固化剂官能团来计算。原则上讲，助剂和添加剂的加入量范围可以很宽，只要不导致预期组合物粘度的大幅增加即可。
含有本发明这类促进剂体系的半固化片能使ILS值高这50Mpa。因此本发明促进剂特别适合在用作压塑材料，烧结粉末，封铸体系，或浇铸树脂的环氧树脂配方中使用，也适合采用湿铺叠法和注射成型法生产半固化片和层压制品时使用，特别适合生产大表面积的部件。
实验部分
a)包含萘酚组分和酚组分的组合物的制备
先在容器中装入酚组分，然后再加入萘酚组分。从下表1可以看出它们的使用量。混合物在160℃下搅拌4小时。得到发粘的、颜色从暗红到黑色的高粘度液体或固体。
表1
| 实验 | 1 | 2 | 3 | 4 |
| 萘酚<sup>1)</sup>[重重％] | 10 | 30 | 50 | 70 |
| 酚<sup>2)</sup>[重量％] | 90 | 70 | 50 | 30 |
| 状态 | 液态 | 液态 | 固态 | 固态 |
| 粘度η<sub>60℃</sub>[Pa·s] | ng<sup>3)</sup> | 28 | 6000 | nm<sup>3)</sup> |
1)1-咪唑甲基-取代的2-萘酚(购自Vantico AG)
2)二烯丙基双酚A(购自Vantico AG)
3)ng＝未测，nm＝在60℃下不可测，粘度用带有盘/盘装置的流变仪RheometrixRD2测定
b)本发明促进剂配方的应用实验
将上述实验a)部分得到的产物于60-80℃的温度下溶于胺固化剂中(此处用
D-230)。由此得到暗棕色透明溶液。冷却到室温后，将该溶液与计算量的环氧树脂混合。详情参见下表2。
表2
1)Araldite LY556双酚-A树脂(Vantico AG)
2)胺 
D-230
3)促进剂 1-咪唑甲基-2-萘酚(Vantico AG)
4)E2 实验2(参见表1)
5)制备 制备半固化片和层压制品的天数
6)半固化片 堆叠数＝l2
7)树脂含量 层压制品被压缩后的树脂百分含量
8)储存 在20-25℃＝室温下储存
9)Fmax ASTM D 2344中的极限强度(拉断载荷)
10)σmax ASTM D 2344中的剪切强度
ILS值a) 140℃下30分钟后的层间剪切强度(ILS)
ILS值b) 75℃下4小时后的层间剪切强度(ILS)
ILS值c) 75℃下8小时后的层间剪切强度(ILS)
ILS值d) 60℃下4小时后的层间剪切强度(ILS)
令人吃惊地是，用本发明的促进剂在低温范围(60和75℃/4-8小时)可以获得非常好的层间剪切强度。该值大大高于对比体系。
Claims (13)
1.包含下述组分的组合物：组分A)一种通式(I)的1-咪唑甲基-取代的2-萘酚化合物
其中
R1，R2和R3相互独立地分别为H；C1-17烷基；
C3-12环烷基，任选被C1-4烷基基团取代；
C4-20环烷基-烷基，任选被C1-4烷基基团取代；
C6-10芳基，任选被1-3个C1-4烷基基团取代；
C7-15苯烷基，任选被1-3个C1-4烷基基团取代；
C3-17烯基；C3-12炔基；或芳族或脂肪族C3-12酰基；
R4，R5，R6，R7，R8，和R9相互独立地分别为H；C1-12烷基；
C3-12环烷基，任选被C1-4烷基基团取代；
C4-20环烷基-烷基，任选被C1-4烷基基团取代；
C6-10芳基，任选被1-3个C1-4烷基基团取代；
C7-15苯烷基，任选被1-3个C1-4烷基基团取代；
C3-17烯基；C3-12炔基；C1-12烷氧基；或OH；以及
组分B)一种在15到35℃下为液态的酚，组分A)与组分B)的重量比为10∶90-80∶20。
2.根据权利要求1所述的组合物，其中所包含的组分A)化合物中的R1，R2和R3相互独立地分别为H，C1-12烷基，苯基或C7-15苯烷基，任选被1-3个C1-4烷基基团取代。
3.根据权利要求2所述的组合物，其中所包含的组分A)化合物中的R2和R3分别为H；同时R1为C1-12烷基；苯基；或C7-15苯烷基，任选被1-3个C1-4烷基基团取代。
4.根据权利要求3所述的组合物，其中所包含的组分A)通式(I)化合物中基团R2到R9为氢原子，同时基团R1为C1-4烷基；或苯基，任选被1-3个C1-4烷基基团取代。
5.根据权利要求1所述的组合物，其特征在于组分B)为1，4-正-戊基-，-正-己基-，-正-庚基-，-正-辛基-，-正-壬基-，-正-癸基酚或O，O’-二烯丙基-双酚A。
6.根据权利要求1所述的组合物，其特征在于组分A)与组分B)的重量比为20∶80-70∶30。
7.根据权利要求6所述的组合物，其特征在于组分A)与组分B)的重量比为25∶75-50∶50。
8.权利要求1所述的组合物作为促进剂在环氧树脂组合物中的应用。
9.可固化组合物，包括
a)环氧化物含量为0.1-1.1环氧当量/kg的环氧树脂，
b)权利要求1所述的组合物，
c)用于环氧树脂的固化剂，其加入量按每个环氧基团加入0.5-1.5个固化剂官能团来计算，以及任选的
d)环氧树脂工艺中惯用的添加剂。
10.根据权利要求9所述的组合物，其特征在于所述的固化剂选自胺。
11.根据权利要求10所述的组合物，其特征在于所述的固化剂是聚氧基亚丙基二胺。
12.根据权利要求9所述的组合物，其特征在于所用的环氧树脂为缩水甘油醚，缩水甘油酯，芳族或杂环化合物的N-缩水甘油基或N，O-缩水甘油基衍生物，或脂环族缩水甘油基化合物。
13.权利要求9所述的可固化组合物作为压塑材料，烧结粉末，封铸体系，浇铸树脂，用浸渍法和注射法生产预浸渍制品和层压制品，或生产元部件的应用。
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| US (1) | US7858713B2 (zh) |
| EP (1) | EP1613680B1 (zh) |
| JP (1) | JP4612625B2 (zh) |
| KR (1) | KR101096611B1 (zh) |
| CN (1) | CN100575384C (zh) |
| AT (1) | ATE346877T1 (zh) |
| DE (1) | DE602004003485T2 (zh) |
| ES (1) | ES2274446T3 (zh) |
| TW (1) | TWI336337B (zh) |
| WO (1) | WO2004092244A2 (zh) |
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| ITMI20091980A1 (it) * | 2009-11-12 | 2011-05-13 | Imast S C A R L | Polimeri rinforzati con fibre, composizioni polimeriche a base epossidica e loro impiego |
| JP5936340B2 (ja) * | 2011-12-13 | 2016-06-22 | 日本合成化学工業株式会社 | エポキシ樹脂用硬化剤 |
| JP2017082052A (ja) * | 2015-10-26 | 2017-05-18 | 住友ベークライト株式会社 | エポキシ樹脂組成物、及びこれを用いた半導体装置 |
| WO2018119250A1 (en) * | 2016-12-21 | 2018-06-28 | Huntsman Advanced Materials Licensing (Switzerland) Gmbh | Latent curing accelerators |
| KR102605531B1 (ko) * | 2021-11-02 | 2023-11-22 | (재)울산테크노파크 | 에폭시접착제 조성물 및 그 제조방법 |
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| US20020058756A1 (en) * | 1999-12-17 | 2002-05-16 | Loctite Corporation | Underfill sealants with improved adhesion, improved resistance to moisture absorption and improved resistance to stress cracking |
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| DE3479810D1 (en) * | 1983-08-24 | 1989-10-26 | Ciba Geigy Ag | Method of producing prepregs and composite materials reinforced therewith |
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- 2004-04-13 CN CN200480010048A patent/CN100575384C/zh not_active Expired - Lifetime
- 2004-04-13 US US10/552,908 patent/US7858713B2/en not_active Expired - Lifetime
- 2004-04-13 KR KR1020057019660A patent/KR101096611B1/ko active IP Right Grant
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- 2004-04-13 WO PCT/EP2004/050503 patent/WO2004092244A2/en active IP Right Grant
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- 2004-04-13 DE DE602004003485T patent/DE602004003485T2/de not_active Expired - Lifetime
- 2004-04-13 AT AT04727014T patent/ATE346877T1/de active
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|---|---|---|---|---|
| EP0086102A2 (en) * | 1982-02-08 | 1983-08-17 | INTEREZ, Inc.(a Delaware corporation) | Poyol/imidazole curing agents for epoxy resins |
| EP0761709A2 (en) * | 1995-09-12 | 1997-03-12 | Ciba SC Holding AG | 1-Imidazolylmethyl-2-naphthols as catalysts for curing epoxy resins |
| US20020058756A1 (en) * | 1999-12-17 | 2002-05-16 | Loctite Corporation | Underfill sealants with improved adhesion, improved resistance to moisture absorption and improved resistance to stress cracking |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004092244A2 (en) | 2004-10-28 |
| WO2004092244A3 (en) | 2004-12-23 |
| US20070100114A1 (en) | 2007-05-03 |
| CN1774461A (zh) | 2006-05-17 |
| TWI336337B (en) | 2011-01-21 |
| JP4612625B2 (ja) | 2011-01-12 |
| EP1613680B1 (en) | 2006-11-29 |
| DE602004003485D1 (de) | 2007-01-11 |
| US7858713B2 (en) | 2010-12-28 |
| KR101096611B1 (ko) | 2011-12-21 |
| KR20050121266A (ko) | 2005-12-26 |
| JP2006523746A (ja) | 2006-10-19 |
| ATE346877T1 (de) | 2006-12-15 |
| DE602004003485T2 (de) | 2007-09-20 |
| TW200504110A (en) | 2005-02-01 |
| WO2004092244A9 (en) | 2005-11-10 |
| ES2274446T3 (es) | 2007-05-16 |
| EP1613680A2 (en) | 2006-01-11 |
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