WO2009014353A2 - Surface modified amine curing agent, and one-component type epoxy resin composition and anisotropic conductive adhesive having the same - Google Patents
Surface modified amine curing agent, and one-component type epoxy resin composition and anisotropic conductive adhesive having the same Download PDFInfo
- Publication number
- WO2009014353A2 WO2009014353A2 PCT/KR2008/004216 KR2008004216W WO2009014353A2 WO 2009014353 A2 WO2009014353 A2 WO 2009014353A2 KR 2008004216 W KR2008004216 W KR 2008004216W WO 2009014353 A2 WO2009014353 A2 WO 2009014353A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- curing agent
- epoxy resin
- amine curing
- compound
- Prior art date
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 81
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 58
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 58
- 150000001412 amines Chemical class 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 239000000853 adhesive Substances 0.000 title claims abstract description 30
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 30
- -1 organic acid compound Chemical class 0.000 claims abstract description 39
- 125000003277 amino group Chemical group 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 230000002093 peripheral effect Effects 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
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- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 8
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- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 8
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- 239000007795 chemical reaction product Substances 0.000 claims description 8
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 8
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 8
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 8
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 8
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- 235000011037 adipic acid Nutrition 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 4
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 4
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 4
- PVNIQBQSYATKKL-UHFFFAOYSA-N Glycerol trihexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- SNVRDQORMVVQBI-UPHRSURJSA-N (z)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C/C(=O)NN SNVRDQORMVVQBI-UPHRSURJSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- GUXKYJPGGCCVMX-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)C1=NC=CN1 GUXKYJPGGCCVMX-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 description 1
- JJWCTKUQWXYIIU-UHFFFAOYSA-N 2-Benzimidazolylguanidine Chemical compound C1=CC=C2NC(N=C(N)N)=NC2=C1 JJWCTKUQWXYIIU-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- NKVZFNUCUPOCQJ-UHFFFAOYSA-N 2-anilinopropanehydrazide Chemical compound NNC(=O)C(C)NC1=CC=CC=C1 NKVZFNUCUPOCQJ-UHFFFAOYSA-N 0.000 description 1
- CGWBIHLHAGNJCX-UHFFFAOYSA-N 2-butylguanidine Chemical compound CCCCNC(N)=N CGWBIHLHAGNJCX-UHFFFAOYSA-N 0.000 description 1
- LEHNQGSPRXHYRT-UHFFFAOYSA-N 2-dodecyl-1h-imidazole Chemical compound CCCCCCCCCCCCC1=NC=CN1 LEHNQGSPRXHYRT-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
- BWMDMTSNSXYYSP-UHFFFAOYSA-N 2-propylguanidine Chemical compound CCCNC(N)=N BWMDMTSNSXYYSP-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 description 1
- SZUPZARBRLCVCB-UHFFFAOYSA-N 3-(2-undecylimidazol-1-yl)propanenitrile Chemical compound CCCCCCCCCCCC1=NC=CN1CCC#N SZUPZARBRLCVCB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- ALHNLFMSAXZKRC-UHFFFAOYSA-N benzene-1,4-dicarbohydrazide Chemical compound NNC(=O)C1=CC=C(C(=O)NN)C=C1 ALHNLFMSAXZKRC-UHFFFAOYSA-N 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 1
- PGIIZKRIHBMFFU-UHFFFAOYSA-N butanedioic acid;2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1.OC(=O)CCC(O)=O PGIIZKRIHBMFFU-UHFFFAOYSA-N 0.000 description 1
- DKPYKVKJLWGNRU-UHFFFAOYSA-N butanedioic acid;2-methyl-1h-imidazole Chemical compound CC1=NC=C[NH2+]1.OC(=O)CCC([O-])=O DKPYKVKJLWGNRU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- JKXONPYJVWEAEL-UHFFFAOYSA-N oxiran-2-ylmethyl acetate Chemical compound CC(=O)OCC1CO1 JKXONPYJVWEAEL-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/186—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 using pre-adducts of epoxy compounds with curing agents with acids
-
- 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
- C08G59/50—Amines
- C08G59/54—Amino amides>
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
- H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
- H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives
- H05K3/323—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives by applying an anisotropic conductive adhesive layer over an array of pads
Definitions
- the present invention relates to a surface modified amine curing agent, and one- component type epoxy resin composition and anisotropic conductive adhesive having the same.
- Two-component type epoxy resin composition which needs to mix two liquids of epoxy resin and curing agent for usage, has an advantage that it can be cured at a room temperature.
- the epoxy resin and the curing agent should be kept separately and they should be weighed independently and then mixed as necessary, the two-component type epoxy resin composition is inconvenient in storage and handling, and it inevitably exhibits deteriorated efficiency in working.
- the one-component epoxy resin composition representatively includes amine curing agents.
- amine curing agents have problems that any amine curing agent having excellent storage stability exhibits a high curing agent and any amine curing agent having an excellent low-temperature curing property exhibits bad storage stability.
- an amine curing agent capable of providing a one-component epoxy resin composition exhibiting both of excellent low-temperature curing property and excellent storage stability is demanded.
- a so-called capsulated curing agent in which a core made of amine curing agent is coated with epoxy resin to form a shell has been proposed.
- Japanese Laid-open Patent Publication No. 2004-269721 and Korean Laid-open Patent Publication Nos. 2005-0057676 and 2006-85668 disclose a capsulated curing agent obtained by blocking reactive amino groups existing on the core surface made of amine curing agent into groups with urea couplings using toluene isocyanate or the like to modify the surface, and then capsulating them with epoxy resin.
- the isocyanate blocking agent is reacted with the epoxy resin forming the shell, thereby creating by- products.
- Japanese Laid-open Patent Publication No. 1993-209041 discloses a curing agent having a carbamate coupling obtained as reaction product between cyclic carbonate and primary amine.
- a curing time is disadvan- tageously elongated at a high temperature.
- Japanese Laid-open Patent Publication Nos. 2006-2138 and 2006-316250 proposed an epoxy resin composition containing a micro-capsulated curing promoter obtained by micro-capsulating acid anhydride.
- the micro-capsulated acid anhydride is simply used only as a curing promoter, so it is not sufficient for satisfying both rapid curing and storage stability. Disclosure of Invention Technical Problem
- the present invention is designed to solve the problems of the prior art, and therefore it is an object of the present invention to provide a latent amine curing agent with improved rapid curing property and improved storage stability, and a one-component epoxy resin composition and an anisotropic conductive adhesive having the same.
- the present invention provides a surface modified amine curing agent, which includes a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core.
- the peripheral layer lowers reactivity at a normal temperature due to the formed peripheral layer, thereby improving storage stability and keeping rapid curing property agreeably.
- the organic acid compound may be carboxylic acid, sulfonic acid, and acid anhydride, which can be used in single or in mixture.
- the organic acid compound may be preferably methasulfonic acid, p-toluenesulfonic acid, succinic acid anhydride, phthalic acid anhydride, maleic acid anhydride, formic acid, acetetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitin acid, stearic acid, oleic acid, linolenic acid, cyclohexane carboxylic acid, phenylacetic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, tartaric acid, adipic acid, pimelic acid, suberin acid, azelaic acid, sebacin acid, maleic acid, fumaric acid, hemimellitic acid, trimellitic acid, trimesinic acid, malic acid, for
- the amine curing agent with a reactive amino group preferably employs a reaction product between an epoxy resin compound and an amine compound.
- the core having the amine curing agent with a reactive amino group preferably has an average diameter of 0.1 to 50 ⁇ m, more preferably 0.5 to 10 ⁇ m, but not limitedly.
- the surface modified amine curing agent can be used as a latent curing agent of an epoxy resin composition.
- the one-component epoxy resin may be mixed with conductive particles and then used as an anisotropic conductive adhesive. Best Mode for Carrying Out the Invention
- a surface modified amine curing agent according to the present invention includes a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core.
- the present invention provides an amine curing agent capable of being used as the core of a masking curing agent, and it has its essential feature in that the peripheral layer is formed by reaction between a reactive amino group and an organic acid compound on the surface of the amine curing agent.
- a blocking agent is added the amine curing agent using an epoxy resin as a dispersing medium, thereby blocking the surface of the amine curing agent.
- an isocyanate blocking agent it reacts with the epoxy resin, which forms the shell, thereby creating by-products.
- the reactive amino group exposing on the surface of the core forms a new peripheral layer by reacting with the organic acid compound added according to the present invention.
- the organic acid compound may adopt any kind of organic acid compound capable of reacting with an amino group, and any person having ordinary skill in the art would understood its boundary.
- the organic acid compound may include carboxylic acid, sulfonic acid, and acid anhydride.
- the organic acid compound may be methasulfonic acid, p- toluenesulfonic acid, succinic acid anhydride, phthalic acid anhydride, maleic acid anhydride, formic acid, acetetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitin acid, stearic acid, oleic acid, linolenic acid, cyclohexane carboxylic acid, phenylacetic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, tartaric acid, adipic acid, pimelic acid, suberin acid, azelaic acid, sebacin acid, maleic acid, fumaric acid, hemimellitic acid, trimellitic acid, trimesinic acid, mal
- the amine curing agent with a reactive amino group may employ a common amine curing agent, for example a low molecular amine compound and an amine byproduct, which may also be used in combination.
- the low molecular amine compound may be a low molecular compound having a primary, secondary or tertiary amino group.
- the low molecular compound having a primary amino group includes, for example, primary amines such as ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, hexamethylene diamine, isophorone diamine, bis(4-amino-3-methylcyclohexyl)methane, diaminodicyclohexylmethane, methaxylene diamine, diamino diphenylmethane, diamino diphenylsulfone, and methaphenylene diamine; guanidines such as dicyandiamide, methylguanidine, ethylguanidine, propyl- guanidine, butylguanidine, dimethylguanidine, trimethylguanidine, phenylguanidine, diphenylguanidine, and toluylguanidine; acid hydrazides such as succinic acid di- hydrazide, adipic
- the low molecular compound having a secondary amino group includes, for example, piperidine, pyrrolidine, diphenylamind, 2-methylimidazole, and 2-ethyl-4-methylimidazole.
- the low molecular compound having a tertiary amino group includes, for example, l-cyanoethyl-2-undecyl-imidazole-trimellitate, imidazolyl succinic acid, 2-methylimidazole succinic acid, 2-ethylimidazole succinic acid, imidazoles such as 1 -cyanoethyl-2-methylimidazole, 1 -cyanoethyl-2-undecylimidazole, l-cyanoethyl-2-phenylimidazole, 2-methyl imidazole, 2-ethyl imidazole, 2-ethyl-4-methyl imidazole, 2-isopropyl imidazole, 2-dodecyl imidazole, 2-undecyl imidazole, 2-heptadecyl imidazole, 2-phenyl imidazole, l-benzyl-2-methyl imidazole, l-benzylitate
- the amine by-product means a compound having an amino group, obtained by reacting an amine compound with at least one compound selected from the group consisting of carboxylic acid compound, sulfonic acid compound, isocyanate compound, urea compound, and epoxy resin compound. Among them, a reaction product of epoxy resin compound and amine compound is preferred.
- the epoxy resin compound used for making such a reaction product may use mono epoxy compound or poly epoxy compound, in single or in mixture.
- the mono epoxy compound may be butylglycidylether, hexylglycidylether, phenyl- glycidylether, allylglycidylether, para-t-butylphenylglycidylether, ethyleneoxide, propyleneoxide, paraxylylglycidylether, glycidylacetate, glycidylbutylate, gly- cidylhexoate, glycidylbenzoate, and so on.
- the poly epoxy compound may be bisphenol-type epoxy resin obtained by glycidylizing bisphenols such as bisphenol A, bisphenol F, bisphenol AD, bisphenol S, tetramethylbisphenol A, tetramethylbisphenol AD, and tetramethylbisphenol S; epoxy resin obtained by glycidylizing bivalent phenols such as biphenol and dihydroxynaphthalene; epoxy resin obtained by glycidylizing trisphenols such as l,l,l-tris(4-hydroxyphenyl)methane; epoxy resin obtained by glycidylizing tetrakisphenol; epoxy resin obtained by glycidylizing novolaks such as phenolnovolak and cresolnovolak; aliphatic ether epoxy resin obtained by glycidylizing poly alcohol such as glycerin and poly ethylenegly col; etherester epoxy resin obtained by glycidylizing hydroxy carboxylic acid such as p- oxybenzoic acid
- the amine compound used in making such a reaction product may be a compound having at least one primary amino group and/or second amino group but not having tertiary amino group; for example a primary amine with no tertiary amino group such as methyl amine, ethyl amine, propyl amine, butyl amine, ethylene diamine, propylene diamine, hexamethylene diamine, and dimethylene triamine; and a second amine with no tertiary amino group such as dimethyl amine, dicyclohexyl amine, piperidine, and phenylethyl amine.
- a primary amine with no tertiary amino group such as methyl amine, ethyl amine, propyl amine, butyl amine, ethylene diamine, propylene diamine, hexamethylene diamine, and dimethylene triamine
- a second amine with no tertiary amino group such as dimethyl amine, dicyclohexyl
- a compound having at least one tertiary amino group and at least one activated hydrogen group for example amino alcohols such as 2-dimethylaminoethanol and triethanolamine, aminophenols, imidazoles, imidazolines, aminocarboxylic acids, and aminohydrazides, but the amine compound is not limited thereto.
- amino alcohols such as 2-dimethylaminoethanol and triethanolamine
- aminophenols aminophenols
- imidazoles imidazoles
- imidazolines aminocarboxylic acids
- aminohydrazides aminohydrazides
- reaction products of epoxy resin compound and amine compound purchasable in the market are AJICURE produced by AJINOMOTO FINE-TECHNO, FUJICURE produced by FUJI KASEI KOGYO, ADK HARDENER produced by ASAHI DENKA, Novacure produced by ASAHI KASEI, and so on.
- the surface modified amine curing agent employed in the present invention may have a lump shape, a capsulated shape or a powder shape, among which the capsulated shape and the powder shape are preferred.
- the core having the amine curing agent with a reactive amino group preferably has an average diameter of 0.1 to 50 ⁇ m, more preferably 0.5 to 10 ⁇ m, but not limitedly.
- the surface modified amine curing agent of the present invention is useful as a latent curing agent of a one-component epoxy resin composition.
- the aforementioned one-component epoxy resin composition may be used in various fields, and for example it is useful as an anisotropic conductive adhesive. That is to say, the one-component epoxy resin composition of the present invention is useful for electrically connecting fine circuits, for example connecting a TAB film to a print circuit board, as being used as an insulating adhesive component of the anisotropic conductive adhesive.
- the surface modified amine curing agent may be included by the content of 1 to 200 parts by weight, preferably 1 to 70 parts by weight, based on 100 parts by weight of epoxy resin.
- the one-component epoxy resin composition may exhibit more excellent heat resistance and adhesive force, and non-reacted curing agent does not remain in usage.
- conductive particles included in the anisotropic conductive adhesive material may adopt common ones.
- the conducive particles may have diameter of 0.1 to 200 ⁇ m, preferably 0.1 to 30 ⁇ m, for easiness of production and application to a circuit board with fine pattern.
- the conductive particles may be included, for example, by the content of 0.5 to 50 parts by weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of epoxy resin. In this case, it is possible to prevent inferior electric connection during the adhering process and also ensure better insulation in a horizontal direction.
- a film- forming polymer may be further included so as to make the adhesive material into a film shape when necessary.
- the film-forming polymer may adopt any material commonly used in the field.
- the film-forming polymer may be included by the content of 0.5 to 2000 parts by weight, preferably 10 to 140 parts by weight, based on 100 parts by weight of epoxy resin. In this case, the film strength and curing characteristic are more improved, and better practical application is ensured.
- a peel strength was measured using TA XT Plus (produced by Stable Micro
- thermosetting adhesive materials prepared according to the examples and the comparative examples were stored at 6O 0 C for 5 hours.
- FT-IR before and after the storage at 6O 0 C for 5 hours were measured, and a conversion rate of epoxy group was calculated.
- ⁇ is marked if the conversion rate is less than 20%
- O is marked if the conversion rate is not less than 20% but less than 40%
- ⁇ is marked if the conversion rate is not less than 40% but less than 60%
- X is marked if the conversion rate is 60% or above.
- a pattern was formed on the TCP to have line/space of 50/50 ⁇ m, and an anisotropic conductive adhesive material cut into a width of 1.5 mm was provisionally adhered to a soda glass without a pattern at 8O 0 C and IMPa for 3 seconds. Then, a releasing film was removed, and TCP was attached. Subsequently, it was adhered for 10 seconds at 185 0 C and 3MPa, and its peel strength was measured using Texture Analyzer.
- O is marked if the peel strength is not less than 15 N/cm and less than 20 N/cm
- ⁇ is marked if the peel strength is less than 15 N/cm but not less than 10 N/cm
- X is marked if the peel strength is less than 10 N/cm.
- a pattern was formed on the TCP to have line/space of 50/50 ⁇ m, and an anisotropic conductive adhesive material cut into a width of 1.5 mm was provisionally adhered to a soda glass without a pattern at 8O 0 C and IMPa for 3 seconds. Then, a releasing film was removed, and TCP was attached. Subsequently, it was adhered for 10 seconds at 185 0 C and 3MPa, and its connection resistance was measured. O is marked if the connection resistance is less than 1.5 ⁇ , ⁇ is marked if the connection resistance is not less than 1.5 ⁇ and less than 2.0 ⁇ , and X is marked if the connection resistance is 2.0 ⁇ or above.
- a pattern was formed on the TCP to have line/space of 50/50 ⁇ m, and an anisotropic conductive adhesive material cut into a width of 1.5 mm was provisionally adhered to a soda glass without a pattern at 8O 0 C and IMPa for 3 seconds. Then, a releasing film was removed, and TCP was attached. Subsequently, it was adhered for 10 seconds at 185 0 C and 3MPa, and its insulation reliability was measured by measuring an insulating resistance after 500 hours at 85°C/85% RH. It is determined as good if the in- sulating resistance is 10 9 ⁇ or above, and it is determined as bad if the insulating resistance is less than 10 9 ⁇ .
- the comparative example was substantially identical to the example 2, except that a micro capsulated curing agent (Novacure, HX-3941HP, produced by ASAHI KASEI) was used as the master-batch type curing agent.
- a micro capsulated curing agent Novacure, HX-3941HP, produced by ASAHI KASEI
- RE-310S bisphenol A epoxy resin, with an equivalent weight of 190, produced by
- RE-404S bisphenol F epoxy resin, with an equivalent weight of 170, produced by
- YP-50 phenoxy resin, produced by KUKDOCHEM
- H-I curing agents prepared according to the examples 1 to 12 of the present invention
- HX-3941HP Novacure, a micro capsulated curing agent, produced by ASAHI
- AU-210 gold-plating polymer, with an average diameter of 10 ⁇ m, produced by
- Y-9936 g ⁇ mm ⁇ -methacryloxypropyltriethoxysilane, produced by GE TOSHIBA
- the surface modified amine curing agent having a peripheral layer formed by reaction between an organic acid compound and a reactive amino group of a core made of an amine curing agent exhibits more excellent properties without forming a shell thereon.
- a one-component epoxy resin composition containing the amine curing agent with a surface-modified peripheral layer made of organic acid compound as a latent curing agent ensures improved storage stability and also keeps low temperature curing properties agreeably, so it may be useful in various fields such as anisotropic conductive adhesive.
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Abstract
A surface modified amine curing agent includes a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core. A one-component epoxy resin composition and an anisotropic conductive adhesive including the above surface modified amine curing agent exhibits rapid curing property and improved storage stability.
Description
Description
SURFACE MODIFIED AMINE CURING AGENT, AND ONE- COMPONENT TYPE EPOXY RESIN COMPOSITION AND ANISOTROPIC CONDUCTIVE ADHESIVE HAVING THE
SAME Technical Field
[1] The present invention relates to a surface modified amine curing agent, and one- component type epoxy resin composition and anisotropic conductive adhesive having the same. Background Art
[2] Two-component type epoxy resin composition, which needs to mix two liquids of epoxy resin and curing agent for usage, has an advantage that it can be cured at a room temperature. However, since the epoxy resin and the curing agent should be kept separately and they should be weighed independently and then mixed as necessary, the two-component type epoxy resin composition is inconvenient in storage and handling, and it inevitably exhibits deteriorated efficiency in working.
[3] In order to solve the drawbacks of the two-component type epoxy resin composition, a one-component epoxy resin composition using a latent curing agent, which causes a curing reaction by light irradiation or heating, has been developed. The one-component epoxy resin composition representatively includes amine curing agents. However, such amine curing agents have problems that any amine curing agent having excellent storage stability exhibits a high curing agent and any amine curing agent having an excellent low-temperature curing property exhibits bad storage stability. Thus, there is demanded an amine curing agent capable of providing a one-component epoxy resin composition exhibiting both of excellent low-temperature curing property and excellent storage stability.
[4] For such demands, a so-called capsulated curing agent in which a core made of amine curing agent is coated with epoxy resin to form a shell has been proposed. Japanese Laid-open Patent Publication No. 2004-269721 and Korean Laid-open Patent Publication Nos. 2005-0057676 and 2006-85668 disclose a capsulated curing agent obtained by blocking reactive amino groups existing on the core surface made of amine curing agent into groups with urea couplings using toluene isocyanate or the like to modify the surface, and then capsulating them with epoxy resin. However, in case a capsulated curing agent is prepared using an isocyanate blocking agent, the isocyanate blocking agent is reacted with the epoxy resin forming the shell, thereby creating by-
products.
[5] Meanwhile, Japanese Laid-open Patent Publication No. 1993-209041 discloses a curing agent having a carbamate coupling obtained as reaction product between cyclic carbonate and primary amine. However, in case reactive amino groups of the amine curing agent are all blocked with carbamate couplings, a curing time is disadvan- tageously elongated at a high temperature.
[6] Also, Japanese Laid-open Patent Publication Nos. 2006-2138 and 2006-316250 proposed an epoxy resin composition containing a micro-capsulated curing promoter obtained by micro-capsulating acid anhydride. Here, the micro-capsulated acid anhydride is simply used only as a curing promoter, so it is not sufficient for satisfying both rapid curing and storage stability. Disclosure of Invention Technical Problem
[7] The present invention is designed to solve the problems of the prior art, and therefore it is an object of the present invention to provide a latent amine curing agent with improved rapid curing property and improved storage stability, and a one-component epoxy resin composition and an anisotropic conductive adhesive having the same. Technical Solution
[8] In order to accomplish the above object, the present invention provides a surface modified amine curing agent, which includes a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core. In case the surface modified amine curing agent of the present invention, which has the peripheral layer formed by reaction of organic acid compound and reactive amino group existing on the surface of the core made of amine curing agent, is used, the peripheral layer lowers reactivity at a normal temperature due to the formed peripheral layer, thereby improving storage stability and keeping rapid curing property agreeably.
[9] In the surface modified amine curing agent according to the present invention, the organic acid compound may be carboxylic acid, sulfonic acid, and acid anhydride, which can be used in single or in mixture.
[10] The organic acid compound may be preferably methasulfonic acid, p-toluenesulfonic acid, succinic acid anhydride, phthalic acid anhydride, maleic acid anhydride, formic acid, acetetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitin acid, stearic acid, oleic acid, linolenic acid, cyclohexane carboxylic acid, phenylacetic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, tartaric acid, adipic acid, pimelic acid, suberin acid, azelaic acid, sebacin
acid, maleic acid, fumaric acid, hemimellitic acid, trimellitic acid, trimesinic acid, malic acid, trifluoroacetic acid, citric acid, sumanderic acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, vanillaic acid, and hydroiodic acid, which can be used in single or in mixture.
[11] In the surface modified amine curing agent according to the present invention, the amine curing agent with a reactive amino group preferably employs a reaction product between an epoxy resin compound and an amine compound. The core having the amine curing agent with a reactive amino group preferably has an average diameter of 0.1 to 50 μm, more preferably 0.5 to 10 μm, but not limitedly.
[12] The surface modified amine curing agent can be used as a latent curing agent of an epoxy resin composition.
[13] In addition, the one-component epoxy resin may be mixed with conductive particles and then used as an anisotropic conductive adhesive. Best Mode for Carrying Out the Invention
[14] Hereinafter, preferred embodiments of the present invention will be described in detail. Prior to the description, it should be understood that the terms used in the specification and the appended claims should not be construed as limited to general and dictionary meanings, but interpreted based on the meanings and concepts corresponding to technical aspects of the present invention on the basis of the principle that the inventor is allowed to define terms appropriately for the best explanation.
[15] A surface modified amine curing agent according to the present invention includes a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core.
[16] The present invention provides an amine curing agent capable of being used as the core of a masking curing agent, and it has its essential feature in that the peripheral layer is formed by reaction between a reactive amino group and an organic acid compound on the surface of the amine curing agent. Commonly, a blocking agent is added the amine curing agent using an epoxy resin as a dispersing medium, thereby blocking the surface of the amine curing agent. However, in such a conventional case that an isocyanate blocking agent is used, it reacts with the epoxy resin, which forms the shell, thereby creating by-products.
[17] However, in the case that an organic acid compound is used as a blocking agent for modifying the surface of the amine curing agent as in the present invention, there is no need of reaction with epoxy resin for forming a shell as in the conventional case. Thus, the surface modified curing agent particles of the present invention are just dispersed
in the epoxy resin, while ensuring excellent storage stability and excellent curing property.
[18] In the surface modified amine curing agent of the present invention, the reactive amino group exposing on the surface of the core forms a new peripheral layer by reacting with the organic acid compound added according to the present invention. The organic acid compound may adopt any kind of organic acid compound capable of reacting with an amino group, and any person having ordinary skill in the art would understood its boundary. For example, the organic acid compound may include carboxylic acid, sulfonic acid, and acid anhydride.
[19] In more detail, the organic acid compound may be methasulfonic acid, p- toluenesulfonic acid, succinic acid anhydride, phthalic acid anhydride, maleic acid anhydride, formic acid, acetetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitin acid, stearic acid, oleic acid, linolenic acid, cyclohexane carboxylic acid, phenylacetic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, tartaric acid, adipic acid, pimelic acid, suberin acid, azelaic acid, sebacin acid, maleic acid, fumaric acid, hemimellitic acid, trimellitic acid, trimesinic acid, malic acid, trifluoroacetic acid, citric acid, sumanderic acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, vanillaic acid, and hydroiodic acid.
[20] In addition, in the surface modified amine curing agent according to the present invention, the amine curing agent with a reactive amino group may employ a common amine curing agent, for example a low molecular amine compound and an amine byproduct, which may also be used in combination.
[21] The low molecular amine compound may be a low molecular compound having a primary, secondary or tertiary amino group.
[22] The low molecular compound having a primary amino group includes, for example, primary amines such as ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, hexamethylene diamine, isophorone diamine, bis(4-amino-3-methylcyclohexyl)methane, diaminodicyclohexylmethane, methaxylene diamine, diamino diphenylmethane, diamino diphenylsulfone, and methaphenylene diamine; guanidines such as dicyandiamide, methylguanidine, ethylguanidine, propyl- guanidine, butylguanidine, dimethylguanidine, trimethylguanidine, phenylguanidine, diphenylguanidine, and toluylguanidine; acid hydrazides such as succinic acid di- hydrazide, adipic acid dihydrazide, phthalic acid dihydrazide, isophthalic acid di- hydrazide, terephthalic acid dihydrazide, p-oxybenzoic acid hydrazide, salicylic acid hydrazide, phenylaminopropionic acid hydrazide, and maleic acid dihydrazide.
[23] The low molecular compound having a secondary amino group includes, for
example, piperidine, pyrrolidine, diphenylamind, 2-methylimidazole, and 2-ethyl-4-methylimidazole.
[24] The low molecular compound having a tertiary amino group includes, for example, l-cyanoethyl-2-undecyl-imidazole-trimellitate, imidazolyl succinic acid, 2-methylimidazole succinic acid, 2-ethylimidazole succinic acid, imidazoles such as 1 -cyanoethyl-2-methylimidazole, 1 -cyanoethyl-2-undecylimidazole, l-cyanoethyl-2-phenylimidazole, 2-methyl imidazole, 2-ethyl imidazole, 2-ethyl-4-methyl imidazole, 2-isopropyl imidazole, 2-dodecyl imidazole, 2-undecyl imidazole, 2-heptadecyl imidazole, 2-phenyl imidazole, l-benzyl-2-methyl imidazole, l-benzyl-2-phenyl imidazole, 1,2-dimethyl imidazole, l,l'-carbony Ibis (2-methyl imidazole), benzimidazole, l-(para-toluenesulfonyl)imidazole, l,l'-carbonylimidazole, l,l'-sulfonyldiimidazole, and 2-guanidinobenz imidazole; benzyldimethyl amine, tri- ethanolamine, 2,4,6-tris(dimethylaminomethyl)phenol, N,N'-dimethylpiperazine, tri- ethylenediamine, l,8-diazabicyclo(5,4,0)-undecene-7,l,5-diazabicyclo(4,3,0)-nonen-5, pyridine, and picoline.
[25] The amine by-product means a compound having an amino group, obtained by reacting an amine compound with at least one compound selected from the group consisting of carboxylic acid compound, sulfonic acid compound, isocyanate compound, urea compound, and epoxy resin compound. Among them, a reaction product of epoxy resin compound and amine compound is preferred. The epoxy resin compound used for making such a reaction product may use mono epoxy compound or poly epoxy compound, in single or in mixture.
[26] The mono epoxy compound may be butylglycidylether, hexylglycidylether, phenyl- glycidylether, allylglycidylether, para-t-butylphenylglycidylether, ethyleneoxide, propyleneoxide, paraxylylglycidylether, glycidylacetate, glycidylbutylate, gly- cidylhexoate, glycidylbenzoate, and so on. Also, the poly epoxy compound may be bisphenol-type epoxy resin obtained by glycidylizing bisphenols such as bisphenol A, bisphenol F, bisphenol AD, bisphenol S, tetramethylbisphenol A, tetramethylbisphenol AD, and tetramethylbisphenol S; epoxy resin obtained by glycidylizing bivalent phenols such as biphenol and dihydroxynaphthalene; epoxy resin obtained by glycidylizing trisphenols such as l,l,l-tris(4-hydroxyphenyl)methane; epoxy resin obtained by glycidylizing tetrakisphenol; epoxy resin obtained by glycidylizing novolaks such as phenolnovolak and cresolnovolak; aliphatic ether epoxy resin obtained by glycidylizing poly alcohol such as glycerin and poly ethylenegly col; etherester epoxy resin obtained by glycidylizing hydroxy carboxylic acid such as p- oxybenzoic acid; ester epoxy resin obtained by glycidylizing polycarboxylic acid such as phthalic acid and terephthalic acid; and alicyclic epoxide, but not limitedly.
[27] In addition, the amine compound used in making such a reaction product may be a
compound having at least one primary amino group and/or second amino group but not having tertiary amino group; for example a primary amine with no tertiary amino group such as methyl amine, ethyl amine, propyl amine, butyl amine, ethylene diamine, propylene diamine, hexamethylene diamine, and dimethylene triamine; and a second amine with no tertiary amino group such as dimethyl amine, dicyclohexyl amine, piperidine, and phenylethyl amine. In addition, a compound having at least one tertiary amino group and at least one activated hydrogen group, for example amino alcohols such as 2-dimethylaminoethanol and triethanolamine, aminophenols, imidazoles, imidazolines, aminocarboxylic acids, and aminohydrazides, but the amine compound is not limited thereto.
[28] The reaction products of epoxy resin compound and amine compound purchasable in the market are AJICURE produced by AJINOMOTO FINE-TECHNO, FUJICURE produced by FUJI KASEI KOGYO, ADK HARDENER produced by ASAHI DENKA, Novacure produced by ASAHI KASEI, and so on.
[29] The surface modified amine curing agent employed in the present invention may have a lump shape, a capsulated shape or a powder shape, among which the capsulated shape and the powder shape are preferred. The core having the amine curing agent with a reactive amino group preferably has an average diameter of 0.1 to 50 μm, more preferably 0.5 to 10 μm, but not limitedly.
[30] The surface modified amine curing agent of the present invention is useful as a latent curing agent of a one-component epoxy resin composition.
[31] The aforementioned one-component epoxy resin composition may be used in various fields, and for example it is useful as an anisotropic conductive adhesive. That is to say, the one-component epoxy resin composition of the present invention is useful for electrically connecting fine circuits, for example connecting a TAB film to a print circuit board, as being used as an insulating adhesive component of the anisotropic conductive adhesive.
[32] In the one-component epoxy resin composition of the present invention, for example the surface modified amine curing agent may be included by the content of 1 to 200 parts by weight, preferably 1 to 70 parts by weight, based on 100 parts by weight of epoxy resin. In the above content range, the one-component epoxy resin composition may exhibit more excellent heat resistance and adhesive force, and non-reacted curing agent does not remain in usage. In addition, conductive particles included in the anisotropic conductive adhesive material may adopt common ones. The conducive particles may have diameter of 0.1 to 200 μm, preferably 0.1 to 30 μm, for easiness of production and application to a circuit board with fine pattern.
[33] In the one-component epoxy resin composition of the present invention, the conductive particles may be included, for example, by the content of 0.5 to 50 parts by
weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of epoxy resin. In this case, it is possible to prevent inferior electric connection during the adhering process and also ensure better insulation in a horizontal direction.
[34] In the one-component epoxy resin composition of the present invention, a film- forming polymer may be further included so as to make the adhesive material into a film shape when necessary. The film-forming polymer may adopt any material commonly used in the field. For example, the film-forming polymer may be included by the content of 0.5 to 2000 parts by weight, preferably 10 to 140 parts by weight, based on 100 parts by weight of epoxy resin. In this case, the film strength and curing characteristic are more improved, and better practical application is ensured. Mode for the Invention
[35] Hereinafter, various preferred examples of the present invention will be described in detail for better understandings. However, the examples of the present invention may be modified in various ways, and they should not be interpreted as limiting the scope of the invention. The examples of the present invention are just for better understandings of the invention to persons having ordinary skill in the art.
[36] According to the above method, properties of resins and its curing materials according to examples and comparative examples were evaluated.
[37]
[38] 1. FT-IR (Fourier Transform Infrared Spectrometer) Measurement
[39] An optical absorptive degree was measured using Bio-Rad FTS3000 (produced by
Bio Rad).
[40]
[41] 2. DSC (Differential Scanning Calorimeter) Measurement
[42] A maximum exothermic peak was measured using TA DSC 2010 (produced by TA
Instrument).
[43]
[44] 3. Texture Analyzer Measurement
[45] A peel strength was measured using TA XT Plus (produced by Stable Micro
Systems, Ltd.).
[46]
[47] 4. Curing Property
[48] DSC of the produced thermosetting adhesive materials was measured (with a temperature increasing speed of 10°C/min), and then caloric values before and after curing were compared to calculate a curing rate. The case that the curing rate is 70% or above is represented with O, the case that the curing rate is not less than 50% and less than 70% is represented with Δ, and the case that the curing rate is less than 50% is rep-
resented with X. [49] [50] 5. Storage Stability
[51] The thermosetting adhesive materials prepared according to the examples and the comparative examples were stored at 6O0C for 5 hours. FT-IR before and after the storage at 6O0C for 5 hours were measured, and a conversion rate of epoxy group was calculated. © is marked if the conversion rate is less than 20%, O is marked if the conversion rate is not less than 20% but less than 40%, Δ is marked if the conversion rate is not less than 40% but less than 60%, and X is marked if the conversion rate is 60% or above.
[52]
[53] 6. Peel Strength
[54] A pattern was formed on the TCP to have line/space of 50/50 μm, and an anisotropic conductive adhesive material cut into a width of 1.5 mm was provisionally adhered to a soda glass without a pattern at 8O0C and IMPa for 3 seconds. Then, a releasing film was removed, and TCP was attached. Subsequently, it was adhered for 10 seconds at 1850C and 3MPa, and its peel strength was measured using Texture Analyzer. O is marked if the peel strength is not less than 15 N/cm and less than 20 N/cm, Δ is marked if the peel strength is less than 15 N/cm but not less than 10 N/cm, and X is marked if the peel strength is less than 10 N/cm.
[55]
[56] 7. Connection Resistance
[57] A pattern was formed on the TCP to have line/space of 50/50 μm, and an anisotropic conductive adhesive material cut into a width of 1.5 mm was provisionally adhered to a soda glass without a pattern at 8O0C and IMPa for 3 seconds. Then, a releasing film was removed, and TCP was attached. Subsequently, it was adhered for 10 seconds at 1850C and 3MPa, and its connection resistance was measured. O is marked if the connection resistance is less than 1.5 Ω, Δ is marked if the connection resistance is not less than 1.5 Ω and less than 2.0 Ω, and X is marked if the connection resistance is 2.0 Ω or above.
[58]
[59] 8. Insulation Reliability
[60] A pattern was formed on the TCP to have line/space of 50/50 μm, and an anisotropic conductive adhesive material cut into a width of 1.5 mm was provisionally adhered to a soda glass without a pattern at 8O0C and IMPa for 3 seconds. Then, a releasing film was removed, and TCP was attached. Subsequently, it was adhered for 10 seconds at 1850C and 3MPa, and its insulation reliability was measured by measuring an insulating resistance after 500 hours at 85°C/85% RH. It is determined as good if the in-
sulating resistance is 109Ω or above, and it is determined as bad if the insulating resistance is less than 109Ω.
[61]
[62] Examples 1 to 4
[63] After an epoxy resin amine curing agent (Ajicure, produced by Ajinomoto fine- techno, with an average diameter of 2.5 μm) is dispersed in a solvent (xylene), 5 parts by weight of adipic acid was added to 100 parts by weight of the curing agent and stirred at 50 0C, and then the curing agent having reacted with the adipic acid was separation-dried into powder. Then, FT-IR was measured, and so it was checked that the adipic acid reacted with the surface of the curing agent to form a peripheral layer.
[64] 50 parts by weight of the prepared curing agent was added to 100 parts by weight of bisphenol A epoxy resin (equivalent weight of epoxy was 185g/equivalent, and an amount of entire chlorine was 1200 ppm), and then evenly dispersed to obtain a master-batch type curing agent. Adhesive components shown in the following table 1 and a mixture solvent of toluene and ethylacetate were added to the master-batch type curing agent, then stirred, and then vacuum-degassed. This solution was then applied to a polyethylene terephthalate substrate with a thickness of 50 μm such that it has a thickness of 25 μm after being dried, thereby obtaining a thermosetting adhesive material. The used adhesive components and their contents and also measured properties of the adhesive material are shown in the following table 1.
[65]
[66] Examples 5 to 8
[67] These examples were substantially identical to the examples 1 to 4, respectively, except that p-toluene sulfonic acid was used as an organic compound.
[68]
[69] Examples 9 to 12
[70] These examples were substantially identical to the examples 1 to 4, respectively, except that phthalic acid anhydride was used as an organic compound.
[71]
[72] Comparative Example
[73] The comparative example was substantially identical to the example 2, except that a micro capsulated curing agent (Novacure, HX-3941HP, produced by ASAHI KASEI) was used as the master-batch type curing agent.
[74]
[75] Table 1
[Table 1] [Table ]
[76] (unit: parts by weight)
[77] where CE. represents the comparative example, and G represents "Good"
[78]
[79] Components used in the table 1 is as follows:
[80]
[81] <Epoxy Resin>
[82] RE-310S: bisphenol A epoxy resin, with an equivalent weight of 190, produced by
Japan Powder [83] RE-404S: bisphenol F epoxy resin, with an equivalent weight of 170, produced by
Japan Powder [84]
[85] <Film-forming Polymer>
[86] SG-P3: epoxy group-containing acryl rubber, produced by NAGASE CHEMTECHS
[87] YP-50: phenoxy resin, produced by KUKDOCHEM
[88]
[89] <Master-Batch type Curing Agent>
[90] H-I: curing agents prepared according to the examples 1 to 12 of the present invention [91] HX-3941HP: Novacure, a micro capsulated curing agent, produced by ASAHI
KASEI EPOXY [92]
[93] <Conductive Particle>
[94] AU-210: gold-plating polymer, with an average diameter of 10 μm, produced by
SEGISUI CHEM [95] AU-205: gold-plating polymer, with an average diameter of 5 μm, produced by
SEGISUI CHEM [96]
[97] <Silane Coupling Agent>
[98] Y-9936: gαmmα-methacryloxypropyltriethoxysilane, produced by GE TOSHIBA
SILICONS [99] [100] Seeing the table 1, it would be understood that the adhesive of the present invention exhibits a rapid curing speed and excellent storage stability, while the adhesive of the comparative example exhibits similar curing properties but deteriorated storage stability in comparison to that of the present invention.
Industrial Applicability [101] As described above, the surface modified amine curing agent having a peripheral layer formed by reaction between an organic acid compound and a reactive amino group of a core made of an amine curing agent exhibits more excellent properties
without forming a shell thereon. Thus, a one-component epoxy resin composition containing the amine curing agent with a surface-modified peripheral layer made of organic acid compound as a latent curing agent ensures improved storage stability and also keeps low temperature curing properties agreeably, so it may be useful in various fields such as anisotropic conductive adhesive.
Claims
[1] A surface modified amine curing agent, comprising: a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core.
[2] The surface modified amine curing agent according to claim 1, wherein the organic acid compound is at least one material selected from the group consisting of carboxylic acid, sulfonic acid, and acid anhydride.
[3] The surface modified amine curing agent according to claim 1, wherein the organic acid compound is at least one material selected from the group consisting of methasulfonic acid, p-toluenesulfonic acid, succinic acid anhydride, phthalic acid anhydride, maleic acid anhydride, formic acid, acetetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitin acid, stearic acid, oleic acid, linolenic acid, cyclohexane carboxylic acid, phenylacetic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, tartaric acid, adipic acid, pimelic acid, suberin acid, azelaic acid, sebacin acid, maleic acid, fumaric acid, hemimellitic acid, trimellitic acid, trimesinic acid, malic acid, trifluoroacetic acid, citric acid, sumanderic acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, vanillaic acid, and hydroiodic acid.
[4] The surface modified amine curing agent according to claim 1, wherein the amine curing agent with a reactive amino group is a reaction product between an epoxy resin compound and an amine compound.
[5] The surface modified amine curing agent according to claim 1, wherein the core having the amine curing agent with a reactive amino group has an average diameter of 0.1 to 50 μm.
[6] A one-component type epoxy resin composition containing an epoxy resin and a latent curing agent, the latent curing agent comprising: a core having an amine curing agent with a reactive amino group; and a peripheral layer formed by reaction between an organic acid compound and the reactive amino group existing on the surface of the core.
[7] The one-component type epoxy resin composition according to claim 6, wherein the organic acid compound is at least one material selected from the group consisting of carboxylic acid, sulfonic acid, and acid anhydride.
[8] The one-component type epoxy resin composition according to claim 6,
wherein the organic acid compound is at least one material selected from the group consisting of methasulfonic acid, p-toluenesulfonic acid, succinic acid anhydride, phthalic acid anhydride, maleic acid anhydride, formic acid, acetetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitin acid, stearic acid, oleic acid, linolenic acid, cyclohexane carboxylic acid, phenylacetic acid, benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, tartaric acid, adipic acid, pimelic acid, suberin acid, azelaic acid, sebacin acid, maleic acid, fumaric acid, hemimellitic acid, trimellitic acid, trimesinic acid, malic acid, trifluoroacetic acid, citric acid, sumanderic acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, vanillaic acid, and hydroiodic acid.
[9] The one-component type epoxy resin composition according to claim 6, wherein the amine curing agent with a reactive amino group is a reaction product between an epoxy resin compound and an amine compound.
[10] The one-component type epoxy resin composition according to claim 6, wherein the core having the amine curing agent with a reactive amino group has an average diameter of 0.1 to 50 μm.
[11] An anisotropic conductive adhesive, which contains an insulating adhesive component and a plurality of conductive particles dispersed in the insulating adhesive component, wherein the insulating adhesive component is the one-component type epoxy resin composition defined in any one of the claims 6 to 10.
[12] The anisotropic conductive adhesive according to claim 11, wherein the conductive particles have diameters of 0.1 to 200 μm.
[13] The anisotropic conductive adhesive according to claim 11, further comprising a film-forming polymer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070073127A KR20090009660A (en) | 2007-07-20 | 2007-07-20 | A surface modified amines curing agent, and a one-component type epoxy resin composition and anisotropic conductive adhesive comprising the curing agent |
| KR10-2007-0073127 | 2007-07-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2009014353A2 true WO2009014353A2 (en) | 2009-01-29 |
| WO2009014353A3 WO2009014353A3 (en) | 2009-03-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2008/004216 WO2009014353A2 (en) | 2007-07-20 | 2008-07-18 | Surface modified amine curing agent, and one-component type epoxy resin composition and anisotropic conductive adhesive having the same |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR20090009660A (en) |
| WO (1) | WO2009014353A2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7238795B2 (en) | 2000-08-03 | 2007-07-03 | Roche Molecular Systems, Inc. | Nucleic acid binding compounds containing pyrazolo[3,4-d]pyrimidine analogues of purin-2,6-diamine and their uses |
| CN103387808A (en) * | 2012-05-08 | 2013-11-13 | 长春市三化实业有限责任公司 | Polishable flame-retarding automobile structural adhesive and preparation method thereof |
| US20210261829A1 (en) * | 2020-02-26 | 2021-08-26 | Korea Advanced Institute Of Science And Technology | Anisotropic conductive adhesives for thermo-compression bonding containing solder conductive particles and flux additives and method of connecting electronic parts using the same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109735276B (en) * | 2019-01-11 | 2021-03-26 | 华玻视讯(珠海)科技有限公司 | Micron copper sheet-polyphenyl ether-epoxy resin conductive adhesive and preparation method thereof |
| CN114573790B (en) * | 2022-03-17 | 2023-11-17 | 宁波锋成绿能环保科技有限公司 | Bio-based degradable epoxy resin, preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004269721A (en) * | 2003-03-10 | 2004-09-30 | Asahi Kasei Chemicals Corp | Masterbatch curing agent and one-component type epoxy resin composition |
| KR20050057676A (en) * | 2002-10-25 | 2005-06-16 | 아사히 가세이 케미칼즈 가부시키가이샤 | Capsule type hardener and composition |
| KR20070031525A (en) * | 2005-09-15 | 2007-03-20 | 주식회사 코오롱 | Anisotropic conductive film, manufacturing method thereof and its usage |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5235007A (en) * | 1991-10-03 | 1993-08-10 | Texaco Chemical Company | Epoxy curing agents |
| JP3199818B2 (en) * | 1992-03-06 | 2001-08-20 | 松本油脂製薬株式会社 | Microcapsules for epoxy resin curing agent |
-
2007
- 2007-07-20 KR KR1020070073127A patent/KR20090009660A/en not_active Application Discontinuation
-
2008
- 2008-07-18 WO PCT/KR2008/004216 patent/WO2009014353A2/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050057676A (en) * | 2002-10-25 | 2005-06-16 | 아사히 가세이 케미칼즈 가부시키가이샤 | Capsule type hardener and composition |
| JP2004269721A (en) * | 2003-03-10 | 2004-09-30 | Asahi Kasei Chemicals Corp | Masterbatch curing agent and one-component type epoxy resin composition |
| KR20070031525A (en) * | 2005-09-15 | 2007-03-20 | 주식회사 코오롱 | Anisotropic conductive film, manufacturing method thereof and its usage |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7238795B2 (en) | 2000-08-03 | 2007-07-03 | Roche Molecular Systems, Inc. | Nucleic acid binding compounds containing pyrazolo[3,4-d]pyrimidine analogues of purin-2,6-diamine and their uses |
| CN103387808A (en) * | 2012-05-08 | 2013-11-13 | 长春市三化实业有限责任公司 | Polishable flame-retarding automobile structural adhesive and preparation method thereof |
| CN103387808B (en) * | 2012-05-08 | 2015-08-19 | 长春市三化实业有限责任公司 | One can be polished flame retardant resistance vehicle structure glue composition and preparation method thereof |
| US20210261829A1 (en) * | 2020-02-26 | 2021-08-26 | Korea Advanced Institute Of Science And Technology | Anisotropic conductive adhesives for thermo-compression bonding containing solder conductive particles and flux additives and method of connecting electronic parts using the same |
| US11732162B2 (en) * | 2020-02-26 | 2023-08-22 | Korea Advanced Institute Of Science And Technology | Anisotropic conductive adhesives for thermo-compression bonding containing solder conductive particles and flux additives and method of connecting electronic parts using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009014353A3 (en) | 2009-03-19 |
| KR20090009660A (en) | 2009-01-23 |
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