JP2002509178A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002509178A5 JP2002509178A5 JP2000540193A JP2000540193A JP2002509178A5 JP 2002509178 A5 JP2002509178 A5 JP 2002509178A5 JP 2000540193 A JP2000540193 A JP 2000540193A JP 2000540193 A JP2000540193 A JP 2000540193A JP 2002509178 A5 JP2002509178 A5 JP 2002509178A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- epoxy resin
- acid
- alkyl
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 description 470
- 239000003822 epoxy resin Substances 0.000 description 166
- 229920000647 polyepoxide Polymers 0.000 description 164
- 125000000217 alkyl group Chemical group 0.000 description 106
- 239000007787 solid Substances 0.000 description 77
- 239000004593 Epoxy Substances 0.000 description 66
- 239000002253 acid Substances 0.000 description 61
- 238000001723 curing Methods 0.000 description 60
- 150000007524 organic acids Chemical class 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 46
- 239000003795 chemical substances by application Substances 0.000 description 43
- 239000000853 adhesive Substances 0.000 description 42
- 229920006295 polythiol Polymers 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 37
- 230000001070 adhesive effect Effects 0.000 description 36
- 239000002245 particle Substances 0.000 description 34
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 33
- 239000000758 substrate Substances 0.000 description 33
- 125000003342 alkenyl group Chemical group 0.000 description 27
- 239000004065 semiconductor Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- -1 aromatic carboxylic acids Chemical class 0.000 description 22
- 125000001188 haloalkyl group Chemical group 0.000 description 21
- 230000009974 thixotropic effect Effects 0.000 description 21
- 238000002156 mixing Methods 0.000 description 20
- 239000001530 fumaric acid Substances 0.000 description 19
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
- 229910052794 bromium Inorganic materials 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 229910052731 fluorine Inorganic materials 0.000 description 17
- 229910052740 iodine Inorganic materials 0.000 description 17
- 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 16
- 230000001976 improved effect Effects 0.000 description 15
- 239000004849 latent hardener Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 238000003860 storage Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 125000003700 epoxy group Chemical group 0.000 description 14
- 229940093915 gynecological organic acid Drugs 0.000 description 14
- 235000005985 organic acids Nutrition 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000004848 polyfunctional curative Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 10
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 9
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 230000035882 stress Effects 0.000 description 8
- 239000013008 thixotropic agent Substances 0.000 description 8
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001595 flow curve Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000011164 primary particle Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 6
- JJSYPAGPNHFLML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OC(=O)CCS.CCC(CO)(CO)CO JJSYPAGPNHFLML-UHFFFAOYSA-N 0.000 description 5
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 5
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 5
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 description 4
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 4
- 229960004068 hexachlorophene Drugs 0.000 description 4
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 4
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 4
- 229960001553 phloroglucinol Drugs 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 description 3
- MPAIWVOBMLSHQA-UHFFFAOYSA-N 3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical compound OC1=CC=C(O)C(C#N)=C1C#N MPAIWVOBMLSHQA-UHFFFAOYSA-N 0.000 description 3
- IJVBAVVYMVTACT-UHFFFAOYSA-N 4,5,7-trihydroxy-2-phenyl-4h-chromen-3-one Chemical compound O1C2=CC(O)=CC(O)=C2C(O)C(=O)C1C1=CC=CC=C1 IJVBAVVYMVTACT-UHFFFAOYSA-N 0.000 description 3
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic 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
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005837 enolization reaction Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- KAJBSGLXSREIHP-UHFFFAOYSA-N 2,2-bis[(2-sulfanylacetyl)oxymethyl]butyl 2-sulfanylacetate Chemical compound SCC(=O)OCC(CC)(COC(=O)CS)COC(=O)CS KAJBSGLXSREIHP-UHFFFAOYSA-N 0.000 description 2
- IZLVFLOBTPURLP-UHFFFAOYSA-N 2-Methoxy-4-nitrophenol Chemical compound COC1=CC([N+]([O-])=O)=CC=C1O IZLVFLOBTPURLP-UHFFFAOYSA-N 0.000 description 2
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920005672 polyolefin resin Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- ZMAMKNPVAMKIIC-UHFFFAOYSA-N (5-benzyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC=1N=C(C=2C=CC=CC=2)NC=1CC1=CC=CC=C1 ZMAMKNPVAMKIIC-UHFFFAOYSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 1
- HAQZWTGSNCDKTK-UHFFFAOYSA-N 2-(3-sulfanylpropanoyloxy)ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOC(=O)CCS HAQZWTGSNCDKTK-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- AKSVALRPYDVQBS-CABCVRRESA-N 2-[(3R)-3-[1-[1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-3-(trifluoromethyl)pyrazolo[3,4-b]pyrazin-6-yl]azetidin-3-yl]piperidin-1-yl]ethanol Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)N1CC(C1)[C@@H]1CN(CCC1)CCO)C(F)(F)F AKSVALRPYDVQBS-CABCVRRESA-N 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- 229940086681 4-aminobenzoate Drugs 0.000 description 1
- BWJHJLINOYAPEG-HOTGVXAUSA-N 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one Chemical compound ClC1=C(C(=CC=2C(N(COC=21)[C@@H]1[C@H](CCC1)O)=O)CC=1C=NC(=CC=1)Cl)C BWJHJLINOYAPEG-HOTGVXAUSA-N 0.000 description 1
- 229910002014 Aerosil® 130 Inorganic materials 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 229910002018 Aerosil® 300 Inorganic materials 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
- 239000004642 Polyimide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- STWRQBYJSPXXQE-UHFFFAOYSA-N [3,5-bis(sulfanylmethyl)phenyl]methanethiol Chemical compound SCC1=CC(CS)=CC(CS)=C1 STWRQBYJSPXXQE-UHFFFAOYSA-N 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 229940027987 antiseptic and disinfectant phenol and derivative Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 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
- 150000001559 benzoic acids Chemical class 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- RLNWRDKVJSXXPP-UHFFFAOYSA-N tert-butyl 2-[(2-bromoanilino)methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CNC1=CC=CC=C1Br RLNWRDKVJSXXPP-UHFFFAOYSA-N 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Images
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE980028 | 1998-01-16 | ||
| US9545898P | 1998-08-06 | 1998-08-06 | |
| US980028 | 1998-08-06 | ||
| US60/095,458 | 1998-08-06 | ||
| PCT/IE1999/000001 WO1999036484A1 (en) | 1998-01-16 | 1999-01-14 | Curable epoxy-based compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002509178A JP2002509178A (ja) | 2002-03-26 |
| JP2002509178A5 true JP2002509178A5 (https=) | 2008-09-18 |
| JP4394281B2 JP4394281B2 (ja) | 2010-01-06 |
Family
ID=26320151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000540193A Expired - Fee Related JP4394281B2 (ja) | 1998-01-16 | 1999-01-14 | 硬化性のエポキシ−ベースの組成物 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1047744B1 (https=) |
| JP (1) | JP4394281B2 (https=) |
| KR (1) | KR100573326B1 (https=) |
| CN (1) | CN1165592C (https=) |
| AU (1) | AU740553B2 (https=) |
| BR (1) | BR9906962A (https=) |
| CA (1) | CA2318167A1 (https=) |
| DE (1) | DE69903256T2 (https=) |
| IL (1) | IL136344A0 (https=) |
| MY (1) | MY132966A (https=) |
| TW (1) | TWI239968B (https=) |
| WO (1) | WO1999036484A1 (https=) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3868179B2 (ja) * | 1999-08-02 | 2007-01-17 | 住友ベークライト株式会社 | 液状封止樹脂組成物、半導体装置の製造方法及び半導体装置 |
| US20030082385A1 (en) * | 2001-07-13 | 2003-05-01 | Toray Composites (America), Inc. | Quick cure carbon fiber reinforced epoxy resin |
| IE20020293A1 (en) | 2002-04-23 | 2003-10-29 | Loctite R & D Ltd | Initiator systems, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
| US6818680B2 (en) * | 2002-09-23 | 2004-11-16 | Corning Incorporated | Curable adhesive compositions |
| US20040101688A1 (en) * | 2002-11-22 | 2004-05-27 | Slawomir Rubinsztajn | Curable epoxy compositions, methods and articles made therefrom |
| US7176044B2 (en) * | 2002-11-25 | 2007-02-13 | Henkel Corporation | B-stageable die attach adhesives |
| DE102004049717A1 (de) | 2004-10-11 | 2006-04-13 | Henkel Kgaa | Alterungsbeständige Beschichtungen und Klebeverbunde |
| KR100613870B1 (ko) * | 2005-05-04 | 2006-08-17 | 주식회사 덕수엔지니어링 | 흡입공기를 이용한 옥내 수도관 보수용 에폭시 수지 조성물 |
| KR101148051B1 (ko) * | 2005-12-26 | 2012-05-25 | 에스케이케미칼주식회사 | 에폭시 수지 조성물 |
| JP4938539B2 (ja) * | 2007-04-24 | 2012-05-23 | 凸版印刷株式会社 | アルカリ現像型樹脂、フォトスペーサ用感光性樹脂組成物、及びこれを用いた液晶表示装置用基板 |
| CN101418206B (zh) * | 2007-10-22 | 2012-06-20 | 财团法人工业技术研究院 | 发光二极管的封装材料组成物 |
| KR100901854B1 (ko) * | 2007-11-22 | 2009-06-09 | 이아이씨티코리아 주식회사 | 저온 경화 열경화성 에폭시 수지 조성물 및 그 제조 방법 |
| KR100951645B1 (ko) | 2007-12-28 | 2010-04-07 | (주)디피아이 홀딩스 | 저온 속경화형 에폭시 경화제, 이를 포함하는 에폭시 도료조성물 및 이를 이용한 도막의 형성 방법 |
| KR20110002023A (ko) * | 2008-03-31 | 2011-01-06 | 스미토모 베이클리트 컴퍼니 리미티드 | 수지 조성물, 수지 부착 캐리어 재료, 다층 프린트 배선판 및 반도체 장치 |
| EP2635619A1 (en) * | 2010-11-05 | 2013-09-11 | Henkel Ireland Limited | Epoxy-thiol compositions with improved stability |
| MY175088A (en) * | 2011-02-24 | 2020-06-05 | Isola Usa Corp | Ultrathin laminates |
| CN103582562B (zh) * | 2011-04-11 | 2015-10-14 | 大日本印刷株式会社 | 聚合物电解质燃料电池用增强材料及其中所使用的粘着粘接组合物 |
| WO2013053100A1 (en) * | 2011-10-11 | 2013-04-18 | Henkel China Co. Ltd. | Gel time controllable two part epoxy adhesive |
| CN104024364B (zh) * | 2011-10-11 | 2017-07-25 | 汉高股份有限及两合公司 | 可控制凝胶时间的双组份环氧粘合剂 |
| EP2792725A4 (en) | 2011-12-14 | 2015-07-29 | Mitsui Chemicals Tohcello Co Ltd | ADHESIVE COMPOSITION, LAYER BODY AND SELF-REMOVAL PROCESS |
| CN104159903B (zh) * | 2011-12-16 | 2016-06-29 | 3M创新有限公司 | 包含巯基的双失水己糖醇衍生物及其用途 |
| KR101328297B1 (ko) * | 2011-12-22 | 2013-11-14 | 삼성전기주식회사 | Ｈｄｄ 모터용 접착수지 조성물 및 이를 이용한 ｈｄｄ용 모터 |
| CN103305132B (zh) * | 2012-03-06 | 2015-03-25 | 上海佑威新材料科技有限公司 | 一种快速固化结构胶粘剂及其制备方法 |
| EP2671716A1 (en) | 2012-06-08 | 2013-12-11 | Hexcel Composites SASU | Low density composite materials, their production and use |
| JP6130502B2 (ja) | 2012-07-03 | 2017-05-17 | スリーエム イノベイティブ プロパティズ カンパニー | 構造化ハイブリッド接着剤物品の製造方法 |
| ES2704165T3 (es) * | 2013-08-12 | 2019-03-14 | Henkel Ag & Co Kgaa | Composición de respuesta mecánica |
| KR101509483B1 (ko) * | 2013-09-26 | 2015-04-08 | 주식회사 신광화학산업 | 금속과 수지의 이종 재질간 고접착력이 유지되는 이중 경화형 에폭시 접착제 조성물을 이용한 금속과 수지의 접착 방법 |
| KR102451905B1 (ko) | 2015-03-12 | 2022-10-06 | 나믹스 가부시끼가이샤 | 수지 조성물, 접착제 및 봉지제 |
| KR102720665B1 (ko) * | 2015-08-19 | 2024-10-23 | 헨켈 아게 운트 코. 카게아아 | 플럭싱 언더필 조성물 |
| WO2017077928A1 (ja) * | 2015-11-04 | 2017-05-11 | 三菱レイヨン株式会社 | 硬化性組成物、接着剤、コーティング層を有する物品、繊維強化複合材料、ポッティング剤および硬化性組成物キット |
| US11416046B2 (en) * | 2015-11-05 | 2022-08-16 | Henkel Ag & Co. Kgaa | Compositions having a matrix and encapsulated phase change materials dispersed therein, and electronic devices assembled therewith |
| JP6370327B2 (ja) * | 2016-03-30 | 2018-08-08 | 株式会社タムラ製作所 | ジェットディスペンサー用はんだ組成物 |
| US11584823B2 (en) * | 2016-12-13 | 2023-02-21 | 3M Innovative Properties Company | Epoxy stabilization using substituted barbituric acids |
| EP3583151B1 (en) * | 2017-02-15 | 2021-06-09 | 3M Innovative Properties Company | Epoxy stabilization using metal nanoparticles and nitrogen-containing catalysts, and methods |
| US20200165490A1 (en) * | 2017-06-12 | 2020-05-28 | 3M Innovative Properties Company | Epoxy/thiol resin compositions, methods, and tapes |
| KR102344683B1 (ko) | 2017-09-04 | 2021-12-30 | 삼성디스플레이 주식회사 | 표시 장치용 차폐 잉크층 및 그 제조 방법 |
| WO2019053646A1 (en) * | 2017-09-15 | 2019-03-21 | 3M Innovative Properties Company | ADHESIVE FILM COMPRISING A (METH) ACRYLATE MATRIX COMPRISING A CURABLE EPOXY / THIOL RESIN COMPOSITION, RIBBON AND METHOD |
| CN107955134B (zh) * | 2017-12-02 | 2020-05-19 | 常州宝利美石墨烯有限公司 | 一种石墨烯在环氧树脂复合材料中的应用 |
| CN107936477B (zh) * | 2017-12-02 | 2020-05-22 | 常州宝利美石墨烯有限公司 | 一种石墨烯/环氧树脂复合高分子材料 |
| CN107974043B (zh) * | 2017-12-02 | 2020-01-14 | 常州宝利美石墨烯有限公司 | 一种石墨烯/环氧树脂复合高分子材料的制备方法 |
| US20200347227A1 (en) | 2018-01-30 | 2020-11-05 | Namics Corporation | Resin composition and cured material of same, adhesive, semiconductor device, and electronic component |
| US11197246B2 (en) | 2018-08-02 | 2021-12-07 | At&T Intellectual Property I, L.P. | Power control enhancements for multi-hop integrated access and backhaul |
| CN113079699A (zh) | 2018-11-19 | 2021-07-06 | 3M创新有限公司 | 包含多硫醇、聚环氧化物、聚合物催化剂和传导填料的组合物以及与该组合物相关的方法 |
| CN113039017A (zh) | 2018-11-19 | 2021-06-25 | 3M创新有限公司 | 适合用作催化剂的包含羟基基团和叔胺基团的聚合物 |
| KR102188113B1 (ko) * | 2019-06-04 | 2020-12-07 | 전남대학교산학협력단 | 나린제닌을 포함하는 열경화성 고분자 소재 및 이의 제조방법 |
| DE102019121195A1 (de) * | 2019-08-06 | 2021-02-11 | Alzchem Trostberg Gmbh | Lagerstabile Epoxidharz-Zusammensetzung |
| WO2021033329A1 (ja) * | 2019-08-21 | 2021-02-25 | ナミックス株式会社 | エポキシ樹脂組成物 |
| KR102242440B1 (ko) * | 2019-11-25 | 2021-04-20 | 주식회사 케이씨씨 | 접착제 조성물 |
| CN112409972A (zh) * | 2020-12-02 | 2021-02-26 | 苏州瑞力博新材科技有限公司 | 一种以苯醌为稳定剂的低温快速固化单组分环氧电子胶 |
| FR3117493B1 (fr) * | 2020-12-11 | 2024-02-02 | Commissariat Energie Atomique | Résines phtalonitriles spécifiques pour applications à hautes températures et procédés de préparation de celles-ci |
| CN113088224B (zh) * | 2021-02-26 | 2022-11-29 | 广东美的白色家电技术创新中心有限公司 | 应用于封装产品的保护组合物、功率模块及其制备方法 |
| FR3139696B1 (fr) * | 2022-09-12 | 2025-10-24 | Commissariat Energie Atomique | Structure electronique flexible |
| CN117736549B (zh) * | 2024-02-02 | 2025-02-14 | 广东博汇新材料科技有限公司 | 一种高导热环氧树脂复合物的制备方法 |
| KR20260010091A (ko) * | 2024-07-12 | 2026-01-20 | 동우 화인켐 주식회사 | 전자 디바이스 밀봉용 수지 조성물 및 이를 사용하여 제조된 전자 디바이스 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6904873A (https=) * | 1968-04-29 | 1969-10-31 | ||
| JPS5657820A (en) * | 1979-10-18 | 1981-05-20 | Semedain Kk | Curable epoxy resin composition |
| JPS61159417A (ja) * | 1984-12-29 | 1986-07-19 | Semedain Kk | 硬化性エポキシ樹脂組成物 |
| JP2515344B2 (ja) * | 1987-07-24 | 1996-07-10 | 松下電工株式会社 | 封止用一液性の液状エポキシ樹脂組成物 |
| JPH0689222B2 (ja) * | 1989-11-30 | 1994-11-09 | 住友ゴム工業株式会社 | エポキシ樹脂組成物 |
| JP2558013B2 (ja) * | 1990-11-30 | 1996-11-27 | 株式会社トクヤマ | 導電性銅ペースト組成物及びその製造方法 |
| DE69318369T2 (de) * | 1992-10-22 | 1999-01-28 | Ajinomoto Co., Inc., Tokio/Tokyo | Polythiol-Epoxidharz-Mischung mit längerer Verarbeitungszeit |
-
1999
- 1999-01-14 CN CNB998021156A patent/CN1165592C/zh not_active Expired - Fee Related
- 1999-01-14 JP JP2000540193A patent/JP4394281B2/ja not_active Expired - Fee Related
- 1999-01-14 KR KR1020007007817A patent/KR100573326B1/ko not_active Expired - Fee Related
- 1999-01-14 DE DE69903256T patent/DE69903256T2/de not_active Expired - Fee Related
- 1999-01-14 CA CA002318167A patent/CA2318167A1/en not_active Abandoned
- 1999-01-14 IL IL13634499A patent/IL136344A0/xx unknown
- 1999-01-14 AU AU19811/99A patent/AU740553B2/en not_active Ceased
- 1999-01-14 BR BR9906962-8A patent/BR9906962A/pt not_active Application Discontinuation
- 1999-01-14 EP EP99900626A patent/EP1047744B1/en not_active Expired - Lifetime
- 1999-01-14 WO PCT/IE1999/000001 patent/WO1999036484A1/en not_active Ceased
- 1999-01-15 MY MYPI99000181A patent/MY132966A/en unknown
- 1999-01-16 TW TW088100665A patent/TWI239968B/zh not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4394281B2 (ja) | 硬化性のエポキシ−ベースの組成物 | |
| JP2002509178A5 (https=) | ||
| US6653371B1 (en) | One-part curable composition of polyepoxide, polythiol, latent hardener and solid organic acid | |
| KR101898742B1 (ko) | 개선된 안정성을 가지는 에폭시-티올 조성물 | |
| US6872762B2 (en) | Epoxy resin composition with solid organic acid | |
| AU728193B2 (en) | Thermosetting resin compositions useful as underfill sealants | |
| KR100556981B1 (ko) | 전자부품 | |
| DE60308545T2 (de) | Verstärktes epoxid / polyanhydrid zusammensetzung für unterfüllung ohne durchfluss | |
| KR20040088569A (ko) | Ｂ-스테이지 가공 가능한 언더필 캡슐화제 및 그의 적용방법 | |
| US6570029B2 (en) | No-flow reworkable epoxy underfills for flip-chip applications | |
| PH27200A (en) | Conductive adhesion useful for bonding a semiconductor die to a conductive support base | |
| JP2003502484A (ja) | ヘテロ原子炭素環式またはエポキシ樹脂および硬化剤の制御可能な分解性組成物 | |
| JP2005516115A (ja) | 非フローアンダーフィルカプセル封止材料 | |
| KR20010043524A (ko) | 재작업 가능한 열경화성 수지 조성물 | |
| KR20020046941A (ko) | 사용 시 발열량이 적은 새로운 고온 언더필링 물질 | |
| JP7660315B2 (ja) | 熱硬化性接着剤組成物及びその硬化物並びに接合体 | |
| JP2019085536A (ja) | 液状封止樹脂組成物、電子部品装置及び電子部品装置の製造方法 | |
| JP2017193630A (ja) | 硬化性樹脂組成物 | |
| MXPA00006955A (en) | Curable epoxy-based compositions | |
| CN119039915B (zh) | 一种具返修性的底部填充胶、其制备方法及应用 | |
| JP4690714B2 (ja) | エポキシ系硬化性組成物及び電子部品の実装構造 | |
| JP4718824B2 (ja) | エポキシ系硬化性組成物及び電子部品の製造方法 | |
| JP2007016126A (ja) | 熱硬化性樹脂組成物及び電子部品 | |
| JP5416653B2 (ja) | 電子部品 | |
| HK1058526A (en) | Thermosetting resin composition and semiconductor device obtained with the same |