JPS6230114A - エポキシおよびウレタン触媒 - Google Patents

エポキシおよびウレタン触媒

Info

Publication number: JPS6230114A
Authority: JP; Japan
Prior art keywords: catalyst; acid; epoxy; weight; compounds
Prior art date: 1985-07-31
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

Application number

JP17014185A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0586807B2 (pl

Inventor

Masatada Kurosaki

黒崎　正雅

Keiichi Nakatani

中谷　啓一

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

San Apro KK

Original Assignee

San Apro KK

Priority date (The priority date 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 date listed.)

1985-07-31

Filing date

1985-07-31

Publication date

1987-02-09

1985-07-31 Application filed by San Apro KK filed Critical San Apro KK

1985-07-31 Priority to JP17014185A priority Critical patent/JPS6230114A/ja

1987-02-09 Publication of JPS6230114A publication Critical patent/JPS6230114A/ja

1993-12-14 Publication of JPH0586807B2 publication Critical patent/JPH0586807B2/ja

Status Granted legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 33
239000004593 Epoxy Substances 0.000 title claims abstract description 13
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title description 11
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title description 6
-1 hydroxypropyl Chemical group 0.000 claims abstract description 16
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical class O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims abstract description 3
239000000126 substance Substances 0.000 claims description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
229920005989 resin Polymers 0.000 abstract description 8
239000011347 resin Substances 0.000 abstract description 8
238000010521 absorption reaction Methods 0.000 abstract description 6
238000009835 boiling Methods 0.000 abstract description 4
239000003039 volatile agent Substances 0.000 abstract 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
229920005862 polyol Polymers 0.000 description 12
150000003077 polyols Chemical class 0.000 description 11
150000001412 amines Chemical class 0.000 description 9
239000012948 isocyanate Substances 0.000 description 8
150000002513 isocyanates Chemical class 0.000 description 8
239000000203 mixture Substances 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 7
229920003986 novolac Polymers 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000003822 epoxy resin Substances 0.000 description 6
229920000647 polyepoxide Polymers 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000006260 foam Substances 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000005187 foaming Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
229920000570 polyether Polymers 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
239000007983 Tris buffer Substances 0.000 description 3
GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
239000002994 raw material Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
CFZGIDYCUWFUJR-UHFFFAOYSA-N 3-(dimethylamino)azepan-2-one Chemical compound CN(C)C1CCCCNC1=O CFZGIDYCUWFUJR-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
239000004604 Blowing Agent Substances 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
239000005058 Isophorone diisocyanate Substances 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
150000001298 alcohols 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
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
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 2
150000001718 carbodiimides Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
150000002483 hydrogen compounds Chemical class 0.000 description 2
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
DKHNRHWAVBIOGY-UHFFFAOYSA-N 2-[2-(7-oxabicyclo[4.1.0]heptane-4-carbonyloxy)ethoxy]ethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCCOCCOC(=O)C1CC2OC2CC1 DKHNRHWAVBIOGY-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-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
VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
229910001018 Cast iron Inorganic materials 0.000 description 1
239000004970 Chain extender Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002323 Silicone foam Polymers 0.000 description 1
206010040880 Skin irritation Diseases 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000002390 adhesive tape Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
230000005484 gravity Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
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 1
239000008240 homogeneous mixture Substances 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007974 melamines Chemical class 0.000 description 1
VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000010094 polymer processing Methods 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
150000008442 polyphenolic compounds Chemical class 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000013514 silicone foam Substances 0.000 description 1
230000036556 skin irritation Effects 0.000 description 1
231100000475 skin irritation Toxicity 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003890 succinate salts Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000185 sucrose group Chemical group 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
238000005829 trimerization reaction Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)
Polyurethanes Or Polyureas (AREA)
Epoxy Resins (AREA)

JP17014185A 1985-07-31 1985-07-31 エポキシおよびウレタン触媒 Granted JPS6230114A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP17014185A JPS6230114A (ja)	1985-07-31	1985-07-31	エポキシおよびウレタン触媒

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17014185A JPS6230114A (ja)	1985-07-31	1985-07-31	エポキシおよびウレタン触媒

Publications (2)

Publication Number	Publication Date
JPS6230114A true JPS6230114A (ja)	1987-02-09
JPH0586807B2 JPH0586807B2 (pl)	1993-12-14

Family

ID=15899425

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17014185A Granted JPS6230114A (ja)	1985-07-31	1985-07-31	エポキシおよびウレタン触媒

Country Status (1)

Country	Link
JP (1)	JPS6230114A (pl)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6455253A (en) *	1987-08-26	1989-03-02	Hitachi Ltd	Thermal head
JP2014189639A (ja) *	2013-03-27	2014-10-06	Dic Corp	ラミネート用２液混合接着剤組成物
WO2015046453A1 (ja) *	2013-09-30	2015-04-02	Dic株式会社	ポリイソシアネート混合物、ポリオール混合物、接着剤、及び積層フィルム
JP2020063404A (ja) *	2018-10-19	2020-04-23	日立化成株式会社	エポキシ樹脂組成物及び電子部品装置

1985
- 1985-07-31 JP JP17014185A patent/JPS6230114A/ja active Granted

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6455253A (en) *	1987-08-26	1989-03-02	Hitachi Ltd	Thermal head
JP2014189639A (ja) *	2013-03-27	2014-10-06	Dic Corp	ラミネート用２液混合接着剤組成物
WO2015046453A1 (ja) *	2013-09-30	2015-04-02	Dic株式会社	ポリイソシアネート混合物、ポリオール混合物、接着剤、及び積層フィルム
JP2020063404A (ja) *	2018-10-19	2020-04-23	日立化成株式会社	エポキシ樹脂組成物及び電子部品装置

Also Published As

Publication number	Publication date
JPH0586807B2 (pl)	1993-12-14

Publication	Publication Date	Title
US5280091A (en)	1994-01-18	Epoxy resins cured with mixed methylene bridged poly(cyclohexyl-aromatic)amine curing agents
US4658007A (en)	1987-04-14	Polyisocyanurate-based polyoxazolidone polymers and process for their preparation
US4632970A (en)	1986-12-30	Epoxy resin composition
US3717612A (en)	1973-02-20	Curable epoxy resin composition containing a substituted diurea compound
JPH0422929B2 (pl)	1992-04-20
US5373068A (en)	1994-12-13	Use of isophoronediamine isomer mixtures in polyaddition resins
US4162358A (en)	1979-07-24	Polyaromatic amine curing agents for epoxy resins
US4737564A (en)	1988-04-12	Polyphenate salts of triethylene diamine and their use in polymerizing a polyisocyanate and a polyepoxide
US4797455A (en)	1989-01-10	Isocyanates blocked with 1-amino-alkyl imidazoles as epoxy curing agents
KR102566314B1 (ko)	2023-08-14	에폭시 화합물, 이를 포함하는 에폭시 수지 조성물 및 이를 포함하는 일액형 에폭시 접착제 조성물
JPS6216484A (ja)	1987-01-24	新規アミジン，その製造法および使用法
US3547886A (en)	1970-12-15	One pot epoxy compositions containing ketimine curing agents
JPS6230114A (ja)	1987-02-09	エポキシおよびウレタン触媒
US4816533A (en)	1989-03-28	Epoxy fortifiers based on aromatic amines
US4138372A (en)	1979-02-06	Resin compositions containing polyepoxides and uretdiones
EP0722965A2 (en)	1996-07-24	Curing agents for epoxy resins
US3789071A (en)	1974-01-29	Epoxy curing agent
JPH0665184A (ja)	1994-03-08	有機ポリイソシアネートの標準化および安定化法、並びにこの方法の安定生成物
US3622540A (en)	1971-11-23	Method of curing epoxy resins using n-(aminoalkyl)-lactams or diaza-bicyclo-alkenes
US4683249A (en)	1987-07-28	Amidines and a method of manufacturing the same
US3600362A (en)	1971-08-17	Epoxy resin cured with liquid resinous amine curing agents
US3244731A (en)	1966-04-05	Glycidyl ethers
JPS63186726A (ja)	1988-08-02	常温速硬化型エポキシ樹脂組成物
US4211715A (en)	1980-07-08	Epoxy resins and process for producing the same
JPH02160768A (ja)	1990-06-20	イミダゾールエーテル化合物、製造法およびウレタン触媒

JPS6230114A - エポキシおよびウレタン触媒 - Google Patents

Info

Links

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15899425

Family Applications (1)

Country Status (1)

Cited By (4)

Cited By (4)

Also Published As

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