CN116940613A - 固化性树脂组合物、固化物及粘接剂 - Google Patents
固化性树脂组合物、固化物及粘接剂 Download PDFInfo
- Publication number
- CN116940613A CN116940613A CN202280017612.4A CN202280017612A CN116940613A CN 116940613 A CN116940613 A CN 116940613A CN 202280017612 A CN202280017612 A CN 202280017612A CN 116940613 A CN116940613 A CN 116940613A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- curable resin
- compound
- amine
- epoxy resin
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 239000000853 adhesive Substances 0.000 title claims description 8
- 230000001070 adhesive effect Effects 0.000 title claims description 8
- 239000003822 epoxy resin Substances 0.000 claims abstract description 83
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 83
- 229920005989 resin Polymers 0.000 claims abstract description 58
- 239000011347 resin Substances 0.000 claims abstract description 58
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 35
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- -1 cyanooxy groups Chemical group 0.000 claims description 62
- 150000001412 amines Chemical class 0.000 claims description 43
- 239000004593 Epoxy Substances 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 12
- 239000005011 phenolic resin Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 29
- 229920003986 novolac Polymers 0.000 description 22
- 239000000203 mixture Substances 0.000 description 17
- 238000003860 storage Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 14
- 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 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 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 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000945 filler Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- 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 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000000805 composite resin Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 239000004848 polyfunctional curative Substances 0.000 description 6
- 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 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000004844 aliphatic epoxy resin Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 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
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 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
- 230000000704 physical effect Effects 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- POFFJVRXOKDESI-UHFFFAOYSA-N 1,3,5,7-tetraoxa-4-silaspiro[3.3]heptane-2,6-dione Chemical compound O1C(=O)O[Si]21OC(=O)O2 POFFJVRXOKDESI-UHFFFAOYSA-N 0.000 description 2
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 2
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 2
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- TYAHIHMYMVZOEC-UHFFFAOYSA-N 2-[2-(2-hydroxyphenyl)ethyl]phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1O TYAHIHMYMVZOEC-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- VEGUCZXWLYWJFN-UHFFFAOYSA-N 3-[(3-hydroxy-2-methylphenyl)methyl]-2-methylphenol Chemical compound CC1=C(O)C=CC=C1CC1=CC=CC(O)=C1C VEGUCZXWLYWJFN-UHFFFAOYSA-N 0.000 description 2
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- BLJDJVLDTYVWCL-UHFFFAOYSA-N CC1CC2OC2CC1CC1(C(O)=O)CCCCC1C Chemical compound CC1CC2OC2CC1CC1(C(O)=O)CCCCC1C BLJDJVLDTYVWCL-UHFFFAOYSA-N 0.000 description 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 2
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 2
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910002026 crystalline silica Inorganic materials 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 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 2
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 2
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052839 forsterite Inorganic materials 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 229910052863 mullite Inorganic materials 0.000 description 2
- 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 2
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 2
- HATIEXJZXOLRAO-UHFFFAOYSA-N octanedihydrazide Chemical compound NNC(=O)CCCCCCC(=O)NN HATIEXJZXOLRAO-UHFFFAOYSA-N 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
- 229960001553 phloroglucinol Drugs 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 229910052596 spinel Inorganic materials 0.000 description 2
- 239000011029 spinel Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 2
- 229910052845 zircon Inorganic materials 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- QFBYLLSKEFKNFO-UHFFFAOYSA-N 1,3-dimethylurea 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane Chemical compound CNC(=O)NC.CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 QFBYLLSKEFKNFO-UHFFFAOYSA-N 0.000 description 1
- ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical compound C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 description 1
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- TXDNYIHPVKNPRJ-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)propan-2-amine Chemical compound CC(N)CC1=NC=CN1 TXDNYIHPVKNPRJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- JGYUBHGXADMAQU-UHFFFAOYSA-N 2,4,6-triethylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(CC)=C1N JGYUBHGXADMAQU-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
- VRRDONHGWVSGFH-UHFFFAOYSA-N 2,5-diethylcyclohexane-1,4-diamine Chemical compound CCC1CC(N)C(CC)CC1N VRRDONHGWVSGFH-UHFFFAOYSA-N 0.000 description 1
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 1
- GOWUDHPKGOIDIX-UHFFFAOYSA-N 2-(4-methyl-1-piperazinyl)ethanamine Chemical compound CN1CCN(CCN)CC1 GOWUDHPKGOIDIX-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- MGDCPRXEOXKHBI-UHFFFAOYSA-N 2-ethyl-1,1-di(propan-2-yl)hydrazine Chemical compound CCNN(C(C)C)C(C)C MGDCPRXEOXKHBI-UHFFFAOYSA-N 0.000 description 1
- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-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
- OBCYIOKCFVYJCH-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-ylmethoxy)-N-(oxiran-2-ylmethyl)aniline Chemical compound C(C1CO1)NC1=C(C=C(C=C1)OCC1CO1)C OBCYIOKCFVYJCH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 1
- JQURSUCXJUAFGZ-UHFFFAOYSA-N 2-n-ethyl-1-n,1-n-dimethylpropane-1,2-diamine Chemical compound CCNC(C)CN(C)C JQURSUCXJUAFGZ-UHFFFAOYSA-N 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-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
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-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
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-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
- VCADDYHLOZODRM-UHFFFAOYSA-N 3-N-cyclohexylpropane-1,1,3-triamine Chemical compound C1CCC(CC1)NCCC(N)N VCADDYHLOZODRM-UHFFFAOYSA-N 0.000 description 1
- IMQGETBDLVKFTF-UHFFFAOYSA-N 3-N-hexylpropane-1,1,3-triamine Chemical compound CCCCCCNCCC(N)N IMQGETBDLVKFTF-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- YOCQWEYKTWXMRR-UHFFFAOYSA-N 3-n-ethylpropane-1,1,3-triamine Chemical compound CCNCCC(N)N YOCQWEYKTWXMRR-UHFFFAOYSA-N 0.000 description 1
- BXLDDFPJPFKVON-UHFFFAOYSA-N 3-n-methylpropane-1,1,3-triamine Chemical compound CNCCC(N)N BXLDDFPJPFKVON-UHFFFAOYSA-N 0.000 description 1
- KHURTEAYLZEQHD-UHFFFAOYSA-N 3-n-propylpropane-1,1,3-triamine Chemical compound CCCNCCC(N)N KHURTEAYLZEQHD-UHFFFAOYSA-N 0.000 description 1
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 description 1
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 description 1
- VPBWZBGZWHDNKL-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCC1 VPBWZBGZWHDNKL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 description 1
- JCGWKDDAKPGTJK-UHFFFAOYSA-N 4-(4-aminocyclohexyl)sulfonylcyclohexan-1-amine Chemical compound C1CC(N)CCC1S(=O)(=O)C1CCC(N)CC1 JCGWKDDAKPGTJK-UHFFFAOYSA-N 0.000 description 1
- HWJBORCEJISUFD-UHFFFAOYSA-N 4-(aminomethyl)-n,n-di(propan-2-yl)aniline Chemical compound CC(C)N(C(C)C)C1=CC=C(CN)C=C1 HWJBORCEJISUFD-UHFFFAOYSA-N 0.000 description 1
- LBSZDWUTQGRQKH-UHFFFAOYSA-N 4-(aminomethyl)-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=C(CN)C=C1 LBSZDWUTQGRQKH-UHFFFAOYSA-N 0.000 description 1
- PDJZOFLRRJQYBF-UHFFFAOYSA-N 4-(aminomethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(CN)C=C1 PDJZOFLRRJQYBF-UHFFFAOYSA-N 0.000 description 1
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
- YSPYOLWYCQXPOC-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC(C=C1)=CC=C1OCC1CO1 YSPYOLWYCQXPOC-UHFFFAOYSA-N 0.000 description 1
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PHEWJNYBXNAWFW-UHFFFAOYSA-N C(=O)(NC)NC.CC=1C(N=C=O)=CC(N=C=O)=CC1 Chemical compound C(=O)(NC)NC.CC=1C(N=C=O)=CC(N=C=O)=CC1 PHEWJNYBXNAWFW-UHFFFAOYSA-N 0.000 description 1
- YUEDZVRMWQBEPT-UHFFFAOYSA-N CC1=CC=CC(C(C2=CC=CC=C2)C2=CC=CC=C2)=C1C.N=C=O.N=C=O.N=C=O.N=C=O Chemical compound CC1=CC=CC(C(C2=CC=CC=C2)C2=CC=CC=C2)=C1C.N=C=O.N=C=O.N=C=O.N=C=O YUEDZVRMWQBEPT-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 235000003332 Ilex aquifolium Nutrition 0.000 description 1
- 235000002296 Ilex sandwicensis Nutrition 0.000 description 1
- 235000002294 Ilex volkensiana Nutrition 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- AFOHEWVKCWGQRW-UHFFFAOYSA-N N,N-bis(cyclohexylamino)ethanamine Chemical compound C1(CCCCC1)NN(NC1CCCCC1)CC AFOHEWVKCWGQRW-UHFFFAOYSA-N 0.000 description 1
- OJNIPMQYTNCVEN-UHFFFAOYSA-N N,N-bis(cyclohexylamino)propan-1-amine Chemical compound C1(CCCCC1)NN(NC1CCCCC1)CCC OJNIPMQYTNCVEN-UHFFFAOYSA-N 0.000 description 1
- YHTLECILBKQOIL-UHFFFAOYSA-N N-(benzylamino)-N-[benzyl(ethyl)amino]propan-1-amine Chemical compound C(C)N(N(NCC1=CC=CC=C1)CCC)CC1=CC=CC=C1 YHTLECILBKQOIL-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- WKZLMKPZIRKQHC-UHFFFAOYSA-N NC(CCNCCCC)N Chemical compound NC(CCNCCCC)N WKZLMKPZIRKQHC-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 239000004163 Spermaceti wax Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 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
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940092738 beeswax Drugs 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000011083 cement mortar Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-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
- 230000000694 effects Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- QPGRDTXELAFGRG-UHFFFAOYSA-N n',n'-di(propan-2-yl)propane-1,3-diamine Chemical compound CC(C)N(C(C)C)CCCN QPGRDTXELAFGRG-UHFFFAOYSA-N 0.000 description 1
- KXBUDXGDASOGBX-UHFFFAOYSA-N n',n'-dibenzylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1CN(CCCN)CC1=CC=CC=C1 KXBUDXGDASOGBX-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 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
- YFQPICDSUBYACX-UHFFFAOYSA-N n'-(2-phenylethyl)propane-1,3-diamine Chemical compound NCCCNCCC1=CC=CC=C1 YFQPICDSUBYACX-UHFFFAOYSA-N 0.000 description 1
- HUWUUMUEMQWJKZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-benzylpropane-1,3-diamine Chemical compound NCCCN(CCCN)CC1=CC=CC=C1 HUWUUMUEMQWJKZ-UHFFFAOYSA-N 0.000 description 1
- LUZCQJHUWNIZNZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-pentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCN LUZCQJHUWNIZNZ-UHFFFAOYSA-N 0.000 description 1
- IZDWJSKWDHFHSF-UHFFFAOYSA-N n'-(cyclohexylmethyl)propane-1,3-diamine Chemical compound NCCCNCC1CCCCC1 IZDWJSKWDHFHSF-UHFFFAOYSA-N 0.000 description 1
- HUQLOABSMDKQBW-UHFFFAOYSA-N n'-benzyl-n-methylethane-1,2-diamine Chemical compound CNCCNCC1=CC=CC=C1 HUQLOABSMDKQBW-UHFFFAOYSA-N 0.000 description 1
- IWUHWRSKHTWKHZ-UHFFFAOYSA-N n'-cyclohexyl-n-methylethane-1,2-diamine Chemical compound CNCCNC1CCCCC1 IWUHWRSKHTWKHZ-UHFFFAOYSA-N 0.000 description 1
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- LIBWSLLLJZULCP-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC=C1 LIBWSLLLJZULCP-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- WLNSKTSWPYTNLY-UHFFFAOYSA-N n-ethyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCNCCN(C)C WLNSKTSWPYTNLY-UHFFFAOYSA-N 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000779 poly(divinylbenzene) Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019385 spermaceti wax Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- NACZPBOVCXPUJN-UHFFFAOYSA-N tris-decyl(methyl)azanium Chemical compound CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC NACZPBOVCXPUJN-UHFFFAOYSA-N 0.000 description 1
- UMMDBKGUDMBUSR-UHFFFAOYSA-M tris-decyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC UMMDBKGUDMBUSR-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3227—Compounds containing acyclic nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/34—Epoxy compounds containing three or more epoxy groups obtained by epoxidation of an unsaturated polymer
-
- 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
- C08G59/5006—Amines aliphatic
- C08G59/502—Polyalkylene polyamines
-
- 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
- C08G59/56—Amines together with other curing agents
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- 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
- C09J163/08—Epoxidised polymerised polyenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
Abstract
一种固化性树脂组合物,其含有(A)氰酸酯树脂、(B)至少以4‑氨基‑3‑甲基苯酚型环氧树脂作为必须的环氧树脂及(C)潜在性固化剂。(A)氰酸酯树脂优选为选自由下述式(1)所表示的化合物及下述式(2)所表示的化合物、以及选自它们中的至少1种的聚合物构成的组中的1种以上。NC‑O‑A1‑Y1‑A2‑O‑CN(1)(式中的符号参照说明书。)(2)(式中的符号参照说明书。)
Description
技术领域
本发明涉及固化性树脂组合物,详细而言,涉及含有氰酸酯树脂、特定的环氧树脂及潜在性固化剂的固化性树脂组合物。
背景技术
环氧树脂作为涂料、粘接剂、构成各种成形材料的成分或原料在工业上被广泛使用。
进而,仅将现有的环氧树脂单独或多种混合使用的情况下耐热性等不充分的情况等中,将环氧树脂与氰酸酯树脂混合而成的氰酸酯-环氧复合树脂组合物由于为高耐热性,因此经常作为有用的材料被使用。
例如,已经提出了包含氰酸酯树脂、环氧树脂、无机填充剂、金属螯合物、二酰肼化合物等的半导体密封用液状环氧树脂组合物(专利文献1),但该情况下,为了使其固化,需要在高温下长时间进行加热等,不能得到可令人满意的性能。
此外,还提出了在包含氰酸酯树脂及环氧树脂的复合组合物中使用胺系固化剂的例子(专利文献2),但该情况下未得到充分的贮藏稳定性。
进而,还提出了在氰酸酯树脂及环氧树脂中使用了包含咪唑成分的潜在性固化剂的热固性树脂组合物(专利文献3),但该情况下,从得到充分的贮藏稳定性的观点出发,氰酸酯树脂的使用量受到限制等,未得到可令人满意的组合物。
进而,还提出了在氰酸酯树脂及环氧树脂中将胍化合物与酚类化合物组合使用的复合树脂组合物(专利文献4),但耐热性不能够充分令人满意。
进而,还提出了相对于官能团数多的氰酸酯树脂及环氧树脂的组合组合胺系潜在性固化剂而得到的复合树脂组合物(专利文献5),但该情况下,贮藏稳定性不能够充分令人满意。
另一方面,在专利文献6~8等中,记载了本发明中使用的4-氨基-3-甲基苯酚型环氧树脂,但未记载将其与氰酸酯树脂组合使用。
现有技术文献
专利文献
专利文献1:美国专利第6469074号说明书
专利文献2:日本特开昭60-250026号公报
专利文献3:美国专利申请公开第2002/058778号说明书
专利文献4:美国专利申请公开第2012/178853号说明书
专利文献5:美国专利申请公开第2012/309923号说明书
专利文献6:美国专利申请公开第2009/311827号说明书
专利文献7:日本特开2009-158712号公报
专利文献8:日本特开2009-155450号公报
发明内容
如上所述,专利文献1~5中记载的氰酸酯-环氧复合树脂组合物关于贮藏稳定性与耐热性的兼顾不充分。
此外,获知在氰酸酯-环氧复合树脂组合物中,作为环氧树脂,通过使用4-氨基苯酚型环氧树脂,可得到低粘度且高物性的固化物。然而,本发明人们的进一步研究的结果判定:在氰酸酯-环氧复合树脂组合物中,作为环氧树脂,在使用4-氨基苯酚型环氧树脂的情况下,在贮藏稳定性的方面存在改善的余地。
因此,本发明所要解决的课题是提供贮藏稳定性优异、并且固化物的耐热性优异的固化性树脂组合物。
于是,本发明人等进行深入研究,发现含有氰酸酯树脂、特定的环氧树脂及潜在性固化剂的固化性树脂组合物可达成上述目的,从而达成了本发明。
即,本发明提供一种固化性树脂组合物,其含有(A)氰酸酯树脂、(B)以4-氨基-3-甲基苯酚型环氧树脂作为必须的环氧树脂及(C)潜在性固化剂。
此外本发明提供上述固化性树脂组合物的固化物及包含上述固化性树脂组合物的粘接剂。
具体实施方式
以下,对本发明的固化性树脂组合物基于其优选的实施方式进行说明。
作为本发明中使用的(A)成分即氰酸酯树脂,为具有2个以上氰酸酯基的化合物,可以对分子结构、分子量等没有特别限制地使用。
作为上述(A)成分即氰酸酯树脂,例如可以使用选自由下述式(1)所表示的化合物、下述式(2)所表示的化合物及它们中的至少1种的聚合物构成的组中的1种以上。
NC-O-A1-Y1-A2-O-CN(1)
(式中,Y1表示非取代或被氟原子或氰氧基取代的2价烃基、或者表示-O-、-S-、或单键,A1及A2分别独立地为非取代或被1~4个烷基取代的亚苯基。)
[化学式1]
(式中,m为1以上的整数,Y2及Y3分别独立地表示-S-、或者表示非取代或被氟原子或氰氧基取代的2价烃基。R1、R2、R3、R4、R5及R6分别独立地为氢原子或碳数1~4的烷基。)
本说明书中,作为碳数1~4的烷基,例如可列举出甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基。
作为上述式(1)中的Y1以及上述式(2)中的Y2及Y3所表示的非取代或被氟原子取代的2价烃基,可适宜列举出碳原子数1~20的烃基。作为上述式(1)中的Y1或上述式(2)中的Y2及Y3,优选为具有下述式(Y-1)~(Y-9)中的任一者所表示的结构的烃基。
[化学式2]
(其中,n为4~12的整数,R7及R8分别独立地为氢原子或非取代或被氟原子取代的甲基。此外,*表示键合点。)
示出上述具体例子的氰酸酯树脂中,使用上述式(1)所表示的化合物由于固化性、固化后的平衡良好,因此优选。
进而,从得到耐热性进一步优异的固化物的理由出发,可列举出上述氰酸酯树脂中双酚E型的氰酸酯树脂、联苯型、酚醛清漆苯酚(novolak phenol)型、双酚A型等氰酸酯树脂作为优选的例子,其中,优选使用双酚E型的氰酸酯树脂。作为双酚E型或双酚A型等双酚型的氰酸酯树脂,可列举出上述式(1)中Y1以(Y-1)表示的树脂。作为联苯型的氰酸酯树脂,可列举出上述式(1)中Y1为单键的树脂。作为酚醛清漆苯酚型的氰酸酯树脂,可列举出上述式(2)中Y2及Y3分别独立地为(Y-1)的树脂。
进而,从得到耐热性进一步优异的固化物的理由出发,在使用双酚型、联苯型或酚醛清漆苯酚型的氰酸酯树脂的情况下,优选在氰酸酯树脂整体中双酚型、联苯型或酚醛清漆苯酚型的氰酸酯树脂占80质量%以上,更优选双酚型、联苯型或酚醛清漆苯酚型的氰酸酯树脂占90质量%以上。特别是本发明中,优选在氰酸酯树脂整体中双酚型氰酸酯树脂占80质量%以上,更优选双酚型氰酸酯树脂占90质量%以上,特别优选双酚型氰酸酯树脂占95质量%以上。
作为氰酸酯树脂的含量,从固化性与贮藏稳定性的平衡特别优异的观点出发,在组合物的固体成分100质量份中,更优选为3质量份以上且80质量份以下,特别优选为7质量份以上且60质量份以下。需要说明的是,固体成分是指除溶剂以外的全部成分的合计量。在本固化性树脂组合物中,可以含有溶剂,也可以不含有溶剂,但在含有的情况下,在固化性树脂组合物中5质量%以下适宜,2质量%以下更适宜。
本发明中使用的(B)环氧树脂是包含4-氨基-3-甲基苯酚型环氧树脂作为必须成分的环氧树脂。本发明人进行了研究,结果判定:如后述的比较例1中所示的那样,在将4-氨基苯酚型环氧树脂与氰酸酯树脂组合使用的情况下,在贮藏稳定性的方面存在改善的余地。另一方面,4-氨基苯酚型环氧树脂与4-氨基-3-甲基苯酚型环氧树脂尽管结构类似,但通过将4-氨基-3-甲基苯酚型环氧树脂与氰酸酯树脂组合,得到显著提高贮藏稳定性这样的以往预料之外的显著的效果。
上述4-氨基-3-甲基苯酚型环氧树脂是以4-氨基-3-甲基苯酚作为起始原料的环氧树脂,对其制造方法没有特别限定,但例如可以通过使4-氨基-3-甲基-苯酚与环氧卤丙烷在碱的存在下反应来制造。
作为上述环氧卤丙烷,例如可列举出环氧氯丙烷、环氧溴丙烷、β-甲基环氧氯丙烷、β-甲基环氧溴丙烷等。它们中,从相对于羟基及氨基的反应性良好的方面出发,优选环氧氯丙烷。此外,上述环氧卤丙烷可以单独使用,也可以将2种以上并用。作为上述碱,例如可列举出氢氧化钠、氢氧化钾等碱金属氢氧化物、碳酸钠、碳酸钾等碱金属碳酸盐等,这些碱中,特别优选氢氧化钠。优选将这些碱制成水溶液来使用,但根据情况,也可以将粉末或固形的碱与水同时或分别添加。
上述4-氨基-3-甲基苯酚和环氧卤丙烷的使用比率只要相对于前者的羟基及氨基为当量以上则没有特别限制,但通常为1.0~10.0当量,特别优选为2.0~8.0当量的范围。这里所谓的相对于4-氨基-3-甲基苯酚的羟基及氨基的当量是通过环氧卤丙烷的摩尔数除以“羟基的摩尔数+(氨基的摩尔数)×2”而得到的值。若上述环氧卤丙烷的比率低于1.0当量(等当量),则有时未被缩水甘油醚化的羟基、氨基残存而纯度降低。此外,在超过10.0当量的情况下不仅环氧氯丙烷变得徒劳,而且有时反应速度降低或因副反应而环氧当量变大。
此外,上述碱的使用量只要相对于上述4-氨基-3-甲基苯酚的羟基及氨基为当量(摩尔)以上则不会特别受到限制,但通常为1.0~2.0当量,特别优选为1.0~1.5当量的范围。若碱的使用量相对于4-氨基-3-甲基苯酚的羟基低于当量,则有时未被缩水甘油醚化的氯醇醚基残存而纯度降低。此外,即使超过2.0当量,也不仅变得徒劳,而且有时因副反应而制品的纯度降低。
此外,在上述反应中,也可以使用相转移催化剂,该相转移催化剂作为为了使在水中为不溶性的有机化合物与在有机溶剂中为不溶性的试剂反应而使用的试剂而已知。作为上述相转移催化剂,可列举出三甲基胺、三辛基胺、三癸基胺那样的叔胺、四甲基铵、甲基三辛基铵、甲基三癸基铵、苄基三甲基铵那样的季铵盐基、四甲基氯化铵、甲基三辛基氯化铵、甲基三癸基氯化铵、苄基三甲基氯化铵那样的季铵盐,特别优选季铵盐。
上述相转移催化剂的使用量为适宜使用确定的量,但相对于4-氨基-3-甲基苯酚100质量份,通常为0.1~10.0质量份,优选为0.5~5.0质量份的范围。若相转移催化剂的使用量低于0.1质量份,则反应速度显著变慢或副反应进行而环氧当量变小,因此并不实用,此外,即使超过10.0质量份,相转移催化剂也变得徒劳,而且根据情况有时会阻碍反应。
此外,上述的反应通常在加热下进行,优选30℃~100℃,特别优选在40℃~80℃下进行。此外,在反应时,也可以使用烃、醚或酮那样的对反应为惰性的溶剂,但在过量使用环氧卤丙烷的情况下,环氧卤丙烷也作为溶剂发挥功能,因此使用上述那样的对反应为惰性的溶剂不是必须的。
本发明中所谓的4-氨基-3-甲基苯酚型环氧树脂可列举出下述式(I)的结构的化合物。
[化学式3]
本发明中使用的(B)成分的环氧树脂可以使用上述4-氨基-3-甲基苯酚型环氧树脂以外的环氧树脂,该环氧树脂是在分子中具有至少2个环氧基的树脂,可以对分子结构、分子量等没有特别限制地使用。
作为上述环氧树脂,可列举出氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的聚缩水甘油醚化合物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺基双酚、氧代双酚、苯酚酚醛清漆(phenol novolak)、邻甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的聚缩水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫甘醇、二环戊二烯二甲醇、2,2-双(4-羟基环己基)丙烷(氢化双酚A)、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇、双酚A-环氧烷烃加成物等多元醇化合物的聚缩水甘油醚化合物;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯化合物及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)-2-甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)苯胺、N,N,N’,N’-四(2,3-环氧丙基)-4,4-二氨基二苯基甲烷等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯、环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物;异氰脲酸三缩水甘油酯等杂环化合物。此外,这些环氧树脂也可以为通过末端异氰酸酯的预聚物而内部交联的环氧树脂、或以多价的活性氢化合物(多元酚、多胺、含羰基化合物、多磷酸酯等)高分子量化的环氧树脂。
这些环氧树脂可以单独使用,也可以将2种以上并用来使用。
本发明的组合物中的环氧树脂中,上述4-氨基-3-甲基苯酚型环氧树脂优选为20~100质量%,更优选为25~70质量%。通过使用20质量%以上,可得到耐热性特别优异的固化物。
此外,本发明的组合物中的环氧树脂中,作为上述4-氨基-3-甲基苯酚型环氧树脂以外的环氧树脂,从反应性的观点出发,优选含有具有缩水甘油基的缩水甘油基型环氧树脂,尤其是从耐热性的方面出发,优选含有具有芳香族环的缩水甘油基型环氧树脂。在环氧树脂除了含有4-氨基-3-甲基苯酚型环氧树脂以外还含有具有芳香族环的缩水甘油基型环氧树脂作为环氧树脂的情况下,从确保4-氨基-3-甲基苯酚型环氧树脂的量的方面及耐热性的方面出发,其量在环氧树脂整体中优选为1质量%~80质量%,特别优选为15质量%~75质量%。作为4-氨基-3-甲基苯酚型环氧树脂以外的具有芳香族环的缩水甘油基型环氧树脂,使用多核多元酚化合物的聚缩水甘油醚化合物从耐热性的方面出发特别优选。此外,通过并用脂肪族环氧树脂,可谋求组合物的低粘度化,因此优选。作为环氧树脂,除了4-氨基-3-甲基苯酚型环氧树脂以外,还使用脂肪族环氧树脂作为环氧树脂的情况下,从确保4-氨基-3-甲基苯酚型环氧树脂的量的方面及低粘度化的方面出发,其量在环氧树脂整体中优选为1质量%~70质量%,特别优选为5质量%~50质量%。作为脂肪族环氧树脂的例子,可列举出二环戊二烯型环氧树脂。二环戊二烯型环氧树脂是指具有二环戊二烯骨架、且具有环氧基的化合物。作为二环戊二烯型环氧树脂,优选脂肪族化合物。在本发明的环氧树脂含有二环戊二烯型环氧树脂作为上述脂肪族环氧树脂的情况下,从与上述同样的观点出发,其量在环氧树脂整体中优选为1质量%~70质量%,特别优选为5质量%~50质量%。
上述(B)成分即环氧树脂的使用量相对于上述(A)成分即氰酸酯树脂100质量份,优选为1~1000质量份,更优选为3~500质量份,为5~200质量份由于可得到优异的固化物物性,因此更优选。
进而,上述4-氨基-3-甲基苯酚型环氧树脂的使用量相对于上述(A)成分即氰酸酯树脂100质量份,优选为1~200质量份,通过在该范围内使用,可得到耐热性优异的树脂组合物,因此优选,优选为5~150质量份,更优选为10~100质量份。
作为本发明中使用的(C)成分即潜在性固化剂,通过使用具有活性氢的胺系潜在性固化剂(以下,也称为“含活性氢的胺系潜在性固化剂”。),可获得得到了贮藏稳定性与固化性的平衡的固化性树脂,因此优选。
作为含活性氢的胺系潜在性固化剂,例如可列举出草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼、邻苯二甲酸二酰肼等二元酸二酰肼;双氰胺、苯并胍胺、乙酰胍胺等胍化合物;三聚氰胺;胺与羧酸的脱水缩合物、胺与环氧的加成物、胺与异氰酸酯的加成物、胺的麦克尔加成物、胺的曼尼希反应物、胺与尿素的缩合物、胺与酮的缩合物等改性胺等。
上述含活性氢的胺系潜在性固化剂中,可列举出选自双氰胺、苯并胍胺、乙酰胍胺等胍化合物;或(C-1)使具有1个以上活性氢的胺化合物及环氧化合物反应而成的改性胺、(C-2)使具有1个以上活性氢的胺化合物及异氰酸酯化合物反应而成的改性胺及(C-3)使具有1个以上活性氢的胺化合物、环氧化合物及异氰酸酯化合物反应而成的改性胺、以及(C-4)除了含有选自(C-1)、(C-2)或(C-3)中的至少一种改性胺以外还含有酚醛树脂而成的潜在性固化剂中的至少一种作为优选的例子。
作为上述具有1个以上活性氢的胺化合物,例如可列举出乙二胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,3-二氨基丁烷、1,4-二氨基丁烷、六亚甲基二胺等亚烷基二胺类;二亚乙基三胺、三亚乙基三胺、四亚乙基五胺等多烷基多胺类;1,4-二氨基环己烷、1,3-二氨基环己烷、1,3-二氨基甲基环己烷、1,2-二氨基环己烷、1,4-二氨基-3,6-二乙基环己烷、4,4’-二氨基二环己基甲烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、4,4’-二氨基二环己基丙烷、双(4-氨基环己基)砜、4,4’-二氨基二环己基醚、2,2’-二甲基-4,4’-二氨基二环己基甲烷、异佛尔酮二胺、降冰片烯二胺等脂环式多胺类;间苯二甲基二胺、二氨基二苯基甲烷、二氨基二苯基砜、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二氨基苯、1-甲基-3,5-二乙基-2,6-二氨基苯、1,3,5-三乙基-2,6-二氨基苯、3,3’-二乙基-4,4’-二氨基二苯基甲烷、3,5,3’、5’-四甲基-4,4’-二氨基二苯基甲烷等芳香族多胺类;苯并胍胺、乙酰胍胺等胍胺类;2-甲基咪唑、2-乙基-4-甲基咪唑、2-异丙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、2-氨基丙基咪唑等咪唑类;草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼、邻苯二甲酸二酰肼等二酰肼类;N,N-二甲基氨基乙基胺、N,N-二乙基氨基乙基胺、N,N-二异丙基氨基乙基胺、N,N-二烯丙基氨基乙基胺、N,N-苄基甲基氨基乙基胺、N,N-二苄基氨基乙基胺、N,N-环己基甲基氨基乙基胺、N,N-二环己基氨基乙基胺、N-(2-氨基乙基)吡咯烷、N-(2-氨基乙基)哌啶、N-(2-氨基乙基)吗啉、N-(2-氨基乙基)哌嗪、N-(2-氨基乙基)-N’-甲基哌嗪、N,N-二甲基氨基丙基胺、N,N-二乙基氨基丙基胺、N,N-二异丙基氨基丙基胺、N,N-二烯丙基氨基丙基胺、N,N-苄基甲基氨基丙基胺、N,N-二苄基氨基丙基胺、N,N-环己基甲基氨基丙基胺、N,N-二环己基氨基丙基胺、N-(3-氨基丙基)吡咯烷、N-(3-氨基丙基)哌啶、N-(3-氨基丙基)吗啉、N-(3-氨基丙基)哌嗪、N-(3-氨基丙基)-N’-甲基哌啶、4-(N,N-二甲基氨基)苄基胺、4-(N,N-二乙基氨基)苄基胺、4-(N,N-二异丙基氨基)苄基胺、N,N-二甲基异佛尔酮二胺、N,N-二甲基双氨基环己烷、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基乙二胺、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基丙二胺、N’-乙基-N,N-二苄基氨基丙基胺;N,N-(双氨基丙基)-N-甲基胺、N,N-双氨基丙基乙基胺、N,N-双氨基丙基丙基胺、N,N-双氨基丙基丁基胺、N,N-双氨基丙基戊基胺、N,N-双氨基丙基己基胺、N,N-双氨基丙基-2-乙基己基胺、N,N-双氨基丙基环己基胺、N,N-双氨基丙基苄基胺、N,N-双氨基丙基烯丙基胺、双〔3-(N,N-二甲基氨基丙基)〕胺、双〔3-(N,N-二乙基氨基丙基)〕胺、双〔3-(N,N-二异丙基氨基丙基)〕胺、双〔3-(N,N-二丁基氨基丙基)〕胺等。
作为上述环氧化合物,例如可列举出氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的聚缩水甘油醚化合物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺酰基双酚、氧代双酚、苯酚酚醛清漆(phenol novolak)、邻甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的聚缩水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、硫代二甘醇、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇、双酚A-环氧烷烃加成物等多元醇类的聚缩水甘油醚;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸、桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯类及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、二环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯、环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物、异氰脲酸三缩水甘油酯等杂环化合物。
环氧化合物可以为缩水甘油基型环氧化合物及以环状烯烃化合物的环氧化物为代表的氧化环烯烃型的环氧化合物中的任一者。此外在为缩水甘油基型的情况下,可以为具有芳香族环的芳香族环氧化合物及不具有芳香族环的脂肪族环氧化合物中的任一者。优选的是:从反应性的方面出发,作为环氧化合物,优选使用缩水甘油基型的环氧化合物,从耐热性的方面出发,更优选使用缩水甘油基型的芳香族环氧化合物。
作为上述异氰酸酯化合物,例如可列举出2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、二苯基甲烷-4,4‘-二异氰酸酯、苯二异氰酸酯、苯二甲基二异氰酸酯、四甲基苯二甲基二异氰酸酯、1,5-萘二异氰酸酯、1,5-四氢萘二异氰酸酯、3,3’-二甲基二苯基-4,4‘-二异氰酸酯、二茴香胺二异氰酸酯、四甲基苯二甲基二异氰酸酯等芳香族二异氰酸酯;异佛尔酮二异氰酸酯、二环己基甲烷-4,4’-二异氰酸酯、反式-1,4-环己基二异氰酸酯、降冰片烯二异氰酸酯等脂环式二异氰酸酯;四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、2,2,4和/或(2,4,4)-三甲基六亚甲基二异氰酸酯、赖氨酸二异氰酸酯等脂肪族二异氰酸酯;上述例示的二异氰酸酯的异氰脲酸酯三聚物、缩二脲三聚物、三羟甲基丙烷加成物等;三苯基甲烷三异氰酸酯、1-甲基苯-2,4,6-三异氰酸酯、二甲基三苯基甲烷四异氰酸酯等。
进而,这些异氰酸酯化合物也可以以碳二亚胺改性、异氰脲酸酯改性、缩二脲改性等形式使用,也可以以通过各种封端剂而封端的封端异氰酸酯的形式使用。
这里,在作为(C-1)的改性胺中,具有1个以上活性氢的胺化合物和环氧化合物的使用量优选相对于胺化合物的活性氢1当量,使环氧化合物的环氧基成为0.1~1.1当量的量、特别是成为0.2~1.0当量的量反应。
此外,在作为(C-2)的改性胺中,具有1个以上活性氢的胺化合物和异氰酸酯化合物的使用量优选相对于胺化合物的活性氢1当量,使异氰酸酯化合物的异氰酸酯基成为0.1~1.1当量的量、特别是成为0.2~1.0当量的量反应。
进而,在作为(C-3)的改性胺中,具有1个以上活性氢的胺化合物、作为(C-2)的环氧化合物及作为(C-3)的异氰酸酯化合物的使用量优选相对于胺化合物的活性氢1当量,使环氧化合物的环氧基及聚异氰酸酯化合物的异氰酸酯基的合计量成为0.1~1.1当量的量、特别是成为0.2~1.0当量的量反应。
这里,通过将环氧化合物和/或异氰酸酯化合物相对于具有1个以上活性氢的胺化合物的量设定为上述下限值以上,能够提高固化性树脂组合物的保存稳定性,因此优选,通过设定为上述上限值以下,能够可靠地获得固化性,因此优选。
特别是这些改性胺使用含有活性氢基时由于固化性、固化物性优异,因此优选。
上述作为(C-1)、(C-2)及(C-3)的改性胺的制造方法没有特别限定,但通过根据需要使用溶剂,在常温~140℃的加热下进行1~10小时反应,可得到改性胺。
在(C-3)改性胺中,通常优选使胺化合物与环氧化合物反应后使聚异氰酸酯化合物反应。
在使用溶剂的情况下,也可以在反应结束后将溶剂在加热下通过常压或减压而除去。
作为上述改性胺的制造中使用的上述溶剂,可列举出甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、丙二醇单甲基醚乙酸酯、环己烷等酮类;四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇单甲基醚等醚类;乙酸乙酯、乙酸正丁酯等酯类;苯、甲苯、二甲苯等芳香族烃;四氯化碳、氯仿、三氯乙烯、二氯甲烷等卤代脂肪族烃;氯苯等卤代芳香族烃。
作为上述(C-4)成分中使用的酚醛树脂,例如可列举出苯酚酚醛清漆树脂、甲酚酚醛清漆树脂、芳香族烃甲醛树脂改性酚醛树脂、二环戊二烯苯酚加成型树脂、苯酚芳烷基树脂(Xyloc resins)、萘酚芳烷基树脂、三苯酚基甲烷树脂、四苯酚基乙烷树脂、萘酚酚醛清漆树脂、萘酚-苯酚共缩合酚醛清漆树脂、萘酚-甲酚共缩合酚醛清漆树脂、联苯改性酚醛树脂(苯酚核通过双亚甲基连接而成的多元酚化合物)、联苯改性萘酚树脂(苯酚核通过双亚甲基连接而成的多元萘酚化合物)、氨基三嗪改性酚醛树脂(在分子结构中具有苯酚骨架、三嗪环及伯氨基的化合物)及含烷氧基的芳香环改性酚醛清漆树脂(苯酚核及含烷氧基的芳香环通过甲醛连接而成的多元酚化合物)等多元酚化合物。
在本发明中,从得到固化性树脂组合物的贮藏稳定性与固化性的平衡优异的观点出发,作为(C-4)酚醛树脂,优选使用软化点为50~200℃的酚醛树脂。
得到上述的作为(C-4)的改性胺时的酚醛树脂的使用量相对于作为(C-1)成分、(C-2)成分和/或(C-3)成分的改性胺100质量份,优选为10~100质量份,特别优选为20~60质量份。通过设定为10质量份以上,可得到充分的固化性,通过设定为100质量份以下,能够更可靠地避免固化物的物性的降低,因此优选。
上述潜在性固化剂中,作为市售品,可列举出ADEKAHardener EH-3636AS(株式会社艾迪科制;双氰胺型潜在性固化剂)、ADEKA Hardener EH-4351S(株式会社艾迪科制;双氰胺型潜在性固化剂)、ADEKA Hardener EH-5011S(株式会社艾迪科制;咪唑型潜在性固化剂)、ADEKA Hardener EH-5046S(株式会社艾迪科制;咪唑型潜在性固化剂)、ADEKAHardener EH-4357S(株式会社艾迪科制;多胺型潜在性固化剂)、ADEKA Hardener EH-5057P(株式会社艾迪科制;多胺型潜在性固化剂)、ADEKA Hardener EH-5057PK(株式会社艾迪科制;多胺型潜在性固化剂)、Amicure PN-23(Ajinomoto Finetechno株式会社制;胺加成系潜在性固化剂)、Amicure PN-40(Ajinomoto Finetechno株式会社制;胺加成系潜在性固化剂)、Amicure VDH(Ajinomoto Finetechno株式会社制;酰肼系潜在性固化剂)、Fujicure FXR-1020(株式会社T&K TOKA制;潜在性固化剂)等。
上述(C)潜在性固化剂的使用量没有特别限定,但相对于(A)氰酸酯树脂及(B)环氧树脂(将4-氨基-3-甲基苯酚型环氧树脂及使用的情况下的其他的环氧树脂合计得到的环氧树脂整体)的合计量100质量份,优选为1~70质量份,更优选为3~60质量份。
在本发明中,可以与上述(C)潜在性固化剂一起根据需要并用公知的固化促进剂。作为这些固化促进剂的具体例子,可例示出三苯基膦等膦类;四苯基溴化鏻等鏻盐;2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰基乙基-2-甲基咪唑等咪唑类;上述咪唑类与偏苯三酸、异氰脲酸、硼等的盐即咪唑盐类;苄基二甲基胺、2,4,6-三(二甲基氨基甲基)苯酚等胺类;三甲基氯化铵等季铵盐类;3-(对氯苯基)-1,1-二甲基脲、3-(3,4-二氯苯基)-1,1-二甲基脲、3-苯基-1,1-二甲基脲、异佛尔酮二异氰酸酯-二甲基脲、甲苯二异氰酸酯-二甲基脲等脲类;及三氟化硼与胺类或醚化合物等的络合物等。这些固化促进剂可以单独使用,也可以将2种以上并用。本发明的固化性树脂组合物中的固化促进剂的含量没有特别限制,可以根据固化性树脂组合物的用途而适宜设定。
此外,在本发明的树脂组合物中,有时根据需要含有各种添加剂。作为上述添加剂,可列举出联苯酚等酚类化合物;单烷基缩水甘油醚等反应性稀释剂;邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、苄基醇、煤焦油等非反应性的稀释剂(增塑剂);熔融二氧化硅、结晶二氧化硅等二氧化硅;氢氧化镁、氢氧化铝、钼酸锌、碳酸钙、碳酸硅、硅酸钙、钛酸钾、氧化铍、氧化锆、锆石、镁橄榄石、块滑石、尖晶石、莫来石、二氧化钛等粉体、或将它们球形化而得到的珠及玻璃纤维、纸浆纤维、合成纤维、陶瓷纤维等填充剂;玻璃布、芳纶布、碳纤维等增强材料;颜料;γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷、γ-巯基丙基三甲氧基硅烷等硅烷偶联剂;小烛树蜡、巴西棕榈蜡、木蜡、白蜡、蜂蜡、羊毛脂、鲸蜡、褐煤蜡、石油蜡、脂肪族蜡、脂肪族酯、脂肪族醚、芳香族酯、芳香族醚等润滑剂;增稠剂;触变剂;抗氧化剂;光稳定剂;紫外线吸收剂;消泡剂;防锈剂;胶体二氧化硅、胶体氧化铝等常用的添加剂。在本发明中,也可以进一步并用二甲苯树脂、石油树脂等粘合性的树脂类。
在本发明的固化性树脂组合物中,可以含有硅烷偶联剂,作为该硅烷偶联剂,例如可列举出γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷、γ-巯基丙基三甲氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷等。
作为硅烷偶联剂的量,通常在固化性树脂组合物的固体成分中(溶剂以外的全部成分中)例如优选列举出0.001~15质量%,更优选为0.01~10质量%。
在本发明的固化性树脂组合物中,可以含有填充剂。作为该填充剂,例如可列举出熔融二氧化硅、结晶二氧化硅等二氧化硅;氢氧化镁、氢氧化铝、钼酸锌、碳酸钙、碳酸硅、硅酸钙、钛酸钾、氧化铍、氧化锆、锆石、镁橄榄石、块滑石、尖晶石、莫来石、氧化钛等粉体、或将它们球形化而得到的珠及玻璃纤维、纸浆纤维、合成纤维、陶瓷纤维等无机填料;丙烯酸树脂、有机硅树脂、聚苯乙烯树脂、聚二乙烯基苯等有机填料;丙烯腈-丁二烯橡胶(NBR)、苯乙烯-丁二烯橡胶(SBR)等橡胶填料;在由丁二烯橡胶等形成的芯中具有丙烯酸树脂、环氧树脂等作为壳的芯壳型橡胶填料等。
作为填充剂的市售品,例如可列举出Mitsubishi Rayon株式会社制的Metablen(注册商标)E系列、Metablen(注册商标)C系列、Metablen(注册商标)W系列;综研化学株式会社制的MX系列、SX系列、SGP系列;Aica Kogyo株式会社制的Zefiac系列;Thermo FisherScientific制的ChromoSphere-T系列;Merck Chimie制的Estapor(注册商标)系列;松浦株式会社制的Fine Pearl(注册商标);JSR公司制XER-91P、XER-81P;Dow Chemical公司制TMS-2670等。
在本发明的固化性树脂组合物含有填充剂的情况下,其含量相对于氰酸酯树脂、环氧树脂及潜在性固化剂的合计量100质量份优选为20质量份以上且1000质量份以下,为50质量份以上且500质量份以下从制成单组分时的作业性的观点出发更优选。
本发明的固化性树脂组合物的特征在于,贮藏稳定性优异,而且其特征在于,初期粘度低,并且粘度上升率低。
即,使用E型粘度计(有时也被称为“E型旋转粘度计”。)以10rpm在25℃下测定的初期粘度为70Pa·s以下,优选粘度上升率在40℃、放置72小时后为150%以下。本发明的固化性树脂组合物放置168小时后的粘度上升率(增粘率)优选为250%以下。使用E型粘度计以10rpm在25℃下测定的初期粘度特别优选为55Pa·s以下。
作为初期粘度的下限,为5Pa·s以上从固化性树脂组合物的制造容易性等方面考虑优选。此外粘度上升率(增粘率)的下限通常为100%。
需要说明的是,上述初期粘度优选为对于在制造后未进行在40℃下放置0.5小时以上的处理的固化性树脂组合物在25℃下用E型粘度计测定的粘度。需要说明的是,粘度设定为在测定前以25℃、10rpm的状态保持10分钟后测定的粘度。
在本发明的固化性树脂组合物中,氰酸酯树脂、环氧树脂、潜在性固化剂以外的成分的量(其中,填充剂及溶剂除外)的量只要是不损害贮藏稳定性及耐热性的量即可,但优选在组合物的固体成分中为10质量%以下从充分确保(A)~(C)成分的量的方面出发优选,更优选为5质量%以下。
在使本发明的固化性树脂组合物固化的情况下,例如在80~200℃下加热由于能发挥固化物物性,因此优选。
本发明的固化性树脂组合物作为通过加热而固化的单组分型的固化性树脂组合物是有用的。
本发明的树脂组合物可以用于针对混凝土、水泥灰浆、各种金属、皮革、玻璃、橡胶、塑料、木、布、纸等的涂料或粘接剂等广泛的用途。特别是由于耐热性优异,因此适宜用于半导体密封或电子部件的粘接剂等电子用途、汽车用途。
实施例
接着,通过实施例及比较例对本发明更详细地进行说明,但本发明不受这些实施例的任何限定。
需要说明的是,以下的实施例等中的%只要没有特别记载则为质量基准。
制造例1(改性多胺的合成)
在烧瓶中投入1,2-二氨基丙烷201g(2.71摩尔)并加温至60℃后,按照***内温度保持在100~110℃的方式一点点地添加Adeka Resin EP-4100E(株式会社艾迪科的商品名;以双酚A型环氧树脂计环氧当量为190)580g(以环氧基计3.05当量)。将Adeka ResinEP-4100E全部添加后,将反应体系升温140℃并反应1.5小时,得到改性多胺。接着,相对于所得到的改性多胺100g投入MP-800K(旭有机材(株式会社)制;酚醛树脂、软化点100℃)30g,以180~190℃、30~40托的条件用1小时进行利用减压脱气的未反应物的除去,使用喷射磨进行粉碎,得到潜在性固化剂(EH-1)。
[实施例1~3以及比较例1及2]
使用通过上述制造例得到的(C)成分即潜在性固化剂、以及作为(A)成分及(B)成分的市售品等来制造树脂组合物,进行下述试验。
对于配方及评价结果,示于下述〔表1〕中。需要说明的是,表1中记载的配方的数值表示质量份。
<初期粘度>
使用E型粘度计〔东机产业株式会社制;TVE-33H、锥板半径7.7mm(3°)〕,以10rpm测定25℃下的粘度。
<增粘率>
将固化性树脂组合物在40℃恒温槽内放置72小时及168小时而进行促进试验,以与初期粘度相同的条件分别测定粘度,由初期粘度求出增粘率。
(促进后的粘度/初期粘度)×100〔%〕
<玻璃化转变温度(Tg)>
使固化性树脂组合物在125℃加热固化1小时而制成4mmφ、10mm的圆筒状的试验片,依据JIS K 7197,使用TMA装置制成平均线膨胀曲线,由其分支点测定玻璃化转变温度(Tg)。将玻璃化转变温度(Tg)超过120℃的情况设定为“A”,将低于120℃的情况设定为“B”。
表1
/>
(注:就比较例1的固化性树脂组合物而言,在40℃放置168小时后固化,无法测定增粘率。比较例2的168小时后的增粘率未测定。)
EP-4300E;双酚A型环氧树脂(株式会社艾迪科制)
EP-4088S;二环戊二烯型环氧树脂(株式会社艾迪科制)
EP-3900S;4-氨基-3-甲基苯酚型环氧树脂(株式会社艾迪科制)
EP-3950S:株式会社艾迪科制;氨基苯酚型环氧树脂
LECy:Lonza公司制;双酚型氰酸酯树脂
粉末填料:平均粒径13.7μm的二氧化硅粉末
KBM-403:Shin-Etsu Silicone;硅烷偶联剂
如通过上述实施例所示的那样,含有本发明的特定的环氧树脂的固化性树脂组合物的贮藏稳定性优异,此外固化物具有充分的耐热性。
与此相对,含有本发明的特定的环氧树脂的固化性树脂组合物见到增粘,贮藏稳定性低劣或固化物不具有耐热性。
产业上的可利用性
本发明的固化性树脂组合物特别是由于贮藏稳定性优异,固化物的耐热性优异,因此例如可以适宜用于电子部件用粘接剂等。
Claims (9)
1.一种固化性树脂组合物,其含有(A)氰酸酯树脂、(B)以4-氨基-3-甲基苯酚型环氧树脂作为必须的环氧树脂及(C)潜在性固化剂。
2.根据权利要求1所述的固化性树脂组合物,其中,作为(A)成分的氰酸酯树脂为选自由下述式(1)所表示的化合物、下述式(2)所表示的化合物及它们中的至少1种的聚合物构成的组中的1种以上,
NC-O-A1-Y1-A2-O-CN (1)
式中,Y1表示非取代或被氟原子或氰氧基取代的2价烃基、或者表示-O-、-S-、或单键,A1及A2分别独立地为非取代或被1~4个烷基取代的亚苯基,
式中,m为1以上的整数,Y2及Y3分别独立地表示-S-、或者表示非取代或被氟原子或氰氧基取代的2价烃基,R1、R2、R3、R4、R5及R6分别独立地为氢原子或碳数1~4的烷基。
3.根据权利要求2所述的固化性树脂组合物,其中,所述式(1)中的Y1以及所述式(2)中的Y2及Y3分别独立地为选自下述式(Y-1)~(Y-9)中的至少1种,
式中,n为4~12的整数,R7及R8分别独立地为氢原子或非取代或被氟原子取代的甲基,此外,*表示键合点。
4.根据权利要求1~3中任一项所述的固化性树脂组合物,其中,作为(C)成分的潜在性固化剂为含活性氢的胺系潜在性固化剂。
5.根据权利要求4所述的固化性树脂组合物,其中,所述含活性氢的胺系潜在性固化剂为选自以下的(C-1)~(C-4)中的至少一种,
(C-1):使具有1个以上活性氢的胺化合物及环氧化合物反应而成的改性胺,
(C-2):使具有1个以上活性氢的胺化合物及异氰酸酯化合物反应而成的改性胺,
(C-3):使具有1个以上活性氢的胺化合物、环氧化合物及异氰酸酯化合物反应而成的改性胺,
(C-4):除了含有选自(C-1)、(C-2)或(C-3)中的至少一种改性胺以外还含有酚醛树脂而成的潜在性固化剂。
6.根据权利要求1~5中任一项所述的固化性树脂组合物,其中,相对于作为(A)成分的氰酸酯树脂100质量份,4-氨基-3-甲基苯酚型环氧树脂的量为1~200质量份。
7.根据权利要求1~6中任一项所述的固化性树脂组合物,对于使用E型旋转粘度计以10rpm在25℃下测定的粘度,初期粘度为70Pa·s以下,在40℃下放置72小时后的粘度上升率为150%以下。
8.一种固化物,其是将权利要求1~7中任一项所述的固化性树脂组合物固化而得到的。
9.一种粘接剂,其包含权利要求1~7中任一项所述的固化性树脂组合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021036706 | 2021-03-08 | ||
JP2021-036706 | 2021-03-08 | ||
PCT/JP2022/004966 WO2022190746A1 (ja) | 2021-03-08 | 2022-02-08 | 硬化性樹脂組成物、硬化物及び接着剤 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116940613A true CN116940613A (zh) | 2023-10-24 |
Family
ID=83227899
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202280017612.4A Pending CN116940613A (zh) | 2021-03-08 | 2022-02-08 | 固化性树脂组合物、固化物及粘接剂 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20240141095A1 (zh) |
EP (1) | EP4306566A1 (zh) |
JP (1) | JPWO2022190746A1 (zh) |
CN (1) | CN116940613A (zh) |
WO (1) | WO2022190746A1 (zh) |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60250026A (ja) | 1984-05-28 | 1985-12-10 | Mitsubishi Rayon Co Ltd | エポキシ樹脂組成物 |
US6469074B1 (en) | 1999-05-26 | 2002-10-22 | Matsushita Electric Works, Ltd. | Composition of cyanate ester, epoxy resin and acid anhydride |
US6632893B2 (en) | 1999-05-28 | 2003-10-14 | Henkel Loctite Corporation | Composition of epoxy resin, cyanate ester, imidazole and polysulfide tougheners |
JP4201632B2 (ja) * | 2003-03-28 | 2008-12-24 | 株式会社Adeka | エポキシ樹脂用硬化剤組成物 |
US7915743B2 (en) | 2006-07-20 | 2011-03-29 | Sekisui Chemical Co., Ltd. | Adhesive for electronic components, method for manufacturing semiconductor chip laminate, and semiconductor device |
JP5346166B2 (ja) | 2007-12-26 | 2013-11-20 | 積水化学工業株式会社 | 電子部品用接着剤 |
JP5118956B2 (ja) | 2007-12-26 | 2013-01-16 | 積水化学工業株式会社 | 電子部品用接着剤 |
JP5431849B2 (ja) | 2009-09-25 | 2014-03-05 | 株式会社Adeka | 無溶剤一液型シアン酸エステル−エポキシ複合樹脂組成物 |
JP5603610B2 (ja) | 2010-02-12 | 2014-10-08 | 株式会社Adeka | 無溶剤一液型シアン酸エステル−エポキシ複合樹脂組成物 |
JP5508342B2 (ja) * | 2011-06-01 | 2014-05-28 | 積水化学工業株式会社 | プリント配線板用bステージフィルム及び多層基板 |
JP6139172B2 (ja) * | 2012-03-13 | 2017-05-31 | 太陽インキ製造株式会社 | 熱硬化性樹脂充填材及びそれを用いて得られるプリント配線板 |
WO2013183303A1 (ja) * | 2012-06-08 | 2013-12-12 | 株式会社Adeka | 硬化性樹脂組成物、樹脂組成物、これらを用いてなる樹脂シート、及びこれらの硬化物 |
JP7060939B2 (ja) * | 2017-10-25 | 2022-04-27 | 株式会社Adeka | 一液型樹脂組成物、その硬化物およびそれを用いた接着剤 |
JP7214981B2 (ja) * | 2018-05-31 | 2023-01-31 | 味の素株式会社 | 樹脂組成物、シート状積層材料、プリント配線板及び半導体装置 |
-
2022
- 2022-02-08 WO PCT/JP2022/004966 patent/WO2022190746A1/ja active Application Filing
- 2022-02-08 EP EP22766711.0A patent/EP4306566A1/en active Pending
- 2022-02-08 CN CN202280017612.4A patent/CN116940613A/zh active Pending
- 2022-02-08 JP JP2023505233A patent/JPWO2022190746A1/ja active Pending
- 2022-02-08 US US18/547,092 patent/US20240141095A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2022190746A1 (ja) | 2022-09-15 |
EP4306566A1 (en) | 2024-01-17 |
JPWO2022190746A1 (zh) | 2022-09-15 |
US20240141095A1 (en) | 2024-05-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101813743B1 (ko) | 마스터 배치형 에폭시 수지용 잠재성 경화제 및 그것을 사용한 에폭시수지 조성물 | |
KR20100075842A (ko) | 일액형 시아네이트-에폭시 복합수지 조성물, 그 경화물 및 그 제조방법, 및 그것을 이용한 봉지용 재료 및 접착제 | |
KR20110124265A (ko) | 일액형 시안산에스테르-에폭시 복합 수지 조성물 | |
US8247517B2 (en) | Catalyst for curing epoxides | |
JP2020200389A (ja) | 硬化性樹脂組成物 | |
CN116940613A (zh) | 固化性树脂组合物、固化物及粘接剂 | |
WO2021112104A1 (ja) | 樹脂組成物 | |
CN115003726B (zh) | 固化性树脂组合物及抑制固化性树脂组合物的固化收缩的方法 | |
EP4029896A1 (en) | Curable resin composition | |
JP7261580B2 (ja) | 樹脂組成物 | |
CN116888184A (zh) | 固化性树脂组合物、固化物及粘接剂 | |
TWI840605B (zh) | 硬化性樹脂組合物 | |
TW202128811A (zh) | 樹脂組合物 | |
WO2022168670A1 (ja) | 電荷移動錯体 | |
CN118076588A (zh) | 包合化合物、环氧树脂固化剂及固化性树脂组合物 | |
WO2023068109A1 (ja) | 硬化性樹脂組成物、硬化物及び接着剤 | |
WO2023171572A1 (ja) | 一液型エポキシ樹脂組成物 | |
CN117413002A (zh) | 环氧树脂组合物 | |
CN116848105A (zh) | 新型化合物及含有该化合物的固化性树脂组合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |