CA1124933A - Substances thermodurcissables a base de resine d'epoxyde et contenant un sel onium d'un compose aromatique et un agent reducteur - Google Patents

Substances thermodurcissables a base de resine d'epoxyde et contenant un sel onium d'un compose aromatique et un agent reducteur

Info

Publication number: CA1124933A
Authority: CA; Canada
Prior art keywords: aromatic; heat curable; integer equal; curable composition; inclusive
Prior art date: 1976-05-24
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.): Expired

Application number

CA277,774A

Other languages

English (en)

Inventor

James V. Crivello

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.)

General Electric Co

Original Assignee

General Electric Co

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.)

1976-05-24

Filing date

1977-05-05

Publication date

1982-06-01

1977-05-05 Application filed by General Electric Co filed Critical General Electric Co

1982-06-01 Application granted granted Critical

1982-06-01 Publication of CA1124933A publication Critical patent/CA1124933A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 76
150000003839 salts Chemical class 0.000 title claims abstract description 50
125000003118 aryl group Chemical group 0.000 title claims abstract description 39
239000003638 chemical reducing agent Substances 0.000 title claims abstract description 22
239000003822 epoxy resin Substances 0.000 title claims description 23
229920000647 polyepoxide Polymers 0.000 title claims description 23
-1 aromatic iodonium salt Chemical class 0.000 claims description 45
150000003254 radicals Chemical class 0.000 claims description 18
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 16
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 12
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical group [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 12
239000011368 organic material Substances 0.000 claims description 12
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
LLMLGZUZTFMXSA-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzenethiol Chemical group SC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LLMLGZUZTFMXSA-UHFFFAOYSA-N 0.000 claims description 6
229960005070 ascorbic acid Drugs 0.000 claims description 6
235000010323 ascorbic acid Nutrition 0.000 claims description 6
239000011668 ascorbic acid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000005520 diaryliodonium group Chemical group 0.000 claims description 5
229910052787 antimony Inorganic materials 0.000 claims description 4
229910052785 arsenic Inorganic materials 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
150000001879 copper Chemical class 0.000 claims description 4
229920001568 phenolic resin Polymers 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
229910052711 selenium Inorganic materials 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
150000001868 cobalt Chemical class 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
159000000014 iron salts Chemical class 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
229910052752 metalloid Inorganic materials 0.000 claims description 3
150000002738 metalloids Chemical class 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
230000000269 nucleophilic effect Effects 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
235000000346 sugar Nutrition 0.000 claims description 3
150000008163 sugars Chemical class 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
229910052714 tellurium Inorganic materials 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052797 bismuth Inorganic materials 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
229910052710 silicon Inorganic materials 0.000 claims description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims 1
239000007859 condensation product Substances 0.000 claims 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical group C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims 1
229920005989 resin Polymers 0.000 abstract description 22
239000011347 resin Substances 0.000 abstract description 22
239000004593 Epoxy Substances 0.000 abstract description 14
238000000034 method Methods 0.000 abstract description 10
150000001875 compounds Chemical class 0.000 abstract description 9
238000000576 coating method Methods 0.000 abstract description 2
239000003999 initiator Substances 0.000 abstract description 2
238000004382 potting Methods 0.000 abstract description 2
239000000853 adhesive Substances 0.000 abstract 1
230000001070 adhesive effect Effects 0.000 abstract 1
239000011248 coating agent Substances 0.000 abstract 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 9
238000010438 heat treatment Methods 0.000 description 7
229940050390 benzoate Drugs 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
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 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000002091 cationic group Chemical group 0.000 description 5
150000004292 cyclic ethers Chemical class 0.000 description 5
229960004279 formaldehyde Drugs 0.000 description 5
239000000463 material Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000007787 solid Substances 0.000 description 5
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 4
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 4
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 4
230000008859 change Effects 0.000 description 4
239000010949 copper Substances 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
YCZWJBIXAUQULS-UHFFFAOYSA-M bis(4-methylphenyl)iodanium;bromide Chemical compound [Br-].C1=CC(C)=CC=C1[I+]C1=CC=C(C)C=C1 YCZWJBIXAUQULS-UHFFFAOYSA-M 0.000 description 3
229940106691 bisphenol a Drugs 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
239000011521 glass Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229920001187 thermosetting polymer Polymers 0.000 description 3
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HLYRMDDXFDINCB-UHFFFAOYSA-N carbon monoxide;iron Chemical group [Fe].[Fe].[Fe].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] HLYRMDDXFDINCB-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
XYVVCFFJQVMSNN-UHFFFAOYSA-N cyclopenta-1,3-diene iron(2+) 5-octylcyclopenta-1,3-diene Chemical compound [Fe++].c1cc[cH-]c1.CCCCCCCC[c-]1cccc1 XYVVCFFJQVMSNN-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000013007 heat curing Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000007639 printing Methods 0.000 description 2
239000011669 selenium Substances 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
IOHJRUFWMYLKED-UHFFFAOYSA-N 1,3,3-trimethylazetidine Chemical compound CN1CC(C)(C)C1 IOHJRUFWMYLKED-UHFFFAOYSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
CZAVRNDQSIORTH-UHFFFAOYSA-N 1-ethenoxy-2,2-bis(ethenoxymethyl)butane Chemical compound C=COCC(CC)(COC=C)COC=C CZAVRNDQSIORTH-UHFFFAOYSA-N 0.000 description 1
SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910017048 AsF6 Inorganic materials 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
101100005514 Mus musculus Ccdc40 gene Proteins 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910052779 Neodymium Inorganic materials 0.000 description 1
229910052781 Neptunium Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
229910052777 Praseodymium Inorganic materials 0.000 description 1
229910052774 Proactinium Inorganic materials 0.000 description 1
239000004614 Process Aid Substances 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 description 1
NRTJGTSOTDBPDE-UHFFFAOYSA-N [dimethyl(methylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[SiH2]O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C NRTJGTSOTDBPDE-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical compound [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
WLLASMDMMUPSMP-UHFFFAOYSA-N benzoic acid;copper Chemical compound [Cu].OC(=O)C1=CC=CC=C1 WLLASMDMMUPSMP-UHFFFAOYSA-N 0.000 description 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
YRPWLKVCRKAUAO-UHFFFAOYSA-N bismuthonium Chemical class [BiH4+] YRPWLKVCRKAUAO-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000004567 concrete Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
239000011243 crosslinked material Substances 0.000 description 1
238000001723 curing Methods 0.000 description 1
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
239000012955 diaryliodonium Substances 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
JMJGNDIWCVQJJZ-UHFFFAOYSA-M diphenyliodanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 JMJGNDIWCVQJJZ-UHFFFAOYSA-M 0.000 description 1
238000009837 dry grinding Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
229960004594 fominoben Drugs 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
238000001879 gelation Methods 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000000976 ink Substances 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
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MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002919 oxepanes Chemical class 0.000 description 1
150000002921 oxetanes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 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
229920002857 polybutadiene Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
229960000380 propiolactone Drugs 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229910052706 scandium Inorganic materials 0.000 description 1
239000000565 sealant Substances 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229940100890 silver compound Drugs 0.000 description 1
150000003379 silver compounds Chemical class 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
150000003413 spiro compounds Chemical class 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
150000003498 tellurium compounds Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000007984 tetrahydrofuranes Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
VFWRNIOSEGGKQE-UHFFFAOYSA-N thiourea;1,3,5-triazine-2,4,6-triamine Chemical compound NC(N)=S.NC1=NC(N)=NC(N)=N1 VFWRNIOSEGGKQE-UHFFFAOYSA-N 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
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 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229920006163 vinyl copolymer Polymers 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Epoxy Resins (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA277,774A 1976-05-24 1977-05-05 Substances thermodurcissables a base de resine d'epoxyde et contenant un sel onium d'un compose aromatique et un agent reducteur Expired CA1124933A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date
US68924776A	1976-05-24	1976-05-24
US689,247		1976-05-24
US78178577A	1977-03-28	1977-03-28
US781,785		1977-03-28
US84135177A	1977-10-12	1977-10-12
US841,351		1977-10-12

Publications (1)

Publication Number	Publication Date
CA1124933A true CA1124933A (fr)	1982-06-01

Family

ID=27418514

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA277,774A Expired CA1124933A (fr)	1976-05-24	1977-05-05	Substances thermodurcissables a base de resine d'epoxyde et contenant un sel onium d'un compose aromatique et un agent reducteur

Country Status (1)

Country	Link
CA (1)	CA1124933A (fr)

1977
- 1977-05-05 CA CA277,774A patent/CA1124933A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-06-01	MKEX	Expiry

Publication	Publication Date	Title
US4216288A (en)	1980-08-05	Heat curable cationically polymerizable compositions and method of curing same with onium salts and reducing agents
US4173551A (en)	1979-11-06	Heat curable compositions
US4108747A (en)	1978-08-22	Curable compositions and method for curing such compositions
EP0023912B1 (fr)	1985-07-31	Compositions thermodurcissables
US4026705A (en)	1977-05-31	Photocurable compositions and methods
US4238587A (en)	1980-12-09	Heat curable compositions
US4283312A (en)	1981-08-11	Heat curable processable epoxy compositions containing aromatic iodonium salt catalyst and copper salt cocatalyst
US4374066A (en)	1983-02-15	Method for making triarylsulfonium salts
KR840001676B1 (ko)	1984-10-13	광경화성 조성물
GB2081271A (en)	1982-02-17	Polymerization initiator compositions
JPS6136530B2 (fr)	1986-08-19
US4336363A (en)	1982-06-22	Heat curable compositions containing sulfonium salts
JPH0688927B2 (ja)	1994-11-09	光重合性有機組成物に使用するジアリールヨードニウム塩及びその製造方法
GB2055379A (en)	1981-03-04	Moulding a cationically polymerisable material
EP0276716A2 (fr)	1988-08-03	Compositions de résine époxyde à durcissement retardé
US4412064A (en)	1983-10-25	Metal atom containing epoxy resins
GB2042550A (en)	1980-09-24	Cationically heat polymerisable materials
US4683317A (en)	1987-07-28	Photopolymerizable organic compositions and diaryliodonium salts used therein
US4329306A (en)	1982-05-11	Heat curable processable epoxy compositions
US4857562A (en)	1989-08-15	UV curable epoxy resin compositions with delayed cure
JPS6146002B2 (fr)	1986-10-11
US4780511A (en)	1988-10-25	Method for making polymeric photoactive aryl iodonium salts, products obtained therefrom, and use
US4239725A (en)	1980-12-16	Low temperature curable organic resin compositions
DE2854011C2 (de)	1983-04-21	Hitzehärtbare Masse und Verfahren zu deren Herstellung
GB2027435A (en)	1980-02-20	Curable Resin Compositions