CA1274646A - Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements - Google Patents

Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements

Info

Publication number: CA1274646A
Authority: CA; Canada
Prior art keywords: aromatic; group; organic material; parts; radicals
Prior art date: 1975-05-02
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

CA000226109A

Other languages

English (en)

Other versions

CA226109S (en

Inventor

James Vincent 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.)

1975-05-02

Filing date

1975-05-02

Publication date

1990-09-25

1975-05-02 Application filed by General Electric Co filed Critical General Electric Co

1975-05-02 Priority to CA000226109A priority Critical patent/CA1274646A/fr

1978-10-26 Priority to CA000314333A priority patent/CA1283425C/fr

1990-09-25 Application granted granted Critical

1990-09-25 Publication of CA1274646A publication Critical patent/CA1274646A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 88
150000003839 salts Chemical class 0.000 title claims abstract description 28
230000005855 radiation Effects 0.000 title abstract description 9
239000011368 organic material Substances 0.000 claims abstract description 21
125000003118 aryl group Chemical group 0.000 claims abstract description 13
125000004122 cyclic group Chemical group 0.000 claims abstract description 13
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 11
-1 aromatic iodonium salt Chemical class 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
229910052752 metalloid Inorganic materials 0.000 claims description 4
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
150000002738 metalloids Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
150000002596 lactones Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000011951 cationic catalyst Substances 0.000 claims 1
150000004294 cyclic thioethers Chemical group 0.000 claims 1
125000004185 ester group Chemical group 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000003566 oxetanyl group Chemical group 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
238000000576 coating method Methods 0.000 abstract description 23
239000011248 coating agent Substances 0.000 abstract description 18
229920005989 resin Polymers 0.000 abstract description 18
239000011347 resin Substances 0.000 abstract description 18
229920002554 vinyl polymer Polymers 0.000 abstract description 11
239000000178 monomer Substances 0.000 abstract description 10
150000001875 compounds Chemical class 0.000 abstract description 7
150000004292 cyclic ethers Chemical class 0.000 abstract description 6
238000010538 cationic polymerization reaction Methods 0.000 abstract description 4
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
238000000465 moulding Methods 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
229920000642 polymer Polymers 0.000 description 19
239000011521 glass Substances 0.000 description 18
239000003822 epoxy resin Substances 0.000 description 17
229920000647 polyepoxide Polymers 0.000 description 17
239000004593 Epoxy Substances 0.000 description 13
229910000831 Steel Inorganic materials 0.000 description 13
239000010959 steel Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
238000000034 method Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 10
239000000463 material Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229910052753 mercury Inorganic materials 0.000 description 7
239000003921 oil Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000002841 Lewis acid Substances 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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 6
239000011968 lewis acid catalyst Substances 0.000 description 6
150000007517 lewis acids Chemical class 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000758 substrate Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000007639 printing Methods 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000012954 diazonium Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000976 ink Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
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 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 3
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
230000008859 change Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000004205 dimethyl polysiloxane Substances 0.000 description 3
235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
239000004744 fabric Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920003986 novolac Polymers 0.000 description 3
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
229920001169 thermoplastic Polymers 0.000 description 3
238000004804 winding Methods 0.000 description 3
ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 2
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 2
SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
101100010166 Mus musculus Dok3 gene Proteins 0.000 description 2
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 2
150000001412 amines Chemical class 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000010894 electron beam technology Methods 0.000 description 2
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
VNWHJJCHHGPAEO-UHFFFAOYSA-N fluoroboronic acid Chemical compound OB(O)F VNWHJJCHHGPAEO-UHFFFAOYSA-N 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
229920002857 polybutadiene Polymers 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
238000004382 potting Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004416 thermosoftening plastic Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
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
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
VQBRSCDCSOKQHR-UHFFFAOYSA-N 1-cyclopropylethenylbenzene Chemical compound C=1C=CC=CC=1C(=C)C1CC1 VQBRSCDCSOKQHR-UHFFFAOYSA-N 0.000 description 1
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
WPMHMYHJGDAHKX-UHFFFAOYSA-N 1-ethenylpyrene Chemical compound C1=C2C(C=C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WPMHMYHJGDAHKX-UHFFFAOYSA-N 0.000 description 1
ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
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 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
LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
KUQRLZZWFINMDP-BGNLRFAXSA-N 2-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KUQRLZZWFINMDP-BGNLRFAXSA-N 0.000 description 1
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical group OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
QESYYRDPBSQZHZ-UHFFFAOYSA-N 2-ethenyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(C=C)C=C3CC2=C1 QESYYRDPBSQZHZ-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
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
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229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
241001120493 Arene Species 0.000 description 1
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229910017048 AsF6 Inorganic materials 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
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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 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
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239000004418 Lexan Substances 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
229910052779 Neodymium Inorganic materials 0.000 description 1
229910052781 Neptunium Inorganic materials 0.000 description 1
101100396546 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) tif-6 gene Proteins 0.000 description 1
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229910052774 Proactinium Inorganic materials 0.000 description 1
239000004614 Process Aid Substances 0.000 description 1
229910008046 SnC14 Inorganic materials 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
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150000001255 actinides Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
229940106691 bisphenol a Drugs 0.000 description 1
HODFCFXCOMKRCG-UHFFFAOYSA-N bitolterol mesylate Chemical compound CS([O-])(=O)=O.C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)C[NH2+]C(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 HODFCFXCOMKRCG-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000004567 concrete Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000008393 encapsulating agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000005670 ethenylalkyl group Chemical group 0.000 description 1
YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical compound C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
230000004907 flux Effects 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000005414 inactive ingredient Substances 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
229910003475 inorganic filler Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
239000005340 laminated glass Substances 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
150000002895 organic esters Chemical class 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
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical group C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229920002120 photoresistant polymer Polymers 0.000 description 1
239000000049 pigment Substances 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
239000001230 potassium iodate Substances 0.000 description 1
229940093930 potassium iodate Drugs 0.000 description 1
235000006666 potassium iodate Nutrition 0.000 description 1
239000002244 precipitate Substances 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
239000005297 pyrex Substances 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
238000009877 rendering Methods 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
230000000452 restraining effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000005096 rolling process Methods 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
239000004065 semiconductor Substances 0.000 description 1
229910001542 sodium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
150000003413 spiro compounds Chemical class 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000007984 tetrahydrofuranes Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000009974 thixotropic effect Effects 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 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
229960000834 vinyl ether Drugs 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D347/00—Heterocyclic compounds containing rings having halogen atoms as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Paints Or Removers (AREA)

CA000226109A 1975-05-02 1975-05-02 Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements Expired CA1274646A (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA000226109A CA1274646A (fr)	1975-05-02	1975-05-02	Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements
CA000314333A CA1283425C (fr)	1975-05-02	1978-10-26	Sels metalliques hexafluores de diphenyliodonium

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000226109A CA1274646A (fr)	1975-05-02	1975-05-02	Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000314333A Division CA1283425C (fr)	1975-05-02	1978-10-26	Sels metalliques hexafluores de diphenyliodonium

Publications (1)

Publication Number	Publication Date
CA1274646A true CA1274646A (fr)	1990-09-25

Family

ID=4102984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000226109A Expired CA1274646A (fr)	1975-05-02	1975-05-02	Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements

Country Status (1)

Country	Link
CA (1)	CA1274646A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10683266B2 (en)	2016-06-29	2020-06-16	San Apro Ltd.	Sulfonium salt, photoacid generator, photocurable composition, and cured product thereof
US11370751B2 (en)	2016-07-28	2022-06-28	San Apro Ltd.	Sulfonium salt, heat- or photo-acid generator, heat- or photo-curable composition, and cured product thereof

1975
- 1975-05-02 CA CA000226109A patent/CA1274646A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10683266B2 (en)	2016-06-29	2020-06-16	San Apro Ltd.	Sulfonium salt, photoacid generator, photocurable composition, and cured product thereof
US11370751B2 (en)	2016-07-28	2022-06-28	San Apro Ltd.	Sulfonium salt, heat- or photo-acid generator, heat- or photo-curable composition, and cured product thereof

Legal Events

Date	Code	Title	Description
1996-03-25	MKLA	Lapsed

Publication	Publication Date	Title
US4310469A (en)	1982-01-12	Diaryliodonium salts
US4026705A (en)	1977-05-31	Photocurable compositions and methods
US4058400A (en)	1977-11-15	Cationically polymerizable compositions containing group VIa onium salts
US4150988A (en)	1979-04-24	Method of photopolymerizing polymerizable compositions containing group Va onium salts
US4058401A (en)	1977-11-15	Photocurable compositions containing group via aromatic onium salts
US4161405A (en)	1979-07-17	Method of cationally polymerizing oxirane free materials with group VIa onium salts
US4175972A (en)	1979-11-27	Curable epoxy compositions containing aromatic onium salts and hydroxy compounds
US4069055A (en)	1978-01-17	Photocurable epoxy compositions containing group Va onium salts
CA1285686C (fr)	1991-07-02	Compositions vulcanisables a teneur de complexes metallogenes, precurseurs actives qui en sont derives, et emploi de ces derniers
US4264703A (en)	1981-04-28	Cationically polymerizable compositions containing photodecomposable aromatic iodonium salts
US4108747A (en)	1978-08-22	Curable compositions and method for curing such compositions
US4374751A (en)	1983-02-22	Polymerization initiator compositions
US3835003A (en)	1974-09-10	Photopolymerization of oxetanes
US4216288A (en)	1980-08-05	Heat curable cationically polymerizable compositions and method of curing same with onium salts and reducing agents
US4442197A (en)	1984-04-10	Photocurable compositions
US4374066A (en)	1983-02-15	Method for making triarylsulfonium salts
JPS6326105B2 (fr)	1988-05-27
GB1565671A (en)	1980-04-23	Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials
US5073643A (en)	1991-12-17	High yield synthesis of hydroxyl-containing cationic photoinitiators
US4175973A (en)	1979-11-27	Curable compositions
US4529490A (en)	1985-07-16	Photopolymerizable organic compositions and diaryliodonium ketone salts used therein
GB1578674A (en)	1980-11-05	Coating method
Crivello et al.	1979	The photoinitiated cationic polymerization of epoxy resins
US4307177A (en)	1981-12-22	Method of using polymerizable compositions containing onium salts
EP0011918B1 (fr)	1984-03-07	Compositions polymérisables, enduits et autres produits polymérisés obtenus

CA1274646A - Compositions polymerisables a teneur de sels d'halonium sensibles aux rayonnements - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (2)

Applications Claiming Priority (1)

Related Child Applications (1)

Publications (1)

Family

ID=4102984

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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