JPS6311945B2 - - Google Patents

Info

Publication number: JPS6311945B2
Authority: JP; Japan
Prior art keywords: ethylenically unsaturated; polythiol; general formula; oligomer; liquid
Prior art date: 1980-12-22
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

JP56203850A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57130572A (en

Inventor

Uein Butsushu Richaado

Gen Kangu Uan

Robaato Moogan Chaarusu

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.)

WR Grace and Co

Original Assignee

WR Grace and 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.)

1980-12-22

Filing date

1981-12-18

Publication date

1988-03-16

1981-12-18 Application filed by WR Grace and Co filed Critical WR Grace and Co

1982-08-13 Publication of JPS57130572A publication Critical patent/JPS57130572A/ja

1988-03-16 Publication of JPS6311945B2 publication Critical patent/JPS6311945B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 53
229920006295 polythiol Polymers 0.000 claims description 48
238000000576 coating method Methods 0.000 claims description 29
239000011248 coating agent Substances 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical class CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 19
-1 alkarylcarbonyl Chemical group 0.000 claims description 17
239000007788 liquid Substances 0.000 claims description 16
238000010438 heat treatment Methods 0.000 claims description 14
239000003999 initiator Substances 0.000 claims description 14
239000000178 monomer Substances 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
229920005989 resin Polymers 0.000 claims description 6
239000011347 resin Substances 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001451 organic peroxides Chemical class 0.000 claims description 5
229920001187 thermosetting polymer Polymers 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000001788 irregular Effects 0.000 claims 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
150000001875 compounds Chemical class 0.000 description 16
238000012360 testing method Methods 0.000 description 14
238000001723 curing Methods 0.000 description 13
150000004291 polyenes Chemical class 0.000 description 12
239000000047 product Substances 0.000 description 10
230000005855 radiation Effects 0.000 description 10
238000009472 formulation Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 7
VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
230000006866 deterioration Effects 0.000 description 5
WGOQVOGFDLVJAW-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCOC(N)=O WGOQVOGFDLVJAW-UHFFFAOYSA-N 0.000 description 5
KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
230000009977 dual effect Effects 0.000 description 4
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
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 4
MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 3
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000945 filler Substances 0.000 description 3
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
235000019645 odor Nutrition 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000000376 reactant Substances 0.000 description 3
125000003396 thiol group Chemical group [H]S* 0.000 description 3
150000003573 thiols Chemical group 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 2
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229920002799 BoPET Polymers 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
239000005041 Mylar™ Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
235000008098 Oxalis acetosella Nutrition 0.000 description 2
229920002176 Pluracol® Polymers 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
244000126309 Trifolium dubium Species 0.000 description 2
238000003848 UV Light-Curing Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
229910003460 diamond Inorganic materials 0.000 description 2
239000010432 diamond Substances 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
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000007598 dipping method Methods 0.000 description 2
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000013007 heat curing Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000009965 odorless effect Effects 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000004014 plasticizer Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
229940079877 pyrogallol Drugs 0.000 description 2
238000005507 spraying Methods 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
238000005382 thermal cycling Methods 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
229920006305 unsaturated polyester Polymers 0.000 description 2
DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 1
WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
MIOKJIDWWJEJDE-UHFFFAOYSA-N (4-dodecyl-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(CCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 MIOKJIDWWJEJDE-UHFFFAOYSA-N 0.000 description 1
CGCQHMFVCNWSOV-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-phenylmethanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C1=CC=CC=C1 CGCQHMFVCNWSOV-UHFFFAOYSA-N 0.000 description 1
AJBYSHYIHCXTJQ-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluoro-2,3-diphenylbutane-2,3-diol Chemical compound C=1C=CC=CC=1C(O)(C(F)(F)F)C(O)(C(F)(F)F)C1=CC=CC=C1 AJBYSHYIHCXTJQ-UHFFFAOYSA-N 0.000 description 1
VTOOGDARGVVKLQ-UHFFFAOYSA-N 1,1,2,2-tetraphenyl-2-propan-2-yloxyethanol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(OC(C)C)C1=CC=CC=C1 VTOOGDARGVVKLQ-UHFFFAOYSA-N 0.000 description 1
ZEMRSQHDAGIOTD-UHFFFAOYSA-N 1,1,2-triphenylpropane-1,2-diol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC=CC=1)C(O)(C)C1=CC=CC=C1 ZEMRSQHDAGIOTD-UHFFFAOYSA-N 0.000 description 1
BWPJLSPQUNGKQZ-UHFFFAOYSA-N 1,1-bis(2,4-dichlorophenyl)-2,2-diphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C(=CC(Cl)=CC=1)Cl)C=1C(=CC(Cl)=CC=1)Cl)(O)C1=CC=CC=C1 BWPJLSPQUNGKQZ-UHFFFAOYSA-N 0.000 description 1
OHKVRIVNMUXAOQ-UHFFFAOYSA-N 1,1-bis(2-methylphenyl)-2,2-diphenylethane-1,2-diol Chemical compound CC1=CC=CC=C1C(O)(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1C OHKVRIVNMUXAOQ-UHFFFAOYSA-N 0.000 description 1
KDHCSLNPQZEWBH-UHFFFAOYSA-N 1,1-bis(3,4-dimethylphenyl)-2,2-diphenylethane-1,2-diol Chemical compound C1=C(C)C(C)=CC=C1C(O)(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(C)C(C)=C1 KDHCSLNPQZEWBH-UHFFFAOYSA-N 0.000 description 1
JORQGTJZHBZEHD-UHFFFAOYSA-N 1,1-bis(3-methylphenyl)-2,2-diphenylethane-1,2-diol Chemical compound CC1=CC=CC(C(O)(C=2C=C(C)C=CC=2)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JORQGTJZHBZEHD-UHFFFAOYSA-N 0.000 description 1
HIXLMCZVMOANAF-UHFFFAOYSA-N 1,1-bis(4-bromophenyl)-2,2-diphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC(Br)=CC=1)C=1C=CC(Br)=CC=1)(O)C1=CC=CC=C1 HIXLMCZVMOANAF-UHFFFAOYSA-N 0.000 description 1
FBTYPWJRYOYHQE-UHFFFAOYSA-N 1,1-bis(4-chlorophenyl)-2,2-diphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC(Cl)=CC=1)C=1C=CC(Cl)=CC=1)(O)C1=CC=CC=C1 FBTYPWJRYOYHQE-UHFFFAOYSA-N 0.000 description 1
VZQFCVMLOYILGA-UHFFFAOYSA-N 1,1-bis(4-iodophenyl)-2,2-diphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC(I)=CC=1)C=1C=CC(I)=CC=1)(O)C1=CC=CC=C1 VZQFCVMLOYILGA-UHFFFAOYSA-N 0.000 description 1
XNNDIBBGVGGPOG-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-2,2-diphenylethane-1,2-diol Chemical compound C1=CC(OC)=CC=C1C(O)(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(OC)C=C1 XNNDIBBGVGGPOG-UHFFFAOYSA-N 0.000 description 1
SKENUMRDZMMSNY-UHFFFAOYSA-N 1,1-bis(4-methylphenyl)-2,2-diphenylethane-1,2-diol Chemical compound C1=CC(C)=CC=C1C(O)(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=C(C)C=C1 SKENUMRDZMMSNY-UHFFFAOYSA-N 0.000 description 1
DSGBXJDPUBKFJX-UHFFFAOYSA-N 1,1-diphenyl-2,2-bis(4-phenylphenyl)ethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 DSGBXJDPUBKFJX-UHFFFAOYSA-N 0.000 description 1
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150000002148 esters Chemical class 0.000 description 1
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000007654 immersion Methods 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
230000005865 ionizing radiation Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
238000000016 photochemical curing Methods 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000550 preparative sample Substances 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
238000007725 thermal activation Methods 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 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

Classifications

- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
- H05K3/287—Photosensitive compositions
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
- B05D3/0209—Multistage baking
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D2401/00—Form of the coating product, e.g. solution, water dispersion, powders or the like
- B05D2401/30—Form of the coating product, e.g. solution, water dispersion, powders or the like the coating being applied in other forms than involving eliminable solvent, diluent or dispersant
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
- B05D3/0254—After-treatment

Landscapes

Engineering & Computer Science (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Microelectronics & Electronic Packaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Manufacturing & Machinery (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Plasma & Fusion (AREA)
Paints Or Removers (AREA)
Application Of Or Painting With Fluid Materials (AREA)
Non-Metallic Protective Coatings For Printed Circuits (AREA)

JP56203850A 1980-12-22 1981-12-18 Method of coating article with irregular shape which combine and use ultraviolet ray and heat Granted JPS57130572A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US21903380A	1980-12-22	1980-12-22

Publications (2)

Publication Number	Publication Date
JPS57130572A JPS57130572A (en)	1982-08-13
JPS6311945B2 true JPS6311945B2 (de)	1988-03-16

Family

ID=22817543

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56203850A Granted JPS57130572A (en)	1980-12-22	1981-12-18	Method of coating article with irregular shape which combine and use ultraviolet ray and heat

Country Status (8)

Country	Link
JP (1)	JPS57130572A (de)
AU (1)	AU541021B2 (de)
BR (1)	BR8105838A (de)
DE (1)	DE3141743A1 (de)
FR (1)	FR2496503A1 (de)
GB (1)	GB2089819B (de)
IT (1)	IT1139494B (de)
SE (1)	SE8107243L (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU569290B2 (en) *	1981-11-17	1988-01-28	Eurofloor S.A.	Matting of synthetic surfaces
CA1194637A (en) *	1982-04-26	1985-10-01	Charles R. Morgan	Uv and thermally curable, thermoplastic-containing compositions
DE3445922C2 (de) *	1984-02-09	1987-05-14	Reinhard 4992 Espelkamp Stanger	Schutzbeschichtungsverfahren
CS253754B1 (en) *	1984-03-16	1987-12-17	Otto Wichterle	Method of device for monomere mixtures polymerization during contact lenses centrifugal production
US4588609A (en) *	1984-11-26	1986-05-13	Leyden Richard N	Process for the photochemical vapor deposition of aromatic polymers
DE3527404C1 (de) *	1985-07-31	1987-01-02	Kurz Leonhard Fa	Verfahren zur Herstellung einer eine texturierte Lackschicht aufweisenden Folie
DE3837569A1 (de) *	1988-11-04	1990-05-10	Espe Stiftung	Mit sichtbarem licht aushaertbare dentalmassen
JP3160428B2 (ja) *	1993-07-12	2001-04-25	株式会社東芝	濃度計
WO1997023524A1 (en) *	1995-12-22	1997-07-03	Alliedsignal Inc.	Thermosetting acrylic materials of high glass transition temperature
US6414048B1 (en) *	1999-12-07	2002-07-02	Sumitomo Electric Fine Polymer, Inc.	Chemical grafting onto a substrate and coating composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4020233A (en) *	1976-01-22	1977-04-26	W. R. Grace & Co.	Heat activated ethylenically unsaturated-polythiol compositions

1981
- 1981-09-14 BR BR8105838A patent/BR8105838A/pt unknown
- 1981-09-16 AU AU75298/81A patent/AU541021B2/en not_active Ceased
- 1981-09-28 IT IT24195/81A patent/IT1139494B/it active
- 1981-10-21 DE DE19813141743 patent/DE3141743A1/de not_active Withdrawn
- 1981-12-03 SE SE8107243A patent/SE8107243L/xx not_active Application Discontinuation
- 1981-12-04 GB GB8136644A patent/GB2089819B/en not_active Expired
- 1981-12-18 JP JP56203850A patent/JPS57130572A/ja active Granted
- 1981-12-21 FR FR8123842A patent/FR2496503A1/fr active Granted

Also Published As

Publication number	Publication date
JPS57130572A (en)	1982-08-13
IT1139494B (it)	1986-09-24
FR2496503B1 (de)	1985-04-26
AU7529881A (en)	1982-07-01
SE8107243L (sv)	1982-06-23
IT8124195A0 (it)	1981-09-28
GB2089819B (en)	1985-02-06
BR8105838A (pt)	1982-09-08
GB2089819A (en)	1982-06-30
AU541021B2 (en)	1984-12-13
FR2496503A1 (fr)	1982-06-25
DE3141743A1 (de)	1982-07-22

Publication	Publication Date	Title
US4288527A (en)	1981-09-08	Dual UV/thermally curable acrylate compositions with pinacol
CA1194637A (en)	1985-10-01	Uv and thermally curable, thermoplastic-containing compositions
US4008341A (en)	1977-02-15	Curable liquid polymer compositions
US4020233A (en)	1977-04-26	Heat activated ethylenically unsaturated-polythiol compositions
US4605465A (en)	1986-08-12	UV and thermally curable, thermoplastic-containing compositions
Shukla et al.	2004	Review of basic chemistry of UV‐curing technology
US4222835A (en)	1980-09-16	In depth curing of resins induced by UV radiation
US3898349A (en)	1975-08-05	Polyene/polythiol paint vehicle
US4406826A (en)	1983-09-27	Heat curable conductive ink
US4352723A (en)	1982-10-05	Method of curing a dual UV/thermally curable acrylate composition
JPS6311945B2 (de)	1988-03-16
US3783152A (en)	1974-01-01	N-arylene polycarbamate
US4081598A (en)	1978-03-28	Flame retardant mercaptocarboxylic acid esters of halogenated polyols
US4230740A (en)	1980-10-28	Heat stable, non-yellowing photopolymer compositions
US4031271A (en)	1977-06-21	Alkali-resistant radiation curable ene-thiol compositions
US3925320A (en)	1975-12-09	Solid curable polyene compositions containing liquid polythiols and solid styrene-allyl alcohol copolymer based polyenes
US4006270A (en)	1977-02-01	Solid curable polyene compositions and method of coating therewith
US3662022A (en)	1972-05-09	Curable liquid composition of polyene,polymercaptan and acrylic acid
CA1172112A (en)	1984-08-07	Process for making conductive coatings
US3701721A (en)	1972-10-31	Curable liquid polyene-polythiol compositions containing polyacrylic acid and derivatives thereof
US4132812A (en)	1979-01-02	Photocurable imidizable polyene-polythiol compositions
US4045516A (en)	1977-08-30	Solid curable polyene compositions containing a polythiol
US3728240A (en)	1973-04-17	Curable liquid polyene-polythiol compositions containing acrylic acid copolymers
GB2089818A (en)	1982-06-30	Photocurable compositions containing a photoinitiator and an azo compound or peroxide
JPH01289820A (ja)	1989-11-21	活性エネルギー線硬化型不飽和樹脂組成物