NO150684B - Fotoherdbar blanding inneholdende en polytiol og et polyen avledet fra et vinylacetal - Google Patents
Fotoherdbar blanding inneholdende en polytiol og et polyen avledet fra et vinylacetal Download PDFInfo
- Publication number
- NO150684B NO150684B NO773084A NO773084A NO150684B NO 150684 B NO150684 B NO 150684B NO 773084 A NO773084 A NO 773084A NO 773084 A NO773084 A NO 773084A NO 150684 B NO150684 B NO 150684B
- Authority
- NO
- Norway
- Prior art keywords
- diisocyanate
- vinyl
- terminated
- carbon atoms
- polyester
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 21
- -1 VINYL ACETAL Chemical class 0.000 title claims description 20
- 229920002554 vinyl polymer Polymers 0.000 title claims description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims description 7
- 150000004291 polyenes Chemical class 0.000 title claims description 4
- 229920000728 polyester Polymers 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229920006295 polythiol Polymers 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 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
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 229920005862 polyol Polymers 0.000 claims 2
- 150000003077 polyols Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 229940059574 pentaerithrityl Drugs 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920000921 polyethylene adipate Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RCORSHSFJCXHTF-UHFFFAOYSA-N 2-ethenyl-1,3-dioxan-5-ol Chemical compound OC1COC(C=C)OC1 RCORSHSFJCXHTF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JMAUXGPDSZGZAJ-UHFFFAOYSA-N (2-ethenyl-1,3-dioxolan-4-yl)methanol Chemical compound OCC1COC(C=C)O1 JMAUXGPDSZGZAJ-UHFFFAOYSA-N 0.000 description 2
- PIZPBHHTPIXFLW-UHFFFAOYSA-N (2-ethenyl-5-ethyl-1,3-dioxan-5-yl)methanol Chemical compound CCC1(CO)COC(C=C)OC1 PIZPBHHTPIXFLW-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003847 radiation curing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 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
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- QNKWVRGBHWZNPB-UHFFFAOYSA-N (2-ethenyl-5-ethyl-1,3-dioxan-5-yl)methanol;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.CCC1(CO)COC(C=C)OC1.CCC1(CO)COC(C=C)OC1 QNKWVRGBHWZNPB-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- PGEYWGQQDBYPPM-UHFFFAOYSA-N 1,2-diisocyanatoethane;hexane Chemical compound CCCCCC.O=C=NCCN=C=O PGEYWGQQDBYPPM-UHFFFAOYSA-N 0.000 description 1
- VDDIDKWDKHSMKA-UHFFFAOYSA-N 1,2-diisocyanatoethylbenzene Chemical compound O=C=NCC(N=C=O)C1=CC=CC=C1 VDDIDKWDKHSMKA-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- OUJCKESIGPLCRN-UHFFFAOYSA-N 1,5-diisocyanato-2,2-dimethylpentane Chemical compound O=C=NCC(C)(C)CCCN=C=O OUJCKESIGPLCRN-UHFFFAOYSA-N 0.000 description 1
- QLVWISADYMNPPU-UHFFFAOYSA-N 1,6-diisocyanato-3-methoxyhexane Chemical compound O=C=NCCC(OC)CCCN=C=O QLVWISADYMNPPU-UHFFFAOYSA-N 0.000 description 1
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- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- QCIYAEYRVFUFAP-UHFFFAOYSA-N hexane-2,3-diol Chemical compound CCCC(O)C(C)O QCIYAEYRVFUFAP-UHFFFAOYSA-N 0.000 description 1
- TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 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
- 238000004519 manufacturing process Methods 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/12—Polythioether-ethers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31533—Of polythioether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31931—Polyene monomer-containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Description
Foreliggende oppfinnelse vedrører en fotoherdbar blanding
av den art som er angitt i krav l's ingress.
Den fotoherdbare blanding ifølge oppfinnelsen kan anvendes
for å tilveiebringe sterke, fleksible filmer nyttige for anvendelse som belegg på gulvfliser, tekstiler og tre.
Fra US patent nr. 3.043.580 er kjent polymerer fremstilt
fra polytioler og visse vinylacetalforbindelser, og hvor acetalforbindelsene har en spiro ringstruktur.
I US patentet nr. 3.809.6 33 er vist fotoherdbare bland-
inger inneholdende polytioler og polymerer forskjellige fra de som er avledet fra vinylacetaler. De forskjellige polymerer vist i patentet indikerer ingen polymerer som er avledet fra vinylacetaler.
Foreliggende fotoherdbare blanding er særpreget ved det
som er angitt i krav l's karakteriserende del.
Før det gis en beskrivelse av fremstillingen av blandingene ifølge foreliggende oppfinnelse skal det først angis en fremgangsmåte for syntese av en spesiell utførelse av polyenene avledet fra et vinylacetal, nemlia et hydroksyterminert polyetylenadipat, hvor hydroksygruppen er omsatt med 5-etyl-5-hydroksymetyl-2-vinyl-m-dioksanterminert-toluen-diisocyanat, hvor reaksjonsproduktet inneholder ca. 800 ekvivalentvekter av polyesteren og har et NCO-innhold på
ca. 3% før innføring av endegruppen (I).
5-etyl-5-hydroksyraetyl-2-vinyl-m-dioksan (II) som er et utgangsmateriale for fremstilling av I kan fremstilles fra trimetylolpropan og akrolein ved en reaksjon som er analog med den beskrevet i US-patent nr. 3.010.923 for omsetningen av a, 3/o-trioler med akrolein for fremstilling av vinyl-1,3-diok-salaner.
Behandling av II med ca. 800 ekvivalentvekter hydroksylterminert polyetylenadipatpolyester omsatt med toluendiisocyanat til et NCO-innhold på 3% ved forhøyet temperatur, passende 90°C, i en passende reaksjonstid såsom 9-10 timer gir I.
For fremstilling av en spesiell utførelsesform av blandingene ifølge oppfinnelsen blandes I, pentaerytritoltetrakismerkapto-acetat, en UV-initiator såsom benzofenon, en anti-oksydant, såsom 2,6-di-tertiær-butyl-4-metyl-fenol og, om ønsket, et flyt-regulerende middel såsom "UCC L-7602".
Et egnet flyktig oppløsningsmiddel i en mengde tilstrekkelig til å justere viskositeten for egnet anvendelse kan tilset-tes. Metyletylketon er et egnet oppløsningsmiddel for dette formål.
Det blandede materiale påføres i et tynt lag eller hinne på substratet når det er ønsket å påføre et belegg, og eventuelt oppløsningsmiddel kan deretter avdampe. Den påførte uherdede film blir deretter eksponert med UV-bestråling og herdet.
En fagmann vil forstå at i tillegg til det spesielle utgangsmateriale II, som angitt ovenfor, er det mulig å be-handle akrolein eller akrolein substituert i (3-stillingen med hydrogen, alkyl, halogenalkyl, fluor eller klor med en a, triol såsom glyserol, 1,2,6-heksantriol o.l., eller en a,#,w-triol såsom 1,3,6-heksantriol o.l. i tillegg til trimetylolpropan som vist eller slike trioler som er substituert i |3-eller y-stillingen med alkyl, eller halogenalkyl for å oppnå vinyl-m-dioksan eller vinyl-1,3-dioksolanderivater som er egnet for anvendelse ved utøvelse av oppfinnelsen. Således kan en-hver 1,2,(3 eller høyere) eller 1,3,(5 eller høyere) triol være egnet.
Ytterligere vil det være åpenbart for en fagmann at en hvil-ken som helst hydroksyterminert polyester, polyeter eller polyamid kan erstatte det viste polymere polyetylenadipat som et egnet prepolymer-utgangsmateriale.
Eksempler på egnede polymerer vil være de flytende polyestere som er avledet fra flerverdige alkoholer såsom: etylenglykol, 1,3-propandiol, 1,2-propandiol, 1,3-butandiol, 1,4-butandiol,
2.3- butandiol, 1,3-pentandiol, 1,4-pentandiol, 1,5-pentandiol, 2, 3-pentandiol, 2 , 4-pentandiol, 1, 6-heksandiol, 1 ,-5-heksandiol, 1.4- heksandiol, 1,3-heksandiol, 2,3-heksandiol, 2,4-heksandiol, 2.5- heksandiol, 1,7-heptandiol, 1,5-heptandiol, 3,5-heptandiol, 1,10-dekandiol, para-xylenglykol, bis-(3-hydroksyetyleteren)
av hydrokinon, neopentylglykol, glycerol, pentakrytritol, trimetylolpropan, trietyloletan o.l. og polykarboksylsyrer såsom adipinsyre, oksalsyre, ravsyre, metyladipinsyre, sebacin-syre, glutarsyre, pimelinsyre, azelainsyre, suberinsyre, ftalsyre, tereftalsyre, isoftalsyre, 1,2,4-benzentrikarboksylsyre, ma-leinsyre, fumarsyre, itakonsyre, citraconsyre o.l., flytende polyamider avledet fra omsetningen av polykarboksylsyrer som angitt ovenfor og polyaminer såsom f.eks. etylendiamin, propylen-diamin, butylendiamin, pentametylendiamin, heksametylendia-min, fenylendiamin, tolylendiamin, xylylendiamin, 4,4'-di-amino-difenylmetan, cykloheksylendiamin, naftylendiamin, o.l., eller flytende polyesterpolyamider avledet fra polykarboksylsyrer og aminoalkoholer såsom aminoetanol, aminopropanol, aminobutanol o.l., samt polyestere fremstilt fra laktoner såsom kaprolakton o.l., flerverdige polyalkylenetere såsom kon-densasjonsprodukter av et alkylenoksyd såsom etylenoksyd, pro-pylenoksyd, butylenoksyd, amylenoksyd o.l med en egnet initiator såsom vann eller hvilket som helst av de ovenfornevnte polyalkoholer,. polyaminer eller aminoalkoholer.
I tillegg til toluendiisocyanat som ovenfor vist så vil det være åpenbart at de ovenfornevnte hydroksyterminerte forpoly-merer kan ende-omsettes med andre diisocyanter som et binde-ledd med hydroksy-vinyl-m-dioksaner eller hydroksy-vinyl-1,3-dioksolaner. Eksempler på slike diisocyanater er 1-metoksy-fenyl-2,4-diisocyanat, l-metyl-4-metoksyfenyl-2,5-diisocyanat, 1-etoksyfenyl-2,4-diisocyanat, 1,3-dimetoksyfenyl-4,6-diisocyanat, 1,4-dimetoksyfenyl-2,5-diisocyanat, 1-propoksyfenyl-2,4-diisocyanat, l-isobutyoksy-2,4-diisocyanat, 1,4-dietoksy-fenyl-2,5-diisocyanat, difenyleter-2,4-diisocyanat, naftalen-1,4-diisocyanat, 1,1'-dinaftalen-2,2'-diisocyanat, bifenyl-2,4-diisocyanat, 3,3<1->dimetylbifenyl-4,4-diisocyanat, 3,3'-dimetoksybifenyl,4,4'-diisocyanat, difenylmetan-4,4<1->diisocyanat, difenylmetan-2,4<1->diisocyanat, difenylmetan-2,2'-diisocyanat, 3,3'-dimetoksy-difenylmetan-4,4'-diisocyanat, benzofenon-3,3'-diisocyanat, etylendiisocyanat, propylendi-isocyanat, butylendiisocyanat, pentylendiisocyanat, metylbu-tylendiisocyanat, tetrametylendiisocyanat, pentametylendi-isocyanat, heksanetylendiisocyanat, dipropyldiisocyanateter, heptanetylendiisocyanat, 2,2-dimetylpentylendiisocyanat, 3-metoksy-heksametylendiisocyanat, oktametylendiisocyanat, 2,2,4-trimetylpentylendiisocyanat, 3-butoksyheksametylen-diisocyanat, 1,3-dimetylbenzendiisocyanat, 1,4-dimetylbenzendiisocyanat, 1,2-dimetylcykloheksandiisocyanat, 1,4-dimetylcykloheksandiisocyanat, 1,4-dietylbenzendiisocyanat, 1,4-dimetylnaftalendiisocyanat, 1,5-dimetylnaftalendiisocyanat, cykloheksan-1,3-diisocyanat, cykloheksan-1,4-diisocyanat, l-metylcykloheksan-2,4-diisocyanat, 1-metylcykloheksan,-2,2-diisocyanat, l-etylcykloheksan-2,4-diisocyanat, dicyklohek-sylmetan-4,4'-diisocyanat, dicykloheksylmetylmetan-4,4'-diisocyanat, dicykloheksyldimetylmetan-4,4'-diisocyanat, 2,2-dimetyldicykloheksylmetan-4,4'-diisocyanat, 3,3<1>,5,5<1->tetra-metyldicykloheksylmetan-4,4<1->diisocyanat, 4,4'-metylen-bis-(cykloheksylisocyanat), etylidendiisocyanat, 4,4<1->difenyl-diisocyanat, dianisidindiisocyanat, 1,5-naftalendiisocyanat, m-fenylendiisocyanat, isopropyliden-bis(fenyl eller cyklo-heksylisocyanat), 1,3-cyklopentylendiisocyanat, 1,2-cykloheksylendiisocyanat. 1.4-cykloheksylendiisocyanat, 4,4',4''-trifenylmetantriisocyanat, 1,3,5-triisocyanatbenzen, fenylety-lendiisocyanat o.l..
I tillegg vil det være åpenbart at polytiolkomponenten i blan-dingen ifølge foreliggende oppfinnelse, i tillegg til penta-erytritol-tetrakis-merkaptoacetat kan være tiolanaloge av
de tidligere nevnte polyhydroksyforbindelser eller av de ovenfornevnte polyhydroksypolyetere, polyestere eller polyamider, eller polyesteramider av estere erholdt ved omsetning av disse polyalkoholer med en tiolsubstituert karboksylsyre. Eksempler på disse forbindelser er etanditiol, propanditiol, l,l'-dimer-
kaptodietyleter, bis-(2-merkaptoetyl)-formal,etylenglykol-dimerkaptopropionat o.l..
Som tidligere angitt er det i blandingene ifølge oppfinnelsen påtenkt anvendelse, i tillegg til de nevnte vinylacetal-og polytiolkomponenter, av forskjellige standardadditiver som er vel-kjente innen teknikkens stand for viskositetskontroll, forbed-ret bearbeidbarhet, lagringsstabilitet o.l.. Ingen av disse eller kombinasjoner av disse er spesielt nødvendige for å utnytte oppfinnelsen, og den eneste virkelige begrensning er at de kan være materialer som en fagmann ville forvente ikke å innvirke på strålingsherdingen ved en preferert absorpsjon eller innvirke på penetreringen av den herdende bestråling i den uherdede blanding.
Typiske additiver vil innbefatte flyktige oppløsningsmidler såsom aceton, metyletylketon, metanol, etanol o.l., anti-oksydanter, initiatorer for strålingsherding såsom benzofe-noner, benzoiner og andre kjente forbindelser, strømnings-kontrollerende midler såsom organiske silikoner, reaktive fortynningsmidler for å senke viskositeten for å forbedre filmutspredningen, såsom di-(5-etyl-5-hydroksymetyl-2-vinyl-m-dioksan)-adipat o.l..
De følgende eksempler illustrerer oppfinnelsen.
Eksempel 1
5- etyl- 5- hydroksymetyl- 2- vinyl- m- dioksan
Ved å følge en fremgangsmåte som er analog til den angitt i
U.S. patent nr. 3.010.923 erholdes det fra trimetylolpropan
og akrolein 5-etyl-5-hydroksymetyl-2-vinyl-m-dioksan i et utbytt* på 80%, kp. 1Q0-108°C (1,75-2 , 7mmhg), nD<25>l,4710
Analyse for: C<g>H^O^
Beregnet: C, 62,77%, H, 9,36%, OH-tall, 325,7.
Funnet:C, 62,17%, H, 10,40%, OH-tall, 316,3 (tilsv.)
Syretall, (funnet) 0,15
Eksempel 2
4- hydroksymetyl- 2- vinyl- l, 3- dioksolan og 5- hydroksy- 2- vinyl-m- dioksan
Ved å følge en fremgangsmåte analog med den henvist til i eksempel 1 erholdes 4-hydroksymetyl-2-vinyl-l,3-dioksolan og 5-hydroksy-2-vinyl-m-dioksan som en blanding i utbytte på 62%, kp. 100 - 106°C (13 - 11 mmhg)
Analyse for:C,H.^0_.
b 1U j
Beregnet: C, 55,37%, H, 7,75%, OH-tall 431,1.
Funnet: C, 55,46%, H, 6,88%, OH-tall 423,7 (tilsv.).
Syretall (funnet) 0,12).
Eksempel 3
Toluendiisocyanatterminert polyetylenadipat endeomsatt med 5- etyl- 5- hydroksymetyl- 2- vinyl- m- dioksan
Et hydroksylterminert polyetylenadipat med en initial mole-kylvekt på 800 ble behandlet med toluen-diisocyanat til et NCO-innhold på 2,91%. Den erholdte forbindelse ble behand-
let med forbindelsen i henhold til eksempel 1 ved et 0H/NC0-forhold på 1,05 i 9,5 timer ved 90°C i nærvær av 0,02% feno-tiazin som en polymerisasjonsinhibitor. Det endelige NCO-innhold var 0,53%.
Umetning: (Ekvivalenter/lOOg) (Ved ICl-titrering, 2 ekvivalenter lik 1 mol >C=C<)
Beregnet: 0,13
Funnet: 0,145
Eksempel 4
Toluen- diisocyanatterminert polyester endeomsatt med en blanding av 4- hydroksymetyl- 2- vinyl- l, 3- dioksolan og 5- hydroksy-2- vinyl- m- dioksan
Ved å følge en fremgangsmåte analog med den angitt i eksempel 3 ble den toluendiisocyanatterminerte polyetylen-adipat-polyester, fremstilt i henhold til eksempel 3 omsatt med pro-duktet erholdt i eksempel 2 i 6,5 timer ved 90°C til å gi tittelforbindelsen. Det endelige NCO-innhold var 0,31%.
Umetning: (ICl-titrering, ekvivalenter/100 g)
Beregnet: 0,125
Funnet: 0,14 5
Eksempel 5
Blandinger av vinylacetal- endeavsluttede polyestere og polytioler og polymerer derav
Blandinger av det vinylacetal-endeavsluttede produkt ifølge eksempel 3 og polytioler ble fremstilt som følger:
Filmer av de ovenfornevnte blandinger ble støpt i form av en metyletylketonoppløsning og lufttørket før herding. Etter herding var filmtykkelsen 0,1 mm. Herding ble oppnådd ved 2 gjennomganger ved 6 m/min. under anvendelse av en "QC 1202 AN Processor" (PPG Industries Inc., Radiation Polymer Co.)
med 2 stk.30 cm lamper med en lineær effekttetthet på 7 9 w/cm. Disse blandinger herdet også langsomt ved lufteksponering.
Egenskaper etter UV-herding var som følger:
Claims (5)
1. Fotoherdbar blanding inneholdende en polytiol og et polyen avledet fra et vinylacetal, karakterisert ved at polyenet er en forbindelse med formelen
hvori Q' er en a-verdig rest avledet fra en hydroksylterminert polyester, polyeter, polyamid, .polyester-polyeter, eller polyester-nolyamid ved fjernelse av hydrogen fra hydroksylgrupper, X er en toverdig alkylen- eller arylen-gruppe, Y er en kovalent binding eller en alkylen-gruppe med 1-20 karbonatomer, R er hydrogen, alkyl med 1-20 karbonatomer, eller halogenalkyl med 1-20 karbonatomer, R' er hydrogen, alkyl med 1-20 karbonatomer, halogenalkyl med 1-2 0 karbonatomer, fluor eller klor, n er 0 eller 1 og a er et heltall større enn 1.
2. Blanding ifølge krav 1, karakterisert ved at Q' er avledet fra en hydroksylterminert polyester.
3. Blanding ifølge krav 1, karakterisert ved at polytiolen er en tiolterminert polyester, polyeter, dialkylformal eller ester av en polyol.
4. Blanding ifølge krav 3, karakterisert ved at den tiolterminerte ester av en polyol er penta-erytritoltetrakismerkaptoacetat.
5. Blanding ifølge krav 3, karakterisert ved at den tiolterminerte dialkylformal er bis-(2-merkaptoetyl)-formal.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/720,531 US4157421A (en) | 1976-09-07 | 1976-09-07 | Photocurable compositions comprising a polythiol and a polyene derived from a vinyl acetal |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO773084L NO773084L (no) | 1978-03-08 |
| NO150684B true NO150684B (no) | 1984-08-20 |
| NO150684C NO150684C (no) | 1984-11-28 |
Family
ID=24894325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO773084A NO150684C (no) | 1976-09-07 | 1977-09-06 | Fotoherdbar blanding inneholdende en polytiol og et polyen avledet fra et vinylacetal |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4157421A (no) |
| JP (1) | JPS5342297A (no) |
| AU (1) | AU510213B2 (no) |
| BE (1) | BE858475A (no) |
| BR (1) | BR7705946A (no) |
| CA (1) | CA1111181A (no) |
| CH (1) | CH623350A5 (no) |
| DE (1) | DE2739164A1 (no) |
| DK (1) | DK396077A (no) |
| FR (1) | FR2363598A1 (no) |
| GB (1) | GB1547006A (no) |
| IT (1) | IT1091122B (no) |
| NL (1) | NL175306C (no) |
| NO (1) | NO150684C (no) |
| SE (1) | SE426070B (no) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5656857A (en) * | 1979-10-16 | 1981-05-19 | Showa Highpolymer | Ornamental good |
| US5399624A (en) * | 1990-12-21 | 1995-03-21 | Loctite Corporation | High purity resins for thiol-ene polymerizations and method for producing same |
| US5208281A (en) * | 1991-02-05 | 1993-05-04 | Loctite Corporation | Stabilization of thiolene compositions |
| US5877332A (en) * | 1996-10-18 | 1999-03-02 | E. I. Du Pont De Nemours And Company | Reactive adducts of vinyldioxo compounds |
| EP1268568A4 (en) * | 2000-02-15 | 2003-05-28 | Foster Miller Inc | RESIN COMPOSITIONS CURABLE BY RADIATION WITHOUT VOLATILE ORGANIC CONSTITUENT |
| US7378457B2 (en) * | 2000-02-15 | 2008-05-27 | Foster Miller, Inc. | No VOC radiation curable resin compositions with enhanced flexibility |
| US8092921B2 (en) * | 2007-08-17 | 2012-01-10 | Ppg Industries Ohio, Inc | Clearcoat composition for use in waterborne basecoat-clearcoat composite coatings |
| JP6079277B2 (ja) * | 2013-02-04 | 2017-02-15 | 日本ゼオン株式会社 | 感放射線樹脂組成物及び電子部品 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL231223A (no) * | 1957-09-10 | 1900-01-01 | ||
| US3043850A (en) * | 1957-09-26 | 1962-07-10 | Union Carbide Corp | Chemical compounds containing sulfur and spirobi (meta-dioxane) groups |
| US3225014A (en) * | 1962-07-09 | 1965-12-21 | Scott Paper Co | Ethylene dicarboxylic esters of 1,2 alkane ketals |
| US3809633A (en) * | 1972-03-08 | 1974-05-07 | Grace W R & Co | Chain extended polythioether polyene photocurable compositions |
| US3931353A (en) * | 1973-10-18 | 1976-01-06 | Showa High Polymer Co., Ltd. | Polymerizable cycloacetal resinous composition |
| US3908039A (en) * | 1973-10-25 | 1975-09-23 | Grace W R & Co | Photocurable polyene-polythiol lacquer composition |
| US3976553A (en) * | 1974-09-09 | 1976-08-24 | W. R. Grace & Co. | Curable polyene-polythiol compounds and methods for preparation and curing |
| JPS5314800A (en) * | 1976-07-28 | 1978-02-09 | Showa Highpolymer Co Ltd | Curable resin composition |
-
1976
- 1976-09-07 US US05/720,531 patent/US4157421A/en not_active Expired - Lifetime
-
1977
- 1977-08-15 AU AU27885/77A patent/AU510213B2/en not_active Expired
- 1977-08-16 CA CA284,769A patent/CA1111181A/en not_active Expired
- 1977-08-19 NL NLAANVRAGE7709196,A patent/NL175306C/xx not_active IP Right Cessation
- 1977-08-31 CH CH1061477A patent/CH623350A5/fr not_active IP Right Cessation
- 1977-08-31 DE DE19772739164 patent/DE2739164A1/de not_active Ceased
- 1977-09-02 IT IT50882/77A patent/IT1091122B/it active
- 1977-09-05 SE SE7709954A patent/SE426070B/xx not_active IP Right Cessation
- 1977-09-05 JP JP10656077A patent/JPS5342297A/ja active Granted
- 1977-09-06 BR BR7705946A patent/BR7705946A/pt unknown
- 1977-09-06 NO NO773084A patent/NO150684C/no unknown
- 1977-09-06 GB GB37219/77A patent/GB1547006A/en not_active Expired
- 1977-09-06 DK DK396077A patent/DK396077A/da not_active Application Discontinuation
- 1977-09-06 FR FR7726973A patent/FR2363598A1/fr active Granted
- 1977-09-07 BE BE180728A patent/BE858475A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE426070B (sv) | 1982-12-06 |
| NO150684C (no) | 1984-11-28 |
| BE858475A (fr) | 1978-01-02 |
| AU2788577A (en) | 1979-02-22 |
| CA1111181A (en) | 1981-10-20 |
| FR2363598A1 (fr) | 1978-03-31 |
| DE2739164A1 (de) | 1978-03-09 |
| IT1091122B (it) | 1985-06-26 |
| JPS5342297A (en) | 1978-04-17 |
| US4157421A (en) | 1979-06-05 |
| NL175306C (nl) | 1984-10-16 |
| NL7709196A (nl) | 1978-03-09 |
| JPS5410596B2 (no) | 1979-05-08 |
| BR7705946A (pt) | 1978-07-04 |
| NO773084L (no) | 1978-03-08 |
| SE7709954L (sv) | 1978-03-08 |
| CH623350A5 (no) | 1981-05-29 |
| NL175306B (nl) | 1984-05-16 |
| AU510213B2 (en) | 1980-06-12 |
| FR2363598B1 (no) | 1983-11-25 |
| DK396077A (da) | 1978-03-08 |
| GB1547006A (en) | 1979-06-06 |
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