CA1080881A - Radiation-curable coating compositions comprising mercaptoalkyl silicone and vinyl monomer - Google Patents
Radiation-curable coating compositions comprising mercaptoalkyl silicone and vinyl monomerInfo
- Publication number
- CA1080881A CA1080881A CA265,103A CA265103A CA1080881A CA 1080881 A CA1080881 A CA 1080881A CA 265103 A CA265103 A CA 265103A CA 1080881 A CA1080881 A CA 1080881A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- weight
- compositions
- radicals
- radiation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 48
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 7
- 125000005358 mercaptoalkyl group Chemical group 0.000 title claims description 13
- 229920001296 polysiloxane Polymers 0.000 title description 4
- 239000008199 coating composition Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 155
- 230000001070 adhesive effect Effects 0.000 claims abstract description 38
- 239000000853 adhesive Substances 0.000 claims abstract description 37
- 239000000758 substrate Substances 0.000 claims abstract description 30
- 230000005855 radiation Effects 0.000 claims abstract description 24
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 11
- 239000012530 fluid Substances 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 230000002165 photosensitisation Effects 0.000 claims abstract description 5
- 125000002348 vinylic group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 238000002156 mixing Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000000576 coating method Methods 0.000 abstract description 40
- -1 siloxanes Chemical class 0.000 description 33
- 239000011248 coating agent Substances 0.000 description 26
- 239000000123 paper Substances 0.000 description 24
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 14
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 11
- 239000012965 benzophenone Substances 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 229920005573 silicon-containing polymer Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000003522 acrylic cement Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 150000003440 styrenes Chemical class 0.000 description 3
- 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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002655 kraft paper Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000012429 release testing Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
- IZMZREOTRMMCCB-UHFFFAOYSA-N 1,4-dichloro-2-ethenylbenzene Chemical compound ClC1=CC=C(Cl)C(C=C)=C1 IZMZREOTRMMCCB-UHFFFAOYSA-N 0.000 description 1
- OBRYRJYZWVLVLF-UHFFFAOYSA-N 1-ethenyl-4-ethoxybenzene Chemical compound CCOC1=CC=C(C=C)C=C1 OBRYRJYZWVLVLF-UHFFFAOYSA-N 0.000 description 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 description 1
- 241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 241000984642 Cura Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 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
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001145 hydrido group Chemical class *[H] 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000005051 trimethylchlorosilane 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/122—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to saturated polysiloxanes containing hydrolysable groups, e.g. alkoxy-, thio-, hydroxy-
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/40—Adhesives in the form of films or foils characterised by release liners
- C09J7/401—Adhesives in the form of films or foils characterised by release liners characterised by the release coating composition
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/20—Presence of organic materials
- C09J2400/28—Presence of paper
- C09J2400/283—Presence of paper in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2483/00—Presence of polysiloxane
- C09J2483/005—Presence of polysiloxane in the release coating
-
- 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]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesive Tapes (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paper (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/688,197 US4070526A (en) | 1976-05-20 | 1976-05-20 | Radiation-curable coating compositions comprising mercaptoalkyl silicone and vinyl monomer, method of coating therewith and coated article |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080881A true CA1080881A (en) | 1980-07-01 |
Family
ID=24763511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA265,103A Expired CA1080881A (en) | 1976-05-20 | 1976-11-08 | Radiation-curable coating compositions comprising mercaptoalkyl silicone and vinyl monomer |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4070526A (enExample) |
| JP (1) | JPS52141862A (enExample) |
| AT (1) | AT358278B (enExample) |
| AU (1) | AU501865B2 (enExample) |
| BE (1) | BE850266A (enExample) |
| BR (1) | BR7608292A (enExample) |
| CA (1) | CA1080881A (enExample) |
| DE (1) | DE2651009C3 (enExample) |
| ES (1) | ES465175A1 (enExample) |
| FR (1) | FR2352032A1 (enExample) |
| GB (1) | GB1570099A (enExample) |
| IT (1) | IT1123933B (enExample) |
| MX (1) | MX144991A (enExample) |
| SE (1) | SE428570B (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182723A (en) * | 1976-04-15 | 1980-01-08 | Permavision | Ocular membrane and method for preparation thereof |
| JPS5345404A (en) * | 1976-10-05 | 1978-04-24 | Shinetsu Chem Ind Co | Size treated paperboard |
| JPS53102949A (en) * | 1977-02-21 | 1978-09-07 | Shin Etsu Chem Co Ltd | Elastomer composition |
| US4133939A (en) * | 1977-12-16 | 1979-01-09 | Dow Corning Corporation | Method for applying a silicone release coating and coated article therefrom |
| US4163082A (en) * | 1978-10-23 | 1979-07-31 | Dow Corning Corporation | U.V.-radiation method for decreasing surface tack of disposed organopolysiloxane greases and gels |
| US4234697A (en) * | 1979-01-18 | 1980-11-18 | Dow Corning Corporation | Method of preparing cross-linked polydiorganosiloxane using organic isocyanates and products prepared therefrom |
| FR2447386A1 (fr) * | 1979-01-24 | 1980-08-22 | Rhone Poulenc Ind | Compositions organopolysiloxaniques photopolymerisables |
| US4237208A (en) * | 1979-02-15 | 1980-12-02 | Rca Corporation | Silane electron beam resists |
| US4303484A (en) * | 1979-08-22 | 1981-12-01 | Shin-Etsu Chemical Co., Ltd. | Photocurable organopolysiloxane compositions |
| GB2057476B (en) * | 1979-08-29 | 1983-06-22 | Shinetsu Chemical Co | Photocurable organopolysiloxane compositions |
| US4322450A (en) * | 1979-09-24 | 1982-03-30 | Scott Paper Company | Surface replication on a coated substrate |
| IT1130512B (it) * | 1979-09-24 | 1986-06-18 | Scott Paper Co | Rivestimento di distacco per carta e altri substrati in foglio e metodi per la loro preparazione |
| DE3201194A1 (de) * | 1982-01-16 | 1983-07-28 | Bayer Ag, 5090 Leverkusen | Vernetzbare pfropfpolymerisat-dispersionen aus hydrogensiloxan-gruppen und si-vinyl-gruppen enthaltenden organopolysiloxanen |
| DE3201205A1 (de) * | 1982-01-16 | 1983-07-28 | Bayer Ag, 5090 Leverkusen | Pfropfmodifizierte siloxandispersionen zur ausruestung von textilen materialien |
| US4576999A (en) * | 1982-05-06 | 1986-03-18 | General Electric Company | Ultraviolet radiation-curable silicone release compositions with epoxy and/or acrylic functionality |
| DE3314729C2 (de) * | 1983-04-22 | 1996-06-05 | Polymer Physik Gmbh | Selbstklebende Kunststoff-Folie, die auf der nichtklebenden Seite mit einer klebstoffabweisenden Schutzschicht versehen ist, sowie deren Herstellung und Verwendung als Wasserschutzfolie zum Abdecken von Karosserieteilen |
| US4547431A (en) * | 1983-06-20 | 1985-10-15 | General Electric Company | Ultraviolet radiation-curable silicone controlled release compositions |
| US4558147A (en) * | 1983-08-26 | 1985-12-10 | General Electric Company | Ultraviolet radiation-curable silicone release compositions |
| US4608312A (en) * | 1983-08-26 | 1986-08-26 | General Electric Company | Ultraviolet radiation curable silicone release compositions |
| JPS60228517A (ja) * | 1984-04-26 | 1985-11-13 | Kanegafuchi Chem Ind Co Ltd | 新規重合体の製造法 |
| JPS60228516A (ja) * | 1984-04-26 | 1985-11-13 | Kanegafuchi Chem Ind Co Ltd | 新規重合体の製造法 |
| JPS60231761A (ja) * | 1984-05-01 | 1985-11-18 | Shin Etsu Chem Co Ltd | 硬化性シリコ−ンゴム組成物 |
| US5137448A (en) * | 1984-07-31 | 1992-08-11 | Dentsply Research & Development Corp. | Dental impression method with photocuring of impression material in light transmissive tray |
| EP0184598A1 (en) * | 1984-12-06 | 1986-06-18 | Toray Silicone Company Limited | Ultraviolet and electron-beam curable polyorganosiloxane composition |
| US4839123A (en) * | 1986-08-18 | 1989-06-13 | Mobil Oil Corporation | Process of applying a silicone release coating to an oriented polymer film |
| US4831064A (en) * | 1986-12-22 | 1989-05-16 | Dow Corning Corporation | Organopolysiloxane compositions curable by ultraviolet radiation |
| US4911986A (en) * | 1987-02-09 | 1990-03-27 | Dow Corning Corporation | Curable silicone compositions comprising vinyl monomer |
| US4725630A (en) * | 1987-06-01 | 1988-02-16 | Wacker Silicones Corporation | α, β-unsaturated carbonyl-functional silicone compositions |
| JPH01215832A (ja) * | 1988-02-24 | 1989-08-29 | Showa Denko Kk | 剥離性材料の製造方法 |
| DE3918328A1 (de) * | 1989-06-05 | 1990-12-13 | Wacker Chemie Gmbh | Waermehaertbare zusammensetzungen |
| US5032460A (en) * | 1989-08-14 | 1991-07-16 | Minnesota Mining And Manufacturing Company | Method of making vinyl-silicone copolymers using mercapto functional silicone chain-transfer agents and release coatings made therewith |
| WO1992016590A1 (en) * | 1991-03-20 | 1992-10-01 | Minnesota Mining And Manufacturing Company | Radiation curable vinyl/silicone release coating |
| WO1992016593A2 (en) * | 1991-03-20 | 1992-10-01 | Minnesota Mining And Manufacturing Company | Radiation-curable acrylate/silicone pressure-sensitive adhesive compositions |
| US5264278A (en) * | 1991-03-20 | 1993-11-23 | Minnesota Mining And Manufacturing Company | Radiation-curable acrylate/silicone pressure-sensitive adhesive coated tapes adherable to paint coated substrates |
| US5464659A (en) * | 1991-05-23 | 1995-11-07 | Minnesota Mining And Manufacturing Company | Silicone/acrylate vibration dampers |
| US5308887A (en) * | 1991-05-23 | 1994-05-03 | Minnesota Mining & Manufacturing Company | Pressure-sensitive adhesives |
| DE4135142A1 (de) * | 1991-10-24 | 1993-04-29 | Wacker Chemie Gmbh | S-alkylthiosulfatgruppen aufweisende organosiliciumverbindungen, verfahren zu ihrer herstellung und verwendung dieser organosiliciumverbindungen |
| US5387465A (en) * | 1992-07-30 | 1995-02-07 | General Electric Company | Paper adhesive release system |
| DE4228790C1 (de) * | 1992-08-29 | 1993-11-25 | Du Pont Deutschland | Tonbares strahlungsempfindliches Gemisch und Verfahren zur Herstellung von Mehrfarbenbildern mittels solch eines Gemischs |
| TW268969B (enExample) * | 1992-10-02 | 1996-01-21 | Minnesota Mining & Mfg | |
| US5728469A (en) * | 1995-06-06 | 1998-03-17 | Avery Dennison Corporation | Block copolymer release surface for pressure sensitive adhesives |
| US5932352A (en) * | 1995-11-21 | 1999-08-03 | Higgins; David Edward | Release film |
| JP2003033321A (ja) * | 2001-07-25 | 2003-02-04 | Pentax Corp | 前方視型二チャンネル内視鏡 |
| US7105584B2 (en) | 2003-04-18 | 2006-09-12 | Nscg, Inc. | Dual-cure silicone compounds exhibiting elastomeric properties |
| US20060019725A1 (en) * | 2004-07-20 | 2006-01-26 | Inventec Appliances Corporation | Personal handphone system handset for children |
| US20060128826A1 (en) * | 2004-11-18 | 2006-06-15 | Ellison Matthew M | Ultra-thin thiol-ene coatings |
| JP5489389B2 (ja) * | 2005-07-28 | 2014-05-14 | 地方独立行政法人 大阪市立工業研究所 | 紫外線硬化性樹脂組成物、当該硬化物、およびこれらから誘導される各種物品 |
| US20140111859A1 (en) * | 2012-10-19 | 2014-04-24 | Corning Incorporated | Scratch resistant polarizing articles and methods for making and using same |
| US20160230014A1 (en) * | 2013-09-13 | 2016-08-11 | Basf Se | Scratch-resistant radiation-cured coatings |
| US9790640B2 (en) * | 2014-02-24 | 2017-10-17 | Gary S Selwyn | Composition and process for applying hydrophobic coating to fibrous substrates |
| WO2018190188A1 (ja) * | 2017-04-13 | 2018-10-18 | 信越化学工業株式会社 | 剥離性放射線硬化性シリコーン組成物及び剥離シート |
| CN112358580B (zh) * | 2017-09-20 | 2023-05-16 | 杭州乐一新材料科技有限公司 | 一种用于3d打印的硫醇-烯光固化树脂及其制备方法 |
| TWI801443B (zh) | 2017-10-27 | 2023-05-11 | 美商陶氏有機矽公司 | 可固化聚有機矽氧烷組成物、藉由固化該等組成物獲得之固化體、及包含其之電子裝置 |
| US12234389B2 (en) | 2019-10-03 | 2025-02-25 | 3M Innovative Properties Company | Silicone elastomers by free radical mediated cure |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL126303C (enExample) * | 1965-01-08 | 1900-01-01 | ||
| GB1200476A (en) * | 1966-12-07 | 1970-07-29 | Wacker Chemie Gmbh | Heat-curable casting and impregnating resins based on organopolysiloxanes |
| US3436252A (en) * | 1967-04-13 | 1969-04-01 | Stauffer Chemical Co | Paper release composition |
| US3532729A (en) * | 1967-09-25 | 1970-10-06 | Dow Corning | Preparation of siloxanes in emulsion |
| US3686356A (en) * | 1970-08-25 | 1972-08-22 | Dow Corning | Method of blending polyorganosiloxane and organic vinylic thermoplastics and products thereof |
| US3726710A (en) * | 1970-09-02 | 1973-04-10 | Union Carbide Corp | Silicon paper release compositions |
| US3816282A (en) * | 1971-04-15 | 1974-06-11 | Gen Electric | Radiation induced polymerization of polysiloxanes |
| US3770687A (en) * | 1971-07-27 | 1973-11-06 | Gaf Corp | Controlled release coating composition and process |
| US3873499A (en) * | 1973-11-29 | 1975-03-25 | Dow Corning | Fast curing mercaptoalkyl vinyl siloxane resins |
| US3923923A (en) * | 1974-03-11 | 1975-12-02 | Dow Corning | Toughened polystyrene |
-
1976
- 1976-05-20 US US05/688,197 patent/US4070526A/en not_active Expired - Lifetime
- 1976-11-03 SE SE7612232A patent/SE428570B/xx not_active IP Right Cessation
- 1976-11-08 AU AU19406/76A patent/AU501865B2/en not_active Expired
- 1976-11-08 CA CA265,103A patent/CA1080881A/en not_active Expired
- 1976-11-08 DE DE2651009A patent/DE2651009C3/de not_active Expired
- 1976-11-08 GB GB46436/76A patent/GB1570099A/en not_active Expired
- 1976-11-09 AT AT830376A patent/AT358278B/de not_active IP Right Cessation
- 1976-11-17 MX MX167045A patent/MX144991A/es unknown
- 1976-11-22 IT IT2960676A patent/IT1123933B/it active
- 1976-11-25 JP JP14174476A patent/JPS52141862A/ja active Granted
- 1976-12-10 BR BR7608292A patent/BR7608292A/pt unknown
-
1977
- 1977-01-10 FR FR7700475A patent/FR2352032A1/fr active Granted
- 1977-01-11 BE BE173981A patent/BE850266A/xx not_active IP Right Cessation
- 1977-12-16 ES ES465175A patent/ES465175A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52141862A (en) | 1977-11-26 |
| ATA830376A (de) | 1980-01-15 |
| IT1123933B (it) | 1986-04-30 |
| FR2352032A1 (fr) | 1977-12-16 |
| AU501865B2 (en) | 1979-07-05 |
| US4070526A (en) | 1978-01-24 |
| BE850266A (fr) | 1977-07-11 |
| SE428570B (sv) | 1983-07-11 |
| DE2651009A1 (de) | 1977-11-24 |
| DE2651009B2 (de) | 1980-10-23 |
| AT358278B (de) | 1980-08-25 |
| DE2651009C3 (de) | 1981-08-13 |
| BR7608292A (pt) | 1977-11-29 |
| JPS5337376B2 (enExample) | 1978-10-07 |
| ES465175A1 (es) | 1978-10-01 |
| MX144991A (es) | 1981-12-10 |
| FR2352032B1 (enExample) | 1980-04-25 |
| SE7612232L (sv) | 1977-11-21 |
| GB1570099A (en) | 1980-06-25 |
| AU1940676A (en) | 1978-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |