EP1685193A4 - Dual-cure-reaktionsprodukte von selbstphotoinitiierenden multifunktionellen acrylaten mit cycloaliphatischen epoxidverbindungen - Google Patents

Dual-cure-reaktionsprodukte von selbstphotoinitiierenden multifunktionellen acrylaten mit cycloaliphatischen epoxidverbindungen

Info

Publication number: EP1685193A4
Authority: EP; European Patent Office
Prior art keywords: oligomeric composition; liquid oligomeric; group; dicarbonyl; acrylate
Prior art date: 2003-11-14
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP04810830A

Other languages

English (en)

French (fr)

Other versions

EP1685193A2 (de

Inventor

Laurence G Dammann

Robert B Fechter

Sridevi Narayan-Sarathy

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.)

Ineos Composites IP LLC

Original Assignee

Ashland Licensing and Intellectual Property LLC

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.)

2003-11-14

Filing date

2004-11-12

Publication date

2006-12-13

2003-11-14 Priority claimed from US10/712,044 external-priority patent/US7041749B2/en

2004-11-12 Application filed by Ashland Licensing and Intellectual Property LLC filed Critical Ashland Licensing and Intellectual Property LLC

2006-08-02 Publication of EP1685193A2 publication Critical patent/EP1685193A2/de

2006-12-13 Publication of EP1685193A4 publication Critical patent/EP1685193A4/de

Status Withdrawn legal-status Critical Current

Links

150000001252 acrylic acid derivatives Chemical class 0.000 title claims abstract description 6
150000001875 compounds Chemical class 0.000 title claims description 25
239000004593 Epoxy Substances 0.000 title claims description 18
239000007795 chemical reaction product Substances 0.000 title claims description 8
230000009977 dual effect Effects 0.000 title description 8
238000001723 curing Methods 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 106
239000007788 liquid Substances 0.000 claims abstract description 69
150000002118 epoxides Chemical class 0.000 claims abstract description 43
238000006845 Michael addition reaction Methods 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 28
229920000058 polyacrylate Polymers 0.000 claims abstract description 15
150000004798 β-ketoamides Chemical class 0.000 claims abstract description 6
-1 cyclic amidines Chemical class 0.000 claims description 45
238000000576 coating method Methods 0.000 claims description 37
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 34
239000012952 cationic photoinitiator Substances 0.000 claims description 19
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 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
239000000047 product Substances 0.000 claims description 15
239000000758 substrate Substances 0.000 claims description 15
229940096522 trimethylolpropane triacrylate Drugs 0.000 claims description 15
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 14
239000000654 additive Substances 0.000 claims description 12
125000004386 diacrylate group Chemical group 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 claims description 10
230000000996 additive effect Effects 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000002535 acidifier Substances 0.000 claims description 9
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
239000000853 adhesive Substances 0.000 claims description 8
230000001070 adhesive effect Effects 0.000 claims description 8
150000004703 alkoxides Chemical class 0.000 claims description 8
125000000524 functional group Chemical group 0.000 claims description 8
239000000565 sealant Substances 0.000 claims description 8
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 7
239000000976 ink Substances 0.000 claims description 7
150000002978 peroxides Chemical class 0.000 claims description 7
229920000728 polyester Polymers 0.000 claims description 7
PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 6
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 6
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
239000003607 modifier Substances 0.000 claims description 6
229920003986 novolac Polymers 0.000 claims description 6
239000003973 paint Substances 0.000 claims description 6
239000000049 pigment Substances 0.000 claims description 6
PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 4
PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 claims description 4
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 4
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 claims description 4
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 4
YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 4
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical group CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims description 4
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
239000002202 Polyethylene glycol Substances 0.000 claims description 3
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 3
IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 3
229920001223 polyethylene glycol Polymers 0.000 claims description 3
229920001296 polysiloxane Polymers 0.000 claims description 3
MXFQRSUWYYSPOC-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)(C)COC(=O)C=C MXFQRSUWYYSPOC-UHFFFAOYSA-N 0.000 claims description 2
ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
VRWWRSQIOZLGAM-UHFFFAOYSA-N 2,2-bis(3-oxobutanoyloxymethyl)butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(CC)(COC(=O)CC(C)=O)COC(=O)CC(C)=O VRWWRSQIOZLGAM-UHFFFAOYSA-N 0.000 claims description 2
BCFBCLJFXYLWCI-UHFFFAOYSA-N 2,3-bis(3-oxobutanoyloxy)propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(OC(=O)CC(C)=O)COC(=O)CC(C)=O BCFBCLJFXYLWCI-UHFFFAOYSA-N 0.000 claims description 2
FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 2
ZYXNLVMBIHVDRH-UHFFFAOYSA-N 2-Methylpropyl 3-oxobutanoate Chemical compound CC(C)COC(=O)CC(C)=O ZYXNLVMBIHVDRH-UHFFFAOYSA-N 0.000 claims description 2
OHCUUVLMXARGTH-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCC(C)OCC(C)OCC(C)OCC(C)OC(=O)C=C OHCUUVLMXARGTH-UHFFFAOYSA-N 0.000 claims description 2
GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 2
QAUIAXORENGBSN-UHFFFAOYSA-N 2-ethylhexyl 3-oxobutanoate Chemical compound CCCCC(CC)COC(=O)CC(C)=O QAUIAXORENGBSN-UHFFFAOYSA-N 0.000 claims description 2
PLHCSZRZWOWUBW-UHFFFAOYSA-N 2-methoxyethyl 3-oxobutanoate Chemical compound COCCOC(=O)CC(C)=O PLHCSZRZWOWUBW-UHFFFAOYSA-N 0.000 claims description 2
VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims description 2
DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 claims description 2
GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims description 2
IHSFHIUGYHMYNR-UHFFFAOYSA-N 4-(3-oxobutanoyloxy)butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC(=O)CC(C)=O IHSFHIUGYHMYNR-UHFFFAOYSA-N 0.000 claims description 2
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
XAMCLRBWHRRBCN-UHFFFAOYSA-N 5-prop-2-enoyloxypentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCOC(=O)C=C XAMCLRBWHRRBCN-UHFFFAOYSA-N 0.000 claims description 2
PVVNFQFWDCPPNQ-UHFFFAOYSA-N 6-(3-oxobutanoyloxy)hexyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCCCOC(=O)CC(C)=O PVVNFQFWDCPPNQ-UHFFFAOYSA-N 0.000 claims description 2
WOFAGNLBCJWEOE-UHFFFAOYSA-N Benzyl acetoacetate Chemical compound CC(=O)CC(=O)OCC1=CC=CC=C1 WOFAGNLBCJWEOE-UHFFFAOYSA-N 0.000 claims description 2
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 2
239000004641 Diallyl-phthalate Substances 0.000 claims description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 2
AOSWRWMLSUAOIP-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.NC1=NC(N)=NC(N)=N1 Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.NC1=NC(N)=NC(N)=N1 AOSWRWMLSUAOIP-UHFFFAOYSA-N 0.000 claims description 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
AOUVCMGRGUPDDD-UHFFFAOYSA-N [1-(prop-2-enoyloxymethyl)cyclohexyl]methyl prop-2-enoate Chemical class C=CC(=O)OCC1(COC(=O)C=C)CCCCC1 AOUVCMGRGUPDDD-UHFFFAOYSA-N 0.000 claims description 2
RASITSWSKYLIEX-UHFFFAOYSA-N [2,2-dimethyl-3-(3-oxobutanoyloxy)propyl] 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(C)(C)COC(=O)CC(C)=O RASITSWSKYLIEX-UHFFFAOYSA-N 0.000 claims description 2
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 2
AUHWLIZFLUXUDG-UHFFFAOYSA-N [3-(3-oxobutanoyloxy)-2,2-bis(3-oxobutanoyloxymethyl)propyl] 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC(COC(=O)CC(C)=O)(COC(=O)CC(C)=O)COC(=O)CC(C)=O AUHWLIZFLUXUDG-UHFFFAOYSA-N 0.000 claims description 2
KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 claims description 2
FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
GGGZAPAKHRYJCQ-UHFFFAOYSA-N cyclohexane;methanol;3-oxobutanoic acid Chemical compound OC.OC.C1CCCCC1.CC(=O)CC(O)=O.CC(=O)CC(O)=O GGGZAPAKHRYJCQ-UHFFFAOYSA-N 0.000 claims description 2
IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical class [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 claims description 2
KCHWKBCUPLJWJA-UHFFFAOYSA-N dodecyl 3-oxobutanoate Chemical compound CCCCCCCCCCCCOC(=O)CC(C)=O KCHWKBCUPLJWJA-UHFFFAOYSA-N 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
150000002357 guanidines Chemical class 0.000 claims description 2
150000004820 halides Chemical group 0.000 claims description 2
150000004679 hydroxides Chemical group 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
CCEFMUBVSUDRLG-UHFFFAOYSA-N limonene-1,2-epoxide Chemical compound C1C(C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-UHFFFAOYSA-N 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
239000011572 manganese Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 claims description 2
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 2
235000011007 phosphoric acid Nutrition 0.000 claims description 2
150000003016 phosphoric acids Chemical class 0.000 claims description 2
229920001515 polyalkylene glycol Polymers 0.000 claims description 2
229920001610 polycaprolactone Polymers 0.000 claims description 2
239000004632 polycaprolactone Substances 0.000 claims description 2
229920005650 polypropylene glycol diacrylate Polymers 0.000 claims description 2
ZZPKLSNHENDBHJ-UHFFFAOYSA-N prop-2-enoic acid 1,3,5-triazine-2,4,6-triamine Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.NC1=NC(N)=NC(N)=N1 ZZPKLSNHENDBHJ-UHFFFAOYSA-N 0.000 claims description 2
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 2
AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 claims description 2
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
229910000077 silane Inorganic materials 0.000 claims description 2
JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 claims description 2
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims 1
GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims 1
YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 claims 1
NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims 1
239000004342 Benzoyl peroxide Substances 0.000 claims 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
VLGKAALXQUYBDZ-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO.CCC(CO)(CO)CO.C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO.CCC(CO)(CO)CO.C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C VLGKAALXQUYBDZ-UHFFFAOYSA-N 0.000 claims 1
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims 1
235000019400 benzoyl peroxide Nutrition 0.000 claims 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
150000003014 phosphoric acid esters Chemical class 0.000 claims 1
229920005989 resin Polymers 0.000 abstract description 24
239000011347 resin Substances 0.000 abstract description 24
239000011248 coating agent Substances 0.000 description 17
238000012360 testing method Methods 0.000 description 12
239000004925 Acrylic resin Substances 0.000 description 10
238000007792 addition Methods 0.000 description 9
239000000370 acceptor Substances 0.000 description 8
238000004132 cross linking Methods 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
239000000178 monomer Substances 0.000 description 7
241000894007 species Species 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
229910000831 Steel Inorganic materials 0.000 description 5
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
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238000006957 Michael reaction Methods 0.000 description 3
125000005410 aryl sulfonium group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012955 diaryliodonium Substances 0.000 description 3
125000005520 diaryliodonium group Chemical group 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
239000003999 initiator Substances 0.000 description 3
238000010030 laminating Methods 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
230000015843 photosynthesis, light reaction Effects 0.000 description 3
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238000003786 synthesis reaction Methods 0.000 description 3
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 2
IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 2
POLZHVHESHDZRD-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate;phosphoric acid Chemical compound OP(O)(O)=O.CC(=C)C(=O)OCCO POLZHVHESHDZRD-UHFFFAOYSA-N 0.000 description 2
239000007848 Bronsted acid Substances 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 2
150000004729 acetoacetic acid derivatives Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
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238000005516 engineering process Methods 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
238000009740 moulding (composite fabrication) Methods 0.000 description 2
ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
230000002028 premature Effects 0.000 description 2
238000007639 printing Methods 0.000 description 2
230000008569 process Effects 0.000 description 2
238000003847 radiation curing Methods 0.000 description 2
238000010526 radical polymerization reaction Methods 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
229920001187 thermosetting polymer Polymers 0.000 description 2
125000005409 triarylsulfonium group Chemical group 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
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 1
YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 1
ZDMZLTIFXMREFI-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate;phosphoric acid Chemical compound OP(O)(O)=O.OCCOC(=O)C=C ZDMZLTIFXMREFI-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000819038 Chichester Species 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
238000003848 UV Light-Curing Methods 0.000 description 1
XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
SMTUJUHULKBTBS-UHFFFAOYSA-N benzyl(trimethyl)azanium;methanolate Chemical compound [O-]C.C[N+](C)(C)CC1=CC=CC=C1 SMTUJUHULKBTBS-UHFFFAOYSA-N 0.000 description 1
DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000004891 communication Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
238000013036 cure process Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
238000005034 decoration Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000001879 gelation Methods 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
230000008821 health effect Effects 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000010667 large scale reaction Methods 0.000 description 1
PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
238000007040 multi-step synthesis reaction Methods 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
150000004010 onium ions Chemical class 0.000 description 1
230000035515 penetration Effects 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
239000012953 triphenylsulfonium Substances 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
210000002268 wool Anatomy 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
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/13—Morphological aspects
- C08G2261/135—Cross-linked structures
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/76—Post-treatment crosslinking

Definitions

Michael polyacrylate resin also termed Michael oligomer, Michael adduct, or Michael addition product
TMPTA Trimethylolpropane triacrylate
DBU diazabicycloundecene
EAA Ethyl acetoacetate

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Adhesives Or Adhesive Processes (AREA)
Paints Or Removers (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

EP04810830A 2003-11-14 2004-11-12 Dual-cure-reaktionsprodukte von selbstphotoinitiierenden multifunktionellen acrylaten mit cycloaliphatischen epoxidverbindungen Withdrawn EP1685193A4 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10/712,044 US7041749B2 (en)	2002-12-17	2003-11-14	Dual cure reaction products of self-photoinitiating multifunction acrylates with cycloaliphatic epoxy compounds
PCT/US2004/037807 WO2005048866A2 (en)	2003-11-14	2004-11-12	Dual cure reaction products of self-photoinitiating multifunctional acrylates with cycloaliphatic epoxy compounds

Publications (2)

Publication Number	Publication Date
EP1685193A2 EP1685193A2 (de)	2006-08-02
EP1685193A4 true EP1685193A4 (de)	2006-12-13

Family

ID=34619849

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP04810830A Withdrawn EP1685193A4 (de)	2003-11-14	2004-11-12	Dual-cure-reaktionsprodukte von selbstphotoinitiierenden multifunktionellen acrylaten mit cycloaliphatischen epoxidverbindungen

Country Status (7)

Country	Link
EP (1)	EP1685193A4 (de)
JP (1)	JP2007511641A (de)
KR (1)	KR20070097294A (de)
CN (1)	CN1910234A (de)
BR (1)	BRPI0416519A (de)
CA (1)	CA2545998A1 (de)
WO (1)	WO2005048866A2 (de)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4888766B2 (ja) *	2006-07-11	2012-02-29	日東電工株式会社	多官能化合物の製造方法
GB0700960D0 (en) *	2007-01-18	2007-02-28	3M Innovative Properties Co	High strength epoxy adhesive and uses thereof
JP5676444B2 (ja)	2008-07-23	2015-02-25	スリーエムイノベイティブプロパティズカンパニー	二液型エポキシ系構造接着剤
EP2310436B1 (de)	2008-07-23	2012-12-26	3M Innovative Properties Company	Zweikomponentige konstruktionsklebstoffe auf epoxidbasis
US8637614B2 (en)	2008-07-23	2014-01-28	3M Innovative Properties Company	Reactive liquid modifiers
CN102311520A (zh) *	2011-08-05	2012-01-11	大连方盛塑料有限公司	一种热塑性塑料
WO2013050622A1 (en)	2011-10-07	2013-04-11	Nuplex Resins B.V.	A crosslinkable composition cross-linkable by real michael addition reaction and resins for use in said composition
PL2822381T3 (pl) *	2012-03-05	2020-09-21	Archer Daniels Midland Company	Zastosowanie mikroemulsji jako układów dostarczania
JP6183642B2 (ja)	2012-08-10	2017-08-23	株式会社リコー	活性光線硬化組成物、並びにこれを用いた活性光線硬化型インクジェット印刷用インク組成物及び活性光線硬化型接着剤組成物
EP2984133B1 (de)	2013-04-08	2018-03-28	Allnex Netherlands B.V.	Zusammensetzung vernetzbar durch reale michael addition reaction (rma)
PL3201261T3 (pl) *	2014-10-01	2019-07-31	Basf Se	Sposób utwardzania utwardzalnych kompozycji
CA2983148C (en)	2015-04-17	2023-05-09	Allnex Netherlands B.V.	Process for the manufacture of a crosslinkable composition
JP6837991B2 (ja)	2015-04-17	2021-03-03	オールネックス・ネザーランズ・ビー．ブイ．ＡｌｌｎｅｘＮｅｔｈｅｒｌａｎｄｓＢ．Ｖ．	フロアコーティング組成物
CA2983155C (en)	2015-04-17	2022-03-08	Allnex Netherlands B.V.	Modified epoxy primer for improved adhesion of rma crosslinkable coating compositions
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Publication number	Publication date
EP1685193A2 (de)	2006-08-02
CN1910234A (zh)	2007-02-07
CA2545998A1 (en)	2005-06-02
KR20070097294A (ko)	2007-10-04
BRPI0416519A (pt)	2007-03-06
JP2007511641A (ja)	2007-05-10
WO2005048866A3 (en)	2005-09-15
WO2005048866A2 (en)	2005-06-02

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