WO2022185086A1 - (méth)acrylate d'uréthane et compositions associées pour une charge supérieure - Google Patents
(méth)acrylate d'uréthane et compositions associées pour une charge supérieure Download PDFInfo
- Publication number
- WO2022185086A1 WO2022185086A1 PCT/IB2021/000126 IB2021000126W WO2022185086A1 WO 2022185086 A1 WO2022185086 A1 WO 2022185086A1 IB 2021000126 W IB2021000126 W IB 2021000126W WO 2022185086 A1 WO2022185086 A1 WO 2022185086A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- urethane
- formula
- linker
- Prior art date
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 209
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 238000011068 loading method Methods 0.000 title description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 57
- 150000002009 diols Chemical class 0.000 claims abstract description 47
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 26
- 125000005647 linker group Chemical group 0.000 claims description 90
- -1 polyoxyethylene Polymers 0.000 claims description 89
- 229920000570 polyether Polymers 0.000 claims description 53
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 51
- 229920000728 polyester Polymers 0.000 claims description 37
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 229920001223 polyethylene glycol Polymers 0.000 claims description 23
- 239000002202 Polyethylene glycol Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 229920001451 polypropylene glycol Polymers 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000005062 Polybutadiene Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 229920002857 polybutadiene Polymers 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 229920001610 polycaprolactone Polymers 0.000 claims description 7
- 239000004632 polycaprolactone Substances 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- 239000008199 coating composition Substances 0.000 claims description 4
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 2
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 2
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 2
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 claims description 2
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 claims description 2
- 238000010146 3D printing Methods 0.000 claims description 2
- IXQBIOPGDNZYNA-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C IXQBIOPGDNZYNA-UHFFFAOYSA-N 0.000 claims description 2
- SGXQOOUIOHVMEJ-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCCCCCCCC Chemical compound N=C=O.N=C=O.CCCCCCCCCCCC SGXQOOUIOHVMEJ-UHFFFAOYSA-N 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 229920005862 polyol Polymers 0.000 description 35
- 150000003077 polyols Chemical class 0.000 description 35
- 239000000178 monomer Substances 0.000 description 34
- 239000011572 manganese Substances 0.000 description 14
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 12
- 229920005906 polyester polyol Polymers 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 10
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 9
- 239000004814 polyurethane Substances 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- 150000005846 sugar alcohols Chemical class 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 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 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 8
- 239000000976 ink Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 125000004386 diacrylate group Chemical group 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 229920001515 polyalkylene glycol Polymers 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- 238000007142 ring opening reaction Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 244000028419 Styrax benzoin Species 0.000 description 5
- 235000000126 Styrax benzoin Nutrition 0.000 description 5
- 235000008411 Sumatra benzointree Nutrition 0.000 description 5
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound 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 description 5
- 150000007824 aliphatic compounds Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 235000019382 gum benzoic Nutrition 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 4
- JMMSLMMJRMCXPW-UHFFFAOYSA-N OC.OC.C1CC2CCC1C2 Chemical compound OC.OC.C1CC2CCC1C2 JMMSLMMJRMCXPW-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical class CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 229940043375 1,5-pentanediol Drugs 0.000 description 3
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052770 Uranium Inorganic materials 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
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- 229960002130 benzoin Drugs 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 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 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
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- CQAIBOSCGCTHPV-UHFFFAOYSA-N bis(1-hydroxycyclohexa-2,4-dien-1-yl)methanone Chemical class C1C=CC=CC1(O)C(=O)C1(O)CC=CC=C1 CQAIBOSCGCTHPV-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
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 150000001634 bornane-2,3-dione derivatives Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- INDXRDWMTVLQID-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO.OCCCCO INDXRDWMTVLQID-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 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
- 238000004364 calculation method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- FXNONNRUNQPNLF-UHFFFAOYSA-N cerium;2-ethylhexanoic acid Chemical compound [Ce].CCCCC(CC)C(O)=O.CCCCC(CC)C(O)=O.CCCCC(CC)C(O)=O FXNONNRUNQPNLF-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000001514 detection method Methods 0.000 description 1
- GRBFCEINWFRDOG-UHFFFAOYSA-K di(octadecanoyloxy)bismuthanyl octadecanoate Chemical compound [Bi+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O GRBFCEINWFRDOG-UHFFFAOYSA-K 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- SNVTZAIYUGUKNI-UHFFFAOYSA-N dibenzo[1,2-a:1',2'-e][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC=CC=C21 SNVTZAIYUGUKNI-UHFFFAOYSA-N 0.000 description 1
- PQWINHWBRIYBSP-UHFFFAOYSA-N dibutyltin(2+) Chemical class CCCC[Sn+2]CCCC PQWINHWBRIYBSP-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NRHMQDVIKPCCRT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO NRHMQDVIKPCCRT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- GNNILMDCYQGMRH-UHFFFAOYSA-N formyl benzoate Chemical class O=COC(=O)C1=CC=CC=C1 GNNILMDCYQGMRH-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002505 iron Chemical class 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
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- MLOKPANHZRKTMG-UHFFFAOYSA-N lead(2+);oxygen(2-);tin(4+) Chemical compound [O-2].[O-2].[O-2].[Sn+4].[Pb+2] MLOKPANHZRKTMG-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OMKZWUPRGQMQJC-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCNCCCN OMKZWUPRGQMQJC-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- OURNLUUIQWKTRH-UHFFFAOYSA-N oxirane;phenol Chemical class C1CO1.OC1=CC=CC=C1.OC1=CC=CC=C1 OURNLUUIQWKTRH-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GYUPBLLGIHQRGT-UHFFFAOYSA-N pentane-2,4-dione;titanium Chemical compound [Ti].CC(=O)CC(C)=O GYUPBLLGIHQRGT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- QCVVTFGMXQFNJW-UHFFFAOYSA-M potassium;7,7-dimethyloctanoate Chemical compound [K+].CC(C)(C)CCCCCC([O-])=O QCVVTFGMXQFNJW-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- DVSILEVINNCNTQ-UHFFFAOYSA-L zinc;3-oxobutanoate Chemical compound [Zn+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O DVSILEVINNCNTQ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
- C08F299/065—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes from polyurethanes with side or terminal unsaturations
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/6725—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing ester groups other than acrylate or alkylacrylate ester groups
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8166—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with unsaturated monofunctional alcohols or amines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
Definitions
- the present invention relates to a urethane (meth)acrylate obtained by using a specific combination of hydroxylated (meth)acrylates, a diisocyanate and a diol, as well as its manufacturing process.
- the present invention also relates to a curable composition comprising the urethane (meth)acrylate and to a cured product obtained by curing the urethane (meth)acrylate or the curable composition.
- Urethane (meth)acrylates are widely known in photocurable resins to provide mechanical toughness to the system.
- urethane (meth)acrylates typically exhibit very viscous behavior at regular handling temperatures (10-30°C) due to their urethane linkages. The high viscosity is also observed with urethane (meth)acrylates having a moderate molecular weight.
- Formulators cannot use too much highly viscous component in most applications, in particular flowable process applications like inks and coatings. Accordingly, the loading amount of conventional urethane (meth)acrylates in such formulations is limited and the advantageous effect on mechanical properties cannot be fully obtained. In this sense, it would be advantageous to have urethane (meth)acrylates with low viscosity since higher content could be loaded in applicative formulations thus broadening the freedom of blend design and improving the mechanical properties of the cured products obtained therefrom.
- W09118033 discloses a reactive liquid resin for hybrid urethane resin network, having a viscosity at 23°C in the range of 1 to 150 mPa.s fa injection molding.
- Said resin is a mixture of three components a polyisocyanate, a first ethylenically unsaturated monomer bearing an isocyanate-reactive group (OH) with a molecular weight lower than 500 g/mol, preferably lower than 400 g/mol, and a second ethylenically unsaturated monomer copolymerizable with the 1 st one.
- a hybrid urethane network is formed by reaction of the polyisocyanate with the isocyanate-reactive groups (OH) of the copolymer, which is formed by radical copolymerization between said first isocyanate-reactive ethylenically unsaturated monomer and said second ethylenically unsaturated monomer, leading to a hybrid network comprising urethane crosslinks.
- the viscosity of the resin is kept low (1-150 mPa.s at 23 °C) by limiting the molecular weight of the reactive components and, in particular, of the isocyanate-reactive monomer to less than 500 g/mol, preferably less than 400 g/mol.
- the reactive resin disclosed in W09118033 does not include a polymeric diol and after copolymerization of the ethylenic unsaturations, there are no remaining ethylenic unsaturations in the formed copolymer or in the resulting urethane crosslinked network. As such, W09118033 does not disclose a urethane (meth)acrylate polymer (non-crosslinked structure).
- JP4013532 discloses a polyurethane (meth)acrylate component C) for increasing the viscosity and adhesion of curable compositions for optical applications on specific supports, without affecting hardness and transparency.
- This component C) is obtained from the reaction of a polyisocyanate with a diol having from 1 to 5 alkoxy units in C2-C4 and a monoalcohol bearing at least two (meth)acryloyl groups.
- the molar ratio of polyisocyanate to diol in said polyurethane (meth)acrylate component is from 3:2 to 21 :20.
- the main objective of the present invention is finding new UAs with a tailored structure in terms of the location of urethane bonds (repeating units) and their contents with specific repeating and terminal units, so that the viscosity is lower with respect to UA known from prior art not having these specific structural characteristics, while enabling satisfactory mechanical performances for the related UA cured compositions.
- the low viscosity of the urethane (meth)acrylates of the invention compared to those of the prior art enables formulators to load higher amount into their formulation and/or to facilitate the processing of the formulation. Higher amounts of urethane (meth)acrylate also enables broader freedom in designing formulations and better mechanical performances after curing. Summary of the invention
- a first object of the present invention is a urethane (meth)acrylate of formula (I): wherein A, A’, B, D, Ri, R’i, a, a’ and b are as defined herein, and the weight content of urethane bonds in the urethane (meth)acrylate is from 5 to 20% based on the total weight of the urethane (meth)acrylate.
- a second object of the present invention is a curable composition comprising the urethane (meth)acrylate of the invention.
- Another object of the present invention is a preparation process of the urethane (meth)acrylate of the invention.
- Another object of the present invention is the use of the urethane (meth)acrylate of the invention or the curable composition of the present invention.
- Yet another object of the present invention is a cured product resulting from the cure of the urethane (meth)acrylate of the invention or the curable composition of the present invention .
- % by weight in a compound or a composition are expressed based on the weight of the compound, respectively of the composition.
- diisocyanate » means a compound bearing two isocyanate groups.
- diol » means a compound bearing two hydroxyl groups.
- hydroxylated (meth)acrylate means a compound bearing one hydroxyl group and at least one (meth)acrylate group.
- hydroxyl group » means a group of formula -OH.
- alkyl » means a monovalent saturated alicyclic hydrocarbon group of formula -C X H 2X+I wherein x is 1 to 20.
- An alkyl may be linear or branched.
- alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, 2-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 2,2-dimethylbutyl, n-heptyl, 2-ethylhexyl, and the like.
- C2-C12 alkylene refers to a saturated divalent radical derived from an alkane comprising 2 to 12 carbon atoms.
- linker » means a plurivalent group.
- a linker may connect at least two moieties of a compound together.
- a linker that connects two moieties of a compound together may be referred to as a divalent linker.
- hydrocarbon linker » means a linker having a carbon backbone chain which may optionally be interrupted by one or more heteroatoms selected from N, O, S, Si and mixtures thereof.
- a hydrocarbon linker may be aliphatic, cycloaliphatic or aromatic.
- a hydrocarbon linker may be saturated or unsaturated.
- a hydrocarbon linker may be optionally substituted.
- cycloaliphatic compound » or « cycloaliphatic linker » means a compound, respectively a linker, comprising a non-aromatic ring.
- the non-aromatic ring may have only carbon atoms as the ring atoms (i.e. a cycloalkyl) or it may comprise carbon atoms and one or more heteroatoms selected from N, O and S as ring atoms (i.e. an heterocycloalkyl). It may be substituted by one or more groups as defined for aliphatic compounds and linkers. It may comprise one or more bonds as defined for aliphatic compounds and linkers.
- aromatic compound » or « aromatic linker » means a compound, respectively a linker, comprising an aromatic ring (i.e. a ring that respects Huckel’s aromaticity rule).
- the aromatic ring may have only carbon atoms as the ring atoms (i.e. an aryl, such as a phenyl) or it may comprise carbon atoms and one or more heteroatoms selected from N, O and S as ring atoms (i.e. an heteroaryl). It may be substituted by one or more groups as defined for aliphatic compounds and linkers. It may comprise one or more bonds as defined for aliphatic compounds and linkers.
- Araliphatic compounds and linkers ie. compounds and linkers comprising both an aromatic moiety and an aliphatic moiety are encompassed by aromatic compounds and linkers.
- saturated » means a compound that does not comprise any double or triple carbon-carbon bonds.
- unsaturated » means a compound that comprises a double or triple carbon- carbon bond, in particular a double carbon-carbon bond.
- polyol » means a compound comprising at least two hydroxyl groups.
- polyether polyol » « polyether diol » or « polyether linker » means respectively a polyol, a diol or a linker comprising at least two ether bonds.
- polyester polyol » « polyester diol » or « polyester linker » means respectively a polyol, a diol or a linker comprising at least two ester bonds.
- polycarbonate polyol » or « polycarbonate linker » means a polyol, respectively a linker, comprising at least two carbonate bonds.
- ether bond » means a -O- bond.
- the urethane (meth)acrylate of the invention corresponds to the following formula (I): wherein
- a and A’ are independently selected from a polyether linker, a polyester linker and combinations thereof;
- B is divalent linker
- D is a divalent linker
- Ri and R’i are independently H or methyl; a and a’ are independently from 1 to 5; b is from 1 to 5.
- the weight content of urethane bonds may be from 5.5 to 17%, from 6 to 15%, from 6.5 to 14.5%, from 7 to 14%, from 7 to 13%, from 7 to 12%, from 7 to 11%, from 7 to 10% or from 7 to 9%, based on the total weight of the urethane (meth)acrylate.
- the molecular weight ratios R A and R A ’ may both be at least 0.25, wherein
- MP A is the number average molecular weight of a hydroxylated (meth)acrylate of formula (II) that may be used to obtain the terminal moiety of formula (III) of the urethane (meth)acrylate: wherein A, FT and a are as defined herein;
- MP A ’ is the number average molecular weight of a hydroxylated (meth)acrylate of formula (IV) that may be used to obtain the terminal moiety of formula (V) of the urethane (meth)acrylate: wherein A’, R’i and a’ are as defined herein;
- Mn D is the number average molecular weight of a diol of formula (VI) that may be used to obtain the central moiety of formula (VII) of the urethane (meth)acrylate:
- the molecular weight ratios R A and R A ’ may both independently be from 0.25 to 2, from 0.26 to 1.9, from 0.27 to 1 .8, from 0.28 to 1.7, from 0.3 to 1.6, from 0.4 to 1 .5, from 0.5 to 1.4 or from 0.6 to 1 .3.
- the number average molecular weights MP A and MP A ’ may each independently be at least 250 g/mol, preferably from 250 to 3000 g/mol, more preferably from 300 to 2500 g/mol, more preferably still from 340 to 2000 g/mol.
- the number molecular weight may be determined according to the method described herein.
- a and a’ is independently from 1 to 5.
- a and a’ may independently be from 1 to 3, from 1 to 2, or a and a’ may both be 1 .
- the urethane (meth)acrylate of the invention may bear from 2 to 10, in particular 2 to 6, more particularly 2 to 4, even more particularly 2, (meth)acrylate groups. All of the (meth)acrylate groups of the urethane (meth)acrylate polymer may be carried by residues A and A’. Accordingly, residue D may be free of any (meth)acrylate group.
- the value of b is from 1 to 5. In particular, b may be from 1 to 4, from 1 to 3, from 1 to 2 or b may be 1 .
- a and A’ are independently selected from a polyether linker, a polyester linker and combinations thereof.
- a and A’ may be identical or different. In one embodiment, A and A’ are identical. In another embodiment, A and A’ are different.
- a can a polyether linker and A’ can be a different polyether linker.
- a can be a polyether linker and A’ can be a polyester linker.
- a can be a polyester linker and A’ can be a different polyester linker.
- a and A’ may be a polyether linker comprising at least 6 ether bonds.
- the polyether linker may comprise from 6 to 50, from 6 to 30 or from 10 to 20 ether bonds.
- the ether bonds may be comprised in oxyalkylene repeating units.
- An oxyalkylene repeating unit may correspond to -[0-(CR 2 R’ 2 ) c ]- wherein each R 2 and R’ 2 is independently H or methyl and c is 2 to 4.
- the oxyalkylene repeating units may be selected from oxyethylene (-0-CH 2 -CH 2 -), oxypropylene (-0-CH 2 -CH(CH 3 )- and/or -0-CH(CH 3 )-CH 2 -), oxybutylene (-0- CH 2 -CH 2 -CH 2 -CH 2 -), and mixtures thereof.
- the polyether linker may be the residue, without the OH groups, of an alkoxylated (i.e. ethoxylated, propoxylated and/or butoxylated) polyol POH.
- suitable polyols POH include 1 ,2-ethylene glycol, 1 ,2- or 1 ,3-propylene glycol, 1 ,2- 1 ,3- or 1 ,4-butylene glycol, 1 ,5- pentanediol, 1 ,6-hexanediol, 1 ,7-heptanediol, 1 ,8-octanediol, 1 ,9-nonanediol, 1 ,10- decanediol, 1 ,12-dodecanediol, 2-methyl-1 ,3-propanediol, 2, 2-diethyl-1 ,3-propanediol, 3- methyl-1 ,5-pentaned
- polyether linker may correspond to formula (VIII) or (IX): -(CR 2 R’ 2 ) c -[0-(CR 2 R’ 2 )c]d- (VIII)
- each R 2J R’ 2J R 3J R’ 3J R S and R’ 5 is independently H or methyl; each R 4 and R’ 4 is independently H or alkyl; c, e and e’ are independently 2 to 4; d is from 6 to 50, from 6 to 30 or from 10 to 20; f and f are independently 0 to 50, with the proviso that the sum f + f is from 6 to 50, from 6 to 30 or from 10 to 20; g is 2 to 20.
- the polyether linker may be selected from a polyoxyethylene, a polyoxypropylene, a polyoxybutylene, a co-poly(oxyethylene-oxypropylene), a co- poly(oxyethylene-oxybutylene), a co-poly(oxypropylene-oxybutylene), in particular a polyoxypropylene.
- the polyether linker may correspond to the residue, without the OH groups, of a polyalkylene glycol.
- suitable polyalkylene glycols include a polyethylene glycol, a polypropylene glycol, a polytetramethylene glycol, a polyethylene glycol-co-propylene glycol), a polyethylene glycol-co-tetramethylene glycol) and a poly(propylene glycol-co- tetramethylene glycol).
- the polyalkylene glycol may be a polypropylene glycol.
- a and A’ may be a polyester linker comprising at least 2 ester bonds.
- the polyester linker may comprise from 2 to 20, from 2 to 10 or from 2 to 7 ester bonds.
- the ester bonds may be comprised in repeating units derived from the ring-opening of a lactone, in particular e-caprolactone or d-valerolactone.
- the polyester linker may be the residue, without the OH groups, of a polyol POH which is esterified with repeating units derived from the ring-opening of a lactone.
- suitable polyols POH are as defined above for the polyether linker.
- the polyester linker may be the residue, without the OH groups, of a polyester polyol obtained by reacting a polyol POH with a polycarboxylic acid, a cyclic anhydride or a derivative thereof, in particular a dicarboxylic acid or a cyclic anhydride.
- suitable polyols POH are as defined above for the polyether linker.
- polycarboxylic acids examples include adipic acid, succinic acid, oxalic acid, malonic acid, pimelic acid, suberic acid, sebacic acid, dodecanedioic acid, eicosanedioic acid, cyclohexane dicarboxylic acid, hexahydrophthalic acid, itaconic acid, fumaric acid, maleic acid and the like.
- Aromatic diacids such as phthalic acid and terephthalic acid could also be utilized.
- Suitable cyclic anhydrides include succinic anhydride, hexahydrophthalic anhydride, maleic anhydride, fumaric anhydride, tetrahydrophthalic anhydride, phthalic anhydride.
- Derivatives of polycarboxylic acids are compounds that are able to transform in polycarboxylic acid by hydrolysis or transesterification. Suitable examples include dimethylmalonate, diethylmalonate, dimethyladipate, dimethyl glutarate and dimethyl succinate.
- polyester linker may correspond to formula (X) or (XI):
- E is C2-C20 alkylene or -[(CR6R’6)iO]i -(CR 6 R’6)i- each Re and R’e is independently H or methyl; each R 7 , R’ 7J R 8 and R’ 8 is independently H or alkyl; g is 3 to 10, in particular 4 to 6, more particularly 5; h and h’ are independently 0 to 20, in particular 2 to 10, more particularly 2 to 7, with the proviso that the sum h + h’ is at least 2; i is 2 to 4, in particular 2; i * is 1 to 10, in particular 1 to 5, more particularly 1 to 3; j is 2 to 20, in particular 2 to 12, more particularly 2 to 8; k is 1 to 36, in particular 1 to 20, more particularly 1 to 12;
- I is 1 to 20, in particular 2 to 15, more particularly 2 to 10.
- the polyester linker may correspond to formula (X) and h is 0 and h’ is at least 2 or h is at least 2 and h’ is 0;
- E is a C2-20 alkylene, in particular a C2-12 alkylene, more particularly a C2-C6 alkylene.
- terminal moieties of formula (III) and (V) of the urethane (meth)acrylate of the invention may be the residues, without the hydrogen atom of the hydroxyl group, of hydroxylated (meth)acrylates of formula (II) and (IV): wherein A, A’, Ri, R’i, a and a’ are as defined herein.
- the hydroxylated (meth)acrylates of formula (II) and (IV) bear a single OH group. More particularly, the hydroxylated (meth)acrylates of formula (II) and (IV) bear a single OH group and a single (meth)acrylate group (i.e. a and a’ are both 1).
- the hydroxylated (meth)acrylates of formula (II) and (IV) may thus be polyethers or polyesters bearing a single OH group and a single (meth)acrylate group.
- These compounds may be obtained by reacting a polyether diol or a polyester diol with a (meth)acrylate acid or (meth)acryloyl chloride using an appropriate molar ratio so that a single free hydroxyl group remains on the resulting product.
- the hydroxylated (meth)acrylates of formula (II) and (IV) may be selected from a polyethylene glycol (meth)acrylate, a polypropylene glycol (meth)acrylate, a polytetramethylene glycol (meth)acrylate, a polyethylene glycol-co-propylene glycol) (meth)acrylate, a polycaprolactone (meth)acrylate and combinations thereof.
- hydroxylated (meth)acrylates of formula (II) and (IV) may be selected from a hydroxylated polyether (meth)acrylate of formula (XII), a hydroxylated polyester (meth)acrylate of formula (XIII), and combinations thereof: wherein
- Rio is H or CH 3J in particular H; each Rg and R’g is independently H or CH 3 ; each I is independently 2 to 4, in particular 2; m is 6 to 50, in particular 6 to 30, more particularly 10 to 20; wherein
- Rii is H or CH 3 , in particular H;
- Li is a linear or branched C2-C12 alkylene, in particular a linear C2-C4 alkylene, more particularly ethylene; o is 2 to 20, in particular 2 to 10, more particularly 2 to 7; even more particularly 2 and n is 3 to 10, in particular 4 to 6, more particularly 5.
- a hydroxylated polyether (meth)acrylate of formula (XII) may be prepared by reaction between a polyalkylene glycol (such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol or copolymers thereof, in particular polyethylene glycol or polypropylene glycol) with (meth)acrylic acid or (meth)acryloyl chloride.
- a polyalkylene glycol such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol or copolymers thereof, in particular polyethylene glycol or polypropylene glycol
- a hydroxylated polyester (meth)acrylate of formula (XIII) may be prepared by reaction between a hydroxyalkyl (meth)acrylate (such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate or 4-hydroxybutyl (meth)acrylate, in particular 2-hydroxyethyl (meth)acrylate) and a lactone (such as d-valerolactone or e-caprolactone, in particular e-caprolactone).
- a hydroxyalkyl (meth)acrylate such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate or 4-hydroxybutyl (meth)acrylate, in particular 2-hydroxyethyl (meth)acrylate
- a lactone such as d-valerolactone or e-caprolactone, in particular e-caprolactone
- Some of these compounds are commercially available, such as a polyethylene glycol acrylate in the NOF Blemmer ® AE series, a polypropylene oxide acrylate in the NOF Blemmer AP® series, a polycaprolactone acrylate with 2 units derived from the ring opening e-caprolactone sold under reference SR495 by Sartomer.
- B is divalent linker.
- B is an aliphatic, cycloaliphatic or aromatic hydrocarbon linker. More particularly, B is a cycloaliphatic hydrocarbon linker B may be the residue, without the NCO groups, of a diisocyanate of formula (XIV): OCN-B-NCO (XIV).
- the diisocyanate of formula (XIV) may be an aliphatic, cycloaliphatic or aromatic diisocyanate, in particular a cycloaliphatic diisocyanate.
- the diisocyanate of formula (XIV) may be selected from the group consisting of isophorone diisocyanate (IPDI - corresponding to 3-isocyanatomethyl-3,5,5- trimethylcyclohexylisocyanate), 2,4- and 2,6-toluene diisocyanate (TDI), tetramethylene diisocyanate, pentamethylene diisocyanate (PDI), hexamethylene diisocyanate (HMDI), dodecane diisocyanate, trimethylhexamethylene diisocyanate (TMDI), 2,2'-, 2,4'- and 4,4'- diphenylmethane diisocyanate (MDI), 2,2'-, 2,4'- and 4,4'-dicyclohexylmethane diisocyanate (H12MDI), m-xylylene diisocyanate, 1 ,5-naphthalene diisocyanate (NDI), 1 ,3
- the diisocyanate of formula (XIV) is IPDI.
- D is divalent linker.
- D may be selected from an aromatic, aliphatic or cycloaliphatic hydrocarbon linker, a polyether linker, a polyester linker, a polycarbonate linker, a polybutadiene linker, and combinations thereof.
- D may be free of (meth)acrylate groups.
- D may be free of siloxane groups (i.e. groups comprising a Si-0 bond).
- D may be a linker that does not comprise any pending groups other than alkyl.
- D may be selected from a polyether linker, a polyester linker and combinations thereof.
- the polyether linker may comprise at least 2 ether bonds.
- the polyether linker may comprise from 2 to 50, from 4 to 30 or from 6 to 20 ether bonds.
- the ether bonds may be comprised in oxyalkylene repeating units as defined above.
- the polyether linker may be the residue, without the OH groups, of an alkoxylated (i.e. ethoxylated, propoxylated and/or butoxylated) diol DOH.
- suitable diols DOH include 1 ,2-ethylene glycol, 1 ,2- or 1 ,3-propylene glycol, 1 ,2- 1 ,3- or 1 ,4-butylene glycol, 1 ,5- pentanediol, 1 ,6-hexanediol, 1 ,7-heptanediol, 1 ,8-octanediol, 1 ,9-nonanediol, 1 ,10- decanediol, 1 ,12-dodecanediol, 2-methyl-1 ,3-propanediol, 2, 2-diethyl-1 ,3-propanediol, 3- methyl-1 ,5-pentaned
- polyether linker may correspond to formula (VIII) or (IX) as defined above.
- the polyether linker may be selected from a polyoxyethylene, a polyoxypropylene, a polyoxybutylene, a co-poly(oxyethylene-oxypropylene), a co- poly(oxyethylene-oxybutylene), a co-poly(oxypropylene-oxybutylene).
- the polyether linker may correspond to the residue, without the OFI groups, of a polyalkylene glycol.
- suitable polyalkylene glycols include a polyethylene glycol, a polypropylene glycol, a polytetramethylene glycol, a polyethylene glycol-co-propylene glycol), a polyethylene glycol- co-tetramethylene glycol) and a poly(propylene glycol-co-tetramethylene glycol).
- the polyester linker may comprise at least 2 ester bonds.
- the polyester linker may comprise from 2 to 20, from 2 to 10 or from 2 to 7 ester bonds.
- the ester bonds may be comprised in repeating units derived from the ring-opening of a lactone as defined above.
- the polyester linker may be the residue, without the OFI groups, of a diol DOH which is esterified with repeating units derived from the ring-opening of a lactone.
- suitable diols DOH are as defined above for the polyether linker.
- the polyester linker may be the residue, without the OFI groups, of a polyester polyol obtained by reacting a diol DOH with a polycarboxylic acid functional compound or a derivative thereof, in particular a dicarboxylic acid or a cyclic anhydride.
- a diol DOH with a polycarboxylic acid functional compound or a derivative thereof, in particular a dicarboxylic acid or a cyclic anhydride.
- suitable diols DOH are as defined above for the polyether linker.
- suitable polycarboxylic acid functional compounds are as defined above.
- polyester linker may correspond to formula (X) or (XI) as defined above.
- D may be the residue, without the OFI groups, of a diol of formula (VI)
- the diol of formula (VI) may be selected from a polyester diol, a polyether diol and mixtures thereof, preferably a polyether diol.
- the polyester diol may be an aliphatic polyester diol, preferably a polycaprolactone diol.
- the polyether diol may be selected from the group consisting of a polyethylene glycol, a polypropylene glycol or polytetramethylene glycol, preferably a polytetramethylene glycol.
- Suitable polytetramethylene glycols include a homopolymer of THF (tetrahydrofuran) and its copolymeric form with a THF substituted with an alkyl in C1-C4.
- the number average molecular weight Mn D of the diol of formula (VI) may be from 300 to 3000 g/mol, in particular from 500 to 2500 g/mol, more particularly from 600 to 2000 g/mol.
- the urethane (meth)acrylate polymer of the invention advantageously exhibits a Brookfield viscosity at 60°C lower than 4500 mPa.s, in particUar from 50 to 4000 mPa.s, more particularly from 100 to 3500 mPa.s.
- the viscosity may be measured according to the method disclosed herein.
- Another subject-matter of the invention relates to a process of preparing a urethane (meth)acrylate of formula (I) as defined above, wherein the process comprises reacting hydroxylated (meth)acrylates of formula (II) and (IV), a diol of formula (VI) and a diisocyanate of formula (XIV) in one or more steps.
- Components of formulae (II), (IV), (VI) and (XIV) may be as defined above for the urethane (meth)acrylate.
- the molar ratio NCO/OH may be from 0.95 to 1 .05.
- the molar ratio NCO/OH corresponds to the molar ratio between the NCO groups of the diisocyanate of formula (XIV) and the OH groups of the hydroxylated (meth)acrylates of formula (II) and (IV) and the diol of formula (VI).
- the process comprises the step of mixing and reacting components of formulae (II), (IV), (VI) and (XIV) all together.
- the process comprises the following successive steps: i) reacting a diisocyanate of formula (XIV) with a diol of formula (VI); and ii) adding to the resulting product of step i) hydroxylated (meth)acrylates of formula (II) and (IV).
- the process comprises the following successive steps: i) reacting a diisocyanate of formula (XIV) with hydroxylated (meth)acrylates of formula (II) and (IV); and ii) adding to the resulting product of step i) a diol of formula (VI).
- the process may be carried out in the presence of a catalyst.
- the catalyst may be selected from compounds based on Sn, Ti, Zn, Zr, Ba, Bi, Co, Pb, Mn, preferably based on Sn, Bi, Zn, Ti, Zr.
- the catalyst may be selected from:
- - inorganic tin compounds such as stannous octoate, stannous oxalate, stannous stearate, stannous naphthenate or stannous chloride dihydrate;
- DBT dibutyltin
- DBT dibutyltin
- DOT dibutyltin
- DBT bis-O- phenylphenate DBT bis-(2,3-dihydroxypropylmercaptide), DBT bis-(2- hydroxyethylmercaptide), DBT bis-(4-hydroxyphenylmercaptide), dioctyltin bis-(2- hydroxyethylmercaptide), dioctyltin bis-(4-hydroxybutylmercaptide), DBT bis-(4- hydroxyphenylacetate), DBT bis-[3-(4-hydroxyphenyl)propionatel, DBT S,S-dibutylthio- carbonate, DBT diacetate, DBT diketanoate, DBT dilaurate, DBT dilauryl mercaptide or DBT malenate; dioctyltin (DOT) compounds, in particular DOT bis-(4-hydroxy
- bismuth compounds such as bismuth carboxylate, bismuth neodecanoate, bismuth stannate or bismuth stearate;
- - zinc compounds such as zinc acetate, zinc acetylacetoate, zinc neodecanoate, zinc octoate or zinc oxalate
- titanium compounds such as titanium acetylacetone complex, titanium ethylacetoacetonate complex, titanium tetrabutanolate or titanium triethanol
- zirconium - zirconium compounds such as zirconium ethyl acetoacetonate complex or zirconium octoate;
- organometallic compounds suitable as catalysts such as potassium octoate, potassium neodecanoate, amine complexes, copper oleate, copper naphthenate, cerium octoate, iron acetoacetonate, lead stannate, lead stearate, barium nitride.
- the curable composition of the invention comprises a urethane (meth)acrylate of formula (I).
- the curable composition of the invention may comprise a mixture of urethane (meth)acrylates of formula (I).
- the curable composition of the invention may further comprise an ethylenically unsaturated compound other than the urethane (meth)acrylate of formula (I).
- ethylenically unsaturated compound means a compound that comprises a polymerizable carbon-carbon double bond.
- a polymerizable carbon-carbon double bond is a carbon-carbon double bond that can react with another carbon-carbon double bond in a polymerization reaction.
- a polymerizable carbon-carbon double bond is generally comprised in a group selected from acrylate (including cyanoacrylate), methacrylate, acrylamide, methacrylamide, styrene, maleate, fumarate, itaconate, allyl, propenyl, vinyl and combinations thereof, preferably selected from acrylate, methacrylate and vinyl, more preferably selected from acrylate and methacrylate.
- the carbon-carbon double bonds of a phenyl ring are not considered as polymerizable carbon-carbon double bonds.
- the ethylenically unsaturated compound may be selected from a (meth)acrylate-functionalized monomer, a (meth)acrylate-functionalized oligomer, an amine- modified acrylate and mixtures thereof.
- the total amount of ethylenically unsaturated compound (including (meth)acrylate functionalized monomer, (meth)acrylate functionalized oligomer and amine-modified acrylate) in the curable composition may be from 0 to 80%, from 5 to 70%, from 10 to 60%, from 15 to 50% or from 20 to 40%, by weight based on the weight of the composition.
- the curable composition of the invention may comprise from 0 to 40%, from 5 to 40%, from 10 to 40%, from 15 to 40% or from 20 to 40%, by weight of ethylenically unsaturated compound based on the total weight of the curable composition.
- the curable composition of the invention may comprise from 40 to 80%, from 40 to 75%, from or 40 to 70%, from 40 to 65% or from 40 to 60%, by weight of ethylenically unsaturated compound based on the weight of the curable composition.
- (meth)acrylate-functionalized monomer means a monomer comprising a (meth)acrylate group, in particular an acrylate group.
- (meth)acrylate- functionalized oligomer means an oligomer comprising a (meth)acrylate group, in particular an acrylate group.
- the ethylenically unsaturated compound comprises a (meth)acrylate- functionalized monomer.
- the ethylenically unsaturated compound may comprise a mixture of (meth)acrylate-functionalized monomers.
- the (meth)acrylate-functionalized monomer may have a molecular weight of less than 600 g/mol, in particular from 100 to 550 g/mol, more particularly 200 to 500 g/mol.
- the (meth)acrylate-functionalized monomer may have 1 to 6 (meth)acrylate groups, in particular 1 to 3 (meth)acrylate groups.
- the (meth)acrylate-functionalized monomer may comprise a mixture of (meth)acrylate- functionalized monomers having different functionalities.
- the (meth)acrylate- functionalized monomer may comprise a mixture of a (meth)acrylate-functionalized monomer containing a single acrylate or methacrylate group per molecule (referred to herein as “mono(meth)acrylate-functionalized compounds”) and a (meth)acrylate-functionalized monomer containing 2 or more, preferably 2 or 3, acrylate and/or methacrylate groups per molecule.
- the (meth)acrylate functionalized monomer comprises a mono(meth)acrylate-functionalized monomer.
- the mono(meth)acrylate-functionalized monomer may advantageously function as a reactive diluent and reduce the viscosity of the composition of the invention.
- Suitable mono(meth)acrylate-functionalized monomers include, but are not limited to, mono-(meth)acrylate esters of aliphatic alcohols (wherein the aliphatic alcohol may be straight chain, branched or alicyclic and may be a mono-alcohol, a di-alcohol or a polyalcohol, provided only one hydroxyl group is esterified with (meth)acrylic acid); mono- (meth)acrylate esters of aromatic alcohols (such as phenols, including alkylated phenols); mono-(meth)acrylate esters of alkylaryl alcohols (such as benzyl alcohol); mono- (meth)acrylate esters of oligomeric and polymeric glycols such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol); mono-(meth)acrylate esters of monoalkyl ethers of glycols and oligoglycols;
- the following compounds are specific examples of mono(meth)acrylate-functionalized monomers suitable for use in the curable compositions of the present invention: methyl (meth)acrylate; ethyl (meth)acrylate; n-propyl (meth)acrylate; n-butyl (meth)acrylate; isobutyl (meth)acrylate; n-hexyl (meth)acrylate; 2-ethylhexyl (meth)acrylate; n-octyl (meth)acrylate; isooctyl (meth)acrylate; n-decyl (meth)acrylate; n-dodecyl (meth)acrylate; tridecyl (meth)acrylate; tetradecyl (meth)acrylate; hexadecyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate; 2- and 3-hydroxypropyl (meth)acrylate; 2-methoxye
- the (meth)acrylate functionalized monomer may comprise a (meth)acrylate-functionalized monomer containing two or more (meth)acrylate groups per molecule.
- suitable (meth)acrylate-functionalized monomers containing two or more (meth)acrylate groups per molecule include acrylate and methacrylate esters of polyhydric alcohols (organic compounds containing two or more, e.g., 2 to 6, hydroxyl groups per molecule).
- suitable polyhydric alcohols include C2-20 alkylene glycols (glycols having a C2-10 alkylene group may be preferred, in which the carbon chain may be branched; e.g., ethylene glycol, trimethylene glycol, 1 ,2-propylene glycol, 1 ,2-butanediol, 1 ,3- butanediol, 2,3-butanediol, tetramethylene glycol (1 ,4-butanediol), 1 ,5-pentanediol, 1 ,6- hexanediol, 1 ,8-octanediol, 1 ,9-nonanediol, 1 ,12-dodecanediol, cyclohexane-1 , 4-dimethanol, bisphenols, and hydrogenated bisphenols, as well as alkoxylated (e.g., ethoxylated and/or propyl
- Such polyhydric alcohols may be fully or partially esterified (with (meth)acrylic acid, (meth)acrylic anhydride, (meth)acryloyl chloride or the like), provided they contain at least two (meth)acrylate functional groups per molecule.
- Exemplary (meth)acrylate-functionalized monomers containing two or more (meth)acrylate groups per molecule may include ethoxylated bisphenol A di(meth)acrylates; triethylene glycol di(meth)acrylate; ethylene glycol di(meth)acrylate; tetraethylene glycol di(meth)acrylate; polyethylene glycol di(meth)acrylates; 1 ,4-butanediol diacrylate; 1 ,4- butanediol dimethacrylate; diethylene glycol diacrylate; diethylene glycol dimethacrylate, 1 ,6- hexanediol diacrylate; 1 ,6-hexanediol dimethacrylate; neopentyl glycol diacrylate; neopentyl glycol di(meth)acrylate; polyethylene glycol (600) dimethacrylate (where 600 refers to the approximate number average molecular weight of the polyethylene glycol portion); polyethylene glyco
- the curable composition of the invention may comprise from 0 to 80%, from 5 to 70%, from 10 to 60%, from 15 to 50% or from 20 to 40%, by weight of (meth)acrylate-functionalized monomer based on the total weight of the curable composition.
- the curable composition of the invention may comprise from 0 to 40%, from 5 to 40%, from 10 to 40%, from 15 to 40% or from 20 to 40%, by weight of (meth)acrylate-functionalized monomer based on the total weight of the curable composition.
- the curable composition of the invention may comprise from 40 to 80%, from 40 to 75%, from or 40 to 70%, from 40 to 65% or from 40 to 60%, by weight of (meth)acrylate-functionalized monomer based on the total weight of the curable composition.
- the ethylenically unsaturated compound comprises a (meth)acrylate- functionalized oligomer.
- the ethylenically unsaturated compound may comprise a mixture of (meth)acrylate-functionalized oligomers.
- the (meth)acrylate-functionalized oligomer may be selected in order to enhance the flexibility, strength and/or modulus, among other attributes, of a cured polymer prepared using the curable composition of the present invention.
- the (meth)acrylate functionalized oligomer may have 1 to 18 (meth)acrylate groups, in particular 2 to 6 (meth)acrylate groups, more particularly 2 to 6 acrylate groups.
- the (meth)acrylate functionalized oligomer may have a number average molecular weight equal or more than 600 g/mol, in particular 800 to 15,000 g/mol, more particularly 1 ,000 to 5,000 g/mol.
- the (meth)acrylate-functionalized oligomers may be selected from the group consisting of (meth)acrylate-functionalized urethane oligomers (sometimes also referred to as “urethane (meth)acrylate oligomers,” “polyurethane (meth)acrylate oligomers” or “carbamate (meth)acrylate oligomers”), (meth)acrylate-functionalized epoxy oligomers (sometimes also referred to as “epoxy (meth)acrylate oligomers”), (meth)acrylate-functionalized polyether oligomers (sometimes also referred to as “polyether (meth)acrylate oligomers”), (meth)acrylate-functionalized polydiene oligomers (sometimes also referred to as “polydiene (meth)acrylate oligomers”), (meth)acrylate-functionalized polycarbonate oligomers (sometimes also referred to as “polycarbonate (meth)acrylate oligomers”), and
- Exemplary polyester (meth)acrylate oligomers include the reaction products of acrylic or methacrylic acid or mixtures or synthetic equivalents thereof with hydroxyl group-terminated polyester polyols.
- the reaction process may be conducted such that all or essentially all of the hydroxyl groups of the polyester polyol have been (meth)acrylated, particularly in cases where the polyester polyol is difunctional.
- the polyester polyols can be made by polycondensation reactions of polyhydroxyl functional components (in particular, diols) and polycarboxylic acid functional compounds (in particular, dicarboxylic acids and anhydrides).
- the polyhydroxyl functional and polycarboxylic acid functional components can each have linear, branched, cycloaliphatic or aromatic structures and can be used individually or as mixtures.
- suitable epoxy (meth)acrylates include the reaction products of acrylic or methacrylic acid or mixtures thereof with an epoxy resin (polyglycidyl ether or ester).
- the epoxy resin may, in particular, by selected from bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, brominated bisphenol A diglycidyl ether, brominated bisphenol F diglycidyl ether, brominated bisphenol S diglycidyl ether, epoxy novolak resin, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol S diglycidyl ether, 3,4-epoxycyclohexylmethyl-3',4'- epoxycyclohexanecarboxylate, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-1 ,4- dioxane, bis(
- Suitable polyether (meth)acrylate oligomers include, but are not limited to, the condensation reaction products of acrylic or methacrylic acid or synthetic equivalents or mixtures thereof with polyetherols which are polyether polyols (such as polyethylene glycol, polypropylene glycol or polytetramethylene glycol).
- polyetherols can be linear or branched substances containing ether bonds and terminal hydroxyl groups.
- Polyetherols can be prepared by ring opening polymerization of cyclic ethers such as tetrahydrofuran or alkylene oxides (e.g., ethylene oxide and/or propylene oxide) with a starter molecule.
- Suitable starter molecules include water, polyhydroxyl functional materials, polyester polyols and amines.
- Polyurethane (meth)acrylate oligomers (sometimes also referred to as “urethane (meth)acrylate oligomers”) suitable for use in the curable compositions of the present invention include urethanes based on aliphatic, cycloaliphatic and/or aromatic polyester polyols and polyether polyols and aliphatic, cycloaliphatic and/or aromatic polyester diisocyanates and polyether diisocyanates capped with (meth)acrylate end-groups.
- Suitable polyurethane (meth)acrylate oligomers include, for example, aliphatic polyester-based urethane di- and tetra-acrylate oligomers, aliphatic polyether-based urethane di- and tetra- acrylate oligomers, as well as aliphatic polyester/polyether-based urethane di- and tetra- acrylate oligomers.
- the polyurethane (meth)acrylate oligomers may be prepared by reacting aliphatic, cycloaliphatic and/or aromatic polyisocyanates (e.g., diisocyanate, triisocyanate) with OH group terminated polyester polyols, polyether polyols, polycarbonate polyols, polycaprolactone polyols, polyorganosiloxane polyols (e.g., polydimethylsiloxane polyols), or polydiene polyols (e.g., polybutadiene polyols), or combinations thereof to form isocyanate- functionalized oligomers which are then reacted with hydroxyl-functionalized (meth)acrylates such as hydroxyethyl acrylate or hydroxyethyl methacrylate to provide terminal (meth)acrylate groups.
- aromatic polyisocyanates e.g., diisocyanate, triisocyanate
- polyester polyols e
- the polyurethane (meth)acrylate oligomers may contain two, three, four or more (meth)acrylate functional groups per molecule.
- Other orders of addition may also be practiced to prepare the polyurethane (meth)acrylate, as is known in the art.
- the hydroxyl-functionalized (meth)acrylate may be first reacted with a polyisocyanate to obtain an isocyanate-functionalized (meth)acrylate, which may then be reacted with an OH group terminated polyester polyol, polyether polyol, polycarbonate polyol, polycaprolactone polyol, polydimethylsiloxane polyol, polybutadiene polyol, or a combination thereof.
- a polyisocyanate may be first reacted with a polyol, including any of the aforementioned types of polyols, to obtain an isocyanate-functionalized polyol, which is thereafter reacted with a hydroxyl-functionalized (meth)acrylate to yield a polyurethane (meth)acrylate.
- a polyol including any of the aforementioned types of polyols
- an isocyanate-functionalized polyol which is thereafter reacted with a hydroxyl-functionalized (meth)acrylate to yield a polyurethane (meth)acrylate.
- all the components may be combined and reacted at the same time.
- Suitable acrylic (meth)acrylate oligomers include oligomers which may be described as substances having an oligomeric acrylic backbone which is functionalized with one or (meth)acrylate groups (which may be at a terminus of the oligomer or pendant to the acrylic backbone).
- the acrylic backbone may be a homopolymer, random copolymer or block copolymer comprised of repeating units of acrylic monomers.
- the acrylic monomers may be any monomeric (meth)acrylate such as C1- C6 alkyl (meth)acrylates as well as functionalized (meth)acrylates such as (meth)acrylates bearing hydroxyl, carboxylic acid and/or epoxy groups.
- Acrylic (meth)acrylate oligomers may be prepared using any procedures known in the art, such as by oligomerizing monomers, at least a portion of which are functionalized with hydroxyl, carboxylic acid and/or epoxy groups (e.g., hydroxyalkyl(meth)acrylates, (meth)acrylic acid, glycidyl (meth)acrylate) to obtain a functionalized oligomer intermediate, which is then reacted with one or more (meth)acrylate- containing reactants to introduce the desired (meth)acrylate functional groups.
- oligomerizing monomers at least a portion of which are functionalized with hydroxyl, carboxylic acid and/or epoxy groups (e.g., hydroxyalkyl(meth)acrylates, (meth)acrylic acid, glycidyl (meth)acrylate) to obtain a functionalized oligomer intermediate, which is then reacted with one or more (meth)acrylate- containing reactants to introduce the desired (meth
- the curable composition of the invention may comprise from 0 to 80%, from 5 to 70%, from 10 to 60%, from 15 to 50% or from 20 to 40%, by weight of (meth)acrylate-functionalized oligomer based on the total weight of the curable composition.
- the curable composition of the invention may comprise from 0 to 40%, from 5 to 40%, from 10 to 40%, from 15 to 40% or from 20 to 40%, by weight of (meth)acrylate-functionalized oligomer based on the total weight of the curable composition.
- the curable composition of the invention may comprise from 40 to 80%, from 40 to 75%, from or 40 to 70%, from 40 to 65% or from 40 to 60%, by weight of (meth)acrylate-functionalized oligomer based on the total weight of the curable composition.
- the ethylenically unsaturated compound comprises an amine-modified acrylate.
- the ethylenically unsaturated compound may comprise a mixture of amine-modified acrylates.
- An amine-modified acrylate is obtained by reacting an acrylate-functionalized compound with an amine-containing compound (aza-Michael addition).
- the amine-modified acrylate comprises at least one remaining acrylate group (i.e. an acrylate group that has not reacted with the amine-containing compound during the aza-Michael addition) and/or at least one (meth)acrylate group (which may not be reactive towards primary or secondary amines).
- the acrylate-functionalized compound may be an acrylate-functionalized monomer and/or acrylate-functionalized oligomer as defined above.
- the amine-containing compound comprises a primary or secondary amino group and optionally a tertiary amino group.
- the amine-containing compound may comprise more than one primary and/or secondary amino groups.
- the amine-containing compound may be selected from monoethanolamine (2-aminoethanol), 2-ethylhexylamine, octylamine, cyclohexylamine, sec-butylamine, isopropylamine, diethylamine, diethanolamine, dipropylamine, dibutylamine, 2-(methylamino)ethano-1 ,2-methoxyethylamine, bis(2- hydroxypropyl)amine, diisopropylamine, dipentylamine, dihexylamine, bis(2-ethylhexyl)amine, 1 ,2,3,4-tetrahydroisoquinoline, N-benzylmethylamine, morpholine, piperidine, dioctylamine, and di-cocoamine, dimethyl
- amine-modified acrylates examples include CN3705, CN3715, CN3755, CN381 and CN386, all available from Arkema. Polymeric or multi-amino versions are also suitable.
- the curable composition may comprise from 0% to 25%, in particular 2.5% to 20%, more particularly 5 to 15%, by weight of amine-modified acrylate based on the total weight of the curable composition.
- the curable composition may be radiation-curable, peroxide-curable, amine-curable or curable by a method combining the afore-mentioned methods of cure.
- the curable composition may be a radiation-curable composition.
- a radiation-curable composition may be at least partially cured by exposing the composition to radiation, such as heat, a light source (in particular visible, UV, near-UV or infrared light source) and/or electron beam.
- a light source in particular visible, UV, near-UV or infrared light source
- electron beam for cure with a light source, at least one photoinitiator is present while for electron-beam cure no photoinitiator is required.
- the photoinitiator may be a radical photoinitiator, in particular a radical photoinitiator having Norrish type I activity and/or Norrish type II activity, more particularly a radical photoinitiator having Norrish type II activity.
- Non-limiting types of radical photoinitiators suitable for use in the curable compositions of the present invention include, for example, benzoins, benzoin ethers, acetophenones, a-hydroxy acetophenones, benzyl, benzyl ketals, anthraquinones, phosphine oxides, acylphosphine oxides, a-hydroxyketones, phenylglyoxylates, a-aminoketones, benzophenones, thioxanthones, xanthones, acridine derivatives, phenazene derivatives, quinoxaline derivatives, triazine compounds, benzoyl formates, aromatic oximes, metallocenes, acylsilyl or acylgermanyl compounds, camphorquinones, polymeric derivatives thereof, and mixtures thereof.
- radical photoinitiators include, but are not limited to, 2- methylanthraquinone, 2-ethylanthraquinone, 2-chloroanthraquinone, 2-benzyanthraquinone, 2-t-butylanthraquinone, 1 ,2-benzo-9,10-anthraquinone, benzyl, benzoins, benzoin ethers, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, alpha- methylbenzoin, alpha-phenylbenzoin, Michler’s ketone, acetophenones such as 2,2- dialkoxybenzophenones and 1-hydroxyphenyl ketones, benzophenone, 4,4’-bis-(diethylamino) benzophenone, acetophenone, 2,2-diethyloxyacetophenone, diethyloxyacetophenone, 2- isopropyl
- the curable composition may be a peroxide-curable composition.
- a peroxide-curable composition may be at least partially cured by decomposition of a peroxide, in particular a hydroperoxide (R-O-O-H), a dialkyl peroxide (R-O-O-R) a peroxyacid (RC(O)-O-O-H), a peroxyester (RC(O)-O-O-R’), a diacyl peroxide (RC(0)-0-0-C(0)-R’), a peroxyketal and mixtures thereof, R and R’ being aliphatic, cycloaliphatic or aromatic groups.
- the peroxide may be decomposed by heating or using an activator at room temperature (20-25°C).
- the activator may be selected so as to promote the decomposition of the peroxide at room temperature such that curing is achieved without having to heat or bake the curable composition.
- the activator may be selected from an amine or a red/ox system, in particular a tertiary amine or red/ox system comprising a metallic salt or a potassium salt, more particularly a tertiary amine selected from N,N-dimethyl-p-toluidine (DMPT), N,N-dihydroxyethyl-p-toluidine (DHEPT), N,N-diethyl-p-toluidine (DEPT) and para-toluidine ethoxylate (PTE), or a red/ox system comprising a metallic salt selected from an iron salt, a copper salt, a cobalt salt, a manganese salt, a vanadium salt and mixtures thereof.
- DMPT N,N-dimethyl-p-toluidine
- DHEPT N,
- the curable composition may be an amine-curable composition.
- An amine-curable composition may be at least partially cured by Michael addition of an amine having free NH groups on a (meth)acrylate group of the urethane (meth)acrylate thus forming an aminoacrylate bond.
- the method combining the afore-mentioned methods of cure means any binary or ternary combination said afore-mentioned cure methods.
- said curable composition is a radiation-curable composition selected from the group consisting of UV-curable, electron beam-curable.
- said curable composition is a coating composition selected from a paint, varnish, ink, including inkjet ink and screen ink, adhesive, sealant or resist, composition or said curable composition is a composite material composition or a 3D-printing composition.
- the present invention also relates to a cured product, which results from the cure of at least one urethane (meth)acrylate according to the present invention or from the cure of at least one curable composition according to the present invention.
- the cured product is a coating selected from a paint, a varnish, an ink, including inkjet ink and screen ink, an adhesive, a sealant or a resist or it is a composite material or a 3D printed article.
- Another subject-matter of the present invention relates to the use of the urethane (meth)acrylate of the invention in a coating composition selected from a paint, a varnish, an ink, an adhesive, a sealant or a resist compositions, in a composite material composition or in a 3D article printing compositions. More particularly, the urethane (meth)acrylate of the invention may be used to obtain compositions having a lower viscosity compared to that of a composition comprising a urethane (meth)acrylate that is not according to the present invention in equivalent amounts.
- the viscosity was measured at 60 °C using Brookfield viscometer RVDVII+ at 100 rpm with spindle 27 or at 6 rpm with spindle18.
- %wt of urethane bonds (%U) is based on the number average molecular weight of the urethane (meth)acrylate and was calculated with the following equation: a x 59
- Mn is the number average molecular weight of the urethane (meth)acrylate obtained by calculation using the number average molecular weight of the components used to form the urethane (meth)acrylate.
- MP A is the number average molecular weight of the hydroxylated (meth)acrylate of formula (II);
- MP A ’ is the number average molecular weight of the hydroxylated (meth)acrylate of formula (IV);
- MPB is the number average molecular weight of the diisocyanate of formula (XIV);
- Mn D is the number average molecular weight of the diol of formula (VI). Number average molecular weight
- the number average molecular weight of the components used to form the urethane (meth)acrylate i.e. the hydroxylated (meth)acrylates of formula (II) and (IV), the diol of formula (VI) and the diisocyanate of formula (XIV)
- the number average molecular weight of the urethane (meth)acrylate may be measured by gel permeation chromatography (GPC) using polystyrene standards. The measurement conditions of GPC are given below:
- IPDI isophorone diisocyanate
- BHT 0.2 gram of (BHT)
- DBTDL dibutyltin dilaurate
- Example 1 was reproduced using 43.8 grams of SR495 instead of HEA (SR495 replacing HEA in same molar amount).
- Example 3 (invention) Example 1 was reproduced using 115.4 grams of AP-800 instead of HEA (AP-800 replacing HEA in same molar amount).
- IPDI isophorone diisocyanate
- BHT 0.2 gram of (BHT)
- DBTDL dibutyltin dilaurate
- Example 7 was reproduced using 43.8 gram of SR495 instead of HEA (SR495 replacing HEA in same molar amount).
- Example 5 was reproduced using 115.4 grams of AP-800 instead of HEA (AP-800 replacing HEA in same molar amount).
- IPDI isophorone diisocyanate
- BHT 0.2 gram of (BHT)
- DBTDL dibutyltin dilaurate
- Example 7 was reproduced using 43.8 grams of SR495 instead of HEA (SR495 replacing HEA in same molar amount).
- Example 9 (comparative)
- Example 7 was reproduced using 115.4 grams of AP-800 instead of HEA (AP-800 replacing HEA in same molar amount).
- Example 10 Applicative properties The characteristics of the urethane (meth)acrylates of Examples 1 -9 are presented in the table below.
- the urethane (meth)acrylates of the invention have a significantly reduced viscosity compared to that of the comparative examples.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
La présente invention concerne un (méth)acrylate d'uréthane obtenu en utilisant une combinaison spécifique de (méth)acrylates hydroxylés, d'un diisocyanate et d'un diol, ainsi que son procédé de fabrication. La présente invention concerne également une composition durcissable comprenant le (méth)acrylate d'uréthane et un produit durci obtenu par durcissement du (méth)acrylate d'uréthane ou de la composition durcissable.
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Citations (8)
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EP0243802B1 (fr) * | 1986-04-24 | 1991-07-17 | Nippon Kayaku Kabushiki Kaisha | (Méth)acrylates de silicone-uréthane ainsi que compositions de résine et matériau de revêtement qui les renferme |
WO1991018033A1 (fr) | 1990-05-22 | 1991-11-28 | Dsm N.V. | Composition devant s'utiliser lors du moulage par injection de resine et contenant des composes a faible poids moleculaire formant conjointement un reseau hybride |
JP2004035599A (ja) * | 2002-06-28 | 2004-02-05 | Natoko Kk | ウレタン(メタ)アクリレート及びそれを含有する活性エネルギー線硬化性組成物並びにそれらの用途 |
EP1767553A1 (fr) * | 2005-09-26 | 2007-03-28 | Dejima Tech bv | Polymères d'urethane-(meth)acrylate réticulable par UV |
JP4013532B2 (ja) | 2001-11-26 | 2007-11-28 | 東亞合成株式会社 | 光学部材用活性エネルギー線硬化型組成物 |
US20100168320A1 (en) * | 2007-06-21 | 2010-07-01 | Basf Se | Flexible, radiation-curable coating compositions |
US20200277444A1 (en) * | 2017-11-27 | 2020-09-03 | Henkel IP & Holding GmbH | Polysiloxane Urethane Compounds and Optically Transparent Adhesive Compositions |
US10851195B2 (en) * | 2015-07-31 | 2020-12-01 | Arkema France | Polyurethane (meth)acrylate oligomers and curable compositions comprising said oligomers |
-
2021
- 2021-03-01 WO PCT/IB2021/000126 patent/WO2022185086A1/fr active Application Filing
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0243802B1 (fr) * | 1986-04-24 | 1991-07-17 | Nippon Kayaku Kabushiki Kaisha | (Méth)acrylates de silicone-uréthane ainsi que compositions de résine et matériau de revêtement qui les renferme |
WO1991018033A1 (fr) | 1990-05-22 | 1991-11-28 | Dsm N.V. | Composition devant s'utiliser lors du moulage par injection de resine et contenant des composes a faible poids moleculaire formant conjointement un reseau hybride |
JP4013532B2 (ja) | 2001-11-26 | 2007-11-28 | 東亞合成株式会社 | 光学部材用活性エネルギー線硬化型組成物 |
JP2004035599A (ja) * | 2002-06-28 | 2004-02-05 | Natoko Kk | ウレタン(メタ)アクリレート及びそれを含有する活性エネルギー線硬化性組成物並びにそれらの用途 |
EP1767553A1 (fr) * | 2005-09-26 | 2007-03-28 | Dejima Tech bv | Polymères d'urethane-(meth)acrylate réticulable par UV |
US20100168320A1 (en) * | 2007-06-21 | 2010-07-01 | Basf Se | Flexible, radiation-curable coating compositions |
US10851195B2 (en) * | 2015-07-31 | 2020-12-01 | Arkema France | Polyurethane (meth)acrylate oligomers and curable compositions comprising said oligomers |
US20200277444A1 (en) * | 2017-11-27 | 2020-09-03 | Henkel IP & Holding GmbH | Polysiloxane Urethane Compounds and Optically Transparent Adhesive Compositions |
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