CA2776089C - High reactivity curable paste ink compositions - Google Patents
High reactivity curable paste ink compositions Download PDFInfo
- Publication number
- CA2776089C CA2776089C CA2776089A CA2776089A CA2776089C CA 2776089 C CA2776089 C CA 2776089C CA 2776089 A CA2776089 A CA 2776089A CA 2776089 A CA2776089 A CA 2776089A CA 2776089 C CA2776089 C CA 2776089C
- Authority
- CA
- Canada
- Prior art keywords
- curable
- ink composition
- monomer
- temperature
- paste ink
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 200
- 230000009257 reactivity Effects 0.000 title description 3
- 239000007788 liquid Substances 0.000 claims abstract description 73
- 230000005855 radiation Effects 0.000 claims abstract description 54
- 239000003349 gelling agent Substances 0.000 claims abstract description 42
- 239000003086 colorant Substances 0.000 claims abstract description 24
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 11
- 239000012949 free radical photoinitiator Substances 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 89
- 239000000758 substrate Substances 0.000 claims description 64
- 239000007787 solid Substances 0.000 claims description 60
- 238000012546 transfer Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 18
- 238000002844 melting Methods 0.000 claims description 18
- 230000008018 melting Effects 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 238000007641 inkjet printing Methods 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000000746 allylic group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 239000000976 ink Substances 0.000 description 185
- 239000001993 wax Substances 0.000 description 61
- 125000000217 alkyl group Chemical group 0.000 description 53
- 125000005842 heteroatom Chemical group 0.000 description 39
- 125000004122 cyclic group Chemical group 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 30
- 125000002015 acyclic group Chemical group 0.000 description 28
- 238000001723 curing Methods 0.000 description 27
- 229920006395 saturated elastomer Polymers 0.000 description 25
- 125000002947 alkylene group Chemical group 0.000 description 21
- 239000000126 substance Substances 0.000 description 21
- -1 polyethylene Polymers 0.000 description 19
- 125000000732 arylene group Chemical group 0.000 description 18
- 125000002877 alkyl aryl group Chemical group 0.000 description 16
- 125000003710 aryl alkyl group Chemical group 0.000 description 16
- 230000008859 change Effects 0.000 description 15
- 239000002253 acid Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 238000007639 printing Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000123 paper Substances 0.000 description 8
- 238000003892 spreading Methods 0.000 description 8
- 230000007480 spreading Effects 0.000 description 8
- JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 6
- 239000000539 dimer Substances 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- ICAIHSUWWZJGHD-UHFFFAOYSA-N dotriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O ICAIHSUWWZJGHD-UHFFFAOYSA-N 0.000 description 4
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 4
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 4
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- UTGPYHWDXYRYGT-UHFFFAOYSA-N tetratriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTGPYHWDXYRYGT-UHFFFAOYSA-N 0.000 description 4
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 description 4
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- HQRWEDFDJHDPJC-UHFFFAOYSA-N Psyllic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HQRWEDFDJHDPJC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000019241 carbon black Nutrition 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 2
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- HVUCKZJUWZBJDP-UHFFFAOYSA-N Ceroplastic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HVUCKZJUWZBJDP-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 235000021353 Lignoceric acid Nutrition 0.000 description 2
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 241000274582 Pycnanthus angolensis Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008365 aromatic ketones Chemical class 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000011111 cardboard Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- VXZBFBRLRNDJCS-UHFFFAOYSA-N heptacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VXZBFBRLRNDJCS-UHFFFAOYSA-N 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 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 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000011087 paperboard Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000992 solvent dye Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 description 1
- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 description 1
- VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical class C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- PFJZOBRGDTYDQC-UHFFFAOYSA-N 1,4-diisocyanato-4-methylpentane Chemical compound O=C=NC(C)(C)CCCN=C=O PFJZOBRGDTYDQC-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- DWIHAOZQQZSSBB-UHFFFAOYSA-N 1-isocyanato-1-(2-isocyanatopropyl)cyclohexane Chemical compound O=C=NC(C)CC1(N=C=O)CCCCC1 DWIHAOZQQZSSBB-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- IDOQDZANRZQBTP-UHFFFAOYSA-N 2-[2-(2,4,4-trimethylpentan-2-yl)phenoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1OCCO IDOQDZANRZQBTP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/17—Ink jet characterised by ink handling
- B41J2/175—Ink supply systems ; Circuit parts therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/17—Ink jet characterised by ink handling
- B41J2/175—Ink supply systems ; Circuit parts therefor
- B41J2/17593—Supplying ink in a solid state
-
- 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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/105,090 US8690305B2 (en) | 2011-05-11 | 2011-05-11 | High reactivity curable paste ink compositions |
| US13/105,090 | 2011-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2776089A1 CA2776089A1 (en) | 2012-11-11 |
| CA2776089C true CA2776089C (en) | 2016-06-28 |
Family
ID=47070701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2776089A Expired - Fee Related CA2776089C (en) | 2011-05-11 | 2012-05-07 | High reactivity curable paste ink compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8690305B2 (OSRAM) |
| JP (1) | JP5866254B2 (OSRAM) |
| KR (1) | KR101793292B1 (OSRAM) |
| CN (1) | CN102775850B (OSRAM) |
| CA (1) | CA2776089C (OSRAM) |
| DE (1) | DE102012207394B4 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140071213A1 (en) * | 2012-09-13 | 2014-03-13 | Xerox Corporation | Phase Change Ink Compositions For Image Robustness |
| CN105026479B (zh) * | 2013-02-26 | 2017-10-27 | 富士胶片株式会社 | 纤维素酰化物膜、新化合物、偏振片及液晶显示装置 |
| JP6519470B2 (ja) | 2013-07-02 | 2019-05-29 | コニカミノルタ株式会社 | インクジェットプリンタおよび画像形成方法 |
| WO2015033584A1 (ja) | 2013-09-09 | 2015-03-12 | コニカミノルタ株式会社 | 活性光線硬化型インクジェットインクおよび画像形成方法 |
| CN105384951B (zh) | 2014-09-03 | 2020-09-18 | 富士胶片株式会社 | 聚合物膜、偏振片及液晶显示装置 |
| WO2016130352A1 (en) | 2015-02-13 | 2016-08-18 | 3M Innovative Properties Company | Fluorine-free fibrous treating compositions including a polycarbodiimide and an optional paraffin wax, and treating methods |
| CN107223144B (zh) | 2015-02-13 | 2021-02-02 | 3M创新有限公司 | 包含含有异氰酸酯衍生的烯键式不饱和单体的低聚物的无氟纤维处理组合物以及处理方法 |
| US9676952B2 (en) * | 2015-02-24 | 2017-06-13 | Xerox Corporation | 3D printing system comprising solid build ink comprising colorant |
| EP3225309B1 (fr) | 2016-03-31 | 2018-08-22 | Biomérieux | Procédé de fabrication de membranes d'analyse de dispositifs microfluidiques |
| CN107858044B (zh) * | 2017-10-09 | 2020-11-13 | 广东高仕电研科技有限公司 | 一种uv固化喷印油墨及其制备方法 |
| WO2019123123A1 (en) * | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Low dielectric constant curable ink compositions |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048925A (en) * | 1996-06-28 | 2000-04-11 | Xerox Corporation | Urethane isocyanate-derived resins for use in a phase change ink formulation |
| EP0816447B1 (en) | 1996-06-28 | 2003-09-10 | Xerox Corporation | Phase change ink formulation using a urethane isocyanate-derived resin and a urethane isocyanate-derived wax |
| GB2336594A (en) * | 1998-04-21 | 1999-10-27 | Coates Brothers Plc | Radiation-curable Ink Compositions |
| EP1024157A1 (en) | 1999-01-29 | 2000-08-02 | Tektronix, Inc. | Urethane isocyanate-derived resins for use in a phase change ink formulation |
| ES2308008T3 (es) | 2002-11-15 | 2008-12-01 | Markem Corporation | Tintas curables por radiacion. |
| JP2007527459A (ja) | 2004-03-03 | 2007-09-27 | マーケム コーポレーション | 噴射可能インク |
| US7279587B2 (en) | 2005-11-30 | 2007-10-09 | Xerox Corporation | Photoinitiator with phase change properties and gellant affinity |
| US7559639B2 (en) | 2005-11-30 | 2009-07-14 | Xerox Corporation | Radiation curable ink containing a curable wax |
| US7276614B2 (en) | 2005-11-30 | 2007-10-02 | Xerox Corporation | Curable amide gellant compounds |
| US7625956B2 (en) | 2005-11-30 | 2009-12-01 | Xerox Corporation | Phase change inks containing photoinitiator with phase change properties and gellant affinity |
| US7820731B2 (en) * | 2005-12-15 | 2010-10-26 | Xerox Corporation | Radiation curable inks |
| US8142557B2 (en) * | 2006-06-28 | 2012-03-27 | Xerox Corporation | Radiation curable ink containing gellant and radiation curable wax |
| US7531582B2 (en) | 2006-08-23 | 2009-05-12 | Xerox Corporation | Radiation curable phase change inks containing curable epoxy-polyamide composite gellants |
| US7699918B2 (en) | 2007-05-31 | 2010-04-20 | Xerox Corporation | Reactive ink components and methods for forming images using reactive inks |
| US20100055407A1 (en) | 2008-09-04 | 2010-03-04 | Xerox Corporation | Ultra-Violet Curable Gellant Inks For Creating Tactile Text And Images For Packaging Applications |
| US8916084B2 (en) * | 2008-09-04 | 2014-12-23 | Xerox Corporation | Ultra-violet curable gellant inks for three-dimensional printing and digital fabrication applications |
| US8123347B2 (en) | 2009-02-27 | 2012-02-28 | Xerox Corporation | Method of forming images using curable ink with gellant |
| US20100242790A1 (en) | 2009-03-24 | 2010-09-30 | Xerox Corporation | Cationically and hybrid curable uv gels |
| US8334026B2 (en) | 2009-05-29 | 2012-12-18 | Xerox Corporation | Tunable fluorescent UV curable gel inks containing fluorescent monomers for food packaging applications |
| US8262210B2 (en) | 2009-09-29 | 2012-09-11 | Xerox Corporation | Curable gel inks with reduced syneresis and halo formation |
| US8853293B2 (en) * | 2009-12-18 | 2014-10-07 | Xerox Corporation | Curable solid ink compositions |
| US20110152396A1 (en) * | 2009-12-18 | 2011-06-23 | Xerox Corporation | Curable Solid Overcoat Compositions |
| US8158693B2 (en) | 2010-02-11 | 2012-04-17 | Xerox Corporation | Process for preparing stable pigmented curable solid inks |
| US8236870B2 (en) * | 2010-02-11 | 2012-08-07 | Xerox Corporation | Curable solid ink compositions |
| US8084637B2 (en) | 2010-04-22 | 2011-12-27 | Xerox Corporation | Amide gellant compounds with aromatic end groups |
| US8097661B2 (en) | 2010-04-22 | 2012-01-17 | Xerox Corporation | Ink compositions and methods |
| US8449095B2 (en) * | 2010-07-13 | 2013-05-28 | Xerox Corporation | Radiation curable solid ink compositions suitable for transfuse printing applications |
| US8459788B2 (en) * | 2011-03-04 | 2013-06-11 | Xerox Corporation | Curable solid ink compositions comprising novel curable wax |
-
2011
- 2011-05-11 US US13/105,090 patent/US8690305B2/en not_active Expired - Fee Related
-
2012
- 2012-05-04 DE DE102012207394.9A patent/DE102012207394B4/de not_active Expired - Fee Related
- 2012-05-07 CA CA2776089A patent/CA2776089C/en not_active Expired - Fee Related
- 2012-05-09 KR KR1020120049305A patent/KR101793292B1/ko not_active Expired - Fee Related
- 2012-05-10 JP JP2012108708A patent/JP5866254B2/ja not_active Expired - Fee Related
- 2012-05-11 CN CN201210147507.0A patent/CN102775850B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101793292B1 (ko) | 2017-11-02 |
| DE102012207394B4 (de) | 2018-06-21 |
| US20120287199A1 (en) | 2012-11-15 |
| KR20120128556A (ko) | 2012-11-27 |
| CA2776089A1 (en) | 2012-11-11 |
| JP2012236998A (ja) | 2012-12-06 |
| CN102775850B (zh) | 2016-05-11 |
| JP5866254B2 (ja) | 2016-02-17 |
| DE102012207394A1 (de) | 2012-11-15 |
| CN102775850A (zh) | 2012-11-14 |
| US8690305B2 (en) | 2014-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20210507 |