JPH01253732A - Photopolymerizable composition and recording medium using same - Google Patents
Photopolymerizable composition and recording medium using sameInfo
- Publication number
- JPH01253732A JPH01253732A JP8194388A JP8194388A JPH01253732A JP H01253732 A JPH01253732 A JP H01253732A JP 8194388 A JP8194388 A JP 8194388A JP 8194388 A JP8194388 A JP 8194388A JP H01253732 A JPH01253732 A JP H01253732A
- Authority
- JP
- Japan
- Prior art keywords
- recording medium
- photopolymerizable composition
- transfer recording
- photopolymerization initiator
- recording layer
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 238000012546 transfer Methods 0.000 claims abstract description 45
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 239000003086 colorant Substances 0.000 claims abstract description 14
- 238000012644 addition polymerization Methods 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 9
- 230000000704 physical effect Effects 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 abstract description 16
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 239000011230 binding agent Substances 0.000 abstract description 7
- 239000000853 adhesive Substances 0.000 abstract description 6
- 230000001070 adhesive effect Effects 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 239000003505 polymerization initiator Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 41
- 238000000034 method Methods 0.000 description 14
- -1 Aliphatic amines Chemical class 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 5
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- 239000002245 particle Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
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- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
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- 239000004698 Polyethylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000007193 benzoin condensation reaction Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000001454 recorded image Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- JODFDXUBCBQKNC-UHFFFAOYSA-N 4-bromobenzenecarboximidamide Chemical compound NC(=N)C1=CC=C(Br)C=C1 JODFDXUBCBQKNC-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
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- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
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- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 description 1
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical class CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- UJMVOHLBEMHSSK-UHFFFAOYSA-N phenyl 4-(diethylamino)benzoate Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)OC1=CC=CC=C1 UJMVOHLBEMHSSK-UHFFFAOYSA-N 0.000 description 1
- SLRGLNRNKBEWIA-UHFFFAOYSA-N phenyl 4-(dimethylamino)benzoate Chemical compound C1=CC(N(C)C)=CC=C1C(=O)OC1=CC=CC=C1 SLRGLNRNKBEWIA-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は感光性平版印刷版、ＵＶ塗料、接着材などや、
光重合を利用した画像形成方法に好適な光重合性組成物
及び記録媒体に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention is applicable to photosensitive planographic printing plates, UV paints, adhesives, etc.
The present invention relates to a photopolymerizable composition and a recording medium suitable for an image forming method using photopolymerization.
光重合組成物は従来より様々な分野で利用されている。 Photopolymerizable compositions have been used in various fields.
例えば、光重合性組成物はＵＶ塗料、光硬化型接着剤、
感光性平版印刷版などに利用されている。また、光重合
性組成物を利用した画像形成方法としては、米国特許４
，３９９，２０９号や米国特許４，４１６，９６６号が
ある。米国特許４，３９９，２０９号の画像形成方法は
、光重合性組成物と発色剤とを含有したマイクロカプセ
ルを基材上に配列した記録媒体を用い、記録画像に応じ
て変換された主に紫外光によりマイクロカプセル内の光
重合性組成物を硬化させて転写像を形成し、更にこの転
写像を顕色層を有する被記録体に重ねて、一対の圧力ロ
ーラ間のニップに通過させてマイクロカプセルを破壊し
、かつ画像を顕色する転写画像形成システムを開示して
いる。画像は、発色剤を画像形成シートに造像的に転写
し、そこで発色剤が反応して画像を形成することによっ
て多色画像を得る。For example, photopolymerizable compositions include UV paints, photocurable adhesives,
It is used in photosensitive planographic printing plates, etc. Furthermore, as an image forming method using a photopolymerizable composition, US Pat.
, 399,209 and US Pat. No. 4,416,966. The image forming method disclosed in U.S. Pat. The photopolymerizable composition in the microcapsules is cured with ultraviolet light to form a transferred image, and this transferred image is further superimposed on a recording medium having a color developing layer and passed through a nip between a pair of pressure rollers. A transfer image forming system is disclosed that destroys microcapsules and develops an image. A multicolor image is obtained by imagewise transferring a color former to an image forming sheet, where the color former reacts to form an image.
また、米国特許４，４１６，９６６号は、顕色剤が感光
マイクロカプセルと同一の支持体表面上に存在するセル
フコンテインド（５ｅｌｆ−ｃｏｎｔａｉｎｅｄ ）画
像形成システムを開示している。記録画像に応じて変換
された主に紫外光により、露光した後、画像形成シート
を圧力ロールに通過させるときに、マイクロカプセルは
破壊し、内相を造像的に放出する。その際、発色剤は、
通常別個の層内に設けられる顕色剤に移行し、そこで発
色剤は反応しかつ色画像を形成する。Also, US Pat. No. 4,416,966 discloses a self-contained imaging system in which the color developer is on the same support surface as the photosensitive microcapsules. After exposure, primarily by ultraviolet light converted in accordance with the recorded image, the microcapsules rupture and release the internal phase imagewise when the imaging sheet is passed through a pressure roll. At that time, the coloring agent is
The color former is transferred to a developer, usually provided in a separate layer, where it reacts and forms a color image.
上記２方式のような記録方式はいずれもマイクロカプセ
ル内に光重合性組成物を含有し、光重合性組成物の感光
波長域を異ならせしめ、それぞれの感光波長域に対応す
るように変換された主に紫外光により、マイクロカプセ
ル内の内容物を硬化させるものである。Both of the above two recording methods contain a photopolymerizable composition in a microcapsule, and the photopolymerizable composition has different photosensitive wavelength ranges, and the photopolymerizable composition is converted to correspond to each photosensitive wavelength range. The contents inside the microcapsules are cured mainly by ultraviolet light.
しかしながら、従来の光重合性組成物の感度は未だ十分
とは言えず、まだまだ感度を上げる必要があった。However, the sensitivity of conventional photopolymerizable compositions is still not sufficient, and there is still a need to increase the sensitivity.
本発明は、上記従来技術に鑑みてなされたもので、感度
の優れた光重合性組成物及び記録媒体を提供することを
目的とする。The present invention was made in view of the above-mentioned prior art, and an object of the present invention is to provide a photopolymerizable composition and a recording medium with excellent sensitivity.
本発明の光重合性組成物は、付加重合可能なエチレン性
不飽和二重結合を有する化合物および下記一般式（１）
で示される光重合開始剤を含有するものである。The photopolymerizable composition of the present invention comprises a compound having an ethylenically unsaturated double bond capable of addition polymerization and the following general formula (1).
It contains a photopolymerization initiator shown in the following.
（式中、又は−Ｓ−、−５Ｏ−あるいは−５Ｏ２−０Ｒ
＋は水素原子、炭素数１〜６のアルキル基、アルコキシ
基あるいはハロゲン原子。(In the formula, or -S-, -5O- or -5O2-0R
+ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group, or a halogen atom.
Ａ ｒ ｌ、 Ａ ｒ２は置換基を有してもよい芳香
環あるいは複素環。）
一般式（Ｉ）で表わされる化合物は、その分子構造中に
Ｓ原子を含み、その重原子効果により重合を開始するラ
ジカルを生ずる励起三重項状態への系間交差が効率よく
起るため、高い感度を示すと考えられる。A r l and A r2 are aromatic rings or hetero rings which may have substituents. ) The compound represented by general formula (I) contains an S atom in its molecular structure, and due to its heavy atom effect, intersystem crossing to an excited triplet state that generates a radical that initiates polymerization occurs efficiently; It is thought to exhibit high sensitivity.
式中Ａｒ＋、Ａｒｚは置換基を有してもよい芳香環。In the formula, Ar+ and Arz are aromatic rings which may have a substituent.
複素環を表わし、Ａｒｃ、 Ａｒｚは同じであっても
異なっていてもよい。It represents a heterocycle, and Arc and Arz may be the same or different.
芳香環としてはベンゼン環、ナフタレン環、インデン環
、ナフタレン環などがあげられる。Examples of the aromatic ring include a benzene ring, a naphthalene ring, an indene ring, and a naphthalene ring.
複素環としてはピリジン環、フラン環、チオフェン環、
ピロール環、イミダゾール環、オキサゾール環などがあ
げられる。Examples of heterocycles include pyridine ring, furan ring, thiophene ring,
Examples include a pyrrole ring, an imidazole ring, and an oxazole ring.
上記Ａｒ＋、Ａｒ２のどちらかまたは両方が芳香環であ
ることが好ましく、ベンゼン環であることが特に好まし
い。Either or both of Ar+ and Ar2 are preferably aromatic rings, particularly preferably benzene rings.
Ａｒｃ、Ａｒｚが有する置換基としては水素原子、ハロ
ゲン原子、炭素数１〜６のアルキル基、アルコキシ基、
フェノキシ基、アミノ基、アルキルアミノ基。Substituents of Arc and Arz include hydrogen atom, halogen atom, alkyl group having 1 to 6 carbon atoms, alkoxy group,
Phenoxy group, amino group, alkylamino group.
ジアルキルアミノ基、水酸基、アセトキシ基、ベンゾイ
ロキシ基、アセチル基、トリフルオロメチル基、カルボ
キシル基、シアノ基などがあげられる。Examples include dialkylamino group, hydroxyl group, acetoxy group, benzyloxy group, acetyl group, trifluoromethyl group, carboxyl group, and cyano group.
Ａｒｃ、 Ａｒ２のどちらかに上記置換基のうち電子
供与性基を少な（とも１つ含むことが好ましく、前記置
換基がアルコキシ基、アセトキシ基またはベンゾイロキ
シ基であることが特に好ましい。It is preferable that either Arc or Ar2 contains at least one electron-donating group among the above substituents, and it is particularly preferable that the substituent is an alkoxy group, an acetoxy group, or a benzyloxy group.
一般式（Ｉ）の具体例としては以下のものがあげられる
が、本発明はこれに限定されるものではない。Specific examples of general formula (I) include the following, but the present invention is not limited thereto.
上記物質は主としてベンゾイン縮合を利用して合成され
る。The above substances are mainly synthesized using benzoin condensation.
１ ２ ０ｒ
アルデヒドよ、？を通常のベンゾイン縮合によりベンゾ
イン誘導体旦とする。次に硫酸銅を用いて旦を酸化、ベ
ンジル誘導体４とする。1 2 0r Aldehyde, huh? A benzoin derivative is obtained by conventional benzoin condensation. Next, the benzyl derivative 4 is oxidized using copper sulfate.
さらにスルホキシド誘導体旦、スルホン誘導体９はそれ
ぞれベンジル誘導体企を二酸化マンガン、過マンガン酸
カリウムを用いて酸化することで得られる。Furthermore, sulfoxide derivatives and sulfone derivatives 9 can be obtained by oxidizing benzyl derivatives using manganese dioxide and potassium permanganate, respectively.
一般式（１）で表わされる光重合開始剤は、後述の付加
重合可能なエチレン性不飽和二重結合を有する化合物に
対し重量比（以下同様）で約１：５〜１ ： １０００
の範囲で用いることが好ましく、更には約１＝ｌＯ〜１
： １００の範囲が好ましい。The photopolymerization initiator represented by general formula (1) has a weight ratio (the same applies hereinafter) of about 1:5 to 1:1000 to the below-described compound having an ethylenically unsaturated double bond capable of addition polymerization.
It is preferable to use the range of 1=lO to 1
: A range of 100 is preferable.
本発明の光重合性組成物は、アミン類と併用することで
感度が更に向上する場合がある。併用するアミンとして
、芳香族アミンとしては、エチル−ｐ−ジメチルアミノ
ベンゾエート、メチル−ｐ −ジメチルアミノベンゾエ
ート、イソアミル−ｐ−ジメチルアミノベンゾエート、
フェニル−ｐ−ジメチルアミノベンゾエート、エチル−
ｐ−ジエチルアミノベンゾエート、フェニル−ｐ−ジエ
チルアミノベンゾエート、 Ｎ、Ｎ−ジメチルアニリ
ン、Ｎ、Ｎ−ジエチルアニリン、 Ｎ、Ｎ−ジメチル
ベンジルアミノン、Ｎ−ベンジルーＮ−メチルアニリン
、Ｎ、Ｎ−ジベンジルアニリン、トリフェニルアミンな
どがある。The sensitivity of the photopolymerizable composition of the present invention may be further improved by using it in combination with amines. Aromatic amines used in combination include ethyl-p-dimethylaminobenzoate, methyl-p-dimethylaminobenzoate, isoamyl-p-dimethylaminobenzoate,
Phenyl-p-dimethylaminobenzoate, ethyl-
p-diethylaminobenzoate, phenyl-p-diethylaminobenzoate, N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethylbenzylaminone, N-benzyl-N-methylaniline, N,N-dibenzylaniline, These include triphenylamine.
脂肪族アミンとしてはトリメチルアミン、トリエチルア
ミン、トリプロピルアミン、ジメチルシクロヘキシルア
ミン、トリエタノールアミンなどがある。Aliphatic amines include trimethylamine, triethylamine, tripropylamine, dimethylcyclohexylamine, and triethanolamine.
ポリアミンとしてはメチレンジアミン、へ゛キサメチレ
ンジアミン、ｌ、４−シクロヘキサンジアミン、フェニ
レンジアミンなどがあげられる。Examples of the polyamine include methylene diamine, hexamethylene diamine, 1,4-cyclohexane diamine, and phenylene diamine.
上述のアミン類は１種類でも、２種以上混合して用いて
もよい。The above-mentioned amines may be used alone or in combination of two or more.
アミン類は一般式（１）の化合物に対し約１：１゜〜１
０：１の範囲で用いることが好ましく、更には約１：５
〜５：ｌの範囲が好ましい。The ratio of amines to the compound of general formula (1) is approximately 1:1° to 1
It is preferable to use it in the range of 0:1, more preferably about 1:5.
A range of 5:l is preferred.
付加重合可能なエチレン性不飽和二重結合を有する化合
物とは、その化学構造中に少なくとも１つのエチレン性
不飽和二重結合を有する化合物でモノマー、オリゴマー
、ポリマーなどの化学形態をもつものである。A compound having an ethylenically unsaturated double bond capable of addition polymerization is a compound having at least one ethylenically unsaturated double bond in its chemical structure, and has a chemical form such as a monomer, oligomer, or polymer. .
付加重合可能なエチレン性不飽和二重結合を有する化合
物で、モノマー、オリゴマーの例としては、メチルアク
リレート、メチルメタクリレート。A compound having an ethylenically unsaturated double bond that can undergo addition polymerization. Examples of monomers and oligomers include methyl acrylate and methyl methacrylate.
アクリロニトリル、アクリルアミドなどの単量体や、ア
クリル酸、メタクリル酸、イタコン酸、クロトン酸、イ
ソクロトン酸、マレイン酸などの不飽和カルボン酸とエ
チレングリコール、トリエチレングリコール、テトラエ
チレングリコール、トリメチロールプロパン、！、３−
ブタンジオール。Monomers such as acrylonitrile and acrylamide, unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, and maleic acid, and ethylene glycol, triethylene glycol, tetraethylene glycol, trimethylolpropane,! , 3-
Butanediol.
ペンタエリトリトール、ジペンタエリトリトールなどの
脂肪族多価ポリオール化合物とのエステル、更にポリイ
ソシアネート（必要に応じてポリオール類と反応させて
おいてもよい）と不飽和二重結合を含むアルコール、ア
ミン類の重付加反応により合成されるウレタンアクリレ
ート類、ウレタンメタクリレート類およびエポキシ樹脂
とアクリル酸またはメタクリル酸との付加反応により合
成されるエポキシアクリレート類およびポリエステルア
クリレート類、スピンアクリレート類などがあげられる
。Esters with aliphatic polyhydric polyol compounds such as pentaerythritol and dipentaerythritol, as well as polyisocyanates (which may be reacted with polyols as necessary) and alcohols and amines containing unsaturated double bonds. Examples include urethane acrylates and urethane methacrylates synthesized by a polyaddition reaction, epoxy acrylates and polyester acrylates synthesized by an addition reaction between an epoxy resin and acrylic acid or methacrylic acid, and spin acrylates.
またポリマーとしては、主鎖にポリアルキル。Also, as a polymer, the main chain is polyalkyl.
ポリエーテル、ポリエステル、ポリウレタンなどの骨格
を有し、側鎖にアクリル基、メタクリル基。It has a skeleton of polyether, polyester, polyurethane, etc., and has acrylic and methacrylic groups in the side chains.
シンナモイル基、シンナミリデンアセチル基、フリルア
クリロイル基などに代表される重合性の反応基を導入し
たものがあげられるが、本発明はこれらに限定されるも
のではない。Examples include those into which polymerizable reactive groups such as a cinnamoyl group, a cinnamylideneacetyl group, and a furyl acryloyl group are introduced, but the present invention is not limited thereto.
また本発明の光重合性組成物には、使用目的に併せて、
さらに公知のバインダー、着色剤、ＵＶ吸収剤、可塑剤
、熱重合防止剤などの添加剤を必要に応じて含有させる
ことができる。In addition, the photopolymerizable composition of the present invention includes, in accordance with the purpose of use,
Furthermore, known additives such as binders, colorants, UV absorbers, plasticizers, and thermal polymerization inhibitors can be included as necessary.
バインダーとしては有機高分子重合体であればどのよう
なものを使用しても構わない。この様な有機高分子重合
体として、ポリメチルアクリレート、ポリエチルアクリ
レートなどのポリアクリル酸アルキルエステル類、ポリ
メチルメタクリレート、ポリエチルメタクリレートなど
のポリメタクリル酸アルキルエステル類、またはメタク
リル酸共重合体、アクリル酸共重合体、マレイン酸共重
合体または塩素化ポリエチレン、塩素化ポリプロピレン
などの塩素化ポリオレフィン、ポリ塩化ビニル、ポリ塩
化ビニリデン、ポリアクリロニトリルまたはこれらの共
重合体、更にポリビニルアルキルエーテル、ポリエチレ
ン、ポリプロ・ピレン。Any organic polymer may be used as the binder. Examples of such organic polymers include polyacrylic acid alkyl esters such as polymethyl acrylate and polyethyl acrylate, polymethacrylic acid alkyl esters such as polymethyl methacrylate and polyethyl methacrylate, methacrylic acid copolymers, and acrylic. Acid copolymers, maleic acid copolymers or chlorinated polyolefins such as chlorinated polyethylene and chlorinated polypropylene, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile or copolymers thereof, as well as polyvinyl alkyl ether, polyethylene, polypropylene, etc. Pirene.
ポリスチレン、ポリアミド、ポリウレタン、塩素化ゴム
、セルロース誘導体、ポリビニルアルコール、ポリビニ
ルピロリドンなどがあげられるが、本発明はこれらに限
定されるものではない。Examples include polystyrene, polyamide, polyurethane, chlorinated rubber, cellulose derivatives, polyvinyl alcohol, and polyvinylpyrrolidone, but the present invention is not limited thereto.
これらのポリマーは単一で用いても適当な比で２種以上
混合して用いてもよい。またバインダーとして相溶、非
相溶に限らずワックス類を用いても構わない。これらの
ポリマーは全組成中に任意な量を混和させることができ
る。These polymers may be used alone or in a mixture of two or more in an appropriate ratio. Furthermore, waxes may be used as binders, regardless of whether they are compatible or incompatible. Any amount of these polymers can be mixed into the total composition.
着色剤は、光学的に認識できる画像を形成するために含
有させる成分であり、各種顔料、染料が適宜用いられる
。このような顔料、染料の例としては、カーボンブラッ
クや黄鉛、モリブデン赤。The colorant is a component contained in order to form an optically recognizable image, and various pigments and dyes are used as appropriate. Examples of such pigments and dyes are carbon black, yellow lead, and molybdenum red.
ベンガラ等の無機顔料、ハンザイエロー、ベンジジンイ
エロー、ブリリアントカーミン６Ｂ、 レークレッド
Ｃ，パーマネントレッドＦ５Ｒ，フタロシアニンブルー
、ビクトリアブルーレーク、ファストスカイブルー等の
有機顔料、ロイコ染料、フタロシアニン染料等の着色剤
などがあげられる。Inorganic pigments such as Red Garla, organic pigments such as Hansa Yellow, Benzidine Yellow, Brilliant Carmine 6B, Lake Red C, Permanent Red F5R, Phthalocyanine Blue, Victoria Blue Lake, Fast Sky Blue, and coloring agents such as leuco dyes and phthalocyanine dyes. can give.
ＵＶ吸収剤としては、ベンゾフェノン系、サリシレート
系、ベンゾトリアゾール系、修酸アリニド系の化合物な
どがあげられる。Examples of UV absorbers include benzophenone-based, salicylate-based, benzotriazole-based, and oxalinide-based compounds.
可塑剤としては、ジメチルフタレート、ジエチルフタレ
ートなどのフタル酸エステル類、ジメチルグリコールフ
タレート、メチルフタルエチルグリコレートなどのグリ
コールエステル類、トリフェニルフオスヘートなどの燐
酸エステル類、ジオクチルアジペート、ジオチルアゼレ
ート、ジブチルマレートなどの脂肪族二塩基酸エステル
類などがあげられる。Examples of plasticizers include phthalate esters such as dimethyl phthalate and diethyl phthalate, glycol esters such as dimethyl glycol phthalate and methyl phthalethyl glycolate, phosphoric esters such as triphenyl phosphate, dioctyl adipate, diotyl azelate, Examples include aliphatic dibasic acid esters such as dibutyl maleate.
熱重合防止剤としては、ｐ−メトキシフェノール。As a thermal polymerization inhibitor, p-methoxyphenol is used.
ヒドロキノン、ｔ−ブチルカテコール塩化第一銅。Hydroquinone, t-butylcatechol cuprous chloride.
２．６−ジーｔ−ブチル−ｐ−クレゾール、有機酸銅な
どがある。Examples include 2.6-di-t-butyl-p-cresol and organic acid copper.
本発明の光重合性組成物は前述の諸成分を使用目的に併
せて適宜混合して用いられる。例えば、感光性平版印刷
版に使用するには、前記した本発明の成分の混合物を適
当な溶剤に溶かし、プラスチック（ポリエチレン、ポリ
プロピレン、ポリスチレンなど）や、金属板（アルミ、
亜鉛など）などの支持体上に塗布して感光層とし、高圧
水銀灯。The photopolymerizable composition of the present invention is used by appropriately mixing the various components described above depending on the purpose of use. For example, for use in photosensitive lithographic printing plates, a mixture of the components of the present invention described above is dissolved in a suitable solvent, and plastics (polyethylene, polypropylene, polystyrene, etc.) or metal plates (aluminum, polystyrene, etc.) or metal plates (aluminum,
It is coated on a support such as zinc to form a photosensitive layer, and is used as a high-pressure mercury lamp.
蛍光灯、Ｘｅランプなどの光源を用いて画像露光した後
、現像液で処理して感光層の末露光部を除去し、最後に
ガム液を塗布すればよい。本発明の光重合性組成物は高
い感度を有し、版作製の時間短縮に有効である。After imagewise exposure using a light source such as a fluorescent lamp or a Xe lamp, processing with a developer may be performed to remove the end-exposed portions of the photosensitive layer, and finally a gum solution may be applied. The photopolymerizable composition of the present invention has high sensitivity and is effective in shortening the time for plate production.
また本発明の光重合性組成物は、光重合反応を利用した
画像形成方法の記録媒体として使用できる。Further, the photopolymerizable composition of the present invention can be used as a recording medium in an image forming method using a photopolymerization reaction.
特に本出願人の提案した特開昭６２−１７４１９５号に
開示されている画像形成方法の記録媒体として好適であ
る。It is particularly suitable as a recording medium for the image forming method proposed by the present applicant in Japanese Patent Laid-Open No. 174195/1983.
特開昭６２−１７４１９５号の画像形成方法は、複数種
のエネルギーが付与されることによって転写特性が変化
する転写記録層を有する転写記録媒体に、前記複数種の
うち少なくとも一種のエネルギーを記録情報に対応させ
て付与する条件で前記複数種のエネルギーを付与させて
転写像を形成し、その後この転写像を被記録体に転写す
るものである。The image forming method disclosed in JP-A-62-174195 applies at least one type of energy among the plurality of types of energy to a transfer recording medium having a transfer recording layer whose transfer characteristics change when a plurality of types of energy are applied to record information. A transferred image is formed by applying the plurality of types of energy under conditions corresponding to the applied conditions, and then this transferred image is transferred to a recording medium.
以下に前記画像形成方法について詳しく説明する。以下
の説明では複数種のエネルギーとして光エネルギーと熱
エネルギーを用い、熱エネルギーを記録情報に対応させ
て転写記録層に付与する場合を例とする。The image forming method will be described in detail below. In the following description, optical energy and thermal energy are used as the plurality of types of energy, and a case where the thermal energy is applied to the transfer recording layer in correspondence with recorded information will be exemplified.
この画像形成方法で使用する転写記録媒体は、支持体上
に転写記録層を設けたもので、転写記録層には少なくと
も本発明の光重合性組成物と着色剤とを含有し、常温で
面相のものである。この転写記録層は、軟化温度Ｔｓ以
上の温度において粘度が急激に減少する。The transfer recording medium used in this image forming method is one in which a transfer recording layer is provided on a support, and the transfer recording layer contains at least the photopolymerizable composition of the present invention and a colorant. belongs to. The viscosity of this transfer recording layer decreases rapidly at a temperature equal to or higher than the softening temperature Ts.
この画像形成方法では、前記転写記録層に含有する光重
合開始剤の吸収波長に対応した光を一様に照射し、同時
に記録情報に応じてサーマルヘッド等の加熱手段を用い
て転写記録層をＴｓ以上の温度に部分的に加熱して転写
記録層中に転写像を形成する。すなわち、Ｔｓ以上に加
熱された部分は粘度が急激に低下し、転写記録層中の光
重合開始剤およびエチレン性不飽和二重結合を有する化
合物の拡散速度が増加し、重合反応が急激に進む。−方
、非加熱部においては、転写記録層の粘度が下らないた
め光重合開始剤及びエチレン性不飽和二重結合を有する
化合物の拡散が十分でなく、重合反応は部分的に生ずる
だけである。この重合反応の差により転写記録層に転写
像が形成される。In this image forming method, the transfer recording layer is uniformly irradiated with light corresponding to the absorption wavelength of the photopolymerization initiator contained in the transfer recording layer, and at the same time, the transfer recording layer is heated using a heating means such as a thermal head according to recorded information. A transferred image is formed in the transfer recording layer by partially heating to a temperature higher than Ts. That is, the viscosity of the portion heated above Ts sharply decreases, the diffusion rate of the photopolymerization initiator and the compound having an ethylenically unsaturated double bond in the transfer recording layer increases, and the polymerization reaction rapidly progresses. . On the other hand, in the non-heated area, the viscosity of the transfer recording layer does not decrease, so the photopolymerization initiator and the compound having an ethylenically unsaturated double bond do not diffuse sufficiently, and the polymerization reaction occurs only partially. A transfer image is formed on the transfer recording layer due to this difference in polymerization reaction.
こうして転写像の形成された記録媒体を被記録体と圧接
し、所定の温度に加熱、例えばＴｓ以上の温度に加熱す
れば、サーマルヘッドの非加熱部、すなわち重合反応が
部分的にしか生じていない部分は、被記録体に転写され
、サーマルヘッドの加熱部は重合反応が十分に進んでい
るため、被記録体に対する接着性が非加熱部に比べて小
さいため被記録体に転写しない。If the recording medium on which the transferred image has been formed is brought into pressure contact with the recording medium and heated to a predetermined temperature, for example, to a temperature higher than Ts, the polymerization reaction will occur only partially in the non-heated part of the thermal head. The non-heated portion is transferred to the recording medium, and since the polymerization reaction has sufficiently progressed in the heated portion of the thermal head, the adhesion to the recording medium is smaller than that of the non-heated portion, so it is not transferred to the recording medium.
上記の如（して光エネルギーと熱エネルギーによって被
記録体上に画像が形成される。As described above, an image is formed on the recording medium using light energy and thermal energy.
上記の例では転写記録層の転写特性及び重合反応量を支
配する物性値として転写記録層の軟化温度Ｔｓで説明し
たが、この他にも転写記録層のガラス転位点、溶融温度
等を利用してもかまわない。In the above example, the softening temperature Ts of the transfer recording layer was explained as a physical property value that controls the transfer characteristics and polymerization reaction amount of the transfer recording layer, but in addition to this, the glass transition point, melting temperature, etc. of the transfer recording layer can be used. It doesn't matter.
転写記録層は支持体上に転写記録層が連続的に塗布され
た連続層であってもかまわないし、また転写記録層の材
料を粒子状の素体に形成し、粒子状素体分布層として構
成してもかまわない。更に粒子状素体を、本発明の光重
合性組成物を芯剤としたマイクロカプセルで構成されて
いてもよい。The transfer recording layer may be a continuous layer in which the transfer recording layer is continuously coated on a support, or the material of the transfer recording layer may be formed into a particulate element and used as a particulate element distribution layer. You can configure it. Furthermore, the particulate element may be composed of microcapsules using the photopolymerizable composition of the present invention as a core material.
また転写記録層を粒子状素体あるいはマイクロカプセル
で構成し、各素体あるいは各マイクロカプセルが、複数
の色調のうちのいずれか一種の色調となるように着色剤
を含有し、かつ各粒子状素体または各マイクロカプセル
が含有する光重合開始剤の感光波長域を呈する色調に対
応して変えることで多色画像の形成が可能となる。In addition, the transfer recording layer is composed of particulate elements or microcapsules, each element or each microcapsule contains a coloring agent so as to have one of a plurality of color tones, and each particle By changing the photosensitive wavelength range of the photopolymerization initiator contained in the element or each microcapsule in accordance with the color tone, it is possible to form a multicolor image.
以下に多色の画像形成方法を説明する。A multicolor image forming method will be described below.
第１ａ図〜第１Ｃ図において、転写記録媒体１は支持体
ｌｂ上に転写記録層１ａを設けて構成される。In FIGS. 1a to 1C, a transfer recording medium 1 is constructed by providing a transfer recording layer 1a on a support lb.
転写記録層１ａは微小な画像形成素体３１の分布層、と
なっていて、各画像形成素体３１は異なる色調を呈する
着色剤を含んでいる。例えば第１ａ図〜第１ｃ図におい
ては、画像形成素体３１はイエロー（Ｙ）、マゼンタ（
Ｍ）、シアン（Ｃ）のいずれかの着色剤が含有されてい
る。また、Ｙ、Ｍ、Ｃの各素体３１は、含有する着色剤
の色調に対応した感光波長域を有する光重合開始剤をそ
れぞれ含有している。The transfer recording layer 1a is a layer in which minute image forming elements 31 are distributed, and each image forming element 31 contains a coloring agent exhibiting a different color tone. For example, in FIGS. 1a to 1c, the image forming element 31 is yellow (Y), magenta (
M) or cyan (C). Further, each of the Y, M, and C element bodies 31 contains a photopolymerization initiator having a photosensitive wavelength range corresponding to the color tone of the colorant contained therein.
こうして、まず記録媒体ｌをサーマルヘッド２゜に重ね
、サーマルヘッド２０の発熱部全域をカバーする様にＹ
の画像形成素体中の光重合゛開始剤の感光波長域に対応
したλ（Ｙ）の波長の光を照射するとともに、サーマル
ヘッド２０の発熱素子２０ｂ、 ２０ｄ。In this way, first, the recording medium l is stacked on the thermal head 2°, and the Y
The heating elements 20b and 20d of the thermal head 20 emit light with a wavelength of λ(Y) corresponding to the sensitive wavelength range of the photopolymerization initiator in the image forming element.
２０ｅ、 ２０ｆを発熱させる。するとＹの着色剤を含
有する画像形成素体のうち、熱と波長λ（Ｙ）の光が共
に付与された画像形成素体（第１ａ図のハツチングされ
た部分）のみ重合反応が急激におこり硬化する。20e and 20f generate heat. Then, among the image forming elements containing the Y colorant, a polymerization reaction rapidly occurred only in the image forming element to which both heat and light of wavelength λ(Y) were applied (hatched area in Figure 1a). harden.
次に第１ｂ図に示すように転写記録層１ａにＭの画像形
成素体中の光重合開始剤の感光波長域に対応したλ（Ｍ
）の波長の光を照射するとともに、サーマルヘッド２０
の発熱素子２０ａ、２０ｅ、２０ｆを発熱させる。する
とＹと同様に熱と波長λ（Ｍ）の光が共に付与されたＭ
のカプセル（第１ｂ図のハツチングされた部分）のみ重
合反応が急激におこり硬化する。Next, as shown in FIG. 1b, the transfer recording layer 1a is coated with λ(M
), and the thermal head 20
The heating elements 20a, 20e, and 20f generate heat. Then, like Y, M is given both heat and light of wavelength λ(M).
The polymerization reaction occurs rapidly and hardens only in the capsule (hatched area in Figure 1b).
さらにＣの画像形成素体中の光重合開始剤の感応波長域
に対応したλ（Ｃ）の波長の光を照射するとともに、サ
ーマルヘッド２０の発熱素子２０ａ、 ２０ｂ。Further, the heating elements 20a and 20b of the thermal head 20 are irradiated with light having a wavelength of λ(C) corresponding to the sensitive wavelength range of the photopolymerization initiator in the image forming element C.
２０ｃ、 ２０ｅ、 ２０ｆを発熱させることで前記Ｙ
−，Ｍの場合と同様に熱とλ（Ｃ）の光が共に付与され
たＣのカプセル（第１ｃ図のハツチングされた部分）の
み重合反応が急激におこり硬化する。By generating heat in 20c, 20e, and 20f, the Y
As in the case of - and M, only the capsule of C (hatched area in Fig. 1c) to which both heat and light of λ(C) are applied undergoes a polymerization reaction rapidly and is cured.
上記の如くして形成された転写像は、被記録体と圧接し
て所定の温度に加熱することで被記録体に転写（すなわ
ち第１Ｃ図のハツチングされていないＹ、Ｍ、Ｃの画像
形成素体３１が転写）する。The transferred image formed as described above is transferred to the recording medium by pressing it against the recording medium and heating it to a predetermined temperature (i.e., forming images of Y, M, and C not hatched in FIG. 1C). The element body 31 is transferred).
上述の画像形成方法の記録媒体に本発明の光重合性組成
物を用いると、本発明の光重合性組成物は高い光感度を
有するため、記録媒体の加熱時間が短縮され従って記録
速度が向上する。When the photopolymerizable composition of the present invention is used in the recording medium of the above-described image forming method, since the photopolymerizable composition of the present invention has high photosensitivity, the heating time of the recording medium is shortened and the recording speed is improved. do.
また一般式（１）で示される化合物は、優れた分光特性
を有するため、多色画像形成時における感光波長域の重
なりが少な（、従って鮮明な多色画像が得られる。Further, since the compound represented by the general formula (1) has excellent spectral properties, there is little overlap in the sensitive wavelength range during multicolor image formation (therefore, a clear multicolor image can be obtained).
本発明の光重合性組成物を、上記の記録媒体に使用する
場合、光重合性組成物の含有量は転写記録層に対して２
０〜９５重量％が好ましく、着色剤の含有量は０．１〜
３０重量％、バインダーの含有量は０〜８０重量％が好
ましい。When the photopolymerizable composition of the present invention is used in the above-mentioned recording medium, the content of the photopolymerizable composition is 2% relative to the transfer recording layer.
The content of the coloring agent is preferably 0 to 95% by weight, and the content of the colorant is 0.1 to 95% by weight.
30% by weight, and the binder content is preferably 0 to 80% by weight.
以下実施例で本発明の光重合性組成物を具体的に説明す
る。The photopolymerizable composition of the present invention will be specifically explained in Examples below.
実施例１）〜７）、比較例１）
（感光層の調整）
エチレン性不飽和二重結合を有する化合物として、東亜
合成化学工業（株）製のアロニクスＭ−２０５を２０ｇ
１バインダーとしてデュポン社製のＰＭＭＡ２０１０を
１５ｇ１光重合開始剤として第１表に示す一般式（Ｉ）
の化合物を１ｇ１アミンとしてエチル−ｐ−ジメチルア
ミノベンゾエートを０．８ｇ、着色剤として日本化薬社
製カヤセットブルー１３６を０．Ｉｇ、以上のものをジ
クロロメタン約２００ｍ ｌに溶かし、スビナ−を用い
てアルミニウム板上に塗布した後、これを６０℃、１０
分間乾燥させて厚さ約５μｍの感光層とした。次に前記
感光層の上に酸素防止層としてＰＶＡ （ポリビニルア
ルコール）を３μｍの厚さで塗布し試料とした。Examples 1) to 7), Comparative Example 1) (Adjustment of photosensitive layer) As a compound having an ethylenically unsaturated double bond, 20 g of Aronix M-205 manufactured by Toagosei Chemical Industry Co., Ltd.
1 15g of PMMA2010 manufactured by DuPont as a binder 1 General formula (I) shown in Table 1 as a photoinitiator
0.8 g of ethyl-p-dimethylaminobenzoate and 0.8 g of Kayaset Blue 136 manufactured by Nippon Kayaku Co., Ltd. as a coloring agent. Ig, the above was dissolved in about 200 ml of dichloromethane, coated on an aluminum plate using a tinner, and then heated at 60°C for 10 minutes.
The photosensitive layer was dried for a minute to form a photosensitive layer with a thickness of about 5 μm. Next, PVA (polyvinyl alcohol) was applied as an oxygen prevention layer to a thickness of 3 μm on the photosensitive layer to prepare a sample.
（感度の測定）
試料上に光学楔（光学濃度０〜１５段）を置き、１００
ｗ高圧水銀灯で３０秒間露光した後、ＰＶＡを水洗除去
し、さらに感光層を１．１．１−トリクロロエタンで３
０秒間処理して現出した画像の対応する光学楔の最高段
数を試料の感度とした。その結果を第１表に示す。また
、第１表には一般式（Ｉ）の化合物のかわりにベンゾイ
ンエチルエーテルを用いた比較例１）を併せて示した。(Measurement of sensitivity) Place an optical wedge (optical density 0 to 15 steps) on the sample and
After exposure with a high-pressure mercury lamp for 30 seconds, the PVA was removed by washing with water, and the photosensitive layer was further diluted with 1.1.1-trichloroethane.
The highest number of optical wedges corresponding to the image that appeared after processing for 0 seconds was taken as the sensitivity of the sample. The results are shown in Table 1. Table 1 also shows Comparative Example 1) in which benzoin ethyl ether was used instead of the compound of general formula (I).
第 １ 表
実施例８）〜１５）、比較例２）
本発明の光重合性組成物を、前述の特開昭６２−１７４
１９５号に記載の画像形成方法で用いる記録媒体に使用
した。Table 1 Examples 8) to 15), Comparative Example 2) The photopolymerizable composition of the present invention
It was used in a recording medium used in the image forming method described in No. 195.
（記録媒体の作製）
第 ２ 表
先ず、第２表に示す成分１０ｇを塩化メチレン２０重量
部に混合したものを、カチオン又はノニオン等ＨＬＢ値
の少なくとも１０以上の界面活性剤とゼラチンＩｇを溶
解した水２００ ｍ ！！に混合し、６０℃加温下ホモ
ミキサーによって８ 、 ＯＯＯ〜１０ 、 ＯＯＯｒ
ｐ ｍで撹拌して乳化し、平均粒径２６μｍの油滴を
得た。(Preparation of Recording Medium) Table 2 First, 10 g of the ingredients shown in Table 2 were mixed with 20 parts by weight of methylene chloride, and a surfactant such as a cationic or nonionic surfactant having an HLB value of at least 10 or more and gelatin Ig were dissolved. 200m of water! ! 8, OOO~10, OOOr with a homomixer under heating at 60°C
The mixture was emulsified by stirring at pm to obtain oil droplets with an average particle size of 26 μm.
更に６０℃下で撹拌を３０分間続けて塩化メチレンを留
去することにより油滴の平均粒径を１０μｍにした。Further, stirring was continued for 30 minutes at 60° C., and methylene chloride was distilled off, so that the average particle size of the oil droplets was adjusted to 10 μm.
これにアラビアゴム１ｇを溶かした水２０ｍｊ！を加え
、ゆっくり冷却しながら、ＮＨ４ＯＨ（アンモニア）水
を添加しｐＨ１１以上にすることによってマイクロカプ
セルスラリーを得、グルタルアルデヒド２０％水溶液１
．Ｏｍｊ！をゆっくり加えてカプセル壁を硬化した。そ
の後ヌツチェ濾過器で固液分離し、真空乾燥器で３５℃
、１０時間乾燥してマイクロカプセル状の画像形成素体
を得た。20mj of water with 1g of gum arabic dissolved in this! was added, and while cooling slowly, NH4OH (ammonia) water was added to adjust the pH to 11 or higher to obtain a microcapsule slurry, and a glutaraldehyde 20% aqueous solution 1
．． Omj! was added slowly to harden the capsule wall. After that, solid-liquid separation was carried out using a Nutsche filter, and then a vacuum dryer was used at 35°C.
, and was dried for 10 hours to obtain a microcapsule-shaped image forming element.
この画像形成素体は第２図に示す様にコア１ｃがシェル
１ｄで被覆されたマイクロカプセルで粒径７〜１５μｍ
１平均粒径が１０μｍのものであった。As shown in Fig. 2, this image forming element is a microcapsule in which a core 1c is covered with a shell 1d and has a particle size of 7 to 15 μm.
1 average particle size was 10 μm.
次に支持体であるＰＥＴフィルムｌｂ上に接着層１ｆと
して日本合成化学工業（株）のポリエステル系接着材Ｌ
Ｐ−０２２を約１μｍの厚さで塗布した。Next, a polyester adhesive L manufactured by Nippon Gosei Kagaku Kogyo Co., Ltd.
P-022 was applied to a thickness of approximately 1 μm.
この接着層の上に前記マイクロカプセルを過剰量振りか
け、接着材に付着していない余分なマイクロカプセルを
払い落し記録媒体とした。An excessive amount of the microcapsules was sprinkled onto the adhesive layer, and the excess microcapsules not attached to the adhesive were brushed off to obtain a recording medium.
次のこの転写記録媒体を互いに１ｋｇｆ／ｃｒｒｆで圧
接し、それぞれが直径４０ｍｍのアルミローラの上に硬
度７０度のシリコンゴムを１ ｍ ｍ厚に被覆したロー
ラ間に３００ ｍ ｍ ／ ｍ ｉ ｎ 、の速度にな
る様通した。Next, these transfer recording media are pressed against each other at 1 kgf/crrf, and each roller is coated with 1 mm thick silicone rubber having a hardness of 70 degrees on an aluminum roller with a diameter of 40 mm. It seemed like it would be at a speed of .
またこの時ローラの表面温度はそれぞれ８０℃になる様
保持しておいた。ローラ間を通過した後、結着材上の画
像形成素体はＰＥＴフィルムに強固に固定されていた。At this time, the surface temperature of each roller was maintained at 80°C. After passing between the rollers, the image forming element on the binder was firmly fixed to the PET film.
以上により第２図に示す転写記録媒体１を得た。Through the above steps, the transfer recording medium 1 shown in FIG. 2 was obtained.
（感度評価）
どうして作成した転写記録媒体１をロール状に巻き回し
て第３図に示す装置に組み込んだ。(Evaluation of Sensitivity) The prepared transfer recording medium 1 was wound into a roll and incorporated into the apparatus shown in FIG.
サーマルヘッド２０としては８ドツト／ ｍ ｍのＡ−
４サイズのライン・タイプで発熱素子列がエツジ部に配
列されているものを用い、転写記録媒体１のテンション
により発熱素子に押圧される様にした。The thermal head 20 has 8 dots/mm A-
Four sizes of line type sheets were used in which heat generating element rows were arranged at the edge portions, and the heat generating elements were pressed by the tension of the transfer recording medium 1.
そして対向した部所でケミカルランプ３を配置した。Then, chemical lamps 3 were placed at opposing locations.
ケミカルランプ３には光重合開始剤の感光波長域に合せ
てピーク波長３３５ｎｍの東芝製ＦＩＯＡ７０Ｅ３５／
３３Ｔ１５を用いた。The chemical lamp 3 is a Toshiba FIOA70E35/FIOA70E35 with a peak wavelength of 335 nm, matching the sensitive wavelength range of the photopolymerization initiator.
33T15 was used.
次に画信号に応じてサーマルヘッドの発熱を制御する。Next, the heat generation of the thermal head is controlled according to the image signal.
本実施例においては光と熱が与えられて軟化温度が上昇
して転写開始温度が上昇する転写記録層を扱う為、ネガ
記録となる。即ちサーマルヘッドの制御はマーク信号（
マゼンタ）の場合は通電せずマーク信号でない（白）の
時に通電して発熱させる。この発熱時の通電エネルギー
は０，８ｗ／ ｄ ｏ ｔ Ｘ Ｘ ｍ ｓ ｅ ｃと
しケミカルランプでサーマルヘッドの信号と同期してＸ
ｍ ｓ ｅ ｃ光照射を一様にしながら上記した様な
要領で画信号に応じてサーマルヘッドを制御、駆動し２
Ｘ ｍ ｓ ｅ ｃ ／ ｌ ｉ ｎ ｅの繰り返し
周期で同期して転写記録媒体をステッピングモータとド
ライブゴムロールとで搬送した。In this embodiment, since the transfer recording layer is treated with light and heat, the softening temperature of which increases and the transfer start temperature increases, negative recording is performed. In other words, the control of the thermal head is based on the mark signal (
(magenta), it is not energized and when there is no mark signal (white), it is energized to generate heat. The energizing energy during this heat generation is 0.8w/dot
The thermal head is controlled and driven according to the image signal in the manner described above while uniformizing the msec light irradiation.2
The transfer recording medium was conveyed by a stepping motor and a drive rubber roll in synchronization with a repeating cycle of X msec/line.
ついで第４図に示す様に表面平滑度１０〜３０秒の範囲
にある普通紙１０を転写記録層に重ねて、ヒートロール
８とピンチロール９とで挟んで搬送した。Then, as shown in FIG. 4, a plain paper 10 having a surface smoothness in the range of 10 to 30 seconds was placed on the transfer recording layer, and conveyed while being sandwiched between a heat roll 8 and a pinch roll 9.
ヒートロール８は３００ｗのヒータを内部に持ち、表面
を２ ｍ ｍ厚のシリコンゴムで被覆したアルミロール
で表面を５０〜１５０℃の範囲の任意の温度に操つ様ヒ
ータを制御した。ビンチロール９はＪＩＳゴム硬度計の
硬度５０°のシリコンゴムロールで押圧を１〜１．５Ｋ
ｇ／ｃｒｒｆとした。ヒートロール、１１０℃〜１３０
℃の範囲で、普通紙を転写記録層に重ねて搬送した後、
基材フィルムを剥離し画像が得られる最小時間Ｘ ｍ
ｓ ｅ ｃを求め感度とした（ただしＸは２ ｍ ｓ
ｅ ｃ 、 ５ ｍ ｓ ｅ ｃ 、 １０ ｍ ｓ
ｅ ｃ 、以後５ ｍ ｓ ｅ ｃごとに増やす）。The heat roll 8 had a 300 W heater inside, and the heater was controlled to control the surface to an arbitrary temperature in the range of 50 to 150° C. using an aluminum roll whose surface was coated with 2 mm thick silicone rubber. Vinci Roll 9 is a silicone rubber roll with a hardness of 50° according to the JIS rubber hardness tester, and the pressure is 1 to 1.5K.
g/crrf. Heat roll, 110℃~130
After transporting plain paper over the transfer recording layer in the range of ℃,
Minimum time for peeling off the base film and obtaining an image X m
s e c was calculated and used as the sensitivity (X is 2 m s
e c , 5 m s e c , 10 m s
e c , increasing every 5 m sec thereafter).
すなわちＸの値が小さいほど感度が高いことになる。ま
た得られた画像は定着性よい高品位な画像であった。結
果を第３表に示す。また、第３表には比較例２）として
チバガイギー社製光重合開始剤イルガキュア９０７を用
いた例も示した。That is, the smaller the value of X, the higher the sensitivity. Moreover, the obtained image was a high-quality image with good fixability. The results are shown in Table 3. Table 3 also shows an example using Irgacure 907, a photopolymerization initiator manufactured by Ciba Geigy, as Comparative Example 2).
第 ３ 表
〔発明の効果〕
以上説明したように、本発明の光重合性組成物は、従来
のものより優れた感度を示す。従って、本発明の光重合
性組成物を使用した記録媒体は、高感度となり、記録速
度を速（することができる。Table 3 [Effects of the Invention] As explained above, the photopolymerizable composition of the present invention exhibits sensitivity superior to conventional compositions. Therefore, a recording medium using the photopolymerizable composition of the present invention has high sensitivity and can increase recording speed.
第１ａ図、第１ｂ図、第１Ｃ図は光エネルギーと熱エネ
ルギーを用いた多色の画像記録方法の原理図であり、第
２図は本発明の光重合性組成物を用いた記録媒体の一例
を示す断面図、第３図及び第４図は第２図に示す記録媒
体を用いて転写記録を行なう装置の模式図である。
ｌ・・・・・・・・・・・・・・・・記録媒体１ａ・・
・・・・・・・・・・・・・転写記録層１ｂ・・・・・
・・・・・・・・・・・支持体層１ｃ ・・・・・・・
・・・・・・・・・・・コア１ ｄ ・・・・・・・
・・・・・・・・・・ シ エル１ｆ・・・・・・・・
・・・・・・・・・接着剤２・・・・・・・・・・・・
・・・供給ロール３・・・・・・・・・・・・・・・・
・ランプ２０・・・・・・・・・・・・・サーマルヘッ
ド５・・・・・・・・・・・・・・・・制御回路７・・
・・・・・・・・・・・・・・ Ｉ＝・９・８・・・・
・・・・・・・・・ヒートローラー９・・・・・・・・
・・・・・ピンチローラ・１０・・・・・・・・・・・
・・・・・・普通紙１１・・・・・・・・・・・・・・
巻取りロール１２・・・・・・・・・・・・・・・・記
録画像特許出願人 キャノン株式会社
三洋化成工業株式会社Figures 1a, 1b, and 1C are diagrams showing the principle of a multicolor image recording method using light energy and thermal energy, and Figure 2 shows a recording medium using the photopolymerizable composition of the present invention. 3 and 4, which are cross-sectional views showing an example, are schematic diagrams of an apparatus that performs transfer recording using the recording medium shown in FIG. 2. l・・・・・・・・・・・・・・・Recording medium 1a...
・・・・・・・・・・・・Transfer recording layer 1b・・・・・・
......Support layer 1c...
・・・・・・・・・Core 1 d ・・・・・・・・・
・・・・・・・・・ Ciel 1f・・・・・・・・・
・・・・・・・・・Adhesive 2・・・・・・・・・・・・
・・・Supply roll 3・・・・・・・・・・・・・・・・・・
・Lamp 20・・・・・・・・・・・・Thermal head 5・・・・・・・・・・・・・・・Control circuit 7
・・・・・・・・・・・・・・・ I=・9・8・・・・
・・・・・・・・・Heat roller 9・・・・・・・・・
・・・・・・Pinch roller・10・・・・・・・・・・・・・
・・・・・・Plain paper 11・・・・・・・・・・・・・・・
Winding roll 12... Recorded image patent applicant Canon Co., Ltd. Sanyo Chemical Industries, Ltd.
Claims (2)
る化合物および下記一般式（ I ）で示される光重合開
始剤を含有することを特徴とする光重合性組成物。 ▲数式、化学式、表等があります▼‐‐‐‐‐‐‐‐‐
‐（ I ） （式中、Ｘは−Ｓ−、−ＳＯ−あるいは−ＳＯ＿２−。 Ｒ＿１は水素原子、炭素数１〜６のアルキル基、アルコ
キシ基あるいはハロゲン原子。 Ａｒ＿１，Ａｒ＿２は置換基を有してもよい芳香環ある
いは複素環。）(1) A photopolymerizable composition comprising a compound having an ethylenically unsaturated double bond capable of addition polymerization and a photopolymerization initiator represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼‐‐‐‐‐‐‐‐‐
-(I) (wherein, aromatic ring or heterocycle that may be used.)
くとも一種のエネルギーを画像記録情報に対応させて同
時に付与することにより、その転写特性を支配する物性
が変化する転写記録層を支持体上に有する記録媒体であ
って、該転写記録層が少なくとも着色剤と、付加重合可
能なエチレン性不飽和二重結合を有する化合物および下
記一般式（ I ）で示される光重合開始剤を含有する光
重合性組成物とを含むことを特徴とする記録媒体。 ▲数式、化学式、表等があります▼‐‐‐‐‐‐‐‐‐
‐‐（ I ） （式中、Ｘは−Ｓ−、−ＳＯ−あるいは−ＳＯ＿２−。 Ｒ＿１は水素原子、炭素数１〜６のアルキル基、アルコ
キシ基あるいはハロゲン原子。 Ａｒ＿１，Ａｒ＿２は置換基を有してもよい芳香環ある
いは複素環。）(2) Recording having a transfer recording layer on a support whose physical properties governing the transfer characteristics change by simultaneously applying at least one type of light energy and thermal energy in correspondence with image recording information. A photopolymerizable composition in which the transfer recording layer contains at least a colorant, a compound having an ethylenically unsaturated double bond capable of addition polymerization, and a photopolymerization initiator represented by the following general formula (I). A recording medium characterized by containing an object. ▲There are mathematical formulas, chemical formulas, tables, etc.▼‐‐‐‐‐‐‐‐‐
--(I) (In the formula, (optional aromatic ring or heterocycle)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8194388A JPH01253732A (en) | 1988-04-01 | 1988-04-01 | Photopolymerizable composition and recording medium using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8194388A JPH01253732A (en) | 1988-04-01 | 1988-04-01 | Photopolymerizable composition and recording medium using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01253732A true JPH01253732A (en) | 1989-10-11 |
Family
ID=13760582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8194388A Pending JPH01253732A (en) | 1988-04-01 | 1988-04-01 | Photopolymerizable composition and recording medium using same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01253732A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003064050A (en) * | 2001-08-22 | 2003-03-05 | Toagosei Co Ltd | New (meth)acrylicester and curable composition containing the (meth)acrylic ester |
| ITVA20120010A1 (en) * | 2012-05-03 | 2013-11-04 | Lamberti Spa | ALPHA-DICHETONES FOR PHOTOPOLYMERIZATION BY LED |
-
1988
- 1988-04-01 JP JP8194388A patent/JPH01253732A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003064050A (en) * | 2001-08-22 | 2003-03-05 | Toagosei Co Ltd | New (meth)acrylicester and curable composition containing the (meth)acrylic ester |
| ITVA20120010A1 (en) * | 2012-05-03 | 2013-11-04 | Lamberti Spa | ALPHA-DICHETONES FOR PHOTOPOLYMERIZATION BY LED |
| WO2013164394A1 (en) * | 2012-05-03 | 2013-11-07 | Lamberti Spa | Alpha-diketones for led photocuring |
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