JP5354242B2 - 活性エネルギー線硬化性樹脂組成物および印刷インキ - Google Patents
活性エネルギー線硬化性樹脂組成物および印刷インキ Download PDFInfo
- Publication number
- JP5354242B2 JP5354242B2 JP2007052131A JP2007052131A JP5354242B2 JP 5354242 B2 JP5354242 B2 JP 5354242B2 JP 2007052131 A JP2007052131 A JP 2007052131A JP 2007052131 A JP2007052131 A JP 2007052131A JP 5354242 B2 JP5354242 B2 JP 5354242B2
- Authority
- JP
- Japan
- Prior art keywords
- active energy
- energy ray
- resin composition
- curable resin
- rosin
- 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.)
- Active
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 41
- 238000007639 printing Methods 0.000 title claims description 12
- 239000003085 diluting agent Substances 0.000 claims abstract description 23
- 239000005011 phenolic resin Substances 0.000 claims abstract description 17
- 150000002989 phenols Chemical class 0.000 claims abstract description 15
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 alkyl phenols Chemical class 0.000 claims description 45
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 20
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 20
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 20
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 14
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 239000008158 vegetable oil Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920003987 resole Polymers 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000011134 resol-type phenolic resin Substances 0.000 claims description 2
- 238000004945 emulsification Methods 0.000 abstract description 9
- 230000002349 favourable effect Effects 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 58
- 229920005989 resin Polymers 0.000 description 31
- 239000011347 resin Substances 0.000 description 31
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 16
- 150000004665 fatty acids Chemical class 0.000 description 15
- 239000000976 ink Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 10
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 10
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229940040452 linolenate Drugs 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229940049918 linoleate Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000004641 Diallyl-phthalate Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 229940000640 docosahexaenoate Drugs 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 229940066675 ricinoleate Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 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
- RKLJSBNBBHBEOT-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropanoyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)C(=O)OC(=O)C(C)(C)CO RKLJSBNBBHBEOT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- KXZLHMICGMACLR-UHFFFAOYSA-N 2-(hydroxymethyl)-2-pentylpropane-1,3-diol Chemical compound CCCCCC(CO)(CO)CO KXZLHMICGMACLR-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- HHKAGFTWEFVXET-UHFFFAOYSA-N 2-heptyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCCCCCCC(CO)(CO)CO HHKAGFTWEFVXET-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- 235000006667 Aleurites moluccana Nutrition 0.000 description 2
- 244000136475 Aleurites moluccana Species 0.000 description 2
- 235000003301 Ceiba pentandra Nutrition 0.000 description 2
- 244000146553 Ceiba pentandra Species 0.000 description 2
- 241000282994 Cervidae Species 0.000 description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
- PWLNAUNEAKQYLH-UHFFFAOYSA-N Octyl butanoate Chemical compound CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 2
- 235000008753 Papaver somniferum Nutrition 0.000 description 2
- 240000001090 Papaver somniferum Species 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 2
- 240000002834 Paulownia tomentosa Species 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 235000019498 Walnut oil Nutrition 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- XAPCMTMQBXLDBB-UHFFFAOYSA-N butanoic acid hexyl ester Natural products CCCCCCOC(=O)CCC XAPCMTMQBXLDBB-UHFFFAOYSA-N 0.000 description 2
- RPRPDTXKGSIXMD-UHFFFAOYSA-N butyl hexanoate Chemical compound CCCCCC(=O)OCCCC RPRPDTXKGSIXMD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 229940105990 diglycerin Drugs 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229940108623 eicosenoic acid Drugs 0.000 description 2
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 2
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- BYEVBITUADOIGY-UHFFFAOYSA-N ethyl nonanoate Chemical compound CCCCCCCCC(=O)OCC BYEVBITUADOIGY-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000008169 grapeseed oil Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- DILOFCBIBDMHAY-UHFFFAOYSA-N methyl 2-(3,4-dimethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C(OC)=C1 DILOFCBIBDMHAY-UHFFFAOYSA-N 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- IJXHLVMUNBOGRR-UHFFFAOYSA-N methyl nonanoate Chemical compound CCCCCCCCC(=O)OC IJXHLVMUNBOGRR-UHFFFAOYSA-N 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- GJWGZSBNFSBUPX-UHFFFAOYSA-N pentyl octanoate Chemical compound CCCCCCCC(=O)OCCCCC GJWGZSBNFSBUPX-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- IDHBLVYDNJDWNO-UHFFFAOYSA-N propyl octanoate Chemical compound CCCCCCCC(=O)OCCC IDHBLVYDNJDWNO-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 239000008170 walnut oil Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- FVUHGTQDOMGZOT-NTSWFWBYSA-N (1s,3r)-3-methoxycarbonylcyclopentane-1-carboxylic acid Chemical compound COC(=O)[C@@H]1CC[C@H](C(O)=O)C1 FVUHGTQDOMGZOT-NTSWFWBYSA-N 0.000 description 1
- WRJRVEBUZGQDMO-SNPVRQPZSA-N (5Z,8Z,11Z,14Z)-2-butylicosa-5,8,11,14-tetraenoic acid Chemical compound C(CCC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC WRJRVEBUZGQDMO-SNPVRQPZSA-N 0.000 description 1
- YSUSWAQTABKLKV-AILJCPQKSA-N (5Z,8Z,11Z,14Z)-2-hexylicosa-5,8,11,14-tetraenoic acid Chemical compound C(CCCCC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC YSUSWAQTABKLKV-AILJCPQKSA-N 0.000 description 1
- ZFIKOGODLPXNMG-GKFVBPDJSA-N (5Z,8Z,11Z,14Z)-2-propylicosa-5,8,11,14-tetraenoic acid Chemical compound C(CC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC ZFIKOGODLPXNMG-GKFVBPDJSA-N 0.000 description 1
- DSQFSRAJFCOGKA-GKFVBPDJSA-N (5z,8z,11z,14z)-2-ethylicosa-5,8,11,14-tetraenoic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC(CC)C(O)=O DSQFSRAJFCOGKA-GKFVBPDJSA-N 0.000 description 1
- ZEBIJPXNSBSHGD-ZKWNWVNESA-N (5z,8z,11z,14z)-2-methylicosa-5,8,11,14-tetraenoic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCC(C)C(O)=O ZEBIJPXNSBSHGD-ZKWNWVNESA-N 0.000 description 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-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
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- XUQBFMJGHHYFCP-UHFFFAOYSA-N 2-(2-chloroethyl)-3,4,5,6-tetrahydro-1h-2-benzazocine;hydrochloride Chemical compound Cl.C1N(CCCl)CCCCC2=CC=CC=C21 XUQBFMJGHHYFCP-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- PSAAPHZQPIWZFX-HDXUUTQWSA-N 2-ethylhexyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(CC)CCCC PSAAPHZQPIWZFX-HDXUUTQWSA-N 0.000 description 1
- FOKDITTZHHDEHD-PFONDFGASA-N 2-ethylhexyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CC)CCCC FOKDITTZHHDEHD-PFONDFGASA-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
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RLLIKXPTKNBNBZ-YXAHYSCSSA-N 2-methylpropyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(C)C RLLIKXPTKNBNBZ-YXAHYSCSSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FDVCQFAKOKLXGE-UHFFFAOYSA-N 216978-79-9 Chemical compound C1CC(C)(C)C2=CC(C=O)=CC3=C2N1CCC3(C)C FDVCQFAKOKLXGE-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- PHUSOTFVZQDLMC-QXMHVHEDSA-N 3-methylbutyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCC(C)C PHUSOTFVZQDLMC-QXMHVHEDSA-N 0.000 description 1
- FVKRIDSRWFEQME-UHFFFAOYSA-N 3-methylbutyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCC(C)C FVKRIDSRWFEQME-UHFFFAOYSA-N 0.000 description 1
- SGYAMNNIKRWVKZ-UHFFFAOYSA-N 6-(furan-2-yl)hexa-3,5-dien-2-one Chemical compound CC(=O)C=CC=CC1=CC=CO1 SGYAMNNIKRWVKZ-UHFFFAOYSA-N 0.000 description 1
- AMEMLELAMQEAIA-UHFFFAOYSA-N 6-(tert-butyl)thieno[3,2-d]pyrimidin-4(3H)-one Chemical compound N1C=NC(=O)C2=C1C=C(C(C)(C)C)S2 AMEMLELAMQEAIA-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-VAWYXSNFSA-N 9-Octadecenoic acid, ethyl ester Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-VAWYXSNFSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- NDKYEUQMPZIGFN-UHFFFAOYSA-N Butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 description 1
- YPQSPODHFDGVAC-UHFFFAOYSA-N Butyl heptanoate Chemical compound CCCCCCC(=O)OCCCC YPQSPODHFDGVAC-UHFFFAOYSA-N 0.000 description 1
- CZDURLUKJJJBRN-GKFVBPDJSA-N C(C(C)C)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC Chemical compound C(C(C)C)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC CZDURLUKJJJBRN-GKFVBPDJSA-N 0.000 description 1
- QGVXDNRRTQSXRX-GKFVBPDJSA-N C(C)(C)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC Chemical compound C(C)(C)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC QGVXDNRRTQSXRX-GKFVBPDJSA-N 0.000 description 1
- CQARMNKERQKYPZ-UHFFFAOYSA-N C(C=CC=CC=CC=CC=CC=CCCCCCCCCC)(=O)OCC(C)C Chemical compound C(C=CC=CC=CC=CC=CC=CCCCCCCCCC)(=O)OCC(C)C CQARMNKERQKYPZ-UHFFFAOYSA-N 0.000 description 1
- HHVGFXQQBNQVIO-UHFFFAOYSA-N C(CCC)OC(C=CC=CC=CC=CC=CC=CCCCCCCCCC)=O Chemical compound C(CCC)OC(C=CC=CC=CC=CC=CC=CCCCCCCCCC)=O HHVGFXQQBNQVIO-UHFFFAOYSA-N 0.000 description 1
- RNIROMQWNHPJQX-SNPVRQPZSA-N C(CCCC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC Chemical compound C(CCCC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC RNIROMQWNHPJQX-SNPVRQPZSA-N 0.000 description 1
- QCMMAKMFCSCEMD-ATLWAXJLSA-N C(CCCCCC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC Chemical compound C(CCCCCC)C(C(=O)O)CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC QCMMAKMFCSCEMD-ATLWAXJLSA-N 0.000 description 1
- JOFYCKASJMGFLI-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)OCCC.C(CCCCCCCCCCC)(=O)OC=C Chemical compound C(CCCCCCCCCCC)(=O)OCCC.C(CCCCCCCCCCC)(=O)OC=C JOFYCKASJMGFLI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241001071795 Gentiana Species 0.000 description 1
- QOIIBPAJVWFEPE-UHFFFAOYSA-N Heptyl heptanoate Chemical compound CCCCCCCOC(=O)CCCCCC QOIIBPAJVWFEPE-UHFFFAOYSA-N 0.000 description 1
- DGPNTCACXCHFDI-UHFFFAOYSA-N Hexyl decanoate Chemical compound CCCCCCCCCC(=O)OCCCCCC DGPNTCACXCHFDI-UHFFFAOYSA-N 0.000 description 1
- CMBYOWLFQAFZCP-UHFFFAOYSA-N Hexyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCCC CMBYOWLFQAFZCP-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- PKPPDYGHKDIKBH-UHFFFAOYSA-N Isopropyl dodecanoic acid Chemical compound CCCCCCCCCC(=O)OC(C)C PKPPDYGHKDIKBH-UHFFFAOYSA-N 0.000 description 1
- WCGIIHOFOFCKSM-UHFFFAOYSA-N Isopropyl octanoate Chemical compound CCCCCCCC(=O)OC(C)C WCGIIHOFOFCKSM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-ZHACJKMWSA-N Methyl (9E)-9-octadecenoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OC QYDYPVFESGNLHU-ZHACJKMWSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- XAZROQGRFWCMBU-UHFFFAOYSA-N Octyl heptanoate Chemical compound CCCCCCCCOC(=O)CCCCCC XAZROQGRFWCMBU-UHFFFAOYSA-N 0.000 description 1
- DJNTZVRUYMHBTD-UHFFFAOYSA-N Octyl octanoate Chemical compound CCCCCCCCOC(=O)CCCCCCC DJNTZVRUYMHBTD-UHFFFAOYSA-N 0.000 description 1
- PSQMUBJRXIGVIT-UHFFFAOYSA-N Pentyl heptanoate Chemical compound CCCCCCC(=O)OCCCCC PSQMUBJRXIGVIT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UWZVPQKWYFZLLW-UHFFFAOYSA-N Propyl heptanoate Chemical compound CCCCCCC(=O)OCCC UWZVPQKWYFZLLW-UHFFFAOYSA-N 0.000 description 1
- XKGDWZQXVZSXAO-ADYSOMBNSA-N Ricinoleic Acid methyl ester Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC XKGDWZQXVZSXAO-ADYSOMBNSA-N 0.000 description 1
- XKGDWZQXVZSXAO-SFHVURJKSA-N Ricinolsaeure-methylester Natural products CCCCCC[C@H](O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-SFHVURJKSA-N 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 244000111306 Torreya nucifera Species 0.000 description 1
- 235000006732 Torreya nucifera Nutrition 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003831 antifriction material Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Natural products CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 239000002585 base Substances 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
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- SVGGKWILBMPIJV-UTJQPWESSA-N butyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCCC SVGGKWILBMPIJV-UTJQPWESSA-N 0.000 description 1
- QQNROWCMALTXCD-XQOKXTRKSA-N butyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CCCCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC QQNROWCMALTXCD-XQOKXTRKSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-OUKQBFOZSA-N butyl (e)-octadec-9-enoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-OUKQBFOZSA-N 0.000 description 1
- AMUBFTQQLDHNQU-SEYXRHQNSA-N butyl (z)-docos-13-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCCCC AMUBFTQQLDHNQU-SEYXRHQNSA-N 0.000 description 1
- HGWAKQDTQVDVRP-OKULMJQMSA-N butyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCCC HGWAKQDTQVDVRP-OKULMJQMSA-N 0.000 description 1
- ZRNCNTSXSYXHOW-UHFFFAOYSA-N butyl decanoate Chemical compound CCCCCCCCCC(=O)OCCCC ZRNCNTSXSYXHOW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DOLFPCDDMUMIMR-UHFFFAOYSA-N butyl nonanoate Chemical compound CCCCCCCCC(=O)OCCCC DOLFPCDDMUMIMR-UHFFFAOYSA-N 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- VCDLWFYODNTQOT-UHFFFAOYSA-N docosahexaenoic acid methyl ester Natural products CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OC VCDLWFYODNTQOT-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 1
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 1
- WFZQLUSOXHIVKL-QXMHVHEDSA-N ethyl (13Z)-docosenoate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC WFZQLUSOXHIVKL-QXMHVHEDSA-N 0.000 description 1
- ITNKVODZACVXDS-YATCGRJWSA-N ethyl (4e,7e,10e,13e,16e,19e)-docosa-4,7,10,13,16,19-hexaenoate Chemical compound CCOC(=O)CC\C=C\C\C=C\C\C=C\C\C=C\C\C=C\C\C=C\CC ITNKVODZACVXDS-YATCGRJWSA-N 0.000 description 1
- AZXVZUBIFYQWJK-KWRJMZDGSA-N ethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC AZXVZUBIFYQWJK-KWRJMZDGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940031016 ethyl linoleate Drugs 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- JYYFMIOPGOFNPK-AGRJPVHOSA-N ethyl linolenate Chemical compound CCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC JYYFMIOPGOFNPK-AGRJPVHOSA-N 0.000 description 1
- 229940090028 ethyl linolenate Drugs 0.000 description 1
- JYYFMIOPGOFNPK-UHFFFAOYSA-N ethyl linolenate Natural products CCOC(=O)CCCCCCCC=CCC=CCC=CCC JYYFMIOPGOFNPK-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- ZYNDJIBBPLNPOW-UHFFFAOYSA-N eurucic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCCCCCC(=O)OC ZYNDJIBBPLNPOW-UHFFFAOYSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XSCIEKYDPGHXMD-YPKPFQOOSA-N heptyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCCCCC XSCIEKYDPGHXMD-YPKPFQOOSA-N 0.000 description 1
- MPLLSYWBBPPERF-UHFFFAOYSA-N heptyl decanoate Chemical compound CCCCCCCCCC(=O)OCCCCCCC MPLLSYWBBPPERF-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ARSLOAKOWGOSEX-UHFFFAOYSA-N heptyl nonanoate Chemical compound CCCCCCCCC(=O)OCCCCCCC ARSLOAKOWGOSEX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- IFOGOHVJHKKYCT-UHFFFAOYSA-N hexyl heptanoate Chemical compound CCCCCCOC(=O)CCCCCC IFOGOHVJHKKYCT-UHFFFAOYSA-N 0.000 description 1
- NCDCLPBOMHPFCV-UHFFFAOYSA-N hexyl hexanoate Chemical compound CCCCCCOC(=O)CCCCC NCDCLPBOMHPFCV-UHFFFAOYSA-N 0.000 description 1
- 229940100463 hexyl laurate Drugs 0.000 description 1
- PBGWNXWNCSSXCO-UHFFFAOYSA-N hexyl octanoate Chemical compound CCCCCCCC(=O)OCCCCCC PBGWNXWNCSSXCO-UHFFFAOYSA-N 0.000 description 1
- 239000008173 hydrogenated soybean oil Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229940078565 isoamyl laurate Drugs 0.000 description 1
- 229940033357 isopropyl laurate Drugs 0.000 description 1
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
- AJAMRCUNWLZBDF-UHFFFAOYSA-N linoleic acid propyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCCC AJAMRCUNWLZBDF-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- ZYNDJIBBPLNPOW-KHPPLWFESA-N methyl erucate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC ZYNDJIBBPLNPOW-KHPPLWFESA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- PSXNDMJWRZYVTM-UHFFFAOYSA-N octanoic acid butyl ester Natural products CCCCCCCC(=O)OCCCC PSXNDMJWRZYVTM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CMNMHJVRZHGAAK-UHFFFAOYSA-N octyl hexanoate Chemical compound CCCCCCCCOC(=O)CCCCC CMNMHJVRZHGAAK-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RWSPHQOPNBVTAO-UTJQPWESSA-N pentyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCCOC(=O)CCCCCCC\C=C/C\C=C/CCCCC RWSPHQOPNBVTAO-UTJQPWESSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- SOAVQBSGNVIIEI-QXMHVHEDSA-N prop-2-enyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC=C SOAVQBSGNVIIEI-QXMHVHEDSA-N 0.000 description 1
- XEIOPEQGDSYOIH-MURFETPASA-N propan-2-yl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(C)C XEIOPEQGDSYOIH-MURFETPASA-N 0.000 description 1
- SQOVKJOWVZUDDC-AGRJPVHOSA-N propan-2-yl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC(C)C SQOVKJOWVZUDDC-AGRJPVHOSA-N 0.000 description 1
- LSVOEQJPCKJJLA-QXMHVHEDSA-N propan-2-yl (z)-docos-13-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC(C)C LSVOEQJPCKJJLA-QXMHVHEDSA-N 0.000 description 1
- SDYPTODXHIAHDF-ACQXMXPUSA-N propan-2-yl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(C)C SDYPTODXHIAHDF-ACQXMXPUSA-N 0.000 description 1
- DZFUWIPLAARMKN-UHFFFAOYSA-N propan-2-yl docosa-2,4,6,8,10,12-hexaenoate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OC(C)C DZFUWIPLAARMKN-UHFFFAOYSA-N 0.000 description 1
- SFPNSCZLRJDTGT-ACQXMXPUSA-N propyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCC SFPNSCZLRJDTGT-ACQXMXPUSA-N 0.000 description 1
- OVFMRFMJVFDSAA-UHFFFAOYSA-N propyl decanoate Chemical compound CCCCCCCCCC(=O)OCCC OVFMRFMJVFDSAA-UHFFFAOYSA-N 0.000 description 1
- VBUYNNWEOBJHCO-UHFFFAOYSA-N propyl docosa-2,4,6,8,10,12-hexaenoate Chemical compound C(CC)OC(C=CC=CC=CC=CC=CC=CCCCCCCCCC)=O VBUYNNWEOBJHCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AJAMRCUNWLZBDF-MURFETPASA-N propyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCC AJAMRCUNWLZBDF-MURFETPASA-N 0.000 description 1
- HCMSDHYNNJTLRW-UHFFFAOYSA-N propyl nonanoate Chemical compound CCCCCCCCC(=O)OCCC HCMSDHYNNJTLRW-UHFFFAOYSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- XKGDWZQXVZSXAO-UHFFFAOYSA-N ricinoleic acid methyl ester Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-UHFFFAOYSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- YCJYNBLLJHFIIW-MBABXGOBSA-N validoxylamine A Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)C[C@@H]1N[C@@H]1[C@H](O)[C@@H](O)[C@H](O)C(CO)=C1 YCJYNBLLJHFIIW-MBABXGOBSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
攪拌機、還流冷却管および温度計を備えた反応容器に、ブチルフェノール1,000部、92%パラホルムアルデヒド652部および水1,000部を仕込み、攪拌下に50℃まで昇温した。そして50℃において水酸化ナトリウム100部を仕込み、冷却しながら90℃まで徐々に昇温した後、2.5時間保温し、硫酸を滴下してpHを6付近に調整した。その後、キシレン200部を加え、ホルムアルデヒドなどを含んだ水層部を除去し、冷却してレゾール型ブチルフェノールの70%キシレン溶液を得た。
分水器付き還流冷却管および温度計を備えた反応容器に、ガムロジン1000部を仕込み、これを窒素雰囲気下に攪拌しながら220℃まで昇温して溶融し、製造例1で得たレゾール型ブチルフェノールの70%キシレン溶液143部(固形分100部)を220℃で1.5時間かけて系内へ滴下した。滴下終了し30分後、0.02MPaで10分間減圧後、内容物を冷却して樹脂aを得た。なお、該樹脂aの軟化点(JIS K0070)は101℃、酸価(JIS K5601−2−2)は147、重量平均分子量は450であった。また、樹脂aは、ジトリメチロールプロパンテトラアクリレート100重量部に対し、67重量部溶解できた。
分水器付き還流冷却管および温度計を備えた反応容器に、ガムロジン1000部を仕込み、これを窒素雰囲気下に攪拌しながら220℃まで昇温して溶融し、製造例1で得たレゾール型ブチルフェノールの70%キシレン溶液429部(固形分300部)を220℃で1.5時間かけて系内へ滴下した。滴下終了し30分後、0.02MPaで10分間減圧後、内容物を冷却して樹脂bを得た。なお、該樹脂bの軟化点は155℃、酸価は121、重量平均分子量は1,100であった。また、樹脂bは、ジトリメチロールプロパンテトラアクリレート100重量部に対し、28重量部溶解できた。
製造例2と同様の反応容器に、ガムロジン1000部を仕込み、これを窒素雰囲気下に攪拌しながら220℃まで昇温して溶融し、製造例1で得たレゾール型ブチルフェノールの70%キシレン溶液71部(固形分50部)を220℃で1.5時間かけて系内へ滴下した。滴下終了し30分後、0.02MPaで10分間減圧後、内容物を冷却して印刷インキ用樹脂cを得た。なお、該樹脂cの軟化点は77℃、酸価は152、重量平均分子量は370であった。また、樹脂cは、ジトリメチロールプロパンテトラアクリレート100重量部に対し、83重量部溶解できた。
実施例1と同様の反応容器に、ガムロジン1000部を仕込み、これを窒素雰囲気下に攪拌しながら220℃まで昇温して溶融し、製造例1で得たレゾール型ブチルフェノールの70%キシレン溶液571部(固形分400部)を220℃で1.5時間かけて系内へ滴下した。滴下終了し30分後、0.02MPaで10分間減圧後、内容物を冷却して印刷インキ用樹脂dを得た。なお、該樹脂dの軟化点は171℃、酸価は108、重量平均分子量は1,800であった。また、樹脂dは、ジトリメチロールプロパンテトラアクリレート100重量部に対し、2重量部溶解できた。
攪拌装置、冷却管、温度計および空気導入管を備えた反応装置に、樹脂aを20部、反応性希釈剤Bとしてジトリメチロールプロパンテトラアクリレート(商品名ビームセット730、荒川化学工業(株)製)80部、及びメトキノン(重合禁止剤)0.1部を仕込み、エアーバブリング下、90℃、1時間攪拌溶解した。60℃まで冷却後、該樹脂溶液に光重合開始剤としてイルガキュアー184(チバ・スペシャルティ・ケミカルズ社製登録商標)5部を混合、溶解し活性エネルギー線硬化性樹脂組成物を得た
樹脂aを樹脂b、cに変更した以外は実施例1と同様の操作を行い、活性エネルギー線硬化性樹脂組成物を得た。
実施例1と同様の反応容器に、樹脂dを20部、反応性希釈剤Bとしてジトリメチロールプロパンテトラアクリレート80部、及びメトキノン(重合禁止剤)0.1部を仕込み、エアーバブリング下、90℃、1時間攪拌したが、樹脂が溶け残り、活性エネルギー線硬化性樹脂組成物を得られなかった。
樹脂aをジアリルフタレート樹脂(ダイソー(株)製)に変更した以外は実施例1と同様の操作を行い、活性エネルギー線硬化性樹脂組成物を得た。
上記実施例及び比較例で得られた樹脂組成物に対し、以下の方法を用いて性能評価を行った。
実施例1および2ならびに比較例1および3で調製した樹脂組成物10部をキシレン20部に溶解し、ガラス試験管(内径18mm×高さ180mm×厚さ1.2mm、商品名PYREX(登録商標)TEST18、岩城硝子(株)製)に蒸留水7.5部を入れ、次に該キシレン溶液7.5部を入れて栓をした。これを上下に20回振とうし乳化させた後、静置して水層と有機層が完全に分離するまでの時間を測定した。水分離性と耐乳化性は相関があり、水分離性が良好であるほど、インキに適用した場合の耐乳化性が良好である。評価結果を表1に示す。
実施例1および2ならびに比較例1および3で調製した樹脂組成物をアート紙にバーコーター#14を用いて膜厚約20〜30μmで塗工し、次いで高圧水銀空冷ランプ(120W/cm、照射距離10cm)を使用し、ベルトスピード20m/分で紫外線照射し、数回通過させて表面硬化性および内部硬化性が良好になる通過回数で評価した。通過回数が多いほど硬化性良好である。なお表面硬化性が良好とは硬化皮膜が指触でべたつきがなくなる状態で、内部硬化性が良好とは硬化皮膜をキムワイプで強く擦っても硬化膜が剥がれない状態を言う。
Claims (10)
- ロジン類(a)およびレゾール型フェノール樹脂類(b)を反応させることにより得られる重量平均分子量400〜1,500のロジン変性フェノール樹脂(A)ならびに反応性希釈剤(B)を含有することを特徴とする活性エネルギー線硬化性樹脂組成物。
- ロジン変性フェノール樹脂(A)が、ジトリメチロールプロパンテトラアクリレート100重量部に対し、25重量部以上溶解することができるものである、請求項1記載の活性エネルギー線硬化性樹脂組成物。
- ロジン変性フェノール樹脂(A)の軟化点が80〜170℃である、請求項1または2記載の活性エネルギー線硬化性樹脂組成物。
- ロジン変性フェノール樹脂(A)の酸価が40以上である、請求項1〜3のいずれかに記載の活性エネルギー線硬化性樹脂組成物。
- ロジン変性フェノール樹脂(A)が、ロジン類(a)100重量部に対してレゾール型フェノール樹脂類(b)10〜40重量部を反応させて得られるものである、請求項1〜4のいずれかに記載の活性エネルギー線硬化性樹脂組成物。
- レゾール型フェノール樹脂類(b)が、アルキル基の炭素数が1〜20のアルキルフェノール類を用いて得られるものである、請求項1〜5のいずれかに記載の活性エネルギー線硬化性樹脂組成物。
- 反応性希釈剤(B)が、単官能または多官能の(メタ)アクリルモノマーである請求項1〜6のいずれかに記載の活性エネルギー線硬化性樹脂組成物。
- さらに光重合開始剤を含有してなる請求項1〜7のいずれかに記載の活性エネルギー線硬化性樹脂組成物。
- さらに植物油または脂肪酸エステルを含有してなる請求項1〜8のいずれかに記載の活性エネルギー線硬化性樹脂組成物。
- 請求項1〜9のいずれかに記載の活性エネルギー線硬化性樹脂組成物を含有する印刷インキ。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007052131A JP5354242B2 (ja) | 2007-03-02 | 2007-03-02 | 活性エネルギー線硬化性樹脂組成物および印刷インキ |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007052131A JP5354242B2 (ja) | 2007-03-02 | 2007-03-02 | 活性エネルギー線硬化性樹脂組成物および印刷インキ |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2008214441A JP2008214441A (ja) | 2008-09-18 |
JP5354242B2 true JP5354242B2 (ja) | 2013-11-27 |
Family
ID=39834885
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007052131A Active JP5354242B2 (ja) | 2007-03-02 | 2007-03-02 | 活性エネルギー線硬化性樹脂組成物および印刷インキ |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5354242B2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6597688B2 (ja) * | 2017-03-23 | 2019-10-30 | 東洋インキScホールディングス株式会社 | 活性エネルギー線硬化型樹脂組成物、インキおよび印刷物 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3282414B2 (ja) * | 1994-11-16 | 2002-05-13 | 荒川化学工業株式会社 | 活性エネルギー線硬化性樹脂組成物 |
JP3658298B2 (ja) * | 2000-08-24 | 2005-06-08 | 大日本インキ化学工業株式会社 | 印刷インキ組成物 |
JP3876643B2 (ja) * | 2001-05-07 | 2007-02-07 | 東洋インキ製造株式会社 | 硬化性被覆組成物、硬化性インキ、その印刷方法およびその印刷物 |
JP3940951B2 (ja) * | 2003-04-25 | 2007-07-04 | 荒川化学工業株式会社 | 活性エネルギー線硬化性樹脂組成物、硬化物、硬化フィルム、コーティング剤および封止剤 |
JP2005154704A (ja) * | 2003-11-21 | 2005-06-16 | Hitachi Kasei Polymer Co Ltd | 印刷インキ用樹脂ワニスの製造方法 |
-
2007
- 2007-03-02 JP JP2007052131A patent/JP5354242B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2008214441A (ja) | 2008-09-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7863485B2 (en) | Additive and vehicle for inks, paints, coatings and adhesives | |
JP5582419B2 (ja) | ロジン変性フェノール樹脂、その製造方法および印刷インキ | |
JP4511822B2 (ja) | 活性エネルギー線硬化性乾式平版印刷インキ組成物、印刷方法およびその印刷物 | |
US9150742B2 (en) | Linear polyester resins and improved lithographic inks | |
JP2008274150A (ja) | ロジン変性フェノール樹脂およびオフセット印刷用ロジン変性フェノール樹脂 | |
JP6548018B2 (ja) | 変性ロジンエステル樹脂、活性エネルギー線硬化型樹脂組成物及び硬化物 | |
JP2004359767A (ja) | 活性エネルギー線硬化性乾式平版印刷インキ組成物、印刷方法およびその印刷物 | |
JP7163844B2 (ja) | 活性エネルギー線硬化型平版印刷インキ用ロジン変性ポリエステル樹脂、活性エネルギー線硬化型平版印刷インキ、および印刷物 | |
JP5354242B2 (ja) | 活性エネルギー線硬化性樹脂組成物および印刷インキ | |
WO2020012965A1 (ja) | 活性エネルギー線硬化型オフセット印刷用インキ組成物、及びそれを用いた印刷物の製造方法 | |
TWI752104B (zh) | 能量可固化水性組成物及使用其製備經塗佈的基材或物件之方法 | |
JP2014015572A (ja) | 活性エネルギー線硬化型インキおよび印刷物 | |
JP2007056186A (ja) | 硬化性組成物、それを使用した活性エネルギー線硬化性印刷インキ及びその印刷物 | |
JP7309421B2 (ja) | 活性エネルギー線硬化型ニス組成物及びその製造方法、並びにそれを用いた印刷物の製造方法 | |
US11932768B2 (en) | Active energy ray-curable ink composition, method for producing same, and method for producing printed matter in which same is used | |
JP6237410B2 (ja) | 活性エネルギー線硬化型インキおよび印刷物 | |
JP2011184660A (ja) | ロジン変性フェノール樹脂、その製造方法および印刷インキ | |
WO2014041890A1 (ja) | ロジン変性フェノール樹脂、インキ用ワニス組成物及び印刷インキ | |
JP2007056185A (ja) | 硬化性組成物、それを使用した活性エネルギー線硬化性印刷インキ及びその印刷物 | |
JP2006016508A (ja) | アクリルモノマーまたはそれを含む活性エネルギー線硬化性組成物およびその印刷物。 | |
TWI827588B (zh) | 輻射固化組成物 | |
JP2006016510A (ja) | アクリルオリゴマーまたはそれを含む活性エネルギー線硬化性組成物およびその印刷物。 | |
JP2006016509A (ja) | アクリルオリゴマーまたはそれを含む活性エネルギー線硬化性組成物およびその印刷物。 | |
KR20190128641A (ko) | 부드러운 감촉 코팅의 형성 방법 | |
JP2006008844A (ja) | 印刷インキ組成物、およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100107 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110518 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121015 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121106 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130801 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130814 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5354242 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |