JPH0545431B2 - - Google Patents
Info
- Publication number
- JPH0545431B2 JPH0545431B2 JP59022622A JP2262284A JPH0545431B2 JP H0545431 B2 JPH0545431 B2 JP H0545431B2 JP 59022622 A JP59022622 A JP 59022622A JP 2262284 A JP2262284 A JP 2262284A JP H0545431 B2 JPH0545431 B2 JP H0545431B2
- Authority
- JP
- Japan
- Prior art keywords
- electron
- accepting compound
- tert
- methyl
- diethylaminofluorane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000000463 material Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000123 paper Substances 0.000 description 16
- 239000000975 dye Substances 0.000 description 14
- -1 benzyl 2,4-dihydroxybenzoic acid ester Chemical class 0.000 description 12
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 229940114055 beta-resorcylic acid Drugs 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 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 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002612 dispersion medium Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229940043267 rhodamine b Drugs 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 150000004897 thiazines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 2
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- SLHHISZGJKXGLF-UHFFFAOYSA-N (4-chlorophenyl) ethaneperoxoate;4-phenylphenol Chemical compound CC(=O)OOC1=CC=C(Cl)C=C1.C1=CC(O)=CC=C1C1=CC=CC=C1 SLHHISZGJKXGLF-UHFFFAOYSA-N 0.000 description 1
- LSNOYMODFMFKEG-UHFFFAOYSA-N (4-chlorophenyl)methyl 2,4-dihydroxybenzoate Chemical compound OC1=CC(O)=CC=C1C(=O)OCC1=CC=C(Cl)C=C1 LSNOYMODFMFKEG-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- YLOGJPLTYYDQCN-UHFFFAOYSA-N 1,3-didodecylurea Chemical compound CCCCCCCCCCCCNC(=O)NCCCCCCCCCCCC YLOGJPLTYYDQCN-UHFFFAOYSA-N 0.000 description 1
- JWSWULLEVAMIJK-UHFFFAOYSA-N 1-phenylmethoxynaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1=CC=CC=C1 JWSWULLEVAMIJK-UHFFFAOYSA-N 0.000 description 1
- DXYZIGZCEVJFIX-UHFFFAOYSA-N 2'-(dibenzylamino)-6'-(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC=C3N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DXYZIGZCEVJFIX-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- DYWBYCYREANRBJ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methoxy]naphthalene Chemical compound C1=CC(Cl)=CC=C1COC1=CC=C(C=CC=C2)C2=C1 DYWBYCYREANRBJ-UHFFFAOYSA-N 0.000 description 1
- WLTCCDHHWYAMCG-UHFFFAOYSA-N 2-phenylmethoxynaphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1OCC1=CC=CC=C1 WLTCCDHHWYAMCG-UHFFFAOYSA-N 0.000 description 1
- YFHKLSPMRRWLKI-UHFFFAOYSA-N 2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-6-methylphenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 YFHKLSPMRRWLKI-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- IHHGGBSHYHADSR-UHFFFAOYSA-N 2-tert-butyl-4-[(2-methylpropan-2-yl)oxy]phenol Chemical compound CC(C)(C)OC1=CC=C(O)C(C(C)(C)C)=C1 IHHGGBSHYHADSR-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 description 1
- ABJAMKKUHBSXDS-UHFFFAOYSA-N 3,3-bis(6-amino-1,4-dimethylcyclohexa-2,4-dien-1-yl)-2-benzofuran-1-one Chemical compound C1=CC(C)=CC(N)C1(C)C1(C2(C)C(C=C(C)C=C2)N)C2=CC=CC=C2C(=O)O1 ABJAMKKUHBSXDS-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- FFXPOZNUNSROLU-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-3-(1,3-dimethyl-2h-indol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC(N(C)C)=CC=C1C1(C2(C)C3=CC=CC=C3N(C)C2)C2=CC=CC=C2C(=O)O1 FFXPOZNUNSROLU-UHFFFAOYSA-N 0.000 description 1
- ZKUWHPNJONEJEE-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-3-(2-methyl-1h-indol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C3=CC=CC=C3NC=2C)C2=CC=CC=C2C(=O)O1 ZKUWHPNJONEJEE-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
- UGAZGXGAIAGBMP-UHFFFAOYSA-N 6-tert-butyl-2,2-dimethyl-3h-1-benzofuran-5-ol Chemical compound C1=C(O)C(C(C)(C)C)=CC2=C1CC(C)(C)O2 UGAZGXGAIAGBMP-UHFFFAOYSA-N 0.000 description 1
- IRVXJSBATNRECV-UHFFFAOYSA-N 7-tert-butyl-2,2-dimethyl-4-propan-2-yl-3,4-dihydrochromen-6-ol Chemical compound CC(C)(C)C1=C(O)C=C2C(C(C)C)CC(C)(C)OC2=C1 IRVXJSBATNRECV-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 1
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- LZKPUVULVAMJGR-UHFFFAOYSA-N acetic acid;benzene-1,4-diol Chemical compound CC(O)=O.OC1=CC=C(O)C=C1 LZKPUVULVAMJGR-UHFFFAOYSA-N 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- NENFFQGUGLZPPY-UHFFFAOYSA-N benzyl 2,4-dihydroxybenzoate Chemical compound OC1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 NENFFQGUGLZPPY-UHFFFAOYSA-N 0.000 description 1
- BPLKDVGMXNZCQO-UHFFFAOYSA-N benzyl 4-phenylmethoxybenzoate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(=O)OCC1=CC=CC=C1 BPLKDVGMXNZCQO-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- NKOHYPZTBAEGGO-UHFFFAOYSA-N hexadecylurea Chemical compound CCCCCCCCCCCCCCCCNC(N)=O NKOHYPZTBAEGGO-UHFFFAOYSA-N 0.000 description 1
- HBMCQTHGYMTCOF-UHFFFAOYSA-N hydroquinone monoacetate Natural products CC(=O)OC1=CC=C(O)C=C1 HBMCQTHGYMTCOF-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UMYIKBNPUAUDNR-UHFFFAOYSA-N n-(4-ethoxyphenyl)tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NC1=CC=C(OCC)C=C1 UMYIKBNPUAUDNR-UHFFFAOYSA-N 0.000 description 1
- OFXYUUZFRJEEKP-UHFFFAOYSA-N n-(4-methoxyphenyl)tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NC1=CC=C(OC)C=C1 OFXYUUZFRJEEKP-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
- ZOLJFBQEKSZVCB-UHFFFAOYSA-N n-phenyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1 ZOLJFBQEKSZVCB-UHFFFAOYSA-N 0.000 description 1
- GBXJELALHBHGGN-UHFFFAOYSA-N naphthalen-1-yl 2-phenoxyacetate Chemical compound C=1C=CC2=CC=CC=C2C=1OC(=O)COC1=CC=CC=C1 GBXJELALHBHGGN-UHFFFAOYSA-N 0.000 description 1
- DWJIJRSTYFPKGD-UHFFFAOYSA-N naphthalen-2-yl benzoate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=O)C1=CC=CC=C1 DWJIJRSTYFPKGD-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- QHDYIMWKSCJTIM-UHFFFAOYSA-N phenyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 QHDYIMWKSCJTIM-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
<発明の利用分野>
本発明は記録材料に関するものである。
本発明に係る記録材料は電子供与性無色染料と
電子受容性化合物の発色反応を利用したものであ
り、特に、新規な電子受容性化合物を用いた記録
材料に関する。
本発明に係る電子受容性化合物は、特に、感圧
記録材料および感熱記録材料用の電子受容性化合
物として極めて有用な化合物であり、また通電感
熱記録シート、感光性記録シート、超音波記録シ
ート、電子線記録シート、静電記録シート、感光
性印刷版材、捺印材料、タイプリボン、ボールペ
ンインキ、クレヨンなどにも応用できる化合物で
ある。
<従来技術>
種々のフエノール化合物を感圧記録材料または
感熱記録材料の電子受容性化合物として使用する
ことは、特公昭40−9309号、特公昭45−14039号、
特公昭51−29830号等に開示されているが、これ
らのフエノール化合物は、必ずしも満足できる電
子受容性化合物とはいえない。すなわち、電子供
与性無色染料と組合わせ使用したときの発色濃度
が十分でない。
また、特開昭58−209590号に開示されている
2,4、ジヒドロキシ安息香酸ベンジルエステル
を感熱記録材料に使用した場合は、記録材料の耐
湿熱性、カブリの発生等の点で不十分である。
<発明の目的>
従つて本発明の目的は電子供与性無色染料と組
合わせ使用したときの発色濃度が十分な記録材料
を提供することである。
<発明の構成>
本発明の目的は電子供与性無色染料と電子受容
性化合物として下記一般式で表わされる化合物を
使用することを特徴とする記録材料により達成さ
れた。
上式において、Rは炭素数2〜5のアルキル
基、炭素数1〜5のアルコキシ基、ハロゲン原
子、またはシアノ基を表わす。
上記一般式においてRの置換位置はどこでもよ
いが
<Field of Application of the Invention> The present invention relates to recording materials. The recording material according to the present invention utilizes a color-forming reaction between an electron-donating colorless dye and an electron-accepting compound, and particularly relates to a recording material using a novel electron-accepting compound. The electron-accepting compound according to the present invention is particularly useful as an electron-accepting compound for pressure-sensitive recording materials and heat-sensitive recording materials. It is a compound that can be applied to electron beam recording sheets, electrostatic recording sheets, photosensitive printing plates, stamping materials, type ribbons, ballpoint pen inks, crayons, etc. <Prior art> The use of various phenol compounds as electron-accepting compounds for pressure-sensitive recording materials or heat-sensitive recording materials is disclosed in Japanese Patent Publication No. 40-9309, Japanese Patent Publication No. 45-14039,
Although disclosed in Japanese Patent Publication No. 51-29830, etc., these phenol compounds cannot necessarily be said to be satisfactory electron-accepting compounds. That is, when used in combination with an electron-donating colorless dye, the color density is not sufficient. Furthermore, when the benzyl 2,4-dihydroxybenzoic acid ester disclosed in JP-A No. 58-209590 is used in a heat-sensitive recording material, the recording material is insufficient in terms of moisture and heat resistance, fogging, etc. . <Object of the Invention> Accordingly, an object of the present invention is to provide a recording material that has sufficient color density when used in combination with an electron-donating colorless dye. <Structure of the Invention> The object of the present invention has been achieved by a recording material characterized in that it uses an electron-donating colorless dye and a compound represented by the following general formula as an electron-accepting compound. In the above formula, R represents an alkyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogen atom, or a cyano group. In the above general formula, R may be substituted at any position.
【式】基に対してオルト
またはパラ位が好ましく、特にパラ位が好まし
い。
上記一般式においてRで表わされる置換基のう
ち、炭素数2〜5のアルキル基、炭素原子数1〜
5のアルコキシ基、塩素原子、臭素原子およびシ
アノ基が好ましく、特に炭素数2〜3のアルキル
基、炭素原子数1〜3のアルコキシ基および塩素
原子が好ましい。
本発明に係る電子受容性化合物を感熱記録材料
用の電子受容性化合物として用いる時には、50℃
以上の融点を有するものが好ましく、特に70℃〜
150℃の融点を有するものが好ましい。
本発明に係る電子受容性化合物の特徴として以
下のことがあげられる。
(i) 電子供子性無色染料との組合わせにより、高
濃度の発色像を与える。
(ii) 水溶性が少ない。
(iii) 昇華性がなく安定である。
(iv) 合成が容易であり、高収率で高純度のものが
得られる。また原材料も安価である。
次に本発明の電子受容性化合物の具体例を示す
が、本発明はこれらに限定されるものではない。
(1) 2,4−ジヒドロキシ安息香酸P−イソプロ
ビルベンジルエステル
(2) 2,4−ジヒドロキシ安息香酸P−メトキシ
ベンジルエステル
(3) 2,4−ジヒドロキシ安息香酸P−クロロベ
ンジルエステル
(4) 2,4−ジヒドロキシ安息香酸m−クロロベ
ンジルエステル
(5) 2,4−ジヒドロキシ安息香酸O−クロロベ
ンジルエステル
等。
これらは単独もしくは混合または他の電子受容
性化合物(例えば、ビスフエノールA、4−ヒド
ロキシ安息香酸ベンジルエステル等)と混合して
用いられる。
本発明に使用する電子供与性無色染料として
は、トリアリールメタン系化合物、ジフエニルメ
タン系化合物、キサンテン系化合物、チアジン系
化合物、スピロピラン系化合物などが用いられて
いる。これらの一部を例示すれば、トリアリール
メタン系化合物として、3,3−ビス(p−ジメ
チルアミノフエニル)−6−ジメチルアミノフタ
リド(即ちクリスタルバイオレツトラクトン)、
3,3−ビス(p−ジメチルアミノフエニル)フ
タリド、3−(p−ジメチルアミノフエニル)−3
−(1,3−ジメチルインドール−3−イル)フ
タリド、3−(p−ジメチルアミノフエニル)−3
−(2−メチルインドール−3−イル)フタリド
等があり、ジフエニルメタン系化合物としては、
4,4′−ビス−ジメチルアミノベンズヒドリンベ
ンジルエーテル、N−ハロフエニル−ロイコオー
ラミン、N−2,4,5−トリクロロフエニルロ
イコオーラミン等があり、キサンテン系化合物と
しては、ローダミン−B−アニリノラクタム、ロ
ーダミン(p−ニトロアニリノ)ラクタム、ロー
ダミンB(p−クロロアニリノ)ラクタム、2−
ジベンジルアミノ−6−ジエチルアミノフルオラ
ン、2−アニリノ−6−ジエチルアミノフルオラ
ン、2−アニリノ−3−メチル−6−ジエチルア
ミノフルオラン、2−アニリノ−3−メチル−6
−N−シクロヘキシル−N−メチルアミノフルオ
ラン、2−アニリノ−3−メチル−6−N−エチ
ル−N−イソアミルアミノフルオラン、2−o−
クロロアニリノ−6−ジエチルアミノフルオラ
ン、2−m−クロロアニリノ−6−ジエチルアミ
ノフルオラン、2−(3,4−ジクロロアニリノ)
−6−ジエチルアミノフルオラン、2−オクチル
アミノ−6−ジエチルアミノフルオラン、2−ジ
ヘキシルアミノ−6−ジエチルアミノフルオラ
ン、2−m−トリクロロメチルアニリノ−6−ジ
エチルアミノフルオラン、2−ブチルアミノ−3
−クロロ−6−ジエチルアミノフルオラン、2−
エトキシエチルアミノ−3−クロロ−6−ジエチ
ルアミノフルオラン、2−アニリノ−3−クロロ
−6−ジエチルアミノフルオラン、2−ジフエニ
ルアミノ−6−ジエチルアミノフルオラン、2−
アニリノ−3−メチル−6−ジフエニルアミノフ
ルオラン、2−アニリノ−3−メチル−5−クロ
ロ−6−ジエチルアミノフルオラン、2−アニリ
ノ−3−メチル−6−ジエチルアミノ−7−メチ
ルフルオラン、2−アニリノ−3−メトキシ6−
ジブチルアミノフルオラン、2−o−クロロアニ
リノ−6−ジブチルアミノフルオラン、2−p−
クロロアニリノ−3−エトキシ−6−ジエチルア
ミノフルオラン、2−フエニル−6−ジエチルア
ミノフルオラン等がありチアジン系化合物として
は、ベンゾイルロイコメチレンブルー、p−ニト
ロベンジルロイコメチレンブルー等があり、スピ
ロ系化合物としては、3−メチル−スピロ−ジナ
フトピラン、3−エチル−スピロ−ジナフトピラ
ン、3,3′−ジクロロ−スピロ−ジナフトビラ
ン、3−ベンジルスピロ−ジナフトピラン、3−
メチル−ナフト−(3−メトキシ−ベンゾ)−スピ
ロピラン、3−プロピル−スピロ−ジベンゾピラ
ン等がある。これらは単独もしくは混合して用い
られる。
次に本発明に係る記録材料の具体的製造法につ
いて述べる。
本発明に係る感圧複写紙は米国特許第2505470
号、同2505471号、同2505489号、同2548366号、
同2712507号、同2730456号、同第2730457号、同
第3418250号などの先行特許などに記載されてい
る様に種々の形態をとりうる。最も一般的には本
発明に係る電子供与性無色染料および電子受容性
化合物を別々に含有する少なくとも一対のシート
から成る。即ち電子供与性無色染料を単独又は混
合して、溶媒(アルキル化ナフタレン、アルキル
化ジフエニル、アルキル化ジフエニルメタン、ア
ルキル化ターフエニルなどの合成油:木綿油、ヒ
マシ油などの植物油:動物油:鉱物油或いはこれ
らの混合物など)に溶解し、これをバインダー中
に分散するか、又はマイクロカプセル中に含有さ
せた後、紙、プラスチツクシート、樹脂コーテツ
ド紙などの支持体に塗布することにより発色剤シ
ートを、また電子受容性化合物を単独又は混合し
てあるいは他の電子受容性化合物と共に、スチレ
ンブタジエンラテツクス、ポリビニールアルコー
ルの如きバインダー中に分散させ、紙、プラスチ
ツクシート、樹脂コーテツド紙などの支持体に塗
布することにより顕色剤シートを得る。
電子供与性無色染料および電子受容性化合物の
使用量は所望の塗布厚、感圧複写紙の形態、カプ
セルの製法、その他の条件によるのでその条件に
応じて適宜選べばよい。当業者がこの使用量を決
定することは容易である。
カプセルの製造方法については、米国特許
2800457号、同2800458号に記載された親水性コロ
イドゾルのコアセルベーシヨンを利用した方法、
英国特許867797号、同950443号、同989264号、同
1091076号などに記載された界面重合法などがあ
る。
感熱記録材料は、バインダーを溶媒または分散
媒に溶解または分散した液に、電子供与性無色染
料、本発明に係る電子受容性化合物、および必要
であれば熱可融性物質を十分に細かく粉砕混合
し、さらに、カオリン、焼成カオリン、タルク、
ろう石、ケイソウ土、炭酸カルシウム、水酸化ア
ルミニウム、水酸化マグネシウム、炭酸マグネシ
ウム、酸化チタン、炭酸バリウム、尿素−ホルマ
リンフイラー、セルロースフイラー等の吸油性顔
料を加えて塗液を作用する。これに必要に応じて
パラフインワツクスエマルジヨン、ラテツクス系
バインダー、感度向上剤、金属石けん、酸化防止
剤、紫外線吸収剤、画像保存性向上剤などを添加
することができる。
塗液は、紙、プラスチツクシート、樹脂コーテ
ツド紙などの支持体に塗布乾燥される。塗液を調
製する際、全成分をはじめから同時に混合して粉
砕してもよいし適当な組みあわせにして別々に粉
砕分散の後、混合してもよい。
また、塗布液は、支持体中に抄き込ませてもよ
い。
感熱記録材料を構成する各成分の量は、電子供
与性無色染料1〜2重量部、電子受容性化合物1
〜6重量部、熱可融性物質0〜30重量部、顔料0
〜15重量部、バインダー1〜15重量部及び分散媒
(溶媒)20〜300重量部である。
電子供与性無色染料は一種または複数混合して
用いても良い。分散媒(溶媒)としては、水が最
も望ましい。
次に本発明に用いられるバインダーを例示する
と、スチレン−ブタジエンのコポリマー、アルキ
ツド樹脂、アクリルアミドコポリマー、塩化ビニ
ル−酢酸ビニルのコポリマー、スチレン−無水マ
レイン酸のコポリマー、合成ゴム、アラビヤゴ
ム、ポリビニルアルコール、ヒドロキシエチルセ
ルロース等を挙げることができる。
特に分散媒(溶媒)との関係上アラビヤゴム、
ポリビニルアルコール、ヒドロキシメチルセルロ
ース、カルボキシメチルセルロース等の水溶性バ
インダーが望ましい。
熱可融性物質としては、必要によりエルカ酸、
ステアリン酸、ベヘン酸、パルミチン酸、ステア
リン酸アミド、ベヘン酸アミド、ステアリン酸ア
ニリド、ステアリン酸トルイジド、N−ミリスト
イル−p−アニシジン、N−ミリストイル−p−
フエネチジン、1−メトキシカルボニル−4−N
−ステアリルカルバモイルベンゼン、N−オクタ
デシルウレア、N−ヘキサデシルウレア、N,
N′−ジドデシルウレア、フエニルカルバモイル
オキシドデカン、p−t−ブチルフエノールフエ
ノキシアセテート、p−フエニルフエノール−p
−クロロフエノキシアセテート、4,4′−イソプ
ロピリデンビスメトキシベンゼン、β−フエニル
エチル−p−フエニルフエニルエーテル、2−p
−クロロベンジルオキシナフタレン、2−ベンジ
ルオキシナフタレン、1−ベンジルオキシナフタ
レン、2−フエノキシアセチルオキシナフタレ
ン、フタル酸ジフエニルエステル、1−ヒドロキ
シ−2−ナフトエ酸フエニルエステル、2−ベン
ゾイルオキシナフタレン、p−ベンジルオキシ安
息香酸ベンジルエステル、ハイドロキノンアセテ
ート等が用いられる。
これらの物質は、常温では無色の固体であり、
複写用加熱温度に適する温度、即ち70〜160℃付
近でシヤープな融点を有する物質である。
ワツクス類としては、パラフインワツクス、カ
ウナバロウワツクス、マイクロクリスタリンワツ
クス、ポリエチレンワツクスの他、高級脂肪酸ア
ミド例えば、ステアリン酸アミド、エチレンビス
ステアロアミド、高級脂肪酸エステル等があげら
れる。
金属石ケンとしては、高級脂肪酸多価金属塩例
えば、ステアリン酸亜鉛、ステアリン酸アルミニ
ウム、ステアリン酸カルシウム、オレイン酸亜鉛
等があげられる。
画像保存性向上剤としては少なくとも2または
6位のうち1個以上がアルキル基で置換されたフ
エノールあるいはその誘導体があげられ、その中
でも2または6位のうち1個以上がtert−ブチル
基で置換されたフエノールあるいはその誘導体が
好ましい。また、分子中にフエノール基を複数個
有するものが好ましく、特に2ないし3個のフエ
ノール基を有するものが好ましい。これらの化合
物の具体例をあげると、
ビス−〔3,3−ビス−(4′−ヒドロキシ−3′−
tert−ブチルフエニル)−ブタノイシクアシド〕
グリコールエステル、
ビス−〔3,3−ビス−(4′−ヒドロキシ−3′,
4′−ジtert−ブチルフエニル)ブタノイツクアシ
ド〕グリコールエステル、
ビス〔3,3−ビス−(2′−メチル−4′−ヒド
ロキシ−5′−tert−ブチルフエニル)−ブタノイツ
クアシド〕グリコールエステル、
1,1,3−トリス(2−メチル−4−ヒドロ
キシ−5−tert−ブチルフエニル)ブタン、
4,4′−チオビス(3−メチル−6−tert−ブ
チルフエノール)、
4,4′−チオビス(2−メチル−6−tert−ブ
チルフエノール)、
2,2′−チオビス(4−メチル−6−tert−ブ
チルフエノール)、
2,2′−メチレンビス(4−メチル−6−tert
−ブチルフエノール)、
2,2′−メチレンビス(4−エチル−6−tert
−ブチルフエノール)、
4,4′−ブチリデンビス(3−メチル−6−
tert−ブチルフエノール)、
4,4′−メチレンビス(2,6−ジtert−ブチ
ルフエノール)、
2−tert−ブチル−4−tert−ブトキシフエノ
ール、
2,2−ジメチル−4−イソプロピル−7−
tert−ブチル−6−クロマノール、
2,2−ジメチル−6−t−ブチル−5−ベン
ゾフラノール、
4〔〔4,6−ビス(tertブチルチオ)−s−ト
リアジン−2−イル〕アミノ〕2・6−ジ−tert
−ブチルフエノール等がある。
これらの化合物の使用量は、電子受容性化合物
に対して5〜200重量パーセント、好ましくは20
〜100重量パーセントである。
以下実施例を示すが、本発明は、この実施例の
みに限定されるものではない。
実施例
電子供与性無色染料である2−アニリノ−3−
クロロ−6−ジエチルアミノフルオラン5gを5
%ポリビニルアルコール(ケン価度99%、重合度
1000)水溶液50gとともにボールミルで一昼夜分
散した。一方、同様に、電子受容性化合物である
2,4−ジヒドロキシ安息香酸−p−クロロベン
ジルエステル(融点138〜140℃)10gを5%ポリ
ビニルアルコール水溶液100gとともにボールミ
ルで一昼夜分散し、これら2種の分散液を混合し
た後カオリン(ジヨージアカオリン)20gを添加
してよく分散させ、さらにパラフインワツクスエ
マルジヨン50%分散液(中京油脂セロゾール
#428)5gを加えて塗液とした。
塗液は50g/m2の坪量を有する原紙上に固形分
塗布量として6g/m2となるように塗布し、60℃
で1分間乾燥して塗布紙を得た。
塗布紙をフアクシミリにより加熱エネルギー40
mJ/mm2で加熱発色させると黒色の印像が得られ
た。発色濃度は0.93であつた。
比較例 1
実施例の電子受容性化合物の代わりに、電子受
容性化合物として、2,2−ビス(4−ヒドロキ
シフエニル)プロパン10gを用いて、実施例同様
にして塗布紙を得た。
塗布紙をフアクシミリにより加熱エネルギー40
mJ/mm2で加熱発色させたところ発色濃度は0.58
であつた。
実施例と比較例1を比較すれば、本発明の電子
受容性化合物の発色性が極めて高いことが明らか
である。
比較例 2
実施例の電子受容性化合物の代わりに、電子受
容性化合物として、2,4−ジヒドロキシ安息香
酸ベンジルエステル10gを用いて、実施例同様に
して塗布紙を得た。
塗布紙をフアクシミリにより加熱エネルギー40
mJ/mm2で加熱発色させたところ発色濃度は1.05
であつた。
またこの塗布紙を、40℃、90%RH中に24時間
放置した後の塗布紙の濃度は0.21であつた。
これに対して、本発明の電子受容性化合物を使
用した記録紙は、耐湿熱性に秀れるものである。The ortho or para position relative to the group [Formula] is preferred, and the para position is particularly preferred. Among the substituents represented by R in the above general formula, alkyl groups having 2 to 5 carbon atoms, 1 to 5 carbon atoms,
5 alkoxy groups, chlorine atoms, bromine atoms, and cyano groups are preferred, and alkyl groups having 2 to 3 carbon atoms, alkoxy groups having 1 to 3 carbon atoms, and chlorine atoms are particularly preferred. When the electron-accepting compound according to the present invention is used as an electron-accepting compound for heat-sensitive recording materials, the temperature is 50°C.
It is preferable to have a melting point of 70℃ or higher, especially 70℃~
Those having a melting point of 150°C are preferred. The characteristics of the electron-accepting compound according to the present invention include the following. (i) When combined with an electronic colorless dye, it provides a highly concentrated colored image. (ii) Poor water solubility. (iii) Stable without sublimation. (iv) It is easy to synthesize and can be obtained in high yield and purity. The raw materials are also cheap. Next, specific examples of the electron-accepting compound of the present invention will be shown, but the present invention is not limited thereto. (1) 2,4-dihydroxybenzoic acid P-isopropylbenzyl ester (2) 2,4-dihydroxybenzoic acid P-methoxybenzyl ester (3) 2,4-dihydroxybenzoic acid P-chlorobenzyl ester (4) 2 , 4-dihydroxybenzoic acid m-chlorobenzyl ester (5) 2,4-dihydroxybenzoic acid O-chlorobenzyl ester, etc. These may be used alone, in combination, or in combination with other electron-accepting compounds (eg, bisphenol A, 4-hydroxybenzoic acid benzyl ester, etc.). As the electron-donating colorless dye used in the present invention, triarylmethane compounds, diphenylmethane compounds, xanthene compounds, thiazine compounds, spiropyran compounds, etc. are used. To illustrate some of these, triarylmethane compounds include 3,3-bis(p-dimethylaminophenyl)-6-dimethylaminophthalide (i.e., crystal violet lactone);
3,3-bis(p-dimethylaminophenyl)phthalide, 3-(p-dimethylaminophenyl)-3
-(1,3-dimethylindol-3-yl)phthalide, 3-(p-dimethylaminophenyl)-3
-(2-methylindol-3-yl)phthalide, etc. Diphenylmethane compounds include:
There are 4,4'-bis-dimethylaminobenzhydrin benzyl ether, N-halophenyl-leucoauramine, N-2,4,5-trichlorophenylleucoauramine, and xanthene compounds include rhodamine-B. -anilinolactam, rhodamine (p-nitroanilino)lactam, rhodamine B (p-chloroanilino)lactam, 2-
Dibenzylamino-6-diethylaminofluorane, 2-anilino-6-diethylaminofluorane, 2-anilino-3-methyl-6-diethylaminofluorane, 2-anilino-3-methyl-6
-N-cyclohexyl-N-methylaminofluorane, 2-anilino-3-methyl-6-N-ethyl-N-isoamylaminofluorane, 2-o-
Chloroanilino-6-diethylaminofluorane, 2-m-chloroanilino-6-diethylaminofluorane, 2-(3,4-dichloroanilino)
-6-diethylaminofluorane, 2-octylamino-6-diethylaminofluorane, 2-dihexylamino-6-diethylaminofluorane, 2-m-trichloromethylanilino-6-diethylaminofluorane, 2-butylamino-3
-Chloro-6-diethylaminofluorane, 2-
Ethoxyethylamino-3-chloro-6-diethylaminofluorane, 2-anilino-3-chloro-6-diethylaminofluorane, 2-diphenylamino-6-diethylaminofluorane, 2-
Anilino-3-methyl-6-diphenylaminofluoran, 2-anilino-3-methyl-5-chloro-6-diethylaminofluoran, 2-anilino-3-methyl-6-diethylamino-7-methylfluoran, 2-anilino-3-methoxy6-
Dibutylaminofluorane, 2-o-chloroanilino-6-dibutylaminofluorane, 2-p-
Chloranilino-3-ethoxy-6-diethylaminofluoran, 2-phenyl-6-diethylaminofluoran, etc.; thiazine compounds include benzoylleucomethylene blue, p-nitrobenzylleucomethylene blue, etc.; spiro compounds include: 3-Methyl-spiro-dinaphthopyran, 3-ethyl-spiro-dinaphthopyran, 3,3'-dichloro-spiro-dinaphthopyran, 3-benzylspiro-dinaphthopyran, 3-
Examples include methyl-naphtho-(3-methoxy-benzo)-spiropyran and 3-propyl-spiro-dibenzopyran. These may be used alone or in combination. Next, a specific method for manufacturing the recording material according to the present invention will be described. The pressure-sensitive copying paper according to the present invention is disclosed in U.S. Patent No. 2505470.
No. 2505471, No. 2505489, No. 2548366,
It can take various forms as described in prior patents such as No. 2712507, No. 2730456, No. 2730457, and No. 3418250. Most commonly, it will consist of at least one pair of sheets separately containing an electron-donating colorless dye and an electron-accepting compound according to the invention. That is, electron-donating colorless dyes may be used alone or in combination, and a solvent (synthetic oils such as alkylated naphthalene, alkylated diphenyl, alkylated diphenylmethane, and alkylated terphenyl; vegetable oils such as cotton oil and castor oil; animal oil; mineral oil; or The color former sheet can also be prepared by dissolving the color former in a mixture of the color former (e.g., a mixture of An electron-accepting compound, alone or in combination with other electron-accepting compounds, is dispersed in a binder such as styrene-butadiene latex or polyvinyl alcohol, and applied to a support such as paper, plastic sheet, resin-coated paper, etc. A developer sheet is thereby obtained. The amount of the electron-donating colorless dye and the electron-accepting compound to be used depends on the desired coating thickness, the form of the pressure-sensitive copying paper, the capsule manufacturing method, and other conditions, and may be appropriately selected depending on the conditions. It is easy for one skilled in the art to determine this amount to use. U.S. patent for method of manufacturing capsules
A method using coacervation of a hydrophilic colloid sol described in No. 2800457 and No. 2800458,
British Patent No. 867797, British Patent No. 950443, British Patent No. 989264, British Patent No.
Examples include the interfacial polymerization method described in No. 1091076. The heat-sensitive recording material is produced by sufficiently finely pulverizing and mixing an electron-donating colorless dye, an electron-accepting compound according to the present invention, and, if necessary, a thermofusible substance, in a liquid in which a binder is dissolved or dispersed in a solvent or dispersion medium. In addition, kaolin, calcined kaolin, talc,
Oil-absorbing pigments such as waxite, diatomaceous earth, calcium carbonate, aluminum hydroxide, magnesium hydroxide, magnesium carbonate, titanium oxide, barium carbonate, urea-formalin filler, and cellulose filler are added to form a coating solution. If necessary, a paraffin wax emulsion, a latex binder, a sensitivity improver, a metal soap, an antioxidant, an ultraviolet absorber, an image storage improver, etc. can be added. The coating solution is applied to a support such as paper, plastic sheet, resin-coated paper, etc. and dried. When preparing a coating liquid, all the components may be mixed and pulverized at the same time from the beginning, or they may be combined in appropriate combinations, pulverized and dispersed separately, and then mixed. Further, the coating liquid may be poured into the support. The amounts of each component constituting the heat-sensitive recording material are 1 to 2 parts by weight of an electron-donating colorless dye, 1 part by weight of an electron-accepting compound, and 1 part by weight of an electron-donating colorless dye.
~6 parts by weight, 0 to 30 parts by weight of thermofusible substance, 0 pigments
~15 parts by weight, 1 to 15 parts by weight of binder, and 20 to 300 parts by weight of dispersion medium (solvent). One or more electron-donating colorless dyes may be used in combination. Water is most desirable as the dispersion medium (solvent). Examples of binders used in the present invention include styrene-butadiene copolymers, alkyd resins, acrylamide copolymers, vinyl chloride-vinyl acetate copolymers, styrene-maleic anhydride copolymers, synthetic rubbers, gum arabic, polyvinyl alcohol, and hydroxyethyl cellulose. etc. can be mentioned. Especially in relation to the dispersion medium (solvent), gum arabic,
Water-soluble binders such as polyvinyl alcohol, hydroxymethyl cellulose, carboxymethyl cellulose are preferred. As the thermofusible substance, erucic acid,
Stearic acid, behenic acid, palmitic acid, stearamide, behenic acid amide, stearanilide, stearic acid toluidide, N-myristoyl-p-anisidine, N-myristoyl-p-
phenetidine, 1-methoxycarbonyl-4-N
-stearylcarbamoylbenzene, N-octadecylurea, N-hexadecylurea, N,
N'-didodecylurea, phenylcarbamoyloxidedodecane, p-t-butylphenolphenoloxyacetate, p-phenylphenol-p
-chlorophenoxy acetate, 4,4'-isopropylidene bismethoxybenzene, β-phenylethyl-p-phenyl phenyl ether, 2-p
-Chlorobenzyloxynaphthalene, 2-benzyloxynaphthalene, 1-benzyloxynaphthalene, 2-phenoxyacetyloxynaphthalene, diphenyl phthalate, 1-hydroxy-2-naphthoic acid phenyl ester, 2-benzoyloxynaphthalene , p-benzyloxybenzoic acid benzyl ester, hydroquinone acetate, etc. are used. These substances are colorless solids at room temperature;
It is a substance that has a sharp melting point at a temperature suitable for the heating temperature for copying, that is, around 70 to 160°C. Examples of waxes include paraffin wax, cownabar wax, microcrystalline wax, polyethylene wax, and higher fatty acid amides such as stearic acid amide, ethylene bisstearamide, and higher fatty acid esters. Examples of metal soaps include higher fatty acid polyvalent metal salts such as zinc stearate, aluminum stearate, calcium stearate, and zinc oleate. Examples of image preservation improving agents include phenols or derivatives thereof in which at least one of the 2nd or 6th positions is substituted with an alkyl group, and among these, one or more of the 2nd or 6th positions is substituted with a tert-butyl group. phenols or derivatives thereof are preferred. Further, those having a plurality of phenol groups in the molecule are preferred, and those having 2 to 3 phenol groups are particularly preferred. Specific examples of these compounds include bis-[3,3-bis-(4'-hydroxy-3'-
tert-butylphenyl)-butanoic acid]
Glycol ester, bis-[3,3-bis-(4'-hydroxy-3',
4'-di-tert-butylphenyl)butanoitsquacid] glycol ester, bis[3,3-bis-(2'-methyl-4'-hydroxy-5'-tert-butylphenyl)-butanoitsquacid] glycol ester , 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 4,4'-thiobis (2-methyl-6-tert-butylphenol), 2,2'-thiobis(4-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-tert
-butylphenol), 2,2'-methylenebis(4-ethyl-6-tert)
-butylphenol), 4,4'-butylidenebis(3-methyl-6-
tert-butylphenol), 4,4'-methylenebis(2,6-ditert-butylphenol), 2-tert-butyl-4-tert-butoxyphenol, 2,2-dimethyl-4-isopropyl-7-
tert-butyl-6-chromanol, 2,2-dimethyl-6-t-butyl-5-benzofuranol, 4[[4,6-bis(tertbutylthio)-s-triazin-2-yl]amino]2. 6-G-tert
-Butylphenol, etc. The amount of these compounds used is 5 to 200 weight percent, preferably 20 percent by weight, based on the electron accepting compound.
~100% by weight. Examples will be shown below, but the present invention is not limited only to these examples. Example 2-anilino-3-, an electron-donating colorless dye
5g of chloro-6-diethylaminofluorane
% polyvinyl alcohol (Sapon value 99%, degree of polymerization
1000) Dispersion was carried out overnight in a ball mill with 50 g of an aqueous solution. On the other hand, similarly, 10 g of 2,4-dihydroxybenzoic acid p-chlorobenzyl ester (melting point 138-140°C), which is an electron-accepting compound, was dispersed overnight in a ball mill with 100 g of a 5% polyvinyl alcohol aqueous solution. After the dispersion was mixed, 20 g of kaolin (diyodia kaolin) was added for good dispersion, and 5 g of a 50% dispersion of paraffin wax emulsion (Chukyo Yushi Cellosol #428) was added to prepare a coating liquid. The coating liquid was applied onto a base paper having a basis weight of 50 g/m 2 so that the solid content was 6 g/m 2 and heated at 60°C.
The coated paper was obtained by drying for 1 minute. Coated paper is heated by facsimile with energy of 40
When heated and colored at mJ/mm 2 , a black printed image was obtained. The color density was 0.93. Comparative Example 1 A coated paper was obtained in the same manner as in the example except that 10 g of 2,2-bis(4-hydroxyphenyl)propane was used as the electron-accepting compound instead of the electron-accepting compound in the example. Coated paper is heated by facsimile with energy of 40
When color was developed by heating at mJ/ mm2 , the color density was 0.58.
It was hot. Comparing Examples and Comparative Example 1, it is clear that the electron-accepting compound of the present invention has extremely high coloring properties. Comparative Example 2 A coated paper was obtained in the same manner as in the example except that 10 g of benzyl 2,4-dihydroxybenzoate was used as the electron-accepting compound instead of the electron-accepting compound in the example. Coated paper is heated by facsimile with energy of 40
When heated at mJ/ mm2 , the color density was 1.05.
It was hot. Further, after this coated paper was left at 40° C. and 90% RH for 24 hours, the density of the coated paper was 0.21. On the other hand, the recording paper using the electron-accepting compound of the present invention has excellent heat and humidity resistance.
Claims (1)
用する記録材料において、該電子受容性化合物が
下記一般式で表わされる化合物であることを特徴
とする記録材料。 上式中、Rは炭素数2〜5のアルキル基、炭素
数1〜5のアルコキシ基、ハロゲン原子または、
シアノ基を表す。[Scope of Claims] 1. A recording material using an electron-donating colorless dye and an electron-accepting compound, characterized in that the electron-accepting compound is a compound represented by the following general formula. In the above formula, R is an alkyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a halogen atom, or
Represents a cyano group.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59022622A JPS60166482A (en) | 1984-02-09 | 1984-02-09 | Recording material |
GB08503291A GB2154014B (en) | 1984-02-09 | 1985-02-08 | Pressure-sensitive or heat-sensitive recording material |
US06/700,159 US4603339A (en) | 1984-02-09 | 1985-02-11 | Recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59022622A JPS60166482A (en) | 1984-02-09 | 1984-02-09 | Recording material |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60166482A JPS60166482A (en) | 1985-08-29 |
JPH0545431B2 true JPH0545431B2 (en) | 1993-07-09 |
Family
ID=12087925
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59022622A Granted JPS60166482A (en) | 1984-02-09 | 1984-02-09 | Recording material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60166482A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6289863B2 (en) * | 2013-10-25 | 2018-03-07 | 株式会社Adeka | Moisture-proofing agent, cellulosic resin composition, and film using the same |
-
1984
- 1984-02-09 JP JP59022622A patent/JPS60166482A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS60166482A (en) | 1985-08-29 |
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