JPH04142974A - Color forming recording material - Google Patents
Color forming recording materialInfo
- Publication number
- JPH04142974A JPH04142974A JP2268185A JP26818590A JPH04142974A JP H04142974 A JPH04142974 A JP H04142974A JP 2268185 A JP2268185 A JP 2268185A JP 26818590 A JP26818590 A JP 26818590A JP H04142974 A JPH04142974 A JP H04142974A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- quinoid
- color
- hydroxy aromatic
- type electron
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims description 23
- -1 hydroxy aromatic compound Chemical class 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 230000002378 acidificating effect Effects 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000004151 quinonyl group Chemical group 0.000 claims abstract description 4
- 239000004927 clay Substances 0.000 abstract description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005995 Aluminium silicate Substances 0.000 abstract description 2
- 239000005711 Benzoic acid Substances 0.000 abstract description 2
- 229930185605 Bisphenol Natural products 0.000 abstract description 2
- 235000012211 aluminium silicate Nutrition 0.000 abstract description 2
- 235000010233 benzoic acid Nutrition 0.000 abstract description 2
- 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 abstract description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N naphthoquinone group Chemical group C1(C=CC(C2=CC=CC=C12)=O)=O FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005011 phenolic resin Substances 0.000 abstract description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical group CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004056 anthraquinones Chemical group 0.000 abstract 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 4
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 4
- SNWSZCGYPHRJEY-UHFFFAOYSA-N 2-cyclohexylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C2CCCCC2)=C1 SNWSZCGYPHRJEY-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004986 phenylenediamines Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229940037312 stearamide Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- UTCOUOISVRSLSH-UHFFFAOYSA-N 1,2-Anthracenediol Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C=C21 UTCOUOISVRSLSH-UHFFFAOYSA-N 0.000 description 1
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 description 1
- CLDZVCMRASJQFO-UHFFFAOYSA-N 2,5-bis(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC(C)(C)CC(C)(C)C1=CC(O)=C(C(C)(C)CC(C)(C)C)C=C1O CLDZVCMRASJQFO-UHFFFAOYSA-N 0.000 description 1
- ZWZHTSWRPYHCGO-UHFFFAOYSA-N 2,5-bis(2-phenylpropan-2-yl)benzene-1,4-diol Chemical compound C=1C(O)=C(C(C)(C)C=2C=CC=CC=2)C=C(O)C=1C(C)(C)C1=CC=CC=C1 ZWZHTSWRPYHCGO-UHFFFAOYSA-N 0.000 description 1
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
- IZRKOTZTHHSHEF-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)benzene-1,4-diol Chemical compound CC(C)(C)CC1=CC(O)=CC=C1O IZRKOTZTHHSHEF-UHFFFAOYSA-N 0.000 description 1
- RDMIJQCFPQDYQN-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC(C)(C)CC(C)(C)C1=CC(O)=CC=C1O RDMIJQCFPQDYQN-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- OIVQLSUKOZNNCT-UHFFFAOYSA-N dibenzyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC=2C=CC=CC=2)=CC=1C(=O)OCC1=CC=CC=C1 OIVQLSUKOZNNCT-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- RQAQWBFHPMSXKR-UHFFFAOYSA-N n-(4-chlorophenyl)-3-(phosphonooxy)naphthalene-2-carboxamide Chemical compound OP(O)(=O)OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=C(Cl)C=C1 RQAQWBFHPMSXKR-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
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical class [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002112 pyrrolidino group Chemical class [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
Abstract
Description
【発明の詳細な説明】
童栗上■租朋分団
本発明は、発色性記録材料に関し、詳しくは、可視光線
乃至近赤外線に感応し、かくして、機器による情報の読
取りに有用である発色性記録材料に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a color-forming recording material, and more particularly to a color-forming recording material that is sensitive to visible light to near-infrared rays and is thus useful for reading information by equipment. Regarding materials.
従来■肢歪
従来、それ自体は無色である染料と酸性物質とからなる
発色性記録材料は、感熱記録材料として、広く実用され
ている。Conventional ■ Limb Distortion Conventionally, color-forming recording materials made of dyes and acidic substances, which are colorless in themselves, have been widely put into practical use as heat-sensitive recording materials.
しかし、近年、電子技術及び情報管理システムの発展に
伴って、可視光線の長波長域から近赤外域にわたる長波
長域の電磁波に感応する記録読取り装置が実用されるに
至っているが、従来、−Cに用いられているフタリド系
化合物を発色性染料とする発色性記録材料は、かかる長
波長域に実用的な吸収をもたない。However, in recent years, with the development of electronic technology and information management systems, recording/reading devices that are sensitive to electromagnetic waves in the long wavelength range from the long wavelength range of visible light to the near infrared range have come into practical use. A color-forming recording material using a phthalide compound used in C as a color-forming dye does not have practical absorption in such a long wavelength region.
即ち、従来、知られているフタリド系化合物の吸収波長
を近赤外域まで長波長域に移動させるためには、化合物
上の置換基効果のみならず、π電子共役系を延長する手
法も採用されているが、化合物が高分子量化し、その製
造が容易でないうえに、近赤外域の吸収は尚、十分では
ない。また、発色画像が不安定であって、褪色しやすく
、耐光性に乏しい。In other words, in order to shift the absorption wavelength of conventionally known phthalide compounds to the near-infrared region, not only the substituent effect on the compound but also a method of extending the π-electron conjugated system is adopted. However, the compound has a high molecular weight, making it difficult to manufacture, and absorption in the near-infrared region is still insufficient. In addition, the colored image is unstable, easily fades, and has poor light resistance.
そこで、近年、長波長域の電磁波を吸収する色素を形成
する発色性染料が種々提案されている。Therefore, in recent years, various color-forming dyes that form pigments that absorb electromagnetic waves in the long wavelength range have been proposed.
例えば、特開昭62−142681号公報や特開昭62
−181361号公報には、フェニレンジアミン誘導体
又はナフチレンジアミン誘導体と酸性物質とを含有する
発色性記録材料が提案されているが、発色後の経時変化
が著しい。For example, JP-A-62-142681 and JP-A-62
JP-A-181361 proposes a color-forming recording material containing a phenylene diamine derivative or a naphthylene diamine derivative and an acidic substance, but the color changes significantly over time after color development.
更に、特開昭63−256486号公報には、フェニレ
ンジアミン誘導体又はナフチレンジアミン誘導体とキノ
イド型電子受容性化合物とを含む発色性記録材料が提案
されているが、本発明者らによれば、フェニレンジアミ
ン誘導体又はナフチレンジアミン誘導体とキノイド型電
子受容性化合物とを接触させても、実質的な発色は起こ
らないので、実用化は容易でない。Further, JP-A-63-256486 proposes a color-forming recording material containing a phenylenediamine derivative or a naphthylenediamine derivative and a quinoid-type electron-accepting compound, but according to the present inventors, Even if a phenylene diamine derivative or a naphthylene diamine derivative is brought into contact with a quinoid type electron-accepting compound, no substantial color development occurs, so it is not easy to put it into practical use.
が ゛ しようとする
本発明は、上記した従来の発色性記録材料における問題
を解決するためになされたものであって、発色操作直後
に実用上十分な強度の発色を与え、しかも、可視光域か
ら近赤外域に至る長波長域に強い吸収を有する発色性記
録材料を提供することを目的とする。The present invention was made in order to solve the above-mentioned problems with conventional color-forming recording materials. It is an object of the present invention to provide a color-forming recording material that has strong absorption in the long wavelength range from 100 to 200 nm to the near infrared region.
舌 を町するための
本発明による発色性記録材料は、
(a) 一般式(I)
八−N=Y=N−B
(式中、A及びBはそれぞれ独立にアリール基を示し、
Yは二つのイミノ窒素と共役してキノイド構造を形成す
るキノン環を示す。)
で表わされるキノイド型電子受容性化合物、(ロ)多価
ヒドロキシ芳香族化合物、及び(c) 酸性物質
を含有することを特徴とする。The color-forming recording material according to the present invention for recording the tongue has the following formula: (a) General formula (I) 8-N=Y=N-B (wherein A and B each independently represent an aryl group;
Y represents a quinone ring that is conjugated with two imino nitrogens to form a quinoid structure. ) A quinoid-type electron-accepting compound represented by (b) a polyvalent hydroxy aromatic compound, and (c) an acidic substance.
即ち、本発明による発色性記録材料は、三つの要素から
なり、これらを接触させることによって、可視光域乃至
近赤外域に極めて強い吸収強度と堅牢性を有する染料を
得ることができ、従って、本発明は、半導体レーザーに
感応する実用的な発色性記録材料を提供するものである
。That is, the color-forming recording material according to the present invention consists of three elements, and by bringing these into contact, it is possible to obtain a dye that has extremely strong absorption strength and fastness in the visible light region to near-infrared region. The present invention provides a practical color-forming recording material that is sensitive to semiconductor lasers.
本発明において用いるキノイド型電子受容性化合物は、
前記一般式(I)で表わされ、ここに、A及びBは、そ
れぞれ独立にアリール基を示し、Yは二つのイミノ窒素
と共役してキノイド構造を形成するキノン環を示す。Y
としては、例えば、ベンゾキノン環、ナフトキノン環、
アントラキノン環等を例示することができる。The quinoid electron-accepting compound used in the present invention is
It is represented by the general formula (I), where A and B each independently represent an aryl group, and Y represents a quinone ring that is conjugated with two imino nitrogens to form a quinoid structure. Y
For example, benzoquinone ring, naphthoquinone ring,
Examples include an anthraquinone ring.
これらA、B及びYは、それぞれ独立にハロゲン原子、
シアノ基、水酸基、アルキル基、アリール基、アルコキ
シ基、アリールオキシ基、アラルキルオキシ基、アルキ
ルカルボニルオキシ基、アリールカルボニルオキシ基、
カルボキシル基、アルコキシカルボニル基、アリロキシ
カルボニル基、ニトロ基、アルキルスルホニル基、アリ
ールスルホニル基、アルキルスルフィニル基、アリール
スルフィニル基、アミノ基、アルキル置換アミノ基、ア
リール置換アミノ基、ピロリジノ基、ピペリジノ基及び
カルバモイル基よりなる群から選ばれる少なくとも1種
の置換基を有しでいてもよい。These A, B and Y are each independently a halogen atom,
Cyano group, hydroxyl group, alkyl group, aryl group, alkoxy group, aryloxy group, aralkyloxy group, alkylcarbonyloxy group, arylcarbonyloxy group,
carboxyl group, alkoxycarbonyl group, allyloxycarbonyl group, nitro group, alkylsulfonyl group, arylsulfonyl group, alkylsulfinyl group, arylsulfinyl group, amino group, alkyl-substituted amino group, aryl-substituted amino group, pyrrolidino group, piperidino group, and It may have at least one substituent selected from the group consisting of carbamoyl groups.
従って、このようなキノイド型電子受容性化合物として
は、例えば、N、N’−ジフェニル−p−キノンジイミ
ン、N−(4−ヒドロキシフェニル)No−フェニル−
p−キノンジイミン、N−(4メトキシフエニル)−N
o−フェニル−p−キノンジイミン、N−(4−エトキ
シフェニル)−N’−フェニル−p−キノンジイミン、
N−(3−ヒドロキシフェニル)−N“−フェニル−p
−キノンジイミン、N−(3−メトキシフェニル) −
N’フェニル−p−キノンジイミン、N−(4−tブチ
ルカルボニルオキシフェニル)−N”−フェニル−p−
キノンジイミン、N−(4−アミノフェニル)−N’−
フェニル−p−キノンジイミン、N(4−アニリノフェ
ニル)−N”−フェニル−pキノンジイミン、N−(i
(3−メトキシフェニルアミノ)フェニル−N’−フ
ェニル−p−キノンジイミン、N−(1−メチル−4−
ヒドロキシフェニル)−N’−フェニル−P−キノンジ
イミン、N−(2,3−ジメチル−4−ヒドロキシフェ
ニル)−N’−フェニル−p−キノンジイミン、N−(
2−メチル−4−メトキシフェニル)−N”−フェニル
−p−キノンジイミン等を挙げることができるが、これ
らに限定されるものではない。Therefore, such quinoid-type electron-accepting compounds include, for example, N,N'-diphenyl-p-quinonediimine, N-(4-hydroxyphenyl)No-phenyl-
p-quinonediimine, N-(4methoxyphenyl)-N
o-phenyl-p-quinonediimine, N-(4-ethoxyphenyl)-N'-phenyl-p-quinonediimine,
N-(3-hydroxyphenyl)-N“-phenyl-p
-Quinonediimine, N-(3-methoxyphenyl)-
N'phenyl-p-quinonediimine, N-(4-tbutylcarbonyloxyphenyl)-N''-phenyl-p-
Quinonediimine, N-(4-aminophenyl)-N'-
Phenyl-p-quinonediimine, N(4-anilinophenyl)-N''-phenyl-p-quinonediimine, N-(i
(3-methoxyphenylamino)phenyl-N'-phenyl-p-quinonediimine, N-(1-methyl-4-
hydroxyphenyl)-N'-phenyl-P-quinonediimine, N-(2,3-dimethyl-4-hydroxyphenyl)-N'-phenyl-p-quinonediimine, N-(
Examples include, but are not limited to, 2-methyl-4-methoxyphenyl)-N"-phenyl-p-quinone diimine.
多価ヒドロキシ芳香族化合物としては、ハイドロキノン
及びその誘導体、例えば、L−ブチルハイドロキノン、
2,6−ジーt−ブチルハイドロキノン、トリメチルハ
イドロキノン、ネオペンチルハイドロキノン、2,5−
ジネオベンチルハイドロキノン、t−オクチルハイドロ
キノン、2,5−ジt−オクチルハイドロキノン、クミ
ルハイドロキノン、2,5−ジクミルハイドロキノン、
2−シクロへキシルハイドロキノン、カテコール及びそ
の誘導体、ビフェノール及びその誘導体、例えば、3.
3’、5.5’−テトラメチルビフェノール、3,3”
、5゜5”−テトラエチルビフェノール、3.3’ 、
5.5”−テトラ−t−ブチルビフェノール、3,3′
−ジメチル5.5”−ジ−t−ブチルビフェノール、3
,5−ジメチル−3’、5’−ジーも一ブチルビフェノ
ール、2.6−ジヒドロキシナフタレン、■、4−ジヒ
ドロキシナフタレン、1,2−ジヒドロキシナフタレン
、2.3−ジヒドロキシナフタレン等のジヒドロキシナ
フタレン類、ジヒドロキシアントラセン等のアントラセ
ン類、トリヒドロキシベンゼン等を挙げることができる
。Examples of polyvalent hydroxy aromatic compounds include hydroquinone and its derivatives, such as L-butylhydroquinone,
2,6-di-t-butylhydroquinone, trimethylhydroquinone, neopentylhydroquinone, 2,5-
dineobentylhydroquinone, t-octylhydroquinone, 2,5-di-t-octylhydroquinone, cumylhydroquinone, 2,5-dicumylhydroquinone,
2-cyclohexylhydroquinone, catechol and its derivatives, biphenol and its derivatives, such as 3.
3',5.5'-tetramethylbiphenol, 3,3"
, 5゜5''-tetraethylbiphenol, 3.3',
5.5''-tetra-t-butylbiphenol, 3,3'
-dimethyl5.5”-di-t-butylbiphenol, 3
, 5-dimethyl-3',5'-di-butylbiphenol, 2,6-dihydroxynaphthalene, ■, dihydroxynaphthalenes such as 4-dihydroxynaphthalene, 1,2-dihydroxynaphthalene, and 2,3-dihydroxynaphthalene; Examples include anthracenes such as dihydroxyanthracene, trihydroxybenzene, and the like.
マタ、本発明において、酸性物質としては、有機化合物
及び無機化合物のいずれをも用いることができる。有機
化合物としては、例えば、安息香酸、ナラ1−工酸等の
芳香族カルボン酸、ヒドロキシ安息香酸、ヒドロキシナ
フトエ酸等の芳香族ヒドロキシカルボン酸、p−トルエ
ンスルホン酸等の有機スルホン酸等を挙げることができ
るが、これらに限定されるものではない。In the present invention, both organic compounds and inorganic compounds can be used as the acidic substance. Examples of the organic compound include aromatic carboxylic acids such as benzoic acid and nara-1-engineic acid, aromatic hydroxycarboxylic acids such as hydroxybenzoic acid and hydroxynaphthoic acid, and organic sulfonic acids such as p-toluenesulfonic acid. However, it is not limited to these.
他方、無機化合物としては、例えば、活性白土、酸性白
土、カオリン、クレー、フェノール樹脂等の酸性樹脂等
を挙げることができる。On the other hand, examples of inorganic compounds include activated clay, acid clay, kaolin, clay, and acidic resins such as phenol resins.
従来の通常の感熱記録材料は、よく知られているように
、発色性染料とビスフェノールへのような顕色剤や、そ
の他必要に応じて用いられる添加剤と共にバインダーを
含む水分散液を調製し、これを紙のような基材上に塗布
し、乾燥して調製される。本発明による発色性記録材料
も、感熱記録材料として用いる場合、上記と同様に、前
記キノイド型電子受容性化合物と多価ヒドロキシ芳香族
化合物と酸性物質や、その他必要に応じて用いられる添
加剤と共にバインダーを含む水分散液を調製し、これを
紙のような基材上に塗布し、乾燥すればよい。As is well known, conventional heat-sensitive recording materials are prepared by preparing an aqueous dispersion containing a binder together with a color-forming dye, a color developer such as bisphenol, and other additives used as necessary. It is prepared by coating it on a substrate such as paper and drying it. When the color-forming recording material according to the present invention is also used as a heat-sensitive recording material, the quinoid type electron-accepting compound, the polyvalent hydroxy aromatic compound, the acidic substance, and other additives used as necessary are used in the same manner as above. An aqueous dispersion containing a binder may be prepared, applied onto a substrate such as paper, and dried.
上記バインダーとしては、従来より感熱記録材料の調製
に用いられているものを好適に用いることができ、かか
るバインダーとしては、例えば、ポリビニルアルコール
、ヒドロキシエチルセルロース、ポリアクリル酸ナトリ
ウム、ポリビニルピロリドン、ポリ酢酸ビニル、ポリウ
レタン、ポリアクリル酸、ポリアクリル酸エステル、種
々のラテックス等を挙げることができる。As the binder, those conventionally used in the preparation of heat-sensitive recording materials can be suitably used. Examples of such binders include polyvinyl alcohol, hydroxyethyl cellulose, sodium polyacrylate, polyvinylpyrrolidone, polyvinyl acetate, etc. , polyurethane, polyacrylic acid, polyacrylic acid ester, various latexes, and the like.
本発明による発色性記録材料においては、前記キノイド
型電子受容性化合物と多価ヒドロキシ芳香族化合物は、
キノイド型電子受容性化合物/多価ヒドロキシ芳香族化
合物モル比が0.01〜100、好ましくは0.05〜
20の範囲で用いられる。In the color-forming recording material according to the present invention, the quinoid type electron-accepting compound and the polyvalent hydroxy aromatic compound are:
The molar ratio of quinoid electron-accepting compound/polyvalent hydroxy aromatic compound is 0.01 to 100, preferably 0.05 to 100.
Used in the range of 20.
本発明による発色性記録材料は、蛍光染料や顔料を含有
していてもよい。蛍光染料として、例えば、ジアミノス
チルベン系、ベンズイミダゾール系、ベンジジン系、イ
ミダシロン系等を挙げることができる。また、顔料とし
ては、二酸化チタン、クレー、タルク、炭酸カルシウム
、水酸化アルミニウム、シリカ、ポリスチレン樹脂、ホ
ルマリン樹脂等を挙げることができる。The color-forming recording material according to the present invention may contain fluorescent dyes and pigments. Examples of fluorescent dyes include diaminostilbene-based, benzimidazole-based, benzidine-based, and imidasilone-based dyes. Examples of pigments include titanium dioxide, clay, talc, calcium carbonate, aluminum hydroxide, silica, polystyrene resin, formalin resin, and the like.
更に、本発明による発色性記録材料は、増感剤を含有し
ていてもよい。増感剤としては、例えば、ステアリン酸
アミドのような高級脂肪酸アミド、ベンズアミド、ステ
アリン酸アニリド、アセト酢酸アニリド、チオアセ1−
アニリド、フタル酸ジメチル、テレフタル酸ジベンジル
、イソフタル酸ジベンジル、4,4゛−ジメトキシジフ
ェニルスルホン等を挙げることができる。また、ステア
リン酸、ステアリン酸亜鉛、ステアリン酸カルシウム、
カルナウバワックス、パラフィンワックス等の粘着防止
剤も含有することができる。また、オーバーコート層を
設けることができる。Furthermore, the color-forming recording material according to the invention may contain a sensitizer. Examples of the sensitizer include higher fatty acid amides such as stearamide, benzamide, stearanilide, acetoacetanilide, and thioacetate 1-
Examples include anilide, dimethyl phthalate, dibenzyl terephthalate, dibenzyl isophthalate, and 4,4'-dimethoxydiphenyl sulfone. In addition, stearic acid, zinc stearate, calcium stearate,
Anti-blocking agents such as carnauba wax and paraffin wax may also be included. Additionally, an overcoat layer can be provided.
光凱少盈果
本発明による発色性記録材料は、以上のように、キノイ
ド型電子受容性化合物と多価ヒドロキシ芳香族化合物と
酸性物質とを含み、発色操作直後に実用上十分な強度の
発色を与え、しかも、可視光域から近赤外域に至る長波
長域に強い吸収を有するので、機器による情報の読取り
に有用である。As described above, the color-forming recording material according to the present invention contains a quinoid-type electron-accepting compound, a polyhydric hydroxy aromatic compound, and an acidic substance, and develops a color with sufficient intensity for practical use immediately after the color-forming operation. Furthermore, it has strong absorption in the long wavelength range from visible light to near-infrared light, making it useful for reading information with equipment.
実施■
以下に実施例を挙げて本発明を説明するが、本発明はこ
れら実施例により何ら限定されるものではない。Implementation (2) The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples in any way.
キノイド型電子受容性化合物0.0264 g、ステア
リン酸アミド0.0264 g、10重量%ポリビニル
アルコール水溶液0.066 g及び水06145gを
ボールミルにて20時間処理して、分散液Aを得た。Dispersion A was obtained by processing 0.0264 g of a quinoid electron-accepting compound, 0.0264 g of stearamide, 0.066 g of a 10% by weight aqueous polyvinyl alcohol solution, and 06145 g of water in a ball mill for 20 hours.
別に、酸性物質0.5g、多価ヒドロキシ芳香族化合物
0.026g、ステアリン酸亜鉛0.3g、10重量%
ポリビニルアルコール水溶液1.5g及び水5.0gを
ボールミルにて20時間処理して、分散液Bを得た。Separately, 0.5 g of acidic substance, 0.026 g of polyvalent hydroxy aromatic compound, 0.3 g of zinc stearate, 10% by weight.
Dispersion B was obtained by processing 1.5 g of a polyvinyl alcohol aqueous solution and 5.0 g of water in a ball mill for 20 hours.
次いで、分散液Aに分散液B 1. Ogを加え、バー
コーターを用いて上質紙に塗布し、風乾した後、NEC
プリンター(PC−PR102TL)のす■
−マルヘッドを用いてバーコードを印字させた。Next, dispersion liquid B is added to dispersion liquid A. 1. Add Og, apply it to high-quality paper using a bar coater, air dry, and then apply NEC
A barcode was printed using a printer (PC-PR102TL) using a square head.
このバーコードをSymbol Technologi
es、 Inc、製の半導体レーザー(780nm)バ
ーコードリーダーを用いて読み取った。結果を第1表に
示す。Please send this barcode to Symbol Technology.
It was read using a semiconductor laser (780 nm) barcode reader manufactured by ES, Inc. The results are shown in Table 1.
尚、第1表において、モル比は、キノイド型電子受容性
化合物/多価ヒドロキシ芳香族化合物モル比を示し、読
取り回数は10回の読取り回数中を示す。In Table 1, the molar ratio indicates the quinoid electron-accepting compound/polyvalent hydroxy aromatic compound molar ratio, and the number of readings indicates the number of readings out of 10.
また、上記において用いたキノイド型電子受容性化合物
、多価ヒドロキシ芳香族化合物及び酸性物質を次のとお
りである。Further, the quinoid type electron-accepting compound, polyvalent hydroxy aromatic compound, and acidic substance used in the above are as follows.
キノイド型電子受容性化合物
(a) N、N’−ジフェニル−p−キノンジイミン(
b)N−(4−メトキシフェニル)−N゛−フェニル−
p−キノンジイミン
(c)N−(2−メチル−4−メトキシフェニル)N゛
−フェニル−p−キノンジイミン
(d)なし
多価ヒドロキシ芳香族化合物
(1)ハイドロキノン
(2)2.6−シヒドロキシナフタレン(3)2−シク
ロヘキシルハイドロキノン(4)ビフェノール
(5) 3.3’、5.5”−テトラ−t−ブチルビフ
ェノール
酸性物質
(イ)1−ヒドロキシ−2−ナフトエ酸(ロ)クレー
(ハ)なし
く以下、余白)
第
表
第
■
表(続き)
第
表(続き)Quinoid-type electron-accepting compound (a) N,N'-diphenyl-p-quinonediimine (
b) N-(4-methoxyphenyl)-N゛-phenyl-
p-quinonediimine (c) N-(2-methyl-4-methoxyphenyl)N-phenyl-p-quinonediimine (d) Polyhydric hydroxy aromatic compound (1) Hydroquinone (2) 2,6-hydroxynaphthalene (3) 2-cyclohexylhydroquinone (4) Biphenol (5) 3.3',5.5''-tetra-t-butylbiphenol acidic substance (a) 1-hydroxy-2-naphthoic acid (b) Clay (c) (without spaces below) Table 1 ■ Table (continued) Table (continued)
Claims (1)
Yは二つのイミノ窒素と共役してキノイド構造を形成す
るキノン環を示す。) で表わされるキノイド型電子受容性化合物、 (b)多価ヒドロキシ芳香族化合物、及び (c)酸性物質 を含有することを特徴とする発色性記録材料。(1) (a) General formula (I) A-N=Y=N-B (wherein A and B each independently represent an aryl group,
Y represents a quinone ring that is conjugated with two imino nitrogens to form a quinoid structure. 1. A color-forming recording material characterized by containing a quinoid electron-accepting compound represented by (b) a polyvalent hydroxy aromatic compound, and (c) an acidic substance.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2268185A JP3045175B2 (en) | 1990-10-04 | 1990-10-04 | Chromogenic recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2268185A JP3045175B2 (en) | 1990-10-04 | 1990-10-04 | Chromogenic recording material |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04142974A true JPH04142974A (en) | 1992-05-15 |
JP3045175B2 JP3045175B2 (en) | 2000-05-29 |
Family
ID=17455100
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2268185A Expired - Fee Related JP3045175B2 (en) | 1990-10-04 | 1990-10-04 | Chromogenic recording material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3045175B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6447649B1 (en) * | 2000-07-24 | 2002-09-10 | Ge Betz, Inc. | Polymerization inhibitor for vinyl-containing materials |
-
1990
- 1990-10-04 JP JP2268185A patent/JP3045175B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6447649B1 (en) * | 2000-07-24 | 2002-09-10 | Ge Betz, Inc. | Polymerization inhibitor for vinyl-containing materials |
Also Published As
Publication number | Publication date |
---|---|
JP3045175B2 (en) | 2000-05-29 |
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