JP2004223884A - New thermal recording material - Google Patents
New thermal recording material Download PDFInfo
- Publication number
- JP2004223884A JP2004223884A JP2003014495A JP2003014495A JP2004223884A JP 2004223884 A JP2004223884 A JP 2004223884A JP 2003014495 A JP2003014495 A JP 2003014495A JP 2003014495 A JP2003014495 A JP 2003014495A JP 2004223884 A JP2004223884 A JP 2004223884A
- Authority
- JP
- Japan
- Prior art keywords
- recording material
- color
- compound
- hydroxyphenyl
- diethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000000463 material Substances 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004040 coloring Methods 0.000 claims description 20
- 239000000243 solution Substances 0.000 abstract description 23
- 238000010438 heat treatment Methods 0.000 abstract description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- -1 tris (hydroxyphenyl) ethane compound Chemical class 0.000 description 26
- 239000010410 layer Substances 0.000 description 23
- 239000011241 protective layer Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 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
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000008378 aryl ethers Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-UHFFFAOYSA-N 0.000 description 2
- HUSIBQLZEMMTCQ-UHFFFAOYSA-N 2'-anilino-6'-[ethyl(3-methylbutyl)amino]-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCC(C)C)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 HUSIBQLZEMMTCQ-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- MTMKZABGIQJAEX-UHFFFAOYSA-N 4,4'-sulfonylbis[2-(prop-2-en-1-yl)phenol] Chemical compound C1=C(CC=C)C(O)=CC=C1S(=O)(=O)C1=CC=C(O)C(CC=C)=C1 MTMKZABGIQJAEX-UHFFFAOYSA-N 0.000 description 2
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- JJXVDRYFBGDXOU-UHFFFAOYSA-N dimethyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(O)C=C1C(=O)OC JJXVDRYFBGDXOU-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 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 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000004897 thiazines Chemical class 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
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- YKPAABNCNAGAAJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)propane Chemical compound C=1C=C(O)C=CC=1C(CC)C1=CC=C(O)C=C1 YKPAABNCNAGAAJ-UHFFFAOYSA-N 0.000 description 1
- JTWBMEAENZGSOQ-UHFFFAOYSA-N 1,2-bis(phenoxymethyl)benzene Chemical compound C=1C=CC=C(COC=2C=CC=CC=2)C=1COC1=CC=CC=C1 JTWBMEAENZGSOQ-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- BDCNTSHIADXFPV-UHFFFAOYSA-N 1-chloro-4-(2-phenoxyethoxy)benzene Chemical compound C1=CC(Cl)=CC=C1OCCOC1=CC=CC=C1 BDCNTSHIADXFPV-UHFFFAOYSA-N 0.000 description 1
- IYQIAVRZWFMVGZ-UHFFFAOYSA-N 1-methoxy-4-(2-phenoxyethoxy)benzene Chemical compound C1=CC(OC)=CC=C1OCCOC1=CC=CC=C1 IYQIAVRZWFMVGZ-UHFFFAOYSA-N 0.000 description 1
- VGMACPCJKUXETI-UHFFFAOYSA-N 1-methoxy-4-[2-(4-methoxyphenoxy)ethoxy]benzene Chemical compound C1=CC(OC)=CC=C1OCCOC1=CC=C(OC)C=C1 VGMACPCJKUXETI-UHFFFAOYSA-N 0.000 description 1
- OAGNKYSIOSDNIG-UHFFFAOYSA-N 1-methyl-3-[2-(3-methylphenoxy)ethoxy]benzene Chemical compound CC1=CC=CC(OCCOC=2C=C(C)C=CC=2)=C1 OAGNKYSIOSDNIG-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
- GSCLSACFHWKTQU-UHFFFAOYSA-N 2'-chloro-6'-(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Cl)=CC=C1OC1=CC(N(CC)CC)=CC=C21 GSCLSACFHWKTQU-UHFFFAOYSA-N 0.000 description 1
- QFKZBYXKHJHWSO-UHFFFAOYSA-N 2-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]propanenitrile Chemical compound C1=CC(N(C)C)=CC=C1CC(C#N)C1=CC=C(N)C=C1 QFKZBYXKHJHWSO-UHFFFAOYSA-N 0.000 description 1
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 description 1
- NODRXLWVBKZXOO-UHFFFAOYSA-N 2-(hydroxymethyl)docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(CO)C(N)=O NODRXLWVBKZXOO-UHFFFAOYSA-N 0.000 description 1
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 1
- XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-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
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- QVLMURXSBNAVPP-UHFFFAOYSA-N 3-[1,2-bis(methylamino)indol-3-yl]-3-[4-(dimethylamino)phenyl]-2-benzofuran-1-one Chemical compound C12=CC=CC=C2N(NC)C(NC)=C1C1(C2=CC=CC=C2C(=O)O1)C1=CC=C(N(C)C)C=C1 QVLMURXSBNAVPP-UHFFFAOYSA-N 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Description
【0001】
【発明の属する技術分野】
本発明は感熱記録材料に関し、特に印字濃度が十分で、且つ高温下での耐熱性に優れた感熱記録材料に関するものである。
【0002】
【従来の技術】
感熱記録材料は、一般にロイコ染料とフェノール性物質等の顕色剤をそれぞれ別個に微粒子状に分散化後、両者を混合し、これに結合剤、増感剤、充填剤、滑剤等の添加剤を添加して塗液とし、紙、フィルム、合成紙等に塗布したもので、加熱によりロイコ染料と顕色剤の一方又は両者が溶融、接触して起こる化学反応により発色記録を得るものである。この感熱記録シートの発色のためには、サーマルヘッドを内蔵したサーマルプリンター等が用いられる。この感熱記録法は他の記録法に比較して(1)記録時に騒音がでない、(2)現像、定着等の必要がない、(3)メンテナンスフリーである、(4)機械が比較的安価である等の特徴により、ファクシミリ分野、コンピューターのアウトプット、電卓等のプリンター分野、医療計測用のレコーダー分野、自動券売機分野、感熱記録型ラベル分野等に広く用いられている。
【0003】
近年では、小売店、コンビニエンスストア、ス−パーマーケット等におけるPOSシステム化、交通機関における自動化システムに伴うラベル類や乗車券、回数券等への使用が普及している。これらの用途において、感熱記録材料にはより一層の保存安定性の向上が望まれている。例えばコンビニ食品あるいは冷凍食品の加熱、解凍処理や車内放置されるカード類がある。また高速記録に対する要求が一段と高くなり高速記録に十分対応し得る感熱記録材料の開発が強く望まれているが、一般に感熱記録材料の感度を高め熱応答性を良くすると製造時及び使用時あるいは保管により地肌かぶりが起こるという欠点があらわれやすくなる。又別の方法として、支持体と感熱発色層の間に特定の中間層を設ける方法も検討されているが加工性及び経済性の点から不十分である。
一方、耐熱性を向上させるためにトリス(ヒドロキシフェニル)エタン系化合物を含有させることが提案されている(例えば特許文献1、2参照)。
【特許文献1】
特開平6−115255号公報
【特許文献2】
特開平7−314904号公報
【0004】
【発明が解決しようとする課題】
本発明の目的は前記、従来技術の欠点を解決することにある。即ち、印字濃度が十分で、且つ高温下での耐熱性に優れた感熱記録材料を提供することである。
【0005】
【課題を解決するための手段】
本発明者は前記目的を達成すべく種々の検討を重ねた結果、本発明を完成させたものである。即ち本発明は、
(1)通常無色ないし淡色の発色性化合物と該発色性化合物を熱時発色させうる顕色性化合物を使用する感熱記録材料において、発色性化合物として3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオランを、又顕色性化合物として1,1,1−トリス(p−ヒドロキシフェニル)エタンを、それぞれ含有することを特徴とする感熱記録材料、
に関する。
【0006】
【発明の実施の形態】
本発明を詳細に説明する。本発明の感熱記録材料は発色性化合物として3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオランを、顕色性化合物として1,1,1−トリス(p−ヒドロキシフェニル)エタンを、主要な成分としてそれぞれ使用し、以下に示すような結合剤及びその他必要に応じ充填剤、増感剤、その他の添加物等を使用して感熱発色層が調製される。
【0007】
本発明における感熱発色層を形成するにあたり、3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオランは通常1〜50重量%、好ましくは5〜30重量%、1,1,1−トリス(p−ヒドロキシフェニル)エタンは通常1〜60重量%、好ましくは5〜30%、結合剤は通常1〜90重量%、充填剤、増感剤は通常各々0〜80重量%、その他の滑剤、界面活性剤、消泡剤、紫外線吸収剤等は各々任意の割合で、例えば通常各々0〜30重量%、使用される(重量%は感熱発色層中に占める各成分の重量比)。
【0008】
更に好ましい態様においては、上記のような組成のうちで、各々の使用量が重量比で3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン1に対して1,1,1−トリス(p−ヒドロキシフェニル)エタンは通常0.5〜20倍、好ましくは1〜5倍の重量比の範囲で使用される。
更に本発明の感熱記録材料においては、本発明の主要成分以外の公知の発色性化合物及び顕色性化合物をそれぞれ併用しても構わない。
【0009】
本発明における併用可能な発色性化合物の例としては、一般に感圧記録紙や感熱記録紙に用いられているものであればよく、特に制限されない。用いうる発色性化合物の例としては、例えばフルオラン系化合物、トリアリールメタン系化合物、スピロ系化合物、ジフェニルメタン系化合物、チアジン系化合物、ラクタム系化合物、フルオレン系化合物等が挙げられる。
【0010】
用いうるフルオラン系化合物の具体例としては、例えば3−ジエチルアミノ−6−メチル−7−アニリノフルオラン、3−ジブチルアミノ−6−メチル−7−アニリノフルオラン、3−(N−メチル−N−シクロヘキシルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−イソペンチルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−イソブチルアミノ)−6−メチル−7−アニリノフルオラン、3−[N−エチル−N−(3−エトキシプロピル)アミノ]−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−ヘキシルアミノ)−6−メチル−7−アニリノフルオラン、3−ジペンチルアミノ−6−メチル−7−アニリノフルオラン、3−(N−メチル−N−プロピルアミノ)−6−メチル−7−アニリノフルオラン、3−(N−エチル−N−テトラヒドロフリルアミノ)−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチル−7−(p−クロロアニリノ)フルオラン、3−ジエチルアミノ−6−メチル−7−(p−フルオロアニリノ)フルオラン、3−[N−エチル−N−(p−トリル)アミノ]−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−メチル−7−(p−トルイジノ)フルオラン、3−ジエチルアミノ−7−(o−クロロアニリノ)フルオラン、3−ジブチルアミノ−7−(o−クロロアニリノ)フルオラン、3−ジブチルアミノ−7−(o−フルオロアニリノ)フルオラン、3−ジエチルアミノ−7−(3,4−ジクロロアニリノ)フルオラン、3−ピロリジノ−6−メチル−7−アニリノフルオラン、3−ジエチルアミノ−6−クロロ−7−エトキシエチルアミノフルオラン、3−ジエチルアミノ−6−クロロ−7−アニリノフルオラン、3−ジエチルアミノ−7−クロロフルオラン、3−ジエチルアミノ−7−メチルフルオラン、3−ジエチルアミノ−7−オクチルフルオラン、3−[N−エチル−N−(p−トリル)アミノ]−6−メチル−7−フェネチルフルオラン等が挙げられる。
【0011】
又、用いうるトリアリールメタン系化合物の具体例としては、例えば3,3−ビス(p−ジメチルアミノフェニル)−6−ジメチルアミノフタリド(別名:クリスタルバイオレットラクトン又はCVL)、3,3−ビス(p−ジメチルアミノフェニル)フタリド、3−(p−ジメチルアミノフェニル)−3−(1,2−ジメチルアミノインドール−3−イル)フタリド、3−(p−ジメチルアミノフェニル)−3−(2−メチルインドール−3−イル)フタリド、3−(p−ジメチルアミノフェニル)−3−(2−フェニルインドール−3−イル)フタリド、3,3−ビス(1,2−ジメチルインドール−3−イル)−5−ジメチルアミノフタリド、3,3−ビス(1,2−ジメチルインドール−3−イル)−6−ジメチルアミノフタリド、3,3−ビス(9−エチルカルバゾール−3−イル)−5−ジメチルアミノフタリド、3,3−(2−フェニルインドール−3−イル)−5−ジメチルアミノフタリド、3−p−ジメチルアミノフェニル−3−(1−メチルピロール−2−イル)−6−ジメチルアミノフタリド等が挙げられる。
【0012】
更に、用いうるスピロ系化合物の具体例としては、例えば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ピラン、3−ベンジルスピロジナフトピラン、3−プロピルスピロベンゾピラン、3−メチルナフト−(3−メトキシベンゾ)スピロピラン、1,3,3−トリメチル−6−ニトロ−8’−メトキシスピロ(インドリン−2,2’−ベンゾピラン)等が、ジフェニルメタン系化合物の具体例としては、例えばN−ハロフェニル−ロイコオーラミン、4,4−ビス−ジメチルアミノフェニルベンズヒドリルベンジルエーテル、N−2,4,5−トリクロロフェニルロイコオーラミン等が、チアジン系化合物の具体例としては、例えばベンゾイルロイコメチレンブルー、p−ニトロベンゾイルロイコメチレンブルー等が、ラクタム系化合物の具体例としては、例えばローダミンB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等が、フルオレン系化合物の具体例としては、例えば3,6−ビス(ジメチルアミノ)フルオレンスピロ(9,3’)−6’−ジメチルアミノフタリド、3,6−ビス(ジメチルアミノ)フルオレンスピロ(9,3’)−6’−ピロリジノフタリド、3−ジメチルアミノ−6−ジエチルアミノフルオレンスピロ(9,3’)−6’−ピロリジノフタリド等が挙げられる。これらの発色性化合物は単独もしくは混合して用いられる。
【0013】
本発明において、1,1,1−トリス(p−ヒドロキシフェニル)エタンと併用可能な顕色性化合物としては、一般に感圧記録紙や感熱記録紙に用いられているものであればよくいずれも使用可能で、特に制限されない。具体例としては、例えばα−ナフトール、β−ナフトール、p−オクチルフェノール、4−t−オクチルフェノール、p−t−ブチルフェノール、p−フェニルフェノール、1,1−ビス(p−ヒドロキシフェニル)プロパン、2,2−ビス(p−ヒドロキシフェニル)プロパン(別名:ビスフェノールA又はBPA)、2,2−ビス(p−ヒドロキシフェニル)ブタン、2,2−ビス(3,5−ジブロム−4−ヒドロキシフェニル)プロパン、1,1−ビス(p−ヒドロキシフェニル)シクロヘキサン、4,4’−チオビスフェノール、4,4’−シクロ−ヘキシリデンジフェノール、4,4’−イソウロピリデンビス(2−t−ブチルフェノール)、2,2’−メチレンビス(4−クロロフェノール)、4,4’−ジヒドロキシジフェニルスルホン、2,4’−ジヒドロキシジフェニルスルホン、ビス(3−アリル−4−ヒドロキシフェニル)スルホン、4−ヒドロキシ−4’−イソプロポキシジフェニルスルホン、4−ヒドロキシ−4’−ベンジルオキシジフェニルスルホン、ビス(4−ヒドロキシフェニル)酢酸メチル、ビス(4−ヒドロキシフェニル)酢酸ブチル、ビス(4−ヒドロキシフェニル)酢酸ベンジル等のフェノール性化合物、p−ヒドロキシ安息香酸ベンジル、p−ヒドロキシ安息香酸エチル、4−ヒドロキシフタル酸ジベンジル、4−ヒドロキシフタル酸ジメチル、5−ヒドロキシイソフタル酸エチル、3,5−ジ−t−ブチルサリチル酸、3,5−ジ−α−メチルベンジルサリチル酸等の芳香族カルボン酸誘導体、芳香族カルボン酸又はその多価金属塩等が挙げられるが、これらのものに制限されない。
【0014】
本発明において用いうる増感剤(熱可融性化合物)としては、例えば動植物性ワックス、合成ワックスなどのワックス類や高級脂肪酸、高級脂肪酸アミド、高級脂肪酸アニリド、ナフタレン誘導体、芳香族エーテル、芳香族カルボン酸誘導体、芳香族スルホン酸エステル誘導体、炭酸又はシュウ酸ジエステル誘導体、ビフェニル誘導体、ターフェニル誘導体、ウルホン誘導体等、常温では固体であり約70℃以上の融点を有するものを使用することができる。
【0015】
ワックス類としては、例えば木ろう、カルナウバろう、シェラック、パラフィン、モンタンろう、酸化パラフィン、ポリエチレンワックス、酸化ポリエチレン等が、高級脂肪酸としては、例えばステアリン酸、ベヘン酸等が、高級脂肪酸アミドとしては、例えばステアリン酸アミド、オレイン酸アミド、N−メチルステアリン酸アミド、エルカ酸アミド、メチロールベヘン酸アミド、メチレンビスステアリン酸アミド、エチレンビスステアリン酸アミド等が、高級脂肪酸アニリドとしては、例えばステアリン酸アニリド、リノール酸アニリド等が、ナフタレン誘導体としては、例えば1−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−ヒドロキシナフトエ酸フェニルエステル等が、芳香族エーテルとしては、例えば1,2−ジフェノキシエタン、1,4−ジフェノキシブタン、1,2−ビス(3−メチルフェノキシ)エタン、1,2−ビス(4−メトキシフェノキシ)エタン、1,2−ビス(3,4−ジメチルフェニル)エタン、1−フェノキシ−2−(4−クロロフェノキシ)エタン、1−フェノキシ−2−(4−メトキシフェノキシ)エタン、1,2−ジフェノキシメチルベンゼン等が、芳香族カルボン酸誘導体としては、例えばp−ヒドロキシ安息香酸ベンジルエステル、p−ベンジルオキシ安息香酸ベンジルエステル、テレフタル酸ジベンジルエステル等が、芳香族スルホン酸エステル誘導体としては、例えばp−トルエンスルホン酸フェニルエステル、フェニルメシチレンスルホナート、4−メチルフェニルメシチレンスルホナート等が、炭酸又はシュウ酸ジエステル誘導体としては、例えば炭酸ジフェニル、シュウ酸ジベンジルエステル、シュウ酸ジ(4−クロロベンジル)エステル、シュウ酸ジ(4−メチルベンジル)エステル類が、ビフェニル誘導体としては、例えばp−ベンジルビフェニル、p−アリルオキシブフェニル等が、ターフェニル誘導体としては、例えばm−ターフェニル等が、スルホン誘導体としては、例えばジフェニルスルホン等が、それぞれ例示される。
【0016】
前記した併用可能な発色性化合物及び顕色性化合物の使用量は、本発明の効果を妨げない範囲、例えば3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン、1,1,1−トリス(p−ヒドロキシフェニル)エタンの使用量をそれぞれ越えない範囲の割合が好ましい。
【0017】
用いうる結合剤の具体例としては、例えばメチルセルロース、メトキシセルロース、ヒドロキシエチルセルロース、カルボキシメチルセルロース、ナトリウムカルボキシメチルセルロース、セルロース、ポリビニルアルコール(PVA)、カルボキシル基変性ポリビニルアルコール、スルホン酸基変性ポリビニルアルコール、ポリビニルピロリドン、ポリアクリルアミド、ポリアクリル酸、デンプン及びその誘導体、カゼイン、ゼラチン、水溶性イソプレンゴム、スチレン/無水マレイン酸共重合体のアルカリ塩、イソ(又はジイソ)ブチレン/無水マレイン酸共重合体のアルカリ塩等の水溶性のもの或はポリ酢酸ビニル、塩化ビニル/酢酸ビニル共重合体、ポリスチレン、ポリアクリル酸エステル、ポリウレタン、スチレン/ブタジエン(SB)共重合体、カルボキシル化スチレン/ブタジエン(SB)共重合体、スチレン/ブタジエン/アクリル酸系共重合体、コロイダルシリカとアクリル樹脂の複合体粒子等の疎水性高分子エマルジョン等が用いられる。
【0018】
用いうる充填剤の具体例としては、例えば炭酸カルシウム、炭酸マグネシウム、酸化マグネシウム、シリカ、ホワイトカーボン、タルク、クレー、アルミナ、水酸化マグネシウム、水酸化アルミニウム、酸化アルミニウム、硫酸バリウム、ポリスチレン樹脂、尿素−ホルマリン樹脂等があげられる。
【0019】
更に、本発明においては上記以外の種々の添加剤を使用することができるが、用いうるその他の添加物の例としては、例えばサ−マルヘッド摩耗防止、スティッキング防止等の目的でのステアリン酸亜鉛、ステアリン酸カルシウム等の高級脂肪酸金属塩、酸化防止或は老化防止効果を付与する為のフェノール誘導体、ベンゾフェノン系化合物、ベンゾトリアゾール系化合物等の紫外線吸収剤、各種の界面活性剤、消泡剤等がそれぞれ挙げられる。
【0020】
前記材料を用いて例えば次のような方法によって本発明の感熱記録材料が調製される。即ち、常法によりまず3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン、1,1,1−トリス(p−ヒドロキシフェニル)エタンをそれぞれ別々に結合剤あるいは必要に応じてその他の添加剤等と共にボールミル、アトライター、サンドミルなどの分散機にて粉砕、分散化した後(粉砕、分散を湿式で行うときは通常水を媒体として用いる)混合して感熱発色層塗布液を調製し、紙、プラスチックシート、合成紙等の支持体上に通常乾燥重量で1〜20g/m2になるようにバーコーター、ブレードコーター等により塗布、乾燥して本発明の感熱記録材料を得る。又、必要に応じて感熱発色層と支持体の間に中間層を設けたり感熱発色層上にオーバーコート層(保護層)を設けてもよい。中間層、オーバーコート層(保護層)は、例えば前記したような結合剤あるいは必要に応じてその他の添加物と共に感熱発色層塗布液調製におけるのと同様に粉砕、分散して中間層塗布液又はオーバーコート層(保護層)塗布液とした後、乾燥時の重量で通常0.1〜5g/m2程度となるように塗布し、乾燥することにより設けられる。
【0021】
3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン、1,1,1−トリス(p−ヒドロキシフェニル)エタンを含有する本発明の感熱記録材料は、従来公知のものに比べ印字濃度に優れ、且つ高温下での耐熱性に優れている。
【0022】
【実施例】
本発明を実施例によりさらに具体的に説明するが、本発明がこれらに限定されるものではない。実施例中「部」は重量部、「%」は重量%をそれぞれ示す。
【0023】
実施例1
(感熱発色層の形成)
下記組成の混合物をサンドグラインダーを用いて平均粒径が1μm以下になるように粉砕、分散化してそれぞれ[A]液、[B]液を調製した。
[A]液:3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオラン25部
25%PVA水溶液 20部
水 55部
[B]液:1,1,1−トリス(p−ヒドロキシフェニル)エタン 25部
25%PVA水溶液 20部
水 55部
【0024】
次いで、上記で得た各液及び下記する薬剤を下記の割合で混合して感熱発色層塗布液を調製し、厚さ188μmの白色ポリエステルフィルム(東レ(株)製、ルミラーE22)上に乾燥時の重量が10g/m2となるように塗布、乾燥して感熱発色層を形成した。
[A]液 8部
[B]液 20部
50%炭酸カルシウム水分散液 10部
50%カルボキシル化SB共重合体エマルジョン 6部
【0025】
(保護層の形成)
次に下記組成の混合物を調製して保護層塗布液とし、前記感熱発色層上に乾燥時の重量が3g/m2となるように塗布、乾燥して保護層付きの本発明の感熱記録材料を得た。
40%スチレン/アクリル酸エステル共重合体エマルジョン 17部
5%ベントナイト水分散液 30部
30%ステアリン酸亜鉛水分散液 4部
【0026】
実施例2
下記組成の混合物をサンドグラインダーを用いて平均粒径が1μm以下になるように粉砕、分散化して[C]液を調製した。
[C]液:3−ジブチルアミノ−6−メチル−7−アニリノフルオラン25部
25%PVA水溶液 20部
水 55部
【0027】
次いで、上記で得た各液及び下記する薬剤を下記の割合で混合して感熱発色層塗布液を調製し、厚さ188μmの白色ポリエステルフィルム(東レ(株)製、ルミラーE22)上に乾燥時の重量が10g/m2となるように塗布、乾燥して感熱発色層を形成した。
[A]液 6部
[B]液 20部
[C]液 2部
50%炭酸カルシウム水分散液 10部
50%カルボキシル化SB共重合体エマルジョン 6部
(保護層の形成)
更に実施例1と同様にして保護層を設け、保護層つきの本発明の感熱記録材料を得た。
【0028】
実施例3
下記組成の混合物をサンドグラインダーを用いて平均粒径が1μm以下にな液ように粉砕、分散化して[D]液を調製した。
【0029】
次いで、上記で得た各液及び下記する薬剤を下記の割合で混合して感熱発色層塗布液を調製し、厚さ188μmの白色ポリエステルフィルム(東レ(株)製、ルミラーE22)上に乾燥時の重量が10g/m2となるように塗布、乾燥して感熱発色層を形成した。
[A]液 8部
[B]液 16部
[D]液 4部
50%炭酸カルシウム水分散液 10部
50%カルボキシル化SB共重合体エマルジョン 6部
(保護層の形成)
更に実施例1と同様にして保護層を設け、保護層つきの本発明の感熱記録材料を得た。
【0030】
比較例1
実施例1の[A]液における3−ジエチルアミノ−7−(o−フルオロアニリノ)フルオランの代わりに3−(N−エチル−N−イソペンチルアミノ)−6−メチル−7−アニリノフルオランを使用して比較用の感熱記録材料を得た。
【0031】
比較例2
実施例1の[B]液における1,1,1−トリス(p−ヒドロキシフェニル)エタンの代わりにビス(3−アリル−4−ヒドロキシフェニル)スルホンを使用して比較用の感熱記録材料を得た。
以上の様にして得られた本発明及び比較用の感熱記録材料について下記の品質性能試験を行った。
【0032】
【0033】
1)地肌 :試料の未発色部をマクベス反射濃度計(RD−914型、マクベス社製)で測定した値(マクベス反射濃度)。
2)発色濃度 :市販のサーマルプリンター(イシダL−2000)で印字した画像部分のマクベス反射濃度。
3)耐熱性 :試料を130℃の熱板で1秒間、押印した後の地肌部分のマクベス反射濃度。
4)耐熱性 :試料を150℃の熱板で1秒間、押印した後の地肌部分のマクベス反射濃度。
5)耐熱性 :試料を170℃の熱板で1秒間、押印した後の地肌部分のマクベス反射濃度。
【0034】
表1から明らかなように本発明の感熱記録材料は印字濃度に優れ、且つ地肌部は130℃以上の熱に対してかぶり、発色が極めて少ない。
【0035】
【発明の効果】
印字濃度に優れ、且つ高温下での耐熱性に優れた感熱記録材料が得られた。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a heat-sensitive recording material, and more particularly to a heat-sensitive recording material having a sufficient print density and excellent heat resistance at high temperatures.
[0002]
[Prior art]
Generally, a thermosensitive recording material is prepared by separately dispersing a developer such as a leuco dye and a phenolic substance into fine particles separately, then mixing the two, and adding additives such as a binder, a sensitizer, a filler, and a lubricant. Is added to form a coating liquid and applied to paper, film, synthetic paper, etc., and one or both of the leuco dye and the developer are melted by heating to obtain a color recording by a chemical reaction caused by contact. . For color development of the heat-sensitive recording sheet, a thermal printer or the like having a built-in thermal head is used. Compared to other recording methods, this thermal recording method is (1) no noise during recording, (2) there is no need for development and fixing, (3) maintenance-free, and (4) machines are relatively inexpensive. It is widely used in the field of facsimile machines, computer output, printers such as calculators, recorders for medical measurement, automatic ticket vending machines, heat-sensitive recording labels, and the like.
[0003]
In recent years, the use of POS systems in retail stores, convenience stores, supermarkets, and the like, and the use of labels, tickets, coupons, and the like associated with automated systems in transportation have become widespread. In these applications, it is desired that the heat-sensitive recording material be further improved in storage stability. For example, there are cards that are heated or thawed at convenience store foods or frozen foods, and cards that are left in a car. The demand for high-speed recording has further increased, and the development of a thermosensitive recording material that can sufficiently cope with high-speed recording has been strongly desired. However, in general, if the sensitivity of the thermosensitive recording material is increased to improve the thermal response, it can be used during production, use, or storage. As a result, the disadvantage that background fogging occurs tends to appear. As another method, a method of providing a specific intermediate layer between the support and the heat-sensitive coloring layer has been studied, but it is insufficient from the viewpoint of processability and economy.
On the other hand, it has been proposed to include a tris (hydroxyphenyl) ethane compound in order to improve heat resistance (for example, see Patent Documents 1 and 2).
[Patent Document 1]
JP-A-6-115255 [Patent Document 2]
JP-A-7-314904
[Problems to be solved by the invention]
It is an object of the present invention to overcome the disadvantages of the prior art. That is, it is an object of the present invention to provide a thermosensitive recording material having a sufficient print density and excellent heat resistance at high temperatures.
[0005]
[Means for Solving the Problems]
The present inventors have made various studies to achieve the above object, and as a result, completed the present invention. That is, the present invention
(1) In a heat-sensitive recording material using a colorless or pale-colored color-forming compound and a color-developing compound capable of coloring the color-forming compound when heated, 3-diethylamino-7- (o-fluoroanilino) is used as the color-forming compound. A) heat-sensitive recording material, characterized by containing fluoran and 1,1,1-tris (p-hydroxyphenyl) ethane as a color-developing compound, respectively.
About.
[0006]
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention will be described in detail. The heat-sensitive recording material of the present invention comprises 3-diethylamino-7- (o-fluoroanilino) fluoran as a color-forming compound, 1,1,1-tris (p-hydroxyphenyl) ethane as a color-developing compound, and A thermosensitive coloring layer is prepared by using a binder as shown below and other fillers, sensitizers, and other additives as necessary.
[0007]
In forming the thermosensitive coloring layer in the present invention, 3-diethylamino-7- (o-fluoroanilino) fluoran is generally used in an amount of 1 to 50% by weight, preferably 5 to 30% by weight, 1,1,1-tris (p). (Hydroxyphenyl) ethane is usually 1 to 60% by weight, preferably 5 to 30%, the binder is usually 1 to 90% by weight, the filler and the sensitizer are each usually 0 to 80% by weight, other lubricants and interfaces The activator, antifoaming agent, ultraviolet absorber and the like are each used in an arbitrary ratio, for example, usually 0 to 30% by weight, respectively (% by weight is the weight ratio of each component in the thermosensitive coloring layer).
[0008]
In a further preferred embodiment, among the above-mentioned compositions, the amount of each used is 1,1,1-tris (p by 3-diethylamino-7- (o-fluoroanilino) fluoran 1 in weight ratio. (-Hydroxyphenyl) ethane is generally used in a weight ratio of 0.5 to 20 times, preferably 1 to 5 times.
Further, in the heat-sensitive recording material of the present invention, a known color-forming compound and a color-developing compound other than the main components of the present invention may be used in combination.
[0009]
Examples of the color-forming compound that can be used in combination in the present invention are not particularly limited as long as they are generally used for pressure-sensitive recording paper or heat-sensitive recording paper. Examples of the coloring compounds that can be used include, for example, fluoran compounds, triarylmethane compounds, spiro compounds, diphenylmethane compounds, thiazine compounds, lactam compounds, fluorene compounds, and the like.
[0010]
Specific examples of the fluoran compound that can be used include, for example, 3-diethylamino-6-methyl-7-anilinofluoran, 3-dibutylamino-6-methyl-7-anilinofluoran, 3- (N-methyl- N-cyclohexylamino) -6-methyl-7-anilinofluoran, 3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilinofluoran, 3- (N-ethyl-N -Isobutylamino) -6-methyl-7-anilinofluoran, 3- [N-ethyl-N- (3-ethoxypropyl) amino] -6-methyl-7-anilinofluoran, 3- (N- Ethyl-N-hexylamino) -6-methyl-7-anilinofluoran, 3-dipentylamino-6-methyl-7-anilinofluoran, 3- (N-methyl-N-propylamino) 6-methyl-7-anilinofluoran, 3- (N-ethyl-N-tetrahydrofurylamino) -6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7- (p-chloroanilino ) Fluoran, 3-diethylamino-6-methyl-7- (p-fluoroanilino) fluoran, 3- [N-ethyl-N- (p-tolyl) amino] -6-methyl-7-anilinofluoran, 3-diethylamino-6-methyl-7- (p-toluidino) fluoran, 3-diethylamino-7- (o-chloroanilino) fluoran, 3-dibutylamino-7- (o-chloroanilino) fluoran, 3-dibutylamino-7 -(O-fluoroanilino) fluoran, 3-diethylamino-7- (3,4-dichloroanilino) fluoran, 3-pyrrolidine -6-methyl-7-anilinofluoran, 3-diethylamino-6-chloro-7-ethoxyethylaminofluoran, 3-diethylamino-6-chloro-7-anilinofluoran, 3-diethylamino-7-chloro Fluoran, 3-diethylamino-7-methylfluoran, 3-diethylamino-7-octylfluoran, 3- [N-ethyl-N- (p-tolyl) amino] -6-methyl-7-phenethylfluoran and the like Is mentioned.
[0011]
Specific examples of the triarylmethane compound that can be used include, for example, 3,3-bis (p-dimethylaminophenyl) -6-dimethylaminophthalide (also known as crystal violet lactone or CVL), 3,3-bis (P-dimethylaminophenyl) phthalide, 3- (p-dimethylaminophenyl) -3- (1,2-dimethylaminoindol-3-yl) phthalide, 3- (p-dimethylaminophenyl) -3- (2 -Methylindol-3-yl) phthalide, 3- (p-dimethylaminophenyl) -3- (2-phenylindol-3-yl) phthalide, 3,3-bis (1,2-dimethylindol-3-yl) ) -5-dimethylaminophthalide, 3,3-bis (1,2-dimethylindol-3-yl) -6-dimethylaminophthalide, , 3-Bis (9-ethylcarbazol-3-yl) -5-dimethylaminophthalide, 3,3- (2-phenylindol-3-yl) -5-dimethylaminophthalide, 3-p-dimethylamino Phenyl-3- (1-methylpyrrol-2-yl) -6-dimethylaminophthalide and the like.
[0012]
Further, specific examples of usable spiro compounds include, for example, 3-methylspirodinaphthopyran, 3-ethylspirodinaphthopyran, 3,3′-dichlorospirodinaphthopyran, 3-benzylspirodinaphthopyran, -Propylspirobenzopyran, 3-methylnaphtho- (3-methoxybenzo) spiropyran, 1,3,3-trimethyl-6-nitro-8'-methoxyspiro (indoline-2,2'-benzopyran) and the like are diphenylmethane-based Specific examples of the compound include, for example, N-halophenyl-leuco auramine, 4,4-bis-dimethylaminophenylbenzhydryl benzyl ether, N-2,4,5-trichlorophenyl leuco auramine and the like are thiazine compounds. Specific examples of benzoyl leucomethylene blue and p-nitroben Illeucomethylene blue and the like are specific examples of lactam compounds, for example, rhodamine B anilinolactam, rhodamine Bp-chloroanilinolactam and the like, and specific examples of fluorene compounds are, for example, 3,6-bis ( Dimethylamino) fluorenespiro (9,3 ′)-6′-dimethylaminophthalide, 3,6-bis (dimethylamino) fluorenespiro (9,3 ′)-6′-pyrrolidinophthalide, 3-dimethylamino -6-diethylaminofluorenespiro (9,3 ')-6'-pyrrolidinophthalide and the like. These coloring compounds are used alone or in combination.
[0013]
In the present invention, the color-developing compound that can be used in combination with 1,1,1-tris (p-hydroxyphenyl) ethane is not particularly limited as long as it is generally used for pressure-sensitive recording paper or heat-sensitive recording paper. It can be used and is not particularly limited. Specific examples include, for example, α-naphthol, β-naphthol, p-octylphenol, 4-t-octylphenol, pt-butylphenol, p-phenylphenol, 1,1-bis (p-hydroxyphenyl) propane, 2, 2-bis (p-hydroxyphenyl) propane (alias: bisphenol A or BPA), 2,2-bis (p-hydroxyphenyl) butane, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane , 1,1-bis (p-hydroxyphenyl) cyclohexane, 4,4'-thiobisphenol, 4,4'-cyclo-hexylidenediphenol, 4,4'-isouropyridenebis (2-t-butylphenol) , 2,2'-methylenebis (4-chlorophenol), 4,4'-dihydroxydiphenylsulfo , 2,4'-dihydroxydiphenylsulfone, bis (3-allyl-4-hydroxyphenyl) sulfone, 4-hydroxy-4'-isopropoxydiphenylsulfone, 4-hydroxy-4'-benzyloxydiphenylsulfone, bis (4 Phenolic compounds such as -hydroxyphenyl) methyl acetate, butyl bis (4-hydroxyphenyl) acetate and benzyl bis (4-hydroxyphenyl) acetate, benzyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, 4-hydroxyphthalate Carboxylic acid derivatives such as dibenzyl acid, dimethyl 4-hydroxyphthalate, ethyl 5-hydroxyisophthalate, 3,5-di-t-butylsalicylic acid, 3,5-di-α-methylbenzylsalicylic acid, and aromatic carboxylic acids Acids or polyvalent metal salts thereof But not limited to these.
[0014]
Examples of the sensitizer (thermally fusible compound) that can be used in the present invention include waxes such as animal and vegetable waxes and synthetic waxes, higher fatty acids, higher fatty acid amides, higher fatty acid anilides, naphthalene derivatives, aromatic ethers, and aromatic ethers. Carboxylic acid derivatives, aromatic sulfonic acid ester derivatives, carbonic acid or oxalic acid diester derivatives, biphenyl derivatives, terphenyl derivatives, urfone derivatives, etc., which are solid at ordinary temperature and have a melting point of about 70 ° C. or more can be used.
[0015]
As waxes, for example, wood wax, carnauba wax, shellac, paraffin, montan wax, oxidized paraffin, polyethylene wax, polyethylene oxide, etc., as higher fatty acids, for example, stearic acid, behenic acid, etc., as higher fatty acid amides, For example, stearic acid amide, oleic acid amide, N-methylstearic acid amide, erucic acid amide, methylolbehenic acid amide, methylenebisstearic acid amide, ethylenebisstearic acid amide, etc. Linoleic acid anilide and the like, naphthalene derivatives such as 1-benzyloxynaphthalene, 2-benzyloxynaphthalene and 1-hydroxynaphthoic acid phenyl ester, and aromatic ethers such as 1,2 Diphenoxyethane, 1,4-diphenoxybutane, 1,2-bis (3-methylphenoxy) ethane, 1,2-bis (4-methoxyphenoxy) ethane, 1,2-bis (3,4-dimethylphenyl) ) Ethane, 1-phenoxy-2- (4-chlorophenoxy) ethane, 1-phenoxy-2- (4-methoxyphenoxy) ethane, 1,2-diphenoxymethylbenzene, etc., as aromatic carboxylic acid derivatives, For example, p-hydroxybenzoic acid benzyl ester, p-benzyloxybenzoic acid benzyl ester, terephthalic acid dibenzyl ester and the like, and as aromatic sulfonic acid ester derivatives, for example, p-toluenesulfonic acid phenyl ester, phenyl mesitylene sulfonate, -Methylphenyl mesitylene sulfonate or the like Examples of the diester oxalate include diphenyl carbonate, dibenzyl oxalate, di (4-chlorobenzyl) oxalate, and di (4-methylbenzyl) oxalate. Examples of the biphenyl derivative include p-benzyl. Examples of biphenyl and p-allyloxybuphenyl are terphenyl derivatives, for example, m-terphenyl, and examples of sulfone derivatives are, for example, diphenyl sulfone.
[0016]
The amount of the color-forming compound and the color-developing compound that can be used in combination can be in a range that does not impair the effects of the present invention, for example, 3-diethylamino-7- (o-fluoroanilino) fluoran, 1,1,1-tris. A ratio in a range not exceeding the amount of (p-hydroxyphenyl) ethane used is preferred.
[0017]
Specific examples of the binder that can be used include, for example, methyl cellulose, methoxy cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, cellulose, polyvinyl alcohol (PVA), carboxyl group-modified polyvinyl alcohol, sulfonic acid group-modified polyvinyl alcohol, polyvinyl pyrrolidone, Polyacrylamide, polyacrylic acid, starch and derivatives thereof, casein, gelatin, water-soluble isoprene rubber, alkali salt of styrene / maleic anhydride copolymer, alkali salt of iso (or diiso) butylene / maleic anhydride copolymer, etc. Water-soluble or polyvinyl acetate, vinyl chloride / vinyl acetate copolymer, polystyrene, polyacrylate, polyurethane, styrene / butadiene ( B) copolymers, carboxylated styrene / butadiene (SB) copolymer, styrene / butadiene / acrylic acid copolymer, colloidal silica and the like hydrophobic polymer emulsion such as composite particles of the acrylic resin is used.
[0018]
Specific examples of the filler that can be used include, for example, calcium carbonate, magnesium carbonate, magnesium oxide, silica, white carbon, talc, clay, alumina, magnesium hydroxide, aluminum hydroxide, aluminum oxide, barium sulfate, polystyrene resin, urea- Formalin resin and the like can be mentioned.
[0019]
Further, in the present invention, various additives other than those described above can be used. Examples of other additives that can be used include, for example, thermal head wear prevention, zinc stearate for the purpose of preventing sticking, and the like. Higher fatty acid metal salts such as calcium stearate, phenol derivatives for imparting an antioxidant or antiaging effect, ultraviolet absorbers such as benzophenone compounds, benzotriazole compounds, various surfactants, defoamers, etc. No.
[0020]
The heat-sensitive recording material of the present invention is prepared by using the above-mentioned material by the following method, for example. That is, first, 3-diethylamino-7- (o-fluoroanilino) fluoran and 1,1,1-tris (p-hydroxyphenyl) ethane are separately added to a binder or other additives as necessary by a conventional method. After pulverizing and dispersing with a dispersing machine such as a ball mill, an attritor, a sand mill and the like (when pulverizing and dispersing are performed by a wet method, usually water is used as a medium), they are mixed to prepare a coating solution for the thermosensitive coloring layer. The heat-sensitive recording material of the present invention is obtained by coating and drying on a support such as plastic sheet, synthetic paper or the like by a bar coater, a blade coater or the like so that the dry weight is usually 1 to 20 g / m 2 . If necessary, an intermediate layer may be provided between the thermosensitive coloring layer and the support, or an overcoat layer (protective layer) may be provided on the thermosensitive coloring layer. The intermediate layer and the overcoat layer (protective layer) are pulverized and dispersed in the same manner as in the preparation of the thermosensitive coloring layer coating solution together with, for example, the above-mentioned binder or other additives as necessary, to form the intermediate layer coating solution or After forming an overcoat layer (protective layer) coating solution, the solution is applied by drying so as to have a weight of usually about 0.1 to 5 g / m 2 and dried.
[0021]
The heat-sensitive recording material of the present invention containing 3-diethylamino-7- (o-fluoroanilino) fluoran and 1,1,1-tris (p-hydroxyphenyl) ethane has excellent print density as compared with conventionally known materials. And excellent heat resistance at high temperatures.
[0022]
【Example】
The present invention will be described more specifically with reference to examples, but the present invention is not limited thereto. In the examples, "parts" indicates parts by weight and "%" indicates% by weight.
[0023]
Example 1
(Formation of thermosensitive coloring layer)
A mixture having the following composition was pulverized and dispersed using a sand grinder so that the average particle size became 1 μm or less, to prepare Solution [A] and Solution [B], respectively.
[A] solution: 3-diethylamino-7- (o-fluoroanilino) fluoran 25 parts 25% aqueous solution of PVA 20 parts water 55 parts [B] solution: 1,1,1-tris (p-hydroxyphenyl) ethane 25 Part 25% PVA aqueous solution 20 parts water 55 parts
Next, the respective liquids obtained above and the following agents were mixed in the following proportions to prepare a coating solution for the thermosensitive coloring layer, and dried on a 188 μm-thick white polyester film (Lumirror E22, manufactured by Toray Industries, Inc.). Was applied to a weight of 10 g / m 2 and dried to form a thermosensitive coloring layer.
[A] solution 8 parts [B] solution 20 parts 50% aqueous calcium carbonate dispersion 10 parts 50% carboxylated SB copolymer emulsion 6 parts
(Formation of protective layer)
Next, a mixture having the following composition was prepared to form a coating liquid for the protective layer, and the composition was coated on the thermosensitive coloring layer so that the weight when dried was 3 g / m 2, and dried to form a thermosensitive recording material of the present invention having a protective layer. Got.
40% styrene / acrylic ester copolymer emulsion 17 parts 5% Bentonite aqueous dispersion 30 parts 30% zinc stearate aqueous dispersion 4 parts
Example 2
The mixture having the following composition was pulverized and dispersed using a sand grinder so that the average particle diameter became 1 μm or less, to prepare a liquid [C].
[C] liquid: 25 parts of 3-dibutylamino-6-methyl-7-anilinofluoran 25 parts of a 25% PVA aqueous solution 20 parts of water 55 parts
Next, the respective liquids obtained above and the following agents were mixed in the following proportions to prepare a coating solution for the thermosensitive coloring layer, and dried on a 188 μm-thick white polyester film (Lumirror E22, manufactured by Toray Industries, Inc.). Was applied to a weight of 10 g / m 2 and dried to form a thermosensitive coloring layer.
[A] solution 6 parts [B] solution 20 parts [C] solution 2 parts 50% aqueous calcium carbonate dispersion 10 parts 50% carboxylated SB copolymer emulsion 6 parts (formation of protective layer)
Further, a protective layer was provided in the same manner as in Example 1 to obtain a thermosensitive recording material of the present invention having a protective layer.
[0028]
Example 3
Using a sand grinder, a mixture having the following composition was pulverized and dispersed so as to have a mean particle diameter of 1 μm or less to prepare a liquid [D].
[0029]
Next, the respective liquids obtained above and the following agents were mixed in the following proportions to prepare a coating solution for the thermosensitive coloring layer, and dried on a 188 μm-thick white polyester film (Lumirror E22, manufactured by Toray Industries, Inc.). Was applied to a weight of 10 g / m 2 and dried to form a thermosensitive coloring layer.
[A] solution 8 parts [B] solution 16 parts [D] solution 4 parts 50% aqueous calcium carbonate dispersion 10 parts 50% carboxylated SB copolymer emulsion 6 parts (formation of protective layer)
Further, a protective layer was provided in the same manner as in Example 1 to obtain a thermosensitive recording material of the present invention having a protective layer.
[0030]
Comparative Example 1
3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilinofluoran instead of 3-diethylamino-7- (o-fluoroanilino) fluoran in solution [A] of Example 1 Was used to obtain a heat-sensitive recording material for comparison.
[0031]
Comparative Example 2
A heat-sensitive recording material for comparison was obtained by using bis (3-allyl-4-hydroxyphenyl) sulfone instead of 1,1,1-tris (p-hydroxyphenyl) ethane in the solution [B] of Example 1. Was.
The following quality performance tests were performed on the present invention and the comparative thermosensitive recording material obtained as described above.
[0032]
[0033]
1) Background: The value (Macbeth reflection density) obtained by measuring the uncolored portion of the sample with a Macbeth reflection densitometer (RD-914, manufactured by Macbeth).
2) Color density: Macbeth reflection density of an image portion printed by a commercially available thermal printer (Isida L-2000).
3) Heat resistance: Macbeth reflection density of the background after imprinting the sample on a hot plate at 130 ° C. for 1 second.
4) Heat resistance: Macbeth reflection density of the background after stamping the sample with a hot plate at 150 ° C. for 1 second.
5) Heat resistance: Macbeth reflection density of the background after stamping the sample with a hot plate at 170 ° C. for 1 second.
[0034]
As is evident from Table 1, the heat-sensitive recording material of the present invention has excellent print density, and the background portion fogs against heat of 130 ° C. or more and has very little color development.
[0035]
【The invention's effect】
A heat-sensitive recording material having excellent printing density and excellent heat resistance at high temperatures was obtained.
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Cited By (2)
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JP2020151930A (en) * | 2019-03-20 | 2020-09-24 | 株式会社リコー | Heat-sensitive recording material, heat-sensitive recording method, heat-sensitive recording device, and heat-sensitive recording medium |
WO2022101297A1 (en) * | 2020-11-10 | 2022-05-19 | Datalase Ltd. | A composition |
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JP2020151930A (en) * | 2019-03-20 | 2020-09-24 | 株式会社リコー | Heat-sensitive recording material, heat-sensitive recording method, heat-sensitive recording device, and heat-sensitive recording medium |
JP7302214B2 (en) | 2019-03-20 | 2023-07-04 | 株式会社リコー | Thermal recording material, thermal recording method, thermal recording apparatus, and thermal recording medium |
WO2022101297A1 (en) * | 2020-11-10 | 2022-05-19 | Datalase Ltd. | A composition |
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