JPH0336032B2 - - Google Patents
Info
- Publication number
- JPH0336032B2 JPH0336032B2 JP59074673A JP7467384A JPH0336032B2 JP H0336032 B2 JPH0336032 B2 JP H0336032B2 JP 59074673 A JP59074673 A JP 59074673A JP 7467384 A JP7467384 A JP 7467384A JP H0336032 B2 JPH0336032 B2 JP H0336032B2
- Authority
- JP
- Japan
- Prior art keywords
- heat
- sensitive recording
- color
- isobenzofuranone
- recording sheet
- 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 - Lifetime
Links
- 239000002243 precursor Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 description 12
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- BGOZIOZETMDSAQ-UHFFFAOYSA-N 3-phenoxy-3h-2-benzofuran-1-one Chemical compound C12=CC=CC=C2C(=O)OC1OC1=CC=CC=C1 BGOZIOZETMDSAQ-UHFFFAOYSA-N 0.000 description 6
- -1 3-(4- methoxyphenoxy)-1(3H)-isobenzofuranone Chemical compound 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 4
- 230000035945 sensitivity 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 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000004043 responsiveness Effects 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 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 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000001993 wax Substances 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- WCOXQTXVACYMLM-UHFFFAOYSA-N 2,3-bis(12-hydroxyoctadecanoyloxy)propyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC(O)CCCCCC)COC(=O)CCCCCCCCCCC(O)CCCCCC WCOXQTXVACYMLM-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
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-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
- MIGWFMQADOWYBI-UHFFFAOYSA-N 3-(4-methylphenoxy)-3h-2-benzofuran-1-one Chemical compound C1=CC(C)=CC=C1OC1C2=CC=CC=C2C(=O)O1 MIGWFMQADOWYBI-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 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
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 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
- 239000011888 foil Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex 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
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 1
- 150000005209 naphthoic acids Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000001454 recorded image Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 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
- B41M5/26—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
- B41M5/337—Additives; Binders
- B41M5/3375—Non-macromolecular compounds
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)
Description
本発明は感熱記録材料に関し、特に発色性を向
上させた感熱記録材料に関する。
感熱記録材料は一般に支持体上に電子供与性の
通常無色ないし淡色の染料前駆体と電子受容性の
顕色剤とを主成分とする感熱記録層を設けたもの
で、熱ヘツド、熱ペン、レーザー光等で加熱する
ことにより染料前駆体と顕色剤とが瞬時反応し、
記録画像が得られるもので、特公昭43−4160号、
特公昭45−14039号公報等に開示されている。こ
のような感熱記録材料は比較的簡単な装置で記録
が得られ、保守が容易であること、騒音の発生が
ないことなどの利点があり、計測用記録計、フア
クシミリ、プリンター、コンピユーターの端末
機、ラベル、乗車券等自動券売機など広範囲の分
野に利用されている。特にフアクシミリにおいて
は感熱方式の需要が大巾に伸びてきているうえ
に、送信コスト低減のために高速化されつつあ
る。この様なフアクシミリの高速化に対応して感
熱記録材料の高感度化が求められるようになつて
きた。
高速化されたフアクシミリはA4の標準原稿を
10秒から20秒で受送信するためフアクシミリのサ
ーマルヘツドに流れる電流も数ミリ秒以下という
非常に短い時間の繰返しであり、それによつて発
生した熱エネルギーを感熱記録シートへ伝達し画
像形成反応を行なわしめるものである。
この様に短時間に伝達された熱エネルギーで画
像形成反応を行なうには、熱応答性に優れた感熱
記録材料である事が必要である。熱応答性を上げ
る為には顕色剤と染料前駆体との相溶性を向上さ
せねばならない。これには必要に応じて増感剤が
使用される。増感剤は、伝達された熱エネルギー
によりそれ自身が融解する際に、近傍の染料前駆
体及び顕色剤を溶解ないしは内包して発色反応を
促進させる働きを有する為、増感剤の熱応答性な
いしは染料前駆体、顕色剤に対する相溶性を向上
せしめる事も感熱記録材料を高感度化する１つの
方法である。
この様な方法として、特開昭48−19231号公報
にはワツクス類を、特開昭49−34842号、特開昭
50−149353号、特開昭52−106746号、特開昭53−
5636号公報等には、含窒素化合物、カルボン酸エ
ステル等を、特開昭57−64593号、特開昭58−
87094号公報にはナフトール誘導体を、特開昭57
−64592号、特開昭57−185187号、特開昭57−
191089号、特開昭58−110289号公報にはナフトエ
酸誘導体を添加する事が開示されている。
しかし、これらの方法を使用して製造した感熱
記録材料は発色濃度及び発色感度の点でなお不十
分なものである。
本発明者らは、さらに高感度の感熱記録材料を
得るため種々の増感剤を検討した結果、通常無色
ないし淡色と染料前駆体と加熱時反応して該染料
前駆体を発色せしめる顕色剤を含有する感熱記録
材において、増感剤として下記一般式で示される
化合物を含有することにより、熱応答性に優れた
高感度の感熱記録シートを得ることができた。
一般式
The present invention relates to a heat-sensitive recording material, and particularly to a heat-sensitive recording material with improved color development. A heat-sensitive recording material generally has a heat-sensitive recording layer on a support, the main components of which are an electron-donating, usually colorless or light-colored dye precursor and an electron-accepting developer. By heating with laser light, etc., the dye precursor and developer react instantly,
This allows recorded images to be obtained, and is designated as Special Publication No. 43-4160.
It is disclosed in Japanese Patent Publication No. 14039/1983. These heat-sensitive recording materials have the advantages of being able to record with relatively simple equipment, being easy to maintain, and producing no noise. It is used in a wide range of fields, including automatic ticket vending machines, labels, and train tickets. Particularly in facsimile, the demand for heat-sensitive methods is increasing rapidly, and speeds are being increased to reduce transmission costs. In response to such increased speed of facsimile, there has been a demand for higher sensitivity of heat-sensitive recording materials. High-speed facsimile can print standard A4 documents.
Because the facsimile's thermal head receives and transmits data in 10 to 20 seconds, the current that flows through the facsimile's thermal head is repeated over a very short period of time, less than a few milliseconds, and the generated thermal energy is transferred to the thermosensitive recording sheet, causing an image-forming reaction. It is something to be done. In order to carry out an image forming reaction using thermal energy transmitted in such a short time, it is necessary to use a heat-sensitive recording material with excellent thermal responsiveness. In order to improve thermal responsiveness, it is necessary to improve the compatibility between the color developer and the dye precursor. A sensitizer is used for this purpose if necessary. When the sensitizer melts due to the transferred thermal energy, it has the function of dissolving or encapsulating the nearby dye precursor and color developer and promoting the color reaction, so the thermal response of the sensitizer is One way to make heat-sensitive recording materials highly sensitive is to improve their compatibility with dye precursors and color developers. As such a method, waxes are used in JP-A-48-19231, JP-A-49-34842 and JP-A-Sho.
No. 50-149353, JP-A-52-106746, JP-A-53-
5636, etc., nitrogen-containing compounds, carboxylic acid esters, etc. are described in JP-A-57-64593, JP-A-58-
No. 87094 discloses naphthol derivatives,
-64592, JP-A-57-185187, JP-A-57-
No. 191089 and JP-A-58-110289 disclose the addition of naphthoic acid derivatives. However, the heat-sensitive recording materials produced using these methods are still unsatisfactory in terms of color density and color sensitivity. The present inventors investigated various sensitizers in order to obtain a heat-sensitive recording material with even higher sensitivity. As a result, the present inventors found that a color developer that is usually colorless or light in color and reacts with a dye precursor when heated to cause the dye precursor to develop a color. By containing a compound represented by the following general formula as a sensitizer in the heat-sensitive recording material containing the following, a highly sensitive heat-sensitive recording sheet with excellent heat responsiveness could be obtained. general formula
【式】
（但し、Ｒはフエニル基あるいは置換フエニル基
を示す）
一般式で示される化合物としては、３−フエノ
キシ−１（3H）−イソベンゾフラノン、３−（４−
メトキシフエノキシ）−１（3H）−イソベンゾフラ
ノン、３−（３−タ−シヤリ−ブチル−４−ヒド
ロキシ）−１（3H）−イソベンゾフラノン、３−
（４−メチルフエノキシ）−１（3H）−イソベンゾ
フラノンなどが挙げられる。
本発明による増感剤は通常顕色剤に対して５重
量％以上添加される。好ましい量は10〜400重量
％であり、特に20〜300重量％が好ましい。添加
量が５重量％未満では感度向上効果が十分でな
く、400重量％より多い添加では、かえつて稀釈
効果のために発色濃度が低くなる。
本発明の感熱記録材料に用いられる主な成分を
以下に具体的に説明するが、本発明において以下
に述べられたもの以外のものも用いられることは
もちろんである。
染料前駆体としては、トリフエニルメタン系、
フルオラン系、ジフエニルメタン系、チアジン
系、スピロピラン系化合物などが挙げられる。例
えば、クリスタルバイオレツトラクトン、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−６−クロロ−７−メチルフルオラ
ン、３−ジエチルアミノ−６−メチル−７−クロ
ロフルオラン、３−ジエチルアミノ−７−アニリ
ノフルオラン、３−ジエチルアミノ−７−（２−
クロロアニリノ）フルオラン、３−ジブチルアミ
ノ−７−（２−クロロアニリノ）フルオラン、３
−ジエチルアミノ−７−（３−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−アニリノフルオラン、３−（Ｎ−エチル−ｐ
−トルイジノ）−６−メチル−７−アニリノフル
オラン、３−（Ｎ−メチルシクロヘキシルアミノ）
−３−メチル−７−アニリノフルオラン、３−ピ
ペリジノ−３−メチル−７−アニリノフルオラン
等がある。
顕色剤としては、一般に感熱紙に使用される酸
性物質が使用でき、例えば、フエノール、ｐ−ｔ
−ブチルフエノール、ｐ−フエニルフエノール、
ナフトール、ｐ−ヒドロキシアセトフエノン、
２，2′−ジヒドロキシジフエノール、４，4′−イ
ソプロピリデン（２−ｔ−ブチルフエノール）、
４，4′−イソプロピリデンジフエノール、４，
4′−シクロヘキシリデンジフエノール、ノボラツ
ク型フエノール樹脂、安息香酸、ｐ−ｔ−ブチル
安息香酸、ｐ−ヒドロキシ安息香酸、ｐ−ヒドロ
キシ安息香酸ベンジルエステル、ｐ−ヒドロキシ
安息香酸メチルエステルなどが挙げられる。
バインダーとしては、デンプン類、ヒドロキシ
エチルセルロース、メチルセルロース、カルボキ
シメチルセルロース、ゼラチン、カゼイン、ポリ
ビニルアルコール、変性ポリビニルアルコール、
スチレン−無水マレイン酸共重合体、エチレン−
無水マレイン酸共重合体などの水溶性バインダ
ー、スチレン−ブタジエン共重合体、アクリロニ
トリル−ブタジエン共重合体、アクリル酸メチル
−ブタジエン共重合体などのラテツクス系水不溶
性バインダーなどが挙げられる。
顔料としては、ケイソウ土、タルク、カオリ
ン、焼成カオリン、炭酸カルシウム、炭酸マグネ
シウム、酸化チタン、酸化亜鉛、酸化ケイ素、水
酸化アルミニウム、尿素−ホルマリン樹脂などが
挙げられる。
その他に、ヘツド摩耗防止、ステイツキング防
止などの目的でステアリン酸亜鉛、ステアリン酸
カルシウム等の高級脂肪酸金属塩、パラフイン、
酸化パラフイン、ポリエチレン、酸化ポリエチレ
ン、ステアリン酸アミド、カスターワツクス等の
ワツクス類を、また、ジオクチルスルホコハク酸
ナトリウム等の分散剤、ベンゾフエノン系、ベン
ゾトリアゾール系などの紫外線吸収剤、さらに界
面活性剤、螢光染料などが挙げられる。
本発明による感熱記録材に用いられる支持体と
しては紙が主として用いられるが、各種不織布、
プラスチツクフイルム、合成紙、金属箔等あるい
はこれらを組合わせた複合シートを任意に用いる
ことができる。
以下、実施例を示し、本発明を更に詳細に説明
するが、本発明はこれらの実施例のみに限定され
るものではない。
実施例 １
３−ジエチルアミノ−６−メチル−７−アニリ
ノフルオラン10ｇを２％ポリビニルアルコール水
溶液と共にボールミルで24時間分散した。一方、
２，２−ビス（４−ヒドロキシフエニル）プロパ
ン25ｇを２％ポリビニルアルコール水溶液75ｇと
共にボールミルで24時間分散し、さらに３−フエ
ノキシ−１（3H）−イソベンゾフラノン10ｇを２
％ポリビニルアルコール水溶液30ｇと共にボール
ミルで24時間分散した。これら３種の分散液を混
合した後、炭酸カルシウムの50％分散液80ｇを加
え、さらにステアリン酸亜鉛の20％分散液25ｇ、
10％ポリビニルアルコール水溶液180ｇ、水75ｇ
を加え十分撹拌して塗液とした。
塗液を秤量55ｇ／m2の原紙に固型分塗布量が６
ｇ／m2となるように塗布乾燥し、スーパーカレン
ダーで処理して感熱記録シートを得た。
実施例 ２
実施例１の３−フエノキシ−１（3H）−イソベ
ンゾフラノンのかわりに、３（３−タ−シヤリ−
ブチル−４−ヒドロキシフエノキシ）−１（3H）
イソベンゾフラノンを用いた以外は実施例１と同
様にして感熱記録シートを得た。
実施例 ３
実施例１の３−フエノキシ−１（3H）−イソベ
ンゾフラノンのかわりに、３（４−メトキシフエ
ノキシ）−１（3H）−イソベンゾフラノンを用いた
以外は実施例１と同様にして感熱記録シートを得
た。
比較例 １
実施例１の３−フエノキシ−１（3H）−イソベ
ンゾフラノンを除いた以外は実施例１と同様にし
て感熱記録シートを得た。
比較例 ２
実施例１の３−フエノキシ−１（3H）−イソベ
ンゾフラノンのかわりにＮ−ヒドロキシメチルス
テアリン酸アミドを用いた以外は実施例１と同様
にして感熱記録シートを得た。
実施例１〜３及び比較例１、２で得た感熱記録
シートについて以下に記す試験を行ない評価し
た。
試 験
感熱フアクシミリ試験機〔松下電子部品(株)製〕
を用いて印加パルス巾1.0、1.5、2.0ミリ秒、印加
電圧16.00ボルトの条件でそれぞれ印字し、得ら
れた発色画像の発色濃度をマクべス濃度計
RD514を用いて測定した。
結果を表１に示した。[Formula] (However, R represents a phenyl group or a substituted phenyl group) Compounds represented by the general formula include 3-phenoxy-1(3H)-isobenzofuranone, 3-(4-
methoxyphenoxy)-1(3H)-isobenzofuranone, 3-(3-tert-butyl-4-hydroxy)-1(3H)-isobenzofuranone, 3-
Examples include (4-methylphenoxy)-1(3H)-isobenzofuranone. The sensitizer according to the present invention is usually added in an amount of 5% by weight or more based on the color developer. Preferred amounts are 10-400% by weight, particularly 20-300% by weight. If the amount added is less than 5% by weight, the effect of improving sensitivity will not be sufficient, and if the amount added is more than 400% by weight, the color density will be lowered due to the dilution effect. The main components used in the heat-sensitive recording material of the present invention will be specifically explained below, but it goes without saying that components other than those described below may also be used in the present invention. As a dye precursor, triphenylmethane type,
Examples include fluoran-based, diphenylmethane-based, thiazine-based, and spiropyran-based compounds. For example, crystal violet lactone, 3-diethylamino-7-methylfluorane, 3-diethylamino-6-chloro-7-methylfluorane, 3-diethylamino-6-methyl-7-chlorofluorane, 3-diethylamino-7 -anilinofluorane, 3-diethylamino-7-(2-
chloroanilino)fluoran, 3-dibutylamino-7-(2-chloroanilino)fluoran, 3
-diethylamino-7-(3-chloroanilino)
Fluoran, 3-diethylamino-6-methyl-
7-anilinofluorane, 3-(N-ethyl-p
-toluidino)-6-methyl-7-anilinofluorane, 3-(N-methylcyclohexylamino)
-3-methyl-7-anilinofluorane, 3-piperidino-3-methyl-7-anilinofluorane, and the like. As the color developer, acidic substances generally used for thermal paper can be used, such as phenol, p-t
-butylphenol, p-phenylphenol,
naphthol, p-hydroxyacetophenone,
2,2'-dihydroxydiphenol, 4,4'-isopropylidene (2-t-butylphenol),
4,4'-isopropylidenediphenol, 4,
Examples include 4'-cyclohexylidene diphenol, novolac type phenolic resin, benzoic acid, pt-butylbenzoic acid, p-hydroxybenzoic acid, p-hydroxybenzoic acid benzyl ester, p-hydroxybenzoic acid methyl ester, and the like. As binders, starches, hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, gelatin, casein, polyvinyl alcohol, modified polyvinyl alcohol,
Styrene-maleic anhydride copolymer, ethylene-
Examples include water-soluble binders such as maleic anhydride copolymers, and latex-based water-insoluble binders such as styrene-butadiene copolymers, acrylonitrile-butadiene copolymers, and methyl acrylate-butadiene copolymers. Examples of pigments include diatomaceous earth, talc, kaolin, calcined kaolin, calcium carbonate, magnesium carbonate, titanium oxide, zinc oxide, silicon oxide, aluminum hydroxide, urea-formalin resin, and the like. In addition, higher fatty acid metal salts such as zinc stearate and calcium stearate, paraffin,
Waxes such as paraffin oxide, polyethylene, polyethylene oxide, stearamide, and castor wax, dispersants such as sodium dioctyl sulfosuccinate, ultraviolet absorbers such as benzophenone and benzotriazole, and surfactants and fireflies. Examples include photodyes. Paper is mainly used as the support for the heat-sensitive recording material according to the present invention, but various non-woven fabrics,
Plastic film, synthetic paper, metal foil, etc., or a composite sheet made of a combination of these may be used as desired. EXAMPLES Hereinafter, the present invention will be explained in more detail by way of Examples, but the present invention is not limited to these Examples. Example 1 10 g of 3-diethylamino-6-methyl-7-anilinofluorane was dispersed with a 2% aqueous polyvinyl alcohol solution in a ball mill for 24 hours. on the other hand,
25 g of 2,2-bis(4-hydroxyphenyl)propane was dispersed with 75 g of a 2% polyvinyl alcohol aqueous solution for 24 hours in a ball mill, and further 10 g of 3-phenoxy-1(3H)-isobenzofuranone was dispersed with 2% polyvinyl alcohol aqueous solution.
% polyvinyl alcohol aqueous solution for 24 hours using a ball mill. After mixing these three types of dispersions, 80 g of a 50% dispersion of calcium carbonate was added, and further 25 g of a 20% dispersion of zinc stearate,
180g of 10% polyvinyl alcohol aqueous solution, 75g of water
was added and thoroughly stirred to prepare a coating liquid. The coating liquid was applied to a base paper weighing 55 g/m 2 with a solid content coating amount of 6.
It was coated and dried to give a coating weight of g/m 2 , and treated with a supercalender to obtain a heat-sensitive recording sheet. Example 2 Instead of 3-phenoxy-1(3H)-isobenzofuranone in Example 1, 3(3-tertiary-
Butyl-4-hydroxyphenoxy)-1(3H)
A thermosensitive recording sheet was obtained in the same manner as in Example 1 except that isobenzofuranone was used. Example 3 Same as Example 1 except that 3(4-methoxyphenoxy)-1(3H)-isobenzofuranone was used instead of 3-phenoxy-1(3H)-isobenzofuranone in Example 1. A thermosensitive recording sheet was obtained in the same manner. Comparative Example 1 A thermosensitive recording sheet was obtained in the same manner as in Example 1 except that 3-phenoxy-1(3H)-isobenzofuranone in Example 1 was removed. Comparative Example 2 A thermosensitive recording sheet was obtained in the same manner as in Example 1 except that N-hydroxymethylstearamide was used in place of 3-phenoxy-1(3H)-isobenzofuranone. The heat-sensitive recording sheets obtained in Examples 1 to 3 and Comparative Examples 1 and 2 were evaluated by conducting the following tests. Test Heat-sensitive facsimile tester [manufactured by Matsushita Electronic Components Co., Ltd.]
Printing was performed using a Macbeth densitometer to print under the conditions of applied pulse widths of 1.0, 1.5, and 2.0 milliseconds and applied voltage of 16.00 volts.
Measured using RD514. The results are shown in Table 1.
【表】
表１より、本発明による感熱記録シートは、低
エネルギーでも十分な発色濃度が得られることが
わかる。[Table] Table 1 shows that the heat-sensitive recording sheet according to the present invention can obtain sufficient color density even at low energy.
Claims (1)
反応して該染料前駆体を発色せしめる顕色剤を含
有する感熱記録シートにおいて、下記一般式で示
される化合物を使用する事を特徴とする感熱記録
シート。 一般式 （式中、Ｒはフエニル基あるいは置換フエニル基
を示す）。[Claims] 1. Use of a compound represented by the following general formula in a heat-sensitive recording sheet containing a color developer that reacts with a normally colorless or light-colored dye precursor upon heating to cause the dye precursor to develop color. A heat-sensitive recording sheet featuring: general formula (In the formula, R represents a phenyl group or a substituted phenyl group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59074673A JPS60217195A (en) | 1984-04-12 | 1984-04-12 | Thermal recording sheet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59074673A JPS60217195A (en) | 1984-04-12 | 1984-04-12 | Thermal recording sheet |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60217195A JPS60217195A (en) | 1985-10-30 |
| JPH0336032B2 true JPH0336032B2 (en) | 1991-05-30 |
Family
ID=13553976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59074673A Granted JPS60217195A (en) | 1984-04-12 | 1984-04-12 | Thermal recording sheet |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60217195A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150051991A (en) * | 2012-07-20 | 2015-05-13 | 스텔렌보쉬 유니버시티 | A furanone containing polymer compound with bacteria-adhesion properties |
-
1984
- 1984-04-12 JP JP59074673A patent/JPS60217195A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60217195A (en) | 1985-10-30 |
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