JP2016068418A - Heat-sensitive recording material - Google Patents
Heat-sensitive recording material Download PDFInfo
- Publication number
- JP2016068418A JP2016068418A JP2014200699A JP2014200699A JP2016068418A JP 2016068418 A JP2016068418 A JP 2016068418A JP 2014200699 A JP2014200699 A JP 2014200699A JP 2014200699 A JP2014200699 A JP 2014200699A JP 2016068418 A JP2016068418 A JP 2016068418A
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- JP
- Japan
- Prior art keywords
- sensitive recording
- parts
- heat
- derivatives
- bis
- Prior art date
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- Pending
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- 239000000463 material Substances 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 239000012170 montan wax Substances 0.000 description 1
- ACHJPOGULIRUJQ-UHFFFAOYSA-N n,n'-bis(2-aminophenyl)propanediamide Chemical compound NC1=CC=CC=C1NC(=O)CC(=O)NC1=CC=CC=C1N ACHJPOGULIRUJQ-UHFFFAOYSA-N 0.000 description 1
- PLYOBKOGKORFMB-UHFFFAOYSA-N n,n'-bis[3-(trifluoromethyl)phenyl]propanediamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)CC(=O)NC=2C=C(C=CC=2)C(F)(F)F)=C1 PLYOBKOGKORFMB-UHFFFAOYSA-N 0.000 description 1
- YYAQOJILQOVUSK-UHFFFAOYSA-N n,n'-diphenylpropanediamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)NC1=CC=CC=C1 YYAQOJILQOVUSK-UHFFFAOYSA-N 0.000 description 1
- DLKDXCZRLIQWMN-UHFFFAOYSA-N n,n-diethyl-7-fluorooctan-3-amine Chemical compound CCN(CC)C(CC)CCCC(C)F DLKDXCZRLIQWMN-UHFFFAOYSA-N 0.000 description 1
- GOEWZPICEGNTPR-UHFFFAOYSA-N n-(2-chlorophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1Cl GOEWZPICEGNTPR-UHFFFAOYSA-N 0.000 description 1
- CWBLFCFUSMBFSO-UHFFFAOYSA-N n-(3-nitrophenyl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 CWBLFCFUSMBFSO-UHFFFAOYSA-N 0.000 description 1
- MJUHDEYUFJKWTI-UHFFFAOYSA-N n-(4-methyl-2-nitrophenyl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1NS(=O)(=O)C1=CC=CC=C1 MJUHDEYUFJKWTI-UHFFFAOYSA-N 0.000 description 1
- UOPLDEWGEPWRMH-UHFFFAOYSA-N n-(4-methylphenyl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1NS(=O)(=O)C1=CC=CC=C1 UOPLDEWGEPWRMH-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- HNUFCQUTJXHEPI-UHFFFAOYSA-N n-methyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC HNUFCQUTJXHEPI-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 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
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WMIWKXQBBHIBDO-UHFFFAOYSA-N phenyl 1-hydroxy-2h-naphthalene-1-carboxylate Chemical compound C1C=CC2=CC=CC=C2C1(O)C(=O)OC1=CC=CC=C1 WMIWKXQBBHIBDO-UHFFFAOYSA-N 0.000 description 1
- BBTGZLICINVWQG-UHFFFAOYSA-N phenyl 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)OC1=CC=CC=C1 BBTGZLICINVWQG-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 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
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- ZHROMWXOTYBIMF-UHFFFAOYSA-M sodium;1,3,7,9-tetratert-butyl-11-oxido-5h-benzo[d][1,3,2]benzodioxaphosphocine 11-oxide Chemical compound [Na+].C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP([O-])(=O)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C ZHROMWXOTYBIMF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229940045136 urea Drugs 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000002023 wood 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
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—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)
Abstract
Description
本発明は、発色性に優れた感熱記録材料に関するものである。 The present invention relates to a heat-sensitive recording material having excellent color developability.
感熱記録材料は、一般にロイコ染料とフェノール性化合物等の顕色剤とをそれぞれ別個に微粒子状に分散化した後、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得られた塗工液を、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。このような感熱記録材料の発色のためには、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と比較して、（１）記録時に騒音が出ない、（２）現像、定着の必要がない、（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、電卓などのプリンター分野、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。 In general, heat-sensitive recording materials are obtained by dispersing a leuco dye and a developer such as a phenolic compound separately into fine particles, and then mixing both of them together, such as a binder, a sensitizer, a filler, and a lubricant. A coating solution obtained by adding additives is applied to paper, film, synthetic paper, etc., and develops color by chemical reaction that occurs when one or both of leuco dye and developer are melted and contacted by heating. Get a record. For the color development of such a heat-sensitive recording material, a thermal printer or the like with a built-in thermal head is used. Compared with other recording methods, this thermal recording method is (1) no noise during recording, (2) no need for development and fixing, (3) maintenance-free, (4) machine relatively Due to its low cost, it is widely used in the facsimile field, the output of computers, the field of printers such as calculators, the field of recorders for medical measurement, the field of automatic ticket machines, the field of thermal recording labels, and the like.
近年、感熱記録材料の使用用途が拡大すると共に、より生産性を向上させるため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できる感熱記録材料の開発が強く望まれており、加えて記録画像の保存安定性の向上も望まれている。 In recent years, the use of thermal recording materials has expanded, and the demand for high-speed recording has further increased in order to improve productivity, and the development of thermal recording materials that can sufficiently handle high-speed recording has been strongly desired. Improvement in image storage stability is also desired.
このような要望に対し、特許文献１には顕色性化合物剤として保存安定性に優れた１，３−ジフェニルウレアを単体で用いた感熱記録材料が開示されているが、発色性が未だ不十分であった。 In response to such a demand, Patent Document 1 discloses a heat-sensitive recording material using 1,3-diphenylurea, which is excellent in storage stability as a color developing compound agent, but still has poor color developability. It was enough.
本発明は、前記の発色性の欠点を解決することを目的に、発色性に優れた感熱記録材料を提供することにある。 An object of the present invention is to provide a heat-sensitive recording material excellent in color developability for the purpose of solving the above-mentioned drawbacks of color developability.
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。 The present inventor has completed the present invention as a result of various studies to achieve the above object.
即ち本発明は、
［１］顕色性化合物の１，３−ジフェニルウレアと非フェノール系顕色性化合物を含む事を特徴とする感熱記録材料、
［２］非フェノール系顕色性化合物が、ベンゾトリアゾール誘導体、サッカリン誘導体、スルホンアミド誘導体、マロンアミド誘導体、チオ尿素誘導体、安息香酸誘導体、スルホンアミド誘導体、ウレアウレタン誘導体のいずれかより選ばれる一種であることを特徴とする［１］に記載の感熱記録材料、
［３］非フェノール系顕色性化合物が、スルホンアミド誘導体である事を特徴とする［１］または［２］に記載の感熱記録材料、
に関する。
That is, the present invention
[1] A heat-sensitive recording material comprising a color developing compound 1,3-diphenylurea and a non-phenolic color developing compound,
[2] The non-phenolic color developing compound is a kind selected from any of benzotriazole derivatives, saccharin derivatives, sulfonamide derivatives, malonamide derivatives, thiourea derivatives, benzoic acid derivatives, sulfonamide derivatives, and urea urethane derivatives. The heat-sensitive recording material according to [1], wherein
[3] The heat-sensitive recording material according to [1] or [2], wherein the non-phenolic color developing compound is a sulfonamide derivative,
About.
顕色性化合物の１，３−ジフェニルウレアに非フェノール系顕色性化合物を併用することで、発色性に優れた感熱記録材料を提供することができた。 By using a non-phenolic color developing compound in combination with the color developing compound 1,3-diphenylurea, it was possible to provide a heat-sensitive recording material excellent in color developability.
本発明は、通常無色ないし淡色の発色性化合物と、１，３−ジフェニルウレアと非フェノール系顕色性化合物を含む、また必要に応じてその他の非フェノール系顕色性化合物や増感剤、結合剤、充填剤、保存性向上剤、その他の添加物等を含む感熱記録材料に関する。 The present invention usually comprises a colorless or light-coloring compound, 1,3-diphenylurea and a non-phenolic color developing compound, and if necessary, other non-phenolic color developing compounds and sensitizers, The present invention relates to a heat-sensitive recording material containing a binder, a filler, a storage stability improver, other additives, and the like.
本発明において非フェノール系顕色性化合物とは、分子内にフェノール構造を有しない顕色性化合物のことを意味し、それ自身が公知のものを使用する事ができる。具体例としては、ベンゾトリアゾール誘導体、サッカリン誘導体、スルホンアミド誘導体、マロンアミド誘導体、チオ尿素誘導体、スルホニルウレア誘導体等が挙げられる。 In the present invention, the non-phenolic color developing compound means a color developing compound having no phenol structure in the molecule, and a publicly known one can be used. Specific examples include benzotriazole derivatives, saccharin derivatives, sulfonamide derivatives, malonamide derivatives, thiourea derivatives, sulfonylurea derivatives, and the like.
ベンゾトリアゾール誘導体は、特に限定されるものでは無いが、その具体例としては、ベンゾトリアゾール、５−メチル−１Ｈ−ベンゾトリアゾール、４−メチル−１Ｈ−ベンゾトリアゾール、フェニル−６ベンゾトリアゾール、フェニル−５ベンゾトリアゾール、クロロ−５ベンゾトリアゾール、クロロ−５メチルベンゾトリアゾール、クロロ−５イソプロピル−７メチル−４ベンゾトリアゾール、ブロモ−５ベンゾトリアゾール等が挙げられる。 The benzotriazole derivative is not particularly limited, and specific examples thereof include benzotriazole, 5-methyl-1H-benzotriazole, 4-methyl-1H-benzotriazole, phenyl-6benzotriazole, and phenyl-5. Examples include benzotriazole, chloro-5 benzotriazole, chloro-5 methylbenzotriazole, chloro-5 isopropyl-7 methyl-4 benzotriazole, bromo-5 benzotriazole, and the like.
サッカリン誘導体は、特に限定されるものでは無いが、その具体例としては、サッカリン、１−ブロモサッカリン、１−ニトロサッカリン、１−アミノサッカリン等が挙げられる。 The saccharin derivative is not particularly limited, and specific examples thereof include saccharin, 1-bromosaccharin, 1-nitrosaccharin, 1-aminosaccharin and the like.
スルホンアミド誘導体は、特に限定されるものでは無いが、その具体例としては、メタニルアニリド、Ｎ−フェニル−４−アミノベンゼンスルホンアミド、ネオウリロン、Ｎ−フェニル−３−ニトロベンゼンスルホンアミド、Ｎ−（４−メチル−２−ニトロフェニル）ベンゼンスルホンアミド、Ｎ−（２−メトキシフェニル）−ｐ−ルエンスルホンアミド、Ｎ−（４−トキシフェニル）−ｐ−トルエンスルホンアミド、Ｎ−（２−クロロフェニル）−ｐ−トルエンスルホンアミド、Ｎ−（４−メチルフェニル）−４−メチルベンゼンスルホンアミド、Ｎ−（２−メチルフェニル）−ｐ−トルエンスルホンアミド、Ｎ−フェニルベンゼンスルホンアミド、４−ブロモ−４′−メチルベンゼンスルホンアニリド、Ｎ−（４−ブロモフェニル）ベンゼンスルホンアミド、Ｎ−（３−ニトロフェニル）ベンゼンスルホンアミド、Ｎ−（４−ニトロフェニル）−４−メチルベンゼンスルホンアミド、Ｎ−（４−メチルフェニル）ベンゼンスルホンアミド、Ｎ−フェニル−ｐ−トルエンスルホンアミド、Ｎ−フェニルベンゼンスルホンアミド等が挙げられる。 The sulfonamide derivative is not particularly limited, and specific examples thereof include methanylanilide, N-phenyl-4-aminobenzenesulfonamide, neourilone, N-phenyl-3-nitrobenzenesulfonamide, N- (4- Methyl-2-nitrophenyl) benzenesulfonamide, N- (2-methoxyphenyl) -p-ruenesulfonamide, N- (4-toxylphenyl) -p-toluenesulfonamide, N- (2-chlorophenyl) -p -Toluenesulfonamide, N- (4-methylphenyl) -4-methylbenzenesulfonamide, N- (2-methylphenyl) -p-toluenesulfonamide, N-phenylbenzenesulfonamide, 4-bromo-4'- Methylbenzenesulfonanilide, N- (4-bromophenyl) ben Sulfonamide, N- (3-nitrophenyl) benzenesulfonamide, N- (4-nitrophenyl) -4-methylbenzenesulfonamide, N- (4-methylphenyl) benzenesulfonamide, N-phenyl-p- Toluenesulfonamide, N-phenylbenzenesulfonamide and the like can be mentioned.
マロンアミド誘導体は、特に限定されるものでは無いが、その具体例としては、Ｎ，Ｎ′−ビス（２−ヒドロキシ−５−フェニル）フェニル−マロンアミド、Ｎ，Ｎ′−ジフェニルマロンアミド、Ｎ，Ｎ′−ビス（２，４，６−トリブロモフェニル）マロンアミド、Ｎ，Ｎ′−ビス（２−アミノフェニル）マロンアミド、Ｎ，Ｎ′−ビス（ｍ−トリフルオロメチルフェニル）マロンアミド、Ｎ，Ｎ′−ビス（ｍ−トリフルオロメチルフェニル）α、α−ジクロロマロンアミド、ジエチルマロンジアニリド等が挙げられる。 The malonamide derivative is not particularly limited, and specific examples thereof include N, N′-bis (2-hydroxy-5-phenyl) phenyl-malonamide, N, N′-diphenylmalonamide, N, N '-Bis (2,4,6-tribromophenyl) malonamide, N, N'-bis (2-aminophenyl) malonamide, N, N'-bis (m-trifluoromethylphenyl) malonamide, N, N' -Bis (m-trifluoromethylphenyl) α, α-dichloromalonamide, diethylmalondianilide and the like.
チオ尿素誘導体は、特に限定されるものでは無いが、その具体例としては、１，３−ビス（４−メチルフェニル）チオ尿素、１，３−ビスフェニルチオ尿素、１，３−ビス（４−クロロフェニル）チオ尿素、１，３−ビス（４−メトキシフェニル）チオ尿素、Ｎ，Ｎ′−ビス（３−クロロフェニル）チオ尿素、１，３−ビス（３‐メトキシフェニル）チオ尿素、１，３−ビス（３−メチルフェニル）チオ尿素、１，３−ビス（４−ベンジルフェニル）チオ尿素、１，３−ビス（４‐ブロモフェニル）チオ尿素、１−フェニル−３−ブチルチオ尿素、１−フェニル−３−エチルチオ尿素等が挙げられる。 The thiourea derivative is not particularly limited, and specific examples thereof include 1,3-bis (4-methylphenyl) thiourea, 1,3-bisphenylthiourea, 1,3-bis (4 -Chlorophenyl) thiourea, 1,3-bis (4-methoxyphenyl) thiourea, N, N'-bis (3-chlorophenyl) thiourea, 1,3-bis (3-methoxyphenyl) thiourea, 3-bis (3-methylphenyl) thiourea, 1,3-bis (4-benzylphenyl) thiourea, 1,3-bis (4-bromophenyl) thiourea, 1-phenyl-3-butylthiourea, 1 -Phenyl-3-ethylthiourea and the like.
スルホニルウレア誘導体は、Ｎ−（ｐ−トルエンスルホニル）−Ｎ′−（３−ｎ−ブチルアミノスルホニルフェニル）尿素、Ｎ−（ｐ−トルエンスルホニル）−Ｎ′−（４−トリメチルアセトフェニル）尿素、Ｎ−（ベンゼンスルホニル）−Ｎ′−（３−ｐ−トルエンスルホニルオキシフェニル）尿素、Ｎ−（ｐ−トルエンスルホニル）−Ｎ′−（３−ｐ−トルエンスルホニルフェニル）尿素、Ｎ−（ｐ−トルエンスルホニル）−Ｎ′−（３−フェニルスルホニルオキシフェニル）尿素、トルブタミド、クロロプロパミド等が挙げられる。 The sulfonylurea derivatives include N- (p-toluenesulfonyl) -N ′-(3-n-butylaminosulfonylphenyl) urea, N- (p-toluenesulfonyl) -N ′-(4-trimethylacetophenyl) urea, N -(Benzenesulfonyl) -N '-(3-p-toluenesulfonyloxyphenyl) urea, N- (p-toluenesulfonyl) -N'-(3-p-toluenesulfonylphenyl) urea, N- (p-toluene) Sulfonyl) -N ′-(3-phenylsulfonyloxyphenyl) urea, tolbutamide, chloropropamide and the like.
これらの非フェノール系顕色性化合物の中で、スルホンアミド誘導体、スルホニルウレア誘導体が好ましく、スルホンアミド誘導体が特に好ましい。 Among these non-phenolic color developing compounds, sulfonamide derivatives and sulfonylurea derivatives are preferable, and sulfonamide derivatives are particularly preferable.
本発明における感熱記録材料を形成するにあたり、感熱記録材料中に含まれる、１，３−ジフェニルウレアと非フェノール系顕色性化合物の合計量は通常１〜５０重量％、好ましくは５〜３０重量％、増感剤は１〜８０重量％、結合剤は通常１〜９０重量％、保存性向上剤は通常０〜３０重量％、充填剤は通常０〜８０重量％、その他の滑剤、界面活性剤、消泡剤、紫外線吸収剤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％は感熱記録層中に占める各成分の重量比）。更に好ましい態様としては、上記のような組成のうちで１，３‐ジフェニルウレアと非フェノール系顕色性化合物との重量比は９：１〜１：９が好ましく、２：８〜６：４が特に好ましい。また、本発明の感熱記録材料においては、前記成分以外のそれ自身が公知の顕色性化合物、増感剤又はその他の添加物を併用しても構わない。 In forming the heat-sensitive recording material in the present invention, the total amount of 1,3-diphenylurea and non-phenolic color developing compound contained in the heat-sensitive recording material is usually 1 to 50% by weight, preferably 5 to 30% by weight. %, Sensitizer 1-80 wt%, Binder usually 1-90 wt%, Preservative improver usually 0-30 wt%, Filler usually 0-80 wt%, Other lubricants, surfactant The agent, the antifoaming agent, and the ultraviolet absorber are each used in an arbitrary ratio, for example, usually 0 to 30% by weight, respectively. In a more preferred embodiment, the weight ratio of 1,3-diphenylurea to non-phenolic color developing compound is preferably 9: 1 to 1: 9 in the above composition, and 2: 8 to 6: 4. Is particularly preferred. In the heat-sensitive recording material of the present invention, a known color developing compound, sensitizer or other additive may be used in combination other than the above components.
本発明に用いられる発色性化合物は、一般に感圧記録紙や感熱記録紙に用いられるものであればよく、特に制限されない。用いられ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が挙げられ、フルオラン系化合物が好ましい。 The color-forming compound used in the present invention is not particularly limited as long as it is generally used for pressure-sensitive recording paper and heat-sensitive recording paper. Examples of the chromogenic compound used include fluoran compounds, triarylmethane compounds, spiro compounds, diphenylmethane compounds, thiazine compounds, lactam compounds, and fluorene compounds, with fluorane compounds being preferred.
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−ジエチルアミノ−７−（ｏ−フルオロアニリノ）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、３−ジブチルアミノ−６−メチル−７−アニリノフルオランが好ましい。 Specific examples of the fluorane compound include 3-diethylamino-6-methyl-7-anilinofluorane, 3-dibutylamino-6-methyl-7-anilinofluorane, 3- (N-methyl-N- Cyclohexylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-isopentylamino) -6-methyl-7-anilinofluorane, 3- (N-ethyl-N-isobutyl) Amino) -6-methyl-7-anilinofluorane, 3- [N-ethyl-N- (3-ethoxypropyl) amino] -6-methyl-7-anilinofluorane, 3- (N-ethyl- N-hexylamino) -6-methyl-7-anilinofluorane, 3-dipentylamino-6-methyl-7-anilinofluorane, 3- (N-methyl-N-propylamino) -6-me Ru-7-anilinofluorane, 3- (N-ethyl-N-tetrahydrofurylamino) -6-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7- (p-chloroanilino) fluorane 3-diethylamino-6-methyl-7- (p-fluoroanilino) fluorane, 3- [N-ethyl-N- (p-tolyl) amino] -6-methyl-7-anilinofluorane, 3- Diethylamino-6-methyl-7- (p-toluidino) fluorane, 3-diethylamino-7- (o-chloroanilino) fluorane, 3-dibutylamino-7- (o-chloroanilino) fluorane, 3-diethylamino-7- (o -Fluoroanilino) fluorane, 3-dibutylamino-7- (o-fluoroanilino) fluorane, 3-diethylamino-7- 3,4-dichloroanilino) fluorane, 3-pyrrolidino-6-methyl-7-anilinofluorane, 3-diethylamino-6-chloro-7-ethoxyethylaminofluorane, 3-diethylamino-6-chloro-7 -Anilinofluorane, 3-diethylamino-7-chlorofluorane, 3-diethylamino-7-methylfluorane, 3-diethylamino-7-octylfluorane, 3- [N-ethyl-N- (p-tolyl) Amino] -6-methyl-7-phenethylfluorane and the like, and 3-dibutylamino-6-methyl-7-anilinofluorane is preferred.
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。 Specific examples of triarylmethane compounds include, for example, 3,3-bis (p-dimethylaminophenyl) -6-dimethylaminophthalide (also known as crystal violet lactone or CVL), 3,3-bis (p-dimethyl). Aminophenyl) phthalide, 3- (p-dimethylaminophenyl) -3- (1,2-dimethylaminoindol-3-yl) phthalide, 3- (p-dimethylaminophenyl) -3- (2-methylindole- 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, 3,3-bis 9-ethylcarbazol-3-yl) -5-dimethylaminophthalide, 3,3- (2-phenylindol-3-yl) -5-dimethylaminophthalide, 3-p-dimethylaminophenyl-3- ( 1-methylpyrrol-2-yl) -6-dimethylaminophthalide and the like.
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；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；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；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；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。 Specific examples of the spiro compound include, for example, 3-methylspirodinaphthopyran, 3-ethylspirodinaphthopyran, 3,3′-dichlorospirodinaphthopyran, 3-benzylspirodinaphthopyran, 3-propylspirobenzo. Pyran, 3-methylnaphtho- (3-methoxybenzo) spiropyran, 1,3,3-trimethyl-6-nitro-8′-methoxyspiro (indoline-2,2′-benzopyran), etc .; specific examples of diphenylmethane compounds Are, for example, N-halophenyl-leucooramine, 4,4-bis-dimethylaminophenylbenzhydrylbenzyl ether, N-2,4,5-trichlorophenylleucooramine, and the like. Specific examples of thiazine compounds include For example, benzoylleucomethylene blue, p-nitrobenzoylleucome Specific examples of lactam compounds include, for example, rhodamine B anilinolactam, rhodamine Bp-chloroanilinolactam, etc .; specific examples of fluorene compounds include, for example, 3,6-bis (dimethylamino) fluorene Spiro (9,3 ′)-6′-dimethylaminophthalide, 3,6-bis (dimethylamino) fluorene spiro (9,3 ′)-6′-pyrrolidinophthalide, 3-dimethylamino-6-diethylamino Fluorene spiro (9,3 ′)-6′-pyrrolidinophthalide and the like. These color forming compounds are used alone or in combination.
本発明において併用可能な顕色性化合物としては、特に制限されないが、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、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、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、２，２’−ビス（２，５−ジブロム−４−ヒドロキシフェニル）プロパン、４，４’−イソプロピリデンビス（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、４−ヒドロキシ−４’−メト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、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’−エトキシジフェニルスルホン、４−ヒドロキシ−４’−ブト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、２，４−ジヒドロキシ−２’−メトキシベンズアニリド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。 The color developing compound that can be used in combination in the present invention is not particularly limited, and may be any compound that is generally used for pressure-sensitive recording paper and heat-sensitive recording paper. For example, α-naphthol, β-naphthol, p-octylphenol. 4-tert-octylphenol, pt-butylphenol, p-phenylphenol, 1,1-bis (p-hydroxyphenyl) propane, 2,2-bis (p-hydroxyphenyl) propane (also known as bisphenol A or BPA) ), 2,2-bis (p-hydroxyphenyl) butane, 1,1-bis (p-hydroxyphenyl) cyclohexane, 4,4′-thiobisphenol, 4,4′-cyclo-hexylidene diphenol, 2, 2'-bis (2,5-dibromo-4-hydroxyphenyl) propane, 4,4'-isopropylidene Bis (2-t-butylphenol), 2,2′-methylenebis (4-chlorophenol), 4,4′-dihydroxydiphenylsulfone, 4-hydroxy-4′-methoxydiphenylsulfone, 2,4′-dihydroxydiphenylsulfone 4-hydroxy-4′-isopropoxydiphenylsulfone, 4-hydroxy-4′-ethoxydiphenylsulfone, 4-hydroxy-4′-butoxydiphenylsulfone, 4-hydroxy-4′-benzyloxydiphenylsulfone, bis (4 Phenolic compounds such as -hydroxyphenyl) methyl acetate, bis (4-hydroxyphenyl) butyl acetate, bis (4-hydroxyphenyl) acetate benzyl, 2,4-dihydroxy-2'-methoxybenzanilide, p-hydroxybenzoic acid Benzyl, p- Such as ethyl droxybenzoate, dibenzyl 4-hydroxyphthalate, dimethyl 4-hydroxyphthalate, ethyl 5-hydroxyisophthalate, 3,5-di-t-butylsalicylic acid, 3,5-di-α-methylbenzylsalicylic acid, etc. An aromatic carboxylic acid derivative, an aromatic carboxylic acid or a polyvalent metal salt thereof can be used.
本発明に用いられる増感剤（熱可融性化合物）の具体例としては、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、スルホン誘導体等が挙げられ、中でも常温では固体で、融点が６０℃以上のものが好ましく使用される。 Specific examples of the sensitizer (thermofusible compound) 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, and aromatic ethers. , Aromatic carboxylic acid derivatives, aromatic sulfonic acid ester derivatives, carbonic acid or oxalic acid diester derivatives, biphenyl derivatives, terphenyl derivatives, sulfone derivatives, etc. Among them, those which are solid at room temperature and have a melting point of 60 ° C. or higher are preferable. used.
ワックス類の具体例としては、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；高級脂肪酸としては、例えばステアリン酸、ベヘン酸等；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；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；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；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；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；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；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；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−アリルオキシビフェニル等；ターフェニル誘導体としては、例えばｍ−ターフェニル等；スルホン誘導体としては、例えばジフェニルスルホン等、が挙げられる。 Specific examples of waxes include, for example, wood wax, carnauba wax, shellac, paraffin, montan wax, oxidized paraffin, polyethylene wax, polyethylene oxide, etc .; higher fatty acids such as stearic acid, behenic acid, etc .; higher fatty acid amides For example, stearic acid amide, oleic acid amide, N-methyl stearic acid amide, erucic acid amide, methylol behenic acid amide, methylene bis stearic acid amide, ethylene bis stearic acid amide, etc .; Linoleic acid anilide, etc .; As naphthalene derivatives, for example, 1-benzyloxynaphthalene, 2-benzyloxynaphthalene, 1-hydroxynaphthoic acid phenyl ester, etc .; As aromatic ethers, for example, 1,2- Phenoxyethane, 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 .; examples of aromatic carboxylic acid derivatives include p -Hydroxybenzoic acid benzyl ester, p-benzyloxybenzoic acid benzyl ester, terephthalic acid dibenzyl ester, etc .; examples of aromatic sulfonic acid ester derivatives include p-toluenesulfonic acid phenyl ester, phenylmesitylene sulfonate, 4-methylphenyl Mesitylene sulfonate, etc .; carbonic acid or dioxalic acid Examples of the steal derivatives include diphenyl carbonate, oxalic acid dibenzyl ester, oxalic acid di (4-chlorobenzyl) ester, and oxalic acid di (4-methylbenzyl) ester; examples of the biphenyl derivative include p-benzyl biphenyl, p -Allyloxybiphenyl and the like; Examples of the terphenyl derivative include m-terphenyl and the like; Examples of the sulfone derivative include diphenylsulfone and the like.
本発明に用いられ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、シリル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（メタ）アクリル酸エステル共重合体、スチレン／（メタ）アクリル酸エステル共重合体、ポリウレタン、ポリエステル系ポリウレタン、ポリエーテル系ポリウレタン、ポリ酢酸ビニル、エチレン／酢酸ビニル共重合体、ポリ塩化ビニル、塩化ビニル／酢酸ビニル共重合体、ポリ塩化ビニリデン、ポリスチレン、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、アクリロニトリル／ブタジエン（ＮＢ）共重合体、カルボキシル化アクリロニトリル／ブタジエン（ＮＢ）共重合体、コロイダルシリカと（メタ）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挙げられる。 Specific examples of the binder used in the present invention 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, Silyl 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, iso (or diiso) butylene / anhydrous Water-soluble maleic acid copolymer such as alkali salt, (meth) acrylic acid ester copolymer, styrene / (meth) acrylic acid ester copolymer , Polyurethane, polyester polyurethane, polyether polyurethane, polyvinyl acetate, ethylene / vinyl acetate copolymer, polyvinyl chloride, vinyl chloride / vinyl acetate copolymer, polyvinylidene chloride, polystyrene, styrene / butadiene (SB) Polymer, carboxylated styrene / butadiene (SB) copolymer, styrene / butadiene / acrylic acid copolymer, acrylonitrile / butadiene (NB) copolymer, carboxylated acrylonitrile / butadiene (NB) copolymer, colloidal silica And hydrophobic polymer emulsions such as composite particles of (meth) acrylic resin.
本発明に用いられ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挙げられる。 Specific examples of the filler used in the present invention 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. And urea-formalin resin.
本発明に用いられる保存性向上剤の具体例としては、例えば２，２’−メチレンビス（４−メチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−メチレンビス（４−エチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−エチリデンビス（４，６−ジ−ｔｅｒｔ−ブチルフェノール）、４，４’−チオビス（２−メチル−６−ｔｅｒｔ−ブチルフェノール）、４，４’−ブチリデンビス（６−ｔｅｒｔ−ブチル−ｍ−クレゾール）、１−〔α−メチル−α−（４’−ヒドロキシフェニル）エチル〕−４−〔α’，α’−ビス（４’−ヒドロキシフェニル）エチル〕ベンゼン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−シクロヘキシルフェニル）ブタン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−ｔｅｒｔ−ブチルフェニル）ブタン、トリス（２，６−ジメチル−４−ターシャリーブチル−３−ヒドロキシベンジル）イソシアヌレート、４，４’−チオビス（３−メチルフェノール）、４，４’−ジヒドロキシ−３，３’，５，５’−テトラブロモジフェニルスルホン、４，４’−ジヒドロキシ−３，３’，５，５’−テトラメチルジフェニルスルホン、２，２−ビス（４−ヒドロキシ−３，５−ジブロモフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジクロロフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジメチルフェニル）プロパン等のヒンダードフェノール化合物、１，４−ジグリシジルオキシベンゼン、４，４’−ジグリシジルオキシジフェニルスルホン、４−ベンジルオキシ−４’−（２−メチルグリシジルオキシ）ジフェニルスルホン、テレフタル酸ジグリシジル、クレゾールノボラック型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、ビスフェノールＡ型エポキシ樹脂等のエポキシ化合物、Ｎ，Ｎ’−ジ−２−ナフチル−ｐ−フェニレンジアミン、２，２’−メチレンビス（４，６−ジ−ｔｅｒｔ−ブチルフェニル）ホスフェイトのナトリウムまたは多価金属塩、ビス（４−エチレンイミノカルボニルアミノフェニル）メタン等が挙げられる。例えば２，２’−メチレンビス（４−メチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−メチレンビス（４−エチル−６−ｔｅｒｔ−ブチルフェノール）、２，２’−エチリデンビス（４，６−ジ−ｔｅｒｔ−ブチルフェノール）、４，４’−チオビス（２−メチル−６−ｔｅｒｔ−ブチルフェノール）、４，４’−ブチリデンビス（６−ｔｅｒｔ−ブチル−ｍ−クレゾール）、１−〔α−メチル−α−（４’−ヒドロキシフェニル）エチル〕−４−〔α’，α’−ビス（４’−ヒドロキシフェニル）エチル〕ベンゼン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−シクロヘキシルフェニル）ブタン、１，１，３−トリス（２−メチル−４−ヒドロキシ−５−ｔｅｒｔ−ブチルフェニル）ブタン、トリス（２，６−ジメチル−４−ターシャリーブチル−３−ヒドロキシベンジル）イソシアヌレート、４，４’−チオビス（３−メチルフェノール）、４，４’−ジヒドロキシ−３，３’，５，５’−テトラブロモジフェニルスルホン、４，４’−ジヒドロキシ−３，３’，５，５’−テトラメチルジフェニルスルホン、２，２−ビス（４−ヒドロキシ−３，５−ジブロモフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジクロロフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジメチルフェニル）プロパン等のヒンダードフェノール化合物、１，４−ジグリシジルオキシベンゼン、４，４’−ジグリシジルオキシジフェニルスルホン、４−ベンジルオキシ−４’−（２−メチルグリシジルオキシ）ジフェニルスルホン、テレフタル酸ジグリシジル、クレゾールノボラック型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、ビスフェノールＡ型エポキシ樹脂等のエポキシ化合物、Ｎ，Ｎ’−ジ−２−ナフチル−ｐ−フェニレンジアミン、２，２’−メチレンビス（４，６−ジ−ｔｅｒｔ−ブチルフェニル）ホスフェイトのナトリウムまたは多価金属塩、ビス（４−エチレンイミノカルボニルアミノフェニル）メタン等が挙げられる。 Specific examples of the storage stability improver used in the present invention include, for example, 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6-tert-butylphenol). ), 2,2′-ethylidenebis (4,6-di-tert-butylphenol), 4,4′-thiobis (2-methyl-6-tert-butylphenol), 4,4′-butylidenebis (6-tert- Butyl-m-cresol), 1- [α-methyl-α- (4′-hydroxyphenyl) ethyl] -4- [α ′, α′-bis (4′-hydroxyphenyl) ethyl] benzene, 1,1 , 3-Tris (2-methyl-4-hydroxy-5-cyclohexylphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-tert- Tilphenyl) butane, tris (2,6-dimethyl-4-tertiarybutyl-3-hydroxybenzyl) isocyanurate, 4,4′-thiobis (3-methylphenol), 4,4′-dihydroxy-3,3 ′ , 5,5′-tetrabromodiphenylsulfone, 4,4′-dihydroxy-3,3 ′, 5,5′-tetramethyldiphenylsulfone, 2,2-bis (4-hydroxy-3,5-dibromophenyl) Hindered phenol compounds such as propane, 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane, 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 1,4-di Glycidyloxybenzene, 4,4′-diglycidyloxydiphenylsulfone, 4-benzyloxy-4 ′-(2-methylglyci (Zyloxy) diphenylsulfone, diglycidyl terephthalate, cresol novolac type epoxy resin, phenol novolac type epoxy resin, bisphenol A type epoxy resin, N, N′-di-2-naphthyl-p-phenylenediamine, 2,2 Examples include sodium or polyvalent metal salts of '-methylenebis (4,6-di-tert-butylphenyl) phosphate, bis (4-ethyleneiminocarbonylaminophenyl) methane, and the like. For example, 2,2'-methylenebis (4-methyl-6-tert-butylphenol), 2,2'-methylenebis (4-ethyl-6-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-) -Tert-butylphenol), 4,4'-thiobis (2-methyl-6-tert-butylphenol), 4,4'-butylidenebis (6-tert-butyl-m-cresol), 1- [α-methyl-α -(4'-hydroxyphenyl) ethyl] -4- [α ', α'-bis (4'-hydroxyphenyl) ethyl] benzene, 1,1,3-tris (2-methyl-4-hydroxy-5- Cyclohexylphenyl) butane, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, tris (2,6-dimethyl) 4-tertiarybutyl-3-hydroxybenzyl) isocyanurate, 4,4′-thiobis (3-methylphenol), 4,4′-dihydroxy-3,3 ′, 5,5′-tetrabromodiphenylsulfone, 4 , 4′-dihydroxy-3,3 ′, 5,5′-tetramethyldiphenylsulfone, 2,2-bis (4-hydroxy-3,5-dibromophenyl) propane, 2,2-bis (4-hydroxy-) Hindered phenol compounds such as 3,5-dichlorophenyl) propane and 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 1,4-diglycidyloxybenzene, 4,4′-diglycidyloxy Diphenyl sulfone, 4-benzyloxy-4 ′-(2-methylglycidyloxy) diphenyl sulfone, terephthalic acid digg Epoxy compounds such as lysidyl, cresol novolac type epoxy resin, phenol novolac type epoxy resin, bisphenol A type epoxy resin, N, N′-di-2-naphthyl-p-phenylenediamine, 2,2′-methylenebis (4,6 -Di-tert-butylphenyl) phosphate sodium or polyvalent metal salt, bis (4-ethyleneiminocarbonylaminophenyl) methane and the like.
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、例えばサーマルヘッド磨耗防止、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、酸化防止あるい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、等が挙げられる。 Furthermore, various additives other than those described above can be used in the present invention. For example, higher fatty acid metal salts such as zinc stearate and calcium stearate for the purpose of preventing thermal head wear and sticking, and preventing oxidation or aging. Examples thereof include ultraviolet absorbers such as phenol derivatives, benzophenone compounds, and benzotriazole compounds for imparting effects, various surfactants, and antifoaming agents.
次に、本発明の感熱記録材料の調製方法を説明する。本発明に用いられる、発色性化合物、顕色性化合物の１，３−ジフェニルウレアと非フェノール系顕色性化合物の混合物を、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、サンドミル等の分散機にて粉砕、分散化し分散液とした後（通常、粉砕や分散を湿式で行うときは水を媒体として用いる）、分散液を混合して感熱記録材料の塗布液を調製し、紙（普通紙、上質紙、コート紙等が使用出来る）、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からなる感熱記録層を有する試料を作製する。 Next, a method for preparing the heat-sensitive recording material of the present invention will be described. A ball mill comprising a mixture of a chromogenic compound, a color developing compound 1,3-diphenylurea and a non-phenolic color developing compound, respectively, together with a binder or other additives as required After pulverizing and dispersing with a disperser such as an attritor or sand mill to obtain a dispersion (usually, water is used as a medium when pulverization or dispersion is carried out in a wet manner), and then the dispersion is mixed to apply a heat-sensitive recording material. Prepare a liquid and use a bar coater or blade so that the dry weight is usually 1 to 20 g / m 2 on a support such as paper (plain paper, fine paper, coated paper, etc.), plastic sheet, synthetic paper, etc. A sample having a heat-sensitive recording layer made of the heat-sensitive recording material of the present invention is prepared by coating and drying with a coater or the like.
また、必要に応じて感熱記録層と支持体の間に中間層を設けたり、感熱記録層上にオーバーコート層（保護層）を設けても良い。中間層、オーバーコート層（保護層）は、例えば前記の結合剤あるいは必要に応じてその他の添加物と共に、前記の感熱記録材料の塗布液の調製方法と同様に必要に応じて粉砕、分散して中間層用塗布液又はオーバーコート層（保護層）用塗布液とした後、乾燥時の重量で通常０．１〜１０ｇ／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。 If necessary, an intermediate layer may be provided between the heat-sensitive recording layer and the support, or an overcoat layer (protective layer) may be provided on the heat-sensitive recording layer. For example, the intermediate layer and the overcoat layer (protective layer) are pulverized and dispersed as necessary together with the above-mentioned binder or other additives as necessary, in the same manner as the method for preparing the coating solution for the above-mentioned thermal recording material. The coating solution for the intermediate layer or the coating solution for the overcoat layer (protective layer) is applied by drying so that the weight is usually about 0.1 to 10 g / m 2 and dried.
本発明を実施例により更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、溶液の説明における「％」は重量％である。 The present invention will be described more specifically with reference to examples, but the present invention is not limited thereto. In the examples, “parts” are parts by weight, and “%” in the description of the solution is% by weight.
［実施例１］（感熱記録材料の作製）
特許文献１に開示の１、３−ジフェニル尿素を下記組成で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［Ａ］液を調製した。
[Example 1] (Preparation of thermosensitive recording material)
The [A] liquid was prepared by pulverizing and dispersing 1,3-diphenylurea disclosed in Patent Document 1 using a sand grinder with the following composition so that the average particle size was 1 μm or less.
［Ａ］液：１、３−ジフェニル尿素（東京化成工業社製） ２５部
２５％ＰＶＡ水溶液 ２０部
水 ５５部
[A] Liquid: 25 parts of 1,3-diphenylurea (manufactured by Tokyo Chemical Industry Co., Ltd.)
20 parts of 25% PVA aqueous solution
55 parts of water
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、分散化して発色性化合物の［Ｂ］液を調製した。
［Ｂ］液：３−ジブチルアミノ−６−メチル−７−アニリノフルオラン ３５部
１５％ＰＶＡ水溶液 ４０部
水 ２５部
A mixture of the following composition was pulverized and dispersed using a sand grinder so that the average particle size was 1 μm or less to prepare a [B] solution of a color forming compound.
[B] Liquid: 35 parts of 3-dibutylamino-6-methyl-7-anilinofluorane
40 parts of 15% PVA aqueous solution
25 parts of water
本発明において併用するＮ−フェニルベンゼンスルホンアミドを下記組成で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、分散化してスルホンアミド誘導体の［Ｃ］液を調製した。
［Ｃ］液：Ｎ−フェニルベンゼンスルホンアミド（東京化成工業社製） ２５部
２５％ＰＶＡ水溶液 ２０部
水 ５５部
N-phenylbenzenesulfonamide used in the present invention was pulverized and dispersed using a sand grinder with the following composition so as to have an average particle size of 1 μm or less to prepare a [C] solution of a sulfonamide derivative.
[C] Liquid: 25 parts of N-phenylbenzenesulfonamide (Tokyo Chemical Industry Co., Ltd.)
20 parts of 25% PVA aqueous solution
55 parts of water
次いで、上記で得た各分散液を下記の組成で混合して感熱記録材料塗布液を調製し、坪量５０ｇ／ｍ２の上質紙上に乾燥時の重量が５ｇ／ｍ２となるように塗布、乾燥して本発明の感熱記録材料を有する試料を得た。
［Ａ］液 １９．２部
［Ｂ］液 ８．６部
［Ｃ］液 ４．８部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
Then, applying to the heat-sensitive recording material coating solution is prepared by mixing the dispersion obtained above in the following composition, by weight of the dry to the fine paper having a basis weight of 50 g / m 2 is 5 g / m 2 And dried to obtain a sample having the heat-sensitive recording material of the present invention.
[A] Liquid 19.2 parts [B] Liquid 8.6 parts [C] Liquid 4.8 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% Modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
（保護層の形成）
次に下記割合からなる保護層塗布液を前記の感熱記録層上に乾燥時の重量が２ｇ／ｍ２となるように塗布、乾燥して保護層付きの感熱記録層を得た。
４０％スチレン／アクリル酸エステル共重合体エマルジョン １１５部
５％ベントナイト水分散液 １７部
４５％スチレン・アクリル共重合体水性エマルジョン ４４部
３９％ステアリン酸亜鉛水分散液 １０３部
６７％炭酸カルシウム水分散液 １５部
(Formation of protective layer)
Next, a protective layer coating solution having the following ratio was applied on the heat-sensitive recording layer so that the weight upon drying was 2 g / m 2 and dried to obtain a heat-sensitive recording layer with a protective layer.
40% styrene / acrylic ester copolymer emulsion 115 parts 5% bentonite aqueous dispersion 17 parts 45% styrene / acrylic copolymer aqueous emulsion 44 parts 39% zinc stearate aqueous dispersion 103 parts 67% calcium carbonate aqueous dispersion 15 copies
［実施例２］
上記の［Ａ］液、［Ｂ］液、［Ｃ］液を、下記の組成比で混合した以外は実施例１と同様に塗布、乾燥して本発明の感熱記録材料を有する試料を得た。
［Ａ］液 １４．４部
［Ｂ］液 ８．６部
［Ｃ］液 ９．６部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
[Example 2]
A sample having the heat-sensitive recording material of the present invention was obtained by applying and drying the above [A] solution, [B] solution, and [C] solution in the same manner as in Example 1 except that they were mixed in the following composition ratio. .
[A] Liquid 14.4 parts [B] Liquid 8.6 parts [C] Liquid 9.6 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% Modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
［実施例３］
上記の［Ａ］、［Ｂ］、［Ｃ］液を、下記の組成比で混合した以外は実施例１と同様に塗布、乾燥して本発明の感熱記録材料を有する試料を得た。
［Ａ］液 １２．０部
［Ｂ］液 ８．６部
［Ｃ］液 １２．０部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
[Example 3]
A sample having the heat-sensitive recording material of the present invention was obtained by applying and drying the above [A], [B], and [C] liquids in the same manner as in Example 1 except that they were mixed at the following composition ratios.
[A] Liquid 12.0 parts [B] Liquid 8.6 parts [C] Liquid 12.0 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
［実施例４］
上記の［Ａ］、［Ｂ］、［Ｃ］液を、下記の組成比で混合した以外は実施例１と同様に塗布、乾燥して本発明の感熱記録材料を有する試料を得た。
［Ａ］液 ９．６部
［Ｂ］液 ８．６部
［Ｃ］液 １４．４部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
[Example 4]
A sample having the heat-sensitive recording material of the present invention was obtained by applying and drying the above [A], [B], and [C] liquids in the same manner as in Example 1 except that they were mixed at the following composition ratios.
[A] Liquid 9.6 parts [B] Liquid 8.6 parts [C] Liquid 14.4 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% Modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
［実施例５］
上記の［Ａ］、［Ｂ］、［Ｃ］液を、下記の組成比で混合した以外は実施例１と同様に塗布、乾燥して本発明の感熱記録材料を有する試料を得た。
［Ａ］液 ４．８部
［Ｂ］液 ８．６部
［Ｃ］液 １９．２部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
[Example 5]
A sample having the heat-sensitive recording material of the present invention was obtained by applying and drying the above [A], [B], and [C] liquids in the same manner as in Example 1 except that they were mixed at the following composition ratios.
[A] Liquid 4.8 parts [B] Liquid 8.6 parts [C] Liquid 19.2 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% Modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
［実施例６］
上記の［Ａ］、［Ｂ］、［Ｃ］液を、下記の組成比で混合した以外は実施例１と同様に塗布、乾燥して本発明の感熱記録材料を有する試料を得た。
［Ａ］液 ２．４部
［Ｂ］液 ８．６部
［Ｃ］液 ２１．６部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
[Example 6]
A sample having the heat-sensitive recording material of the present invention was obtained by applying and drying the above [A], [B], and [C] liquids in the same manner as in Example 1 except that they were mixed at the following composition ratios.
[A] Liquid 2.4 parts [B] Liquid 8.6 parts [C] Liquid 21.6 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% modified styrene / butadiene copolymer latex 6.3 parts Water 44.1 parts
［比較例１］
上記の［Ａ］及び［Ｂ］液を、下記の組成比で混合した以外は実施例１と同様に塗布、乾燥して比較用の感熱記録材料を有する試料を得た。
［Ａ］液 ２４．０部
［Ｂ］液 ８．６部
６７％炭酸カルシウム水分散液 ９．０部
４８％変性スチレン・ブタジエン共重合体ラテックス ６．３部
水 ４４．１部
[Comparative Example 1]
A sample having a comparative heat-sensitive recording material was obtained by applying and drying the above [A] and [B] liquids in the same manner as in Example 1 except that they were mixed in the following composition ratio.
[A] Liquid 24.0 parts [B] Liquid 8.6 parts 67% calcium carbonate aqueous dispersion 9.0 parts 48% modified styrene-butadiene copolymer latex 6.3 parts Water 44.1 parts
［発色性試験（動発色感度）］
上記の実施例１〜６及び比較例１で得られた感熱記録材料を有する試料を、それぞれオオクラエンジニアリング株式会社製のサーマルプリンター（ＴＨ−Ｍ２／ＰＰ）を用いてパルス幅１．１ｍｓｅｃで印字し、印字部分のマクベス反射濃度をＧＲＥＴＡＧ−ＭＡＣＢＥＴＨ社製の測色機、商品名 ＳｐｅｃｔｒｏＥｙｅ を用いて測定した。測色する際は、いずれも光源にイルミナントＣ、濃度基準にＡＮＳＩ Ａ、視野角２度の条件で行った。結果を表１に示す。なお、マクベス反射濃度が高い程、発色性に優れていることがわかる。
[Color development test (dynamic color development sensitivity)]
Samples having the heat-sensitive recording materials obtained in Examples 1 to 6 and Comparative Example 1 were printed with a pulse width of 1.1 msec using a thermal printer (TH-M2 / PP) manufactured by Okura Engineering Co., Ltd. The Macbeth reflection density of the printed portion was measured using a colorimeter manufactured by GRETAG-MACBETH, trade name: SpectroEye. When measuring colors, all were performed under the conditions of Illuminant C as the light source, ANSI A as the density standard, and a viewing angle of 2 degrees. The results are shown in Table 1. It can be seen that the higher the Macbeth reflection density, the better the color developability.
表１中の比率は、１、３−ジフェニル尿素とＮ‐フェニルベンゼンスルホンアミドの重量比を示す。
表１より明らかなように、１，３−ジフェニル尿素と非フェノール系顕色性化合物を併用した本発明の感熱記録材料は、顕色性化合物を単体で使用した比較例１に比べて高い発色濃度（マクベス反射濃度）を示した。
As is clear from Table 1, the heat-sensitive recording material of the present invention using 1,3-diphenylurea and a non-phenolic color developing compound in combination has a higher color development than Comparative Example 1 using the color developing compound alone. The density (Macbeth reflection density) was shown.
Claims (3)
The heat-sensitive recording material according to claim 1 or 2, wherein the non-phenolic color developing compound is a sulfonamide derivative.
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| JP2014200699A JP2016068418A (en) | 2014-09-30 | 2014-09-30 | Heat-sensitive recording material |
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| JP2014200699A JP2016068418A (en) | 2014-09-30 | 2014-09-30 | Heat-sensitive recording material |
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| JP2019130879A (en) * | 2018-02-01 | 2019-08-08 | 日本化薬株式会社 | Heat-sensitive recording material |
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| JP2019084758A (en) * | 2017-11-07 | 2019-06-06 | 日本化薬株式会社 | Thermal recording material |
| JP2019130879A (en) * | 2018-02-01 | 2019-08-08 | 日本化薬株式会社 | Heat-sensitive recording material |
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