JP7387197B2 - ウレイレン-ジ(ヒドロキシ安息香酸エステル)誘導体、及びそれを用いた感熱記録材料 - Google Patents
ウレイレン-ジ(ヒドロキシ安息香酸エステル)誘導体、及びそれを用いた感熱記録材料 Download PDFInfo
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- JP7387197B2 JP7387197B2 JP2022102475A JP2022102475A JP7387197B2 JP 7387197 B2 JP7387197 B2 JP 7387197B2 JP 2022102475 A JP2022102475 A JP 2022102475A JP 2022102475 A JP2022102475 A JP 2022102475A JP 7387197 B2 JP7387197 B2 JP 7387197B2
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- BEZQTEBPMMEPNB-UHFFFAOYSA-N ethyl 4-amino-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1O BEZQTEBPMMEPNB-UHFFFAOYSA-N 0.000 description 1
- SVLMEEHRAATUJY-UHFFFAOYSA-N ethyl 4-amino-3-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(N)C(O)=C1 SVLMEEHRAATUJY-UHFFFAOYSA-N 0.000 description 1
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 1
- FYCPYYOESKUODV-UHFFFAOYSA-N ethyl 5-amino-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC(N)=CC=C1O FYCPYYOESKUODV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GDIJXOCHGFQHCT-UHFFFAOYSA-N methyl 2-amino-3-hydroxybenzoate Chemical compound COC(=O)C1=CC=CC(O)=C1N GDIJXOCHGFQHCT-UHFFFAOYSA-N 0.000 description 1
- DWBKSTKVIIRFHL-UHFFFAOYSA-N methyl 2-amino-5-hydroxybenzoate Chemical compound COC(=O)C1=CC(O)=CC=C1N DWBKSTKVIIRFHL-UHFFFAOYSA-N 0.000 description 1
- DMNGQQIFOZYIRA-UHFFFAOYSA-N methyl 3-amino-5-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC(O)=C1 DMNGQQIFOZYIRA-UHFFFAOYSA-N 0.000 description 1
- OCZXDVNSNDITBS-UHFFFAOYSA-N methyl 4-amino-3-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(N)C(O)=C1 OCZXDVNSNDITBS-UHFFFAOYSA-N 0.000 description 1
- MXUHMQZOATZRIK-UHFFFAOYSA-N methyl 5-amino-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1O MXUHMQZOATZRIK-UHFFFAOYSA-N 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 229920001778 nylon Polymers 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
- 239000012044 organic layer Substances 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 229950006098 orthocaine Drugs 0.000 description 1
- 239000004209 oxidized polyethylene wax Substances 0.000 description 1
- 235000013873 oxidized polyethylene wax Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 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
- 239000011087 paperboard Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- IJSCTKBCAWDOKS-UHFFFAOYSA-N phenyl 5-amino-2-hydroxybenzoate Chemical compound NC1=CC=C(O)C(C(=O)OC=2C=CC=CC=2)=C1 IJSCTKBCAWDOKS-UHFFFAOYSA-N 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- YBUHABZMSNVUKQ-UHFFFAOYSA-N propan-2-yl 4-amino-2-hydroxybenzoate Chemical compound CC(C)OC(=O)C1=CC=C(N)C=C1O YBUHABZMSNVUKQ-UHFFFAOYSA-N 0.000 description 1
- QQSWKDRPBHPAAL-UHFFFAOYSA-N propan-2-yl 5-amino-2-hydroxybenzoate Chemical compound CC(C)OC(=O)C1=CC(N)=CC=C1O QQSWKDRPBHPAAL-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- AXVUUIKLTMGZMH-UHFFFAOYSA-N propyl 2-amino-3-hydroxybenzoate Chemical compound CCCOC(=O)C1=C(N)C(O)=CC=C1 AXVUUIKLTMGZMH-UHFFFAOYSA-N 0.000 description 1
- UBCNRIRGGVGRGZ-UHFFFAOYSA-N propyl 2-amino-5-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC(O)=CC=C1N UBCNRIRGGVGRGZ-UHFFFAOYSA-N 0.000 description 1
- HZMHKHMBXSCSRJ-UHFFFAOYSA-N propyl 3-amino-4-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC=C(O)C(N)=C1 HZMHKHMBXSCSRJ-UHFFFAOYSA-N 0.000 description 1
- BGAFTBFFBLVMCB-UHFFFAOYSA-N propyl 4-amino-2-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC=C(N)C=C1O BGAFTBFFBLVMCB-UHFFFAOYSA-N 0.000 description 1
- JJJQBGKJGCEVDB-UHFFFAOYSA-N propyl 5-amino-2-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC(N)=CC=C1O JJJQBGKJGCEVDB-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-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
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HNCWUFDGDNZDLY-UHFFFAOYSA-L zinc;2-carboxy-5-[2-(4-methoxyphenoxy)ethoxy]phenolate Chemical compound [Zn+2].C1=CC(OC)=CC=C1OCCOC1=CC=C(C(O)=O)C([O-])=C1.C1=CC(OC)=CC=C1OCCOC1=CC=C(C(O)=O)C([O-])=C1 HNCWUFDGDNZDLY-UHFFFAOYSA-L 0.000 description 1
- IPCXNCATNBAPKW-UHFFFAOYSA-N zinc;hydrate Chemical compound O.[Zn] IPCXNCATNBAPKW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
2個のR2は、それぞれ独立して、水素原子;または-S(=O)2R3(R3は、無置換、または、炭素数1~12のアルキル基若しくは炭素数1~8のアルコキシ基でそれぞれ置換された、炭素数7~12のアラルキル基または炭素数6~14のアリール基である。)で表される基である。)
で表される化合物(以下、「本発明の化合物」または「本発明のウレイレン-ジ(ヒドロキシ安息香酸エステル)誘導体」と称することもある。)。
[2]一般式(1)の化合物が、下記一般式(2)
で表される化合物である、前記[1]に記載の化合物。
[3]一般式(2)の化合物が、下記式(3)
[4]前記[1]~[3]のいずれかに記載の化合物を含有する顕色剤。
[5]前記[1]~[3]のいずれかに記載の化合物を含有する感熱記録塗料。
[6]前記[1]~[3]のいずれかに記載の化合物を含有する感熱記録層。
[7]前記[5]に記載の感熱記録塗料を支持体に塗布してなる感熱記録体。
[8]前記[5]に記載の感熱記録塗料を支持体に塗布してなる感熱記録材料。
[9]支持体が、紙、プラスティックフィルム、または加工紙である前記[7]に記載の感熱記録体。
[10]支持体が、紙、プラスティックフィルム、または加工紙である前記[8]に記載の感熱記録材料。
[11]常温で無色ないし淡色の塩基性染料と、加熱により該塩基性染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、前記顕色剤として、前記[1]~[3]のいずれかに記載の化合物を含有することを特徴とする感熱記録材料。
[12]顕色剤として、前記[1]~[3]のいずれかに記載の化合物と、非フェノール顕色剤及びフェノール系顕色剤からなる群より選択される顕色剤を併用することを特徴とする、前記[11]に記載の感熱記録材料。
本発明のウレイレン-ジ(ヒドロキシ安息香酸エステル)誘導体は、前記一般式(1)~(2)で表される。
本発明の一般式(1)で表されるウレイレン-ジ(ヒドロキシ安息香酸エステル)誘導体は、各種方法により合成することができる。例えば、一般式(8)の化合物は、下記反応式(1)で示される様に、一般式(7)で表されるアミノ置換されたヒドロキシ安息香酸エステル化合物に尿素結合形成試剤(例えば、尿素あるいはホスゲン、およびホスゲン誘導体、具体的にはトリホスゲン、カルボニルビスイミダゾール、N-置換カルバミン酸エステル)を作用させて合成することができる。
(反応式2)
4-アミノ-3-ヒドロキシ安息香酸メチル、4-アミノ-3-ヒドロキシ安息香酸エチル、
本発明の感熱記録材料は、常温で無色ないし淡色の塩基性染料と、加熱により該塩基性染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、前記顕色剤として、本発明の化合物を含有することを特徴とする。また、本発明の化合物は、既存の顕色剤と併用して用いてもよく、既存の顕色剤と併用して用いる場合、本発明の化合物は、既存顕色剤と任意の割合で用いる事ができ、既存の顕色剤の保存性能を補填する顕色機能を有する保存向上剤としても活用できる。
下塗り層の組成は、目的により適宜選択すればよいが、一般に、バインダー、顔料等が含まれる。
プラスチック中空粒子(商品名:ローペイクSN-1055:中空率:55体積%、固形分26.5%)100部、焼成カオリンの50%分散液100部、スチレン-ブタジエン系ラテックス(商品名:L-1571 固形分48%)25部、酸化澱粉の10%水溶液50部、および水20部を混合して、アンダーコート用塗料を作成した。
[感熱記録塗料の作成]
A液(染料分散液の調製)
3-(N,N-ジブチルアミノ)-6-メチル-7-アニリノフルオラン
10部
10%ポリビニルアルコール水溶液 10部
水 16.7部
4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)
安息香酸メチル](合成例3) 20部
10%ポリビニルアルコール水溶液 20部
水 33.3部
1,2-ビス(m-トリルオキシ)エタン 15部
10%ポリビニルアルコール水溶液 15部
水 25部
A液(染料剤分散液) 36.7部
B液(顕色剤分散液) 73.3部
C液(増感剤分散液) 55.0部
支持体として坪量が53g/m2の上質紙にアンダーコート用塗料を乾燥後の面積当たりの質量が6g/m2となるように塗布、および乾燥し、その後、感熱記録塗料を、乾燥後の面積当たりの質量が3.8g/m2になるように塗布乾燥した。このシートをスーパーカレンダーで平滑度(JISP8155:2010)が900~1200sになるように処理して感熱記録材料を作成し、各種試験(感熱記録性試験(発色試験)、耐湿熱性試験、耐熱性試験、耐水性試験(2種類の試験法による)、および耐可塑剤性試験を下記記載の方法により実施した。試験結果は、表1に記載の通りであった。
作成した感熱記録材料について、感熱記録紙印字試験機(大倉電気社製TH-PMD)を用いて、印加エネルギー0.38mJ/dotで印加した。記録部の印字濃度と未印字部はマクベス反射濃度計RD-914で測定した。これを試験前サンプル(ブランク)とした。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を試験温度40℃、90%RHの環境下に24時間放置した後、試験片の画像濃度と未印字部の濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を試験温度60℃の恒温環境下に24時間放置した後、試験片の画像濃度と未印字部の濃度をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料を水中に15時間浸漬しその後、試験片を風乾させ、画像濃度と未印字部をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料にサラダオイル中に10分間浸漬しその後、試験片の油をふき取り、画像濃度と未印字部をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料にサラダオイル中に3時間浸漬し、その後、試験片の油をふき取り、画像濃度と未印字部をマクベス反射濃度計で測定した。
感熱記録性試験で印加エネルギー0.38mJ/dotで記録した感熱記録材料に、ポリカーボネートパイプ(48mmφ)上にラップフィルム(商品名:ハイラップ(登録商標)KMA、三井化学製)を3重に巻き付け、感熱記録材料を乗せ、更にその上にラップフィルムを3重に巻き付け20℃、65%RHの環境下で24時間放置し、その後、画像濃度と未印字部をマクベス反射濃度計で測定した。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)を4,4’-ウレイレン-ジ[2-(p-トルエンスルホニルオキシ)安息香酸メチル](合成例2)に代えた以外は、実施例1と同様の操作をおこなった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)を4,4’-ウレイレン-ジ[2-(2-ナフタレンスルホニルオキシ)安息香酸メチル](合成例4)に代えた以外は、実施例1と同様の操作をおこなった。この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)を4,4’-ウレイレン-ジ[2-(ベンゼンスルホニルオキシ)安息香酸メチル](合成例6)に代えた以外は、実施例1と同様の操作をおこなった。この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)を4,4’-ウレイレン-ジ[2-(o-トルエンスルホニルオキシ)安息香酸メチル](合成例5)に代えた以外は、実施例1と同様の操作をおこなった。この実施例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)をN-3-[(p-トルエンスルホニル)オキシ]フェニル-N’-(p-トルエンスルホニル)-尿素に代えた以外は、実施例1と同様の操作をおこなった。この比較例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)をN-(2-(3-フェニルウレイド)フェニル)ベンゼンスルホンアミドに代えた以外は、実施例1と同様の操作をおこなった。この比較例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)をN-3-[(p-トルエンスルホニル)オキシ]フェニル-N’-フェニル-尿素に代えた以外は、実施例1と同様の操作をおこなった。この比較例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)をN,N’-ジ-[3-(p-トルエンスルホニルオキシ)フェニル]尿素に代えた以外は、実施例1と同様の操作をおこなった。この比較例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)をビスフェノールAに代えた以外は、実施例1と同様の操作をおこなった。この比較例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
実施例1のB液の4,4’-ウレイレン-ジ[2-(1-ナフタレンスルホニルオキシ)安息香酸メチル](合成例3)をビスフェノールSに代えた以外は、実施例1と同様の操作をおこなった。この比較例による感熱記録材料の各種試験結果は、表1に記載の通りであった。
Claims (10)
- 一般式(1)
(式中、2個のR1は、それぞれ独立して、炭素数1~12の直鎖状、分岐鎖状、若しくは脂環状のアルキル基;炭素数7~12のアラルキル基;または炭素数6~14のアリール基であり、
2個のR2は、それぞれ独立して、-S(=O)2R3(R3は、無置換、または、炭素数1~12のアルキル基若しくは炭素数1~8のアルコキシ基でそれぞれ置換された、炭素数7~12のアラルキル基または炭素数6~14のアリール基である。)で表される基である。)
で表される化合物。 - 一般式(1)の化合物が、下記一般式(2)
(R3は、請求項1で定義したものと同義である。)
で表される化合物である、請求項1に記載の化合物。 - 一般式(2)の化合物が、下記式(3)
、式(4)
、式(5)
、および式(6)
のいずれかで表される化合物である、請求項2に記載の化合物。 - 請求項1~3のいずれか一項に記載の化合物を含有する顕色剤。
- 請求項1~3のいずれか一項に記載の化合物を含有する感熱記録塗料。
- 請求項1~3のいずれか一項に記載の化合物を含有する感熱記録層。
- 請求項5に記載の感熱記録塗料を支持体に塗布してなる感熱記録体。
- 支持体が、紙、プラスティックフィルム、または加工紙である、請求項7に記載の感熱記録体。
- 常温で無色ないし淡色の塩基性染料と、加熱により該塩基性染料と接触して呈色し得る顕色剤とを含有する感熱記録層を支持体上に設けた感熱記録材料であって、前記顕色剤として、請求項1~3のいずれか一項に記載の化合物を含有することを特徴とする感熱記録材料。
- 顕色剤として、請求項1~3のいずれか一項に記載の化合物と、非フェノール顕色剤及びフェノール系顕色剤からなる群より選択される顕色剤を併用することを特徴とする、請求項9に記載の感熱記録材料。
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Collection of Czechoslovak Chemical Communications,1968年,Vol.33, No.6,p.1948-54 |
Database REGISTRY [online] ,2015年,RN 860510-27-6,(検索日:2023年8月1日) |
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