JP3019728B2 - Pressure-sensitive recording material - Google Patents
Pressure-sensitive recording materialInfo
- Publication number
- JP3019728B2 JP3019728B2 JP6212132A JP21213294A JP3019728B2 JP 3019728 B2 JP3019728 B2 JP 3019728B2 JP 6212132 A JP6212132 A JP 6212132A JP 21213294 A JP21213294 A JP 21213294A JP 3019728 B2 JP3019728 B2 JP 3019728B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- bis
- diethylaminofluoran
- sensitive recording
- pressure
- 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
- 239000000463 material Substances 0.000 title claims description 21
- -1 2,6-dimethylanilino Chemical group 0.000 claims description 50
- 239000000975 dye Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- CRKAWLFCMDKQIT-UHFFFAOYSA-N 6-(dimethylamino)-3h-2-benzofuran-1-one Chemical compound CN(C)C1=CC=C2COC(=O)C2=C1 CRKAWLFCMDKQIT-UHFFFAOYSA-N 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 30
- 238000001454 recorded image Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 14
- IPAJDLMMTVZVPP-UHFFFAOYSA-N Crystal violet lactone Chemical compound C1=CC(N(C)C)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 IPAJDLMMTVZVPP-UHFFFAOYSA-N 0.000 description 12
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
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- 239000002775 capsule Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical class C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 3
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- 239000006096 absorbing agent Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 229940043267 rhodamine b Drugs 0.000 description 3
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- 239000000654 additive Substances 0.000 description 2
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- 150000003951 lactams Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UFRKOOMLVWDICO-UHFFFAOYSA-N n-ethyl-n-fluoroethanamine Chemical compound CCN(F)CC UFRKOOMLVWDICO-UHFFFAOYSA-N 0.000 description 2
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- 239000005011 phenolic resin Substances 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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- VNFXPOAMRORRJJ-UHFFFAOYSA-N (4-octylphenyl) 2-hydroxybenzoate Chemical compound C1=CC(CCCCCCCC)=CC=C1OC(=O)C1=CC=CC=C1O VNFXPOAMRORRJJ-UHFFFAOYSA-N 0.000 description 1
- SBKSKNZXWSOVSN-UHFFFAOYSA-N 1,2,2-trimethyl-3,4-dihydroquinoline Chemical compound C1=CC=C2CCC(C)(C)N(C)C2=C1 SBKSKNZXWSOVSN-UHFFFAOYSA-N 0.000 description 1
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- YGTMLPNHQMNCOW-UHFFFAOYSA-N 1-n,4-n-dimethyl-1-n-phenyl-4-n-propan-2-ylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C(C)C)=CC=C1N(C)C1=CC=CC=C1 YGTMLPNHQMNCOW-UHFFFAOYSA-N 0.000 description 1
- WQFYAGVHZYFXDO-UHFFFAOYSA-N 2'-anilino-6'-(diethylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 WQFYAGVHZYFXDO-UHFFFAOYSA-N 0.000 description 1
- HUSIBQLZEMMTCQ-UHFFFAOYSA-N 2'-anilino-6'-[ethyl(3-methylbutyl)amino]-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCC(C)C)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 HUSIBQLZEMMTCQ-UHFFFAOYSA-N 0.000 description 1
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- XPSDDCQPLUUXMQ-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-(2-ethylhexoxy)phenol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1N1N=C2C=CC=CC2=N1 XPSDDCQPLUUXMQ-UHFFFAOYSA-N 0.000 description 1
- VQMHSKWEJGIXGA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-dodecyl-4-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O VQMHSKWEJGIXGA-UHFFFAOYSA-N 0.000 description 1
- NZGISXRFQUEWAS-UHFFFAOYSA-N 2-tert-butyl-4-(3-tert-butyl-5-chloro-4-hydroxyphenyl)sulfanyl-6-chlorophenol Chemical compound ClC1=C(O)C(C(C)(C)C)=CC(SC=2C=C(C(O)=C(Cl)C=2)C(C)(C)C)=C1 NZGISXRFQUEWAS-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- YKUUUTAPMKKPTK-UHFFFAOYSA-N 2-tert-butyl-6-[2-(3-tert-butyl-2-hydroxy-5-methylphenyl)ethyl]-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(CCC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O YKUUUTAPMKKPTK-UHFFFAOYSA-N 0.000 description 1
- GRIKUIPJBHJPPN-UHFFFAOYSA-N 3',6'-dimethoxyspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(OC)C=C1OC1=CC(OC)=CC=C21 GRIKUIPJBHJPPN-UHFFFAOYSA-N 0.000 description 1
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- CONFUNYOPVYVDC-UHFFFAOYSA-N 3,3-bis(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=C(C)N(C4=CC=CC=C43)CC)=C(C)N(CC)C2=C1 CONFUNYOPVYVDC-UHFFFAOYSA-N 0.000 description 1
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- CRXPGHGHRBXGLG-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxyphenyl]-3-(2-methyl-1-octylindol-3-yl)-2-benzofuran-1-one Chemical compound C12=CC=CC=C2N(CCCCCCCC)C(C)=C1C1(C2=CC=CC=C2C(=O)O1)C1=CC=C(N(CC)CC)C=C1OCC CRXPGHGHRBXGLG-UHFFFAOYSA-N 0.000 description 1
- GNZQDEXHTZDQRB-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methylphenyl]-6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-2-benzofuran-1-one Chemical compound CC1=CC(N(CC)CC)=CC=C1C1(C=2C=CC(=CC=2)N(C)C)C2=CC=C(N(C)C)C=C2C(=O)O1 GNZQDEXHTZDQRB-UHFFFAOYSA-N 0.000 description 1
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- MKUFYFMMYBYVQL-UHFFFAOYSA-N 6'-[cyclohexyl(methyl)amino]-2'-[4-[2-[4-[[6'-[cyclohexyl(methyl)amino]-3'-methyl-3-oxospiro[2-benzofuran-1,9'-xanthene]-2'-yl]amino]phenyl]propan-2-yl]anilino]-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C=C(C2(C3=CC=CC=C3C(=O)O2)C2=CC(NC=3C=CC(=CC=3)C(C)(C)C=3C=CC(NC=4C(=CC5=C(C6(C7=CC=CC=C7C(=O)O6)C6=CC=C(C=C6O5)N(C)C5CCCCC5)C=4)C)=CC=3)=C(C)C=C2O2)C2=CC=1N(C)C1CCCCC1 MKUFYFMMYBYVQL-UHFFFAOYSA-N 0.000 description 1
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- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
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- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000004305 biphenyl Substances 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001739 density measurement Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 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 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- ABRBLBAAGMWTBY-UHFFFAOYSA-N n-chloro-n-fluorocyclohexanamine Chemical compound FN(Cl)C1CCCCC1 ABRBLBAAGMWTBY-UHFFFAOYSA-N 0.000 description 1
- FIIGZGVXXBOCPL-UHFFFAOYSA-N n-fluoro-3-methylcyclohexan-1-amine Chemical compound CC1CCCC(NF)C1 FIIGZGVXXBOCPL-UHFFFAOYSA-N 0.000 description 1
- JDTGFAQFXZGQQE-UHFFFAOYSA-N n-fluoro-n,2-dimethylpropan-1-amine Chemical compound CC(C)CN(C)F JDTGFAQFXZGQQE-UHFFFAOYSA-N 0.000 description 1
- PIIHPBHYDCOPKZ-UHFFFAOYSA-N n-fluoro-n-methylmethanamine Chemical compound CN(C)F PIIHPBHYDCOPKZ-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Color Printing (AREA)
Description
【0001】[0001]
【産業上の利用分野】本願発明は記録画像の色調及び耐
光堅牢度、耐NOx堅牢度に優れる感圧記録材料に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pressure-sensitive recording material which is excellent in color tone, light fastness and NOx fastness of a recorded image.
【0002】[0002]
【従来の技術】電子供与性ロイコ色素(以下ロイコ色素
という)と電子受容性顕色剤(以下顕色剤という)との
発色反応を利用する感圧記録材料は広く普及している。2. Description of the Related Art Pressure-sensitive recording materials utilizing a color development reaction between an electron-donating leuco dye (hereinafter referred to as "leuco dye") and an electron-accepting developer (hereinafter referred to as "developer") are widely used.
【0003】現在、記録画像が黒色の感圧記録材料には
ロイコ色素として一般式(I)At present, a pressure-sensitive recording material having a black recorded image has a general formula (I) as a leuco dye.
【化1】 (式中、Xは置換アミノ基を示す。)で表されるフルオ
ラン化合物が主として用いられている。Embedded image (In the formula, X represents a substituted amino group.) A fluoran compound represented by the following formula is mainly used.
【0004】一般式(I) で表されるフルオラン化合物
を用いた感圧記録材料は一般に、その記録画像が光によ
り赤色に変色する欠点がある。A pressure-sensitive recording material using a fluoran compound represented by the general formula (I) generally has a disadvantage that the recorded image turns red by light.
【0005】特開昭63−192777号公報は一般式
(II)JP-A-63-192777 discloses a compound of the general formula (II)
【化2】 (式中、Yは置換アミノ基、R1、R2は個別に低級アル
キル基を示す。)で表されるフルオラン化合物を開示
し、該フルオラン化合物を用いた黒色記録画像は赤色変
化が小さいことを記載している。Embedded image (Wherein, Y represents a substituted amino group, and R 1 and R 2 each independently represent a lower alkyl group.) A fluoran compound represented by the formula: Is described.
【0006】また、特開平1−150574号公報は一
般式(III)JP-A-1-150574 discloses a compound represented by the general formula (III):
【化3】 (式中、Zは置換アミノ基を示す。)で表されるフルオ
ラン化合物を用いた黒色記録画像は赤色変化が小さいこ
とを開示している。Embedded image (In the formula, Z represents a substituted amino group.) It is disclosed that a black recorded image using a fluoran compound represented by the formula (1) has a small red change.
【0007】一般式(II)あるいは一般式(III)で表
されるフルオラン化合物を用いた黒色記録画像は赤色変
化の程度自体は小さいものであるが、その元来の色調
は、一般式(I)で表されるフルオラン化合物を用いた
黒色記録画像の色調より赤味であり、又、画像濃度が十
分でないと言う欠点がある。A black recorded image using the fluoran compound represented by the general formula (II) or (III) has a small degree of red change, but its original color tone is represented by the general formula (I ) Has a disadvantage that the color tone of the black recorded image using the fluoran compound is reddish and the image density is not sufficient.
【0008】従って、初期の発色色調が純黒色であり、
その濃度が高く、且つ光によって色調が変化しない感圧
記録材料に対する期待が大きい。Accordingly, the initial color tone is pure black,
There is great expectation for pressure-sensitive recording materials whose density is high and whose color tone does not change with light.
【0009】また、最近では記録画像がNOx(窒素酸
化物)により赤変する現象も問題となっており、耐NO
x堅牢度の高い感圧記録材料が求められている。Recently, a phenomenon that a recorded image turns red due to NOx (nitrogen oxide) has also become a problem.
There is a need for a pressure-sensitive recording material having high x-fastness.
【0010】[0010]
【発明が解決しようとする課題】本発明の目的は、記録
画像の色調が純黒色であり、記録画像濃度が高く、且つ
画像の光やNOxによる赤色変化が小さい感圧記録材料
を提供する事にある。SUMMARY OF THE INVENTION An object of the present invention is to provide a pressure-sensitive recording material in which the color tone of a recorded image is pure black, the density of the recorded image is high, and the red color change due to image light or NOx is small. It is in.
【0011】[0011]
【課題を解決するための手段】本発明の課題は、特定の
2種のロイコ色素を併用する事により達成された。The object of the present invention has been attained by using two specific leuco dyes in combination.
【0012】即ち、本発明は電子供与性ロイコ色素と電
子受容性顕色剤との発色反応を利用する感圧記録材料に
於いて、全電子供与性ロイコ色素のうち98〜80重量
%が2−(2,6−ジメチルアニリノ)−3−メチル−
6−ジエチルアミノフルオランであり、2〜10重量%
が3,3−ビス(4−ジメチルアミノフェニル)−6−
ジメチルアミノフタリドである感圧記録材料を提供する
ものである。That is, the present invention relates to an electron-donating leuco dye
Pressure-sensitive recording material utilizing color development reaction with an acceptor color developer
98-80% by weight of the total electron donating leuco dye
% Is 2- (2,6-dimethylanilino) -3-methyl-
6-diethylaminofluoran, 2 to 10% by weight
Is 3,3-bis (4-dimethylaminophenyl) -6
It is intended to provide a pressure-sensitive recording material which is dimethylaminophthalide .
【0013】上記2種の電子供与性ロイコ色素の使用量
は好ましくは、全電子供与性ロイコ色素中、2−(2,
6−ジメチルアニリノ)−3−メチル−6−ジエチルア
ミノフルオランが97〜85重量%であり、3,3−ビ
ス(4−ジメチルアミノフェニル)−6−ジメチルアミ
ノフタリドが3〜8重量%である。 The amount of the two electron-donating leuco dyes used is preferably 2- (2,2,
6-dimethylanilino) -3-methyl-6-diethylaminofluoran is 97 to 85% by weight, and 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide is 3 to 8% by weight. It is.
【0014】全電子供与性ロイコ色素中、2−(2,6
−ジメチルアニリノ)−3−メチル−6−ジエチルアミ
ノフルオランが80重量%より少ない場合は、記録画像
の光による赤変度が大きくなる場合がある。Among all electron donating leuco dyes, 2- (2,6
When the content of (-dimethylanilino) -3-methyl-6-diethylaminofluorane is less than 80% by weight, the redness of a recorded image due to light may increase.
【0015】全電子供与性ロイコ色素中、3,3−ビス
(4−ジメチルアミノフェニル)−6−ジメチルアミノ
フタリドが2重量%より少ない場合は、記録画像の濃度
が十分に得られず、かつ純黒色の色調が得られない場合
がある。また、10重量%より多い場合は、純黒色の記
録画像が得られない場合がある。When the amount of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide in all the electron donating leuco dyes is less than 2% by weight, a sufficient density of a recorded image cannot be obtained. In addition, a pure black color tone may not be obtained. If the content is more than 10% by weight, a pure black recorded image may not be obtained.
【0016】また、2−(2,6−ジメチルアニリノ)
−3−メチル−6−ジエチルアミノフルオランと3,3
−ビス(4−ジメチルアミノフェニル)−6−ジメチル
アミノフタリドの合計量が全電子供与性ロイコ色素の8
2%より少ない場合は、目的とする記録画像の色調およ
び耐赤変性が同時に達成されない場合がある。Also, 2- (2,6-dimethylanilino)
-3-methyl-6-diethylaminofluoran and 3,3
The total amount of -bis (4-dimethylaminophenyl) -6-dimethylaminophthalide is 8% of the total electron donating leuco dye.
If the amount is less than 2%, the intended color tone and resistance to reddening of the recorded image may not be achieved at the same time.
【0017】本発明の感圧記録材料に於いて、必要に応
じて、本発明の特性を阻害しない範囲で更に他のロイコ
色素を併用することが出来る。In the pressure-sensitive recording material of the present invention, if necessary, other leuco dyes can be used in combination as long as the characteristics of the present invention are not impaired.
【0018】これらの一部を例示すれば、フルオラン系
化合物としては、3,6−ジメトキシフルオラン、2−
クロロ−6−シクロヘキシルアミノフルオラン、3−ク
ロロ−6−シクロヘキシルアミノフルオラン、2−メチ
ル−6−シクロヘキシルアミノフルオラン、3−メチル
−6−シクロヘキシルアミノフルオラン、1,3−ジメ
チル−6−ジエチルアミノフルオラン、2−tert−
ブチル−6−ジエチルアミノフルオラン、2−クロロ−
6−ジエチルアミノフルオラン、Examples of these fluoran compounds include 3,6-dimethoxyfluoran,
Chloro-6-cyclohexylaminofluoran, 3-chloro-6-cyclohexylaminofluoran, 2-methyl-6-cyclohexylaminofluoran, 3-methyl-6-cyclohexylaminofluoran, 1,3-dimethyl-6 Diethylaminofluoran, 2-tert-
Butyl-6-diethylaminofluoran, 2-chloro-
6-diethylaminofluoran,
【0019】2−クロロ−3−メチル−6−ジエチルア
ミノフルオラン、2−メチル−6−(N−エチル−4−
メチルアニリノ)フルオラン、8−ジエチルアミノベン
ゾ[a]フルオラン、2−ジベンジルアミノ−6−ジエ
チルアミノフルオラン、2−ジベンジルアミノ−4−メ
チル−6−ジエチルアミノフルオラン、2−n−オクチ
ルアミノ−6−ジエチルアミノフルオラン、2−アニリ
ノ−6−(N−エチル−N−n−ヘキシルアミノ)フル
オラン、2-chloro-3-methyl-6-diethylaminofluoran, 2-methyl-6- (N-ethyl-4-
Methylanilino) fluoran, 8-diethylaminobenzo [a] fluoran, 2-dibenzylamino-6-diethylaminofluoran, 2-dibenzylamino-4-methyl-6-diethylaminofluoran, 2-n-octylamino-6 Diethylaminofluoran, 2-anilino-6- (N-ethyl-Nn-hexylamino) fluoran,
【0020】2−(N−メチルアニリノ)−6−(N−
エチル−4−メチルアニリノ)フルオラン、2−クロロ
−3−メチル−6−[4−(4−アニリノアニリノ)ア
ニリノ]フルオラン、2−アニリノ−3−メチル−6−
ジメチルアミノフルオラン、2−アニリノ−3−メチル
−6−ジエチルアミノフルオラン、2−アニリノ−3−
メチル−6−ジ−n−プロピルアミノフルオラン、2−
アニリノ−3−メチル−6−ジ−n−ブチルアミノフル
オラン、2−アニリノ−3−メチル−6−ジ−n−ペン
チルアミノフルオラン、2−アニリノ−3−メチル−6
−(N−メチル−N−エチルアミノ)フルオラン、2- (N-methylanilino) -6- (N-
Ethyl-4-methylanilino) fluoran, 2-chloro-3-methyl-6- [4- (4-anilinoanilino) anilino] fluoran, 2-anilino-3-methyl-6
Dimethylaminofluoran, 2-anilino-3-methyl-6-diethylaminofluoran, 2-anilino-3-
Methyl-6-di-n-propylaminofluoran, 2-
Anilino-3-methyl-6-di-n-butylaminofluoran, 2-anilino-3-methyl-6-di-n-pentylaminofluoran, 2-anilino-3-methyl-6
-(N-methyl-N-ethylamino) fluoran,
【0021】2−アニリノ−3−メチル−6−(N−メ
チル−N−n−プロピルアミノ)フルオラン、2−アニ
リノ−3−メチル−6−(N−メチル−N−n−ブチル
アミノ)フルオラン、2−アニリノ−3−メチル−6−
(N−メチル−N−イソブチルアミノ)フルオラン、2
−アニリノ−3−メチル−6−(N−メチル−N−n−
ペンチルアミノ)フルオラン、2−アニリノ−3−メチ
ル−6−(N−メチル−N−シクロヘキシルアミノ)フ
ルオラン、2−アニリノ−3−メチル−6−(N−エチ
ル−N−n−プロピルアミノ)フルオラン、2−アニリ
ノ−3−メチル−6−(N−エチル−N−n−ブチルア
ミノ)フルオラン、2-anilino-3-methyl-6- (N-methyl-NN-propylamino) fluoran, 2-anilino-3-methyl-6- (N-methyl-NN-butylamino) fluoran , 2-anilino-3-methyl-6
(N-methyl-N-isobutylamino) fluoran, 2
-Anilino-3-methyl-6- (N-methyl-Nn-
(Pentylamino) fluoran, 2-anilino-3-methyl-6- (N-methyl-N-cyclohexylamino) fluoran, 2-anilino-3-methyl-6- (N-ethyl-N-n-propylamino) fluoran 2-anilino-3-methyl-6- (N-ethyl-Nn-butylamino) fluoran,
【0022】2−アニリノ−3−メチル−6−(N−エ
チル−N−イソブチルアミノ)フルオラン、2−アニリ
ノ−3−メチル−6−(N−エチル−N−n−ペンチル
アミノ)フルオラン、2−アニリノ−3−メチル−6−
(N−エチル−N−イソペンチルアミノ)フルオラン、
2−アニリノ−3−メチル−6−(N−エチル−N−n
−オクチルアミノ)フルオラン、2−アニリノ−3−メ
チル−6−[N−エチル−N−(3−エトキシプロピ
ル)アミノ]フルオラン、2−アニリノ−3−メチル−
6−(N−エチル−N−p−トリルアミノ)フルオラ
ン、2−アニリノ−3−クロロ−6−ジエチルアミノフ
ルオラン、2-anilino-3-methyl-6- (N-ethyl-N-isobutylamino) fluoran, 2-anilino-3-methyl-6- (N-ethyl-Nn-pentylamino) fluoran, 2 -Anilino-3-methyl-6-
(N-ethyl-N-isopentylamino) fluoran,
2-anilino-3-methyl-6- (N-ethyl-Nn
-Octylamino) fluoran, 2-anilino-3-methyl-6- [N-ethyl-N- (3-ethoxypropyl) amino] fluoran, 2-anilino-3-methyl-
6- (N-ethyl-Np-tolylamino) fluoran, 2-anilino-3-chloro-6-diethylaminofluoran,
【0023】2−アニリノ−3−クロロ−6−ジ−n−
ブチルアミノフルオラン、2−(2−クロロアニリノ)
−6−ジエチルアミノフルオラン、2−(2−クロロア
ニリノ)−6−ジ−n−ブチルアミノフルオラン、2−
(2−フルオロアニリノ)−6−ジエチルアミノフルオ
ラン、2−(2−フルオロアニリノ)−6−ジ−n−ブ
チルアミノフルオラン、2−(3−トリフルオロメチル
アニリノ)−6−ジメチルアミノフルオラン、2−(3
−トリフルオロメチルアニリノ)−6−ジエチルアミノ
フルオラン、2-anilino-3-chloro-6-di-n-
Butylaminofluoran, 2- (2-chloroanilino)
-6-diethylaminofluoran, 2- (2-chloroanilino) -6-di-n-butylaminofluoran, 2-
(2-fluoroanilino) -6-diethylaminofluoran, 2- (2-fluoroanilino) -6-di-n-butylaminofluoran, 2- (3-trifluoromethylanilino) -6-dimethyl Aminofluoran, 2- (3
-Trifluoromethylanilino) -6-diethylaminofluoran,
【0024】2−(3−トリフルオロメチルアニリノ)
−6−ジ−n−ブチルアミノフルオラン、2−(3−メ
チルアニリノ)−3−メチル−6−ジエチルアミノフル
オラン、2−(3−メチルアニリノ)−3−メチル−6
−ジ−n−ブチルアミノフルオラン、2−(4−メチル
アニリノ)−3−メチル−6−ジエチルアミノフルオラ
ン、2−(4−t−アミルアニリノ)−3−メチル−6
−ジエチルアミノフルオラン、2−(3−クロロ−4−
メチルアニリノ)−3−メチル−6−ジエチルアミノフ
ルオラン、2−(2,4−ジメチルアニリノ)−3−メ
チル−6−ジエチルアミノフルオラン、2- (3-trifluoromethylanilino)
-6-di-n-butylaminofluoran, 2- (3-methylanilino) -3-methyl-6-diethylaminofluoran, 2- (3-methylanilino) -3-methyl-6
-Di-n-butylaminofluoran, 2- (4-methylanilino) -3-methyl-6-diethylaminofluoran, 2- (4-t-amylanilino) -3-methyl-6
-Diethylaminofluoran, 2- (3-chloro-4-
Methylanilino) -3-methyl-6-diethylaminofluoran, 2- (2,4-dimethylanilino) -3-methyl-6-diethylaminofluoran,
【0025】2−(2,4−ジメチルアニリノ)−3−
メチル−6−ジ−n−ブチルアミノフルオラン、2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジ−
n−ブチルアミノフルオラン、2−(2,6−ジエチル
アニリノ)−3−メチル−6−ジエチルアミノフルオラ
ン、2−(2,6−ジエチルアニリノ)−3−メチル−
6−ジ−n−ブチルアミノフルオラン,2−アニリノ−
3−メトキシ−6−ジエチルアミノフルオラン、2,2
−ビス{4−[6’−(N−シクロヘキシル−N−メチ
ルアミノ)−3’−メチルスピロ(フタリド−3,9’
−キサンテン)−2’−イルアミノ]フェニル}プロパ
ン等が、2- (2,4-dimethylanilino) -3-
Methyl-6-di-n-butylaminofluoran, 2-
(2,6-dimethylanilino) -3-methyl-6-di-
n-butylaminofluoran, 2- (2,6-diethylanilino) -3-methyl-6-diethylaminofluoran, 2- (2,6-diethylanilino) -3-methyl-
6-di-n-butylaminofluoran, 2-anilino-
3-methoxy-6-diethylaminofluoran, 2,2
-Bis {4- [6 '-(N-cyclohexyl-N-methylamino) -3'-methylspiro (phthalide-3,9'
-Xanthen) -2'-ylamino] phenyl} propane and the like;
【0026】ジアリールフタリド系化合物としては、
3,3−ビス(4−ジメチルアミノフェニル)フタリ
ド、3−(4−ジメチルアミノフェニル)−3−(4−
ジエチルアミノ−2−メチルフェニル)−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)−6−ジメチルアミノフタリド、3−
(4−ジメチルアミノフェニル)−3−(1−メチルピ
ロール−3−イル)−6−ジメチルアミノフタリド等
が、As the diarylphthalide compound,
3,3-bis (4-dimethylaminophenyl) phthalide, 3- (4-dimethylaminophenyl) -3- (4-
Diethylamino-2-methylphenyl) -6-dimethylaminophthalide, 3,3-bis (9-ethylcarbazol-3-yl) -6-dimethylaminophthalide, 3-
(4-dimethylaminophenyl) -3- (1-methylpyrrol-3-yl) -6-dimethylaminophthalide and the like,
【0027】インドリルフタリド系化合物としては、3
−(4−ジメチルアミノフェニル)−3−(1,2−ジ
メチルインドール−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)−6−ジメ
チルアミノフタリド、3,3−ビス(1−エチル−2−
メチルインドール−3−イル)フタリド、3,3−ビス
(1−n−ブチル−2−メチルインドール−3−イル)
フタリド、3,3−ビス(1−n−オクチル−2−メチ
ルインドール−3−イル)フタリド、3−(2−エトキ
シ−4−ジエチルアミノフェニル)−3−(1−エチル
−2−メチルインドール−3−イル)フタリド、3−
(2−エトキシ−4−ジブチルアミノフェニル)−3−
(1−エチル−2−メチルインドール−3−イル)フタ
リド、3−(2−エトキシ−4−ジエチルアミノフェニ
ル)−3−(1−オクチル−2−メチルインドール−3
−イル)フタリド等が、As the indolylphthalide compound, 3
-(4-dimethylaminophenyl) -3- (1,2-dimethylindol-3-yl) phthalide, 3,3-bis (1,2-dimethylindol-3-yl) -6-dimethylaminophthalide, 3,3-bis (1-ethyl-2-
Methylindol-3-yl) phthalide, 3,3-bis (1-n-butyl-2-methylindol-3-yl)
Phthalide, 3,3-bis (1-n-octyl-2-methylindol-3-yl) phthalide, 3- (2-ethoxy-4-diethylaminophenyl) -3- (1-ethyl-2-methylindole- 3-yl) phthalide, 3-
(2-ethoxy-4-dibutylaminophenyl) -3-
(1-ethyl-2-methylindole-3-yl) phthalide, 3- (2-ethoxy-4-diethylaminophenyl) -3- (1-octyl-2-methylindole-3
-Yl) phthalide, etc.
【0028】ビニローグフタリド系化合物としては、3
−(4−ジエチルアミノフェニル)−3−[2,2−ビ
ス(1−エチル−2−メチルインドール−3−イル)エ
テニル]フタリド、3,3−ビス[2−(4−ジメチル
アミノフェニル)−2−(4−メトキシフェニル)エテ
ニル]−4,5,6,7−テトラクロロフタリド、3,
3−ビス[2−(4−ピロリジノフェニル)−2−(4
−メトキシフェニル)エテニル]−4,5,6,7−テ
トラクロロフタリド、3,3−ビス[2,2−ビス(4
−ジメチルアミノフェニル)エテニル]−4,5,6,
7−テトラクロロフタリド、3,3−ビス[2,2−ビ
ス(4−ピロリジノフェニル)エテニル]−4,5,
6,7−テトラブロモフタリド等が、As vinylogous phthalide compounds, 3
-(4-Diethylaminophenyl) -3- [2,2-bis (1-ethyl-2-methylindol-3-yl) ethenyl] phthalide, 3,3-bis [2- (4-dimethylaminophenyl)- 2- (4-methoxyphenyl) ethenyl] -4,5,6,7-tetrachlorophthalide, 3,
3-bis [2- (4-pyrrolidinophenyl) -2- (4
-Methoxyphenyl) ethenyl] -4,5,6,7-tetrachlorophthalide, 3,3-bis [2,2-bis (4
-Dimethylaminophenyl) ethenyl] -4,5,6
7-tetrachlorophthalide, 3,3-bis [2,2-bis (4-pyrrolidinophenyl) ethenyl] -4,5
6,7-tetrabromophthalide and the like,
【0029】アザフタリド系化合物としては、3,3−
ビス(4−ジエチルアミノ−2−エトキシフェニル)−
4−アザフタリド、3−(4−ジエチルアミノ−2−エ
トキシフェニル)−3−[4−(N−エチル−N−フェ
ニルアミノ)−2−エトキシフェニル]−4−アザフタ
リド、3−(4−ジエチルアミノ−2−エトキシフェニ
ル)−3−(1−エチル−2−メチルインドール−3−
イル)−4−アザフタリド、3−(4−ジエチルアミノ
−2−エトキシフェニル)−3−(1−n−オクチル−
2−メチルインドール−3−イル)−4−アザフタリド
等が、The azaphthalide compounds include 3,3-
Bis (4-diethylamino-2-ethoxyphenyl)-
4-azaphthalide, 3- (4-diethylamino-2-ethoxyphenyl) -3- [4- (N-ethyl-N-phenylamino) -2-ethoxyphenyl] -4-azaphthalide, 3- (4-diethylamino- 2-ethoxyphenyl) -3- (1-ethyl-2-methylindole-3-
Yl) -4-azaphthalide, 3- (4-diethylamino-2-ethoxyphenyl) -3- (1-n-octyl-
2-methylindol-3-yl) -4-azaphthalide and the like,
【0030】ジアリールメタン系化合物としては、4,
4’−ビス(ジメチルアミノ)ベンズヒドリールベンジ
ルエーテル、N−ハロフェニルロイコオーラミン等が、
ローダミンラクタム系化合物としては、ローダミンBア
ニリノラクタム、ローダミンB(4−ニトロアニリノ)
ラクタム、ローダミンB(4−クロロアニリノ)ラクタ
ム等が、As the diarylmethane compound, 4,
4′-bis (dimethylamino) benzhydryl benzyl ether, N-halophenylleuco auramine, etc.
Rhodamine lactam compounds include rhodamine B anilino lactam and rhodamine B (4-nitroanilino)
Lactam, rhodamine B (4-chloroanilino) lactam and the like,
【0031】チアジン系化合物としては、ベンゾイルロ
イコメチレンブルー、p−ニトロベンゾイルロイコメチ
レンブルー等が、スピロピラン系化合物としては、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−フェニル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−プロピルスピロジベ
ンゾピラン等が、Examples of the thiazine compound include benzoyl leucomethylene blue and p-nitrobenzoyl leucomethylene blue, and examples of the spiropyran compound include 3-
Methylspirodinaphthopyran, 3-ethylspirodinaphthopyran, 3-phenylspirodinaphthopyran, 3-benzylspirodinaphthopyran, 3-propylspirodinaphthopyran and the like,
【0032】フルオレン系化合物としては、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−ジエチルアミノ−
6−(N−アリル−N−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)−スピロ[フルオレン−
9,6’−6’H−クロメノ(4,3−b)インドー
ル]、3,6−ビス(ジメチルアミノ)−3’−メチル
−スピロ[フルオレン−9,6’−6’H−クロメノ
(4,3−b)インドール]、3,6−ビス(ジエチル
アミノ)−3’−メチル−スピロ[フルオレン−9,
6’−6’H−クロメノ(4,3−b)インドール]等
が挙げられる。Examples of the fluorene compound include 3,6-bis (dimethylamino) fluorenespiro [9,3 ']-
6'-dimethylaminophthalide, 3-diethylamino-
6- (N-allyl-N-methylamino) fluorenespiro [9,3 ′]-6′-dimethylaminophthalide, 3,
6-bis (dimethylamino) -spiro [fluorene-
9,6′-6′H-chromeno (4,3-b) indole], 3,6-bis (dimethylamino) -3′-methyl-spiro [fluorene-9,6′-6′H-chromeno ( 4,3-b) indole], 3,6-bis (diethylamino) -3′-methyl-spiro [fluorene-9,
6'-6'H-chromeno (4,3-b) indole] and the like.
【0033】これらは単独で、あるいは2種以上混合し
て併用することができる。These can be used alone or in combination of two or more.
【0034】本発明の感圧記録材料を作成するには、例
えば特公昭42−20144号等に開示されている公知
の種々の方法により製造できる。一般的には、ロイコ色
素をカプセル化溶剤に溶解したロイコ色素溶液を、コア
セルベーション法、界面重合法、insitu重合法等の公知
のカプセル化法により、高分子化合物を膜剤としてカプ
セル化した後、上質紙、合成紙、プラスチックフィルム
等の支持体の裏面に塗布して上用紙を作成する。一方、
顕色剤を別の支持体の表面に塗布して下用紙を作成す
る。上用紙と下用紙を塗布面が接触するように重ね合わ
せて圧力を加えると、加圧された部分のカプセルが破壊
されてカプセル中のロイコ色素が顕色剤と反応し、下用
紙の表面に記録画像が形成される。また、支持体の表面
に顕色剤、裏面にカプセルを塗布した中用紙を上用紙と
下用紙の間に数枚挿入することにより、複数枚の複写記
録が得られる。また支持体の同一面に顕色剤とカプセル
を含有する、いわゆるセルフコンテインド紙タイプのも
の、或いは支持体中に顕色剤かカプセルの一方が含有さ
れ、他の一方が塗布された形態のものにも適用できる。The pressure-sensitive recording material of the present invention can be produced by various known methods disclosed in, for example, JP-B-42-20144. Generally, a leuco dye solution in which a leuco dye is dissolved in an encapsulating solvent is encapsulated as a polymer compound as a film agent by a known encapsulation method such as a coacervation method, an interfacial polymerization method, or an insitu polymerization method. After that, it is applied to the back surface of a support such as high-quality paper, synthetic paper, plastic film, etc. to form an upper paper. on the other hand,
A developer is applied to the surface of another support to form a lower sheet. When the upper paper and the lower paper are overlapped so that the coated surfaces are in contact with each other and pressure is applied, the capsule in the pressurized part is destroyed and the leuco dye in the capsule reacts with the developer, A recorded image is formed. In addition, a plurality of copy records can be obtained by inserting several sheets of middle paper coated with a developer on the front surface and a capsule on the back surface between the upper paper and the lower paper. Also, a so-called self-contained paper type containing a developer and a capsule on the same surface of the support, or a form in which one of the developer and the capsule is contained in the support and the other is coated It can be applied to things.
【0035】感圧記録材料に使用する顕色剤としては、
酸性白土、活性白土、アタパルジャイト、ゼオライト、
ベントナイト、カオリン等の無機系顕色剤、フェノール
性化合物、ノボラック型フェノール性樹脂あるいはその
多価金属塩、芳香族カルボン酸誘導体あるいはその多価
金属塩、サリチル酸誘導体あるいはその多価金属塩、サ
リチル酸樹脂あるいはその多価金属塩、テルペンフェノ
ール樹脂あるいはその多価金属塩等の有機系顕色剤が挙
げられる。As the developer used in the pressure-sensitive recording material,
Acid clay, activated clay, attapulgite, zeolite,
Inorganic developers such as bentonite and kaolin, phenolic compounds, novolak-type phenolic resins or polyvalent metal salts thereof, aromatic carboxylic acid derivatives or polyvalent metal salts thereof, salicylic acid derivatives or polyvalent metal salts thereof, salicylic acid resins Alternatively, an organic developer such as a polyvalent metal salt thereof, a terpene phenol resin or a polyvalent metal salt thereof may be used.
【0036】本発明の感圧記録材料は、公知の紫外線吸
収剤、酸化防止剤等の添加剤を併用しても良い。The pressure-sensitive recording material of the present invention may contain known additives such as an ultraviolet absorber and an antioxidant.
【0037】これらの添加剤の例としては、フェニルサ
リシレート、p−tert−ブチルフェニルサリシレー
ト、p−オクチルフェニルサリシレート等のサリチル酸
系紫外線吸収剤、2,4−ジヒドロキシベンゾフェノ
ン、2−ヒドロキシ−4−メトキシベンゾフェノン、2
−ヒドロキシ−4−ベンジルオキシベンゾフェノン、2
−ヒドロキシ−4−オクチルオキシベンゾフェノン、2
−ヒドロキシ−4−メトキシ−5−スルホベンゾフェノ
ン等のベンゾフェノン系紫外線吸収剤、2−(2−ヒド
ロキシ−5−メチルフェニル)ベンゾトリアゾール、2
−(2−ヒドロキシ−3−tert−ブチル−5−メチ
ルフェニル)−5−クロロベンゾトリアゾール、2−
(2−ヒドロキシ−3−ドデシル−5−メチルフェニ
ル)ベンゾトリアゾール、2−[2−ヒドロキシ−4−
(2−エチルヘキシル)オキシフェニル]ベンゾトリア
ゾール、メチル−3−[3−tert−ブチル−5−
(2H−ベンゾトリアゾール−2−イル)−4−ヒドロ
キシフェニル]プロピオネートとポリエチレングリコー
ルとの縮合物等のベンゾトリアゾール系紫外線吸収剤、Examples of these additives include salicylic acid type ultraviolet absorbers such as phenyl salicylate, p-tert-butylphenyl salicylate and p-octylphenyl salicylate, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxy Benzophenone, 2
-Hydroxy-4-benzyloxybenzophenone, 2
-Hydroxy-4-octyloxybenzophenone, 2
Benzophenone-based ultraviolet absorbers such as -hydroxy-4-methoxy-5-sulfobenzophenone, 2- (2-hydroxy-5-methylphenyl) benzotriazole,
-(2-hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole, 2-
(2-hydroxy-3-dodecyl-5-methylphenyl) benzotriazole, 2- [2-hydroxy-4-
(2-ethylhexyl) oxyphenyl] benzotriazole, methyl-3- [3-tert-butyl-5-
(2H-benzotriazol-2-yl) -4-hydroxyphenyl] benzotriazole-based ultraviolet absorber such as a condensate of propionate and polyethylene glycol,
【0038】2’−エチルヘキシル−2−シアノ−3,
3−ジフェニルアクリレート、エチル−2−シアノ−
3,3−ジフェニルアクリレート等のシアノアクリレー
ト系紫外線吸収剤、ビス(2,2,6,6,−テトラメ
チル−4−ピペリジル)セバケート、コハク酸−ビス
(2,2,6,6,−テトラメチル−4−ピペリジル)
エステル、2−(3,5−ジ−tert−ブチル)マロ
ン酸−ビス(1,2,2,6,6,−ペンタメチル−4
−ピペリジル)エステル等のヒンダードアミン系酸化防
止剤、2,2’−メチレンビス(4−メチル−6−te
rt−ブチルフェノール)、2,2’−エチレンビス
(4−メチル−6−tert−ブチルフェノール)、
2,2’−メチレンビス(4,6−ジ−tert−ブチ
ルフェノール)、4,4’−チオビス(3−メチル−6
−tert−ブチルフェノール)、4,4’−チオビス
(2−クロロ−6−tert−ブチルフェノール)等の
ヒンダードフェノール系酸化防止剤、2'-ethylhexyl-2-cyano-3,
3-diphenyl acrylate, ethyl-2-cyano-
Cyanoacrylate-based ultraviolet absorbers such as 3,3-diphenylacrylate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis-succinate-bis (2,2,6,6-tetra) Methyl-4-piperidyl)
Ester, 2- (3,5-di-tert-butyl) malonic acid-bis (1,2,2,6,6-pentamethyl-4
Hindered amine antioxidants such as -piperidyl) ester, 2,2'-methylenebis (4-methyl-6-te
rt-butylphenol), 2,2′-ethylenebis (4-methyl-6-tert-butylphenol),
2,2′-methylenebis (4,6-di-tert-butylphenol), 4,4′-thiobis (3-methyl-6
-Tert-butylphenol), hindered phenolic antioxidants such as 4,4′-thiobis (2-chloro-6-tert-butylphenol),
【0039】その他N−メチル−N−フェニル−N’−
メチル−N’−イソプロピル−p−フェニレンジアミ
ン、N−メチル−N−フェニル−N’−メチル−N’−
(1−メチルヘプチル)−p−フェニレンジアミン等の
p−フェニレンジアミン類、6−エトキシ−1−フェニ
ル−2,2,4−トリメチル−1,2−ジヒドロキノリ
ン、6−エトキシ−1−エチル−2,2,4−トリメチ
ル−1,2−ジヒドロキノリン、6−エトキシ−1−オ
クチル−2,2,4−トリメチル−1,2−ジヒドロキ
ノリン等のキノリン類、6−エトキシ−1−フェニル−
2,2,4−トリメチル−1,2,3,4−テトラヒド
ロキノリン、6−エトキシ−1−オクチル−2,2,4
−トリメチル−1,2,3,4−テトラヒドロキノリン
等のテトラヒドロキノリン類、4−メトキシ−ジ−n−
ブチルアニリン等のアニリン類等が挙げられる。Other N-methyl-N-phenyl-N'-
Methyl-N'-isopropyl-p-phenylenediamine, N-methyl-N-phenyl-N'-methyl-N'-
P-phenylenediamines such as (1-methylheptyl) -p-phenylenediamine, 6-ethoxy-1-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline, 6-ethoxy-1-ethyl- Quinolines such as 2,2,4-trimethyl-1,2-dihydroquinoline and 6-ethoxy-1-octyl-2,2,4-trimethyl-1,2-dihydroquinoline; 6-ethoxy-1-phenyl-
2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline, 6-ethoxy-1-octyl-2,2,4
-Tetrahydroquinolines such as trimethyl-1,2,3,4-tetrahydroquinoline, 4-methoxy-di-n-
Examples include anilines such as butylaniline.
【0040】3,3−ビス(4−ジメチルアミノフェニ
ル)−6−ジメチルアミノフタリドは従来、記録画像の
耐光堅牢度が低いことが知られているが、予想外にも2
−(2,6−ジメチルアニリノ)−3−メチル−6−ジ
エチルアミノフルオランと一定量の範囲で併用すること
により、十分な耐光堅牢度を示すことが発明者らにより
見い出された。It has been known that 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide has low light fastness of a recorded image, but unexpectedly,
It has been found by the present inventors that a sufficient light fastness is exhibited by using-(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran in combination within a certain amount.
【0041】尚、前記した特開平1−150574号公
報には、前記一般式(III)で表されるフルオラン化合
物に併用できる公知のロイコ色素の一例として、3,3
−ビス(4−アミノフェニル)−6−アミノフタリド等
の基本骨格を有する化合物の誘導体を挙げているが、2
−(2,6−ジメチルアニリノ)−3−メチル−6−ジ
エチルアミノフルオランと3,3−ビス(4−ジメチル
アミノフェニル)−6−ジメチルアミノフタリドを併用
することの具体的記載や実施例はなく、具体的な効果の
記載もない。Incidentally, JP-A-1-150574 mentioned above discloses 3,3 as an example of a known leuco dye which can be used in combination with the fluoran compound represented by the general formula (III).
Derivatives of compounds having a basic skeleton such as -bis (4-aminophenyl) -6-aminophthalide.
Specific description and implementation of the combined use of-(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide There is no example and no description of specific effects.
【0042】[0042]
【実施例】以下に、実施例により本発明を具体的に説明
するが、本発明は実施例に限定されるものではない。EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to the examples.
【0043】[実施例1]2−(2,6−ジメチルアニ
リノ)−3−メチル−6−ジエチルアミノフルオラン
1.9gと3,3−ビス(4−ジメチルアミノフェニ
ル)−6−ジメチルアミノフタリド0.1gをSAS−
296(日本石油化学製溶剤)47gに加熱下に溶解し
た。水100gに系変性剤5gを加え、苛性ソーダ水溶
液でpH4とした。これに前記の溶液およびメラミンホ
ルムアルデヒド初期重合物10gを加えて、ホモミキサ
ーで油滴が4ミクロンになるまで乳化した。次いで、撹
拌下に50℃に加熱し、1時間撹拌した。室温に冷却
後、25%アンモニア水でpH7.5に調節して、ロイ
コ色素のカプセル分散液を作成した。Example 1 1.9 g of 2- (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 3,3-bis (4-dimethylaminophenyl) -6-dimethylamino 0.1 g of phthalide to SAS-
This was dissolved in 47 g of 296 (solvent manufactured by Nippon Petrochemical) under heating. 5 g of a system modifier was added to 100 g of water, and the pH was adjusted to 4 with an aqueous sodium hydroxide solution. The above solution and 10 g of melamine formaldehyde prepolymer were added thereto, and the mixture was emulsified with a homomixer until oil droplets became 4 μm. Then, the mixture was heated to 50 ° C. with stirring and stirred for 1 hour. After cooling to room temperature, the pH was adjusted to 7.5 with 25% aqueous ammonia to prepare a capsule dispersion of the leuco dye.
【0044】このようにして調整したカプセル分散液1
0g、小麦粉澱粉2gおよびラテックス1gを良く混合
した後、秤量50g/m2の上質紙に固形分塗布量が5
g/m2となるように塗布し、白色の上用紙を作成し
た。The capsule dispersion liquid 1 thus prepared
0 g, 2 g of wheat starch and 1 g of latex were mixed well, and the amount of solids applied to fine paper of 50 g / m 2 was 5 g / m 2.
g / m 2 to produce white upper paper.
【0045】[実施例2]実施例1における、2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオラン1.9gと3,3−ビス(4−ジ
メチルアミノフェニル)−6−ジメチルアミノフタリド
0.1gの代わりに、2−(2,6−ジメチルアニリ
ノ)−3−メチル−6−ジエチルアミノフルオランを
1.86g、3,3−ビス(4−ジメチルアミノフェニ
ル)−6−ジメチルアミノフタリドを0.14g使用し
た以外は実施例1と同様の操作を行い、白色の上用紙を
作成した。[Example 2] In Example 1, 2-
Instead of 1.9 g of (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.1 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide, 2 g 1.86 g of-(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.14 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide were used. Except for the above, the same operation as in Example 1 was performed to produce a white upper sheet.
【0046】[実施例3]実施例1における、2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオラン1.9gと3,3−ビス(4−ジ
メチルアミノフェニル)−6−ジメチルアミノフタリド
0.1gの代わりに、2−(2,6−ジメチルアニリ
ノ)−3−メチル−6−ジエチルアミノフルオランを
1.78g、3,3−ビス(4−ジメチルアミノフェニ
ル)−6−ジメチルアミノフタリドを0.1g、2−
(2,4−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオランを0.12g使用した以外は実施
例1と同様の操作を行い、白色の上用紙を作成した。[Embodiment 3] In Embodiment 1, 2-
Instead of 1.9 g of (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.1 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide, 2 g 1.78 g of-(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran, 0.1 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide, −
The same operation as in Example 1 was carried out except that 0.12 g of (2,4-dimethylanilino) -3-methyl-6-diethylaminofluoran was used, to produce a white upper paper.
【0047】[実施例4]実施例1における、2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオラン1.9gと3,3−ビス(4−ジ
メチルアミノフェニル)−6−ジメチルアミノフタリド
0.1gの代わりに、2−(2,6−ジメチルアニリ
ノ)−3−メチル−6−ジエチルアミノフルオランを
1.8g、3,3−ビス(4−ジメチルアミノフェニ
ル)−6−ジメチルアミノフタリドを0.2g使用した
以外は実施例1と同様の操作を行い、白色の上用紙を作
成した。[Embodiment 4]
Instead of 1.9 g of (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.1 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide, 2 g 1.8 g of-(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.2 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide were used. Except for the above, the same operation as in Example 1 was performed to produce a white upper sheet.
【0048】[比較例1]実施例1における、2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオラン1.9gと3,3−ビス(4−ジ
メチルアミノフェニル)−6−ジメチルアミノフタリド
0.1gの代わりに、2−(2,6−ジメチルアニリ
ノ)−3−メチル−6−ジエチルアミノフルオランのみ
を2.0g使用した以外は実施例1と同様の操作を行
い、白色の上用紙を作成した。[Comparative Example 1]
Instead of 1.9 g of (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.1 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide, 2 g The same operation as in Example 1 was carried out, except that only 2.0 g of-(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran was used, to produce a white upper paper.
【0049】[比較例2]実施例1における、2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオラン1.9gと3,3−ビス(4−ジ
メチルアミノフェニル)−6−ジメチルアミノフタリド
0.1gの代わりに、2−(2,4−ジメチルアニリ
ノ)−3−メチル−6−ジエチルアミノフルオランを
2.0g使用した以外は実施例1と同様の操作を行い、
白色の上用紙を作成した。[Comparative Example 2]
Instead of 1.9 g of (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 0.1 g of 3,3-bis (4-dimethylaminophenyl) -6-dimethylaminophthalide, 2 g The same operation as in Example 1 was performed, except that 2.0 g of-(2,4-dimethylanilino) -3-methyl-6-diethylaminofluoran was used,
White paper was created.
【0050】(評価方法: 発色画像濃度測定、耐光保
存性試験及び耐NOx性試験) 1.発色画像濃度測定 実施例1〜3、比較例1、2に於いて作成した上用紙を
クレーを塗布した下用紙と塗布面が接触するように重ね
て、ローラーで加圧して発色させた。この発色画像の濃
度をマクベス濃度計RD−914を用いて、色相を東京
電色(株)色差計TC−PIIIを用いてそれぞれ測定し
た。(Evaluation method: Color image density measurement, light storage stability test and NOx resistance test) Measurement of Colored Image Density The upper papers prepared in Examples 1 to 3 and Comparative Examples 1 and 2 were overlapped so that the lower paper coated with clay was in contact with the coated surface, and color was formed by pressing with a roller. The density of the color image was measured using a Macbeth densitometer RD-914, and the hue was measured using a color difference meter TC-PIII of Tokyo Denshoku Co., Ltd.
【0051】結果を表1に示す。Table 1 shows the results.
【0052】 [表1] ━━━━━━━━━━━━━━━━━━━━━━━━━━ マクベス濃度(O.D値) 色相(a値) ────────── B/W C ────────────────────────── 実施例1 0.85 0.62 8.96 実施例2 0.85 0.64 8.56 実施例3 0.85 0.63 8.70 ────────────────────────── 比較例1 0.84 0.57 9.74 比較例2 0.85 0.64 7.01 ━━━━━━━━━━━━━━━━━━━━━━━━━━ 表1において、マクベス濃度の項のB/Wはビジュアル
フィルターを使用した測定値、CはSPI赤フィルター
を使用した測定値を示す。[Table 1] {Macbeth density (OD value) Hue (a value)} {B / WC} Example 1 0.85 0.62 8.96 Example 20 .85 0.64 8.56 Example 3 0.85 0.63 8.70 比較 Comparative Example 10 .84 0.57 9.74 Comparative Example 2 0.85 0.64 7.01 に お い て In Table 1, In the Macbeth density term, B / W indicates a measured value using a visual filter, and C indicates a measured value using an SPI red filter.
【0053】マクベス濃度が高いほど発色濃度が高いこ
とを示す。また、色相のa値が高いほど色調が赤味であ
ることを示す。The higher the Macbeth density, the higher the color density. Also, the higher the a value of the hue, the redr the color tone.
【0054】マクベス濃度において、B/Wの測定値で
差がなくてもCの測定値が高い場合、目視の濃度が高く
見える。In the Macbeth density, if the measured value of C is high even if there is no difference between the measured values of B / W, the visual density looks high.
【0055】2.耐光保存性試験 上記操作により得られた発色画像について、耐光保存性
試験(蛍光灯20,000Luxを24時間照射)を行
い、試験後の画像濃度及び色相を同様に測定し、画像堅
牢度及び色相の赤変度を求めた。2. Light resistance preservation test A color storage image obtained by the above operation was subjected to a light preservation test (irradiation with a fluorescent lamp of 20,000 Lux for 24 hours), and the image density and hue after the test were measured in the same manner. Was determined.
【0056】結果を表2に示す。Table 2 shows the results.
【0057】 [表2] ━━━━━━━━━━━━━━━━━━━━━━━━━━ 画像堅牢度(%) 赤変度(Δa) ───────── B/W C ────────────────────────── 実施例1 80 77 0.60 実施例2 80 78 0.59 実施例3 79 77 0.98 比較例1 77 77 0.59 比較例2 76 68 8.02 ━━━━━━━━━━━━━━━━━━━━━━━━━━ 画像堅牢度(%)=[(試験後画像濃度)/(試験前画像濃
度)]×100 赤変度(Δa) = (試験後のa値)−(試験前のa
値) 表2において、画像堅牢度は数値が高いほど発色画像の
保存性が高いことを示す。また、赤変度は数値が高いほ
ど発色画像の赤変が強いことを示す。[Table 2] Image fastness (%) Redness (Δa) {B / WC} Example 1 80 77 0.60 Example 2 80 78 0.59 Example 3 79 77 0.98 Comparative Example 1 77 77 0.59 Comparative Example 2 76 68 8.02 Image fastness (%) = [(image density after test) / (image density before test)] × 100 Redness (Δa) = (a value after test) − (a before test)
Value) In Table 2, the higher the value of the image fastness, the higher the storability of the color image. The higher the numerical value of the redness, the stronger the redness of the color image.
【0058】表1、2に示す様に、本発明の感圧記録材
料の記録画像は発色色調の赤味が低く、発色濃度が高
く、且つ光による濃度低下及び赤変が少ない。As shown in Tables 1 and 2, the recorded image of the pressure-sensitive recording material of the present invention has a low reddish color tone, a high color density, and a small decrease in density and redness due to light.
【0059】3.耐NOx性試験 実施例4、比較例1において作成した上用紙を、サリチ
ル酸誘導体亜鉛塩を塗布した下用紙と塗布面が接触する
ように重ね、ローラーにより加圧して発色させた。この
発色画像試験片について、下記のごとく耐NOx性試験
を行い、色相の赤変度を求めた。3. NOx Resistance Test The upper paper prepared in Example 4 and Comparative Example 1 was overlapped with the lower paper coated with the zinc salt of the salicylic acid derivative so that the coated surface was in contact with the lower paper, and was pressed by a roller to develop color. This color image test piece was subjected to a NOx resistance test as described below to determine the degree of redness of the hue.
【0060】密閉容器中に試験片を吊り下げ、磁器製蒸
発皿に1%NaNO225mLおよび水375mLを入
れ、試験片を吊り下げた金具の上に置いてNOxガスを
発生させ、撹拌下、その雰囲気中に30分間放置した。The test piece was suspended in a closed container, 25 mL of 1% NaNO 2 and 375 mL of water were placed in a porcelain evaporating dish, and the test piece was placed on a suspended bracket to generate NOx gas. It was left in the atmosphere for 30 minutes.
【0061】この試験片について前記と同様に画像色相
を測定し、色相の赤変度を求めた。以上の結果を表3に
示す。 The image hue of this test piece was measured in the same manner as described above, and the red hue of the hue was determined. Table 3 shows the above results.
【0062】表3に示すように、本発明の感圧記録材料
の記録画像はNOxによる赤変が少ない。As shown in Table 3, the recorded image of the pressure-sensitive recording material of the present invention has little redness due to NOx.
【0063】[0063]
【発明の効果】本発明の感圧記録材料は、記録画像濃度
が高く、色調が純黒色で且つ光やNOxによる赤変が小
さく、濃度の低下も少ない。The pressure-sensitive recording material of the present invention has a high recorded image density, a pure black color, a small reddening due to light or NOx, and a small decrease in density.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平5−17698(JP,A) 特開 平1−150574(JP,A) 特開 平1−198385(JP,A) (58)調査した分野(Int.Cl.7,DB名) B41M 5/145 ────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-5-17698 (JP, A) JP-A-1-150574 (JP, A) JP-A-1-198385 (JP, A) Field (Int.Cl. 7 , DB name) B41M 5/145
Claims (3)
剤との発色反応を利用する感圧記録材料に於いて、全電
子供与性ロイコ色素のうち98〜80重量%が2−
(2,6−ジメチルアニリノ)−3−メチル−6−ジエ
チルアミノフルオランであり、2〜10重量%が3,3
−ビス(4−ジメチルアミノフェニル)−6−ジメチル
アミノフタリドである感圧記録材料。1. An electron-donating leuco dye and an electron-accepting color developing agent.
In a pressure-sensitive recording material utilizing a coloring reaction with an agent, 98 to 80% by weight of all electron donating leuco dyes is 2-
(2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran, 2 to 10% by weight of 3.3
- bis (4-dimethylaminophenyl) -6-dimethylamino phthalide pressure-sensitive recording material which is de.
5重量%が2−(2,6−ジメチルアニリノ)−3−メ
チル−6−ジエチルアミノフルオランであり、3〜8重
量%が3,3−ビス(4−ジメチルアミノフェニル)−
6−ジメチルアミノフタリドである請求項1の感圧記録
材料。2. 97-8 of all electron donating leuco dyes.
5% by weight is 2- (2,6-dimethylanilino) -3-methyl-6-diethylaminofluoran and 3 to 8% by weight is 3,3-bis (4-dimethylaminophenyl)-.
2. The pressure-sensitive recording material according to claim 1, which is 6-dimethylaminophthalide.
ルに封入されていることを特徴とする前記請求項1又は
2の感圧記録材料。Wherein the claim 1 or an electron donating leuco dye is characterized in that it is microencapsulated
2. Pressure-sensitive recording material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6212132A JP3019728B2 (en) | 1994-03-14 | 1994-08-11 | Pressure-sensitive recording material |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6-70024 | 1994-03-14 | ||
| JP7002494 | 1994-03-14 | ||
| JP6212132A JP3019728B2 (en) | 1994-03-14 | 1994-08-11 | Pressure-sensitive recording material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07304253A JPH07304253A (en) | 1995-11-21 |
| JP3019728B2 true JP3019728B2 (en) | 2000-03-13 |
Family
ID=26411193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6212132A Expired - Lifetime JP3019728B2 (en) | 1994-03-14 | 1994-08-11 | Pressure-sensitive recording material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3019728B2 (en) |
-
1994
- 1994-08-11 JP JP6212132A patent/JP3019728B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07304253A (en) | 1995-11-21 |
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