JP6856409B2 - 感熱記録材料 - Google Patents
感熱記録材料 Download PDFInfo
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- JP6856409B2 JP6856409B2 JP2017043113A JP2017043113A JP6856409B2 JP 6856409 B2 JP6856409 B2 JP 6856409B2 JP 2017043113 A JP2017043113 A JP 2017043113A JP 2017043113 A JP2017043113 A JP 2017043113A JP 6856409 B2 JP6856409 B2 JP 6856409B2
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- JP
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- group
- residue
- heat
- sensitive recording
- tolylaminocarbonyl
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 65
- -1 N-substituted amino Chemical group 0.000 claims description 95
- 235000001014 amino acid Nutrition 0.000 claims description 47
- OQOLSESLQNHUPJ-NSHDSACASA-N (2s)-2-[(3-methylphenyl)carbamoylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)NC1=CC=CC(C)=C1 OQOLSESLQNHUPJ-NSHDSACASA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000000981 basic dye Substances 0.000 claims description 11
- 239000000975 dye Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 108090000765 processed proteins & peptides Chemical group 0.000 claims description 9
- HGWDEINNQMROCA-HNNXBMFYSA-N (2s)-2-[(3-methylphenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound CC1=CC=CC(NC(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 HGWDEINNQMROCA-HNNXBMFYSA-N 0.000 claims description 8
- 239000004474 valine Substances 0.000 claims description 8
- HQLHNJUMHYRCJL-JTQLQIEISA-N (2s)-4-methylsulfanyl-2-(phenylcarbamoylamino)butanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)NC1=CC=CC=C1 HQLHNJUMHYRCJL-JTQLQIEISA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- ODNNHJCIUBWQHO-NSHDSACASA-N (2s)-2-[(4-methylphenyl)carbamoylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)NC1=CC=C(C)C=C1 ODNNHJCIUBWQHO-NSHDSACASA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000539 amino acid group Chemical group 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 6
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 6
- LEVWYRKDKASIDU-IMJSIDKUSA-N cystine group Chemical group C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical group N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 6
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 claims description 6
- 239000004472 Lysine Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 5
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 5
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims description 2
- 229940024606 amino acid Drugs 0.000 description 49
- 238000012360 testing method Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
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- 150000001875 compounds Chemical class 0.000 description 21
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 14
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical class OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229960005190 phenylalanine Drugs 0.000 description 12
- 229920002451 polyvinyl alcohol Polymers 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
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- 150000001408 amides Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229960004295 valine Drugs 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229960004452 methionine Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- BZPWDHCTIAIAJK-NSHDSACASA-N (2s)-3-methyl-2-[(3-methylphenyl)carbamoylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)NC1=CC=CC(C)=C1 BZPWDHCTIAIAJK-NSHDSACASA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 6
- CLOYFSDWXPPMTI-HNNXBMFYSA-N (2S)-3-(4-hydroxyphenyl)-2-[(3-methylphenyl)carbamoylamino]propanoic acid Chemical compound C1(=CC(=CC=C1)NC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O)C CLOYFSDWXPPMTI-HNNXBMFYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 4
- 229940100389 Sulfonylurea Drugs 0.000 description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 231100000507 endocrine disrupting Toxicity 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- GQYXTPCXICJQIV-UHFFFAOYSA-N 2-[(3-methylphenyl)carbamoylamino]-2-phenylacetic acid Chemical compound CC1=CC=CC(NC(=O)NC(C(O)=O)C=2C=CC=CC=2)=C1 GQYXTPCXICJQIV-UHFFFAOYSA-N 0.000 description 3
- PPDKUGSOVUQARL-UHFFFAOYSA-N 3-[(4-methylphenyl)sulfonylamino]propanoic acid Chemical compound CC1=CC=C(S(=O)(=O)NCCC(O)=O)C=C1 PPDKUGSOVUQARL-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 108010008488 Glycylglycine Proteins 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical group NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 229940000635 beta-alanine Drugs 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- IPWQOZCSQLTKOI-QMMMGPOBSA-N d-[(amino)carbonyl]phenylalanine Chemical compound NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 IPWQOZCSQLTKOI-QMMMGPOBSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 3
- 229940043257 glycylglycine Drugs 0.000 description 3
- 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 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- 150000003457 sulfones Chemical class 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
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- LQXKHFZRJYXXFA-QMMMGPOBSA-N (2s)-2-[(4-methylphenyl)sulfonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NS(=O)(=O)C1=CC=C(C)C=C1 LQXKHFZRJYXXFA-QMMMGPOBSA-N 0.000 description 2
- AGPLQTQFIZBOLI-UHFFFAOYSA-N 1-benzyl-4-phenylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1CC1=CC=CC=C1 AGPLQTQFIZBOLI-UHFFFAOYSA-N 0.000 description 2
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 2
- OAGNKYSIOSDNIG-UHFFFAOYSA-N 1-methyl-3-[2-(3-methylphenoxy)ethoxy]benzene Chemical compound CC1=CC=CC(OCCOC=2C=C(C)C=CC=2)=C1 OAGNKYSIOSDNIG-UHFFFAOYSA-N 0.000 description 2
- FLQZMUXFJLKXGY-UHFFFAOYSA-N 2-(phenylcarbamoylamino)acetic acid Chemical compound OC(=O)CNC(=O)NC1=CC=CC=C1 FLQZMUXFJLKXGY-UHFFFAOYSA-N 0.000 description 2
- VDKFCCZUCXYILI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]acetic acid Chemical compound CC1=CC=C(S(=O)(=O)NCC(O)=O)C=C1 VDKFCCZUCXYILI-UHFFFAOYSA-N 0.000 description 2
- JCDIXEODZQBPRL-UHFFFAOYSA-N 2-[[2-(phenylcarbamothioylamino)acetyl]amino]acetic acid Chemical compound C1(=CC=CC=C1)NC(=S)NCC(=O)NCC(=O)O JCDIXEODZQBPRL-UHFFFAOYSA-N 0.000 description 2
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 2
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 2
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Chemical class OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical class OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical class C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
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- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical class OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
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- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Chemical class OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 2
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- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical class CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
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- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
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- 150000004651 carbonic acid esters Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 238000001914 filtration Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- XKUKSGPZAADMRA-UHFFFAOYSA-N glycyl-glycyl-glycine Chemical compound NCC(=O)NCC(=O)NCC(O)=O XKUKSGPZAADMRA-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- DPSUNBLQDAVPRY-INIZCTEOSA-N methyl (2S)-2-[(4-methylphenyl)sulfonylcarbamoylamino]-3-phenylpropanoate Chemical compound COC([C@@H](NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1)CC1=CC=CC=C1)=O DPSUNBLQDAVPRY-INIZCTEOSA-N 0.000 description 2
- CEMZBWPSKYISTN-YFKPBYRVSA-N methyl (2s)-2-amino-3-methylbutanoate Chemical class COC(=O)[C@@H](N)C(C)C CEMZBWPSKYISTN-YFKPBYRVSA-N 0.000 description 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical class COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
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- 239000004745 nonwoven fabric Substances 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000002972 p-tolylamino group Chemical group [H]N(*)C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BXPNTXBBAVYAMD-UHFFFAOYSA-N phenyl 2-aminoacetate Chemical compound NCC(=O)OC1=CC=CC=C1 BXPNTXBBAVYAMD-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical class OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MRDQQJOIAHNUTN-ZDUSSCGKSA-N propan-2-yl (2S)-3-methyl-2-(phenylcarbamothioylamino)butanoate Chemical compound C(C)(C)OC([C@@H](NC(=S)NC1=CC=CC=C1)C(C)C)=O MRDQQJOIAHNUTN-ZDUSSCGKSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- XUNZTECHYHOQHK-UHFFFAOYSA-N sulfuryl dichloride;1,3-xylene Chemical compound ClS(Cl)(=O)=O.CC1=CC=CC(C)=C1 XUNZTECHYHOQHK-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- XJJBXZIKXFOMLP-ZETCQYMHSA-N tert-butyl (2s)-pyrrolidine-2-carboxylate Chemical class CC(C)(C)OC(=O)[C@@H]1CCCN1 XJJBXZIKXFOMLP-ZETCQYMHSA-N 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- 150000003587 threonine derivatives Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Chemical class ON1CCCC1C(O)=O FGMPLJWBKKVCDB-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
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 239000013053 water resistant agent Substances 0.000 description 1
- 239000008096 xylene 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
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
Description
印字部の保存安定性とは、印字画像が高湿度の環境下に置かれた場合、水が付着した場合、油類が付着した場合又は可塑剤が付着した場合等にも消失しない性能を意味する。
(R−X)m−Y−(Z)m ・・・(1)
(式(1)中、RはC6〜C10のアリール基を有するアルキル基、又は、C1〜C8のアルキル基、C7〜C11のアラルキル基、C6〜C10のアリール基、若しくはC1〜C8のアルコキシ基の置換基を有していてもよいアリール基を表す。
Xは、YのN末端に結合する基であって、−OCO−、−SO2NHCO−、−NHCO−、−NHCS−、又は−SO2−を表わす。
Yは、アミノ酸残基又はペプチド残基を表わし、Y基中の、セリン残基、スレオニン残基、アスパラギン酸残基、グルタミン酸残基、又はチロシン残基のOH基は、OR基又はOR”基に置換していてもよく、システイン残基のSH基は、SR基又はSR”基に置換していてもよく、ヒスチジン残基のNH基は、NR基又はNR’基に置換していてもよく、リシン残基又はオルニチン残基のNH2基は、NHR基又はNHR’基に置換していてもよく、R’はアミノ保護基を表し、R”はカルボキシ保護基を表す。
Zは、YのC末端に結合する基であって、OH基又はOR”基を表す。
複数のR、R’、R”は同じであっても、異なっていてもよく、互いに結合して環を形成していてもよい。
ただし、Yは、シスチン残基以外のアミノ酸残基であるとき又はシスチン残基を有さないペプチド残基であり、m=1である。)
(R−X)m−Y−(Z)m ・・・(1)
複数のR、R’、R”は同じであっても、異なっていてもよく、互いに結合して環を形成していてもよい。
ただし、Yは、シスチン残基以外のアミノ酸残基であるとき又はシスチン残基を有さないペプチド残基であり、m=1である。
N−(m−トリルアミノカルボニル)−メチオニン、N−(m−トリルアミノカルボニル)−バリン、N−(m−トリルアミノカルボニル)−フェニルグリシン、N−(m−フェニルグリシン、N−(3−イソプロペニル−α、α−ジメチルベンジル)アミノカルボニル−メチオニン、およびN−(m−トリルアミノカルボニル)−チロシンからなる群から選ばれる少なくとも1種を使用することが良好である。
本発明の感熱記録材料における前記一般式(1)で表されるN−置換アミノ酸誘導体の、Y基中のアスパラギン酸残基又はグルタミン酸残基を保護するカルボキシ保護基(R”基)として、アルコキシ基、アリールオキシ基、アミノ基、アルキルアミノ基、アリールアミノ基などが挙げられる。また、Y基中のセリン残基、スレオニン残基、若しくはチロシン残基のOH基、又はシステイン残基のSH基の保護基として、前記カルボキシ保護基(R”基)が挙げられる。これらのカルボキシ保護基(R”基)は、公知の方法により導入することができる。
これらN−置換アミノ酸誘導体の1種あるいは2種以上を併用して用いても良い。
本発明の感熱記録材料において、常温で無色ないし淡色の塩基性染料としてトリフェニルメタン系、フルオラン系、ジフェニルメタン系、スピロ系、フルオレン系、チアジン系化合物が挙げられ、従来公知のロイコ染料から選ぶことができる。
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、3,3−ビス(p−ジメチルアミノフェニル)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、
3,3−ビス(P−メチルアミノフェニル)−6−ジメチルアミノフタリド、
3−ジエチルアミノ−7−ジベンジルアミノベンゾ[α]フルオラン、
3−(1−エチル−2−メチルインドール−3−イル)−3−(4−ジエチルアミノ−2−n−ヘキシルオキシフェニル−4−アザフタリド、3−(1−エチル−2−メチルインドール−3−イル)−3−(4−ジエチルアミノ)−2−メチルフェニル−4−アザフタリド、3−(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−メチル−1−n−オクチルインドール−3−イル)−3−(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−(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−ジエチルアミノ−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−(o,p−ジメチルアニリノ)フルオラン、
などからも選ぶことができ、本発明はこれらに限定されるものではなく、又2種類以上を併用してもよい。
例えば、ステアリン酸アミド、ビスステアリン酸アミド、パルミチン酸アミドなどの脂肪酸アミド、p−トルエンスルホンアミド、ステアリン酸、ベヘン酸やパルミチン酸などのカルシウム、亜鉛あるいはアルミニウムなどの脂肪酸金属塩、p−ベンジルビフェニル、ジフェニルスルホン、ベンジルオキシ安息香酸ベンジル、2−ベンジルオキシナフタレン、1,2−ビス(p−トリルオキシ)エタン、1,2−ビス(フェノキシ)エタン、1,2−ビス(3−メチルフェノキシ)エタン、1,3−ビス(フェノキシ)プロパン、シュウ酸ジベンジル、シュウ酸p−メチルベンジル、m−ターフェニル、1−ヒドロキシ−2−ナフトエ酸などが挙げられる。
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)、1,1、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、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、4,4’−ビス[(4−メチル−3−フェノキシカルボニルアミノフェニル)ウレイド]ジフェニルスルホン、トリス(2,6−ジメチル−4−tert−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−メチルグリシルオキシ)ジフェニルスルホン、テレフタル酸グリシジル、ビスフェノールA型エポキシ樹脂型、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塩または多価金属塩、ビス(4−エチレンイミンカルボニルアミノフェニル)メタン、4,4’−ビス[(4−メチル−3−フェノキシカルボニルアミノフェニル)ウレイド]ジフェニルスルホンおよび、下記一般式(2)で表されるジフェニルスルホン架橋型化合物等が挙げられ、これらの保存安定剤は、感熱記録材料の印字部の保存安定性に寄与する。
このように微分散された分散液に、必要により顔料、バインダー、助剤等を混合撹拌することで感熱記録層塗料を調整される。
このようにして得られた感熱記録層塗料を、乾燥後の塗布量が1.5〜12g/m2程度、より好ましくは3〜7g/m2程度になるように、支持体上に塗布し、乾燥することで形成される。
合成例1: N−(m−トリルアミノカルボニル)−フェニルアラニン
温度計、滴下ロート、攪拌機を備えた4つ口フラスコに、L−フェニルアラニン16.5g及び水50gを仕込んだ後、内温を15℃に調整し、8%水酸化ナトリウム水溶液50gを加えL−フェニルアラニンを溶解した。内温を15℃に保持し、酢酸エチルに溶解したm−トリルイソシアネート13.3gを滴下し5時間撹拌した。反応液に酢酸エチルを加え、希塩酸で中和して生成物を酢酸エチルで抽出した。抽出液の酢酸エチルを濃縮後、濃縮残渣にトルエンを加えて結晶化した。結晶を濾別し乾燥して、白色結晶のN−(m−トリルアミノカルボニル)−フェニルアラニンを得た。融点は151℃であった。
合成例1のL−フェニルアラニン16.5gに代えて、L−メチオニン14.9gを用いる以外、合成例1と同様の操作により、白色結晶のN−(m−トリルアミノカルボニル)−メチオニンを得た。融点は142℃であった。
合成例1のL−フェニルアラニン16.5gに代えてL−バリン11.7gを用いる以外、合成例1と同様の操作により、白色結晶のN−(m−トリルアミノカルボニル)−バリンを得た。融点は169℃であった。
合成例1のL-フェニルアラニン16.5gに代えてL−システイン−S−ベンジル21.1gを用いる以外、合成例1と同様の操作により、白色結晶のN−(m−トリルアミノカルボニル)−システイン−S−ベンジルを得た。融点は164℃であった。
合成例1のL−フェニルアラニン16.5gに代えてL−チロシン18.1gを用いる以外、合成例1と同様の操作により、白色結晶のN−(m−トリルアミノスルホニル)−チロシンを得た。融点は161℃であった。
合成例1と同じ装置にグリシルグリシン13.2g、水50g、THF50gを仕込み8%水酸化ナトリウム水溶液50gを加えてグリシルグリシンを溶解した。内温を20〜25℃に維持しながらフェニルイソチオシアナート13.5gを滴下し5時間撹拌した。合成例1と同様の反応処理を行い白色結晶のN−フェニルアミノチオカルボニル−グリシルグリシンを得た。融点は157℃であった。
温度計、滴下ロート、攪拌機を備えた4つ口フラスコに、L−フェニルアラニン−メチルエステル塩酸塩21.5g及び酢酸エチル120gを仕込み、内温を10℃に保ちながら、トリエチルアミン10.1gを滴下した。内温を8〜10℃に保持しながらp−トルエンスルホニルイソシアナート19.7gを滴下し撹拌を5時間継続した。反応終了後、反応液に少量の酢酸を加え、水を加えて有機層を水洗分離した。有機層を減圧濃縮した残渣にトルエンを加え結晶を析出させ、濾過により白色結晶のN−(p−トルエンスルホニルアミノカルボニル)−フェニルアラニン−メチルエステルを得た。融点は162℃であった。
温度計、滴下ロート、攪拌機を備えた4つ口フラスコに、β−アラニン8.9g、水30g、8%水酸化ナトリウム水溶液を仕込み内温10℃まで冷却した。塩化p−トルエンスルホニル19.1gを溶解したTHF溶液30gと8%水酸化ナトリウム50gとを各々4分割し、各分画を交互にフラスコに滴下し反応をおこなった。4時間撹拌した後、希塩酸で酸性化した。反応液は合成例1と同様にして反応処理し白色結晶のN−(p−トルエンスルホニル)−β−アラニンを得た。融点は125℃であった。
プラスチック中空粒子(商品名:ローペイクSN−1055:中空率:55% 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。
[感熱記録用塗料の作成]
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
N−(m−トリルアミノカルボニル)−メチオニン(顕色剤1) 20部
10%ポリビニルアルコール水溶液 20部
水 33.3部
N−p−トルエンスルホニルN’−3―(p−トルエンスルホニルオキシ)フェニルウレア 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
B1液(顕色剤分散液) 55.0部
B2液(分散液) 18.3部
C液(増感剤分散液) 55.0部
支持体として坪量が53gの上質紙(酸性紙)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、感熱塗料が乾燥後の面積当たりの質量が3.5g/m2になるように塗布乾燥した。
このシートをス−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た。
1.感熱記録性試験(発色試験)
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、印加エネルギー0.38mJ/dotで印加した。記録部の印字濃度はマクベス反射濃度計RD−914で測定した。
感熱記録性試験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、試験片の印字部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、試験片の印字部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。
感熱記録性試験で記録した感熱記録材料にサラダオイル中に1分間浸漬しその後、試験片の油をふき取り、画像濃度をマクベス反射濃度計で測定した。
感熱記録性試験で記録した感熱記録紙を水中に24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。
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KMA三井化学製)を3重に巻き付け、感熱記録性試験で記録した感熱記録紙を乗せ、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B1液のN−(m−トリルアミノカルボニル)−メチオニン(顕色剤1)をN−(m−トリルアミノカルボニル)−フェニルアラニン(顕色剤2)に代える以外は実施例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B1液のN−(m−トリルアミノカルボニル)−メチオニン(顕色剤1)をN−(フェニルアミノカルボニル)−メチオニン(顕色剤3)に代える以外は実施例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N−(m−トリルアミノカルボニル)−メチオニン(顕色剤1)をN−(p−トリルアミノカルボニル)−メチオニン(顕色剤4)に代える以外は実施例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のN−(m−トリルアミノカルボニル)−メチオニン(顕色剤1)をN−(m−トリルアミノカルボニル)−バリン(顕色剤5)に代える以外は実施例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N−(m−トリルアミノカルボニル)−メチオニン(顕色剤1)をN−(m−トリルアミノカルボニル)−フェニルグリシン(顕色剤6)に代える以外は実施例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N−(m−トリルアミノカルボニル)−メチオニン(顕色剤1)をN−(m−トリルアミノカルボニル)−チロシン(顕色剤7)に代える以外は実施例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1〜7において各B1液を77.3部使用し、B2液を使用しない以外は実施例1〜7と同様の操作をおこなった。この参考例による感熱記録体の各種試験結果は、表1に記載の通りであった。
実施例1のB1液の顕色剤N−(m−トリルアミノカルボニル)−メチオニンをビスフェノールA(顕色剤8)に代える以外は参考例1〜7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B1液の顕色剤N−(m−トリルアミノカルボニル)−メチオニンを4,4’ビスフェノールS(顕色剤9)に代える以外は参考例1〜7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。
さらにN−p−トルエンスルホニルN’−3―(p−トルエンスルホニルオキシ)フェニルウレアを含む感熱記録材料は、N−p−トルエンスルホニルN’−3―(p−トルエンスルホニルオキシ)フェニルウレアを含まない感熱記録材料と比較して、耐水性に優れていた。
Claims (3)
- 常温で無色ないし淡色の塩基性染料と、加熱により該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、前記顕色剤として下記一般式(1)で表されるN−置換アミノ酸誘導体の少なくとも一種を含み、且つ、N−p−トルエンスルホニルN’−3−(p−トルエンスルホニルオキシ)フェニルウレアを含む感熱記録材料。
(R−X)m−Y−(Z)m ・・・(1)
(式(1)中、RはC6〜C10のアリール基を有するアルキル基、又は、C1〜C8のアルキル基、C7〜C11のアラルキル基、C6〜C10のアリール基、若しくはC1〜C8のアルコキシ基の置換基を有していてもよいアリール基を表す。
Xは、YのN末端に結合する基であって、−OCO−、−SO2NHCO−、−NHCO−、−NHCS−、又は−SO2−を表わす。
Yは、アミノ酸残基又はペプチド残基を表わし、Y基中の、セリン残基、スレオニン残基、アスパラギン酸残基、グルタミン酸残基、又はチロシン残基のOH基は、OR基又はOR”基に置換していてもよく、システイン残基のSH基は、SR基又はSR”基に置換していてもよく、ヒスチジン残基のNH基は、NR基又はNR’基に置換していてもよく、リシン残基又はオルニチン残基のNH2基は、NHR基又はNHR’基に置換していてもよく、R’はアミノ保護基を表し、R”はカルボキシ保護基を表す。
Zは、YのC末端に結合する基であって、OH基又はOR”基を表す。
複数のR、R’、R”は同じであっても、異なっていてもよく、互いに結合して環を形成していてもよい。
ただし、Yは、シスチン残基以外のアミノ酸残基又はシスチン残基を有さないペプチド残基であり、m=1である。) - 前記顕色剤がN−(m−トリルアミノカルボニル)−フェニルアラニン、N−(m−トリルアミノカルボニル)−メチオニン、N−(p−トリルアミノカルボニル)−メチオニン、N−(フェニルアミノカルボニル)−メチオニン、N−(m−トリルアミノカルボニル)−バリン、N−(m−トリルアミノカルボニル)−フェニルグリシンおよびN−(m−トリルアミノカルボニル)−チロシンからなる群から選ばれる少なくとも1種である請求項1記載の感熱記録材料。
- 前記、N−p−トルエンスルホニルN’−3−(p−トルエンスルホニルオキシ)フェニルウレアの含有量が、顕色剤100質量部に対して10〜400質量部であることを特徴とする請求項1又は2記載の感熱記録材料。
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