JPH0580357B2 - - Google Patents
Info
- Publication number
- JPH0580357B2 JPH0580357B2 JP61273009A JP27300986A JPH0580357B2 JP H0580357 B2 JPH0580357 B2 JP H0580357B2 JP 61273009 A JP61273009 A JP 61273009A JP 27300986 A JP27300986 A JP 27300986A JP H0580357 B2 JPH0580357 B2 JP H0580357B2
- Authority
- JP
- Japan
- Prior art keywords
- imino
- iminoisoindoline
- diisocyanate
- bis
- heat
- 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 - Fee Related
Links
- 239000000463 material Substances 0.000 claims description 31
- -1 aromatic isocyanate compound Chemical class 0.000 claims description 26
- 239000002243 precursor Substances 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- MTMKZABGIQJAEX-UHFFFAOYSA-N 4,4'-sulfonylbis[2-(prop-2-en-1-yl)phenol] Chemical compound C1=C(CC=C)C(O)=CC=C1S(=O)(=O)C1=CC=C(O)C(CC=C)=C1 MTMKZABGIQJAEX-UHFFFAOYSA-N 0.000 description 3
- ZUXXEBDVLVNWTK-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-iminoisoindol-1-amine Chemical compound ClC1=C(Cl)C(Cl)=C2C(=N)NC(=N)C2=C1Cl ZUXXEBDVLVNWTK-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 239000001019 fluorene dye Substances 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 238000001454 recorded image Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000003232 water-soluble binding agent Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- INYIRIRLWHMJMO-UHFFFAOYSA-N 1-amino-3-iminoisoindole-5-carbonitrile Chemical compound N#CC1=CC=C2C(=N)NC(=N)C2=C1 INYIRIRLWHMJMO-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- WCOXQTXVACYMLM-UHFFFAOYSA-N 2,3-bis(12-hydroxyoctadecanoyloxy)propyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC(O)CCCCCC)COC(=O)CCCCCCCCCCC(O)CCCCCC WCOXQTXVACYMLM-UHFFFAOYSA-N 0.000 description 1
- ZBCASHLVDDIURH-UHFFFAOYSA-N 2,5-dichloro-4-(2,5-dichloro-4-hydroxyphenyl)sulfanylphenol Chemical compound C1=C(Cl)C(O)=CC(Cl)=C1SC1=CC(Cl)=C(O)C=C1Cl ZBCASHLVDDIURH-UHFFFAOYSA-N 0.000 description 1
- VLKUYGATYGQVGR-UHFFFAOYSA-N 2,5-dichloro-4-(2,5-dichloro-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(Cl)C(O)=CC(Cl)=C1S(=O)(=O)C1=CC(Cl)=C(O)C=C1Cl VLKUYGATYGQVGR-UHFFFAOYSA-N 0.000 description 1
- GLVWLDFJJCHIAP-UHFFFAOYSA-N 2-(3-aminoisoindol-1-ylidene)-2-(4-nitrophenyl)acetonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(C#N)=C1C2=CC=CC=C2C(=N)N1 GLVWLDFJJCHIAP-UHFFFAOYSA-N 0.000 description 1
- BUPZWTXQBDNMSE-UHFFFAOYSA-N 2-(3-aminoisoindol-1-ylidene)-3-oxo-3-phenylpropanenitrile Chemical compound C12=CC=CC=C2C(N)=NC1=C(C#N)C(=O)C1=CC=CC=C1 BUPZWTXQBDNMSE-UHFFFAOYSA-N 0.000 description 1
- BDXWTIVCFJPDDL-UHFFFAOYSA-N 2-(3-aminoisoindol-1-ylidene)propanedinitrile Chemical compound C1=CC=C2C(N)=NC(=C(C#N)C#N)C2=C1 BDXWTIVCFJPDDL-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- QFVUEDCMQHVPCR-UHFFFAOYSA-N 2-[(3-aminoisoindol-1-ylidene)amino]-5-nitrobenzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC=C([N+]([O-])=O)C=C1C#N QFVUEDCMQHVPCR-UHFFFAOYSA-N 0.000 description 1
- FAWCMAOGWZQKKS-UHFFFAOYSA-N 2-butyl-4-(3-butyl-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(O)C(CCCC)=CC(S(=O)(=O)C=2C=C(CCCC)C(O)=CC=2)=C1 FAWCMAOGWZQKKS-UHFFFAOYSA-N 0.000 description 1
- PWDGALQKQJSBKU-UHFFFAOYSA-N 2-chloro-4-(3-chloro-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(Cl)C(O)=CC=C1S(=O)(=O)C1=CC=C(O)C(Cl)=C1 PWDGALQKQJSBKU-UHFFFAOYSA-N 0.000 description 1
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 1
- DDUAGHRQCQFMGR-UHFFFAOYSA-N 2-cyclohexyl-4-(3-cyclohexyl-4-hydroxyphenyl)sulfanylphenol Chemical compound C1=C(C2CCCCC2)C(O)=CC=C1SC(C=1)=CC=C(O)C=1C1CCCCC1 DDUAGHRQCQFMGR-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-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
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- ATMYSTFCQICLBS-UHFFFAOYSA-N 3,3-dimethoxyisoindol-1-amine Chemical compound C1=CC=C2C(OC)(OC)NC(=N)C2=C1 ATMYSTFCQICLBS-UHFFFAOYSA-N 0.000 description 1
- KICXABNWGGOUJL-UHFFFAOYSA-N 3-(2,4,5-trichlorophenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC(Cl)=C(Cl)C=C1Cl KICXABNWGGOUJL-UHFFFAOYSA-N 0.000 description 1
- PHUXAQGUTOIXTH-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC(Cl)=CC=C1Cl PHUXAQGUTOIXTH-UHFFFAOYSA-N 0.000 description 1
- YGPQSWWSELIAMJ-UHFFFAOYSA-N 3-(2,5-diethoxyphenyl)iminoisoindol-1-amine Chemical compound CCOC1=CC=C(OCC)C(N=C2C3=CC=CC=C3C(N)=N2)=C1 YGPQSWWSELIAMJ-UHFFFAOYSA-N 0.000 description 1
- LZFSHDBHENOUEE-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)iminoisoindol-1-amine Chemical compound COC1=CC=C(OC)C(N=C2C3=CC=CC=C3C(N)=N2)=C1 LZFSHDBHENOUEE-UHFFFAOYSA-N 0.000 description 1
- LRZFIQUITFFBSO-UHFFFAOYSA-N 3-(2,6-dichloro-4-nitrophenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl LRZFIQUITFFBSO-UHFFFAOYSA-N 0.000 description 1
- LENOKGWQFDDHLU-UHFFFAOYSA-N 3-(2-methyl-4-nitrophenyl)iminoisoindol-1-amine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1C2=CC=CC=C2C(N)=N1 LENOKGWQFDDHLU-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- PNJXYMQKYORAQQ-UHFFFAOYSA-N 3-(3-chlorophenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC=CC(Cl)=C1 PNJXYMQKYORAQQ-UHFFFAOYSA-N 0.000 description 1
- KVXDFNAYWAFSJB-UHFFFAOYSA-N 3-(4-anilinophenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC(C=C1)=CC=C1NC1=CC=CC=C1 KVXDFNAYWAFSJB-UHFFFAOYSA-N 0.000 description 1
- RBISPTWFDRRBNV-UHFFFAOYSA-N 3-(4-phenyldiazenylphenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 RBISPTWFDRRBNV-UHFFFAOYSA-N 0.000 description 1
- MZIDKZUJISFGEP-UHFFFAOYSA-N 3-(5-chloro-2-phenoxyphenyl)iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 MZIDKZUJISFGEP-UHFFFAOYSA-N 0.000 description 1
- UIIYQMXYGDFHNF-UHFFFAOYSA-N 3-[(3-aminoisoindol-1-ylidene)amino]-4-chlorobenzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC(C#N)=CC=C1Cl UIIYQMXYGDFHNF-UHFFFAOYSA-N 0.000 description 1
- VGGHYUJPEOVCFR-UHFFFAOYSA-N 3-[2-chloro-5-(trifluoromethyl)phenyl]iminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC(C(F)(F)F)=CC=C1Cl VGGHYUJPEOVCFR-UHFFFAOYSA-N 0.000 description 1
- UKMBAYGWYFUXEF-UHFFFAOYSA-N 3-amino-4,5,6,7-tetrabromoisoindol-1-one Chemical compound BrC1=C(Br)C(Br)=C(Br)C2=C1C(N)=NC2=O UKMBAYGWYFUXEF-UHFFFAOYSA-N 0.000 description 1
- LOZJNNNVLREXGU-UHFFFAOYSA-N 3-amino-4,5,6,7-tetrachloroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(N)=NC2=O LOZJNNNVLREXGU-UHFFFAOYSA-N 0.000 description 1
- FOHPCQTYGFYWHT-UHFFFAOYSA-N 3-amino-4,5,6,7-tetrafluoroisoindol-1-one Chemical compound FC1=C(F)C(F)=C(F)C2=C1C(N)=NC2=O FOHPCQTYGFYWHT-UHFFFAOYSA-N 0.000 description 1
- DXOZLVKWNOFJEB-UHFFFAOYSA-N 3-amino-4,5,7-trichloro-6-methoxyisoindol-1-one Chemical compound ClC1=C(Cl)C(OC)=C(Cl)C2=C1C(=N)NC2=O DXOZLVKWNOFJEB-UHFFFAOYSA-N 0.000 description 1
- FBFYJKCQSJNNPL-UHFFFAOYSA-N 3-amino-4,5,7-trichloro-6-methylsulfanylisoindol-1-one Chemical compound ClC1=C(Cl)C(SC)=C(Cl)C2=C1C(N)=NC2=O FBFYJKCQSJNNPL-UHFFFAOYSA-N 0.000 description 1
- NOFJASWEFDKODU-UHFFFAOYSA-N 3-amino-5,6-dichloroisoindol-1-one Chemical compound ClC1=C(Cl)C=C2C(N)=NC(=O)C2=C1 NOFJASWEFDKODU-UHFFFAOYSA-N 0.000 description 1
- NWODCABIQVPNBA-UHFFFAOYSA-N 3-amino-6-nitroisoindol-1-one Chemical compound [O-][N+](=O)C1=CC=C2C(N)=NC(=O)C2=C1 NWODCABIQVPNBA-UHFFFAOYSA-N 0.000 description 1
- MMBYJYAFFGKUDC-UHFFFAOYSA-N 3-aminoisoindol-1-one Chemical compound C1=CC=C2C(N)=NC(=O)C2=C1 MMBYJYAFFGKUDC-UHFFFAOYSA-N 0.000 description 1
- MTRJTXJSAKQPBB-UHFFFAOYSA-N 3-ethoxy-3h-isoindol-1-amine Chemical compound C1=CC=C2C(OCC)N=C(N)C2=C1 MTRJTXJSAKQPBB-UHFFFAOYSA-N 0.000 description 1
- PUHLWDSZVTZIHR-UHFFFAOYSA-N 3-ethyl-4-(2-ethyl-4-hydroxyphenyl)sulfanylphenol Chemical compound CCC1=CC(O)=CC=C1SC1=CC=C(O)C=C1CC PUHLWDSZVTZIHR-UHFFFAOYSA-N 0.000 description 1
- FRNUGIYDRWMNBJ-UHFFFAOYSA-N 3-ethyl-4-(2-ethyl-4-hydroxyphenyl)sulfonylphenol Chemical compound CCC1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1CC FRNUGIYDRWMNBJ-UHFFFAOYSA-N 0.000 description 1
- ULNBACHCVNVEHG-UHFFFAOYSA-N 3-imino-5-methoxyisoindol-1-amine Chemical compound COC1=CC=C2C(N)=NC(=N)C2=C1 ULNBACHCVNVEHG-UHFFFAOYSA-N 0.000 description 1
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 1
- LTBKHBIPKHIHLF-UHFFFAOYSA-N 3-phenyliminoisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1=NC1=CC=CC=C1 LTBKHBIPKHIHLF-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- INCVSESIFQIURH-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3,3-diethoxyisoindol-1-amine Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(OCC)(OCC)N=C2N INCVSESIFQIURH-UHFFFAOYSA-N 0.000 description 1
- WMEUAJNEHZPXEQ-UHFFFAOYSA-N 4-(4-hydroxy-2,5-dimethylphenyl)sulfanyl-2,5-dimethylphenol Chemical compound C1=C(O)C(C)=CC(SC=2C(=CC(O)=C(C)C=2)C)=C1C WMEUAJNEHZPXEQ-UHFFFAOYSA-N 0.000 description 1
- QVKJTLXSMQPTEU-UHFFFAOYSA-N 4-(4-hydroxy-2,5-dimethylphenyl)sulfonyl-2,5-dimethylphenol Chemical compound C1=C(O)C(C)=CC(S(=O)(=O)C=2C(=CC(O)=C(C)C=2)C)=C1C QVKJTLXSMQPTEU-UHFFFAOYSA-N 0.000 description 1
- HUZYJNBLZPDJPY-UHFFFAOYSA-N 4-(4-hydroxy-2-methyl-5-propan-2-ylphenyl)sulfanyl-5-methyl-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(SC=2C(=CC(O)=C(C(C)C)C=2)C)=C1C HUZYJNBLZPDJPY-UHFFFAOYSA-N 0.000 description 1
- JPSMTGONABILTP-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)sulfanyl-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(SC=2C=C(C)C(O)=C(C)C=2)=C1 JPSMTGONABILTP-UHFFFAOYSA-N 0.000 description 1
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- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
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- DAUHNURARSXGAN-UHFFFAOYSA-N 5-imino-1-sulfocyclohex-2-ene-1-carboxylic acid Chemical compound OC(=O)C1(S(O)(=O)=O)CC(=N)CC=C1 DAUHNURARSXGAN-UHFFFAOYSA-N 0.000 description 1
- XAICWTLLSRXZPB-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzoic acid Chemical class CC(C)(C)C1=CC=C(O)C(C(O)=O)=C1 XAICWTLLSRXZPB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
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- CMHMMKSPYOOVGI-UHFFFAOYSA-N Isopropylparaben Chemical compound CC(C)OC(=O)C1=CC=C(O)C=C1 CMHMMKSPYOOVGI-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- 229950011260 betanaphthol Drugs 0.000 description 1
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- 125000006267 biphenyl group Chemical group 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- 239000002131 composite material Substances 0.000 description 1
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- NWYSGVZOXZTSDQ-UHFFFAOYSA-N cyanomethyl 2-(3-aminoisoindol-1-ylidene)acetate Chemical compound C1=CC=C2C(=N)NC(=CC(=O)OCC#N)C2=C1 NWYSGVZOXZTSDQ-UHFFFAOYSA-N 0.000 description 1
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
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- 229930195729 fatty acid Natural products 0.000 description 1
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 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
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
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- 150000003077 polyols Chemical class 0.000 description 1
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- 238000010298 pulverizing process Methods 0.000 description 1
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- 230000002940 repellent Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N salicylic acid benzyl ester Natural products OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- GKNIKZFNURIXEK-UHFFFAOYSA-N spiro[1,3-dioxolane-2,3'-isoindole]-1'-amine Chemical compound C12=CC=CC=C2C(=N)NC21OCCO2 GKNIKZFNURIXEK-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 150000003568 thioethers Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ äžè¬åŒïŒïŒ ãåã ïŒåŒäžãR1ïŒR2ïŒR3ïŒR4ïŒR5ããã³R6ã¯ãã
ãããäœçŽã¢ã«ãã«åºãè¡šãããïŒ ã§ç€ºãããéåžžç¡è²ãŸãã¯æ·¡è²ã®ææåé§äœãšã
該ææåé§äœãšåå¿ããŠãããçºè²ãããé¡è²å€
ãšãããªãèšé²ææã«ãããŠãè³éŠææ§ã€ãœã·ã¢
ããŒãååç©ããã³å°ãªããšãïŒåã®ïŒ£ïŒNH
åºãæããã€ããååç©ãé åããŠãªãããšãç¹
城ãšããè¿èµ€å€å ã§èªåãå¯èœãªæç±èšé²ææã
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61273009A JPS63126785A (ja) | 1986-11-18 | 1986-11-18 | èšé²ææ |
US07/122,191 US4880767A (en) | 1986-11-18 | 1987-11-18 | Recording material |
US07/378,789 US4983569A (en) | 1986-11-18 | 1989-07-12 | Recording material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61273009A JPS63126785A (ja) | 1986-11-18 | 1986-11-18 | èšé²ææ |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63126785A JPS63126785A (ja) | 1988-05-30 |
JPH0580357B2 true JPH0580357B2 (ja) | 1993-11-08 |
Family
ID=17521881
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61273009A Granted JPS63126785A (ja) | 1986-11-18 | 1986-11-18 | èšé²ææ |
Country Status (2)
Country | Link |
---|---|
US (2) | US4880767A (ja) |
JP (1) | JPS63126785A (ja) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63126785A (ja) * | 1986-11-18 | 1988-05-30 | Mitsubishi Paper Mills Ltd | èšé²ææ |
JPH0775911B2 (ja) * | 1988-10-12 | 1995-08-16 | äžè±è£œçŽæ ªåŒäŒç€Ÿ | æç±èšé²ææ |
JPH089268B2 (ja) * | 1988-10-17 | 1996-01-31 | äžè±è£œçŽæ ªåŒäŒç€Ÿ | æç±èšé²ææã®è£œé æ¹æ³ |
JPH0784103B2 (ja) * | 1988-10-18 | 1995-09-13 | äžè±è£œçŽæ ªåŒäŒç€Ÿ | æç±èšé²ææ |
JP2617213B2 (ja) * | 1988-11-10 | 1997-06-04 | äžè±è£œçŽæ ªåŒäŒç€Ÿ | æç±èšé²çšã€ã³ã¯ |
US5208208A (en) * | 1990-07-25 | 1993-05-04 | Mitsubishi Paper Mills Limited | Heat-sensitive recording material |
JP2871865B2 (ja) * | 1990-12-28 | 1999-03-17 | äžè±è£œçŽæ ªåŒäŒç€Ÿ | æç±èšé²ææ |
US5726120A (en) * | 1995-06-07 | 1998-03-10 | Moore Business Forms, Inc. | CF sheet for carbonless copy paper and weather resistant tags incorporating same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59135186A (ja) * | 1983-01-24 | 1984-08-03 | Asahi Chem Ind Co Ltd | èšé²ã·âã |
JPS60226871A (ja) * | 1984-04-25 | 1985-11-12 | Yamamoto Kagaku Gosei Kk | ãã«ãªã¬ã³ååç©ããã®è£œé æ³ããã³è©²ååç©ãçšããèšé²ææ |
JPS61110586A (ja) * | 1984-11-06 | 1986-05-28 | Mitsubishi Paper Mills Ltd | æç±èšé²çšææ |
JPS61172791A (ja) * | 1985-01-28 | 1986-08-04 | Mitsubishi Paper Mills Ltd | æç±èšé²ææ |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4521793A (en) * | 1982-02-27 | 1985-06-04 | Asahi Kasei Kogyo Kabushiki Kaisha | Coloring method and color-forming material |
JPS61175077A (ja) * | 1985-01-31 | 1986-08-06 | Mitsubishi Paper Mills Ltd | æç±èšé²çšã©ãã« |
JPS63126785A (ja) * | 1986-11-18 | 1988-05-30 | Mitsubishi Paper Mills Ltd | èšé²ææ |
-
1986
- 1986-11-18 JP JP61273009A patent/JPS63126785A/ja active Granted
-
1987
- 1987-11-18 US US07/122,191 patent/US4880767A/en not_active Expired - Lifetime
-
1989
- 1989-07-12 US US07/378,789 patent/US4983569A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59135186A (ja) * | 1983-01-24 | 1984-08-03 | Asahi Chem Ind Co Ltd | èšé²ã·âã |
JPS60226871A (ja) * | 1984-04-25 | 1985-11-12 | Yamamoto Kagaku Gosei Kk | ãã«ãªã¬ã³ååç©ããã®è£œé æ³ããã³è©²ååç©ãçšããèšé²ææ |
JPS61110586A (ja) * | 1984-11-06 | 1986-05-28 | Mitsubishi Paper Mills Ltd | æç±èšé²çšææ |
JPS61172791A (ja) * | 1985-01-28 | 1986-08-04 | Mitsubishi Paper Mills Ltd | æç±èšé²ææ |
Also Published As
Publication number | Publication date |
---|---|
US4880767A (en) | 1989-11-14 |
US4983569A (en) | 1991-01-08 |
JPS63126785A (ja) | 1988-05-30 |
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