CA1283660C - Colorants de sublimation pour l'hectographie par voie thermique - Google Patents

Colorants de sublimation pour l'hectographie par voie thermique

Info

Publication number: CA1283660C
Authority: CA; Canada
Prior art keywords: methyl; fluorine; represents hydrogen; optionally substituted; hydrogen
Prior art date: 1984-07-11
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

Application number

CA000486541A

Other languages

English (en)

Inventor

Toshio Niwa

Yukichi Murata

Shuichi Maeda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Kasei Corp

Priority date (The priority date 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 date listed.)

1984-07-11

Filing date

1985-07-09

Publication date

1991-04-30

1984-07-11 Priority claimed from JP59143928A external-priority patent/JPS6122993A/ja

1984-07-24 Priority claimed from JP15374284A external-priority patent/JPS6131292A/ja

1984-07-30 Priority claimed from JP16013584A external-priority patent/JPS6135994A/ja

1984-08-16 Priority claimed from JP59170740A external-priority patent/JPS6149893A/ja

1984-08-30 Priority claimed from JP59181230A external-priority patent/JPS6157651A/ja

1984-12-21 Priority claimed from JP59270495A external-priority patent/JPH0676558B2/ja

1985-07-09 Application filed by Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp

1985-11-13 Priority to CA000495272A priority Critical patent/CA1232452A/fr

1991-04-30 Application granted granted Critical

1991-04-30 Publication of CA1283660C publication Critical patent/CA1283660C/fr

2008-04-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000975 dye Substances 0.000 title claims description 108
238000000859 sublimation Methods 0.000 title claims description 10
230000008022 sublimation Effects 0.000 title claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 118
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 92
239000001257 hydrogen Substances 0.000 claims abstract description 92
150000002431 hydrogen Chemical class 0.000 claims abstract description 71
-1 formylamino Chemical group 0.000 claims abstract description 56
229910052731 fluorine Inorganic materials 0.000 claims abstract description 49
239000011737 fluorine Substances 0.000 claims abstract description 49
125000003545 alkoxy group Chemical group 0.000 claims abstract description 46
125000000217 alkyl group Chemical group 0.000 claims abstract description 45
229910052736 halogen Inorganic materials 0.000 claims abstract description 37
150000002367 halogens Chemical group 0.000 claims abstract description 37
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 33
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 13
229920002554 vinyl polymer Polymers 0.000 claims abstract description 12
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 9
239000000460 chlorine Substances 0.000 claims description 49
238000000034 method Methods 0.000 claims description 40
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 29
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 29
229910052794 bromium Inorganic materials 0.000 claims description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 12
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 11
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 11
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
239000011248 coating agent Substances 0.000 claims description 7
238000000576 coating method Methods 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
239000011630 iodine Chemical group 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
238000001035 drying Methods 0.000 claims description 4
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
QQHSPMFNGRXXBP-UHFFFAOYSA-N COCl(NC(CC)=O)(NC(C)=O)NC=O Chemical group COCl(NC(CC)=O)(NC(C)=O)NC=O QQHSPMFNGRXXBP-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
239000010419 fine particle Substances 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 8
229940060038 chlorine Drugs 0.000 claims 8
235000017168 chlorine Nutrition 0.000 claims 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 7
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 5
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims 2
125000006343 heptafluoro propyl group Chemical group 0.000 claims 2
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
UPSNOKIUEULXHF-UHFFFAOYSA-N n-chloropropanamide Chemical compound CCC(=O)NCl UPSNOKIUEULXHF-UHFFFAOYSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 9
125000004658 aryl carbonyl amino group Chemical group 0.000 abstract description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
239000000976 ink Substances 0.000 description 33
238000002360 preparation method Methods 0.000 description 26
229960001701 chloroform Drugs 0.000 description 24
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 24
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
229910001961 silver nitrate Inorganic materials 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000010521 absorption reaction Methods 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 7
239000002904 solvent Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
239000012264 purified product Substances 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
238000004440 column chromatography Methods 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000000547 substituted alkyl group Chemical group 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000000123 paper Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000005979 thermal decomposition reaction Methods 0.000 description 3
ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
230000008018 melting Effects 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 2
229920002492 poly(sulfone) Polymers 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920001721 polyimide Polymers 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
229910000806 Latten Inorganic materials 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
239000011086 glassine Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
238000002156 mixing Methods 0.000 description 1
HTVPAACTHAQQAS-UHFFFAOYSA-N n-(2-hydroxy-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1O HTVPAACTHAQQAS-UHFFFAOYSA-N 0.000 description 1
KVHRISPSSMDQOB-UHFFFAOYSA-N n-(2-hydroxyphenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1O KVHRISPSSMDQOB-UHFFFAOYSA-N 0.000 description 1
WDXQGUCCFNYBDQ-UHFFFAOYSA-N n-(4-acetamido-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C(O)=C1 WDXQGUCCFNYBDQ-UHFFFAOYSA-N 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920006393 polyether sulfone Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Thermal Transfer Or Thermal Recording In General (AREA)

CA000486541A 1984-07-11 1985-07-09 Colorants de sublimation pour l'hectographie par voie thermique Expired - Lifetime CA1283660C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000495272A CA1232452A (fr)	1985-04-12	1985-11-13	Melange colorant pour enregistrement pyrometrique du transfert dans la sublimation

Applications Claiming Priority (12)

Application Number	Priority Date	Filing Date	Title
JP59143928A JPS6122993A (ja)	1984-07-11	1984-07-11	感熱転写記録用色素及び感熱転写記録用シート
JP143928/1984		1984-07-11
JP153742/1984		1984-07-24
JP15374284A JPS6131292A (ja)	1984-07-24	1984-07-24	感熱転写記録用色素及び感熱転写記録用シート
JP160135/1984		1984-07-30
JP16013584A JPS6135994A (ja)	1984-07-30	1984-07-30	感熱転写記録用色素及び感熱転写シート
JP170740/1984		1984-08-16
JP59170740A JPS6149893A (ja)	1984-08-16	1984-08-16	感熱転写記録用色素及び感熱転写記録用シート
JP59181230A JPS6157651A (ja)	1984-08-30	1984-08-30	インドアニリン系化合物、感熱転写記録用色素及び感熱転写記録用シート
JP181230/1984		1984-08-30
JP59270495A JPH0676558B2 (ja)	1984-12-21	1984-12-21	インドアニリン系化合物及び感熱転写記録用色素
JP270495/1984		1984-12-21

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000495272A Division CA1232452A (fr)	1985-04-12	1985-11-13	Melange colorant pour enregistrement pyrometrique du transfert dans la sublimation

Publications (1)

Publication Number	Publication Date
CA1283660C true CA1283660C (fr)	1991-04-30

Family

ID=27552979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000486541A Expired - Lifetime CA1283660C (fr)	1984-07-11	1985-07-09	Colorants de sublimation pour l'hectographie par voie thermique

Country Status (1)

Country	Link
CA (1)	CA1283660C (fr)

1985
- 1985-07-09 CA CA000486541A patent/CA1283660C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2008-04-30	MKEX	Expiry

Publication	Publication Date	Title
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Frank	1991	Developmental aspects of experimental pulmonary oxygen toxicity
JP3930901B2 (ja)	2007-06-13	印刷法
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