CA1099100A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1099100A
Authority: CA; Canada
Prior art keywords: composition; color; phenol; compound; amine
Prior art date: 1977-03-04
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

Application number

CA298,181A

Other languages

English (en)

Inventor

William R. Lawton

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.)

Individual

Original Assignee

Individual

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.)

1977-03-04

Filing date

1978-03-03

Publication date

1981-04-14

1977-03-04 Priority claimed from US05/774,385 external-priority patent/US4180405A/en

1978-03-03 Application filed by Individual filed Critical Individual

1981-04-14 Application granted granted Critical

1981-04-14 Publication of CA1099100A publication Critical patent/CA1099100A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 47
239000002243 precursor Substances 0.000 title claims abstract description 16
150000001412 amines Chemical class 0.000 claims abstract description 37
150000002596 lactones Chemical class 0.000 claims abstract description 14
125000004122 cyclic group Chemical group 0.000 claims abstract description 13
239000000758 substrate Substances 0.000 claims abstract description 13
238000000576 coating method Methods 0.000 claims abstract description 11
239000011230 binding agent Substances 0.000 claims abstract description 10
239000011248 coating agent Substances 0.000 claims abstract description 9
150000002989 phenols Chemical class 0.000 claims abstract description 9
230000015572 biosynthetic process Effects 0.000 claims abstract description 5
239000012190 activator Substances 0.000 claims abstract description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 40
239000000975 dye Substances 0.000 claims description 32
-1 fatty acid salts Chemical class 0.000 claims description 31
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 20
150000001408 amides Chemical class 0.000 claims description 19
239000003593 chromogenic compound Substances 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 15
HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 claims description 12
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims description 12
LWFPYLZOVOCBPZ-UHFFFAOYSA-N hydrindantin Chemical compound O=C1C2=CC=CC=C2C(=O)C1(O)C1(O)C(=O)C2=CC=CC=C2C1=O LWFPYLZOVOCBPZ-UHFFFAOYSA-N 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
239000006185 dispersion Substances 0.000 claims description 6
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims description 4
239000008139 complexing agent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
235000013877 carbamide Nutrition 0.000 claims description 2
235000014113 dietary fatty acids Nutrition 0.000 claims description 2
238000001704 evaporation Methods 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
229930195729 fatty acid Natural products 0.000 claims description 2
150000003672 ureas Chemical class 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 2
150000003585 thioureas Chemical class 0.000 claims 1
239000000376 reactant Substances 0.000 abstract description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 62
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 53
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 36
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 26
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 24
239000000463 material Substances 0.000 description 19
FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 17
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 16
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 15
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 14
235000013824 polyphenols Nutrition 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 12
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 12
239000000123 paper Substances 0.000 description 11
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 10
238000010494 dissociation reaction Methods 0.000 description 10
230000005593 dissociations Effects 0.000 description 10
NMGPHUOPSWFUEB-UHFFFAOYSA-N 2-(butylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCNCCOC(=O)C(C)=C NMGPHUOPSWFUEB-UHFFFAOYSA-N 0.000 description 9
HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 9
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 9
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 8
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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 6
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 5
229940113083 morpholine Drugs 0.000 description 5
LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
238000003384 imaging method Methods 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 3
ASLNDVUAZOHADR-UHFFFAOYSA-N 2-butyl-3-methylphenol Chemical compound CCCCC1=C(C)C=CC=C1O ASLNDVUAZOHADR-UHFFFAOYSA-N 0.000 description 3
CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 3
XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-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
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
229940107698 malachite green Drugs 0.000 description 3
RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 3
ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
230000035945 sensitivity Effects 0.000 description 3
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 2
DLNKOYKMWOXYQA-UHFFFAOYSA-N 2-amino-1-phenylpropan-1-ol Chemical compound CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 2
UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 2
NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 2
IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 2
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
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 2
JHZOXYGFQMROFJ-UHFFFAOYSA-N 3,5-dibromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(Br)C=C1C=O JHZOXYGFQMROFJ-UHFFFAOYSA-N 0.000 description 2
IGVZGOJWAQBGEG-UHFFFAOYSA-N 4-bromophenol formamide Chemical compound C(=O)N.BrC1=CC=C(C=C1)O IGVZGOJWAQBGEG-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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 2
UGCUSGOYPRYNPS-UHFFFAOYSA-N N(CCO)(CCO)CCO.C1(CCCCC1)C1=CC=C(C=C1)O Chemical compound N(CCO)(CCO)CCO.C1(CCCCC1)C1=CC=C(C=C1)O UGCUSGOYPRYNPS-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000004372 Polyvinyl alcohol Substances 0.000 description 2
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000000498 ball milling Methods 0.000 description 2
229950011260 betanaphthol Drugs 0.000 description 2
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
229960002887 deanol Drugs 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
229940043276 diisopropanolamine Drugs 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
239000012972 dimethylethanolamine Substances 0.000 description 2
229940031098 ethanolamine Drugs 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
UKOVZLWSUZKTRL-UHFFFAOYSA-N naphthalid Chemical compound C1=CC(C(=O)OC2)=C3C2=CC=CC3=C1 UKOVZLWSUZKTRL-UHFFFAOYSA-N 0.000 description 2
235000019645 odor Nutrition 0.000 description 2
JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 2
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
229920002451 polyvinyl alcohol Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229940079877 pyrogallol Drugs 0.000 description 2
239000001044 red dye Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
230000004044 response Effects 0.000 description 2
238000010186 staining Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229960001124 trientine Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
QWLQTDXXEZQUBB-UHFFFAOYSA-N 1,2-di(propan-2-yl)hydrazine Chemical compound CC(C)NNC(C)C QWLQTDXXEZQUBB-UHFFFAOYSA-N 0.000 description 1
ZTUKGBOUHWYFGC-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindole Chemical compound C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 ZTUKGBOUHWYFGC-UHFFFAOYSA-N 0.000 description 1
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ONVRFYIOLWICAX-UHFFFAOYSA-N N(CCO)CCO.ClC1=C(C(C=O)=CC(=C1)Cl)O Chemical compound N(CCO)CCO.ClC1=C(C(C=O)=CC(=C1)Cl)O ONVRFYIOLWICAX-UHFFFAOYSA-N 0.000 description 1
FRUDFFFLGQXAEZ-UHFFFAOYSA-N N(CCO)CCO.ClC=1C(=C(C(=C(C1)O)Cl)Cl)Cl Chemical compound N(CCO)CCO.ClC=1C(=C(C(=C(C1)O)Cl)Cl)Cl FRUDFFFLGQXAEZ-UHFFFAOYSA-N 0.000 description 1
IXGVEYCENUOBEK-UHFFFAOYSA-N N(CCO)CCO.ClC=1C(=C(C(=CC1Cl)Cl)O)[N+](=O)[O-] Chemical compound N(CCO)CCO.ClC=1C(=C(C(=CC1Cl)Cl)O)[N+](=O)[O-] IXGVEYCENUOBEK-UHFFFAOYSA-N 0.000 description 1
FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
RNJVREGSAXEQKN-UHFFFAOYSA-N NCCNCCN.ClC1=C(C2=CC=CC=C2C(=C1)Cl)O Chemical compound NCCNCCN.ClC1=C(C2=CC=CC=C2C(=C1)Cl)O RNJVREGSAXEQKN-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
XHEWLQPCGSHZSC-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C(C=O)=C1)O.C=C1N(C2=CC=CC=C2C1(C)C)C Chemical compound [N+](=O)([O-])C1=CC=C(C(C=O)=C1)O.C=C1N(C2=CC=CC=C2C1(C)C)C XHEWLQPCGSHZSC-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
FSHXODRICVTBJO-UHFFFAOYSA-N benzene-1,2-diol;benzene-1,4-diol Chemical compound OC1=CC=C(O)C=C1.OC1=CC=CC=C1O FSHXODRICVTBJO-UHFFFAOYSA-N 0.000 description 1
LWLXPYLMRNIXQK-UHFFFAOYSA-N benzene-1,3-diol hydrazine Chemical compound NN.C1(O)=CC(O)=CC=C1 LWLXPYLMRNIXQK-UHFFFAOYSA-N 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
NCYJUZHZLNZTOO-UHFFFAOYSA-N butane;2-(2-hydroxyethylamino)ethanol Chemical compound CCCC.OCCNCCO NCYJUZHZLNZTOO-UHFFFAOYSA-N 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
229960003887 dichlorophen Drugs 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
ZCSZXTSQJLMFAT-UHFFFAOYSA-N ethane 2-(2-hydroxyethylamino)ethanol Chemical compound CC.C(CO)NCCO ZCSZXTSQJLMFAT-UHFFFAOYSA-N 0.000 description 1
PTQOIJLMVNBXPI-UHFFFAOYSA-N ethene;2-phenylphenol Chemical group C=C.OC1=CC=CC=C1C1=CC=CC=C1 PTQOIJLMVNBXPI-UHFFFAOYSA-N 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
238000005562 fading Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
239000003517 fume Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229920006270 hydrocarbon resin Polymers 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 1
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 1
YBEFXFBAXWUBNQ-UHFFFAOYSA-N n-methylmethanamine;propan-1-amine Chemical compound CNC.CCCN YBEFXFBAXWUBNQ-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229940079938 nitrocellulose Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229950006768 phenylethanolamine Drugs 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
125000005506 phthalide group Chemical group 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229920006267 polyester film Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920001470 polyketone Polymers 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
230000002028 premature Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000007639 printing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
VPJDULFXCAQHRC-UHFFFAOYSA-N prop-2-enylurea Chemical compound NC(=O)NCC=C VPJDULFXCAQHRC-UHFFFAOYSA-N 0.000 description 1
GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000005031 sulfite paper Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
238000007651 thermal printing Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940012185 zinc palmitate Drugs 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1

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
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof

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)

CA298,181A 1977-03-04 1978-03-03 Traduction non-disponible Expired CA1099100A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US774,385		1977-03-04
US05/774,385 US4180405A (en)	1977-02-25	1977-03-04	Heat-sensitive recording composition with mixed color precursors

Publications (1)

Publication Number	Publication Date
CA1099100A true CA1099100A (fr)	1981-04-14

Family

ID=25101073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA298,181A Expired CA1099100A (fr)	1977-03-04	1978-03-03	Traduction non-disponible

Country Status (7)

Country	Link
JP (1)	JPS53110537A (fr)
AU (1)	AU3382978A (fr)
BR (1)	BR7801273A (fr)
CA (1)	CA1099100A (fr)
DE (1)	DE2809038A1 (fr)
FR (1)	FR2382338A1 (fr)
GB (1)	GB1563175A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4151748A (en) *	1977-12-15	1979-05-01	Ncr Corporation	Two color thermally sensitive record material system
JPS5630894A (en) *	1979-08-24	1981-03-28	Mitsui Toatsu Chem Inc	Heat-sensitive recording sheet
US4500354A (en) *	1982-09-27	1985-02-19	Graphic Controls Corp.	Heat sensitive recording papers
US4675705A (en) *	1985-06-10	1987-06-23	Labelon Corporation	Heat sensitive coating

1978
- 1978-02-20 GB GB663678A patent/GB1563175A/en not_active Expired
- 1978-03-02 DE DE19782809038 patent/DE2809038A1/de not_active Withdrawn
- 1978-03-02 BR BR7801273A patent/BR7801273A/pt unknown
- 1978-03-03 AU AU33829/78A patent/AU3382978A/en active Pending
- 1978-03-03 JP JP2441278A patent/JPS53110537A/ja active Pending
- 1978-03-03 CA CA298,181A patent/CA1099100A/fr not_active Expired
- 1978-03-03 FR FR7806238A patent/FR2382338A1/fr active Granted

Also Published As

Publication number	Publication date
FR2382338A1 (fr)	1978-09-29
AU3382978A (en)	1979-09-06
GB1563175A (en)	1980-03-19
DE2809038A1 (de)	1978-09-07
FR2382338B3 (fr)	1980-12-05
BR7801273A (pt)	1979-04-03
JPS53110537A (en)	1978-09-27

Legal Events

Date	Code	Title	Description
1998-04-14	MKEX	Expiry

Publication	Publication Date	Title
US4097288A (en)	1978-06-27	Heat sensitive recording composition containing a complexed phenolics and a spiropyran or leuco lactone
US4180405A (en)	1979-12-25	Heat-sensitive recording composition with mixed color precursors
EP0227740B1 (fr)	1989-11-15	Procede et element de mise en image thermique
US4720450A (en)	1988-01-19	Thermal imaging method
US4020232A (en)	1977-04-26	Heat-sensitive recording sheets
US3916068A (en)	1975-10-28	Heat sensitive recording material containing decolorizing agent
US4904572A (en)	1990-02-27	Thermographic recording materials and coating composition therefor
US4818742A (en)	1989-04-04	Heat sensitive recording element
CA1099100A (fr)	1981-04-14	Traduction non-disponible
US5846901A (en)	1998-12-08	Color-forming compounds and their use in carbonless imaging
US4025090A (en)	1977-05-24	Pressure-sensitive or heat-sensitive recording material
US5811367A (en)	1998-09-22	Pressure-sensitive copying material
EP0151733B1 (fr)	1988-06-08	Matériau d'enregistement sensible à la chaleur, formateur de couleur et sa préparation
EP0273418A2 (fr)	1988-07-06	Matériau d'enregistrement sensible à la chaleur utilisant des composés chromogéniques
DE3783005T2 (de)	1993-05-19	Aufzeichnungsmaterialblatt mit farbstoffbildner.
AU605792B2 (en)	1991-01-24	Recording material
JP4293319B6 (ja)	2010-07-21	秘密保持特性を有する感熱性記録材
JP4293319B2 (ja)	2009-07-08	秘密保持特性を有する感熱性記録材
JPH0239987A (ja)	1990-02-08	発色性記録材料
JPH02122981A (ja)	1990-05-10	感熱記録体
JPS61165380A (ja)	1986-07-26	フタリド誘導体、その製造方法およびその誘導体を用いた記録体
JPS6236468A (ja)	1987-02-17	フタリド誘導体、およびその誘導体を用いた記録体
JPS60225784A (ja)	1985-11-11	感熱記録材料
JPS6251680A (ja)	1987-03-06	フタリド誘導体、およびその誘導体を用いた記録体
JPS63120760A (ja)	1988-05-25	フルオレン化合物及びそれを用いた記録材料