JPS6361995B2 - - Google Patents
Info
- Publication number
- JPS6361995B2 JPS6361995B2 JP55053268A JP5326880A JPS6361995B2 JP S6361995 B2 JPS6361995 B2 JP S6361995B2 JP 55053268 A JP55053268 A JP 55053268A JP 5326880 A JP5326880 A JP 5326880A JP S6361995 B2 JPS6361995 B2 JP S6361995B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- color
- styryl
- alkyl group
- derivative
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 benzene ring aldehyde Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000005562 fading Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 238000004040 coloring Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- NLRKCXQQSUWLCH-IDEBNGHGSA-N nitrosobenzene Chemical class O=N[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 NLRKCXQQSUWLCH-IDEBNGHGSA-N 0.000 claims description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 7
- 230000005855 radiation Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- RUJYZLQXRALDKN-UHFFFAOYSA-N 1-ethylindole-3-carbaldehyde Chemical compound C1=CC=C2N(CC)C=C(C=O)C2=C1 RUJYZLQXRALDKN-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 description 1
- PEQQOQHEBDQHEO-UHFFFAOYSA-N 9-hexylcarbazole-2-carbaldehyde Chemical compound C1=C(C=O)C=C2N(CCCCCC)C3=CC=CC=C3C2=C1 PEQQOQHEBDQHEO-UHFFFAOYSA-N 0.000 description 1
- QOBHAZPUGZRPSV-UHFFFAOYSA-N 9-methylcarbazole-2-carbaldehyde Chemical compound C1=C(C=O)C=C2N(C)C3=CC=CC=C3C2=C1 QOBHAZPUGZRPSV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
-
- 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
- B41M5/20—Duplicating or marking methods; Sheet materials for use therein using electric current
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Duplication Or Marking (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5326880A JPS56149489A (en) | 1980-04-21 | 1980-04-21 | Color-developing and color-disappearing material |
| US06/255,374 US4380629A (en) | 1980-04-21 | 1981-04-20 | Styryl-like compounds showing a color-developing and bleaching behavior with improved stability and prolonged lifetime |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5326880A JPS56149489A (en) | 1980-04-21 | 1980-04-21 | Color-developing and color-disappearing material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56149489A JPS56149489A (en) | 1981-11-19 |
| JPS6361995B2 true JPS6361995B2 (enExample) | 1988-11-30 |
Family
ID=12938003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5326880A Granted JPS56149489A (en) | 1980-04-21 | 1980-04-21 | Color-developing and color-disappearing material |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4380629A (enExample) |
| JP (1) | JPS56149489A (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4532237A (en) * | 1984-07-30 | 1985-07-30 | Merck & Co., Inc. | Substituted and bridged pyridines useful as calcium channel blockers |
| US4602263A (en) * | 1984-09-04 | 1986-07-22 | Polaroid Corporation | Thermal imaging method |
| US4826976A (en) * | 1984-09-04 | 1989-05-02 | Polaroid Corporation | Color-shifted dyes with thermally unstable carbamate moiety comprising T-alkoxycarbonyl group |
| US4623896A (en) | 1985-02-04 | 1986-11-18 | Polaroid Corporation | Proportional density recording medium |
| US4720450A (en) * | 1985-06-03 | 1988-01-19 | Polaroid Corporation | Thermal imaging method |
| US4720449A (en) * | 1985-06-03 | 1988-01-19 | Polaroid Corporation | Thermal imaging method |
| US4839335A (en) * | 1987-09-28 | 1989-06-13 | Polaroid Corporation | Heat sensitive recording element |
| US4818742A (en) * | 1987-09-28 | 1989-04-04 | Polaroid Corporation | Heat sensitive recording element |
| US5243052A (en) * | 1990-06-29 | 1993-09-07 | Polaroid Corporation | Mixed carbonate ester derivatives of quinophthalone dyes and their preparation |
| US5278031A (en) * | 1992-10-23 | 1994-01-11 | Polaroid Corporation | Process for thermochemical generation of squaric acid and for thermal imaging, and imaging medium for use therein |
| US7388686B2 (en) * | 2003-02-25 | 2008-06-17 | Zink Imaging, Llc | Image stitching for a multi-head printer |
| US7830405B2 (en) | 2005-06-23 | 2010-11-09 | Zink Imaging, Inc. | Print head pulsing techniques for multicolor printers |
| US8377844B2 (en) * | 2001-05-30 | 2013-02-19 | Zink Imaging, Inc. | Thermally-insulating layers and direct thermal imaging members containing same |
| US7791626B2 (en) * | 2001-05-30 | 2010-09-07 | Zink Imaging, Inc. | Print head pulsing techniques for multicolor printers |
| US7704667B2 (en) * | 2003-02-28 | 2010-04-27 | Zink Imaging, Inc. | Dyes and use thereof in imaging members and methods |
| US8372782B2 (en) | 2003-02-28 | 2013-02-12 | Zink Imaging, Inc. | Imaging system |
| WO2004078874A2 (en) * | 2003-02-28 | 2004-09-16 | Polaroid Corporation | Novel dye complexes and use thereof in imaging members and methods |
| WO2006048412A1 (en) | 2004-11-08 | 2006-05-11 | Freshpoint Holdings Sa | Time-temperature indicating device |
| JP2008540774A (ja) * | 2005-05-12 | 2008-11-20 | ズィンク イメージング エルエルシー | 新規ローダミン色素 |
| FR2888747B1 (fr) | 2005-07-22 | 2007-08-24 | Oreal | Utilisation pour la coloration des fibres keratiniques d'une composition comprenant un colorant de type styrylique ou iminique |
| US7807607B2 (en) * | 2006-05-12 | 2010-10-05 | Zink Imaging, Inc. | Color-forming compounds and use thereof in imaging members and methods |
| FR2907004B1 (fr) * | 2006-10-13 | 2008-12-05 | Oreal | Procede de coloration au moyen d'un colorant de type styrylique ou iminique en combinaison avec un sel de zinc et dispositif pour la mise en oeuvre du procede |
| FR2907002B1 (fr) * | 2006-10-13 | 2009-03-06 | Oreal | Procede de coloration au moyen d'un colorant de type styrylique ou iminique en combinaison avec un acide faible et dispositif pour la mise en oeuvre du procede |
| FR2907003B1 (fr) * | 2006-10-13 | 2008-12-05 | Oreal | Composition comprenant un colorant de type styrylique ou iminique et un compose thiole, procede de coloration et dispositif |
| US7660070B2 (en) * | 2007-03-08 | 2010-02-09 | Esgw Holdings Limited | Quiet high performance seek procedure for disk drives |
| FR2930141B1 (fr) * | 2008-04-16 | 2011-01-21 | Oreal | Traitement de fibres colorees par des composes styryliques ou iminiques, en presence d'acides organiques ou minieraux et de sels de zinc. |
| BRPI0913415B1 (pt) | 2008-06-04 | 2019-09-10 | Gordhanbhai Nathalal Patel | sistema indicador |
| CA2726993C (en) | 2008-06-04 | 2021-06-08 | G. Patel | A monitoring system based on etching of metals |
| FR2950246B1 (fr) * | 2009-09-21 | 2011-12-09 | Oreal | Utilisation de colorants particuliers de type styrylique ou iminique pour la coloration des fibres keratiniques, composition tinctoriale comprenant au moins un tel colorant, procede de mise en oeuvre |
| US10980755B2 (en) | 2015-09-10 | 2021-04-20 | The Regents Of The University Of California | LRH-1 modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975379A (en) * | 1970-12-09 | 1976-08-17 | Bayer Aktiengesellschaft | Dihydroindoles and indolenine dyestuffs |
| US4147862A (en) * | 1974-09-18 | 1979-04-03 | Matsushita Electric Industrial Co., Ltd. | Method of preparing styryl-like compounds |
| JPS5733307B2 (enExample) * | 1974-09-18 | 1982-07-16 |
-
1980
- 1980-04-21 JP JP5326880A patent/JPS56149489A/ja active Granted
-
1981
- 1981-04-20 US US06/255,374 patent/US4380629A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4380629A (en) | 1983-04-19 |
| JPS56149489A (en) | 1981-11-19 |
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