JPH0248537B2 - - Google Patents

Info

Publication number: JPH0248537B2
Authority: JP; Japan
Prior art keywords: formula; methyl; compound; color; recording paper
Prior art date: 1982-12-27
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

JP61267741A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62161750A (ja

Inventor

Masakichi Yahagi

Tetsuo Igaki

Sinzi Yosinaka

Kousaku Morita

Morikuni Saito

Kimiaki Kinoshita

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.)

Nippon Soda Co Ltd

Shin Nisson Kako Co Ltd

Original Assignee

Nippon Soda Co Ltd

Shin Nisson Kako Co Ltd

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.)

1982-12-27

Filing date

1986-11-12

Publication date

1990-10-25

1982-12-27 Priority claimed from JP57227095A external-priority patent/JPS59120654A/ja

1986-11-12 Application filed by Nippon Soda Co Ltd, Shin Nisson Kako Co Ltd filed Critical Nippon Soda Co Ltd

1986-11-12 Priority to JP61267741A priority Critical patent/JPS62161750A/ja

1987-07-17 Publication of JPS62161750A publication Critical patent/JPS62161750A/ja

1990-10-25 Publication of JPH0248537B2 publication Critical patent/JPH0248537B2/ja

Status Granted legal-status Critical Current

Links

IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
-1 fluoran compound Chemical class 0.000 description 15
150000001875 compounds Chemical class 0.000 description 11
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000004040 coloring Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000463 material Substances 0.000 description 5
239000007900 aqueous suspension Substances 0.000 description 4
239000011324 bead Substances 0.000 description 4
239000004927 clay Substances 0.000 description 4
FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000002245 particle Substances 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229960001755 resorcinol Drugs 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
MVULBFCSAWHERU-UHFFFAOYSA-N 3-(propylamino)phenol Chemical compound CCCNC1=CC=CC(O)=C1 MVULBFCSAWHERU-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
241001561902 Chaetodon citrinellus Species 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000012021 ethylating agents‎ Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012022 methylating agents‎ Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000000243 solution Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 description 1
JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
210000004761 scalp Anatomy 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
- 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
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran 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
- B41M5/26—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
- B41M5/3275—Fluoran 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
- B41M5/26—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
- 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
- B41M5/337—Additives; Binders
- B41M5/3375—Non-macromolecular compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
- 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
- B41M5/3336—Sulfur compounds, e.g. sulfones, sulfides, sulfonamides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP61267741A 1982-12-27 1986-11-12 安息香酸誘導体 Granted JPS62161750A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP61267741A JPS62161750A (ja)	1982-12-27	1986-11-12	安息香酸誘導体

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP57227095A JPS59120654A (ja)	1982-12-27	1982-12-27	フルオラン化合物
JP61267741A JPS62161750A (ja)	1982-12-27	1986-11-12	安息香酸誘導体

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57227095A Division JPS59120654A (ja)	1982-12-27	1982-12-27	フルオラン化合物

Publications (2)

Publication Number	Publication Date
JPS62161750A JPS62161750A (ja)	1987-07-17
JPH0248537B2 true JPH0248537B2 (mo)	1990-10-25

Family

ID=26527501

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61267741A Granted JPS62161750A (ja)	1982-12-27	1986-11-12	安息香酸誘導体

Country Status (1)

Country	Link
JP (1)	JPS62161750A (mo)

1986
- 1986-11-12 JP JP61267741A patent/JPS62161750A/ja active Granted

Also Published As

Publication number	Publication date
JPS62161750A (ja)	1987-07-17

Publication	Publication Date	Title
JPH0237920B2 (mo)	1990-08-28
JPS6189090A (ja)	1986-05-07	感熱記録材料
JPH04992B2 (mo)	1992-01-09
JPH0344920B2 (mo)	1991-07-09
JPH0460436B2 (mo)	1992-09-28
US4642357A (en)	1987-02-10	Chromogenic recording materials
JPS62161750A (ja)	1987-07-17	安息香酸誘導体
JPS5968373A (ja)	1984-04-18	フルオラン化合物
JPS60149665A (ja)	1985-08-07	フルオラン化合物及びそれを用いる感熱記録シ−ト
JPH0248538B2 (mo)	1990-10-25
JPS60123557A (ja)	1985-07-02	フルオラン誘導体、およびその誘導体を用いた記録体
JP2938504B2 (ja)	1999-08-23	呈色性ビス―（インドリル）エチレン化合物とこれを用いた記録材料
JPH0239515B2 (mo)	1990-09-05
JPS5978886A (ja)	1984-05-07	発色性記録材料
JP2562886B2 (ja)	1996-12-11	記録材料
JPS6271692A (ja)	1987-04-02	発色性記録材料
JP2000136180A (ja)	2000-05-16	多環フェノール化合物及びこれを用いた感熱記録材料
JPH0226782A (ja)	1990-01-29	発色性記録材料
JPH01128984A (ja)	1989-05-22	フルオラン化合物およびこれを用いた発色性記録材料
JPH0735481B2 (ja)	1995-04-19	新規なフルオラン化合物およびそれを使用した発色性記録体
JPS61101556A (ja)	1986-05-20	フルオラン化合物とケトンとの付加物ならびにそれを含有する発色性記録体
JPH04122680A (ja)	1992-04-23	感熱記録体
JPH0710954B2 (ja)	1995-02-08	新規なフルオラン化合物およびそれを使用した発色性記録体
JPH02153783A (ja)	1990-06-13	感熱記録体
JPH02263684A (ja)	1990-10-26	感熱記録体