CA1307273C - 4,7-diazaphtalides substitues chromogeniques - Google Patents

4,7-diazaphtalides substitues chromogeniques

Info

Publication number: CA1307273C
Authority: CA; Canada
Prior art keywords: compound; lower alkyl; chromogenic; compounds; blue
Prior art date: 1986-08-28
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

CA000542478A

Other languages

English (en)

Inventor

Robert E. Miller

Troy E. Hoover

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.)

Appvion LLC

Original Assignee

Appleton Papers Inc

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.)

1986-08-28

Filing date

1987-07-20

Publication date

1992-09-08

1987-07-20 Application filed by Appleton Papers Inc filed Critical Appleton Papers Inc

1992-09-08 Application granted granted Critical

1992-09-08 Publication of CA1307273C publication Critical patent/CA1307273C/fr

2009-09-08 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

VWSNBLRGRZFZKP-UHFFFAOYSA-N 7h-furo[3,4-b]pyrazin-5-one Chemical class C1=CN=C2C(=O)OCC2=N1 VWSNBLRGRZFZKP-UHFFFAOYSA-N 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 45
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
239000000463 material Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 12
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 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
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 claims 1
-1 aminophenyl Chemical group 0.000 abstract description 12
150000002431 hydrogen Chemical class 0.000 abstract description 4
125000001041 indolyl group Chemical group 0.000 abstract description 3
238000000034 method Methods 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000003593 chromogenic compound Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000004715 keto acids Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000000896 monocarboxylic acid group Chemical group 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000012360 testing method Methods 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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000004888 barrier function Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical class OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
DEZSSEMIAAKOGT-UHFFFAOYSA-N 2,3-dimethylfuro[3,4-b]pyrazine-5,7-dione Chemical compound N1=C(C)C(C)=NC2=C1C(=O)OC2=O DEZSSEMIAAKOGT-UHFFFAOYSA-N 0.000 description 2
CEHPKLRUCVRKFF-UHFFFAOYSA-N 5,6-dimethylpyrazine-2,3-dicarboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C(O)=O)N=C1C CEHPKLRUCVRKFF-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000004927 clay Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000011161 development Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
229920001568 phenolic resin Polymers 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
230000002028 premature Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000011282 treatment Methods 0.000 description 2
DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 1
XMOWAIVXKJWQBJ-UHFFFAOYSA-N 1-ethyl-2-methylindole Chemical compound C1=CC=C2N(CC)C(C)=CC2=C1 XMOWAIVXKJWQBJ-UHFFFAOYSA-N 0.000 description 1
FKHNZQFCDGOQGV-UHFFFAOYSA-N 2,3-dimethylquinoxaline Chemical compound C1=CC=C2N=C(C)C(C)=NC2=C1 FKHNZQFCDGOQGV-UHFFFAOYSA-N 0.000 description 1
VSBVSQIYPNKRMP-UHFFFAOYSA-N 3-(1-ethyl-2-methylindole-3-carbonyl)-5,6-dimethylpyrazine-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=NC(C)=C(C)N=C1C(O)=O VSBVSQIYPNKRMP-UHFFFAOYSA-N 0.000 description 1
PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
ZXZKKQAJHZUVIQ-UHFFFAOYSA-N CCNN(NCC)C1=CC=CC(OCC)=C1 Chemical compound CCNN(NCC)C1=CC=CC(OCC)=C1 ZXZKKQAJHZUVIQ-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920000147 Styrene maleic anhydride Polymers 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
239000005083 Zinc sulfide Substances 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
239000001354 calcium citrate Substances 0.000 description 1
WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
229910001634 calcium fluoride Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
229940096529 carboxypolymethylene Drugs 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000010433 feldspar Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
229940099273 magnesium trisilicate Drugs 0.000 description 1
235000019793 magnesium trisilicate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
150000003252 quinoxalines Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000013337 tricalcium citrate Nutrition 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
229910052984 zinc sulfide Inorganic materials 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Color Printing (AREA)
Heat Sensitive Colour Forming Recording (AREA)

CA000542478A 1986-08-28 1987-07-20 4,7-diazaphtalides substitues chromogeniques Expired - Lifetime CA1307273C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US90110886A	1986-08-28	1986-08-28
US901,108		1986-08-28

Publications (1)

Publication Number	Publication Date
CA1307273C true CA1307273C (fr)	1992-09-08

Family

ID=25413607

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000542478A Expired - Lifetime CA1307273C (fr)	1986-08-28	1987-07-20	4,7-diazaphtalides substitues chromogeniques

Country Status (1)

Country	Link
CA (1)	CA1307273C (fr)

1987
- 1987-07-20 CA CA000542478A patent/CA1307273C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2009-09-08	MKEX	Expiry

Publication	Publication Date	Title
US4154463A (en)	1979-05-15	Pressure-sensitive or heat-sensitive recording material containing a carbazolyl methane compound
US4016174A (en)	1977-04-05	Benzoindole phthalides
US4302393A (en)	1981-11-24	Fluoran compounds
FI84823B (fi)	1991-10-15	Kromogeniska foereningar.
US4104437A (en)	1978-08-01	Pressure-sensitive copy system including ureido fluoran chromogenic compounds
US4536220A (en)	1985-08-20	Fluoran derivatives as new compounds and recording system utilizing the same as colorless chromogenic material
US4020068A (en)	1977-04-26	Chromogenic furoquinoxalines
US4007195A (en)	1977-02-08	Heterocyclic substituted fluorans
US4275206A (en)	1981-06-23	Lactone compounds containing an indolizine radical
CA1129855A (fr)	1982-08-17	Lactones contenant un radical heterocyclique
FR2481286A1 (fr)	1981-10-30	Matiere chromogene de la classe des azaphtalides, son procede de preparation, solution chromogene et support d'enregistrement la contenant
US4316036A (en)	1982-02-16	Benzopyranothiazoles
US4291902A (en)	1981-09-29	Recording material employing substituted 3,6-diaminophthalides as color formers
US4334072A (en)	1982-06-08	Lactone compounds containing an indolizine radical
US5004813A (en)	1991-04-02	Chromogenic phthalides and azaphthalides
GB1590913A (en)	1981-06-10	Process for preparing phthalide colourformrs and substituted 5-aminobenzoic acid derivatives
US5041547A (en)	1991-08-20	Chromogenic substituted 4,7-diazaphthalides
US4564679A (en)	1986-01-14	Chromogenic compounds
US4506073A (en)	1985-03-19	Chromenoazaindolizine compounds
US4837210A (en)	1989-06-06	Fluoran derivatives and their use in recording materials
US5024987A (en)	1991-06-18	Recording material
US4187233A (en)	1980-02-05	Pressure-sensitive or heat-sensitive recording material and novel 2,2-diarylchromeno compounds used therein
US4595768A (en)	1986-06-17	3-(substituted phenyl)phthalides
JP2566628B2 (ja)	1996-12-25	フレオラン化合物および記録材料
US4232887A (en)	1980-11-11	Lactone compounds containing an indolizine radical