JPH06239017A - Development sheet for pressure sensitive - Google Patents

Abstract

PURPOSE:To improve the durability of a colored picture and to alleviate yellowing by containing at least one kind of phthalimide carboxylic acid derivative and/or metal salt thereof, which is expressed by the specified general formula, and constituting a development sheet for pressure sensitive copy paper on a supporting body. CONSTITUTION:A development sheet for pressure sensitive copy paper is constituted on a supporting body by containing at least one kind of phthalimide carboxylic acid derivative and/or metal salt thereof, which is expressed by the general formula. In this formula, R represent alkyl group, aralkyl group or aryl group, and X1 and X2 represent hydrogen atom, alkyl group, alkoxy group, nitro group of halogen atom. Thus, especially light-proof, plasticizer resistance and waterproof are improved. Yellowing caused by the light of the development sheet and NOx is alleviated.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a color-developing sheet for pressure-sensitive copying paper, and more particularly, it improves the light resistance, plasticizer resistance and water resistance of a colored image and prevents the color-developing sheet from being yellowed by light or NOx. The present invention relates to a reduced color developing sheet for pressure-sensitive copying paper.

[0002]

2. Description of the Related Art Generally, a pressure-sensitive copying paper comprises a sheet (CB paper) coated with microcapsules of a non-volatile organic solvent containing an electron-donating color forming compound and an aqueous coating composition containing an electron-accepting compound. The coated sheets (CF paper) are made to face each other, and the microcapsules are destroyed by the printing pressure of a ballpoint pen, typewriter, etc.
This is a system in which an electron-donating color-forming compound that has flowed out is brought into contact with an electron-accepting compound to develop a color.

Therefore, by changing the combination of the microcapsule layer having the electron-donating color-forming compound and the electron-accepting compound layer, it is possible to make a large number of copies, and a single-leaf color-sensitive pressure-sensitive copying paper. It is also possible to manufacture (SC paper).

The electron-donating color-forming compound used in the production of the CB paper is selected from various electron-donating color-forming compounds such as triarylmethane compounds, diarylmethane compounds and fluorane compounds. At least one kind is used by being dissolved in a non-volatile organic solvent and microencapsulated.

On the other hand, as the electron-accepting compound, inorganic solid acids such as acid clay and activated clay which have been conventionally disclosed in US Pat. No. 2712507, JP-B-40-9309 and JP-B-42-20144. Oil-soluble phenol-formaldehyde resins and polyvalent metal salts of the resins disclosed in the publications, etc., and JP-B-49-10856, JP-B-51-25174, and JP-B-52-13.
Substituted salicylic acid polyvalent metal salts disclosed in Japanese Unexamined Patent Publication No. 27, etc., and polyvalent metal salts of salicylic acid resins disclosed in Japanese Unexamined Patent Publication Nos. 63-132857 and 63-112537. Many other compounds have been proposed.

The conditions that the color-developing sheet for pressure-sensitive copying paper should have are: (1) little decrease in color-developing ability over time (2) little yellowing of the color-developing surface (3) storage of color-developed image Excellent stability (for example, light resistance, plasticizer resistance, and water resistance) (4) Easy preparation of a color-developing sheet such as coating.

When these conditions are examined, various problems can be raised in the color developing sheet for pressure-sensitive copying paper using the above-mentioned currently proposed electron-accepting compound.

For example, the inorganic solid acid absorbs gas and moisture in the air during storage to cause yellowing of the paper surface and deterioration of color development performance. Substituted phenols have insufficient color development performance and poor storage stability of color images. p-substituted phenol
The formaldehyde resin is such that the coated paper gradually turns yellow upon irradiation with sunlight, fluorescent light, or during storage, and the storage stability (especially plasticizer resistance) of the color image is low. It is difficult to say that the polyvalent metal salt of substituted salicylic acid, a mixture of the compounds, and the like have sufficient light resistance, water resistance, and heat resistance of a color image. Further, the polyvalent metal salt of salicylic acid resin is an electron-accepting compound which is well-balanced among the conventional electron-accepting compounds in terms of color density, storage stability of the color image and yellowing of the color developing sheet. The composition has a softening point in addition to the melting point. Therefore, if the dispersion is stored near the softening point or subjected to heat history during coating, the performance may change or coating failure may occur.

[0009]

The object of the present invention is to improve the light fastness, plasticizer fastness and water fastness of a color image,
Another object of the present invention is to provide a color developing sheet for pressure-sensitive copying paper in which yellowing of the color developing sheet due to light or NOx is reduced.

[0010]

Means for Solving the Problems The present inventors have arrived at the present invention as a result of extensive studies on a color developing sheet for pressure-sensitive copying paper in order to meet the above demand.

That is, according to the present invention, a general formula (1) is provided on a support.

[0012]

[Chemical 2] (In the formula, R represents an alkyl group, an aralkyl group or an aryl group, X1 and X2 represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom) and / or A color-developing sheet for pressure-sensitive copying paper containing at least one derivative metal salt.

In the phthalimidocarboxylic acid derivative represented by the general formula (1) according to the present invention, R is an alkyl group,
Represents an aralkyl group or an aryl group, preferably an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent And a naphthyl group which may have a phenyl group or a substituent.

The alkyl group and cycloalkyl group of R may have a substituent, for example, having 1 to 20 carbon atoms.
Alkoxy group, C2-20 alkoxyalkyloxy group, C6-20 aryloxy group, C7-20 aryloxyalkyloxy group, C7
-20 aralkyloxy groups, C8-20 aralkyloxyalkyloxy groups, C1-20 alkylthio groups, C7-20 aralkylthio groups, C6-20 arylthio groups, nitro groups, Halogen atom,
It may be mono-substituted or poly-substituted with a substituent such as a hydroxyl group or a cyano group.

The aralkyl group of R and the aryl group in the aryl group may have a substituent, for example, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, and 7 to 7 carbon atoms. 20 aralkyl groups, 6 to 20 carbon atoms
Aryl group, C1-20 alkoxy group, C2-20 alkoxyalkyl group, C2-20 alkoxyalkyloxy group, C2-20 alkenyloxy group, C3-20 Alkenyloxyalkyl group, alkenyloxyalkyloxy group having 3 to 20 carbon atoms, aralkyloxy group having 7 to 20 carbon atoms, and 8 carbon atoms
To aralkyloxyalkyl groups having 8 to 20 carbon atoms
Aralkyloxyalkyloxy group having 6 to 20 carbon atoms
Aryloxy group, C7-20 aryloxyalkyl group, C7-20 aryloxyalkyloxy group, C2-20 alkylcarbonyl group, C3-20 alkenylcarbonyl group, carbon number 8-2
An aralkylcarbonyl group having 0, an arylcarbonyl group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkenyloxycarbonyl group having 3 to 20 carbon atoms, an aralkyloxycarbonyl group having 8 to 20 carbon atoms,
Aryloxycarbonyl group having 7 to 20 carbon atoms, alkylcarbonyloxy group having 2 to 20 carbon atoms, and 3 to 2 carbon atoms
0 alkenylcarbonyloxy group, C8-20 aralkylcarbonyloxy group, C7-20 arylcarbonyloxy group, C14-20 aralkyloxyaralkyl group, C1-20 alkylthio group, carbon Aralkylthio group having 7 to 20 carbon atoms and 6 to 2 carbon atoms
It may be mono- or poly-substituted with a substituent such as an arylthio group, a nitro group, a formyl group, a halogen atom, a hydroxyl group, a cyano group or the like.

Further, the aryl group contained in these substituents is further an alkyl group having 1 to 6 carbon atoms and 1 to 6 carbon atoms.
May be substituted with an alkoxy group, an alkylthio group having 1 to 6 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, an aralkyloxy group having 7 to 10 carbon atoms, a hydroxyl group, a halogen atom or the like.

More preferably, R is an alkyl group having 1 to 8 carbon atoms which may have a substituent, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and 7 carbon atoms which may have a substituent. A 24 aralkyl group or an aryl group having 6 to 24 carbon atoms which may have a substituent.

Specific examples of R include, for example, a methyl group,
Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, 4-methyl-
2-pentyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group Group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 3,
5-dimethylcyclohexyl group, methoxymethyl group, 2
-Methoxyethyl group, 3-ethoxypropyl group, 4-n
-Propoxybutyl group, 3-t-butoxycyclopentyl group, 3,5-dimethoxycyclohexyl group, 6-
(2'-methoxyethyl) oxyhexyl group, 8-
(3′-n-butoxypropyl) oxyoctyl group, 2
-Phenoxyethyl group, 3- (2'-chlorophenyl)
Oxypropyl group, 4- (3'-methylphenyl) oxybutyl group, 4- (4'-methoxyphenyl) oxycyclohexyl group, 3- (2 ', 6'-dimethylphenyl) oxycycloheptyl group, 2- (2 '-N-propylphenyl) oxyethyloxymethyl group, 7- (3'
-Phenoxypropyl) oxyheptyl group, 2-benzyloxyethyl group, 5-phenethyloxypentyl group,
3- (4'-methylbenzyl) oxypropyl group, 2-
(Α-methylbenzyloxymethyl) oxyethyl group,
3- (2'-benzyloxyethyl) oxypropyl group, phenylthiomethyl group, 2- (3'-methylphenyl) thioethyl group, 4- (4'-methoxyphenyl) thiobutyl group, 3- (2'-chlorophenyl) ) Thiocyclopentyl group, 3-benzylthiopropyl group, 2-phenethylthioethyl group, 4- (3'-chlorobenzyl) thiocyclohexyl group, 4- (4'-methylthiophenethyl) thiobutyl group, 2-chloroethyl group, 5 , 5, 5,
-Trichloropentyl group, 8-hydroxyoctyl group,
Benzyl group, α-methylbenzyl group, α-ethylbenzyl group, cumyl group, phenethyl group, α-methylphenethyl group, α, α-dimethylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methyl group Benzyl group,
4-isopropylbenzyl group, 4-allylbenzyl group,
4-benzylbenzyl group, 4-phenethylbenzyl group,
4-phenylbenzyl group, 4- (4'-methylphenyl) benzyl group, 4-methoxybenzyl group, 4-n-butoxybenzyl group, 3,4-dimethoxybenzyl group, 4
-Methoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenoxybenzyl group, 3-phenoxybenzyl group, 4-hydroxy Benzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group,
2,4-dichlorobenzyl group, 2,5-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,6-dichlorobenzyl group, 2,4,6
-Trichlorobenzyl group, 2-furfuryl group, diphenylmethyl group, 3-phenylpropyl group, phenyl group,
1-naphthyl group, 2-naphthyl group, 3-freel group, 3
-Thienyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4
-N-propylphenyl group, 4-isopropylphenyl group, 4-n-butylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-n-
Pentylphenyl group, 4-isopentylphenyl group, 4
-N-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-tert-octylphenyl group, 4-n-decylphenyl group, 4-n-
Dodecylphenyl group, 4-cyclopentylphenyl group,
4-cyclohexylphenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-vinylphenyl group, 2-vinylphenyl group, 4-allylphenyl group, 2-allylphenyl group, 4-benzylphenyl group, 2- Benzylphenyl group, 4-cumylphenyl group,
4- (4'-methoxycumyl) phenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methoxyphenyl) phenyl group, 4- (2'-methoxyphenyl) Phenyl group, 4-
(4′-chlorophenyl) phenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propoxyphenyl group, 4-iso Propoxyphenyl group, 4-n-butoxyphenyl group, 4-t
ert-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 4-
n-hexyloxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-
n-dodecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 4-ethyl-1-naphthyl group, 6-n
-Butyl-2-naphthyl group, 2-methoxy-1-naphthyl group, 4-methoxy-1-naphthyl group, 5-ethoxy-
1-naphthyl group, 4-methoxymethylphenyl group, 4-
Ethoxymethylphenyl group, 4-n-butoxymethylphenyl group, 3-methoxymethylphenyl group, 4- (2 '
-Methoxyethyl) phenyl group, 4- (2'-ethoxyethyl) oxyphenyl group, 4- (2'-n-butoxyethyl) oxyphenyl group, 4- (3'-ethoxypropyl) oxyphenyl group, 4- Vinyloxyphenyl group, 4-allyloxyphenyl group, 4- (4'-pentenyl) oxyphenyl group, 4-allyloxy-1-naphthyl group, 4-allyloxymethylphenyl group, 6-benzyloxy-2-naphthyl group , 4-benzyloxy-1
-Naphthyl group, 7-benzyloxy-2-naphthyl group,
4-benzyloxyphenyl group, 2-benzyloxyphenyl group, 4-phenethyloxyphenyl group, 4-
(4'-chlorobenzyl) oxyphenyl group, 4-
(4'-methylbenzyl) oxyphenyl group, 4-
(4'-Methoxybenzyl) oxyphenyl group, 4-
(3'-Ethoxybenzyl) oxyphenyl group, 4-
(Benzyloxymethyl) phenyl group, 4- (2'-benzyloxyethyl) oxyphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-phenoxyphenyl group, 4- (4'-methylphenyl) oxy Phenyl group, 4- (4'-methoxyphenyl) oxyphenyl group, 4- (4'-chlorophenyl) oxyphenyl group, 4-phenoxy-1-naphthyl group, 4-phenoxymethylphenyl group, 4- (2'- Phenoxyethyl)
Oxyphenyl group, 4- [2 '-(4 "-methoxyphenyl) oxyethyl] oxyphenyl group, 4- [2'-
(4 "-methylphenyl) oxyethyl] oxyphenyl group, 4- [2 '-(4" -chlorophenyl) oxyethyl] oxyphenyl group, 4-acetylphenyl group, 3
-Acetylphenyl group, 2-acetylphenyl group, 4-
Ethylcarbonylphenyl group, 4-n-butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1-
Naphthyl group, 4-allylcarbonylphenyl group, 4-benzylcarbonylphenyl group, 4- (4'-methylbenzylcarbonyl) phenyl group, 4-phenylcarbonylphenyl group, 4- (4'-methylphenylcarbonyl)
Phenyl group, 4- (4'-chlorophenylcarbonyl)
Phenyl group, 4-phenylcarbonyl-1-naphthyl group, 4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propoxycarbonylphenyl group, 4-n-butoxycarbonylphenyl group, 4-n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group,
4-ethoxycarbonyl-1-naphthyl group, 6-ethoxycarbonyl-2-naphthyl group, 6-n-butoxycarbonyl-2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4'-chlorobenzyloxycarbonyl) phenyl group, 4-phenethyloxycarbonylphenyl group, 6-benzyloxycarbonyl-2-naphthyl group,
4-phenyloxycarbonylphenyl group, 4- (4 '
-Ethylphenyloxycarbonyl) phenyl group, 4-
(4'-chlorophenyloxycarbonyl) phenyl group, 4- (4'-ethoxyphenyloxycarbonyl)
Phenyl group, 6-phenyloxycarbonyl-2-naphthyl group, 4-acetoxyphenyl group, 3-acetoxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2
-Ethylcarbonyloxyphenyl group, 4-n-pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 5-acetyloxy- 1-naphthyl group, 6-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyloxyphenyl group, 6-benzylcarbonyloxy-2-naphthyl group, 4-phenylcarbonyloxyphenyl group, 4-
(2'-Methylphenylcarbonyl) oxyphenyl group, 4- (4'-chlorophenylcarbonyl) oxyphenyl group, 4- (2'-chlorophenylcarbonyl) oxyphenyl group, 4-phenylcarbonyloxy-1-
Naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 4-methylthiophenyl group, 2-methylthiophenyl group, 4-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 4 -N
-Butylthiophenyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group,
3-benzylthiophenyl group, 4- (4'-chlorobenzyl) thiophenyl group, 4-phenylthiophenyl group,
3-phenylthiophenyl group, 4- (4'-methylphenyl) thiophenyl group, 4- (4'-methoxyphenyl) thiophenyl group, 4- (4'-chlorophenyl) thiophenyl group, 1- (4'-methylphenyl ) Thiophenyl group, 6-ethylthio-1-naphthyl group, 6-phenylthio-2-naphthyl group, 4-fluorophenyl group, 3
-Fluorophenyl group, 2-fluorophenyl group, 4-
Chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 4-chloro-1-
Naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 4-nitrophenyl group, 3-nitrophenyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formylphenyl group , 4-formyl-1
-Naphthyl group, 1-formyl-2-naphthyl group, 4-hydroxyphenyl group, 3-hydroxyphenyl group, 2-
Hydroxyphenyl group, 4-hydroxy-1-naphthyl group, 6-hydroxy-2-naphthyl group, 4-cyanophenyl group, 2-cyanophenyl group, 6-cyano-2-naphthyl group, 2-chloro-4-nitro Phenyl group, 4-chloro-2-nitrophenyl group, 6-chloro-3-methylphenyl group, 2-chloro-6-methylphenyl group, 4-chloro-2-methylphenyl group, 4-chloro-3-methyl Phenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,
5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-
Trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3 ，
5-dichlorophenyl group, 2,4,6-trichlorophenyl group, 2-methoxy-4-methylphenyl group, 2,6
-Dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 3,4,5
-Trimethoxyphenyl group, 2,4-dichloro-1-naphthyl group, 4- [1'-methyl-1 '-(4 "-hydroxyphenyl) ethyl] phenyl group, 4- (4'-hydroxyphenyl) oxy A phenyl group etc. can be illustrated.

In the phthalimidocarboxylic acid derivative represented by the general formula (1) according to the present invention, X1 and X2 represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom, preferably a hydrogen atom or a carbon atom. Number 1
A chain alkyl group having 10 to 10 carbon atoms, a cyclic alkyl group having 5 to 14 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine atom, a chlorine atom, or a bromine atom, and more preferably a hydrogen atom or a carbon atom having 1 to 1 carbon atoms. A chain alkyl group having 4 carbon atoms, a cyclohexyl group, an alkoxy group having 1 to 4 carbon atoms, and a chlorine atom, and a hydrogen atom is particularly preferable.

The phthalimidocarboxylic acid derivative represented by the general formula (1) according to the present invention has an imide substituent on the same benzene ring. The substitution position of the carboxyl group with respect to the imide substituent is the 3-position or 4-position,
Specifically, the following general formula (1-a) or general formula (1-
The phthalimidocarboxylic acid derivative represented by the general formula (1-b) can be represented by b), and is particularly preferable.

[0021]

[Chemical 3] Specific examples of the phthalimidocarboxylic acid derivative represented by the general formula (1) and the metal salt of the derivative according to the present invention include the phthalimidocarboxylic acid derivatives and metal salts of the derivatives described below. Of course, the present invention is not limited to these.

Exemplified Compound No. 1. Nn-propyl-3-phthalimidocarboxylic acid 1. N- (4'-n-propoxybutyl) -3-phthalimidocarboxylic acid 3. N- [4 '-(4 "-hydroxyphenyl) oxybutyl] -3-phthalimidocarboxylic acid 4. N- [5'-(4" -ethoxybutyl) oxypentyl] -3-phthalimidocarboxylic acid 5. N- (6'-benzyloxyhexyl) -3-phthalimidocarboxylic acid 6. N- (3'-chlorocyclohexyl) -3-phthalimidocarboxylic acid 7. N- (2'-methoxycyclohexyl) -3-phthalimidocarboxylic acid 8. N- (2'-phenethylthioethyl) -3-phthalimidocarboxylic acid 9. Nn-nonyl-3-phthalimidocarboxylic acid 10. N-ethyl-4-phthalimidocarboxylic acid 11. N- (3'-ethoxypropyl) -4-phthalimidocarboxylic acid 12. N- (2'-phenylthioethyl) -4-phthalimidocarboxylic acid 13. N- [3 '-(4 "-hydroxyphenyl) oxypropyl] -4-phthalimidocarboxylic acid 14. N-n-butyl-4-phthalimidocarboxylic acid 15. N- [4'-(2" -ethoxyethyl) Oxybutyl] -4-phthalimidocarboxylic acid 16. N- (4'-benzyloxybutyl) -4-phthalimidocarboxylic acid 17. N-cyclohexyl-4-phthalimidocarboxylic acid 18. N- (4'-methylcyclohexyl) -4-phthalimidocarboxylic acid 19. N-n-octyl-4-phthalimidocarboxylic acid 20. N-benzyl-3-phthalimidocarboxylic acid 21. N- (3'-phenoxybenzyl) -3-phthalimidocarboxylic acid 22. N-cumyl-3-phthalimidocarboxylic acid 23. N-benzyl-4-phthalimidocarboxylic acid 24. N- (4'-methylbenzyl) -4-phthalimidocarboxylic acid 25. N- (2'-chlorobenzyl) -4-phthalimidocarboxylic acid 26. N- (2'-ethylthiobenzyl) -4-phthalimidocarboxylic acid 27. N- (4'-phenylthiobenzyl) -4-phthalimidocarboxylic acid 28. N- (2 ', 4', 6'-trifluorobenzyl) -4-phthalimidocarboxylic acid 29. N- (3'-bromobenzyl) -4-phthalimidocarboxylic acid 30. N-phenyl-3-phthalimidocarboxylic acid 31. N- (2'-naphthyl) -3-phthalimidocarboxylic acid 32. N- (3'-freel) -3-phthalimidocarboxylic acid 33. N- (4'-phenylphenyl) -3-phthalimidocarboxylic acid 34. N- (2'-methylphenyl) -3-phthalimidocarboxylic acid 35. N- (3'-n-butylphenyl) -3-phthalimidocarboxylic acid 36. N- (4'-tert-butylphenyl) -3
-Phthalimidocarboxylic acid 37. N- (4'-cyclohexylphenyl) -3-
Phthalimide carboxylic acid 38. N- (2'-methoxyphenyl) -3-phthalimidocarboxylic acid 39. N- (3'-isopropoxyphenyl) -3-
Phthalimidocarboxylic acid 40. N- (4'-n-octyloxyphenyl)-
3-phthalimidocarboxylic acid 41. N- (4'-phenoxyphenyl) -3-phthalimidocarboxylic acid 42. N- (2'-acetylphenyl) -3-phthalimidocarboxylic acid 43. N- (3'-phenylcarbonylphenyl)-
3-phthalimidocarboxylic acid 44. N- (3'-n-butoxycarbonylphenyl) -3-phthalimidocarboxylic acid 45 N- (4'-benzyloxyphenyl) -3-
Phthalimide carboxylic acid 46. N- (4'-benzylcarbonylphenyl)-
3-phthalimidocarboxylic acid 47. N- (2'-acetyloxyphenyl) -3-
Phthalimide carboxylic acid 48. N- (3'-ethylthiophenyl) -3-phthalimidocarboxylic acid 49. N- (3'-fluorophenyl) -3-phthalimidocarboxylic acid 50. N- (2'-nitrophenyl) -3-phthalimidocarboxylic acid 51. N- (4'-chlorophenyl) -3-phthalimidocarboxylic acid 52. N- (4'-formylphenyl) -3-phthalimidocarboxylic acid 53. N- (3'-hydroxyphenyl) -3-phthalimidocarboxylic acid 54. N- (4'-cyanophenyl) -3-phthalimidocarboxylic acid 55. N- (2 ', 4'-dimethylphenyl) -3-
Phthalimidocarboxylic acid 56. N- (3 ', 5'-dichlorophenyl) -3-
Phthalimidocarboxylic acid 57. N- (5'-methyl-3'-ethylphenyl)
-3-phthalimidocarboxylic acid 58. N-phenyl-4-phthalimidocarboxylic acid 59. N- (3'-phenoxyphenyl) -4-phthalimidocarboxylic acid 60. N- (1'-naphthyl) -4-phthalimidocarboxylic acid 61. N- (2'-freel) -4-phthalimidocarboxylic acid 62. N- (2'-ethylphenyl) -4-phthalimidocarboxylic acid 63. N- (3'-methylphenyl) -4-phthalimidocarboxylic acid 64. N- (4'-methylphenyl) -4-phthalimidocarboxylic acid 65. N- (2 ', 4'-dimethylphenyl) -4-
Phthalimide carboxylic acid 66. N- (3 ', 5'-dimethylphenyl) -4-
Phthalimidocarboxylic acid 67. N- (4'-isopropylphenyl) -4-phthalimidocarboxylic acid 68. N- (2'-chlorophenyl) -4-phthalimidocarboxylic acid 69. N- (3'-chlorophenyl) -4-phthalimidocarboxylic acid 70. N- (4'-bromophenyl) -4-phthalimidocarboxylic acid 71. N- (3'-n-octylphenyl) -4-phthalimidocarboxylic acid 72. N- (4'-methoxyphenyl) -4-phthalimidocarboxylic acid 73. N- (4'-ethoxyphenyl) -4-phthalimidocarboxylic acid 74. N- (2'-n-butylthiophenyl) -4-
Phthalimide carboxylic acid 75. N- (3'-n-decyloxyphenyl) -4
-Phthalimidocarboxylic acid 76. N-phenethyl-4-phthalimidocarboxylic acid 77. N- [4 '-(3 "-methylphenylcarbonyl) phenyl] -4-phthalimidocarboxylic acid 78. N- (4'-tert-butoxycarbonylphenyl) -4-phthalimidocarboxylic acid 79. N- (1'- Phenylethyl) -4-phthalimidocarboxylic acid 80. N- (4'-phenoxyphenyl) -4-phthalimidocarboxylic acid 81. N- (3'-n-propylthiophenyl) -4
-Phthalimidocarboxylic acid 82. N- (3'-bromophenyl) -4-phthalimidocarboxylic acid 83. N- (2 ', 4'-dinitrophenyl) -4-
Phthalimide carboxylic acid 84. N- (2 ', 4', 6'-trichlorophenyl) -4-phthalimidocarboxylic acid 85. N- (2'-formylphenyl) -4-phthalimidocarboxylic acid 86. N- (2 ', 4'-dihydroxyphenyl)-
4-phthalimidocarboxylic acid 87. N- (3 ', 5'-dicyanophenyl) -4-
Phthalimide carboxylic acid 88. N- (2 ', 4', 6'-trimethylphenyl) -4-phthalimidocarboxylic acid 89. N- (5'-ethyl-3'-n-butylphenyl) -4-phthalimidocarboxylic acid 90. N- {4 '-[1 "-methyl-1"-(4'"
-Hydroxyphenyl) ethyl] phenyl} -4-phthalimidocarboxylic acid 91. N- [4 '-(4 "-hydroxyphenyloxy) phenyl] -4-phthalimidocarboxylic acid 92.5-methyl-N- (3'-methylbenzyl)-
3-phthalimidocarboxylic acid 93. 6-Ethyl-N- (2'-naphthyl) -3-phthalimidocarboxylic acid 94. 6-chloro-N-phenyl-3-phthalimidocarboxylic acid 95. 6-Methoxy-N- (4'-n-butylphenyl) -3-phthalimidocarboxylic acid 96. 4,5-Dimethyl-N- (2'-ethylcarbonylphenyl) -3-phthalimidocarboxylic acid 97. 4,6-diethyl-N- (4'-acetyloxyphenyl) -3-phthalimidocarboxylic acid 98. 5,6-dichloro-N- (3'-chlorophenyl) -3-phthalimidocarboxylic acid 99. 4-methyl-6-chloro-N- (2 ', 4'-
Dimethylphenyl) -3-phthalimidocarboxylic acid 100. 3-chloro-N-phenethyl-4-phthalimidocarboxylic acid 101. 5-n-hexyl-N- (4'-n-butylthiobenzyl) -4-phthalimidocarboxylic acid 102. 5-Fluoro-N- (2 ', 4', 6'-trifluorobenzyl) -4-phthalimidocarboxylic acid 103. 5-Ethoxy-N- (3'-phenoxyphenyl) -4-phthalimidocarboxylic acid 104. 6-Ethyl-N- (4'-isopropylphenyl) -4-phthalimidocarboxylic acid 105. 6-n-butoxy-N- (2'-n-butylthiophenyl) -4-phthalimidocarboxylic acid 106. 6-chloro-N- (4'-phenoxycarbonylphenyl) -4-phthalimidocarboxylic acid 107. 3,6-diethyl-N- (4'-acetylthiophenyl) -4-phthalimidocarboxylic acid 108. 3,5-dichloro-N- (2'-formylphenyl) -4-phthalimidocarboxylic acid 109. 5,6-Dimethyl-N- (5'-ethyl-
3'-n-butylphenyl) -4-phthalimidocarboxylic acid

The method for producing the phthalimidocarboxylic acid derivative represented by the general formula (1) according to the present invention is, for example, Die Makr.
omolekular Chemie, 176 , 127 (1975), JP-A-52-83366, JP-A-61-24616.
For details, refer to No. 1 bulletin.

That is, the method for producing the phthalimidocarboxylic acid derivative is a phthalic anhydride derivative having a carboxyl group (eg, pyromellitic anhydride derivative).
And the amine derivative to react with each other to produce an intermediate amic acid, and the intramolecular dehydration reaction of this amic acid to produce a phthalimidocarboxylic acid derivative represented by the general formula (1). Reaction. However, in general, the reaction is carried out continuously.

After the completion of the reaction, the reaction product can be isolated by a usual processing operation. Generally, the phthalimidocarboxylic acid derivative represented by the general formula (1), which is produced according to a known production method, has a relatively high purity.
When the phthalimidocarboxylic acid derivative represented by the general formula (1) or / and the metal salt of the derivative is used as an electron-accepting compound for a color developing sheet for pressure-sensitive copying paper, or the like,
It is desirable to purify to a higher degree of purity,
The purity can be further increased by a known method (eg, recrystallization, column chromatography, etc.).

In the metal salt of the phthalimidocarboxylic acid derivative represented by the general formula (1) according to the present invention, when used as an electron-accepting compound for a color developing sheet for pressure-sensitive copying paper, the metal salt is , Monovalent metal salts such as sodium, potassium, and lithium are included, but when the metal salt is used alone as an electron-accepting compound, it is preferably water-insoluble or water-insoluble divalent, trivalent or It is a tetravalent polyvalent metal salt, more preferably a divalent or trivalent polyvalent metal salt. Specific examples of the polyvalent metal salt, zinc, cadmium, mercury, magnesium, calcium, barium, nickel, tin, lead, gallium, chromium, copper, molybdenum, tungsten, zirconium, strontium, manganese, cobalt, titanium, aluminum, Mention may be made of iron salts. Preferably, zinc, magnesium, calcium, barium, nickel,
Manganese, cobalt or aluminum salts, more preferably zinc or calcium salts, especially
Zinc salts are the preferred metal salts.

Further, a metal salt of the phthalimidocarboxylic acid derivative represented by the general formula (1) according to the present invention, for example, 1
Alkali metal salts such as valent sodium, potassium and lithium salts are usually obtained by adding an alkali metal hydroxide compound, an alkali metal carbonate compound, an alkali metal hydrogen carbonate compound to the phthalimidocarboxylic acid derivative represented by the general formula (1) (for example, , Sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate) in an aqueous solution.

Further, among the metal salts of the phthalimidocarboxylic acid derivative represented by the general formula (1), divalent, trivalent and tetravalent metals are used.
The valent metal salt is prepared by a metathesis method from an aqueous solution of an alkali metal salt of the phthalimidocarboxylic acid derivative represented by the general formula (1) and an aqueous solution of a corresponding water-soluble divalent, trivalent or tetravalent metal compound. It is produced as a metal salt of a sparingly water-soluble or water-insoluble phthalimidocarboxylic acid derivative. At this time, heating may be performed or an organic solvent may coexist as desired.

As the aqueous solution of the alkali metal salt of the phthalimidocarboxylic acid derivative represented by the general formula (1), a plurality of different aqueous solutions of the alkali metal salt of the phthalimidocarboxylic acid derivative represented by the general formula (1) are used. It may be used, for example, divalent, trivalent or tetravalent prepared by using a mixed aqueous solution of an aqueous solution of each alkali metal salt of N-benzyl-4-phthalimidocarboxylic acid and N-phenyl-4-phthalimidocarboxylic acid. The metal salts of 1) are included in the present invention and can be suitably used as an electron-accepting compound for a color developing sheet for pressure-sensitive copying paper.

Examples of the above water-soluble metal compounds include sulfates such as zinc sulfate, magnesium sulfate, calcium sulfate and aluminum sulfate, zinc chloride, magnesium chloride, calcium chloride, barium chloride, nickel chloride, cobalt chloride and aluminum chloride. Chloride, zinc acetate, etc.
An acetic acid salt such as manganese acetate can be used.

The metal salt of the phthalimidocarboxylic acid derivative represented by the general formula (1) produced as described above may sometimes form a solvate such as a hydrate depending on production conditions. Solvates are also suitable as the electron-accepting compound for the color developing sheet for pressure-sensitive copying paper of the present invention. Of course, a metal salt of a phthalimidocarboxylic acid derivative obtained by removing a solvent such as water from the solvate by a known method (for example, drying) can also be used as an electron-accepting compound for the color developing sheet for pressure-sensitive copying paper of the present invention. Can be suitably used as.

The phthalimidocarboxylic acid derivative obtained by the method described above and the metal salt of the derivative have excellent properties as an electron-accepting compound for a color developing sheet for pressure-sensitive copying paper.

To use the phthalimidocarboxylic acid derivative according to the present invention and the metal salt of the derivative as an electron-accepting compound, it is finely pulverized in an aqueous phase by a sand grinding mill or the like, or suspended or dissolved in a solvent. It is preferable to use an appropriate particle size.

In combination with a known electron-accepting compound,
For example, it may be used in combination with an inorganic solid acid such as acid clay, a phenol-formaldehyde resin, a salicylic acid metal salt or a salicylic acid resin.

Furthermore, zinc, magnesium, aluminum, lead, titanium, calcium, cobalt, nickel,
You may use together with at least 1 sort (s) of oxide, hydroxide, or carbonate of polyvalent metal selected from the group which consists of manganese and barium.

The color-developing sheet for pressure-sensitive copying paper of the present invention can be manufactured by a known method without using a special method.

The method for producing a color-developing sheet for pressure-sensitive copying paper using the phthalimidocarboxylic acid derivative represented by the general formula (1) or / and the metal salt of the derivative according to the present invention includes (1) electron acceptance Of preparing an aqueous coating material using an aqueous suspension of a photoactive compound and applying it to a support such as paper (2) Method of plucking during papermaking (3) Solution or suspension of electron-accepting compound in organic compound Any method can be used, such as a method of preparing a coating material by using and coating it on a support.

In order to form an electron-accepting compound layer on a support such as paper by coating, it is desirable that the electron-accepting compound has an appropriate viscosity and coating aptitude. , (2) as an aqueous suspension, or (3) as dissolved or suspended in a solvent, and then mixed with kaolin clay, calcium carbonate, starch, synthetic or natural latex, etc. It is prepared as a paint with a suitable viscosity and coating suitability.

In this coating composition, the proportion of the electron-accepting compound is preferably 5 to 50% of the total solid content, and if the proportion of the electron-accepting compound component is 5% or less, sufficient color developability cannot be exhibited. On the other hand, if it exceeds 50%, the surface properties of the color developing sheet for pressure-sensitive copying paper deteriorate. The coating amount of the coating dry weight 0.5 g / m ² or more, preferably 1 to 10 g / m ^2.

A color-developing sheet for pressure-sensitive copying paper using the phthalimidocarboxylic acid derivative of the present invention and / or a metal salt of the derivative as an electron-accepting compound has a practically sufficient color density, and an inorganic solid acid, Lightfastness of colored images as compared with a color-developing sheet for pressure-sensitive copying paper using a metal salt of a salicylic acid compound represented by p-phenylphenol novolac resin and 3,5-di (α-methylbenzyl) salicylic acid. And excellent plasticizer resistance, and also improved yellowing due to sunlight irradiation and nitrogen oxides, which is extremely advantageous in handling and storage. Furthermore, the storage stability of the dispersion and the coating suitability are practically no problem.

To the color-developing sheet for pressure-sensitive copying paper of the present invention, various known prescriptions for producing a known color-developing sheet for pressure-sensitive copying paper can be added.

[0042]

EXAMPLES The present invention will be described in more detail with reference to production examples and examples, but the present invention is not limited to these production examples and examples. In manufacturing examples and examples,% represents% by weight.

[Production Example of Phthalimidecarboxylic Acid Derivative Represented by General Formula (1) and Zinc Salt of the Derivative] Production Example 1 (Production of Compound of Exemplified Compound No. 11) Stirrer, Reflux Cooler, Dean 200 g of N, N-dimethylacetamide and 100 g of toluene were charged into a container equipped with a Stark water separator and a nitrogen introducing tube, and water in the solvent was removed by azeotropic dehydration. After that, the mixture was cooled to room temperature, and 40 g of trimellitic anhydride was charged under a nitrogen atmosphere. A solution of 22 g of 3-ethoxypropylamine in 50 g of toluene was added dropwise to this solution at 40 to 50 ° C. over 1 hour. Then, after stirring at the same temperature for 4 hours, at 150 to 170 ° C., until there is no more water in the system,
Reflux for about 4 hours. After completion of the reaction, 100 g of the solvent was distilled off and the mixture was cooled, and then the precipitated solid was separated by filtration and dried to obtain 57 g of N- (3-ethoxypropyl) -4-phthalimidocarboxylic acid as a white solid. The yield was 91%, and the melting point of the obtained compound was 78 to 84 ° C.

Production Example 2 (Production of Zinc Salt of Compound of Exemplified Compound No. 17) 600 g of water, 200 g of methanol, N-cyclohexyl-4 synthesized by a method similar to the method described in Production Example 1
20 g of phthalimidocarboxylic acid and 6 g of 50% aqueous sodium hydroxide solution were charged into a reaction vessel and heated and dissolved at 40 ° C. An aqueous solution prepared by dissolving 10 g of zinc sulfate heptahydrate in 220 g of water was added dropwise to this over 1 hour. After stirring for 3 hours, the precipitated crystals were separated by filtration, washed with water and dried to obtain 19 g of zinc N-cyclohexyl-4-phthalimidocarboxylate as white crystals. The yield was 90%, and the melting point of the obtained compound was 270 ° C.

Production Example 3 (Production of Zinc Salt of Exemplified Compound No. 63) In Production Example 2, N- (3′-methylphenyl) was used instead of N-cyclohexyl-4-phthalimidocarboxylic acid.
Zinc N- (3′-methylphenyl) -4-phthalimidocarboxylic acid was obtained by the same method as in Production Example 2 except that -4-phthalimidocarboxylic acid was used.
The yield was 89%, the melting point of the obtained compound was 180-198.
It was ℃.

Production Example 4 (Production of Calcium Salt of Compound of Exemplified Compound 63) 600 g of water, 200 g of methanol and 20 g of N- (3′-methylphenyl) -4-phthalimidocarboxylic acid were charged into a reaction vessel, and the mixture was heated to 50%. 5g calcium hydroxide aqueous solution
Was added dropwise over 1 hour. After stirring for 3 hours, the precipitated crystals were separated by filtration, washed with water and dried, and then calcium N- (3'-methylphenyl) -4-phthalimidocarboxylate 19
g was obtained as white crystals. The yield was 89%, and the melting point of the obtained compound was 270 to 290 ° C. IR (KBr)
1620 cm ^-1

[Method for producing color developing sheet for pressure-sensitive copying paper and method for evaluating performance] An electron-accepting compound was wet-ground in the presence of a small amount of anionic polymer surfactant to prepare an aqueous suspension having a solid content of 40%. It was made a suspension (average particle size 2.5 μm).

Next, an aqueous coating solution (solid content 39%) having the following composition was prepared using this aqueous suspension.

[0049]

[Table 1]

The above water-based paint was applied to wood free paper with a Mayer bar so that the dry application amount was 5 g / m ² , and dried.
A color developing sheet for pressure-sensitive copying paper was prepared.

The performance of the color-developing sheet for pressure-sensitive copying paper obtained as described above was evaluated by the following method.

(1) Color development density (performed in a constant temperature and humidity room at 20 ° C. and 65% RH) Using a commercially available blue color development top paper (N-40 manufactured by Mitsubishi Paper Mills) containing crystal violet lactone as a main pigment, Combined with a color-developing sheet for pressure-sensitive copying paper, color is pressed by an electronic typewriter. The reflectance of the color image is measured with a Σ80 color difference meter at two points, 100 seconds after stamping and 24 hours after stamping, and is displayed as a Y value.

(2) Lightfastness of Colored Image The color-developing sheet for pressure-sensitive copying paper, which was colored by the method described in (1) above, was irradiated with a carbon arc fade meter (manufactured by Suga Test Instruments) for 4 hours, and tested. The reflectance of the post-color image is Σ
Measured with 80 color difference meter, value before test (value after 24 hours stamping)
It is displayed as the difference in Y value from. The lower the Y value and the smaller the difference from the value before the test, the better the light fastness of the color image.

(3) Plasticizer Resistance of Colored Image By the method described in (1), a sheet coated with microcapsules of melamine-formaldehyde resin having dioctyl phthalate (DOP) as a core substance and having an average particle diameter of 5.0 μm. The developed surface of the color-developing color developing sheet for pressure-sensitive copying paper is made to face each other, and then passed through a super calender roll having a linear pressure of 100 Kg / cm. The density of the color image after 7 days of the test is measured with a Σ80 color difference meter, and the difference between the value before the test (the value after 24 hours of engraving) and the Y value is displayed. The lower the Y value and the smaller the difference from the value before the test, the better the plasticizer resistance of the color image.

(4) Water resistance of color-developed image The color-developing sheet for pressure-sensitive copying paper which has been colored by the method described in (1) is immersed in water for 24 hours and then taken out, and the density of the color-developed image after drying is Σ80. Measured with a color difference meter and displayed as Y value. The lower the Y value and the smaller the difference from the pre-test value, the better the water resistance of the color image.

(5) Yellowing by light A color developing sheet for pressure-sensitive copying paper is irradiated with a carbon arc fade meter (manufactured by Suga Test Instruments) for 4 hours, and after the test, Σ8
The BW value was measured with a 0 color difference meter and is shown by the difference from the value of the untreated sheet. A higher BW value and a smaller difference from the pre-test value indicate less yellowing due to light.

(6) Yellowing by NOx Based on JIS L-1055 (testing method for fastness of nitric oxide gas of dyed products and dyes), the color-developing sheet for pressure-sensitive copying paper is stored for 1 hour in a closed container in NO atmosphere. And check the degree of yellowing. One hour later, the BW value was measured using a Σ80 color difference meter, and the difference from the value of the untreated sheet is shown. A higher BW value and a smaller difference from the pre-test value indicate less yellowing due to NOx.

Examples 1 to 7 The phthalimide carboxylic acid derivative represented by the general formula (1) shown in Table 1 below and / or the metal salt of the derivative is used as the electron-accepting compound, and the above pressure-sensitive copying paper is used. A color-developing sheet for pressure-sensitive copying paper was produced according to the method for producing a color-developing sheet for paper.

[0059]

[Table 2]

Comparative Example 1 A color developing sheet for pressure-sensitive copying paper was prepared by using p-phenylphenol-formaldehyde resin as an electron-accepting compound according to the above-described method for producing a color developing sheet for pressure-sensitive copying paper.

Comparative Example 2 A color developing sheet for pressure-sensitive copying paper was prepared according to the above-mentioned method for producing a color developing sheet for pressure-sensitive copying paper using 3,5-di (α-methylbenzyl) salicylate as an electron-accepting compound. It was made.

Table 2 shows Examples 1 to 7 and Comparative Example 1
The results of the light resistance test, the plasticizer resistance test and the water resistance test of the color density and color image of the color developing sheets for pressure-sensitive copying paper obtained in Nos. 3 to 3 are shown.

[0063]

[Table 3]

From the above results, the color-developing sheet for pressure-sensitive copying paper of the present invention has a practically sufficient color-developing density, and the plasticizer resistance of the color-developed image is higher than that of Comparative Example 1. Also,
It can be seen that the color image is superior in light resistance and water resistance as compared with Comparative Example 2.

Table 3 shows Examples 1 to 7 and Comparative Example 1
Of the undeveloped color-developing sheets of the pressure-sensitive copying paper color-developing sheets obtained in Nos. 3 to 3, and yellowing test by light and NOx
The results of the yellowing test by

[0066]

[Table 4]

From this table, the color-developing sheet for pressure-sensitive copying paper of the present invention is superior in light resistance and NOx yellowing resistance as compared with Comparative Example 1.

[0068]

EFFECTS OF THE INVENTION According to the present invention, compared with the conventionally known color developing sheet for pressure-sensitive copying paper, the color-developing image for color-sensitive copying paper has improved light resistance, plasticizer resistance and water resistance. It is now possible to provide seats.

Front page continuation (72) Inventor Jotaro Kuroda 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Mitsui Toatsu Chemical Co., Ltd. (72) Kiyoharu Hasegawa 1190 Kasama-cho, Sakae-ku, Yokohama, Kanagawa Mitsui Toatsu Chemical Co., Ltd. (72) Inventor Kazumi Yoshikawa 1190 Kasamacho, Sakae-ku, Yokohama-shi, Kanagawa Mitsui Toatsu Chemical Co., Ltd. (72) Inventor Masakatsu Nakatsuka 1190, Kasama-cho, Sakae-ku, Yokohama, Kanagawa Mitsui Toatsu Chemical Co., Ltd.

Claims (1)

[Claims] 1. A color-developing sheet for pressure-sensitive copying paper, which comprises at least one phthalimidocarboxylic acid derivative represented by the general formula (1) or / and a metal salt of the derivative on a support. [Chemical 1] (In the formula, R represents an alkyl group, an aralkyl group or an aryl group, and X1 and X2 represent a hydrogen atom, an alkyl group, an alkoxy group, a nitro group or a halogen atom.)