Patent US3945837A successfully refreshed from Google Patents.
US3945837A
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Ink composition
Assignee: Sakura Color Products Corp
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Filing: 1973-07-12
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Granted: 1976-03-23
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Expires: 1993-07-12
Abstract
Abstract An ink composition which comprises an alicyclic hydrocarbon solvent having dissolved therein a resinous binder and a modified dye, said modified dye being at least one species selected from the group consisting of a reaction product obtained by reacting a dye having at least one group of --CO 2 M and --SO 3 M in the molecule wherein M is an alkali metal with an organic ammonium compound and a reaction product obtained by reacting a basic dye with an acid compound.
Inventors
- 👤 Fumio Miyata
- 👤 Yasuji Okuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 15:49
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/16; C09D11/17; C09B; C09B69/00; C09B69/02
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
692 words
In an ink composition for use in marking pens of the type composed of a dye, a binder and a solvent, the improvement which comprises the solvent being selected from the group consisting of the hexane series and having dissolved therein 5 to 35% by weight of the resinous binder and about 5 to 20% by weight of a modified dye, all % weights being based on the weight of the total composition, said modified dye being at least one species selected from the group consisting of a reaction product obtained by reacting a disazo or anthraquinone dye having at least one group of --CO 2 M and --SO 3 M in the molecule wherein M is an alkali metal with an organic ammonium compound and a reaction product obtained by reacting a basic dye having a positively charged nitrogen, sulfur or oxygen atom in the molecular selected from the group consisting of azo, diphenylmethane, triarylmethane, xanthene, acridiene, methine or polymethine, thiazole, azine, oxazine, thiazine, quinoline and authraquinone dyes with an acid compound: said ammonium compound being represented by the formula ##SPC2## ##EQU7## or ##EQU8## wherein R 1 , R 2 , R 3 and R 4 are respectively a saturated or unsaturated hydrocarbon radical having 1 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU9## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 1 , R 2 , R 3 and R 4 has a carbon number of not lower than 4 and the total carbon number of R 1 , R 2 , R 3 and R 4 is in the range of 7 to 55; R 5 is a saturated or unsaturated hydrocarbon radical having 4 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 4 to 40, or ##EQU10## R' being an alkyl or alkenyl having 4 to 20 carbon atoms; R 6 is hydrogen atom, methyl or ethyl group; R 7 is an aliphatic hydrocarbon radical having 4 to 22 carbon atoms; R 8 and R 9 are respectively a hydrocarbon radical having 1 to 10 carbon atoms; R 10 is methyl ethyl butyl or propyl group; R 11 , R 12 and R 13 are respectively a hydrogen atom, a hydrocarbon radical having 1 to 40 carbon atoms, a radical of a hydrocarbon bonded to a hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU11## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 11 , R 12 and R 13 is a radical having a carbon number of not lower than 4 and the total carbon number of R 11 , R 12 and R 13 is in the range of 4 to 50; X is halogen atom and; A is an acid residue; and said acid compound being represented by the formula R.sub.14 Y, ##EQU12## wherein R.sub.14 and R.sub.19 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 7 to 22 carbon atoms, an aromatic hydrocabon radical having 10 to 28 carbon atoms or a saturated or unsaturated alicyclic hydrocarbon radical having 10 to 28 carbon atoms; R.sub.15 is a saturated aliphatic hydrocarbon radical having 2 to 14 carbon atoms; R.sub.16, R.sub.17, R.sub.20 and R.sub.21 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 4 to 22 carbon atoms; R.sub.18 is a saturated aliphatic hydrocarbon radical having 4 to 18 carbon atoms; M is an alkali metal or ammonium; Y is a --CO.sub.2 M, --SO.sub.3 M or --OSO.sub.3 M group wherein M is the same as above.
Claim 2
Dependent Claim
692 words
In an ink composition for use in marking pens of the type composed of a dye, a binder and a solvent, the improvement which comprises the solvent being selected from the group consisting of the hexane series and having dissolved therein 5 to 35% by weight of the resinous binder and about 5 to 20% by weight of a modified dye, all % weights being based on the weight of the total composition, said modified dye being at least one species selected from the group consisting of a reaction product obtained by reacting a disazo or anthraquinone dye having at least one group of --CO 2 M and --SO 3 M in the molecule wherein M is an alkali metal with an organic ammonium compound and a reaction product obtained by reacting a basic dye having a positively charged nitrogen, sulfur or oxygen atom in the molecular selected from the group consisting of azo, diphenylmethane, triarylmethane, xanthene, acridiene, methine or polymethine, thiazole, azine, oxazine, thiazine, quinoline and authraquinone dyes with an acid compound: said ammonium compound being represented by the formula ##SPC2## ##EQU7## or ##EQU8## wherein R 1 , R 2 , R 3 and R 4 are respectively a saturated or unsaturated hydrocarbon radical having 1 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU9## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 1 , R 2 , R 3 and R 4 has a carbon number of not lower than 4 and the total carbon number of R 1 , R 2 , R 3 and R 4 is in the range of 7 to 55; R 5 is a saturated or unsaturated hydrocarbon radical having 4 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 4 to 40, or ##EQU10## R' being an alkyl or alkenyl having 4 to 20 carbon atoms; R 6 is hydrogen atom, methyl or ethyl group; R 7 is an aliphatic hydrocarbon radical having 4 to 22 carbon atoms; R 8 and R 9 are respectively a hydrocarbon radical having 1 to 10 carbon atoms; R 10 is methyl ethyl butyl or propyl group; R 11 , R 12 and R 13 are respectively a hydrogen atom, a hydrocarbon radical having 1 to 40 carbon atoms, a radical of a hydrocarbon bonded to a hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU11## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 11 , R 12 and R 13 is a radical having a carbon number of not lower than 4 and the total carbon number of R 11 , R 12 and R 13 is in the range of 4 to 50; X is halogen atom and; A is an acid residue; and said acid compound being represented by the formula R.sub.14 Y, ##EQU12## wherein R.sub.14 and R.sub.19 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 7 to 22 carbon atoms, an aromatic hydrocabon radical having 10 to 28 carbon atoms or a saturated or unsaturated alicyclic hydrocarbon radical having 10 to 28 carbon atoms; R.sub.15 is a saturated aliphatic hydrocarbon radical having 2 to 14 carbon atoms; R.sub.16, R.sub.17, R.sub.20 and R.sub.21 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 4 to 22 carbon atoms; R.sub.18 is a saturated aliphatic hydrocarbon radical having 4 to 18 carbon atoms; M is an alkali metal or ammonium; Y is a --CO.sub.2 M, --SO.sub.3 M or --OSO.sub.3 M group wherein M is the same as above.
Claim 3
Dependent Claim
402 words
The ink composition according to claim 1, wherein said organic ammonium compound is a compound represented by the formula ##SPC3## ##EQU13## wherein R 1 , R 2 , R 3 and R 4 are respectively a saturated or unsaturated hydrocarbon radical having 1 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU14## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 1 , R 2 , R 3 and R 4 has a carbon number of not lower than 4 and the total carbon number of R 1 , R 2 , R 3 and R 4 is in the range of 7 to 55; R 5 is a saturated or unsaturated hydrocarbon radical having 4 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 4 to 40, or ##EQU15## R' being an alkyl or alkenyl having 4 to 20 carbon atoms; R 6 is hydrogen atom, methyl or ethyl group; R 7 is an aliphatic hydrocarbon radical having 4 to 22 carbon atoms; R 8 and R 9 are respectively a hydrocarbon radical having 1 to 10 carbon atoms; R 10 is methyl, ethyl, butyl or propyl group; R 11 , R 12 and R 13 are respectively a hydrogen atom, a hydrocarbon radical having 1 to 40 carbon atoms, a radical of a hydrocarbon bonded to a hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU16## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 11 , R 12 and R 13 is a radical having a carbon number of not lower than 4 and the total carbon number of R 11 , R 12 and R 13 is in the range of 4 to 50; X is halogen atom and; A is an acid residue.
Claim 4
Dependent Claim
161 words
The ink composition according to claim 2, wherein said organic ammonium compound is a quaternary ammonium compound represented by the formula ##EQU17## wherein R 1 , R 2 , R 3 and R 4 are respectively a saturated or unsaturated hydrocarbon radical having 1 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU18## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 1 , R 2 , R 3 and R 4 have a carbon number of not lower than 4 and the total carbon number of R 1 , R 2 , R 3 and R 4 is in the range of 7 to 55; and X is a halogen atom.
Claim 5
Dependent Claim
13 words
The ink composition according to claim 3, wherein said X is chlorine atom.
Claim 6
Dependent Claim
99 words
The ink composition according to claim 2, wherein said organic ammonium compound is a pyridinium compound represented by the formula ##SPC4## wherein R 5 is a saturated or unsaturated hydrocarbon radical having 4 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 4 to 40, or ##EQU19## R' being an alkyl or alkenyl having 4 to 20 carbon atoms; and X is a halogen atom.
Claim 7
Dependent Claim
13 words
The ink composition according to claim 5, wherein said X is chlorine atom.
Claim 8
Dependent Claim
41 words
The ink composition according to claim 2, wherein said organic ammonium compound is a quinolinium compound represented by the formula ##SPC5## wherein R 7 is an aliphatic hydrocarbon radical having 4 to 22 carbon atoms and X is a halogen atom.
Claim 9
Dependent Claim
13 words
The ink composition according to claim 7, wherein said X is chloride atom.
Claim 10
Dependent Claim
53 words
The ink composition according to claim 2, wherein said organic ammonium compound is a imidazolinium compound represented by the formula ##EQU20## wherein R 8 and R 9 are respectively a hydrocarbon radical having 1 to 10 carbon atoms; R 10 is methyl, ethyl, propyl or butyl group; and A is an acid residue.
Claim 11
Dependent Claim
12 words
The ink composition according to claim 9, wherein A is chloride atom.
Claim 12
Dependent Claim
157 words
The ink composition according to claim 2, wherein said organic ammonium compound is a amine compound represented by the formula ##EQU21## wherein R 11 , R 12 and R 13 are respectively a hydrogen atom, a saturated or unsaturated hydrocarbon radical having 1 to 40 carbon atoms, a radical of a saturated or unsaturated hydrocarbon bonded to a saturated or unsaturated hydrocarbon by a divalent group of --O--, --S--, --COO--, --CONH-- or --NH--, the total carbon number of both hydrocarbons bonded being in the range of 2 to 40, or ##EQU22## R' being an alkyl or alkenyl having 1 to 20 carbon atoms, provided that at least one of R 11 , R 12 and R 13 is a radical having a carbon number of not lower than 4 and the total carbon number of R 11 , R 12 and R 13 is in the range of 4 to 50; and A is an acid residue.
Claim 13
Dependent Claim
14 words
The ink composition according to claim 11, wherein said A is hydrochloric acid residue.
Claim 14
Dependent Claim
42 words
The ink composition according to claim 1, wherein said dye to be reacted with organic ammonium compound has one to two --CO 2 Na groups, one to two --SO 3 Na groups or both --CO 2 Na and SO 3 Na groups.
Claim 15
Dependent Claim
137 words
The ink composition according to claim 1, wherein said acid compound is an acid compound represented by the formula R.sub.14 Y, ##EQU23## ##EQU24## wherein R.sub.14 and R.sub.19 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 7 to 22 carbon atoms, an aromatic hydrocarbon radical having 10 to 28 carbon atoms or a saturated or unsaturated alicyclic hydrocarbon radical having 10 to 28 carbon atoms; R.sub.15 is a saturated aliphatic hydrocarbon radical having 2 to 14 carbon atoms; R.sub.16, R.sub.17, R.sub.20 and R.sub.21 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 4 to 22 carbon atoms; R.sub.18 is a saturated aliphatic hydrocarbon radical having 4 to 18 carbon atoms; M is an alkali metal or ammonium; Y is a --CO.sub.2 M, --SO.sub.3 M or --OSO.sub.3 M group wherein M is the same as above.
Claim 16
Dependent Claim
86 words
The ink composition according to claim 14, wherein said acid compound is an organic alkaline compound rep esented by the formula R.sub.14 Y wherein R 14 is a saturated or unsaturated aliphatic hydrocarbon radical having 7 to 22 carbon atoms, an aromatic hydrocarbon radical having 10 to 28 carbon atoms or a saturated or unsaturated alicyclic hydrocarbon radical having 10 to 28 carbon atoms; and Y is a --CO 2 M, --SO 3 M or --OSO 3 M group wherein M an alkali metal or ammonium.
Claim 17
Dependent Claim
13 words
The ink composition according to claim 15, wherein said M is sodium atom.
Claim 18
Dependent Claim
56 words
The ink composition according to claim 14, wherein said acid compound is an organic alkaline compound represented by the formula ##EQU25## wherein R 15 is a saturated aliphatic hydrocarbon radical having 2 to 14 carbon atoms; R 16 and R 17 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 4 to 22 carbon atoms.
Claim 19
Dependent Claim
13 words
The ink composition according to claim 17, wherein said M is sodium atom.
Claim 20
Dependent Claim
44 words
The ink composition according to claim 14, wherein said acid compound is an organic alkaline compound represented by the formula ##EQU26## wherein R 18 is a saturated aliphatic hydrocarbon radical having 4 to 18 carbon atoms; and M is an alkali metal or ammonium.
Claim 21
Dependent Claim
13 words
The ink composition according to claim 19, wherein said M is sodium atom.
Claim 22
Dependent Claim
69 words
The ink composition according to claim 14, wherein said acid compound is a phosphoric ester represented by the formula ##EQU27## wherein R 19 is a saturated or unsaturated aliphatic hydrocarbon radical having 7 to 22 carbon atoms, an aromatic hydrocarbon radical having 10 to 28 carbon atoms or a saturated or unsaturated alicyclic hydrocarbon radical having 10 to 28 carbon atoms; and M is an alkali metal or ammonium.
Claim 23
Dependent Claim
12 words
The ink composition according to claim 21, wherein M is sodium atom.
Claim 24
Dependent Claim
50 words
The ink composition according to claim 14, wherein said acid compound is a dialkyl phosphoric ester represented by the formula ##EQU28## wherein R 20 and R 21 are respectively a saturated or unsaturated aliphatic hydrocarbon radical having 4 to 22 carbon atoms; and M is an alkali metal or ammonium.
Claim 25
Dependent Claim
13 words
The ink composition according to claim 23, wherein said M is sodium atom.
References Cited (Backward Citations)
US2567963A
Cited
US3748136A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-23 | 1979-09-22 | 1980-03-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-23 | 1983-09-22 | 1984-03-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-23 | 1987-09-22 | 1988-03-23 | $7700.00 | Window Closed / Lapsed |