GB1114579A - Inks for ball point pens - Google Patents
Inks for ball point pensInfo
- Publication number
- GB1114579A GB1114579A GB3747965A GB3747965A GB1114579A GB 1114579 A GB1114579 A GB 1114579A GB 3747965 A GB3747965 A GB 3747965A GB 3747965 A GB3747965 A GB 3747965A GB 1114579 A GB1114579 A GB 1114579A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dye
- component
- formula
- copolymer
- ink
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000976 ink Substances 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 6
- 239000000178 monomer Substances 0.000 abstract 5
- 229920001577 copolymer Polymers 0.000 abstract 4
- -1 2-ethylhexyl Chemical group 0.000 abstract 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 3
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical group ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical group ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical group CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 abstract 1
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 abstract 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 abstract 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004056 anthraquinones Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000000295 complement effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N phthalic acid di-n-ethyl ester Natural products CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/16—Writing inks
- C09D11/18—Writing inks specially adapted for ball-point writing instruments
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
A ball-point pen ink comprises a solution in a high boiling point organic solvent of a coloured copolymer which has been prepared from: (a) an aromatic monoethylenically unsaturated compound and/or (b) an ester of a monoethylenically unsaturated carboxylic acid and (c) a dye bearing an ethylenically unsaturated group, by copolymerization of (a) and/or (b) and (c) component (c) may be replaced by: (c) a monoethylenically unsaturated monomer bearing a reactive group and the copolymer obtained is reacted with: (f) a dye bearing a reactive group complementary to the reactive group borne by component (e). In another modification, component (c) is replaced by: (g) a monoethylinecally unsaturated diazotizable monomer and the copolymer obtained is diazotized and then reacted with (h) a coupling component, to form a polymer dye. The coloured copolymer may contain units of (d) one or more further monomers. The high boiling points solvent has a boiling point of not less than 125 DEG C., those specified being 1,2-propylene carbonate, dicyclohexyl carbonate, diphenyl carbonate, adipate and phthalic esters such as diethyl or di-n-butyl phthalate, methyl glycol, ethyl glycol and benzyl alcohol. Monomer (a) is e.g. styrene or a substituted styrene, for instance p-methyl, p-chloro, o-chloro or p-hydroxystyrene. Specified monomers (b) include ethyl, n-butyl, cyclohexyl, 2-ethylhexyl and stearylacrylates, and methylmethacrylate. Suitable dyes (c) are azo, anthraquinone or triphenylmethane dyes containing a vinyl, acrylyl, acrylylamino, acryloyloxyalkyl or acrylyloxyaryl group. Component (e) may be acrylamide, methacrylamide or a derivative thereof and component (g) may be p-aminostyrene. In the examples, ethyl acrylate or methyl methacrylate are copolymerized with a dye of formula <FORM:1114579/C3/1> in solution in n-butyl acetate using azodiisobutyrodinitril as catalyst. Benzyl alcohol is added to the resulting solution, from which the butyl acetate is then removed by distillation, to yield a red ink. When methyl methacrylate is similarly copolymerized with a dye of formula <FORM:1114579/C3/2> an orange-red ink is obtained, with a dye of formula <FORM:1114579/C3/3> a yellow ink is obtained and with a dye of formula <FORM:1114579/C3/4> a violet ink is obtained.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB78365A DE1264651B (en) | 1964-09-03 | 1964-09-03 | Ballpoint pen pastes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1114579A true GB1114579A (en) | 1968-05-22 |
Family
ID=6979847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3747965A Expired GB1114579A (en) | 1964-09-03 | 1965-09-02 | Inks for ball point pens |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE669112A (en) |
| DE (1) | DE1264651B (en) |
| GB (1) | GB1114579A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0396376B1 (en) * | 1989-05-02 | 1994-12-28 | BAUSCH & LOMB INCORPORATED | Polymerizable dye |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4471079A (en) * | 1982-03-04 | 1984-09-11 | Pilot Man-Nen Hitsu Kabushiki Kaisha | Aqueous ink |
| DE4422335A1 (en) | 1994-06-27 | 1996-01-04 | Basf Ag | Dye preparations |
-
1964
- 1964-09-03 DE DEB78365A patent/DE1264651B/en active Pending
-
1965
- 1965-09-02 BE BE669112D patent/BE669112A/xx unknown
- 1965-09-02 GB GB3747965A patent/GB1114579A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0396376B1 (en) * | 1989-05-02 | 1994-12-28 | BAUSCH & LOMB INCORPORATED | Polymerizable dye |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1264651B (en) | 1968-03-28 |
| BE669112A (en) | 1966-03-02 |
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