GB1036700A - Organic pigment - Google Patents
Organic pigmentInfo
- Publication number
- GB1036700A GB1036700A GB1280265A GB1280265A GB1036700A GB 1036700 A GB1036700 A GB 1036700A GB 1280265 A GB1280265 A GB 1280265A GB 1280265 A GB1280265 A GB 1280265A GB 1036700 A GB1036700 A GB 1036700A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- amino
- derivatives
- compounds
- pigments
- 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
- 239000012860 organic pigment Substances 0.000 title abstract 2
- -1 phosphorus halide Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000049 pigment Substances 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 abstract 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 239000003054 catalyst Substances 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
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- GWOWVOYJLHSRJJ-UHFFFAOYSA-L cadmium stearate Chemical compound [Cd+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O GWOWVOYJLHSRJJ-UHFFFAOYSA-L 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 239000000976 ink Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000515 polycarbonate Polymers 0.000 abstract 1
- 239000004417 polycarbonate Substances 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 239000005033 polyvinylidene chloride Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000004753 textile Substances 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Compounds of the formula <FORM:1036700/C4-C5/1> wherein -Y= represents a trivalent radical having the formula <FORM:1036700/C4-C5/2> or <FORM:1036700/C4-C5/3> or derivatives thereof having one or more auxochrome substituents in the anthraquinone nucleus are prepared by reacting 1-amino-9,10-anthraquinone (or a derivative thereof containing one or more auxochrome substituents) with an acylating agent of the formula CH2=Y-COX wherein = Y- has the meaning given above and X represents a halogen atom or a CH2 = Y-COO-group. The reaction is conveniently effected in solution in an organic solvent at room or elevated temperature, generally in the presence of sodium carbonate. A catalyst such as a phosphorus halide or dicyclohexylcarbodiimide may also be used. In addition to the two parent compounds, the examples also illustrate the preparation of derivatives containing bromo, hydroxy, methoxy, phenoxy, sulpho, amino, methylamino, phenylamino and benzamido groups.ALSO:Organic pigments comprise homopolymers of compounds of the formula <FORM:1036700/C3/1> wherein -Y = represents a trivalent radical having the formula <FORM:1036700/C3/2> or derivatives thereof having on the anthraquinone nucleus one or more auxochrome substituents, e.g. halogen atoms or sulpho, hydroxy, alkoxy, phenoxy, amino, alkylamino, phenylamino or benzamido groups. The polymers may be prepared by polymerizing the monomer in bulk, solution, suspension or emulsion using catalysts such as azobisisobutyronitrile, benzoyl peroxide, hydrogen peroxide and potassium persulphate. The pigments are useful for colouring synthetic resins by dispersing the pigment in the resin, e.g. polyvinyl chloride, polyvinylidene chloride, polyethylene, polypropylene, polystyrene and polycarbonates. Such coloured resins may also have incorporated therein plasticizers such as dibutyl phthalate and dioctyl phthalate, and stabilizers such as potassium, barium and cadmium stearate and stearic acid. The pigments may also be used in printing inks, paints and textile printing compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH421065A CH442578A (en) | 1965-03-26 | 1965-03-26 | Process for the production of organic pigments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1036700A true GB1036700A (en) | 1966-07-20 |
Family
ID=4271836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1280265A Expired GB1036700A (en) | 1965-03-26 | 1965-03-25 | Organic pigment |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH442578A (en) |
| GB (1) | GB1036700A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4909806A (en) * | 1987-12-31 | 1990-03-20 | Minnesota Mining And Manufacturing Company | Fluorine- and chromophore-containing polymer |
| US4997897A (en) * | 1990-04-03 | 1991-03-05 | Bausch & Lomb Incorporated | Polymerizable dye |
| US5030701A (en) * | 1987-12-31 | 1991-07-09 | Minnesota Mining And Manufacturing Company | Fluorine- and chromophore-containing polymer |
| AU627873B2 (en) * | 1989-05-02 | 1992-09-03 | Bausch & Lomb Incorporated | 1,4-diaminoanthraquinone derivatives as polymerizable dyes |
| US5362812A (en) * | 1993-04-23 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Reactive polymeric dyes |
| EP0683436A1 (en) | 1994-05-17 | 1995-11-22 | Minnesota Mining And Manufacturing Company | Liquid toners utilizing highly fluorinated solvents |
| US5474580A (en) * | 1992-11-27 | 1995-12-12 | Zeneca Limited | Chemical compounds |
| JP2007154179A (en) * | 2005-11-11 | 2007-06-21 | Canon Inc | Polymer having sulfonic acid group or sulfonic acid ester group and amide group, and electrostatic image developing toner having the polymer |
| KR100989499B1 (en) * | 2005-11-11 | 2010-10-22 | 캐논 가부시끼가이샤 | Polymer having sulfonic acid group or sulfonic acid ester group and amide group and electrostatic latent image developing toner having this polymer |
| US8106113B2 (en) * | 2005-07-01 | 2012-01-31 | Fujifilm Corporation | Ink composition, image forming method and printed article |
| CN103159904A (en) * | 2011-12-15 | 2013-06-19 | 上海暄洋化工材料科技有限公司 | High-molecular polymer dye or pigment with adjustable color and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2974607B2 (en) * | 1996-04-05 | 1999-11-10 | ホーヤ株式会社 | Reactive dye and lens using the same |
-
1965
- 1965-03-25 GB GB1280265A patent/GB1036700A/en not_active Expired
- 1965-03-26 CH CH421065A patent/CH442578A/en unknown
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5030701A (en) * | 1987-12-31 | 1991-07-09 | Minnesota Mining And Manufacturing Company | Fluorine- and chromophore-containing polymer |
| US4909806A (en) * | 1987-12-31 | 1990-03-20 | Minnesota Mining And Manufacturing Company | Fluorine- and chromophore-containing polymer |
| AU627873B2 (en) * | 1989-05-02 | 1992-09-03 | Bausch & Lomb Incorporated | 1,4-diaminoanthraquinone derivatives as polymerizable dyes |
| US4997897A (en) * | 1990-04-03 | 1991-03-05 | Bausch & Lomb Incorporated | Polymerizable dye |
| US5474580A (en) * | 1992-11-27 | 1995-12-12 | Zeneca Limited | Chemical compounds |
| US5703215A (en) * | 1992-11-27 | 1997-12-30 | Zeneca Limited | Water-soluble dyes which are polymerizable containing molecules which contain a nucleophilic group and an electrophilic group |
| US5362812A (en) * | 1993-04-23 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Reactive polymeric dyes |
| US5532111A (en) * | 1993-04-23 | 1996-07-02 | Minnesota Mining And Manufacturing Company | Reactive polymeric dyes |
| US5741620A (en) * | 1993-04-23 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Reactive polymeric dyes |
| EP0683436A1 (en) | 1994-05-17 | 1995-11-22 | Minnesota Mining And Manufacturing Company | Liquid toners utilizing highly fluorinated solvents |
| US8106113B2 (en) * | 2005-07-01 | 2012-01-31 | Fujifilm Corporation | Ink composition, image forming method and printed article |
| JP2007154179A (en) * | 2005-11-11 | 2007-06-21 | Canon Inc | Polymer having sulfonic acid group or sulfonic acid ester group and amide group, and electrostatic image developing toner having the polymer |
| KR100989499B1 (en) * | 2005-11-11 | 2010-10-22 | 캐논 가부시끼가이샤 | Polymer having sulfonic acid group or sulfonic acid ester group and amide group and electrostatic latent image developing toner having this polymer |
| US7935771B2 (en) | 2005-11-11 | 2011-05-03 | Canon Kabushiki Kaisha | Polymer having sulfonic acid group or sulfonic acid ester group and amide group, and toner for developing electrostatic latent image having the polymer |
| CN103159904A (en) * | 2011-12-15 | 2013-06-19 | 上海暄洋化工材料科技有限公司 | High-molecular polymer dye or pigment with adjustable color and preparation method thereof |
| CN103159904B (en) * | 2011-12-15 | 2015-05-20 | 上海暄洋化工材料科技有限公司 | High-molecular polymer dye or pigment with adjustable color and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH442578A (en) | 1967-08-31 |
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