CA2337314A1 - Method for preparing organic pigments - Google Patents
Method for preparing organic pigments Download PDFInfo
- Publication number
- CA2337314A1 CA2337314A1 CA002337314A CA2337314A CA2337314A1 CA 2337314 A1 CA2337314 A1 CA 2337314A1 CA 002337314 A CA002337314 A CA 002337314A CA 2337314 A CA2337314 A CA 2337314A CA 2337314 A1 CA2337314 A1 CA 2337314A1
- Authority
- CA
- Canada
- Prior art keywords
- carbonyl
- group
- organic pigment
- pigment
- alkyl
- 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.)
- Granted
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3324—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic
- C08G65/3326—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic aromatic
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0022—Wet grinding of pigments
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
Abstract
This invention relates to a process for preparing dispersible organic pigments by (a) milling a mixture containing (1) one or more organic pigments, (2) at least about 1 % by weight, relative to the organic pigment, of one or more aromatic polyalkylene oxide dispersants, (3) 0 to about 10 parts by weight, relative to the organic pigment, of a milling liquid in which the organic pigment is substantially insoluble, (4) 0 to about 50% by weight, relative to the organic pigment, of one or more milling additives other than dispersant (2), and (5) 0 to about 20% by weight, relative to the organic pigment, of one or more surface treatment additives;
(b) optionally, adding to the milled pigment (6) one or more liquids in which the organic pigment is substantially insoluble in amounts such that the total solids content is not reduced below about 10%, and (7) one or more multivalent metal salts and/or one or more quaternary ammonium salt; and (c) isolating the milled organic pigment
(b) optionally, adding to the milled pigment (6) one or more liquids in which the organic pigment is substantially insoluble in amounts such that the total solids content is not reduced below about 10%, and (7) one or more multivalent metal salts and/or one or more quaternary ammonium salt; and (c) isolating the milled organic pigment
Claims (10)
1. A process for preparing dispersible organic pigments comprising milling a mixture comprising (a) milling a mixture comprising (1) one or more organic pigments, (2) at least about 1 % by weight, relative to the organic pigment, of one or more aromatic polyalkylene oxide dispersants, (3) 0 to about 10 parts by weight, relative to the organic pigment, of a milling liquid in which the organic pigment is substantially insoluble, (4) 0 to about 50% by weight, relative to the organic pigment, of one or more milling additives other than dispersant (2), and (5) 0 to about 20% by weight, relative to the organic pigment, of one or more surface treatment additives;
(b) optionally, adding to the milled pigment (6) one or more liquids in which the organic pigment is substantially insoluble in amounts such that the total solids content is not reduced below about 10%, and (7) one or more multivalent metal salts and/or one or more quaternary ammonium salt; and (c) isolating the milled organic pigment.
(b) optionally, adding to the milled pigment (6) one or more liquids in which the organic pigment is substantially insoluble in amounts such that the total solids content is not reduced below about 10%, and (7) one or more multivalent metal salts and/or one or more quaternary ammonium salt; and (c) isolating the milled organic pigment.
2. A process according to Claim 1 wherein the organic pigment is a perylene, quinacridone, phthalocyanine, 1,4-diketopyrrolopyrrole, or isoindoline.
3. A process according to Claim 1 wherein the aromatic polyalkylene oxide dispersant is a compound having the formula wherein Ar is an aromatic hydrocarbon group or a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof;
Alk is C2-C6 alkylene;
X represents a direct bond or a -O-, -S-, -NR1-, -SO2-, -CO-, -Alk1-, or -Ar1- bridging group or a chemically reasonable combination of one or more -O-, -S-, -NR1-, -SO2-, -CO-, -Alk1-, or -Ar1- groups, wherein R1 is hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, C7-C16 aralkyl, an aromatic hydrocarbon group, a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof, C2-C8 alkanoyl, C7-C16 aralkanoyl, C7-C11 aroyl, (C1-C6 alkoxy)carbonyl, (C7-C16 aralkoxy)carbonyl, (C6-C10 aryloxy)carbonyl, carbamoyl, (C1-C6 alkylamino)carbonyl, or (C6-C10 arylamino)carbonyl, or R1 is attached to Ar though a direct bond or indirectly through one or more -SO2-, -CO-, or -Alk1- to form a fused-on five- or six-membered ring, Alk1 is C1-C8 alkylene or C5-C7 cycloalkylene, and Ar1 is C6-C10 arylene;
R is hydrogen, C1-C20 alkyl, C2-C20 alkenyl or alkadienyl, C5-C7 cycloalkyl, C5-C7 cycloalkenyl or cycloalkadienyl, C7-C16 aralkyl, an aromatic hydrocarbon group, a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof, C2-C8 alkanoyl, C7-C16 aralkanoyl, C7-C11 aroyl, (C1-C6 alkoxy)carbonyl, (C7-C16 aralkoxy)carbonyl, (C6-C10 aryloxy)carbonyl, carbamoyl, (C1-C6 alkylamino)carbonyl, (C6-C10 arylamino)carbonyl, a sulfonic acid group or a salt, ester, or amide thereof, a carboxylic acid group or a salt, ester, or amide thereof, a phosphoric acid group or a salt, ester, or amide thereof, or, if Y is a direct bond, an amino or ammonium group or a halogen atom;
Y represents a direct bond or a -O-, -S-, -NR2-, -SO2-, -CO-, -Alk2-, or -Ar2- bridging group or a chemically reasonable combination of one or more -O-, -S-, -NR2-, -SO2-, -CO-, -Alk2-, or -Ar2- groups, wherein R2 is hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, C7-C16 aralkyl, an aromatic hydrocarbon group, a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof, C2-C8 alkanoyl, C7-C16 aralkanoyl, C7-C11 aroyl, (C1-C6 alkoxy)carbonyl, (C7-C16 aralkoxy)carbonyl, (C6-C10 aryloxy)carbonyl, carbamoyl, (C1-C6 alkylamino)carbonyl, or (C6-C10 arylamino)carbonyl, with the proviso that when R is alkyl, alkenyl, alkadienyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, aralkyl, an aromatic hydrocarbon group, a heteroaromatic group, alkanoyl, aralkanoyl, aroyl, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, carbamoyl, alkylaminocarbonyl, or arylaminocarbonyl, then R2 can also be attached to R directly though a bond or indirectly through one or more -SO2-, -CO-, or -Alk2- to form a five- or six-membered ring, Alk2 is C1-C8 alkylene or C5-C7 cycloalkylene, and Ar2 is C6-C10 arylene; and m is from about 2 to about 100.
Alk is C2-C6 alkylene;
X represents a direct bond or a -O-, -S-, -NR1-, -SO2-, -CO-, -Alk1-, or -Ar1- bridging group or a chemically reasonable combination of one or more -O-, -S-, -NR1-, -SO2-, -CO-, -Alk1-, or -Ar1- groups, wherein R1 is hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, C7-C16 aralkyl, an aromatic hydrocarbon group, a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof, C2-C8 alkanoyl, C7-C16 aralkanoyl, C7-C11 aroyl, (C1-C6 alkoxy)carbonyl, (C7-C16 aralkoxy)carbonyl, (C6-C10 aryloxy)carbonyl, carbamoyl, (C1-C6 alkylamino)carbonyl, or (C6-C10 arylamino)carbonyl, or R1 is attached to Ar though a direct bond or indirectly through one or more -SO2-, -CO-, or -Alk1- to form a fused-on five- or six-membered ring, Alk1 is C1-C8 alkylene or C5-C7 cycloalkylene, and Ar1 is C6-C10 arylene;
R is hydrogen, C1-C20 alkyl, C2-C20 alkenyl or alkadienyl, C5-C7 cycloalkyl, C5-C7 cycloalkenyl or cycloalkadienyl, C7-C16 aralkyl, an aromatic hydrocarbon group, a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof, C2-C8 alkanoyl, C7-C16 aralkanoyl, C7-C11 aroyl, (C1-C6 alkoxy)carbonyl, (C7-C16 aralkoxy)carbonyl, (C6-C10 aryloxy)carbonyl, carbamoyl, (C1-C6 alkylamino)carbonyl, (C6-C10 arylamino)carbonyl, a sulfonic acid group or a salt, ester, or amide thereof, a carboxylic acid group or a salt, ester, or amide thereof, a phosphoric acid group or a salt, ester, or amide thereof, or, if Y is a direct bond, an amino or ammonium group or a halogen atom;
Y represents a direct bond or a -O-, -S-, -NR2-, -SO2-, -CO-, -Alk2-, or -Ar2- bridging group or a chemically reasonable combination of one or more -O-, -S-, -NR2-, -SO2-, -CO-, -Alk2-, or -Ar2- groups, wherein R2 is hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, C7-C16 aralkyl, an aromatic hydrocarbon group, a heteroaromatic group in which one or more ring atoms are N, O, S, or a combination thereof, C2-C8 alkanoyl, C7-C16 aralkanoyl, C7-C11 aroyl, (C1-C6 alkoxy)carbonyl, (C7-C16 aralkoxy)carbonyl, (C6-C10 aryloxy)carbonyl, carbamoyl, (C1-C6 alkylamino)carbonyl, or (C6-C10 arylamino)carbonyl, with the proviso that when R is alkyl, alkenyl, alkadienyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, aralkyl, an aromatic hydrocarbon group, a heteroaromatic group, alkanoyl, aralkanoyl, aroyl, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, carbamoyl, alkylaminocarbonyl, or arylaminocarbonyl, then R2 can also be attached to R directly though a bond or indirectly through one or more -SO2-, -CO-, or -Alk2- to form a five- or six-membered ring, Alk2 is C1-C8 alkylene or C5-C7 cycloalkylene, and Ar2 is C6-C10 arylene; and m is from about 2 to about 100.
4. A process according to Claim 1 wherein the aromatic polyalkylene oxide dispersant is a compound having the formula wherein Ar is an aromatic hydrocarbon group;
X is a direct bond, O, or -CO-NR1- wherein R1 is hydrogen or alkyl or is attached to the aromatic group through a -CO- group to form an imide;
Alk is ethylene, 1,2-propylene, or a combination thereof;
Y is O;
R hydrogen or C1-C6 alkyl; and m is from about 2 to about 100,
X is a direct bond, O, or -CO-NR1- wherein R1 is hydrogen or alkyl or is attached to the aromatic group through a -CO- group to form an imide;
Alk is ethylene, 1,2-propylene, or a combination thereof;
Y is O;
R hydrogen or C1-C6 alkyl; and m is from about 2 to about 100,
5. A process according to Claim 1 wherein the aromatic polyalkylene oxide dispersant is a compound having the formula wherein Ar is optionally ring-substituted phenyl or naphthyl;
X is a direct bond, O, or -CO-NR1- wherein R1 is attached to the aromatic group through a -CO- group to form an imide;
Alk is ethylene, 1,2-propylene, or a combination thereof;
Y is O;
R hydrogen or C1-C6 alkyl; and m is from about 2 to about 100.
X is a direct bond, O, or -CO-NR1- wherein R1 is attached to the aromatic group through a -CO- group to form an imide;
Alk is ethylene, 1,2-propylene, or a combination thereof;
Y is O;
R hydrogen or C1-C6 alkyl; and m is from about 2 to about 100.
6. A process according to Claim 1 wherein the milled organic pigment is isolated by spray drying or lyophilization.
7. A pigment composition prepared according to the process of Claim 1.
8. A pigmented coating composition containing as pigment a pigment composition prepared according to Claim 1.
9. An aqueous pigment dispersion comprising a conditioned organic pigment prepared by the process according to Claim 1 in an aqueous liquid medium.
10. A coating composition comprising a pigment dispersion according to Claim 9 and an aqueous liquid medium.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/518,747 US6440207B1 (en) | 2000-03-03 | 2000-03-03 | Method for preparing organic pigments |
| US09/518,747 | 2000-03-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2337314A1 true CA2337314A1 (en) | 2001-09-03 |
| CA2337314C CA2337314C (en) | 2010-05-11 |
Family
ID=24065314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2337314A Expired - Fee Related CA2337314C (en) | 2000-03-03 | 2001-02-16 | Method for preparing organic pigments |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6440207B1 (en) |
| EP (1) | EP1132434B1 (en) |
| CA (1) | CA2337314C (en) |
| DE (1) | DE60101399T2 (en) |
| MX (1) | MX216964B (en) |
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| EP1648970B1 (en) * | 2003-07-18 | 2008-02-06 | The Lubrizol Corporation | Compositions |
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| US9175168B2 (en) * | 2006-09-14 | 2015-11-03 | Sun Chemical Corporation | Pigments with improved dispersibility |
| DE102006052139A1 (en) * | 2006-11-06 | 2008-05-08 | Clariant International Limited | Universal stir-in pigments |
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| WO2013165770A1 (en) | 2012-05-02 | 2013-11-07 | Lubrizol Advanced Materials, Inc. | Aromatic dispersant composition |
| EP2844688B1 (en) | 2012-05-02 | 2020-06-03 | Lubrizol Advanced Materials, Inc. | Aromatic dispersant composition |
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| KR20210046692A (en) | 2018-08-22 | 2021-04-28 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | Aromatic amide dispersant |
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| GB9806723D0 (en) | 1998-03-28 | 1998-05-27 | Zeneca Ltd | Dispersants |
| US6395804B1 (en) | 1998-12-18 | 2002-05-28 | 3M Innovative Properties Company | Polyelectrolyte dispersants for hydrophobic particles in water-based systems |
| US6258896B1 (en) | 1998-12-18 | 2001-07-10 | 3M Innovative Properties Company | Dendritic polymer dispersants for hydrophobic particles in water-based systems |
| US5935272A (en) | 1999-02-02 | 1999-08-10 | Milliken & Company | Compositions comprising aryloxypolyoxyalkylene naphthalimide derivative colorants |
| US6156116A (en) * | 1999-03-19 | 2000-12-05 | Air Products And Chemicals, Inc. | Conversion of crude phthalocyanine blue from red to green shade in an aqueous environment |
-
2000
- 2000-03-03 US US09/518,747 patent/US6440207B1/en not_active Expired - Lifetime
-
2001
- 2001-02-16 CA CA2337314A patent/CA2337314C/en not_active Expired - Fee Related
- 2001-02-20 EP EP01103566A patent/EP1132434B1/en not_active Revoked
- 2001-02-20 DE DE60101399T patent/DE60101399T2/en not_active Revoked
- 2001-03-01 MX MXPA01002215 patent/MX216964B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2337314C (en) | 2010-05-11 |
| DE60101399D1 (en) | 2004-01-22 |
| MXPA01002215A (en) | 2002-08-06 |
| MX216964B (en) | 2003-10-15 |
| EP1132434A2 (en) | 2001-09-12 |
| EP1132434B1 (en) | 2003-12-10 |
| US6440207B1 (en) | 2002-08-27 |
| EP1132434A3 (en) | 2001-11-14 |
| DE60101399T2 (en) | 2004-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130218 |