GB1108261A - Novel dispersants for use in organic media - Google Patents
Novel dispersants for use in organic mediaInfo
- Publication number
- GB1108261A GB1108261A GB30581/63A GB3058163A GB1108261A GB 1108261 A GB1108261 A GB 1108261A GB 30581/63 A GB30581/63 A GB 30581/63A GB 3058163 A GB3058163 A GB 3058163A GB 1108261 A GB1108261 A GB 1108261A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- component
- remaining
- groups
- solvatable
- 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
- 239000002270 dispersing agent Substances 0.000 title abstract 11
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 abstract 8
- 239000000049 pigment Substances 0.000 abstract 8
- 229920001577 copolymer Polymers 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 239000000194 fatty acid Substances 0.000 abstract 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 abstract 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- 230000004048 modification Effects 0.000 abstract 4
- 238000012986 modification Methods 0.000 abstract 4
- 239000003921 oil Substances 0.000 abstract 4
- 235000019198 oils Nutrition 0.000 abstract 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 3
- 239000006185 dispersion Substances 0.000 abstract 3
- 229930195729 fatty acid Natural products 0.000 abstract 3
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 abstract 3
- 229920005615 natural polymer Polymers 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 3
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 abstract 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N 3-Methoxy-4,5-methylenedioxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 2
- 229920000180 alkyd Polymers 0.000 abstract 2
- 239000006229 carbon black Substances 0.000 abstract 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 239000010685 fatty oil Substances 0.000 abstract 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 2
- -1 hydroxy fatty acid Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000000944 linseed oil Substances 0.000 abstract 2
- 235000021388 linseed oil Nutrition 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- MUWIANZPEBMVHH-UHFFFAOYSA-N oxiran-2-ylmethyl 4-nitrobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)OCC1OC1 MUWIANZPEBMVHH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002245 particle Substances 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229920001059 synthetic polymer Polymers 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- 239000004408 titanium dioxide Substances 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 abstract 1
- BFRLRGJQKQUFHK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;phthalic acid Chemical compound OCC(CO)(CO)CO.OC(=O)C1=CC=CC=C1C(O)=O BFRLRGJQKQUFHK-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 abstract 1
- XMMRNCHTDONGRJ-UHFFFAOYSA-N 3-(4-nitrophenyl)prop-2-enoic acid Chemical class OC(=O)C=CC1=CC=C([N+]([O-])=O)C=C1 XMMRNCHTDONGRJ-UHFFFAOYSA-N 0.000 abstract 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- 235000021357 Behenic acid Nutrition 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
- 239000004604 Blowing Agent Substances 0.000 abstract 1
- VWYIWOYBERNXLX-KTKRTIGZSA-N Glycidyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CO1 VWYIWOYBERNXLX-KTKRTIGZSA-N 0.000 abstract 1
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000005062 Polybutadiene Substances 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229920003180 amino resin Polymers 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940116226 behenic acid Drugs 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000539 dimer Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000002612 dispersion medium Substances 0.000 abstract 1
- 238000004945 emulsification Methods 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000004426 flaxseed Nutrition 0.000 abstract 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 abstract 1
- 125000005456 glyceride group Chemical group 0.000 abstract 1
- 238000000227 grinding Methods 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000001023 inorganic pigment Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 abstract 1
- 150000004668 long chain fatty acids Chemical class 0.000 abstract 1
- 238000003801 milling Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 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
- 150000002888 oleic acid derivatives Chemical class 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- 239000013638 trimer Substances 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
- C08F2/08—Organic solvent with the aid of dispersing agents for the polymer
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/625—Hydroxyacids
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/11—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids from solid polymers
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- 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
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- 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
- C09D7/45—Anti-settling agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F7/00—Chemical modification of drying oils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Toxicology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Novel dispersants for use in organic media correspond to the formula <FORM:1108261/C3/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links. In a modification, the remaining R group or groups or the group R-C-C-R also provide(s) at least one additional component of the formula <FORM:1108261/C3/2> in which Ar and n are as defined above, the component being attached to one of two adjacent carbon atoms in said R group or R-C-C-R group, the other of the adjacent carbon atoms carrying a hydroxyl group, and the solvatable chain-like component containing at least 12 links per Ar group. The solvatable component may be derived from polymers of hydroxy-fatty acids, epoxy resins, alkyd resins, polyalkylene oxides, polyamides, aminoplasts, polyurethanes, addition polymers and natural polymers. The group Ar may be a benzene, naphthalene, pyridine, quinoline or pyrrole residue and preferably contains one or more polar substituents. The dispersants may be prepared by reacting a compound containing a carboxyl group with one containing an epoxy or a ,b -glycol group, one of said compounds also containing the Ar group and the other the solvatable R group; the esterification reaction can be catalysed by the use of a tertiary amine, e.g. dimethyl lauryl amine. Examples illustrate dispersants made by reacting (1) a methyl methacrylate-glycidyl methacrylate copolymer with p-nitrobenzoic acid (PNB); (2) the same copolymer as in (1) with each of the following acids: benzoic, o- and m-nitrobenzoic, 3,5-dinitrobenzoic, p-chlorobenzoic, p-aminobenzoic, p-toluic, a -naphthoic, p-methoxybenzoic, dimethyl sulphate-quaternized p-aminobenzoic, nicotinic, picolinic and p-nitrocinnamic acids; (3) epoxidized polybutadiene with PNB; (5) a pentaerythritol phthalate alkyd resin (modified with soya bean oil) with glycidyl p-nitrobenzoate; (8) a lauryl methacrylate-butyl methacrylate-glycidyl methacrylate copolymer with PNB; (9) polyhydroxystearic acid with glycidyl methacrylate, copolymerizing the ester product with vinyl toluene, styrene and glycidyl methacrylate, and reacting the copolymer obtained with PNB; (10) a lauryl methacrylate-butyl methacrylate-glycidyl methacrylate copolymer with dinitrobenzoic acid; (12) a liquid epoxy resin with PNB; (13) and (14) a lauryl methacrylate - butyl methacrylate - glycidyl methacrylate copolymer with PNB. In Examples 1, 8, 9 and 10, the copolymers are obtained by solution polymerization of the corresponding monomers using benzoyl peroxide or azodiisobutyronitrile as initiator. The Examples also illustrate the use of the products for dispersing various pigments in organic liquids and their application in paints; organic and inorganic (e.g. titanium dioxide, yellow iron oxide and carbon black) pigments are exemplified.ALSO:Pigments are dispersed in organic media with novel dispersants of the formula <FORM:1108261/C4-C5/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links. In a modification, the remaining R group or groups or the group R-C-C-R also provide at least one additional component of the formula <FORM:1108261/C4-C5/2> The solvatable chain-like component can be derived from a natural or synthetic polymer or from a fatty oil, fatty acid or hydroxy-fatty acid. The pigment may be organic or inorganic; specified inorganic pigments are titanium dioxide, yellow iron oxide and carbon black. Dispersion media specified are toluene/methyl isobutyl ketone, toluene, aliphatic/aromatic hydrocarbon solvent, aliphatic hydrocarbon solvent and white spirit. In Example 6 a dispersant is prepared by reacting (esterifying) polymerized linseed oil with glycidyl p-nitrobenzoate in the presence of dimethyl lauryl amine as catalyst, and used to disperse pigments in xylol, and the dispersion is contrasted with pigment dispersions in xylol containing the corresponding unmodified linseed stand oil.ALSO:The invention comprises novel dispersants for use in organic media of the formula <FORM:1108261/C2/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links. In a modification, the remaining R group or groups or the group R-C-C-R also provide(s) at least one additional component of the formula <FORM:1108261/C2/2> in which Ar and n are as defined above, the component being attached to one of two adjacent carbon atoms in said R group or R-C-C-R group, the other of the adjacent carbon atoms carrying a hydroxyl group, and the solvatable chain-like component containing at least 12 links per Ar group. The solvatable component may be derived from long chain fatty acids, e.g. lauric, myristic, palmitic, oleic, stearic or behenic acid, or a dimer, trimer &c. of a hydroxy fatty acid such as 12-hydroxystearic acid, or from a glyceride or an epoxidized natural oil. The group Ar may be a benzene, naphthalene, pyridine, quinoline or pyrrole residue and preferably contains one or more polar substituents. The dispersants may be prepared by reacting a carboxylic acid compound with an epoxy or a ,b -glycol compound, one of said compounds also containing the Ar group and the other the solvatable R group; the esterification reaction can be catalysed by the use of a tertiary amine, e.g. dimethyl lauryl amine. Examples illustrate dispersants made by reacting p-nitrobenzoic acid with epoxidized soya bean oil and with glycidyl oleate, and linseed oil monoglycerides with p-nitrobenzoyl chloride (in the presence of 2,6-lutidine). These products are illustrated as dispersants for pigment compositions.ALSO:Particles of pigments, pesticides, blowing agents, and liquid particles of insoluble low molecular weight polymers are dispersed in organic media with the aid of novel dispersants of the formula: <FORM:1108261/B1-B2/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links. In a modification, the remaining R group or groups or the group R-C-C-R also provide at least one additional component of the formula: <FORM:1108261/B1-B2/2> The solvatable chain-like component can be derived from a natural or synthetic polymer or from a fatty oil, fatty acid or hydroxyfatty acid. Dispersion may be effected by grinding, milling, emulsification or precipitation.
Priority Applications (24)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB30581/63A GB1108261A (en) | 1963-08-01 | 1963-08-01 | Novel dispersants for use in organic media |
US385497A US3433753A (en) | 1963-08-01 | 1964-07-27 | Paint composition including a dispersant having a solvatable chain-like component |
LU46656D LU46656A1 (en) | 1963-08-01 | 1964-07-30 | |
SE09265/64A SE332475B (en) | 1963-08-01 | 1964-07-30 | |
FR983900A FR1427668A (en) | 1963-08-01 | 1964-07-31 | Dispersing agent in organic media |
NL646408834A NL145148B (en) | 1963-08-01 | 1964-07-31 | PROCESS FOR PREPARING DISPERSIONS. |
CH1008764A CH480089A (en) | 1963-08-01 | 1964-07-31 | Process for the preparation of a dispersion of particles in an organic medium and its use for the preparation of paint |
DE19641719402 DE1719402A1 (en) | 1963-08-01 | 1964-07-31 | Dispersant for organic media |
ES0302731A ES302731A1 (en) | 1963-08-01 | 1964-08-01 | Procedure for obtaining a dispersion of particles. (Machine-translation by Google Translate, not legally binding) |
DK382764A DK131823C (en) | 1963-08-01 | 1964-08-01 | DISPERSION OF PIGMENT PARTICLES IN AN ORGANIC BAG |
AT667464A AT284300B (en) | 1963-08-01 | 1964-08-03 | Paint |
BE658409A BE658409A (en) | 1963-08-01 | 1965-01-15 | |
GB33353/65A GB1159252A (en) | 1963-08-01 | 1965-08-04 | Pigment Dispersions |
US568378A US3505268A (en) | 1963-08-01 | 1966-07-28 | Polymeric dispersant |
BE684916D BE684916A (en) | 1963-08-01 | 1966-08-01 | |
LU51680A LU51680A1 (en) | 1963-08-01 | 1966-08-01 | |
SE10556/66A SE336182B (en) | 1963-08-01 | 1966-08-03 | |
FR72132A FR90499E (en) | 1963-08-01 | 1966-08-04 | Dispersing agent in organic media |
NL666610992A NL150500B (en) | 1963-08-01 | 1966-08-04 | METHOD FOR PREPARING A PAINT COMPOSITION. |
DE1620912A DE1620912C3 (en) | 1963-08-01 | 1966-08-04 | Process for the preparation of modified copolymers starting from copolymers of esters of acrylic, metharrylic or ethacrylic acid and their use as dispersants |
CH1126266A CH515740A (en) | 1963-08-01 | 1966-08-04 | Preparation of dispersing agents containing solvatable |
AT747766A AT294276B (en) | 1963-08-01 | 1966-08-04 | Paint |
MY196996A MY6900096A (en) | 1963-08-01 | 1969-12-31 | Novel dispersants for use in organic media |
MY197060A MY7000060A (en) | 1963-08-01 | 1970-12-31 | Pigment dispersions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB30581/63A GB1108261A (en) | 1963-08-01 | 1963-08-01 | Novel dispersants for use in organic media |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1108261A true GB1108261A (en) | 1968-04-03 |
Family
ID=10309889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30581/63A Expired GB1108261A (en) | 1963-08-01 | 1963-08-01 | Novel dispersants for use in organic media |
Country Status (2)
Country | Link |
---|---|
ES (1) | ES302731A1 (en) |
GB (1) | GB1108261A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4232135A (en) | 1978-01-10 | 1980-11-04 | Imperial Chemical Industries Limited | Coating compositions |
US4323363A (en) * | 1975-09-18 | 1982-04-06 | Cassella Aktiengesellschaft | Dyeing of mixed fibers |
EP0060506A1 (en) * | 1981-03-14 | 1982-09-22 | Hoechst Aktiengesellschaft | Water-thinnable epoxides, method for their preparation and their application |
US4656226A (en) * | 1985-09-30 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Acrylic pigment dispersants made by group transfer polymerization |
US4746739A (en) * | 1984-11-23 | 1988-05-24 | International Paint Public Limited Company | Dispersants |
US4812517A (en) * | 1987-12-28 | 1989-03-14 | E. I. Du Pont De Nemours And Company | Dispersants resistant to color change |
EP1029898A2 (en) * | 1999-02-16 | 2000-08-23 | Dainichiseika Color & Chemicals Mfg. Co. Ltd. | Pigment dispersions, and writing instruments and printers with the dispersions stored therein |
WO2002051946A2 (en) * | 2000-12-22 | 2002-07-04 | Basf Corporation | Pigment dispersion and method of preparing the same |
US6861150B2 (en) | 2001-02-26 | 2005-03-01 | Basf Corporation | Rheology control agent, a method of preparing the agent, and a coating composition utilizing the agent |
US7005473B2 (en) | 2000-12-22 | 2006-02-28 | Basf Corporation | Polymeric pigment dispersant utilized as a grind resin for pigments in solventborne pigment dispersions and method of preparing the same |
US7226971B2 (en) | 2000-12-22 | 2007-06-05 | Basf Corporation | Polyester resin with carbamate functionality, a method of preparing the resin, and a coating composition utilizing the resin |
EP1873190A1 (en) * | 2006-05-30 | 2008-01-02 | Vagotex Windtex S.p.A. | Method for the mechano-chemical treatment of materials comprising at least one polymer in the liquid state and products obtainable by said method |
US7576146B2 (en) * | 2003-12-05 | 2009-08-18 | Sun Chemical Corporation | Polymeric colored dispersants and colorant dispersions containing same |
-
1963
- 1963-08-01 GB GB30581/63A patent/GB1108261A/en not_active Expired
-
1964
- 1964-08-01 ES ES0302731A patent/ES302731A1/en not_active Expired
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4323363A (en) * | 1975-09-18 | 1982-04-06 | Cassella Aktiengesellschaft | Dyeing of mixed fibers |
US4232135A (en) | 1978-01-10 | 1980-11-04 | Imperial Chemical Industries Limited | Coating compositions |
EP0060506A1 (en) * | 1981-03-14 | 1982-09-22 | Hoechst Aktiengesellschaft | Water-thinnable epoxides, method for their preparation and their application |
US4746739A (en) * | 1984-11-23 | 1988-05-24 | International Paint Public Limited Company | Dispersants |
US4656226A (en) * | 1985-09-30 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Acrylic pigment dispersants made by group transfer polymerization |
US4812517A (en) * | 1987-12-28 | 1989-03-14 | E. I. Du Pont De Nemours And Company | Dispersants resistant to color change |
EP1029898A2 (en) * | 1999-02-16 | 2000-08-23 | Dainichiseika Color & Chemicals Mfg. Co. Ltd. | Pigment dispersions, and writing instruments and printers with the dispersions stored therein |
EP1029898A3 (en) * | 1999-02-16 | 2002-10-16 | Dainichiseika Color & Chemicals Mfg. Co. Ltd. | Pigment dispersions, and writing instruments and printers with the dispersions stored therein |
WO2002051946A3 (en) * | 2000-12-22 | 2002-09-12 | Basf Corp | Pigment dispersion and method of preparing the same |
WO2002051946A2 (en) * | 2000-12-22 | 2002-07-04 | Basf Corporation | Pigment dispersion and method of preparing the same |
US6657002B2 (en) | 2000-12-22 | 2003-12-02 | Basf Corporation | Polymeric pigment dispersant utilized as a grind resin for pigments and method of preparing the same |
US7005473B2 (en) | 2000-12-22 | 2006-02-28 | Basf Corporation | Polymeric pigment dispersant utilized as a grind resin for pigments in solventborne pigment dispersions and method of preparing the same |
US7226971B2 (en) | 2000-12-22 | 2007-06-05 | Basf Corporation | Polyester resin with carbamate functionality, a method of preparing the resin, and a coating composition utilizing the resin |
US6861150B2 (en) | 2001-02-26 | 2005-03-01 | Basf Corporation | Rheology control agent, a method of preparing the agent, and a coating composition utilizing the agent |
US7576146B2 (en) * | 2003-12-05 | 2009-08-18 | Sun Chemical Corporation | Polymeric colored dispersants and colorant dispersions containing same |
EP1873190A1 (en) * | 2006-05-30 | 2008-01-02 | Vagotex Windtex S.p.A. | Method for the mechano-chemical treatment of materials comprising at least one polymer in the liquid state and products obtainable by said method |
Also Published As
Publication number | Publication date |
---|---|
ES302731A1 (en) | 1965-03-01 |
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