WO1993002131A1 - Agents dispersants de pigments polyester modifies par une amine - Google Patents

Agents dispersants de pigments polyester modifies par une amine Download PDF

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Publication number
WO1993002131A1
WO1993002131A1 PCT/US1992/005353 US9205353W WO9302131A1 WO 1993002131 A1 WO1993002131 A1 WO 1993002131A1 US 9205353 W US9205353 W US 9205353W WO 9302131 A1 WO9302131 A1 WO 9302131A1
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WIPO (PCT)
Prior art keywords
pigment
dispersing agent
polyester
amine
pigment dispersing
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Ceased
Application number
PCT/US1992/005353
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English (en)
Inventor
Paul H. Lamers
James B. O'dwyer
Gregory J. Mccollum
Charles M. Kania
Martin J. Simon
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PPG Industries Inc
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PPG Industries Inc
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Filing date
Publication date
Application filed by PPG Industries Inc filed Critical PPG Industries Inc
Publication of WO1993002131A1 publication Critical patent/WO1993002131A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • 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
    • C09B67/0088—Non common dispersing agents cationic dispersing agents
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
    • 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

Definitions

  • the present invention relates to pigment dispersing agents; to dispersions of pigments containing such dispersing agents; to a method of preparing such dispersions and to coating compositions containing such dispersions.
  • Pigmented coating compositions are useful for their aesthetic as well as protective features.
  • the coating compositions contain a film-forming resin and a pigment dispersed in a liquid carrier. It is important that the pigment be satisfactorily dispersed throughout the film which results from the application of the coating composition. Accordingly, the pigment must be well dispersed throughout the liquid coating composition. Normally, the pigment is first dispersed in a pigment dispersing agent. The resulting dispersion is then mixed with the main film-forming resin of the composition and other necessary components to produce the final pigmented coating composition.
  • a large number of different dispersants have been used in the manufacture of pigmented coating compositions. Many of the dispersants are low molecular weight surfactants. A problem with these materials is their tendency to exude from the painted film after prolonged weathering resulting in an undesirable appearance.
  • Polymers are also known as dispersing agents. Examples of such polymers are polyesters which have polar groups associated with them such as carboxylic acid and hydroxyl groups which gives them good pigment wetting and dispersing properties. Unfortunately, many of these polymeric pigment dispersing agents provide for poor color strength and often adversely affect the flow and leveling of the pigmented coating compositions which contain the dispersing agents. Also, the resulting pigment dispersions may have high viscosities which make them very difficult to handle.
  • a pigment dispersing agent comprising the reaction product of a polyester having hydroxyl and carboxylic acid groups with from 0.02 to 0.4 millimoles of total amine per gram of polyester, said amine being of the formula:
  • R a is alkylene containing from 2 to 6 carbon atoms and R D is hydroxy-substituted alkyl in which the alkyl group contains from 2 to 12 carbon atoms.
  • the invention also provides for pigment dispersions comprising finely divided pigment in the dispersing agent described immediately above.
  • the invention also provides for a method for preparing such pigment dispersions comprising mixing together under high shear conditions a pigment or an aqueous pigment press cake and a dispersing agent so as to intimately disperse the pigment throughout the dispersing agent described above.
  • the invention also provides for a coating composition which is catalyzed by acid comprising as the principal film-forming resin an active hydrogen-containing material, an aminoplast curing agent, pigment and the pigment dispersing agent described above.
  • Amine-modified polyesters are known for use as pigment dispersing agents.
  • U.S. 3,882,088 discloses polyesters bearing polyethylenimine terminal groups.
  • the polyesters can be prepared by reacting a hydroxyl group or a carboxylic acid group containing polyester with a compound containing a linking group such as a diisocyanate and further reacting with polyethylenimine to form the polyester bearing terminal polyethylenimine groups.
  • the pigment grinding vehicles of U.S. 3,882,088 differ from those of the present invention in that they require a linking group to link the polyester with the polyethylenimine, and secondly, compared with the present invention, they have relatively high residual amine contents, i.e., low amine equivalent weights. The presence of high residual amine contents can adversely affect acid catalyzed cures of the main film-forming resin.
  • U.S. 4,123,422 discloses amide-modified polyester polyols which are formed from reacting a polyester polyol with a primary or secondary amine of the formula:
  • the amide-modified polyesters are disclosed as being useful as polyol components in two-package urethane coating systems.
  • the reference also discloses that pigment can be incorporated into the polyol package by grinding titanium dioxide pigment into the amide polyester polyol at a ratio of 6:1 on a solids basis, i.e., note Example V.
  • U.S. 4,224,212 discloses pigment dispersing agents comprising a poly(lower alkylene)imine chain to which is attached at least two polyester chains by means of salt and/or amide links.
  • the polymer architecture has the polyethylenimine chains internal to the polymer and not as a pendant end group, i.e., two polyester chains are attached to each polyethylenimine group as opposed to the present invention in which the amine group is pendant to the polyester chain.
  • the pigment dispersing agents have relatively high residual amine contents compared with the pigment dispersing agents of the present invention.
  • 4,735,984 discloses pigment dispersing agents comprising the reaction product of polyamines having two or more primary amino groups and/or a secondary amino group with at least one polyisocyanate having two or more isocyanate groups.
  • U.S. 5,000,792 discloses pigment dispersing agents comprising the reaction product of polyesters having a free carboxyl group with an acid value in the range of 10 to 60 with an amine compound of the formula:
  • R ⁇ and R are alkylene radicals which can be the same or different, each containing from 2 to 6 carbon atoms, and R3 is a radical of the formula CH3- or C H5 ⁇ , wherein the reaction is conducted in the range of from about 0.8 to 1.0 equivalent molar ratio of amino groups having reactive hydrogens of said amine compound to free carboxylic acid groups of the polyester.
  • the polyesters which are used in making the pigment dispersing agents of the present invention are produced by reacting a polyhydric alcohol component with a polybasic carboxylic acid component to obtain a polyester containing carboxylic acid groups.
  • the polyhydric alcohols have a functionality of at least two and contain from 2 to 16 carbon atoms, preferably 2 to 8 carbon atoms.
  • Such polyhydric alcohols include diols, triols and higher polyols.
  • Useful diols include alkylene glycols, e.g., ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, neopentyl glycol,
  • Triols and higher polyols include trimethylolethane, trimethylolpropane, glycerol, 1,2,6-hexanetriol and pentaerythritol. Mixtures of polyhydric alcohols can also be used.
  • the polybasic carboxylic acid has a functionality of at least two and can contain from 4 to 36 carbon atoms. It can be an aliphatic carboxylic acid, an alicyclic acid or an aromatic carboxylic acid, providing it has the required number of carbon atoms and proper degree of functionality.
  • aromatic nuclei of aromatic carboxylic acids for example, phthalic acid
  • the aromatic nuclei of aromatic carboxylic acids are regarded as saturated since the double bonds are relatively unreactive. (This is as opposed to the reactivity of an alpha-beta unsaturated acid, for example, fumaric acid.) Therefore, wherever the term "saturated polyester polyol" is utilized, it is understood that this term includes a compound containing aromatic unsaturation.
  • polybasic carboxylic acids useful herein include phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, hexahydrophthalic anhydride, succinic acid, succinic anhydride, glutaric acid, adipic acid, azelaic acid, sebacic acid, dimerized fatty acids and mixtures thereof.
  • the aliphatic carboxylic acids can contain from 4 to 36 carbon atoms while the alicyclic or aromatic carboxylic acids contain from 6 to 14 carbon atoms (inclusive of the number of carbon atoms in the carboxyl group).
  • the dicarboxylic acids are the preferred polybasic carboxylic acids, although minor amounts of more higher functional carboxylic acids, for example, trimellitic acid, can be included with the dicarboxylic acid.
  • the carboxylic acid group-containing polyester is produced using conventional batch or continuous processing techniques with the reaction conditions and ratio of reactants being chosen so as to provide a product having the desired hydroxyl and carboxyl groups.
  • the polyester should have an acid number of from about 0.1 to 30 and preferably from about 5 to 15 (on a solids basis). Acid values less than 0.1 are undesirable because of the difficulty in dispersing basic pigments, whereas acid values greater than 30 are undesirable because of paste instability and high paste viscosities.
  • the hydroxyl value of the polyester is typically at least 20, preferably within the range of 50 to 300 (on a solids basis). Lower hydroxyl values provide insufficient reactive sites for curing.
  • the polyester preferably will have a weight average molecular weight (Mw) of 500 to 100,000, more preferably 800 to 40,000. Molecular weights less than 500 are undesirable because of paste instability, whereas molecular weights greater than 100,000 are undesirable because of high paste viscosities.
  • Mw weight average molecular weight
  • the molecular weights are determined by gel permeation chromatography using a polystyrene standard. Therefore, what is obtained is a polystyrene number. However, for the purpose of the present invention, they are considered molecular weights.
  • the amine which is reacted with the carboxylic acid group-containing polyester is of the formula:
  • R a is alkylene containing from 2 to 6 carbon atoms and R D is hydroxy-substituted alkyl in which the alkyl group contains from 2 to
  • R a is ethylene and R D is hydroxyethyl.
  • Suitable amines include N-aminoethylethanolamine, N-aminopropylethanolamine, N-aminoethylhydroxypropylamine and
  • the amount of amine which is reacted with the polyester is from about 0.02 to 0.4, preferably 0.03 to 0.3 millimoles of total amine per gram of polyester. Amounts less than 0.02 millimoles per gram of polyester are undesirable because the resulting pigment dispersing agent will not have sufficient pigment dispersing properties, whereas amounts greater than 0.4 millimoles per gram of polyester are undesirable because the higher amine contents inhibit acid catalyzed cure, such as an aminoplast cure, when the pigment dispersing agent is incorporated into such curable coating compositions.
  • the equivalent ratio of amine (i.e., equivalents of primary amine group) to carboxylic acid in the polyester is usually from about 0.05 to 1:1. Controlling the equivalent ratio in this manner insures that the resultant pigment dispersing agent will have groups of the structure: H H
  • the reaction of the amine with the polyester is typically conducted by heating the polyester to a temperature of about 120° to
  • the solid pigment, pigment dispersing agent and optionally organic solvent are mixed in any order.
  • the pigment will have a particle size of about 0.1 to 10 microns and the pigment dispersion 0 will contain a pigment to resin weight ratio in the range of from about 0.01 to 10:1.
  • the pigment can be an inorganic or organic compound which is substantially insoluble in the medium in which it is incorporated which is capable of comminution into a finely divided form.
  • suitable pigments include iron oxide, lead oxide, strontium chro ate, carbon black, coal dust, titanium dioxide, talc, barium sulfate, as well as the color pigments such as cadmium yellow, cadmium red, chromium yellow, phthalocyanine blue, toluidine red, and the quinacridone pigments.
  • organic solvents which may be used with the dispersing agents include aromatic hydrocarbons such as toluene and xylene; ketones such as methyl ethyl ketone and methyl isobutyl ketone; esters such as butyl acetate, 2-ethoxyethyl acetate and 2-butoxyethyl acetate; and glycol ethers such as propylene glycol 5 monomethyl ether.
  • aromatic hydrocarbons such as toluene and xylene
  • ketones such as methyl ethyl ketone and methyl isobutyl ketone
  • esters such as butyl acetate, 2-ethoxyethyl acetate and 2-butoxyethyl acetate
  • glycol ethers such as propylene glycol 5 monomethyl ether.
  • the pigment dispersing agents of the present invention can also be used to disperse pigment by a flushing mechanism wherein the dispersing agent is used to displace water in an aqueous pigment press cake and to intimately disperse the pigment in the dispersing agent by mixing the dispersing agent with the press cake under high shear conditions such as with a Sigma Blade mixer.
  • the resulting pigment dispersion will contain a pigment to resin weight ratio in the range of from about 0.01 to 10:1 depending somewhat on the pigment used and its surface area.
  • the pigment dispersions of the present invention are particularly useful in pigmented, acid catalyzable coating compositions, for example, coating compositions comprising as the principal film-forming resin an active hydrogen group-containing material and an aminoplast curing agent.
  • active hydrogen refers to hydrogens which, because of their position in the polymer molecule, display reactivity with the aminoplast.
  • active hydrogens include hydrogen atoms attached to oxygen and specific examples include hydroxyl and carboxylic acid, which are the most preferred.
  • suitable active hydrogen-containing polymers are acrylic polymers containing hydroxyl groups, and polyester polyols including hydroxyl group-containing alkyds.
  • polyurethane polyols can be used. Typically, these polymers will have hydroxyl values of from about 20 to 200 (on a solids basis).
  • Aminoplast curing agents are aldehyde condensation products of amines or amides with aldehydes.
  • Suitable amines or amides are melamine, benzoguanamine and urea.
  • the aldehyde employed is formaldehyde, although products can be made from other aldehydes such as acetaldehyde and furfuryl.
  • the condensation products contain methylol or similar alkylol groups depending upon the particular aldehyde employed.
  • these alkylol groups are etherified by reaction with an alcohol such as one which contains 1 to 4 carbon atoms such as methanol or butanol.
  • Aminoplasts are commercially available from American Cyanamid Company under the trademark CYMEL and from Monsanto Chemical Company under the trademark RESIMINE.
  • compositions cure in an acidic environment and to promote curing, the compositions usually contain an acid catalyst such as an acidic material, for example, an acid phosphate such as phenyl acid phosphate, and a sulfonic acid such as paratoluene sulfonic acid.
  • an acid catalyst such as an acidic material, for example, an acid phosphate such as phenyl acid phosphate, and a sulfonic acid such as paratoluene sulfonic acid.
  • the coating compositions will typically contain from 45 to 80 percent by weight of the active hydrogen-containing polymer, from 20 to 55 percent by weight of the aminoplast curing agent, the percentages by weight being based on total weight of active hydrogen-containing polymer and aminoplast curing agent.
  • the acid catalyst is present in amounts of up to 5 percent by weight and the pigment dispersing agent is present in amounts of 1 to 70 percent by weight; the percentages by weight being based on weight of resin solids in the coating composition.
  • the pigment is typically present in the composition in amounts of about 0.1 to 85 percent by weight based on total solids of the coating composition.
  • the coating compositions will usually contain an organic solvent and/or diluent.
  • solvents jr diluents would include those mentioned above in connection with the preparation of the pigment paste.
  • the solvent would be present in amounts of about 30 to 70 percent by weight based on total weight of the coating composition.
  • the coating composition can additionally contain optional materials well known in the art for protective and decorative coating compositions. Examples would be UV light stabilizers or UV light absorbers in the event that the coating is designed for exterior applications. Examples of other optional coating ingredients would be fillers, plasticizers, reactive diluents, anti-oxidants, flow control agents and other formulating additives. These optional materials generally constitute up to 30 percent by weight of the coating composition based on total weight of resin solids in the coating composition.
  • the following examples are illustrative of the invention. All percentages are on a weight basis unless otherwise indicated. All acid values and hydroxyl values are on a solids basis unless otherwise indicated.
  • the Examples show the preparation of various pigment dispersing agents and pigment dispersions in accordance with the practice of the invention and the formulation of coating compositions with the pigment dispersions.
  • a pigment dispersion was prepared with an amide-modified polyester polyol as generally taught in U.S. 4,123,422, formulated into a paint and its color strength compared to a paint obtained using the pigment dispersions of the present invention.
  • a pigment dispersion was prepared with a pigment dispersing agent as generally described in U.S. 4,735,984 and formulated into an acid catalyzable paint and the cure response of the paint compared to a paint obtained using the pigment dispersion of the present invention.
  • Example I A flask was charged with 128 grams (g) water, 1157 g neopentyl glycol, 1022 g hydroxypivalyl hydroxypivalate, 510 g trimethylolpropane, 480 g adipic acid, 2160 g isophthalic acid and 9.4 g dibutyltin oxide. A nitrogen blanket was maintained on the mixture which was heated to 210°C. and held at this temperature until the acid value was reduced to 11-15 units. The mixture was then cooled to 150°C. and 65 g xylene was added, followed by 1221 g of caprolactone over 1 hour. The resulting mixture was held at 150°C. until a constant viscosity was reached.
  • Example III A flask was charged with 5452 g of trimethylpentanediol, 1481 g adipic acid, 2063 g isophthalic acid and 3.2 g of dibutyltin oxide. A nitrogen blanket was maintained and the mixture was heated to 205°C. and held at this temperature until the acid value was reduced to 8-10 units. The mixture was cooled to 150°C. and 476 g xylene, 49.5 g aminoethylethanolamine and 3.6 g of butylstannoic acid added. The reaction was held at 150°C. with 9 g of water being removed by azeotropic distillation. After dilution with xylene, the final properties were:
  • Example IV shows the preparation of pigment dispersions using the pigment dispersing agents of Examples I and II and the formulation of paints from the resulting pigment dispersions.
  • Example II To 128 g of the pigment dispersing agent of Example I was added 80 g of 2-butoxyethyl acetate. To this solution was added with agitation 57 g of Ti0 2 , 1.5 g carbon black, 18 g iron oxide, 7 g of strontium chromate pigment and 343 g of barytes. This composition was then ground on a sand mill to an 8.0 hegman. To form the final paint, 652 g of the above pigment dispersion was let down with the following mixture:
  • CYMEL 1158 butylated melamine/formaldehyde condensate from American Cyanamid
  • BEETLE 80 butylated urea formaldehyde resin from American Cyanamid
  • Example V The pigment dispersing agent of Example II was formulated into a paint as follows: To 154 g of the pigment dispersing agent was added 36 g of isobutyl acetate and 36 g of monomethyl ether propylene glycol acetate. To this solution was added with agitation
  • the final paint was obtained by letting down 100 g of the above pigment dispersion with
  • CYMEL 1130 (methylated, butylated melamine/ formaldehyde from American Cyanamid) 19.5
  • Comparative Example VI For the purpose of comparison, a paint was prepared using as the pigment dispersing agent the amide-modified polyester generally described in U.S. 4,123,422.
  • a flask was charged with 27 g water, 251 g neopentyl glycol, 5 165 g trimethylolpropane, 249 g sebacic acid, 307 g isophthalic acid and 0.35 g butylstannoic acid.
  • a nitrogen blanket was maintained and the mixture was heated to 220°C. and held at this temperature until the acid value was reduced to 6-10 units.
  • the solution was cooled to 50°C. and 251 g of propylene glycol monomethyl ether was then added, 0 followed by 4 g of tetraethylpentamine.
  • the following example shows the preparation of a pigment dispersing agent and the use of the dispersing agent to form a pigment dispersion by a flushing technique.
  • the pigment dispersing agent was prepared as follows: A flask was charged with 2351 g of dimer fatty acid (EMP0L 1008 from Henkel Corp.), 256 g trimethylolpropane, 661 g neopentyl glycol, 697 g cyclohexanedimethanol, 0.8 g butylstannoic acid and 2 g triphenylphosphite. A nitrogen blanket was maintained and the mixture was heated to 180°C. and held at this temperature until the acid value was reduced to 7-10 units. The mixture was cooled to 150°C.
  • EMP0L 1008 dimer fatty acid
  • 661 g neopentyl glycol 697 g cyclohexanedimethanol
  • 0.8 g butylstannoic acid 0.8 g butylstannoic
  • the pigment dispersing agent was formulated into a pigment dispersion by flushing as follows: To 300 g of a 32 percent solids quinacridone magenta press cake (Sun Chemical) was added with agitation in a double Sigma Blade mixer 136 g of the pigment dispersing agent. After mixing for about 10 minutes, another 240 g of press cake was added, followed by mixing for about 10 minutes and the addition of 80 g of the pigment dispersing agent. Mixing was continued for about 5 minutes followed by the addition of two 90 g aliquots of press cake. Agitation was continued for about an additional 10 minutes to remove the water and intimately disperse the pigment throughout the dispersing agent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne des agents dispersants de pigments comprenant le produit réactionnel d'un polyester possédant deux groupes acides hydroxyle et carboxylique contenant de 0,02 à 0,4 millimoles d'amine totale par gramme de polyester, ladite amine se trouvant dans la formule (I) dans laquelle Ra représente alkylène contenant de 2 à 6 atomes de carbone et Rb représente alkyle à substitution hydroxy dans lequel le groupe alkyle contient de 2 à 12 atomes de carbone; le pourcentage en poids étant basé sur le poids total de polyester et d'amine. L'agent dispersant de pigments possède d'excellentes propriétés de dispersion et une résistance des couleurs renforcée, et améliore l'écoulement et le nivellement du revêtement pigmenté. L'agent dispersant est notamment utile dans les compositions de revêtement pigmenté pouvant être catalysées par acide comprenant, comme principale résine filmogène, un matériau contenant un groupe hydrogène actif et un agent de durcissement d'aminoplaste. Les agents dispersants de pigments, bien que contenant des groupes amine, n'affectent pas le durcissement de ces compositions filmogènes comme pourraient le faire d'autres agents dispersants contenant des groupes amine, et grâce à la présence de groupes hydroxyle, les agents dispersants de pigments réagissent rapidement pour donner le film durci.
PCT/US1992/005353 1991-07-16 1992-06-26 Agents dispersants de pigments polyester modifies par une amine Ceased WO1993002131A1 (fr)

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US731,846 1991-07-16

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0718381A3 (fr) * 1994-12-21 1997-10-01 Basf Corp Dispersants de pigment à fonctionnalité amine primaire pout utilisation dans les compositions d'électrorevêtement cathodique
EP0879860A3 (fr) * 1997-05-24 1999-02-10 Byk-Chemie GmbH Agent dispersant pour pigments ou charges à base de polyacrylates
EP1364701A1 (fr) * 2002-05-21 2003-11-26 Akzo Nobel N.V. Résine ou groupe hydrocarbyle modifié par des amides
US7276555B2 (en) 2002-05-21 2007-10-02 Hexion Specialty Chemicals, Inc. Amide-modified resin or hydrocarbyl moiety for dispersing a pigment
EP2528728B1 (fr) 2010-01-26 2019-12-18 SIG Technology AG Processus de production d'un récipient à partir d'un composite plan doté d'une couche intérieure par pliage à chaud
WO2020212410A1 (fr) * 2019-04-18 2020-10-22 Basf Se Dispersants d'amines
CN114223075A (zh) * 2019-08-15 2022-03-22 禾大国际股份公开有限公司 分散剂

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882088A (en) * 1968-11-18 1975-05-06 Du Pont Polyesters bearing polyethylenimine terminal groups
US4123422A (en) * 1977-11-25 1978-10-31 Ppg Industries, Inc. Amide modified saturated polyester polyols and method of making
US4224212A (en) * 1977-07-15 1980-09-23 Imperial Chemical Industries Limited Dispersing agents, dispersions containing these agents and paints and inks made from the dispersions
US4735984A (en) * 1984-12-25 1988-04-05 Nippon Paint Co., Ltd. Composition containing dispersed pigment and preparation method thereof
US5000792A (en) * 1988-06-09 1991-03-19 501 Sakata Inkusu Kabushikikaisha Pigment dispersing agent and offset printing ink composition employing the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3882088A (en) * 1968-11-18 1975-05-06 Du Pont Polyesters bearing polyethylenimine terminal groups
US4224212A (en) * 1977-07-15 1980-09-23 Imperial Chemical Industries Limited Dispersing agents, dispersions containing these agents and paints and inks made from the dispersions
US4123422A (en) * 1977-11-25 1978-10-31 Ppg Industries, Inc. Amide modified saturated polyester polyols and method of making
US4735984A (en) * 1984-12-25 1988-04-05 Nippon Paint Co., Ltd. Composition containing dispersed pigment and preparation method thereof
US5000792A (en) * 1988-06-09 1991-03-19 501 Sakata Inkusu Kabushikikaisha Pigment dispersing agent and offset printing ink composition employing the same

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0718381A3 (fr) * 1994-12-21 1997-10-01 Basf Corp Dispersants de pigment à fonctionnalité amine primaire pout utilisation dans les compositions d'électrorevêtement cathodique
EP0879860A3 (fr) * 1997-05-24 1999-02-10 Byk-Chemie GmbH Agent dispersant pour pigments ou charges à base de polyacrylates
US6596816B1 (en) 1997-05-24 2003-07-22 Byk-Chemie Gmbh Dispersing agents for pigments or extenders based on acrylic acid alkyl ester polymers
US7432329B2 (en) 1997-05-24 2008-10-07 Byk-Chemie Gmbh Dispersing agents for pigments or extenders based on acrylic acid alkyl ester polymers
EP1364701A1 (fr) * 2002-05-21 2003-11-26 Akzo Nobel N.V. Résine ou groupe hydrocarbyle modifié par des amides
US7276555B2 (en) 2002-05-21 2007-10-02 Hexion Specialty Chemicals, Inc. Amide-modified resin or hydrocarbyl moiety for dispersing a pigment
EP2528728B1 (fr) 2010-01-26 2019-12-18 SIG Technology AG Processus de production d'un récipient à partir d'un composite plan doté d'une couche intérieure par pliage à chaud
WO2020212410A1 (fr) * 2019-04-18 2020-10-22 Basf Se Dispersants d'amines
CN113692431A (zh) * 2019-04-18 2021-11-23 巴斯夫欧洲公司 胺分散剂
US20220220324A1 (en) * 2019-04-18 2022-07-14 Basf Se Amine dispersants
US12516202B2 (en) * 2019-04-18 2026-01-06 Basf Se Amine dispersants
CN114223075A (zh) * 2019-08-15 2022-03-22 禾大国际股份公开有限公司 分散剂
CN114223075B (zh) * 2019-08-15 2024-06-04 禾大国际股份公开有限公司 分散剂
US12278372B2 (en) 2019-08-15 2025-04-15 Croda International Plc Dispersant

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