CN101691424B - Amide-containing polymer and application thereof - Google Patents
Amide-containing polymer and application thereof Download PDFInfo
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- CN101691424B CN101691424B CN200910153218.XA CN200910153218A CN101691424B CN 101691424 B CN101691424 B CN 101691424B CN 200910153218 A CN200910153218 A CN 200910153218A CN 101691424 B CN101691424 B CN 101691424B
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Abstract
The invention provides an amide-containing polymer, which is polymerized by monomer with reactive amino-group or imino group and monomer with carboxyl group or carboxyl derivatives. The prepared polymer is once more polymerized with one or more monomers of alpha, beta-unsaturated carbonyl compounds, aliphatic acid and derivatives thereof or epoxide; and the prepared polymer is used as pigment, powder, fiber and other dispersant and dispersion stabilizer in a urethane resin system, an acrylic resin system, an alkyd resin system and a melamine resin system.
Description
Technical field
The present invention relates to a kind of synthetic polymer, relate in particular to a kind of amide-containing polymer, and be used for dispersion agent and dispersion stabilizer in pigment, powder and fiber etc.
Background technology
For pigment, pressed powder or fiber are distributed in fluid equably, generally need strong mechanical shearing to stir.After scatter operation, because dispersed powder material granularity is little, the surface can be large, shows strong agglomeration, causes the phenomenons such as system viscosity increase and mobility reduction, causes continuing when serious using.Just address this problem and to add dispersion agent in the production process of product, it can not only make dispersing technology oversimplify, can also change the physical condition on particulate matter surface, make fluid keep satisfactory stability in storage and transportation process, prevent from using the generation of front flocculation and deposited phenomenon.
At present, many materials all are used as the dispersion agent of pigment and filler, and many companies have applied for a large amount of patents in this field.The amine, the amides dispersion agent that are suitable as the dispersion agent of pigment, powder or fiber and/or dispersion stabilizer are too numerous to enumerate especially.Used the amine based polymer based on the amide containing functional group of polyamines and polylactone in EP158406, EP208041 and EP0713894, GB0009798 also discloses with side chain aliphatics acids or alcohols and hydroxycarboxylic acid or lactone reaction as solvent chain, the dispersion agent that contains polyamines and amide structure take polyamines as anchorage.EP0154678 and EP0438836 disclose the dispersion agent based on the amide containing of polyisocyanates.DE102004022753 and DE102006012999 disclose alkalescence or the neutral dispersion agent based on the amide containing structure of urea diketone.EP0311157 has described the amine official energy dispersion agent based on acrylate, is used for disperseing organic and mineral dye.These dispersion agents are used as dispersion and the stablizers of powder in fluid such as pigment and printing ink mostly.
The disclosed dispersion agent of described these patents is often considered its suitability widely when exploitation, require it to be applicable to most pigment and filler in the resin system that major part is commonly used.Like this, just inevitably cause the complicacy of its technique and raw material relatively costly, and it is poor to exist the specific pigment Selective adsorption in use, by the polar solvent in system or be present in system other polar groups with absorption anchorage cement out from particle surface, cause invalid dispersion, finally make system again flocculate and reunite.
Therefore, for specific system with specifically be dispersed material, still need develop dispersion, the stablizer of the simple and raw material cheapness of specific dispersion agent, particularly production technique.
Summary of the invention
The purpose of this invention is to provide a kind of amide-containing polymer, formed by the monomer with reactive behavior amino or imino-and the monomer polymerization with carboxyl or carboxy derivatives.Resulting polymers again with α, one or more monomer repolymerization of beta-unsaturated carbonyl compound, lipid acid and derivative thereof or epoxide, the polymkeric substance that obtains are used for dispersion agent and the dispersion stabilizer of pigment, powder and fiber etc. in urethane resin system, acrylic resin system, Synolac system and melamine resin system.
Amide-containing polymer of the present invention is polymerized by monomer A and monomers B.
Monomer A is as shown in structural formula I:
Wherein, Y is the aliphatic amide group with amino or imino-; R is selected from greater than the alkyl of 2 carbon atoms, greater than the cycloalkyl of 3 carbon atoms and the aryl of alkyl replacement, and the dicarbapentaborane group of polyoxyethylene group and/or polyester group; N is the integer of 0-50.
Monomers B is as shown in structural formula II:
X-R
1-X (II)
Wherein, X is carboxyl or derivatives thereof (as: amide group, acid halide group, ester group or cyano group); R
1Aryl and/or the aryl that the alkyl, cycloalkyl, the alkyl that contain the above direct-connected or side chain of 6 carbon atoms replaces, R
1Can also be for the weight in average molecular weight greater than the polyoxyethylene thiazolinyl that contains alkoxyl group of 200Da and/or contain the polyester based of alkyl.
X group in amino in monomer A of the present invention or imino-Y and described monomers B reacts the polymkeric substance that obtains phosphinylidyne-containing amine group.The polymkeric substance of the phosphinylidyne-containing amine group that obtains and one or more in monomer C, D and/or E are further reacted, fully react with amino on monomer A or imino-, obtain can stably stored dispersion stabilizer.
Monomer C is as shown in structural formula II I:
Wherein, work as X
1During for oxygen, R
4There is not R
2Be C
1-C
22The straight or branched alkyl; Work as X
1During for nitrogen, R
2And R
4Be independently selected from hydrogen or C
1-C
22The straight or branched alkyl.R
3Be independently selected from methyl or hydrogen.In the polymkeric substance repolymerization process that obtains with monomer A and B reaction, preferably with the monomer C of H-H reaction on the mode of Michael addition and amino or imino-.
Monomer D is as shown in structural formula IV:
R
5-X
2 (IV)
Wherein, X
2Can be carboxyl or derivatives thereof (as: amide group, acid halide group, ester group or cyano group), R
5Be C
1-C
22The straight or branched alkyl.Monomer D can pass through X
2In the polymkeric substance that group and monomer A and B reaction obtain, unreacted amino or imino-react and introduce, also can be by introducing with the mode of amino or imino-salify.
Monomer E is as shown in structural formula V:
R wherein
6Can be hydrogen, can be also halogen atom, or be oxygen containing ether residue.In the polymkeric substance that monomer E generally obtains by epoxide group and monomer A and B reaction, unreacted amino or imino-reaction are introduced.
The polymkeric substance of the phosphinylidyne-containing amine group that described monomer A and monomers B make, then with monomer C, D and/or E in one or more reactions after prepared polymkeric substance of the present invention to organic and/or inorganic powder or fiber in urethane resin system, acrylic resin system, Synolac system and melamine resin system good dispersiveness and stability in storage.
In the present invention, monomer A can be by polycarboxylic acid, preferred di-carboxylic acid, or derivatives thereof, as: di-carboxylic acid acid anhydrides, binary carboxylic acid halides and binary acid amides etc., obtain with the polyamine reaction, wherein the mol ratio of polyamine and di-carboxylic acid and/or its derivative is 2: 1-20: 19, preferred 2: 1-8: 7.In the present invention, monomer A can be also only polyamines.
The polycarboxylic acid and the derivative thereof that form monomer A of the present invention, aliphatics, cyclic aliphatic and/or aromatic linearity or the branching of preferred 2-40 carbon atom, saturated or undersaturated di-carboxylic acid and derivative (comprising di-carboxylic acid acid anhydrides, binary carboxylic acid halides and/or binary acid amides etc.) thereof.These di-carboxylic acid are as oxalic acid, propanedioic acid, succsinic acid, pentanedioic acid, hexanodioic acid, pimelic acid, suberic acid, sebacic acid, undecane diacid, dodecanedioic acid, Thapsic acid, octadecane diacid, docosandioic acid, dimeracid, toxilic acid and acid anhydride thereof, FUMARIC ACID TECH GRADE and terephthalic acid etc.Described carboxylic acid can use separately also can mix use, and described acid can be before reacting to form monomer A of the present invention with polyamines, convert in advance the carboxylic acid derivative that is easy to the reaction of the polyamines of formation monomer A of the present invention to, as: acid anhydrides, acid amides, carboxylic acid halides, ester and nitrile etc.
Form the molecular weight of the carboxy blocking that the polycarboxylic acid of monomer A of the present invention and derivative thereof also can obtain by diprotic acid or derivatives thereof (acid anhydride, binary carboxylic acid halides and/or the binary acid amides etc. that comprise di-carboxylic acid) and polyvalent alcohol (preferred dibasic alcohol) reaction less than 5, the petchem of 000Da.Described diprotic acid can be oxalic acid, propanedioic acid, succsinic acid, pentanedioic acid, hexanodioic acid, pimelic acid, suberic acid, sebacic acid, undecane diacid, dodecanedioic acid, Thapsic acid, octadecane diacid, docosandioic acid, dimeracid, toxilic acid and acid anhydride thereof, FUMARIC ACID TECH GRADE, terephthalic acid etc., described polyvalent alcohol can be ethylene glycol, glycerol, propylene glycol, butyleneglycol, decanediol etc., can be also polyether glycol, polyester glycol and/or the polyacrylate diol with 250-5000 molecular weight, described glycol can use separately also can mix use.
Form monomer A polyamine of the present invention and comprise the binary aliphatic primary amine, as: quadrol, 1,2 and 1,3-propylene diamine, Putriscine, 1,5-pentamethylene diamine, neopentane diamines, 1,6-hexanediamine, 1,8-octamethylenediamine, 1, the straight-chain fat diamines such as 12-dodecane diamines; The cycloaliphatic such as cyclohexanediamine, isophorone diamine diamines.Preferred quadrol, propylene diamine, the low-carbon (LC) aliphatic diamines such as butanediamine of using.
The polyamine that forms monomer A of the present invention also comprises the fatty amine with at least three uncles and/or the second month in a season and/or tertiary amine groups.Preferred linear aliphatic family polyamines wherein, as diethylenetriamine (DETA), triethylene tetramine (TETA), tetraethylene pentamine (TEPA), five ethene hexamines, six ethene seven amine, with and higher homologue, as general formula
N 〉=5 wherein.Also can for
The type diamines, wherein R is independently selected from alkyl or alkoxyl group, as: N, N '-two (3-aminocarbonyl propyl) methylamine.
Monomers B of the present invention preferably has and is the aliphatics of 2-40 carbon atom, cyclic aliphatic and/or aromatic linearity or branching, saturated or undersaturated di-carboxylic acid and derivative (acid anhydride, binary carboxylic acid halides and/or the binary acid amides etc. that comprise di-carboxylic acid) thereof, as: oxalic acid, propanedioic acid, succsinic acid, pentanedioic acid, hexanodioic acid, pimelic acid, suberic acid, sebacic acid, undecane diacid, dodecanedioic acid, Thapsic acid, octadecane diacid, docosandioic acid, dimeracid, toxilic acid and acid anhydride thereof, FUMARIC ACID TECH GRADE and terephthalic acid etc.described carboxylic acid can use separately also can mix use, and described acid can be before reacting to form polymkeric substance of the present invention with polyamines, convert in advance the carboxylic acid derivative that is easy to the reaction of the polyamines of formation monomer A of the present invention to, acid anhydrides for example, acid amides, carboxylic acid halides, ester, nitrile etc., example is the oxalic acid diacid chloride, malonyl chloride, glutaryl chlorine, Adipoyl Chloride, pimeloyl chloride, suberoyl chlorine, sebacoyl chloride, the undecane diacid chloride, the dodecane diacid chloride, the n-Hexadecane diacid chloride, the octadecane diacid chloride, the docosane diacid chloride, dimeracid diacid chloride and p-phthaloyl chloride etc.The polycarboxylic acid of monomers B of the present invention and derivative thereof can be also to have weight in average molecular weight 250-5, the polyether diacids of the carboxyl of 000Da and derivative end-blocking thereof, polyester diacid and/or polyacrylic ester diacid, described diacid can use separately also can mix use.
Monomer C of the present invention is α, beta-unsaturated carbonyl compound, as: α, beta-unsaturated carboxylic acid fat and α, beta-unsaturated acyl amine etc.When synthetic dispersion stabilizer of the present invention, the monomer C that preferably introduces in the mode of Michael addition.The advantage of Michael addition is when consuming active amine, keep the amine value constant, so both can reach compound of the present invention and can firmly be adsorbed onto material surface, can keep again compound stability of the present invention good, can standing storage, and can variable color, rotten purpose.Monomer C of the present invention comprise vinylformic acid and (or) methyl acrylic ester, as: (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) propyl acrylate, (methyl) butyl acrylate, (methyl) Ethyl acrylate, (methyl) vinylformic acid laurate and (methyl) stearyl acrylate acid esters etc., and (methyl) esters of acrylic acid of hydroxyl official energy; Propylene and (or) the methacryloyl amine, as N, N '-dimethyl (methyl) acrylamide, N, N '-diethyl (methyl) acrylamide and N-isobutyl-(methyl) acrylamide etc.; Propylene and/or methacrylonitrile; The α that other are fit to, beta-unsaturated carbonyl compound comprises toxilic acid, methylene-succinic acid and derivative thereof, as: maleic anhydride and maleimide etc.
Monomer D of the present invention is a kind of full and/or unsaturated monocarboxylic acid or derivatives thereof (comprising carboxylic acid halides, acid amides, ester, nitrile etc.), and can contain other functional groups in monomer D, as: hydroxyl and amido etc.these monomers comprise the long chain fatty acid that contains 2-40 carbon atom, as: acetic acid, propionic acid, butyric acid, isopropylformic acid, valeric acid, isovaleric acid, caproic acid, enanthic acid, sad, n-nonanoic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, tetradecanoic acid, pentadecylic acid, hexadecanoic acid, margaric acid, stearic acid, nondecylic acid, arachic acid, docosoic acid, Lignoceric acid, cerinic acid, triacontanoic acid, lauroleic acid, oleic acid, linolic acid, erucic acid, Zoomeric acid, linolenic acid, arachidonic acid, alpha-eleostearic acid, α-therapic acid, coco-nut oil fatty acid, sweet oil lipid acid, palm oil fatty acid, cottonseed oil fatty acid, peanut oil fatty acid, soy(a)-bean oil fatty acid, sunflower oil lipid acid, rape oil fatty acid, tall oil fatty acid and tallow fatty acids etc., the aromatic series monocarboxylic acid, as: phenylformic acid, toluylic acid and p-methylbenzoic acid etc., the monocarboxylic acid that contains other functional groups, as: oxyacetic acid, hydroxy-propionic acid, 12-oxystearic acid and ricinolic acid lipid acid etc.Described monocarboxylic acid can use separately also can mix use.Monomer D can be by introducing with the mode of active amido reaction formation amide group, also can introducing in the mode of direct salify.
Monomer E of the present invention can be propylene oxide, epoxy chloropropane and/or saturated or undersaturated fat base, alicyclic radical and/or aromatic base glycidyl ether, as: methyl glycidyl ether, ethyl ether, butylglycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether and glycidyl allyl ether etc.
Of the present invention by monomer A and the prepared polymkeric substance of monomers B can be only and monomer C, monomer D or monomer E react separately and obtain of the present invention finally be suitable as organic in urethane resin system, acrylic resin system, Synolac system and melamine resin system and (or) mineral dye, powder or dispersing agent for fibre and dispersion stabilizer, also one or more in monomer C, D and E can be incorporated into together and finally obtain polymkeric substance of the present invention in system.
As is known to those skilled in the art, the synthesis condition that the present invention relates to monomer A is different because of selected raw material, carbonyl moiety raw material as synthon A is carboxylic acid, the temperature of reaction with polyamine is 50-220 ℃, preferred 120-200 ℃ is the corresponding gentleness of reaction conditions of carboxylic acid derivative as the carbonyl moiety raw material of synthon A.Condition by the polymkeric substance of the synthetic amide containing structure of monomer A and monomers B is basic identical with the condition of synthon A, and his condition of reaction of itself and monomer C is 20-150 ℃, preferably 50-120 ℃.The reaction conditions of the polymkeric substance of monomer D and amide containing structure of the present invention is 50-220 ℃, preferred 120-200 ℃.The reaction conditions of the polymkeric substance of monomer E and amide containing structure of the present invention is 20-150 ℃, preferred 50-120 ℃.
The technology type of the preparation of polymkeric substance of the present invention and existing preparation polymkeric substance seemingly, according to the viscosity of reactant and the solids content requirement of product, before reaction and/or can suitably add afterwards not inert solvent with the reaction of system active substance, these solvents and reactant and product can mix, these high boiling materials, as: the aromatic hydrocarbon substances such as toluene, dimethylbenzene and trimethylbenzene; Ester family and/or cyclic ester family's high boiling substance (boiling point is greater than 100 ℃); Ethers, as: Isosorbide-5-Nitrae-dioxane, tetrahydrofuran (THF), butyl glycol ether etc.; The ester class, as: ethyl acetate, butylacetate, butyrolactone and phthalic ester etc.; Amides, as: DMF and N-Methyl pyrrolidone etc.; Alcohols, as: ethanol, butanols, amylalcohol and isopropylcarbinol etc.Also can use the mixture of described solvent.
Polymkeric substance of the present invention can use according to known dispersion agent operation technique in urethane resin system, acrylic resin system, Synolac system and melamine resin system.Described polymkeric substance can be first and the pigment, powder and/or the blending in of fibers that need to disperse after make and disperse after masterbatch and the mixed dispersion of making of the base-materials such as urethane resin, acrylic resin, Synolac and/or melamine resin, also can be directly with dispersion agent of the present invention with need pigment, solid and/or the fiber of dispersion and binder resin disperses after being mixed together.A kind of preferred mode be first with dispersion stabilizer of the present invention with after binder resin mixes, pigment, powder and/or fiber etc. that needs are disperseed join in base-material and mix.
The consumption of polymkeric substance of the present invention is decided according to the surface properties of the material of need dispersion, as: the surface-area of carbon black disperses the carbon black of equivalent amount need to use than disperseing titanium dioxide polymkeric substance that more the present invention tells in same system greater than titanium dioxide.Dispersion stabilizer of the present invention generally uses with the quantity of the 0.1wt%-100wt% that is dispersed material.
Dispersion stabilizer of the present invention is adapted in urethane resin system, acrylic resin system, Synolac system and melamine resin system, the organic and inorganic pigment of various routines, powder and/or fiber etc. being formed dispersion.Mineral dye comprises various metal oxides, as: titanium dioxide, ferric oxide and/or zinc oxide; Carbon black; Various pigment dyestuffs, as: quinacridone, phthalocyanine, perylene, azo pigment and various indanthrone carbazole, as: carbazole violet; Filler comprises silicon-dioxide, diatomite, quartz, silica gel, talcum, kaolin, mica, perlite, feldspar, slate flour, calcium sulfate, barium sulfate, calcium carbonate, calcite, rhombspar, glass, charcoal and various tinsels etc.; Fiber comprises various natural and regenerated fibers, natural fiber has cotton, kapok, flax fiber, hemp, piemarker, mestha, ramie, jute, sisal hemp, abaca, coconut fiber, wool, rabbit, silk, mulberry silk and asbestos, and regenerated fiber comprises, steel fiber, glass fibre, rock fiber slag fibre, viscose fiber, copper ammonia fibre, cellulose acetate fibre, polynosic, cellulose ester fiber, lanara, Zein fibers, soybean fiber, terylene, polyamide fibre, acrylic fibers, polypropylene fibre, spandex, polyvinyl, polyvinyl chloride fibre, aramid fiber and polyethylene etc.
The beneficial effect that the present invention realizes:
Amide-containing polymer of the present invention is formed by the monomer with reactive behavior amino or imino-and the monomer polymerization with carboxyl or carboxy derivatives.Resulting polymers again with α, one or more monomer repolymerization of beta-unsaturated carbonyl compound, lipid acid and derivative thereof or epoxide, the polymkeric substance that obtains are used for dispersion agent and the dispersion stabilizers such as pigment, powder and fiber in urethane resin system, acrylic resin system, Synolac system and melamine resin system.
Embodiment
Below describe technical scheme of the present invention in detail.Only for the explanation concrete grammar, its scale of the method is not subjected to the restriction of embodiment to the embodiment of the present invention.
Embodiment 1
The general step for preparing compound of the present invention (A):
Under protection of inert gas; add polyamines, carboxylic acid or derivatives thereof and solvent in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed; be heated to certain temperature; after reaction certain hour under decompression or normal pressure; tell with water trap and produced moisture, amine or the alcohols pentyl ester of little minute by reaction, cooling stand-by.
Compound (A)
Embodiment 2
Under protection of inert gas; add 0.78 gram propanedioic acid and 50.66 gram dimethylbenzene in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed; take 48.22 grams (A) 1; slowly splash into four-hole boiling flask with dropping funnel, with mixture heating up to 200 ℃, reacted 3 hours; water trap is told the moisture of generation; be cooled to 100 ℃ and add 1.66 gram butyl acrylates, continue reaction 3 hours cooling, discharging.
Embodiment 3
Under protection of inert gas; add 0.95 gram oxalic acid and 69.84 gram dimethylbenzene in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed, take 68.13 grams (A) 2, slowly splash into four-hole boiling flask with dropping funnel; with mixture heating up to 200 ℃; react and add 0.56 gram oleic acid after 3 hours, continue reaction 3 hours, water trap is told the moisture of generation; be cooled to 100 ℃ and add 0.2 gram N; N '-DMAA continues reaction 3 hours cooling, discharging.
Embodiment 4
Under protection of inert gas; add 1.25 gram terephthalic acids and 66.82 gram dimethylbenzene in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed; take 64.81 grams (A) 3; slowly splash into four-hole boiling flask with dropping funnel; with mixture heating up to 200 ℃; react and add 0.56 gram ready denier oil acid after 3 hours; continue reaction 3 hours; water trap is told the moisture of generation; be cooled to 100 ℃ and add 0.2 gram N; N '-DMAA continues reaction 3 hours cooling, discharging.
Embodiment 5
Under protection of inert gas; add 1.3 gram suberic acids and 66.81 gram dimethylbenzene in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed; take 64.81 grams (A) 3; slowly splash into four-hole boiling flask with dropping funnel; with mixture heating up to 200 ℃, react and add 0.7 gram ready denier oil acid after 3 hours, continue reaction 3 hours; water trap is told the moisture of generation, discharging.
Embodiment 6
Under protection of inert gas; add 1.94 gram 3-(carboxymethyl)-2-naphthalene propionic acid and 64.97 gram dimethylbenzene in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed; take 62.33 grams (A) 4; slowly splash into four-hole boiling flask with dropping funnel; with mixture heating up to 200 ℃, react and add 0.7 gram ready denier oil acid after 3 hours, continue reaction 3 hours; water trap is told the moisture of generation, discharging.
Embodiment 7
Under protection of inert gas; add 2.8 gram dimeracids and 67.87 gram dimethylbenzene in the four-hole boiling flask that whipping appts, thermometer, water trap and vacuum unit are housed; take 63.66 grams (A) 5; slowly splash into four-hole boiling flask with dropping funnel; with mixture heating up to 200 ℃, react and add 1.41 gram ready denier oil acids after 3 hours, continue reaction 3 hours; water trap is told the moisture of generation, discharging.
The present invention selects representative carbon black as estimating polymkeric substance of the present invention to the judgment criteria of various materials in urethane resin system, acrylic resin system, Synolac system and melamine resin system dispersiveness and stability in storage, specifically is implemented as follows:
Blank sample 1
The commercial polyurethane resin of 100 gram 50% solid contents is stirred 40min at 80 ℃, add 40 gram DMF, 20 gram MEK and the commercially available carbon black of 8 grams after cooling, stir 2min with 2,000 VELOCITY SHEAR that turn per minute, standby.
Blank sample 2
The commercially available Synolac of 100 gram 50% solid contents is stirred 40min at 80 ℃, add 40 gram DMF, 20 gram MEK and the commercially available carbon black of 8 grams after cooling, stir 2min with 2,000 VELOCITY SHEAR that turn per minute, standby.
Blank sample 3
The commercially available acrylic resin of 100 gram 50% solid contents is stirred 40min at 80 ℃, add 40 gram DMF, 20 gram MEK and the commercially available carbon black of 8 grams after cooling, stir 2min with 2,000 VELOCITY SHEAR that turn per minute, standby.
Embodiment 8
Add 0.1 gram embodiment 2 compounds in the commercial polyurethane resin of 100 gram 50% solid contents, 80 ℃ are stirred 40min, add 40 gram DMF, 20 gram MEK and the commercially available carbon black of 8 grams after cooling, stir 2min with 2,000 VELOCITY SHEAR that turn per minute, standby.
With blank sample 1 resin and embodiment 8 resins on mirror surface release paper, respectively carry out blade coating with 15S scraper the right and left, 120 ℃ of oven dry, the right and left aberration is obvious, the color and luster of embodiment 8 resins is vivid, and blackness is placed after one month without considerable change apparently higher than blank sample 1, relatively blank sample 1 film of embodiment 8 resin films still keeps high blackness, illustrates that polymkeric substance of the present invention has good dispersing property to carbon black in polyurethane system.
Embodiment 9
Add 0.1 gram embodiment 3 compounds in the commercially available Synolac of 100 gram 50% solid contents, 80 ℃ are stirred 40min, add 40 gram DMF, 20 gram MEK and the commercially available carbon black of 8 grams after cooling, stir 2min with 2,000 VELOCITY SHEAR that turn per minute, standby.
With blank sample 2 resins and embodiment 9 resins on mirror surface release paper, respectively carry out blade coating with 15S scraper the right and left, 120 ℃ of oven dry, the right and left aberration is obvious, the color and luster of embodiment 9 resins is vivid, and blackness is placed after one month without considerable change apparently higher than blank sample 2, relatively blank sample 2 films of embodiment 9 resin films still keep high blackness, illustrate that polymkeric substance of the present invention has good dispersing property to carbon black in the Synolac system.
Embodiment 10
Add 0.1 gram embodiment 4 compounds in the commercially available acrylic resin of 100 gram 50% solid contents, 80 ℃ are stirred 40min, add 40 gram DMF, 20 gram MEK and the commercially available carbon black of 8 grams after cooling, stir 2min with 2,000 VELOCITY SHEAR that turn per minute, standby.
With blank sample 3 resins and embodiment 10 resins on mirror surface release paper, respectively carry out blade coating with 15S scraper the right and left, 120 ℃ of oven dry, the right and left aberration is obvious, the color and luster of embodiment 10 resins is vivid, and blackness is placed after one month without considerable change apparently higher than blank sample 3, relatively blank sample 3 films of embodiment 10 resin films still keep high blackness, illustrate that polymkeric substance of the present invention has good dispersing property to carbon black in the acrylic resin system.
Claims (3)
1. a polymkeric substance, be used for urethane resin system, acrylic resin system, Synolac system and melamine resin system as dispersion agent;
Described polymkeric substance is first by after monomer A and monomers B polymerization, then reacts and get with butyl acrylate, N,N-DMAA or ready denier oil acid;
Described monomer A is polyamines, and described polyamines is binary aliphatic primary amine or the fatty amine that has at least three primary amine groups or have at least three secondary amine or have at least three tertiary amine groups;
Described monomers B is the di-carboxylic acid aliphatics of 2-40 carbon atom, aromatic linearity or branching, saturated or undersaturated and derivative thereof, and described diprotic acid derivative is dibasic acid anhydride or binary carboxylic acid halides.
2. polymkeric substance according to claim 1 is characterized in that described polymkeric substance uses with the quantity of the 0.1wt%-100wt% that is dispersed material.
3. polymkeric substance according to claim 1, is characterized in that described polymkeric substance forms dispersion to various organic and inorganic pigment, powder or fiber in described urethane resin system, described acrylic resin system, described Synolac system and described melamine resin system.
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| ES2621604T3 (en) * | 2010-04-26 | 2017-07-04 | Lubrizol Advanced Materials, Inc. | Dispersant composition |
| EP3305840B1 (en) * | 2016-10-05 | 2019-11-06 | Evonik Degussa GmbH | Compatibilizer for universal colorant in solventborne alkyd paints |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158406A1 (en) * | 1984-02-02 | 1985-10-16 | Imperial Chemical Industries Plc | Dispersion of magnetic particles |
| EP0713894A2 (en) * | 1994-11-22 | 1996-05-29 | Daicel Chemical Industries, Ltd. | A polylactone having amino groups, a process for the preparation thereof, a compound having amino group, a composition for coatings, a composition for printing inks |
| US6284867B1 (en) * | 1997-09-23 | 2001-09-04 | Mbt Holding Ag | Highly efficient cement dispersants |
-
2009
- 2009-10-29 CN CN200910153218.XA patent/CN101691424B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158406A1 (en) * | 1984-02-02 | 1985-10-16 | Imperial Chemical Industries Plc | Dispersion of magnetic particles |
| EP0713894A2 (en) * | 1994-11-22 | 1996-05-29 | Daicel Chemical Industries, Ltd. | A polylactone having amino groups, a process for the preparation thereof, a compound having amino group, a composition for coatings, a composition for printing inks |
| US6284867B1 (en) * | 1997-09-23 | 2001-09-04 | Mbt Holding Ag | Highly efficient cement dispersants |
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| CN101691424A (en) | 2010-04-07 |
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