CN104403100A - Method for preparing water-based polyamide thixotropic anti-settling agent - Google Patents
Method for preparing water-based polyamide thixotropic anti-settling agent Download PDFInfo
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- CN104403100A CN104403100A CN201410774199.3A CN201410774199A CN104403100A CN 104403100 A CN104403100 A CN 104403100A CN 201410774199 A CN201410774199 A CN 201410774199A CN 104403100 A CN104403100 A CN 104403100A
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Abstract
The invention relates to the field of chemical ink coatings, in particular to a method for preparing a water-based polyamide thixotropic anti-settling agent. The method comprises the following steps: 1, co-polymerizing binary acid, an organic acid with hydroxyl and diamine to obtain a co-polymerized polyamide prepolymer with hydroxyl; 2, performing acidation in the way that the co-polymerized polyamide prepolymer with hydroxyl and an acidifier are subject to binary copolymerization reaction to obtain polyamide with carboxyl; 3, realizing neutralization of polyamide with carboxyl and alkali to obtain the water-based polyamide thixotropic anti-settling agent. The method is simple and is low in raw material cost; the prepared water-based polyamide is simple in process and good in product quality; the anti-sagging and leveling properties of a film when mainly used as an anti-settling agent of a coating can be better balanced; the coating system is endowed with higher thixotropy; favorable thickening and anti-settling functions are achieved; fillers and pigments in the coating are effectively prevented from sedimentation; the method can be extensively applied to the water-based system coating and has a wide application range.
Description
Technical field
The present invention relates to chemical industry printing ink paint field, be specifically related to a kind of preparation method of aqueous polyamide thixotroping anti-settling agent.
Background technology
In prior art, in order to the stream controlling liquid system becomes, usually use such as silicon-dioxide, hydrogenated castor oil, organically-modified wilkinite and polyamide wax.In polymeric amide and polymeric amide fat field, there is a large amount of patent, such as DE 69523221, EP 0239419, US 5510452l etc.Also just like described in EP 0509202 and DE 69704691, the wilkinite of modification and the combination of polymeric amide is also used.
Above technology is powder or slurry normally, but powder or slurry must utilize solvent and apply shearing force and convert it into work in-process, or utilizes special temperature to control to be introduced into liquid coating system.Except non-required difficult control of temperature, complex process, temperature, once too high or too low obtained finished product coating system all can produce particle, causes coating products defect.Thus make to occur in the Clear paint obtained delustring and opaque, and these coating can not be used for water-based system, and range of application is limited to.
Summary of the invention
The object of the invention is for above-mentioned deficiency of the prior art, a kind of preparation method of aqueous polyamide thixotroping anti-settling agent is provided, have technique simple, good product quality, the anti-settling agent mainly as coating uses, sag resistance and the levelling property of film can be balanced preferably, the thixotropic property that lance coating system is higher can be composed, and there is excellent thickening, anti-settling effect, effectively can prevent the precipitation of face in coating, filler, can be widely used in aqueous systems coating, applied widely.
Object of the present invention is achieved through the following technical solutions.
A preparation method for aqueous polyamide thixotroping anti-settling agent, comprises following procedure of processing: the first step, first by diprotic acid, hydroxyl organic acid and diamine copolymerization, obtain the copolyamide prepolymer of hydroxyl;
Second step, acidifying: the copolyamide prepolymer of hydroxyl and souring agent are carried out binary copolymerization reaction, obtains carboxylic polymeric amide, described souring agent is diprotic acid or acid anhydrides;
3rd step, carboxylic polymeric amide and alkali to be neutralized, namely obtain aqueous polyamide thixotroping anti-settling agent.Further, carboxylic polymeric amide obtained for step 2 is added the neutralization of a certain amount of alkali, when product can reaction soluble in water complete.Particularly, the mol ratio of carboxylic polymeric amide and alkali is 1:0.5 ~ 1.
Wherein, the described the first step, be specially: dried diamine, diprotic acid and hydroxyl organic acid are added in there-necked flask, diamine and hydroxyl organic acid mol ratio are 0.5-0.96:1, and diprotic acid and hydroxyl organic acid mol ratio are 0.1-5:1, then in flask, add a certain amount of solvent and catalyzer, pre-polymerization 1-3h at 70-160 DEG C, obtain the Polvamide prepolymer of hydroxyl, then vacuum sloughs water, the copolyamide prepolymer of obtained hydroxyl; Described solvent is DMF or NMP, and described catalyzer is pyridine, triphenyl phosphite, imidazoles or phenyl Hypophosporous Acid, 50.
Wherein, the addition of described solvent is the 10-50% of the copolyamide prepolymer total mass of hydroxyl, and the addition of described catalyzer is the 3-6 ‰ of the copolyamide prepolymer total mass of hydroxyl.
Wherein, described second step, is specially: the reaction system of the copolyamide prepolymer of the hydroxyl the first step obtained is cooled to 50 DEG C, adds souring agent and acidifying catalyzer, when souring agent is acid anhydrides, reaction system is warming up to 60-90 DEG C of reaction 2-4h; When souring agent is diprotic acid, then reaction system is warming up to 180 DEG C and carries out reaction dehydration, the reaction times is 3-6h, after sufficient reacting, is cooled to room temperature, obtains carboxylic polymeric amide; Described acidifying catalyzer is pyridine, N-picoline, tetrabutyl titanate, triphenyl phosphite or dibutyl tin laurate.
Wherein, in the described the first step, the temperature of copolyreaction is 70-160 DEG C, and the reaction times is 1-3h; In described second step, the reaction pressure 0.1MPa in water smoking, the temperature of reaction of described acidifying is 50-190 DEG C, and the reaction times is 1-6h; In described 3rd step, alkali neutral temperature is 30-50 DEG C, reaction times 1-2h.
Wherein, described acid anhydrides is one or more the mixture in pyromellitic dianhydride, phthalic anhydride and cis-butenedioic anhydride.
Wherein, described diprotic acid is one or more the mixture in hexanodioic acid, terephthalic acid, m-phthalic acid, nonane diacid, sebacic acid, pentanedioic acid, succinic acid.
Wherein, described diamine is one or more the mixture in decamethylene diamine, hexanediamine, quadrol, diethylenetriamine, propylene diamine, heptamethylene diamine, octamethylenediamine, nonamethylene diamine, Ursol D, O-Phenylene Diamine, mphenylenediamine, polyethyleneoxide diamine, butanediamine, pentamethylene diamine.
Wherein, described hydroxyl organic acid is one or more the mixture in oxysuccinic acid, dimethylol propionic acid, ten dihydroxystearic acids, oxyacetic acid, P-hydroxybenzoic acid, citric acid, tartrate.
Wherein, described alkali is potassium hydroxide, sodium hydroxide, triethylene diamine, four ethene triamines, multiethylene polyamine, quadrol, propylene diamine, butanediamine, hexanediamine, thanomin etc. have one or more mixture in the water-soluble substances of similar structures.
Beneficial effect of the present invention:
(1) the invention discloses a kind of preparation method of aqueous polyamide thixotroping anti-settling agent, be by after diprotic acid, hydroxyl organic acid and diamine copolymerization, then carry out acidifying, then neutralize through alkali and obtain product; This preparation method is simple, cheaper starting materials, it is simple that obtained aqueous polyamide has technique, good product quality, anti-settling agent mainly as coating uses, sag resistance and the levelling property of film can be balanced preferably, the thixotropic property that lance coating system is higher can be composed, and there is excellent thickening, anti-settling effect, effectively can prevent the precipitation of face in coating, filler.
(2) polyamide resin is generally formed by diprotic acid and diamine polycondensation, can be divided into solvent-borne type polymeric amide and non-solvent polymeric amide by solvability, because having the groups such as the amido linkage of strong polarity, is being added into coating or pre-activate formation reticulated structure.Current use be solvent-borne type polyamide anti-settling agent, early stage solvent-borne type polymeric amide is dissolved in benzene, dimethylbenzene, but the arene solution smell of this resin is large, contaminate environment, harm workers ' health, limits its further use.The aqueous polyamide thixotroping anti-settling agent that the present invention obtains, is applicable to aqueous solution systems, effectively can reduce volatile organic compounds (VOC) and air noxious pollutant.
(3) the aqueous polyamide thixotroping anti-settling agent that the present invention obtains has environmental advantages such as not firing, nontoxic, pollution-free, particularly in recent years along with the surging of organic solvent price and environmental administration use organic solvent and the strict restriction of waste discharge, aqueous polyamide thixotroping anti-settling agent replaces the important directions that organic solvent type polymeric amide becomes this field development at present.
Embodiment
The invention will be further described with the following Examples.
embodiment 1
Citric acid 20g, hexanodioic acid 80g, decamethylene diamine 62g, ten dihydroxystearic acid 50g are put into vacuum drying oven, drying 12 hours at 60 DEG C.Dried raw material is added in there-necked flask, in flask, add 150mL N monomethyl pyrrolidone as solvent, at 80 DEG C, pre-polymerization is after 1 hour, is warmed up to 110 DEG C, add 12mL phosphorous acid triphen cruel, after reacting 0. 5h, be warmed up to 125 DEG C, react after 2 hours, cooling, add 10. 3g maleic anhydrides and 3g pyridine, stir and reaction 2 hours after being heated to 80 DEG C, obtain acidified aqueous polyamide resin; Add 7g trolamine again to neutralize, obtain product.
embodiment 2
Oxysuccinic acid 80g, m-phthalic acid 60g, hexanediamine 39. 6g, dimethylol propionic acid are put into vacuum drying oven, drying 12 hours at 60 DEG C.Dried raw material is added in there-necked flask, 150mL N monomethyl pyrrolidone is added as solvent in flask, at 70 DEG C, pre-polymerization is after 2 hours, be warmed up to 150 DEG C, add 12mL phosphorous acid triphen extremely, react after 2 hours, cooling, add 52. 1g Tetra hydro Phthalic anhydrides and 3g pyridine, stir and reaction 2 hours after being heated to 80 DEG C, add thanomin 20g i.e. obtaining aqueous polyamide thixotroping anti-settling agent.
embodiment 3
By oxysuccinic acid 15g, hexanodioic acid 60g, 1,7 one heptamethylene diamine 39g, ten dihydroxystearic acid 20g put into vacuum drying oven, drying 12 hours at 60 DEG C.Dried raw material is added in there-necked flask, 150mL N monomethyl pyrrolidone is added as solvent in flask, at 100 DEG C, pre-polymerization is after 1 hour, be warmed up to 150 DEG C, add 12mL phenyl Hypophosporous Acid, 50, react after 2 hours, cooling, add 12g toxilic acid to join and 3g Dimethylamino pyridine, stir and reaction 2 hours after being heated to 60 DEG C, then add potassium hydroxide 5g and namely obtain aqueous polyamide thixotroping anti-settling agent.
embodiment 4
The first step, octamethylenediamine, terephthalic acid and dimethylol propionic acid by dried add in there-necked flask, the mol ratio of octamethylenediamine and dimethylol propionic acid is 0.5:1, the mol ratio of terephthalic acid and dimethylol propionic acid is 0.1:1, then in flask, a certain amount of solvent and catalyzer is added, pre-polymerization 3h at 70 DEG C, then vacuum sloughs water; Described solvent is DMF, and described catalyzer is pyridine.The addition of described solvent is 120ml/mol, and the addition of described catalyzer is 10 ml/mol.
Second step, reaction system in the first step, be cooled to 50 DEG C, add souring agent and acidifying catalyzer, when souring agent is pyromellitic dianhydride, reaction system is warming up to 70 DEG C of reaction 2.5h, after sufficient reacting, is cooled to room temperature; Described acidifying catalyzer is tetrabutyl titanate.
3rd step, carboxylic polymeric amide and sodium hydroxide are neutralized, the mol ratio of carboxylic polymeric amide and alkali is 1:0.5, and alkali neutral temperature is 30 DEG C, reaction times 2h, namely obtains aqueous polyamide thixotroping anti-settling agent.
embodiment 5
The first step, Ursol D, nonane diacid and oxyacetic acid by dried add in there-necked flask, the mol ratio of Ursol D and oxyacetic acid is 0.72:1, the mol ratio of nonane diacid and oxyacetic acid is 2.5:1, then in flask, a certain amount of solvent and catalyzer is added, pre-polymerization 2h at 100 DEG C, then vacuum sloughs water; Described solvent is NMP, and described catalyzer is triphenyl phosphite.The addition of described solvent is 160ml/mol, and the addition of described catalyzer is 15ml/mol.
Second step, reaction system in the first step, be cooled to 50 DEG C, add souring agent and acidifying catalyzer, when souring agent is phthalic anhydride, reaction system is warming up to 80 DEG C of reaction 3h, after sufficient reacting, is cooled to room temperature; Described acidifying catalyzer is triphenyl phosphite.
3rd step, carboxylic polymeric amide and four ethene triamines are neutralized, the mol ratio of carboxylic polymeric amide and alkali is 1:0.8, and alkali neutral temperature is 40 DEG C, reaction times 1.5h, namely obtains aqueous polyamide thixotroping anti-settling agent.
embodiment 6
The first step, diethylenetriamine, sebacic acid and ten dihydroxystearic acids by dried add in there-necked flask, the mol ratio of diethylenetriamine and ten dihydroxystearic acids is 0.96:1, the mol ratio of sebacic acid and ten dihydroxystearic acids is 5:1, then in flask, a certain amount of solvent and catalyzer is added, pre-polymerization 1h at 160 DEG C, then vacuum sloughs water; Described solvent is DMF, and described catalyzer is phenyl Hypophosporous Acid, 50.The addition of described solvent is 135ml/mol, and the addition of described catalyzer is 13ml/mol.
Second step, reaction system in the first step, be cooled to 50 DEG C, add souring agent and acidifying catalyzer, when souring agent is diprotic acid, then reaction system is warming up to 180 DEG C and carries out reaction dehydration, the reaction times is 4h, the reaction pressure 0.1MPa in water smoking, after sufficient reacting, is cooled to room temperature; Described acidifying catalyzer is dibutyl tin laurate.
3rd step, carboxylic polymeric amide and multiethylene polyamine are neutralized, the mol ratio of carboxylic polymeric amide and alkali is 1:1, and alkali neutral temperature is 50 DEG C, reaction times 1h, namely obtains aqueous polyamide thixotroping anti-settling agent.
Finally should be noted that; above embodiment is only in order to illustrate technical scheme of the present invention; but not limiting the scope of the invention; although done to explain to the present invention with reference to preferred embodiment; those of ordinary skill in the art is to be understood that; can modify to technical scheme of the present invention or equivalent replacement, and not depart from essence and the scope of technical solution of the present invention.
Claims (10)
1. a preparation method for aqueous polyamide thixotroping anti-settling agent, is characterized in that: comprise following procedure of processing: the first step, first by diprotic acid, hydroxyl organic acid and diamine copolymerization, obtain the copolyamide prepolymer of hydroxyl;
Second step, acidifying: the copolyamide prepolymer of hydroxyl and souring agent are carried out binary copolymerization reaction, obtains carboxylic polymeric amide, described souring agent is diprotic acid or acid anhydrides;
3rd step, carboxylic polymeric amide and alkali to be neutralized, namely obtain aqueous polyamide thixotroping anti-settling agent.
2. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterized in that: the described the first step, be specially: by dried diamine, diprotic acid and hydroxyl organic acid add in there-necked flask, diamine and hydroxyl organic acid mol ratio are 0.5-0.96:1, diprotic acid and hydroxyl organic acid mol ratio are 0.1-5:1, then in flask, a certain amount of solvent and catalyzer is added, pre-polymerization 1-3h at 70-160 DEG C, obtain the Polvamide prepolymer of hydroxyl, vacuum sloughs water again, the copolyamide prepolymer of obtained hydroxyl, described solvent is DMF or NMP, and described catalyzer is pyridine, triphenyl phosphite, imidazoles or phenyl Hypophosporous Acid, 50.
3. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 2, it is characterized in that: the addition of described solvent is the 10-50% of the copolyamide prepolymer total mass of hydroxyl, the addition of described catalyzer is the 3-6 ‰ of the copolyamide prepolymer total mass of hydroxyl.
4. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterized in that: described second step, be specially: the reaction system of the copolyamide prepolymer of the hydroxyl the first step obtained is cooled to 50 DEG C, add souring agent and acidifying catalyzer, when souring agent is acid anhydrides, reaction system is warming up to 60-90 DEG C of reaction 2-4h; When souring agent is diprotic acid, then reaction system is warming up to 180 DEG C, the reaction times is 3-6h, after sufficient reacting, is cooled to room temperature, obtains carboxylic polymeric amide; Described acidifying catalyzer is pyridine, N-picoline, tetrabutyl titanate, triphenyl phosphite or dibutyl tin laurate.
5. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, is characterized in that: in the described the first step, and the temperature of copolyreaction is 70-160 DEG C, and the reaction times is 1-3h; In described second step, the temperature of reaction of described acidifying is 50-190 DEG C, and the reaction times is 1-6h; In described 3rd step, alkali neutral temperature is 30-50 DEG C, reaction times 1-2h.
6. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, is characterized in that: described acid anhydrides is one or more the mixture in pyromellitic dianhydride, phthalic anhydride and cis-butenedioic anhydride.
7. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, is characterized in that: described diprotic acid is one or more the mixture in hexanodioic acid, terephthalic acid, m-phthalic acid, nonane diacid, sebacic acid, pentanedioic acid, succinic acid.
8. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, is characterized in that: described diamine is one or more the mixture in decamethylene diamine, hexanediamine, quadrol, diethylenetriamine, propylene diamine, heptamethylene diamine, octamethylenediamine, nonamethylene diamine, Ursol D, O-Phenylene Diamine, mphenylenediamine, polyethyleneoxide diamine, butanediamine, pentamethylene diamine.
9. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, is characterized in that: described hydroxyl organic acid is one or more the mixture in oxysuccinic acid, dimethylol propionic acid, ten dihydroxystearic acids, oxyacetic acid, P-hydroxybenzoic acid, citric acid, tartrate.
10. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, is characterized in that: described alkali is one or more the mixture in potassium hydroxide, sodium hydroxide, triethylene diamine, four ethene triamines, multiethylene polyamine, quadrol, propylene diamine, butanediamine, hexanediamine, thanomin.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018010615A1 (en) * | 2016-07-15 | 2018-01-18 | Deuchem (Shanghai) Chemical Co., Ltd. | Novel non-ionic polyamide rheology modifier for aqueous coating |
| CN109735160A (en) * | 2018-12-21 | 2019-05-10 | 浙江丰虹新材料股份有限公司 | A kind of easy distributed aqueous polyamide wax and preparation method and application |
| CN110709480A (en) * | 2017-04-11 | 2020-01-17 | 巴斯夫涂料有限公司 | Coating for producing structured surfaces |
| CN112292427A (en) * | 2018-03-27 | 2021-01-29 | 太阳化学公司 | Water-based inks with renewable materials |
| CN112589318A (en) * | 2020-11-12 | 2021-04-02 | 深圳市晨日科技股份有限公司 | Water-soluble lead-free soldering paste, water-washing solder paste and preparation method thereof |
| US11505649B2 (en) | 2017-09-28 | 2022-11-22 | Dupont Polymers, Inc. | Polymerization process |
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| GB2190388A (en) * | 1986-03-27 | 1987-11-18 | Coates Brothers Plc | Polyamides and thixotropic compositions containing them |
| CN103013216A (en) * | 2011-09-26 | 2013-04-03 | 陈银凤 | Preparation method of polyamide wax anti-settling agent |
| CN103788368A (en) * | 2014-01-27 | 2014-05-14 | 湖南大学 | Aqueous polyamide as well as preparation method and application thereof |
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2014
- 2014-12-16 CN CN201410774199.3A patent/CN104403100B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2190388A (en) * | 1986-03-27 | 1987-11-18 | Coates Brothers Plc | Polyamides and thixotropic compositions containing them |
| CN103013216A (en) * | 2011-09-26 | 2013-04-03 | 陈银凤 | Preparation method of polyamide wax anti-settling agent |
| CN103788368A (en) * | 2014-01-27 | 2014-05-14 | 湖南大学 | Aqueous polyamide as well as preparation method and application thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018010615A1 (en) * | 2016-07-15 | 2018-01-18 | Deuchem (Shanghai) Chemical Co., Ltd. | Novel non-ionic polyamide rheology modifier for aqueous coating |
| CN110709480A (en) * | 2017-04-11 | 2020-01-17 | 巴斯夫涂料有限公司 | Coating for producing structured surfaces |
| CN110709480B (en) * | 2017-04-11 | 2022-07-12 | 巴斯夫涂料有限公司 | Coating for producing structured surfaces |
| US11505649B2 (en) | 2017-09-28 | 2022-11-22 | Dupont Polymers, Inc. | Polymerization process |
| CN112292427A (en) * | 2018-03-27 | 2021-01-29 | 太阳化学公司 | Water-based inks with renewable materials |
| CN109735160A (en) * | 2018-12-21 | 2019-05-10 | 浙江丰虹新材料股份有限公司 | A kind of easy distributed aqueous polyamide wax and preparation method and application |
| CN112589318A (en) * | 2020-11-12 | 2021-04-02 | 深圳市晨日科技股份有限公司 | Water-soluble lead-free soldering paste, water-washing solder paste and preparation method thereof |
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