CN104403100B - A kind of preparation method of aqueous polyamide thixotroping anti-settling agent - Google Patents
A kind of preparation method of aqueous polyamide thixotroping anti-settling agent Download PDFInfo
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- CN104403100B CN104403100B CN201410774199.3A CN201410774199A CN104403100B CN 104403100 B CN104403100 B CN 104403100B CN 201410774199 A CN201410774199 A CN 201410774199A CN 104403100 B CN104403100 B CN 104403100B
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Abstract
The present invention relates to chemical industry printing ink paint field, the preparation method being specifically related to a kind of aqueous polyamide thixotroping anti-settling agent, including following procedure of processing: the first step, first by binary acid, hydroxyl organic acid and diamine copolymerization, obtain the copolyamide prepolymer of hydroxyl；Second step, acidifying: the copolyamide prepolymer of hydroxyl and acidulant are carried out binary copolymerization reaction, obtains carboxylic polyamide；3rd step, carboxylic polyamide and alkali are neutralized, namely obtain aqueous polyamide thixotroping anti-settling agent.This preparation method is simple, cheaper starting materials, it is simple that the aqueous polyamide prepared has technique, good product quality, anti-settling agent mainly as coating uses, it is possible to balances sag resistance and the levelability of film preferably, can compose the thixotropic property that lance coating system is higher, and there is excellent thickening, anti-settling effect, the precipitation of face in coating, filler can be effectively prevented, can be widely applied in aqueous systems coating, applied widely.
Description
Technical field
The present invention relates to chemical industry printing ink paint field, the preparation method being specifically related to a kind of aqueous polyamide thixotroping anti-settling agent.
Background technology
In prior art, the stream in order to control liquid system becomes, it is common to use such as silicon dioxide, castor oil hydrogenated, organically-modified bentonite and polyamide wax.In polyamide and polyamide fat field, there is a large amount of patent, for instance DE69523221, EP0239419, US5510452l etc..Also just like, described in EP0509202 and DE69704691, also using the combination of modified bentonite and polyamide.
Above technology is usually powder or slurry, but powder or slurry must utilize solvent and apply shearing force and convert it into semi-finished product, or utilizes special temperature to control to be introduced into liquid coating system.Unless required difficult control of temperature, complex process, temperature, once too high or too low prepared finished product coating system all can produce granule, causes coating products defect.So that there is delustring and opaque in the clear dope prepared, and these coating cannot be used for water-based system, and range of application is limited to.
Summary of the invention
It is an object of the invention to for above-mentioned deficiency of the prior art, the preparation method that a kind of aqueous polyamide thixotroping anti-settling agent is provided, there is technique simple, good product quality, the anti-settling agent mainly as coating uses, sag resistance and the levelability 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, the precipitation of face in coating, filler can be effectively prevented, can be widely applied in aqueous systems coating, applied widely.
The purpose of the present invention is achieved through the following technical solutions.
The preparation method of a kind of aqueous polyamide thixotroping anti-settling agent, including following procedure of processing: the first step, first by binary acid, hydroxyl organic acid and diamine copolymerization, obtains the copolyamide prepolymer of hydroxyl；
Second step, acidifying: the copolyamide prepolymer of hydroxyl and acidulant are carried out binary copolymerization reaction, obtain carboxylic polyamide, and described acidulant is binary acid or anhydride；
3rd step, carboxylic polyamide and alkali are neutralized, namely obtain aqueous polyamide thixotroping anti-settling agent.Further, by step 2 prepare carboxylic polyamide add a certain amount of alkali neutralize, when product can reaction soluble in water complete.Specifically, carboxylic polyamide is 1:0.5 ~ 1 with the mol ratio of alkali.
Wherein, the described first step, particularly as follows: dried diamine, binary 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 binary acid and hydroxyl organic acid mol ratio are 0.1-5:1, then add a certain amount of solvent and catalyst in flask, pre-polymerization 1-3h at 70-160 DEG C, obtain the Polvamide prepolymer of hydroxyl, then vacuum sloughs water, prepare the copolyamide prepolymer of hydroxyl；Described solvent is DMF or NMP, and described catalyst is pyridine, triphenyl phosphite, imidazoles or phenyl hypophosphorous acid.
Wherein, the addition of described solvent is the 10-50% of the copolyamide prepolymer gross mass of hydroxyl, and the addition of described catalyst is the 3-6 ‰ of the copolyamide prepolymer gross mass of hydroxyl.
Wherein, described second step, particularly as follows: the reaction system of the copolyamide prepolymer of the hydroxyl first step prepared is cooled to 50 DEG C, add acidulant and acidifying catalyst, when acidulant is anhydride, reaction system is warming up to 60-90 DEG C of reaction 2-4h；When acidulant is binary acid, then reaction system being warming up to 180 DEG C and react dehydration, the response time is 3-6h, after reaction fully, is cooled to room temperature, obtains carboxylic polyamide；Described acidifying catalyst is pyridine, N-picoline, butyl titanate, triphenyl phosphite or dibutyl tin laurate.
Wherein, in the described first step, the temperature of copolyreaction is 70-160 DEG C, and the response time is 1-3h；In described second step, the reaction pressure 0.1MPa in water smoking, the reaction temperature of described acidifying is 50-190 DEG C, and the response time is 1-6h；In described 3rd step, alkali neutral temperature is 30-50 DEG C, response time 1-2h.
Wherein, described anhydride is one or more the mixture in pyromellitic dianhydride, phthalic anhydride and cis-butenedioic anhydride.
Wherein, described binary acid is one or more the mixture in adipic acid, p-phthalic acid, M-phthalic acid, Azelaic Acid, decanedioic acid, 1,3-propanedicarboxylic acid, succinic acid.
Wherein, described diamine is one or more the mixture in decamethylene diamine, hexamethylene diamine, ethylenediamine, diethylenetriamine, propane diamine, heptamethylene diamine, octamethylenediamine, nonamethylene diamine, p-phenylenediamine, o-phenylenediamine, m-diaminobenzene., polyethyleneoxide diamine, butanediamine, pentanediamine.
Wherein, described hydroxyl organic acid is one or more the mixture in malic acid, dihydromethyl propionic acid, ten dihydroxystearic acids, hydroxyacetic acid, P-hydroxybenzoic acid, citric acid, tartaric acid.
Wherein, described alkali is that potassium hydroxide, sodium hydroxide, triethylene diamine, four ethylene triamines, multiethylene polyamine, ethylenediamine, propane diamine, butanediamine, hexamethylene diamine, ethanolamine etc. have one or more the mixture in the water-soluble substances of similar structures.
Beneficial effects of the present invention:
(1) preparation method that the invention discloses a kind of aqueous polyamide thixotroping anti-settling agent, is by after binary acid, hydroxyl organic acid and diamine copolymerization, then carries out acidifying, neutralize then through alkali and obtain product;This preparation method is simple, cheaper starting materials, it is simple that the aqueous polyamide prepared has technique, good product quality, anti-settling agent mainly as coating uses, sag resistance and the levelability 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, the precipitation of face in coating, filler can be effectively prevented.
(2) polyamide is generally formed by binary acid and diamine polycondensation, can be divided into solvent-borne type polyamide and non-solvent polyamide by dissolubility, because having the groups such as highly polar amido link, is being added into coating or pre-activate formation network structure.Currently used is solvent-borne type polyamide anti-settling agent, and the solvent-borne type polyamide of early stage is dissolved in benzene, dimethylbenzene, but the arene solution abnormal smells from the patient of this resin is big, contaminated environment, harm workers ' health, limits its further use.The aqueous polyamide thixotroping anti-settling agent that the present invention prepares, it is adaptable to aqueous solution systems, can effectively reduce VOC (VOC) and air noxious pollutant.
(3) the aqueous polyamide thixotroping anti-settling agent that the present invention prepares has environmental advantages such as not firing, nontoxic, pollution-free, the particularly strict restriction to organic solvent use with waste discharge recently as the surging of organic solvent price and environmental administration, aqueous polyamide thixotroping anti-settling agent replaces organic solvent type polyamide becomes the important directions of this field current development.
Detailed description of the invention
The invention will be further described with the following Examples.
Embodiment 1
Citric acid 20g, adipic acid 80g, decamethylene diamine 62g, ten dihydroxystearic acid 50g are put into vacuum drying oven, dries 12 hours at 60 DEG C.Dried raw material is added in there-necked flask, in flask, add 150mLN monomethyl ketopyrrolidine as solvent, at 80 DEG C after pre-polymerization 1 hour, be warmed up to 110 DEG C, add 12mL phosphorous acid triphen cruel, after reaction 0.5h, it is warmed up to 125 DEG C, after reacting 2 hours, cooling, add 10.3g maleic anhydride and 3g pyridine, react 2 hours after being stirred and heated to 80 DEG C, obtain acidified aqueous polyamide；Add 7g triethanolamine to be neutralized, obtain product.
Embodiment 2
Malic acid 80g, M-phthalic acid 60g, hexamethylene diamine 39.6g, dihydromethyl propionic acid are put into vacuum drying oven, dries 12 hours at 60 DEG C.Dried raw material is added in there-necked flask, 150mLN monomethyl ketopyrrolidine is added as solvent in flask, at 70 DEG C after pre-polymerization 2 hours, it is warmed up to 150 DEG C, adds 12mL phosphorous acid triphen extremely, after reacting 2 hours, cooling, add 52.1g phthalic anhydride and 3g pyridine, react 2 hours after being stirred and heated to 80 DEG C, add ethanolamine 20g i.e. obtaining aqueous polyamide thixotroping anti-settling agent.
Embodiment 3
Malic acid 15g, adipic acid 60g, 1,7 one heptamethylene diamine 39g, ten dihydroxystearic acid 20g are put into vacuum drying oven, dries 12 hours at 60 DEG C.Dried raw material is added in there-necked flask, 150mLN monomethyl ketopyrrolidine is added as solvent in flask, at 100 DEG C after pre-polymerization 1 hour, it is warmed up to 150 DEG C, adds 12mL phenyl hypophosphorous acid, after reacting 2 hours, cooling, add 12g maleic acid to join and 3g dimethylamino naphthyridine, react 2 hours after being stirred and heated to 60 DEG C, add potassium hydroxide 5g and namely obtain aqueous polyamide thixotroping anti-settling agent.
Embodiment 4
The first step, octamethylenediamine by dried, p-phthalic acid and dihydromethyl propionic acid add in there-necked flask, the mol ratio of octamethylenediamine and dihydromethyl propionic acid is 0.5:1, the mol ratio of p-phthalic acid and dihydromethyl propionic acid is 0.1:1, then in flask, add a certain amount of solvent and catalyst, pre-polymerization 3h at 70 DEG C, then vacuum sloughs water；Described solvent is DMF, and described catalyst is pyridine.The addition of described solvent is 120ml/mol, and the addition of described catalyst is 10ml/mol.
Second step, in the reaction system of the first step, be cooled to 50 DEG C, add acidulant and acidifying catalyst, when acidulant is pyromellitic dianhydride, reaction system is warming up to 70 DEG C of reaction 2.5h, after reaction fully, is cooled to room temperature；Described acidifying catalyst is butyl titanate.
3rd step, carboxylic polyamide and sodium hydroxide being neutralized, the mol ratio of carboxylic polyamide and alkali is 1:0.5, and alkali neutral temperature is 30 DEG C, response time 2h, namely obtains aqueous polyamide thixotroping anti-settling agent.
Embodiment 5
The first step, p-phenylenediamine by dried, Azelaic Acid and hydroxyacetic acid add in there-necked flask, the mol ratio of p-phenylenediamine and hydroxyacetic acid is 0.72:1, the mol ratio of Azelaic Acid and hydroxyacetic acid is 2.5:1, then in flask, add a certain amount of solvent and catalyst, pre-polymerization 2h at 100 DEG C, then vacuum sloughs water；Described solvent is NMP, and described catalyst is triphenyl phosphite.The addition of described solvent is 160ml/mol, and the addition of described catalyst is 15ml/mol.
Second step, in the reaction system of the first step, be cooled to 50 DEG C, add acidulant and acidifying catalyst, when acidulant is phthalic anhydride, reaction system is warming up to 80 DEG C of reaction 3h, after reaction fully, is cooled to room temperature；Described acidifying catalyst is triphenyl phosphite.
3rd step, carboxylic polyamide and four ethylene triamines being neutralized, the mol ratio of carboxylic polyamide and alkali is 1:0.8, and alkali neutral temperature is 40 DEG C, response time 1.5h, namely obtains aqueous polyamide thixotroping anti-settling agent.
Embodiment 6
The first step, diethylenetriamine by dried, decanedioic acid and ten dihydroxystearic acids add in there-necked flask, the mol ratio of diethylenetriamine and ten dihydroxystearic acids is 0.96:1, the mol ratio of decanedioic acid and ten dihydroxystearic acids is 5:1, then in flask, add a certain amount of solvent and catalyst, pre-polymerization 1h at 160 DEG C, then vacuum sloughs water；Described solvent is DMF, and described catalyst is phenyl hypophosphorous acid.The addition of described solvent is 135ml/mol, and the addition of described catalyst is 13ml/mol.
Second step, in the reaction system of the first step, be cooled to 50 DEG C, add acidulant and acidifying catalyst, when acidulant is binary acid, then reaction system being warming up to 180 DEG C and react dehydration, the response time is 4h, the reaction pressure 0.1MPa in water smoking, after reaction fully, is cooled to room temperature；Described acidifying catalyst is dibutyl tin laurate.
3rd step, carboxylic polyamide and multiethylene polyamine being neutralized, the mol ratio of carboxylic polyamide and alkali is 1:1, and alkali neutral temperature is 50 DEG C, response time 1h, namely obtains aqueous polyamide thixotroping anti-settling agent.
Finally should be noted that; above example is only in order to illustrate technical scheme; but not limiting the scope of the invention; although having made to explain to the present invention with reference to preferred embodiment; it will be understood by those within the art that; technical scheme can be modified or equivalent replacement, without deviating from the spirit and scope of technical solution of the present invention.
Claims (6)
1. the preparation method of an aqueous polyamide thixotroping anti-settling agent, it is characterised in that: include following procedure of processing: the first step, first by binary acid, hydroxyl organic acid and diamine copolymerization, obtain the copolyamide prepolymer of hydroxyl；
Second step, acidifying: the copolyamide prepolymer of hydroxyl and acidulant are carried out binary copolymerization reaction, obtain carboxylic polyamide, and described acidulant is binary acid or anhydride；
3rd step, carboxylic polyamide and alkali are neutralized, namely obtain aqueous polyamide thixotroping anti-settling agent；
The described first step, particularly as follows: dried diamine, binary acid and hydroxyl organic acid are added in there-necked flask, diamine and hydroxyl organic acid mol ratio are 0.5-0.96:1, binary acid and hydroxyl organic acid mol ratio are 0.1-5:1, then in flask, add a certain amount of solvent and catalyst, pre-polymerization 1-3h at 70-160 DEG C, obtain the Polvamide prepolymer of hydroxyl, vacuum sloughs water again, prepares the copolyamide prepolymer of hydroxyl；Described solvent is DMF or NMP, and described catalyst is pyridine, triphenyl phosphite, imidazoles or phenyl hypophosphorous acid；
The addition of described solvent is the 10-50% of the copolyamide prepolymer gross mass of hydroxyl, and the addition of described catalyst is the 3-6 ‰ of the copolyamide prepolymer gross mass of hydroxyl；
Described second step, particularly as follows: the reaction system of the copolyamide prepolymer of the hydroxyl first step prepared is cooled to 50 DEG C, adds acidulant and acidifying catalyst, when acidulant is anhydride, reaction system is warming up to 60-90 DEG C of reaction 2-4h；When acidulant is binary acid, then reaction system being warming up to 180 DEG C, the response time is 3-6h, after reaction fully, is cooled to room temperature, obtains carboxylic polyamide；Described acidifying catalyst is pyridine, N-picoline, butyl titanate, triphenyl phosphite or dibutyl tin laurate；
In the described first step, the temperature of copolyreaction is 70-160 DEG C, and the response time is 1-3h；In described second step, the reaction temperature of described acidifying is 50-190 DEG C, and the response time is 1-6h；In described 3rd step, alkali neutral temperature is 30-50 DEG C, response time 1-2h.
2. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterised in that: described anhydride is one or more the mixture in pyromellitic dianhydride, phthalic anhydride and cis-butenedioic anhydride.
3. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterised in that: described binary acid is one or more the mixture in adipic acid, p-phthalic acid, M-phthalic acid, Azelaic Acid, decanedioic acid, 1,3-propanedicarboxylic acid, succinic acid.
4. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterised in that: described diamine is one or more the mixture in decamethylene diamine, hexamethylene diamine, ethylenediamine, diethylenetriamine, propane diamine, heptamethylene diamine, octamethylenediamine, nonamethylene diamine, p-phenylenediamine, o-phenylenediamine, m-diaminobenzene., polyethyleneoxide diamine, butanediamine, pentanediamine.
5. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterised in that: described hydroxyl organic acid is one or more the mixture in malic acid, dihydromethyl propionic acid, ten dihydroxystearic acids, hydroxyacetic acid, P-hydroxybenzoic acid, citric acid, tartaric acid.
6. the preparation method of a kind of aqueous polyamide thixotroping anti-settling agent according to claim 1, it is characterised in that: described alkali is one or more the mixture in potassium hydroxide, sodium hydroxide, triethylene diamine, four ethylene triamines, multiethylene polyamine, ethylenediamine, propane diamine, butanediamine, hexamethylene diamine, ethanolamine.
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| CN107629538B (en) * | 2016-07-15 | 2022-01-14 | 德谦（上海）化学有限公司 | Novel nonionic polyamide rheology modifiers for aqueous coatings |
| EP3609960B1 (en) * | 2017-04-11 | 2023-09-27 | BASF Coatings GmbH | Coating agent which creates structured surfaces |
| WO2019067517A1 (en) | 2017-09-28 | 2019-04-04 | E. I. Du Pont De Nemours And Company | Polymerization process |
| US12031056B2 (en) * | 2018-03-27 | 2024-07-09 | Sun Chemical Corporation | 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 easily dispersible water-based polyamide wax and preparation method and application |
| CN112589318B (en) * | 2020-11-12 | 2022-05-27 | 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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|---|---|---|---|---|
| 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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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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