CN106146743A - A kind of preparation method of high-performance acrylic acid esters resin - Google Patents
A kind of preparation method of high-performance acrylic acid esters resin Download PDFInfo
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- CN106146743A CN106146743A CN201610622898.5A CN201610622898A CN106146743A CN 106146743 A CN106146743 A CN 106146743A CN 201610622898 A CN201610622898 A CN 201610622898A CN 106146743 A CN106146743 A CN 106146743A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/06—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
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Abstract
The present invention relates to the preparation method of a kind of high-performance acrylic acid esters resin, add water, dodecylbenzene sodium sulfonate, fatty alcohol-polyoxyethylene ether, 2 acrylamide 2 methyl propane sulfonic acids, heat up stirring, adds A monomer, emulsifying 40min, it is warmed up to 70 DEG C and starts logical recirculation water, it is warmed up to 85 DEG C and adds potassium persulfate solution, react 2h, add FLUTICASONE PROPIONATE, stirring reaction, obtains stratum nucleare emulsion；It is simultaneously added dropwise B monomer and potassium persulfate solution in gained stratum nucleare emulsion, drip stirring reaction, cool to 50 DEG C, add dodecylbenzene sodium sulfonate and fatty alcohol-polyoxyethylene ether, response time 70min, 70 DEG C of reaction 1h, adding ammonia adjusts pH value to 7 ~ 8, obtaining acrylic resin, this preparation method both can make acrylic resin wearability be greatly improved, and can improve again the defect of acrylic resin emulsion film forming jaundice.
Description
Present patent application is divisional application.The application number of original bill is: 201510102534X, and the applying date is: 2015
03 month 10 days, denomination of invention was: the preparation method of a kind of high-performance acrylic acid esters resin.
Technical field
The present invention relates to the preparation method of a kind of acrylic resin, particularly to a kind of high-performance acrylic acid esters tree
The preparation method of fat.
Background technology
Acrylic resin group coating to be used as, adhesive and finishing agent, the market of its maximum is car paint, and this is external
Light industry, household electrical appliance, metal household implements, aluminum products, coiled material industry, instrument and meter, build, textile, plastic, wooden
The industry such as product, papermaking is all widely used.The direction of acrylic resin coating hydrotropismization, multifunction and high function is sent out
Exhibition.
But acrylic resin abrasion resisting poor performance, emulsion film forming somewhat turn to be yellow, it is therefore desirable to be modified it, protect
Protect the safety of lives and properties.
Water-soluble medium makes acrylate containing fluorine resin wetted and has mobility, and high boiling solvent then rises and is dried delay
The effect of agent, after application during drying and sintering, can prevent film from chapping.Even if high boiling solvent is under fluororesin forming temperature
Evaporation, does not the most produce impact to film.
Summary of the invention
It is desirable to provide the preparation method of a kind of high-performance acrylic acid esters resin, select 2-acrylamide-2-first
Base propane sulfonic acid substitutes traditional acrylic or methacrylic acid, improves associativity and the dispersibility of stratum nucleare, with fluorine class wear resistence list
Body is aggregated on the main chain of acrylic resin, and epoxide and amino graft polymerization are to acrylic resin main chain
On, by FLUTICASONE PROPIONATE, remaining persulfate is processed, improve acrylic resin emulsion film forming and somewhat send out
Yellow defect, selects slaine to have acrylic resin to cross-link simultaneously, improves the wearability of acrylic resin.
The present invention is by the following technical solutions:
1. the preparation method of a high-performance acrylic acid esters resin, it is characterised in that:
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 65g, dodecylbenzene sodium sulfonate are added
0.55g, fatty alcohol-polyoxyethylene ether 0.25g, 2-acrylamide-2-methyl propane sulfonic 0.3g, be warming up to 50 DEG C, stirs 40min,
Add A monomer, emulsifying 40min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 85 DEG C of water-soluble potassium peroxydisulfates of dropping 8g
Solution 8.2g, time for adding 1h, drip reaction 2h, add cantharidin 1g and FLUTICASONE PROPIONATE 0.3g, 75 DEG C of stirrings
Reaction 2h, obtains stratum nucleare emulsion；
Described A monomer be by perfluorinated allyl base benzene 3g, butyl acrylate 2g, 2-(Acryloyloxy)ethanol 3g, ethyl acrylate 3.0g and
Acrylamide 4g mixes；
(2) in step (1) gained stratum nucleare emulsion, it is simultaneously added dropwise B monomer and with 8g water-soluble potassium persulfate solution 8.2g, drips
Add time 1h, drip 80 DEG C of stirring reaction 2h, add titanium dioxide dicyclopentadiene 0.5g, 75 DEG C of reaction 2h, cool to
50 DEG C, addition dodecylbenzene sodium sulfonate 0.395g and fatty alcohol-polyoxyethylene ether 0.135g, response time 70min, addition β-
Glucosidase 0.02g and Alumen 0.21g, 70 DEG C of reaction 1h, add ammonia and adjust pH value to 7 ~ 8, obtain described high-performance acrylic acid
Esters resin；
Described B monomer is by Flumiclorac pentyl 4g, butyl acrylate 3g, 2-(Acryloyloxy)ethanol 4.0g, 2-(Acryloyloxy)ethanol 4.0g, benzene
Ethylene 0.6g, allyl dichloride amine 1g and 2,3,5,4-tetrahydroxystilbene glucoside 3g mixing composition.
The preparation method of 2 one kinds of high-performance acrylic acid esters resins, it is characterised in that:
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 85g, dodecylbenzene sodium sulfonate are added
2.5g, fatty alcohol-polyoxyethylene ether 0.6g, 2-acrylamide-2-methyl propane sulfonic 3.2g, be warming up to 40 DEG C, stirs 40min, adds
Enter A monomer, emulsifying 60min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 80 DEG C, the water-soluble Ammonium persulfate. of dropping 8g
Solution 8.6g, time for adding 2h, drip reaction 2h, add 1,2-epoxy-4-vinyl cyclohexane 4g and fluticasone third
Acid esters 0.3g, 80 DEG C of stirring reaction 2h, obtain stratum nucleare emulsion；
Described A monomer is by 3-methylamino-4,4,4-trifluorobutene acetoacetic ester 6g, 3-perfluoro capryl 2-Hydroxypropyl acrylate
7g, methyl methacrylate 7g, ethyl acrylate 5g and 2,3,5,4-tetrahydroxystilbene glucoside 7g mix；
(2) in step (1) gained stratum nucleare emulsion, it is simultaneously added dropwise B monomer and with 8g water-soluble ammonium persulfate solution 8.8g, drips
Add time 2h, drip insulation 80 DEG C stirring reaction 2h, add cyanidin-3-O-glucoside 2.2g, during 85 DEG C of reactions
Between 3h, cool to 50 DEG C, add dodecylbenzene sodium sulfonate 0.375g and fatty alcohol-polyoxyethylene ether 0.125g, response time
60min, adds epoxychloropropane 0.4g and Disulfatozirconic acid. 0.36g, 70 DEG C of reaction 1h, adds ammonia and adjust pH value to 7 ~ 8, obtain described height
Performance acrylic resin；
Described B monomer is by 4,4,4-trifluorobutene nitrile 7g, 3-perfluoro capryl 2-Hydroxypropyl acrylate 6g, methyl methacrylate
6.5g, 2-(Acryloyloxy)ethanol 7.5g, styrene 1.5g, N, N-di-2-ethylhexylphosphine oxide methyl-prop enamine 3.2g and 2,3,5,4-tetrahydroxy two
Styrene glucoside 5g mixes composition.
The preparation method of 3 one kinds of high-performance acrylic acid esters resins, it is characterised in that:
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 75g, dodecylbenzene sodium sulfonate are added
0.99, fatty alcohol-polyoxyethylene ether 0.36g and 2-acrylamide-2-methyl propane sulfonic 1.8g, is warming up to 40 DEG C, stirs 30min,
Add A monomer, emulsifying 45min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 80 DEG C, the water-soluble single over cure of dropping 6g
Potassium hydrogen phthalate solution 6.8g, time for adding 2.5h, drip reaction 2.5h, add 1,1,1-tri-fluoro-2,3-expoxy propane 3g and
FLUTICASONE PROPIONATE 0.6g, stirring reaction 3h, obtain stratum nucleare emulsion；
Described A monomer is by 4-bromo-3,3,4,4-tetrafluoro butylene 3.5g, butyl acrylate 5.5g, hydroxypropyl methacrylate
4g, ethyl acrylate 3g, 3-methyl-2-butene amine 3.2g, 2,3,5,4-tetrahydroxystilbene glucoside 4.5g mixing and
Become；
(2) in step (1) gained stratum nucleare emulsion, B monomer it is simultaneously added dropwise and with the water-soluble potassium monopersulfate solutions of 8g
8.45g, time for adding 1.5h, drip 80 DEG C of stirring reaction 2h, add kaempferol 0.8g, 80 DEG C of response time 1 ~ 3h, fall
Temperature, to 50 DEG C, adds dodecylbenzene sodium sulfonate 0.375g and fatty alcohol-polyoxyethylene ether 0.125g, response time 60min, adds
Enter naloxone 0.25g and potassium ferricyanide 0.32g, 70 DEG C of reaction 1h, add ammonia and adjust pH value to 7 ~ 8, obtain described high-performance acrylic acid
Esters resin；
Described B monomer is by the bromo-4-of 5-chloro-4,5,5-trifluoro amylene 2.6g, butyl acrylate 4.5g, methacrylic acid hydroxypropyl
Ester 4.9g, 2-(Acryloyloxy)ethanol 4.9g and 2,3,5,4-tetrahydroxystilbene glucoside 3g mixing composition.
The beneficial effects of the present invention is:
(1) the wearability acrylic resin prepared by, has stronger wearability, and the film forming of gained emulsion is transparent, improves
Traditional persulfate does the defect of acrylic resin emulsion film forming jaundice prepared by initiator；
(2) perfluorinated allyl base benzene, 3-methylamino-4,4,4-trifluorobutene acetoacetic ester, 4-bromo-3,3,4,4-tetrafluoro fourth are selected
The fluorochemical monomers such as the bromo-4-of alkene, 5-chloro-4,5,5-trifluoro amylene and slaine (Alumen, Disulfatozirconic acid., potassium ferricyanide) improve acrylate
Resinoid wearability；
(3) under stratum nucleare and shell act on jointly, improve the wearability of acrylic resin；
(4) remaining persulfate is processed by FLUTICASONE PROPIONATE, improves acrylic resin emulsion film forming somewhat
The defect of jaundice；
(5) epoxide such as cantharidin, 1,2-epoxy-4-vinyl cyclohexane, 1,1,1-tri-fluoro-2,3-expoxy propane and third
The amino of olefin(e) acid esters resin reacts, and makes the side chain of resin also have good wearability；
(6) Flumiclorac pentyl also makes acrylic resin have certain light resistance.
Detailed description of the invention
In order to be more fully understood that and implement the present invention, further illustrate the present invention below in conjunction with specific embodiment.
Example 1
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 65g, dodecylbenzene sodium sulfonate are added
0.55g, fatty alcohol-polyoxyethylene ether 0.25g, 2-acrylamide-2-methyl propane sulfonic 0.3g, be warming up to 50 DEG C, stirs 40min,
Add A monomer, emulsifying 40min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 85 DEG C of water-soluble potassium peroxydisulfates of dropping 8g
Solution 8.2g, time for adding 1h, drip reaction 2h, add cantharidin 1g and FLUTICASONE PROPIONATE 0.3g, 75 DEG C of stirrings
Reaction 2h, obtains stratum nucleare emulsion；
Described A monomer be by perfluorinated allyl base benzene 3g, butyl acrylate 2g, 2-(Acryloyloxy)ethanol 3g, ethyl acrylate 3.0g and
Acrylamide 4g mixes；
(2) in step (1) gained stratum nucleare emulsion, it is simultaneously added dropwise B monomer and with 8g water-soluble potassium persulfate solution 8.2g, drips
Add time 1h, drip 80 DEG C of stirring reaction 2h, add titanium dioxide dicyclopentadiene 0.5g, 75 DEG C of reaction 2h, cool to
50 DEG C, addition dodecylbenzene sodium sulfonate 0.395g and fatty alcohol-polyoxyethylene ether 0.135g, response time 70min, addition β-
Glucosidase 0.02g and Alumen 0.21g, 70 DEG C of reaction 1h, add ammonia and adjust pH value to 7 ~ 8, obtain described high-performance acrylic acid
Esters resin；
Described B monomer is by Flumiclorac pentyl 4g, butyl acrylate 3g, 2-(Acryloyloxy)ethanol 4.0g, 2-(Acryloyloxy)ethanol 4.0g, benzene
Ethylene 0.6g, allyl dichloride amine 1g and 2,3,5,4-tetrahydroxystilbene glucoside 3g mixing composition.
Example 2
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 85g, dodecylbenzene sodium sulfonate are added
2.5g, fatty alcohol-polyoxyethylene ether 0.6g, 2-acrylamide-2-methyl propane sulfonic 3.2g, be warming up to 40 DEG C, stirs 40min, adds
Enter A monomer, emulsifying 60min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 80 DEG C, the water-soluble Ammonium persulfate. of dropping 8g
Solution 8.6g, time for adding 2h, drip reaction 2h, add 1,2-epoxy-4-vinyl cyclohexane 4g and fluticasone third
Acid esters 0.3g, 80 DEG C of stirring reaction 2h, obtain stratum nucleare emulsion；
Described A monomer is by 3-methylamino-4,4,4-trifluorobutene acetoacetic ester 6g, 3-perfluoro capryl 2-Hydroxypropyl acrylate
7g, methyl methacrylate 7g, ethyl acrylate 5g and 2,3,5,4-tetrahydroxystilbene glucoside 7g mix；
(2) in step (1) gained stratum nucleare emulsion, it is simultaneously added dropwise B monomer and with 8g water-soluble ammonium persulfate solution 8.8g, drips
Add time 2h, drip insulation 80 DEG C stirring reaction 2h, add cyanidin-3-O-glucoside 2.2g, during 85 DEG C of reactions
Between 3h, cool to 50 DEG C, add dodecylbenzene sodium sulfonate 0.375g and fatty alcohol-polyoxyethylene ether 0.125g, response time
60min, adds epoxychloropropane 0.4g and Disulfatozirconic acid. 0.36g, 70 DEG C of reaction 1h, adds ammonia and adjust pH value to 7 ~ 8, obtain described height
Performance acrylic resin；
Described B monomer is by 4,4,4-trifluorobutene nitrile 7g, 3-perfluoro capryl 2-Hydroxypropyl acrylate 6g, methyl methacrylate
6.5g, 2-(Acryloyloxy)ethanol 7.5g, styrene 1.5g, N, N-di-2-ethylhexylphosphine oxide methyl-prop enamine 3.2g and 2,3,5,4-tetrahydroxy two
Styrene glucoside 5g mixes composition.
Example 3
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 75g, dodecylbenzene sodium sulfonate are added
0.99, fatty alcohol-polyoxyethylene ether 0.36g and 2-acrylamide-2-methyl propane sulfonic 1.8g, is warming up to 40 DEG C, stirs 30min,
Add A monomer, emulsifying 45min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 80 DEG C, the water-soluble single over cure of dropping 6g
Potassium hydrogen phthalate solution 6.8g, time for adding 2.5h, drip reaction 2.5h, add 1,1,1-tri-fluoro-2,3-expoxy propane 3g and
FLUTICASONE PROPIONATE 0.6g, stirring reaction 3h, obtain stratum nucleare emulsion；
Described A monomer is by 4-bromo-3,3,4,4-tetrafluoro butylene 3.5g, butyl acrylate 5.5g, hydroxypropyl methacrylate
4g, ethyl acrylate 3g, 3-methyl-2-butene amine 3.2g, 2,3,5,4-tetrahydroxystilbene glucoside 4.5g mixing and
Become；
(2) in step (1) gained stratum nucleare emulsion, B monomer it is simultaneously added dropwise and with the water-soluble potassium monopersulfate solutions of 8g
8.45g, time for adding 1.5h, drip 80 DEG C of stirring reaction 2h, add kaempferol 0.8g and aminopterin 0.21g, 80 DEG C
Response time 1 ~ 3h, cools to 50 DEG C, adds dodecylbenzene sodium sulfonate 0.375g and fatty alcohol-polyoxyethylene ether 0.125g, instead
60min between Ying Shi, adds naloxone 0.25g, potassium ferricyanide 0.32g and 5-trifluoromethyl uracil 0.17g, 70 DEG C of reaction 1h, adds
Ammonia adjusts pH value to 7 ~ 8, obtains described high-performance acrylic acid esters resin；
Described B monomer is by the bromo-4-of 5-chloro-4,5,5-trifluoro amylene 2.6g, butyl acrylate 4.5g, methacrylic acid hydroxypropyl
Ester 4.9g, 2-(Acryloyloxy)ethanol 4.9g and 2,3,5,4-tetrahydroxystilbene glucoside 3g mixing composition.
Beneficial effects of the present invention is further illustrated below by relevant experimental data:
Table 1 high-performance acrylic acid esters resin institute's film forming elongation at break and outward appearance
| Experimental group | Market ARB | Example 1 | Example 2 | Example 3 |
| Elongation at break/% | 90.07 | 149.78 | 132.63 | 126.69 |
| Film outward appearance | Light yellow | Water white transparency | Water white transparency | Water white transparency |
Table 1 middle finger object detection method reference: Jiang Weiqi. leather finish physical and chemical inspection [M]. China Light Industry Press, 1999,
82-96.Employ wearability resin molding of the present invention, elongation at break be improved significantly.
The abrasion performance of table 2 high-performance acrylic acid esters resin institute film forming
| Experimental group | Market ARB | Example 1 | Example 2 | Example 3 |
| Abrasion loss/mg | 34 | 28 | 23 | 21 |
Note: use 120# sand round
The data of table 2 are to carry out under GB1768-89 paint film abrasion performance assay method, and wear-resisting those at least is best, example
Abrasivity is preferable.
Claims (1)
1. the preparation method of a high-performance acrylic acid esters resin, it is characterised in that:
(1) in the 250ml there-necked flask with agitator, thermometer and condensing tube, water 75g, dodecylbenzene sodium sulfonate are added
0.99, fatty alcohol-polyoxyethylene ether 0.36g and 2-acrylamide-2-methyl propane sulfonic 1.8g, is warming up to 40 DEG C, stirs 30min,
Add A monomer, emulsifying 45min, be warmed up to 70 DEG C and start logical recirculation water, be warmed up to 80 DEG C, the water-soluble single over cure of dropping 6g
Potassium hydrogen phthalate solution 6.8g, time for adding 2.5h, drip reaction 2.5h, add 1,1,1-tri-fluoro-2,3-expoxy propane 3g and
FLUTICASONE PROPIONATE 0.6g, stirring reaction 3h, obtain stratum nucleare emulsion；
Described A monomer is by 4-bromo-3,3,4,4-tetrafluoro butylene 3.5g, butyl acrylate 5.5g, hydroxypropyl methacrylate
4g, ethyl acrylate 3g, 3-methyl-2-butene amine 3.2g, 2,3,5,4-tetrahydroxystilbene glucoside 4.5g mixing and
Become；
(2) in step (1) gained stratum nucleare emulsion, B monomer it is simultaneously added dropwise and with the water-soluble potassium monopersulfate solutions of 8g
8.45g, time for adding 1.5h, drip 80 DEG C of stirring reaction 2h, add kaempferol 0.8g, 80 DEG C of response time 1 ~ 3h, fall
Temperature, to 50 DEG C, adds dodecylbenzene sodium sulfonate 0.375g and fatty alcohol-polyoxyethylene ether 0.125g, response time 60min, adds
Enter naloxone 0.25g and potassium ferricyanide 0.32g, 70 DEG C of reaction 1h, add ammonia and adjust pH value to 7 ~ 8, obtain described high-performance acrylic acid
Esters resin；
Described B monomer is by the bromo-4-of 5-chloro-4,5,5-trifluoro amylene 2.6g, butyl acrylate 4.5g, methacrylic acid hydroxypropyl
Ester 4.9g, 2-(Acryloyloxy)ethanol 4.9g and 2,3,5,4-tetrahydroxystilbene glucoside 3g mixing composition.
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| CN110330852A (en) * | 2019-07-15 | 2019-10-15 | 长沙秋点兵信息科技有限公司 | Preparation method of waterproof coating for ceramic tiles |
| CN111019034A (en) * | 2019-11-20 | 2020-04-17 | 上海东升新材料有限公司 | Butadiene-styrene latex for base coating and preparation method thereof |
| CN117700160A (en) * | 2023-11-29 | 2024-03-15 | 广东汇泉联骏化学工业有限公司 | Waste residue treatment method in methacrylate monomer synthesis process |
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| CN112852234B (en) * | 2018-10-09 | 2022-04-05 | 揭阳市鑫炜建材科技实业有限公司 | Preparation method of waterproof weather-resistant bi-component exterior wall latex paint |
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| CN110330852A (en) * | 2019-07-15 | 2019-10-15 | 长沙秋点兵信息科技有限公司 | Preparation method of waterproof coating for ceramic tiles |
| CN111019034A (en) * | 2019-11-20 | 2020-04-17 | 上海东升新材料有限公司 | Butadiene-styrene latex for base coating and preparation method thereof |
| CN111019034B (en) * | 2019-11-20 | 2022-08-16 | 上海东升新材料有限公司 | Butadiene-styrene latex for base coating and preparation method thereof |
| CN117700160A (en) * | 2023-11-29 | 2024-03-15 | 广东汇泉联骏化学工业有限公司 | Waste residue treatment method in methacrylate monomer synthesis process |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105037620B (en) | 2016-11-30 |
| CN106146742A (en) | 2016-11-23 |
| CN105037620A (en) | 2015-11-11 |
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