CN104672366A - High-solid low-viscosity acrylic resin and preparation method thereof - Google Patents
High-solid low-viscosity acrylic resin and preparation method thereof Download PDFInfo
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Abstract
The invention discloses high-solid low-viscosity acrylic resin and a preparation method thereof. The high-solid low-viscosity acrylic resin comprises butyl acetate, methylacrylic acid, glycidyl tertiary carboxylic ester, styrene, styrene dimer, an initiating agent and acrylate. The preparation method of the high-solid low-viscosity acrylic resin comprises the following steps: stirring mixed solution of part of butyl acetate and part of glycidyl tertiary carboxylic ester, heating, carrying out heat preservation, and refluxing for 0.5-1 hour; then dropwise adding part of mixture of initiating agent, acrylate, styrene, styrene dimer and methylacrylic acid, carrying out copolymerization reaction, and then carrying out heat preservation for 0.5-1.5 hours; and finally dropwise adding the rest mixture of butyl acetate, initiating agent and glycidyl tertiary carboxylic ester, then carrying out heat preservation for 1-2 hours, cooling and discharging. The high-solid low-viscosity acrylic resin disclosed by the invention has the advantages that the acrylic resin synthesis time is shortened, the production cost is reduced, the polymer molecular weight is low, and the branching degree is low; meanwhile, the problems that common acrylic resin on the market is high in viscosity and poor in acid and alkali resistance and water resistance are solved.
Description
Technical field
The present invention relates to resin art, particularly relate to a kind of high solid low viscosity acrylic resin and preparation method thereof.
Background technology
Acrylic resin is the resin synthesized for main raw material with acrylate or methacrylic ester, and the coating being main base by acrylic resin belongs to acrylate paint.Acrylic resin is generally transparent, is vinyl resin most important one in application of paints.The main absorption peak of acrylic resin to light is in outside solar spectrum scope.Therefore with the acrylate paint that it is made, there is photostabilization excellent especially and resistance to outdoor aging, not easily decompose under uviolizing or turn yellow, original gloss and color and luster can be kept for a long time, double bond in acrylate monomer is carbon-to-carbon structure through the macromolecular chain main chain that polyreaction generates, there is very strong heat and chemical stability, do not decompose at 170 DEG C, nondiscoloration, there is good acidproof alkali salt, staining and corrosive nature of the chemical such as grease and washing composition.Therefore acrylic resin paint is widely used in the fields such as aircraft, automobile, plant and instrument, building, household electrical appliances, road and bridge, weaving, food utensil.
Acrylic resin can prepare the coating of various form, is first to come out with solvent based coating, and along with the development of environment-friendly type coating, water-borne coatings, high solid coating, radiation curable coating, powder coating etc. become development trend.The solid content of traditional acrylate paint is lower, larger environmental pollution can be caused in volatilization process, research and development environment-friendly coating and application techniques, reduce the volatile organic compounds (VOC) in coating material production and construction, oneself becomes the center of domestic and international most of coating and resin design work.
Acroleic acid polyurethane coating is developed so far, and has become the class synthetic resin coating that in coating system, type at most, over-all properties is more complete, has had important use value and wide market outlook.Compared with traditional solvent-borne coating, high-solid level acrylate paint greatly reduces the content of organic volatile in coating system, save solidification energy consumption, saved coating material production and the solvent in using, reduced and pollute, some high solid coatings due to its workability and required execution conditions substantially identical with existing solvent based coating, existing preparation of construction can be utilized, and can match with existing coating system.Improving solid part of coating, to reduce volatile organic compound be the most direct method, can retain again lighter color in acroleic acid polyurethane coating performance simultaneously, protect that light tint retention is good, good weatherability, corrosion-resistant good feature.The solid part of improving coating just must use high solid low viscosity acrylic resin, and viscosity sharply raises along with the increase of solid part, therefore we introduce a kind of new monomer tertiary carbonic acid glycidyl ester (Cardura E-10) and synthesize high solid low viscosity acrylic resin.The present invention is exactly by this particular monomers of Cardura E-10, prepares a kind of high solid low viscosity acrylic resin by changing synthesis technology of acrylic.Although utilize Cardura E-10 to synthesize High solids Acrylic Resin have industry experience for many years, be still this resinoid first-selected modified monomer of synthesis at present.The Cardura E-10 of bibliographical information introduces technique following three kinds: 1. first Cardura E-10 and (methyl) vinylformic acid are prepared into prepolymer, and then with acrylic ester monomer Raolical polymerizable; 2. Cardura E-10 and vinylformic acid (ester) class monomer are mixed together dropping, carry out ring-opening reaction and Raolical polymerizable simultaneously; 3. Cardura E-10 is added low level flask together as a kind of reactive thinner solvent, then drip mix monomer and carry out Raolical polymerizable and ring-opening reaction.But there is main following shortcoming in existing three kinds of techniques: for technique 1. its technical disadvantages be that the prepolymer molecular weight prepared is comparatively large, when polyreaction below, presence bit inhibition effect, extends the production time; 2. and 3. the shortcoming that polymerization reaction time is long, polymericular weight is large, degree of branching is high is existed for technique.
Summary of the invention
The technical problem that the present invention mainly solves is to provide a kind of high solid low viscosity acrylic resin and preparation method thereof, shortens acrylic resin generated time, reduces production cost, and polymericular weight is less, degree of branching is low; Solve the problem that the high and resistance to acids and bases of conventional acrylic resin viscosity on market, water tolerance are bad simultaneously.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is: provide a kind of high solid low viscosity acrylic resin, it comprises the formula constituent of following weight part: N-BUTYL ACETATE 28-32 part, methacrylic acid 4-7 part, tertiary carbonic acid glycidyl ester 10-20 part, vinylbenzene 12-16 part, styrene dimer 0.2-2 part, initiator 1-2 part and acrylate 30-35 part.
In a preferred embodiment of the present invention, described acrylate comprises Isooctyl acrylate monomer, n-butyl acrylate, Hydroxyethyl acrylate and methyl methacrylate, and the weight proportion of described Isooctyl acrylate monomer, n-butyl acrylate, Hydroxyethyl acrylate and methyl methacrylate is 1:1-3.5:1-2:1-5.
In a preferred embodiment of the present invention, described initiator is organo-peroxide or azo-compound.
In a preferred embodiment of the present invention, described initiator is benzoyl peroxide, Diisopropyl azodicarboxylate, dicumyl peroxide, di-t-butyl peroxide, tertbutyl peroxide or isopropyl benzene hydroperoxide.
For solving the problems of the technologies described above, another technical solution used in the present invention is: provide a kind of high solid low viscosity acrylic resin preparation method, comprise the following steps:
(1) each component is taken according to weight proportion;
(2) first part's N-BUTYL ACETATE and first part's tertiary carbonic acid glycidyl ester mixing solutions are stirred intensification, insulation backflow 0.5-1h when temperature reaches 130-140 DEG C;
(3) mixture dripping first part's initiator, acrylate, vinylbenzene, styrene dimer and methacrylic acid carries out copolymerization, and time for adding controls at 2-3 h, is added dropwise to complete rear insulation 0.5-1.5h;
(4) mixing solutions of second section N-BUTYL ACETATE, second section initiator and second section tertiary carbonic acid glycidyl ester is added drop-wise at 20-40min complete, then is incubated 1-2h, cooling discharge, prepare high solid low viscosity acrylic resin.
In a preferred embodiment of the present invention, described first part's N-BUTYL ACETATE and the weight proportion of second section N-BUTYL ACETATE are 9:1.
In a preferred embodiment of the present invention, described first part's tertiary carbonic acid glycidyl ester and the weight proportion of second section tertiary carbonic acid glycidyl ester are 9:1.
In a preferred embodiment of the present invention, described first part's initiator and the weight proportion of second section initiator are 8:2.
The present invention prepares high solid low viscosity acrylic resin and adopts " starvation method " to drip synthesis." starvation method " drips synthesis is first the tertiary carbonic acid glycidyl ester mixing solutions of first part's N-BUTYL ACETATE and first part is added reactor to be warmed up to applicable temperature, then the mixture of initiator, acrylate, vinylbenzene, styrene dimer and methacrylic acid is dripped by header tank, the speed of telocopolymerization reaction can be carried out like this, to reach the object controlling high solid low viscosity acrylic resin molecular mass by the drop rate changing mixture; The change of reactor temperature can also be regulated simultaneously by the drop rate changing mixture, make the maximized object of efficiency of initiator to reach.
The copolyreaction of vinylformic acid (ester) monomer has the multiple methods such as mass polymerization, letex polymerization, solution polymerization, suspension polymerization.In step of the present invention, the synthesis of high solid low viscosity acrylic resin adopts solution method, and it is that vinylformic acid (ester) monomer is formed by Raolical polymerizable synthesis under solution state.Its advantage is that system viscosity is low and avoid gel effect; Be heated evenly, polymerization temperature easily controls; Be easy to the relative molecular mass and its distribution regulating product.
The hardness that step of the present invention provides resin to need using initiator, methyl methacrylate, vinylbenzene and styrene dimer as hard monomer; N-butyl acrylate and Isooctyl acrylate monomer regulate the second-order transition temperature of prepolymer as soft monomer; The functional group that methacrylic acid, Hydroxyethyl acrylate and tertiary carbonic acid glycidyl ester provide subsequent reactions to need as function monomer.Methyl methacrylate and vinylbenzene have very high second-order transition temperature, the hardness that resin can be provided to need, and make the high solid low viscosity acrylic resin prepared have excellent hardness.A large amount of water tolerance using the tertiary carbonic acid glycidyl ester with special construction to greatly improve this acrylic resin simultaneously.
Initiator of the present invention has two large classes: organo-peroxide and azo-compound, and there are very big difference different initiator efficiency of initiations and transformation period, usually wants experimental object and method to select suitable initiator.
Starting material of the present invention require strictly can not contain moisture content, will ensure the purity of monomer simultaneously.Moisture content in starting material can reduce the efficiency of initiator; The impure meeting of monomer makes the prepolymer of synthesis opaque, affects quality product.
Vinylformic acid of the present invention (ester) monomer requires purity >=99.5%, occurs turbid phenomenon to avoid the prepolymer synthesized.
Synthesis temperature of the present invention requires comparatively strict, and should control at 130-140 DEG C, temperature is too low, and the efficiency of initiation of initiator is not high, and obtained acrylic resin relative molecular mass is relatively large and cause viscosity too high; Temperature is too high, and half-lives of initiators is short, and utilization ratio is low, and the acrylic resin molecular weight of synthesis is relatively low, but residual monomer amount is larger.
Soaking time of the present invention requires comparatively strict, and soaking time should be strict controlled in 0.5-1h for the first time, ensures reflux stabilizes, discharges a small amount of moisture contained in solvent simultaneously; Second time soaking time should be strict controlled in 0.5-1.5h, ensures that (methyl) acrylic ester monomer can be polymerized completely; Soaking time should control at 1-2h for the third time, the tertiary carbonic acid glycidyl ester monomer energy complete reaction that guarantee drips below.
The invention has the beneficial effects as follows: present invention reduces acrylic resin generated time, reduce production cost, polymericular weight is less, degree of branching is low; And there is higher solid part, lower viscosity, excellent weathering resistance, rub resistance, ageing resistance, water tolerance, resistance to acids and bases, concrete advantage and result of use as follows:
1, higher solid part: solid part of this resin reaches 70%, higher than the acrylic resin of 60-65% solid part most on market;
2, lower viscosity: the viscosity of this resin at 3000-6000mPas, lower than acrylic resins most on market;
3, excellent mechanical property: sticking power, shock resistance, hardness, snappiness etc. are all good;
4, excellent workability: the same with other solvent based coatings after this resin lacquering, can adopt the various method construction such as brush, spray, leaching, roller;
5, stronger weathering resistance: expose experimental technique to the open air through natural climate according to GB/T 9276-1996, paint film not bubble, non-corrosive, do not ftracture, do not come off, endurance life reaches 5-10, longer than common acrylic resin;
6, superpower water tolerance, resistance to acids and bases: according to GB/T 9274-1988 through the measuring of resistant to liquid medium, 168h paint film not bubble, non-corrosive, do not ftracture, do not come off, higher than the standard of GB.We verify by experiment and draw, the general water tolerance of the acrylic resin that market exists is bad, and according to GB/T 9274-1988 through the measuring of resistant to liquid medium, after 168h, bubble, variable color appear in paint film, limit the use range of acrylic resin.
Embodiment
Be clearly and completely described to the technical scheme in the embodiment of the present invention below, obviously, described embodiment is only a part of embodiment of the present invention, instead of whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art, not making other embodiments all obtained under creative work prerequisite, belong to the scope of protection of the invention.
Embodiment 1
A kind of high solid low viscosity acrylic resin, it comprises the formula constituent of following weight part: N-BUTYL ACETATE 28 parts, methacrylic acid 4 parts, tertiary carbonic acid glycidyl ester 17 parts, vinylbenzene 13 parts, styrene dimer 2 parts, initiator 2 parts, methyl methacrylate 11 parts, Hydroxyethyl acrylate 10 parts, n-butyl acrylate 7 parts, Isooctyl acrylate monomer 6 parts.
The preparation method of this high solid low viscosity acrylic resin, specifically comprises the following steps:
(1) 25.2 parts of N-BUTYL ACETATEs and 15.3 parts of tertiary carbonic acid glycidyl ester mixing solutionss are stirred intensification, when temperature reaches 140 DEG C, be incubated backflow 0.5h;
(2) mixture dripping 1.6 parts of initiators, acrylate, vinylbenzene, styrene dimer and methacrylic acids carries out copolymerization, and time for adding controls at 2 h, is added dropwise to complete rear insulation 1h;
(3) mixing solutions of 2.8 parts of N-BUTYL ACETATEs, 0.4 part of initiator and 1.7 parts of tertiary carbonic acid glycidyl esters is added drop-wise at 30min complete, then is incubated 1.5h, cooling discharge, prepare high solid low viscosity acrylic resin.
Embodiment 2
A kind of high solid low viscosity acrylic resin, it comprises the formula constituent of following weight part: N-BUTYL ACETATE 30 parts, methacrylic acid 5 parts, tertiary carbonic acid glycidyl ester 11 parts, vinylbenzene 16 parts, styrene dimer 1 part, initiator 1 part, methyl methacrylate 12 parts, Hydroxyethyl acrylate 10 parts, n-butyl acrylate 10 parts, Isooctyl acrylate monomer 4 parts.
The preparation method of this high solid low viscosity acrylic resin, specifically comprises the following steps:
(1) 27 parts of N-BUTYL ACETATEs and 9.9 parts of tertiary carbonic acid glycidyl ester mixing solutionss are stirred intensification, when temperature reaches 130 DEG C, be incubated backflow 1h;
(2) mixture dripping 0.8 part of initiator, acrylate, vinylbenzene, styrene dimer and methacrylic acid carries out copolymerization, and time for adding controls at 2.5 h, is added dropwise to complete rear insulation 1.5h;
(3) mixing solutions of 3 parts of N-BUTYL ACETATEs, 0.2 part of initiator and 1.1 parts of tertiary carbonic acid glycidyl esters is added drop-wise at 20min complete, then is incubated 2h, cooling discharge, prepare high solid low viscosity acrylic resin.
Embodiment 3
A kind of high solid low viscosity acrylic resin, it comprises the formula constituent of following weight part: N-BUTYL ACETATE 32 parts, methacrylic acid 4 parts, tertiary carbonic acid glycidyl ester 13 parts, vinylbenzene 11 parts, styrene dimer 1 part, initiator 2 parts, methyl methacrylate 12 parts, Hydroxyethyl acrylate 11 parts, n-butyl acrylate 9 parts, Isooctyl acrylate monomer 5 parts.
The preparation method of this high solid low viscosity acrylic resin, specifically comprises the following steps:
(1) 28.8 parts of N-BUTYL ACETATEs and 11.7 parts of tertiary carbonic acid glycidyl ester mixing solutionss are stirred intensification, when temperature reaches 135 DEG C, be incubated backflow 0.7h;
(2) mixture dripping 1.6 parts of initiators, acrylate, vinylbenzene, styrene dimer and methacrylic acids carries out copolymerization, and time for adding controls at 3 h, is added dropwise to complete rear insulation 0.5h;
(3) mixing solutions of 3.2 parts of N-BUTYL ACETATEs, 0.4 part of initiator and 1.3 parts of tertiary carbonic acid glycidyl esters is added drop-wise at 40min complete, then is incubated 1h, cooling discharge, prepare high solid low viscosity acrylic resin.
The quantitative measurement result of the high solid low viscosity acrylic resin obtained by embodiment 1 ~ embodiment 3 is as shown in table 1.
Table 1
| Project | Technical indicator | Embodiment 1 | Embodiment 2 | Embodiment 3 | Detection method |
| Outward appearance | Micro-Huang is transparent | Micro-Huang is transparent | Micro-Huang is transparent | Micro-Huang is transparent | Range estimation |
| Gu containing/% | 69-71 | 71.8 | 70.3 | 69.4 | GB/T1725-2007 |
| Viscosity/mPas(25 DEG C) | 3000-6000 | 5500 | 5200 | 4900 | GB/T1723-1993 |
| Acid number/mgKOHg -1 | 3-8 | 7.11 | 7.67 | 7.08 | GB/T6743-2008 |
Test example
By the high solid low viscosity acrylic resin obtained by embodiment 1 ~ embodiment 3 and HDI tripolymer in n(-OH): the ratio of n(-NCO)=1:1.05 mixes and adds appropriate amount of addition agent prepares varnish, then be diluted to spray viscosity with the N-BUTYL ACETATE of 10-15%, finally adopt the making sheet of aerial spraying mode.The part by weight of each material is the high solid low viscosity acrylic resin obtained by embodiment 1 ~ embodiment 3 70.1 parts, HDI trimer curing agent 19.7 parts, defoamer TECH-367 0.1 part; Flow agent BYK-300 0.1 part, N-BUTYL ACETATE 10 parts.Sample making condition: the tinplate of appearance of film, time of drying, sticking power, shock strength, resistance to bending, pencil hardness test employing 50 × 120 × 0.1-0.2mm, with 0# sand papering rust cleaning and tin coating, film thickness 23 ± 3 μm, maintenance 48h; The sandblasting steel plate of resistant to liquid medium test employing 70 × 120 × 0.8-1.5mm, supporting paint film is epoxy zinc-rich 50 μm, epoxy intermediate coat 80 μm, 50 μm, embodiment varnish, paint film total thickness 180 ± 10 μm, maintenance 7 days.The performance test experimental result of the paint film of preparation is as shown in table 2.
Table 2
| Project | Embodiment 1 | Embodiment 2 | Embodiment 3 | Detection method |
| Paint viscosity (mPas) | 3800 | 3500 | 3400 | GB/T1723-1993 |
| Appearance of film | Flat smooth | Flat smooth | Flat smooth | Range estimation |
| Surface drying time (25 DEG C, min) | 40 | 40 | 40 | GB/T1728-1989 |
| Do solid work the time (25 DEG C, h) | 20 | 20 | 20 | GB/T1728-1989 |
| Sticking power (drawing lattice, level) | 1 | 1 | 1 | GB/T9286-1998 |
| Shock strength (cm) | 50 | 50 | 50 | GB/T1732-1993 |
| Resistance to bending (mm) | 2 | 2 | 2 | GB/T6742-2007 |
| Pencil hardness | H | H | H | GB/T6739-2006 |
| Water tolerance (25 DEG C, 336h) | Peel off without bubbling, without getting rusty | Peel off without bubbling, without getting rusty | Peel off without bubbling, without getting rusty | GB/T5209-1985 |
| Acid resistance (5% H 2SO 4，168h) | Peel off without bubbling, without getting rusty | Peel off without bubbling, without getting rusty | Peel off without bubbling, without getting rusty | GB/T9274-1988 |
| Alkali resistance (5% NaOH, 168h) | Peel off without bubbling, without getting rusty | Peel off without bubbling, without getting rusty | Peel off without bubbling, without getting rusty | GB/T9274-1988 |
Present invention reduces acrylic resin generated time, reduce production cost, polymericular weight is less, degree of branching is low; And there is higher solid part, lower viscosity, excellent weathering resistance, rub resistance, ageing resistance, water tolerance, resistance to acids and bases, concrete advantage and result of use as follows: solid part that (1) is higher: solid part of this resin reaches 70%, higher than the acrylic resin of 60-65% solid part most on market; (2) lower viscosity: the viscosity of this resin at 3000-6000mPas, lower than acrylic resins most on market; (3) excellent mechanical property: sticking power, shock resistance, hardness, snappiness etc. are all good; (4) excellent workability: the same with other solvent based coatings after this resin lacquering, can adopt the various method construction such as brush, spray, leaching, roller; (5) stronger weathering resistance: expose experimental technique to the open air through natural climate according to GB/T 9276-1996, paint film not bubble, non-corrosive, do not ftracture, do not come off, endurance life reaches 5-10, longer than common acrylic resin; (6) superpower water tolerance, resistance to acids and bases: according to GB/T 9274-1988 through the measuring of resistant to liquid medium, 168h paint film not bubble, non-corrosive, do not ftracture, do not come off, higher than the standard of GB.We verify by experiment and draw, the general water tolerance of the acrylic resin that market exists is bad, and according to GB/T 9274-1988 through the measuring of resistant to liquid medium, after 168h, bubble, variable color appear in paint film, limit the use range of acrylic resin.
The foregoing is only embodiments of the invention; not thereby the scope of the claims of the present invention is limited; every utilize description of the present invention to do equivalent structure or equivalent flow process conversion; or be directly or indirectly used in other relevant technical field, be all in like manner included in scope of patent protection of the present invention.
Claims (8)
1. a high solid low viscosity acrylic resin, it is characterized in that, it comprises the formula constituent of following weight part: N-BUTYL ACETATE 28-32 part, methacrylic acid 4-7 part, tertiary carbonic acid glycidyl ester 10-20 part, vinylbenzene 12-16 part, styrene dimer 0.2-2 part, initiator 1-2 part and acrylate 30-35 part.
2. high solid low viscosity acrylic resin according to claim 1, it is characterized in that, described acrylate comprises Isooctyl acrylate monomer, n-butyl acrylate, Hydroxyethyl acrylate and methyl methacrylate, and the weight proportion of described Isooctyl acrylate monomer, n-butyl acrylate, Hydroxyethyl acrylate and methyl methacrylate is 1:1-3.5:1-2:1-5.
3. high solid low viscosity acrylic resin according to claim 1, is characterized in that, described initiator is organo-peroxide or azo-compound.
4. high solid low viscosity acrylic resin according to claim 3, is characterized in that, described initiator is benzoyl peroxide, Diisopropyl azodicarboxylate, dicumyl peroxide, di-t-butyl peroxide, tertbutyl peroxide or isopropyl benzene hydroperoxide.
5. high solid low viscosity acrylic resin according to claim 1 preparation method, it is characterized in that, comprise the following steps:
(1) each component is taken according to weight proportion;
(2) first part's N-BUTYL ACETATE and first part's tertiary carbonic acid glycidyl ester mixing solutions are stirred intensification, insulation backflow 0.5-1h when temperature reaches 130-140 DEG C;
(3) mixture dripping first part's initiator, acrylate, vinylbenzene, styrene dimer and methacrylic acid carries out copolymerization, and time for adding controls at 2-3 h, is added dropwise to complete rear insulation 0.5-1.5h;
(4) mixing solutions of second section N-BUTYL ACETATE, second section initiator and second section tertiary carbonic acid glycidyl ester is added drop-wise at 20-40min complete, then is incubated 1-2h, cooling discharge, prepare high solid low viscosity acrylic resin.
6. high solid low viscosity acrylic resin according to claim 5 preparation method, it is characterized in that, described first part's N-BUTYL ACETATE and the weight proportion of second section N-BUTYL ACETATE are 9:1.
7. high solid low viscosity acrylic resin according to claim 5 preparation method, it is characterized in that, described first part's tertiary carbonic acid glycidyl ester and the weight proportion of second section tertiary carbonic acid glycidyl ester are 9:1.
8. high solid low viscosity acrylic resin according to claim 5 preparation method, it is characterized in that, described first part's initiator and the weight proportion of second section initiator are 8:2.
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| CN111286241B (en) * | 2020-03-20 | 2021-09-21 | 立邦工业涂料(上海)有限公司 | Acrylic resin coating with integrated bottom and top and preparation method thereof |
| CN111925475A (en) * | 2020-08-31 | 2020-11-13 | 江苏三木化工股份有限公司 | Pure acrylic ester capable of realizing photopolymerization and preparation method thereof |
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