CN101709196A - Light mixing cured coating composition and preparation method thereof - Google Patents
Light mixing cured coating composition and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a light mixing cured coating composition which comprises epoxy acrylic acid monoester, ultraviolet light-heat mixing curing agent or ultraviolet light free radical-cation mixing curing agent, pigmented filler, reactive diluent, dispersing agent, defoaming agent and flatting agent. The invention also discloses a preparation method of the light mixing cured coating composition. The coating composition of the invention has small cure shrinkage and high bonding strength, can be applied to dark systems, can be used for coating some components with complicated structures, and can be used for coating surfaces of wood products, plastics, metals and the like by the construction methods of brush coating, spray coating, curtain coating, roller coating and the like.
Description
Technical field
The invention belongs to photo-cured coating and fabricating technology field thereof, especially relate to a kind of coating material solidified and preparation technology of mixed light who is widely used in the application on surfaces such as woodenware, plastics, metal.
Background technology
UV-light (UV) curing technology is a kind of environmental type technology without solvent, it have curing speed fast (0.1-10s), low in the pollution of the environment, energy expenditure is low, can automatic production, be suitable for use in the first-class advantage of heat-sensitive substrate material.Enter after the nineties in 20th century; the protection environment has become the topic of people's common concern with save energy; the corresponding rules of the numerous and confused formulation in countries in the world, the quantity discharged of restriction volatile organic compounds (VOC) is strengthened trade management; therefore; traditional solvent based coating is too big because of its organic volatile composition, and environmental pollution is serious, and its market share is dwindled just rapidly; ultraviolet-curing paint with environmental protection characteristic then develops rapidly, and becomes the forward position research topic of coating circle.In China, ultraviolet-curing paint progressively replaces traditional solvent based coating and is used widely on timber, metal, plastics, paper, leather.
UV-curing technology is divided by mechanism radically curing and cationic curing, the radically curing system have curing speed fast (≤10s), the advantage that performance is easy to regulate, moisture resistance is wet, initiator type is many, but also have oxygen inhibition, the polymerization volumetric shrinkage is big, precision is not high, poor adhesive force, problems such as solidification without male offspring.Most of in the market photocuring product (as ultraviolet-curing paint, printing ink and tackiness agent etc.) all is a radical-curable, and used oligopolymer normally contains the resin of C=C unsaturated double-bond, for example unsaturated polyester, acrylate etc.The cationic curing system has that volumetric shrinkage is little, strong adhesion, wear-resisting and hardness advantages of higher, and after UV-light is withdrawn, its curing reaction can also be proceeded, there is after fixing, but it is slow that it has curing speed, oligopolymer and reactive thinner kind are few, and price height and cured product are difficult for shortcomings such as adjusting, thereby have limited its practical application.With the film forming oligomer of cationic cure mechanism, come across the latter stage eighties, as vinyl mystery series and epoxy series.Vinyl mystery oligopolymer can obtain with hydroxyl ethene mystery and corresponding resin reaction; The epoxies oligopolymer mainly contains epoxidation bisphenol a resin, epoxidation silicone resin etc., wherein the most frequently used is the epoxidation bisphenol a resin, its viscosity is higher, polymerization velocity is slower, general and fast than low viscosity, rate of polymerization aliphatic epoxy resin is used, and the cationic curing system is mainly used in the dark coating or ink system.Wherein, the free radical ultraviolet light polymerization also exists and is vulnerable to the oxygen inhibition effect, is not easy the defective of surface drying.
Summary of the invention
One of purpose of the present invention is to provide a kind of UV-light mixing cured coating composition, existing UV-light radically curing group in the same molecular resin in the composition (the two keys of C=C) but the group (epoxide group) of UV-light cationic curing or thermofixation is arranged again, can be mixing cured by different curing modes, solve the defective that prior art exists.
For achieving the above object, the present invention adopts following technical scheme:
The mixing cured coating composition of a kind of UV-light comprises following component and percentage composition thereof:
Propylene oxide acid monoester 30～60
Reactive thinner 20～50
Ultraviolet-heat mixed curing agent or UV-light free radical-positively charged ion mixed curing agent 1～10
Color stuffing 5～30
Dispersion agent 0～2
Defoamer 0～1
Flow agent 0～2
Preferred scheme is: comprise following component and percentage composition thereof:
Propylene oxide acid monoester 50
Reactive thinner 30
Ultraviolet-heat mixed curing agent or UV-light free radical-positively charged ion mixed curing agent 4
Color stuffing 14
Dispersion agent 0.5
Defoamer 0.5
Flow agent 1
More preferred scheme is: described propylene oxide acid monoester is one or both or three kinds or the four kinds of mixtures in bisphenol-A epoxy acrylic monoester, brominated bisphenol A propylene oxide acid monoester, polyalcohol modified propylene oxide acid monoester, the fatty acid modified propylene oxide acid monoester.
More preferred scheme is: described reactive thinner is the mixture of monofunctional diluent or bifunctional thinner or trifunctional thinner or monofunctional diluent and bifunctional thinner or mixture or the mixture of bifunctional thinner and trifunctional thinner or the mixture of monofunctional diluent and bifunctional thinner and trifunctional thinner of monofunctional diluent and trifunctional thinner; Described monofunctional diluent is: glycidyl acrylate, butyl acrylate, methyl acrylate, Hydroxyethyl acrylate, Propylene glycol monoacrylate, N-ethene pyrrole alkane ketone; The bifunctional thinner is: PDDA, phthalic acid tripropylene glycol diacrylate, propylene glycol diacrylate, tripropylene glycol diacrylate, neopentylglycol diacrylate, ethoxylated neopentylglycol diacrylate, 1,6-hexanediyl ester, 1,4 butanediol diacrylate, ethoxylated bisphenol a diacrylate, diethylene glycol diacrylate or triethylene glycol diacrylate; The trifunctional thinner is: Viscoat 295, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate or propoxylated glycerol triacrylate etc.
More preferred scheme is: described color stuffing is one or more mixtures such as titanium dioxide, zinc sulfide white, lime carbonate, calcium sulfate, wollastonite, barium sulfate, silicon-dioxide, talcum powder, chrome yellow, chrome green, iron oxide red, barba hispanica, red lead, zinc-chrome yellow, phthalocyanine blue.
More preferred scheme is: described dispersion agent is one or more the mixture among EFKA4050, EFKA4010, CFC510, the CFC637; Described flow agent is a ultraviolet-curing paint specialty flow agent, is one or more the mixture among EFKA3883, EFKA3886, the EFKA3600; Described defoamer is one or more the mixture among EFKA2022, EFKA2040, the BYK052.
More preferred scheme is: described initiator is that one or both of ultraviolet initiator mix with one or both of thermal initiator, and wherein ultraviolet initiator comprises: st-yrax and derivative thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone, Darocur1173 etc.; Thermal initiator comprises quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, diethylaminopropylamine, modified amine, aromatic amine, Tetra hydro Phthalic anhydride, benzophenone (BP)/tertiary amine etc.
More preferred scheme is: described initiator is that one or both of UV-light radical initiator mix with one or both of UV-light cationic initiator, and wherein free radical photo-initiation has: st-yrax and derivative thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone etc.; Cation light initiator has: diaryl iodine compound and triaryl sulphur compound etc.
Another object of the present invention is to provide the preparation technology of a kind of ultraviolet-heat mixed curing agent or the mixing cured coating composition of UV-light free radical-positively charged ion, comprise the steps:
1) preparation of basic slurry: the described light mixing cured coating composition basic components of each technical scheme of last goal of the invention is mixed, and disperse with high speed dispersor;
2) preparation of mixing cured coating: the ultraviolet-heat mixed curing agent or the UV-light free radical-positively charged ion mixed curing agent that add quality % mark 1-10 in the basic slurry for preparing, in the 500ml there-necked flask, add a certain amount of Resins, epoxy, stir, oil bath is to certain temperature, add catalyst n then, N-dimethyl benzylamine (BDMA) or N, the N-diethyl benzylamine, the stopper MEHQ, the vinylformic acid of metering, take a sample every 30min, with the sodium hydroxide titration of 0.1mol/L, the transformation efficiency of carboxylic acid in the acid number of counting system and the reaction process, when the acid number in the reaction system during less than 3mgKOH/g, think that promptly esterification finishes, be after the cooling can be mixing cured resin.
Preferred scheme is: wherein the preparation method of composition propylene oxide acid monoester is: is to mix at 2: 1 Resins, epoxy and vinylformic acid by the massfraction ratio, the catalyst n of adding 0.1%, N-dimethyl benzylamine or N, N-diethyl benzylamine and 0.1% stopper p-methyl anisole, at 100 ℃ of reaction 4-7h, with the sodium hydroxide titration of 0.1mol/L, when the acid number in the reaction system during less than 3mgKOH/g, think that promptly esterification finishes, be after the cooling can be mixing cured resin.
Benzene is invented described coating composition can adopt the construction of methods such as brushing, spraying, showering, roller coating, is used for the application on surfaces such as woodenware, plastics, metal, film forming after mixing cured.After mixing cured, room temperature is placed 1 day test performance.
The present invention compared with prior art has following advantage and beneficial effect:
The mixing cured coating composition of UV-light of the present invention, existing UV-light radically curing group in the same molecular resin in the composition (the two keys of C=C) but the group (epoxide group) of UV-light cationic curing or thermofixation is arranged again, it is mixing cured to pass through different curing modes.Adopt mixing cured mode, can utilize the characteristics of free radical type ultraviolet light fast solidification, make coating reach at short notice surface drying (≤10s), and certain bonding strength arranged, with thermofixation or UV-light positively charged ion (after UV-light withdraws, the free radical type ultraviolet light polymerization stops at once, cation type ultraviolet photo-curing also can be proceeded) carry out after fixing, the physicochemical properties such as bonding strength of coating are further improved, and the curing groups of two kinds of curing modes is in same molecular resin, than carrying out mixing cured system more excellent performance after two kinds of mixed with resin.
For synthesizing of resin, the present invention is in certain condition and vinylformic acid generation esterification with Resins, epoxy, by gate ring oxygen groups and acrylic acid proportioning, can make the most molecular resins in reaction back is that an end has epoxide group (thermofixation group or UV-light cationic curing group), the other end is acrylic double bond group (a UV-light radically curing group), the two ends of other minute quantity all are that the molecule of acrylic double bond or epoxide group also can solidify in after fixing, and the performance of coating is not had big influence.Auxiliary agents such as synthetic resin and reactive thinner, color stuffing, dispersion agent, defoamer are uniformly dispersed, add free radical-cation light initiator or free radical photo-initiation-thermofixation initiator and stir, just can obtain at the mixing cured coating of UV-light.
The mixing cured coating of Pei Zhi UV-light acrylic double bond under UV-irradiation passes through the radical form fast setting as stated above, make coating reach surface drying substantially, and certain bonding strength arranged, as take the cation type ultraviolet photo after fixing, then UV-light causes the radical-cured epoxide group cationoid polymerisation that causes simultaneously and can also continue curing after UV-irradiation is withdrawn, the coating cross-linking density is further improved, and physicochemical property strengthens; As when adopting thermofixation to carry out after fixing, behind the UV-light radically curing, carry out thermofixation by heating and the mode of insulation for some time, also can improve the physicochemical property and the bonding strength of coating.This be because, the UV-light radically curing of acrylic double bond, it is big that it solidifies volumetric shrinkage, bonding strength is generally not high, and cured thickness also is subjected to illumination effect and considerable restraint is arranged, general pure its coating thickness of free radical ultraviolet light polymerization system is all little, also be not suitable in the pure radically curing mode of coloured or dark system, then what caused is the ring-opening polymerization of epoxide group in the resin to curing mode (thermofixation or UV-light cationic curing), in the coating of thick coating or dark color, also can cause curing, and it is solidified with some volume compensation effects, it is little to solidify volumetric shrinkage, therefore adopt mixing cured mode can improve the bonding physicochemical property that waits of coating, and also highly beneficial to the curing of the coating of thicker coating and dark color.Have two kinds of curing groups in the molecular resin simultaneously, also can solve several mixed with resin compound system unstable properties, local solidification is inhomogeneous and two kinds of problems such as oligopolymer intermiscibility, can effectively improve the performance of the mixing cured coating of UV-light.
The mixing cured coating of UV-light of the present invention can be applicable to plastics, timber, external coatings such as metal: as make varnish, adopt free radical-positively charged ion mixing ultraviolet light polymerization, because it has than the lower cure shrinkage of pure free radical ultraviolet light polymerization system, higher bonding strength, so can be used for plastics, the application on low surface energy surfaces such as metal, adopt the mixing cured system of ultraviolet-heat, then be adapted to the application of some different in nature devices (non-single plane parts), insufficient or the uneven situations of position illumination such as the parts turning then coating of available this mixing cured system are carried out application, can guarantee that coating is mixing cured relative down the curing evenly of light-Re.As make colored paint, available two kinds of mixing cured modes are applied to the application on surfaces such as plastics, timber, metal.
Embodiment
Below in conjunction with specific embodiment the present invention is described in further details.
Embodiment 1:
The component and the weight proportion of coating of the present invention are as follows:
55 parts of bisphenol-A epoxy acrylic monoesters
5 parts of glycidyl acrylates
10 parts of butyl acrylates
5 parts of Viscoat 295s (TMPTA)
15 parts of tripropylene glycol diacrylates (TPGDA)
3 parts of Darocur1173
2 parts of triaryl sulphur compounds
5 parts of titanium dioxides
At first glycidyl acrylate, butyl acrylate, Viscoat 295 (TMPTA) and tripropylene glycol diacrylate (TPGDA) etc. are added in the stirred pot by above-mentioned weight proportion, the normal temperature high-speed stirring is even, the propylene oxide acid monoester that adds metering then, stir, add free radical photo-initiation Darocur1173 and cation light initiator triaryl sulphur compound at last, the after-filtration that stirs is packaged as coating.
Coating can adopt method constructions such as brushing, spraying, showering, after adopting UV-light free radical-positively charged ion mixing cured, detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.83, wear resistance (750g/50r) 0.011g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Embodiment 2:
The component and the weight proportion of coating of the present invention are as follows:
50 parts of bisphenol-A epoxy acrylic monoesters
5 parts of glycidyl acrylates
10 parts of butyl methacrylate
5 parts of Viscoat 295s (TMPTA)
10 parts of 1,6 hexanediol diacrylates (HDDA)
10 parts of tripropylene glycol diacrylates (TPGDA)
2 parts of Irgacure184
3 parts of triethylene tetramines
5 parts of titanium dioxides
The preparation method of coating is with embodiment 1.
Coating can adopt method constructions such as brushing, spraying, showering, after adopting UV-light free radical-Re mixing cured, detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.86, wear resistance (750g/50r) 0.009g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Embodiment 3:
The component and the weight proportion of coating of the present invention are as follows:
50 parts of brominated bisphenol A propylene oxide acid monoesters
5 parts of Hydroxyethyl acrylates
5 parts of glycidyl methacrylate
10 parts of pentaerythritol triacrylates (PETA)
5 parts of 1,4 butanediol diacrylates (BDDA)
5 parts of ethoxylations (4)-bisphenol a diacrylate (EO-BPDA)
10 parts of titanium dioxides
2 parts of phthalocyanine blues
2 parts of silicon-dioxide
2 parts of benzophenone (BP)/tertiary amine
2 parts of diaryl iodine compounds
0.5 part of EFKA4050
1 part of EFKA3600
0.5 part of EFKA2040
The preparation method of coating is with embodiment 1.
Coating can adopt method constructions such as brushing, spraying, showering, with UV-light free radical-positively charged ion mixing cured after, detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.79, wear resistance (750g/50r) 0.012g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Embodiment 4:
The component and the weight proportion of coating of the present invention are as follows:
45 parts of aliphatic epoxy acrylic monoesters
5 parts of butyl acrylates
5 parts of glycidyl methacrylate
10 parts of ethoxylation (3) Viscoat 295s (EO-TMPTA)
5 parts of diethylene glycol diacrylates (DGDA)
10 parts of propylene glycol diacrylates (DPGDA)
5 parts of titanium dioxides
5 parts in lime carbonate
2 parts of chrome yellow
2 parts of Darocur1173
4 parts of diethylaminopropylamines
0.5 part of EFKA4050
1 part of EFKA3600
0.5 part of EFKA2040
The preparation method of coating is with embodiment 1.
Coating can adopt method constructions such as brushing, spraying, showering, after adopting UV-light free radical-Re mixing cured, detect 1 grade of 1 grade of ADHESION OF PAINTS power of the present invention (cross-hatching), hardness (pendulum-rocker hardness) 0.75, wear resistance (750g/50r) 0.015g, dry heat resistance (90 ± 2 ℃), good alcohol resistance and water tolerance are arranged.
Above content be in conjunction with concrete preferred implementation to further describing that the present invention did, can not assert that concrete enforcement of the present invention is confined to these explanations.For the general technical staff of the technical field of the invention, without departing from the inventive concept of the premise, can also make some simple deduction or replace, all should be considered as belonging to protection scope of the present invention.
Claims (10)
1. light mixing cured coating composition is characterized in that: comprise following component and percentage composition thereof:
Propylene oxide acid monoester 30～60
Reactive thinner 20～50
Ultraviolet-heat mixed curing agent or UV-light free radical-positively charged ion mixed curing agent 1～10
Color stuffing 5～30
Dispersion agent 0～2
Defoamer 0～1
Flow agent 0～2.
2. light mixing cured coating composition as claimed in claim 1 is characterized in that: comprise following component and percentage composition thereof:
Propylene oxide acid monoester 50
Reactive thinner 30
Ultraviolet-heat mixed curing agent or UV-light free radical-positively charged ion mixed curing agent 4
Color stuffing 14
Dispersion agent 0.5
Defoamer 0.5
Flow agent 1.
3. as claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described propylene oxide acid monoester is one or both or three kinds or the four kinds of mixtures in bisphenol-A epoxy acrylic monoester, brominated bisphenol A propylene oxide acid monoester, polyalcohol modified propylene oxide acid monoester, the fatty acid modified propylene oxide acid monoester.
4. light mixing cured coating composition as claimed in claim 3 is characterized in that: described reactive thinner is the mixture of monofunctional diluent or bifunctional thinner or trifunctional thinner or monofunctional diluent and bifunctional thinner or mixture or the mixture of bifunctional thinner and trifunctional thinner or the mixture of monofunctional diluent and bifunctional thinner and trifunctional thinner of monofunctional diluent and trifunctional thinner; Described monofunctional diluent is: glycidyl acrylate, butyl acrylate, methyl acrylate, Hydroxyethyl acrylate, Propylene glycol monoacrylate, N-ethene pyrrole alkane ketone; The bifunctional thinner is: PDDA, phthalic acid tripropylene glycol diacrylate, propylene glycol diacrylate, tripropylene glycol diacrylate, neopentylglycol diacrylate, ethoxylated neopentylglycol diacrylate, 1,6-hexanediyl ester, 1,4 butanediol diacrylate, ethoxylated bisphenol a diacrylate, diethylene glycol diacrylate or triethylene glycol diacrylate; The trifunctional thinner is: Viscoat 295, ethoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate or propoxylated glycerol triacrylate.
5. as claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described color stuffing is titanium dioxide, zinc sulfide white, lime carbonate, calcium sulfate, wollastonite, barium sulfate, silicon-dioxide, talcum powder, chrome yellow, chrome green, iron oxide red, barba hispanica, red lead, zinc-chrome yellow, one or more mixtures of phthalocyanine blue.
6. as claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described dispersion agent is one or more the mixture among EFKA4050, EFKA4010, CFC510, the CFC637; Described flow agent is a ultraviolet-curing paint specialty flow agent, is one or more the mixture among EFKA3883, EFKA3886, the EFKA3600; Described defoamer is one or more the mixture among EFKA2022, EFKA2040, the BYK052.
7. as claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described initiator is that one or both of ultraviolet initiator mix with one or both of thermal initiator, and wherein ultraviolet initiator comprises: st-yrax and derivative thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone, Darocur1173; Thermal initiator comprises quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, diethylaminopropylamine, modified amine, aromatic amine, Tetra hydro Phthalic anhydride, benzophenone/tertiary amine.
8. as claim 1 or 2 described light mixing cured coating compositions, it is characterized in that: described initiator is that one or both of UV-light radical initiator mix with one or both of UV-light cationic initiator, and wherein free radical photo-initiation has: st-yrax and derivative thereof and acetophenone derivs: benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, dialkoxy methyl phenyl ketone and chloroacetophenone etc.; Cation light initiator has: diaryl iodine compound and triaryl sulphur compound.
9. the preparation method of a light mixing cured coating composition: comprise the steps:
1) preparation of basic slurry: each described light mixing cured coating composition basic components of claim 4～8 is mixed, and disperse with high speed dispersor;
2) preparation of mixing cured coating: the ultraviolet-heat mixed curing agent or the UV-light free radical-positively charged ion mixed curing agent that add quality % mark 1-10 in the basic slurry for preparing, stir and promptly get mixing cured coating, coating adopts brushes, or spraying, or showering, or the method for roller coating construction, be used for the application on surfaces such as woodenware, plastics, metal, film forming after mixing cured.
10. the preparation method of light mixing cured coating composition as claimed in claim 9: wherein the preparation method of composition propylene oxide acid monoester is: is to mix at 2: 1 Resins, epoxy and vinylformic acid by the massfraction ratio, the catalyst n of adding 0.1%, N-dimethyl benzylamine or N, N-diethyl benzylamine and 0.1% stopper p-methyl anisole, at 100 ℃ of reaction 4-7h, sodium hydroxide titration with 0.1mol/L, when the acid number in the reaction system during less than 3mg KOH/g, think that promptly esterification finishes, be after the cooling can be mixing cured resin.
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