CN104962130B - Heat-resistant yellow-stain-resistant epoxy acrylate low polymer and preparation method of UV (ultraviolet) ink - Google Patents
Heat-resistant yellow-stain-resistant epoxy acrylate low polymer and preparation method of UV (ultraviolet) ink Download PDFInfo
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Abstract
The invention discloses a heat-resistant yellow-stain-resistant epoxy acrylate low polymer and a preparation method of UV (ultraviolet) ink. The heat-resistant yellow-stain-resistant epoxy acrylate low polymer is prepared through a following method comprising the following steps of carrying out an addition-esterification reaction on triglycidyl isocyanurate and an acrylic organic acid under the action of a catalyst, so as to obtain triglycidyl isocyanurate acrylate, then reacting the triglycidyl isocyanurate acrylate with an acid anhydride to obtain an acid anhydride modified triglycidyl isocyanurate acrylate, finally, adding a viscosity reducer and a reactive thinning agent into the acid anhydride modified triglycidyl isocyanurate acrylate, and regulating system viscosity to obtain the heat-resistant yellow-stain-resistant epoxy acrylate low polymer. The heat-resistant yellow-stain-resistant epoxy acrylate low polymer is adopted for the UV ink prepared by the invention; the defect that conventional UV ink is easy to yellow is overcome; moreover the UV ink is high in adhesive force, is wide in the serviceable range to base materials, and can be printed on the upper surfaces of base materials of PE (polyethylene), PP (polypropylene), PET (polyethylene terephthalate), glass, a circuit board and the like in a screen printing manner. The UV ink prepared by the invention has high glossiness, excellent heat resistance and yellow stain resistance, and is further wide in application range.
Description
Technical field
The present invention relates to ink area, and in particular to a kind of synthesis of heat-resisting color inhibition epoxy acrylate oligomer and its
Application in UV ink.
Background technology
Ultraviolet light (UV) solidification refers to that under action of ultraviolet light the photoactive substance in system occurs chemical reaction and produces activity
Fragment, the polymerization of activated monomer or oligomer, crosslinking in initiator system, so that system has liquid coating moment to become solid-state painting
Layer.From Bayer A.G in 1967 develop first generation UV it is coating material solidified since, UV curing technologies are worldwide obtained
Develop rapidly, essentially consist in：Its quick solidifying, caters to the needs of modern production automatically；It is pollution-free, comply with modern coatings, ink
Developing direction；Film quality height, hardness height, damage resistant, it is corrosion-resistant the advantages of and enjoy people to pay close attention to.
UV is coating material solidified to be mainly made up of light trigger, photoactive monomer, photoactive oligomers etc..Wherein photolytic activity is oligomeric
Thing constitutes the skeleton of cured film cross-linked structure, is the master of UV ink physicochemical properties equivalent to the resin in common ink
Want determiner.With common ink resin except that, the oligomer in UV ink in structure must have can light consolidate
The group of change, belongs to photoresist.
Epocryl（Epoxy acrylate,EA）It is that most widely used class light is consolidated in UV solidifications field
Change resin, it has the advantages that curing rate is fast, adhesive strength is big, hardness is high, glossiness is high and chemical proofing.But EA
Viscosity it is very high, yellowing resistance is poor, and its solidfied material crosslink density is big, in tridimensional network, as a result causes fragility big, tough
Property is poor, and its combination property is reduced to a great extent.To solve the above problems, prior art is mainly from epoxy acrylate
Modified aspect is studied, and such as epoxy acrylate is modified using organic acid, can prepare the good EA of pliability；Utilize
Polyurethane is modified to epoxy acrylate, can also improve the pliability of resin；Using organic silicon modified epoxy acrylate
Can obtain with resin that heat stability is high, pliability is good etc..Although these technologies are improving the soft of epoxy acrylate
Property, heat stability aspect accomplished gratifying result, but modified epoxy acrylate in hardness, chemicals-resistant really
The aspects such as property have but declined, and cannot still solve the problems, such as that its yellowing resistance is poor.Therefore, need badly and seek a kind of heat-resisting resistance to
Xanthochromia, chemicals-resistant, the Epocryl of high glaze.
The content of the invention
It is an object of the invention to overcome the deficiencies in the prior art, there is provided a kind of heat-resisting color inhibition epoxyacrylate oligomers
Thing.
Another object of the present invention is to provide above-mentioned heat-resisting color inhibition epoxy acrylate oligomer in UV ink
Using.
It is a further object of the present invention to provide the preparation method of the UV ink of above-mentioned heat-resisting color inhibition.
To achieve these goals, the present invention is adopted the following technical scheme that：A kind of heat-resisting color inhibition epoxy acrylate is low
Polymers, makes by the following method：By triglycidyl isocyanurate（TGIC）, acrylic compounds organic acid occurs under catalyst
Addition esterification, obtains isocyanuric acid three-glycidyl acrylate, then obtains anhydride modified isocyanide urea with anhydride reaction
Sour three-glycidyl acrylate, is eventually adding thinner and reactive diluent, and regulation system viscosity is obtained final product.
Preferably, in above-mentioned heat-resisting color inhibition epoxy acrylate oligomer, triglycidyl isocyanurate and third
Alkene classes of organic acids, the mol ratio of anhydride are 1.0：（2.8～3.2）：2.0；The amount of catalyst accounts for isocyanuric acid three-glycidyl
The 0.6% of ester and acrylic compounds organic acid gross weight；The addition of the thinner accounts for the 33～45% of reactant gross weight；It is described
The addition of reactive diluent accounts for the 10～15% of reactant gross weight.
The heat-resisting color inhibition epoxy acrylate oligomer that the present invention is provided is raw material using TGIC, by a series of anti-
Anhydride modified isocyanuric acid three-glycidyl acrylate should be obtained, the resin is uV curable and has certain alkali solubility
Oligomer, with heat-resisting, color inhibition and the characteristics of high glaze.
Preferably, in above-mentioned heat-resisting color inhibition epoxy acrylate oligomer, described acrylic compounds organic acid is third
Olefin(e) acid（AA）, one or more mixture in methacrylic acid.
Preferably, in above-mentioned heat-resisting color inhibition epoxy acrylate oligomer, described anhydride is HHPA
（HHPA）, maleic anhydride（MA）, trimellitic anhydride（TMA）In one or more mixture.
Preferably, in above-mentioned heat-resisting color inhibition epoxy acrylate oligomer, described catalyst be toluene sulfonic acide,
Phosphoric acid, triethylamine, N, one or more mixture in N- dimethyl cyclohexyl amines, triethanolamine.
Preferably, in above-mentioned heat-resisting color inhibition epoxy acrylate oligomer, described thinner is toluene, acetic acid second
One or more mixture in ester, acetone.
Preferably, in above-mentioned heat-resisting color inhibition epoxy acrylate oligomer, described reactive diluent is phenyl contracting
Water glycerin ether, Ethylene glycol diglycidyl ether, diacrylate -1,6-HD ester（HDDA）In one or more mixture.
Application of the above-mentioned heat-resisting color inhibition epoxy acrylate oligomer in UV ink, wherein, the UV ink is silk
Silk screen printing ink.
The UV ink by following parts by weight material composition：
40～60 parts of epoxy acrylate oligomer；
1～40 part of pigment；
1～2 part of dispersant；
1～10 part of filler；
2～8 parts of light trigger；
1～2 part of antioxidant；
1～3 part of thickening agent；
1～2 part of defoamer.
Preferably, in above-mentioned UV ink, described pigment is Rutile type titanium dioxide, Griffith's zinc white. powder, C lake red CAN'T, middle chromium
One or more mixture in Huang, ultramarine, phthalocyanine blue, phthalocyanine green, titanium chrome green, white carbon black.
Preferably, in above-mentioned UV ink, described light trigger is the oxidation of 2,4,6- trimethyl benzoyl diphenyl bases
It is phosphine, 2,4,6- trimethylbenzoyl ethoxyl phenenyl phosphine oxides, double（2,4,6- trimethylbenzoyls）In phenyl phosphine oxide
One or more mixture.
Preferably, in above-mentioned UV ink, the dispersant selects methyl anyl alcohol, oleyl amine acetate, alkyl quaternary
One or more mixture in ammonium salt, amino propylamine dioleate.
Preferably, in above-mentioned UV ink, described inserts are the one kind or several in Calcium Carbonate, barium sulfate, Pulvis Talci
Plant mixture.
The heat-resisting color inhibition Epocryl that the present invention is provided is applied to after UV ink, the UV ink has resistance to
The characteristics of heat, color inhibition, high glaze.Because TGIC has the special construction of triazine ring, its stable performance, heat-resisting yellowing resistance
It is good, while introduce on TGIC with photoactive group, so as to the oligomer for ensureing synthesized has good photocuring
Performance.In addition, it is modified to it using anhydride, the alkali solubility of synthesized oligomer is improved, expand the application model of the UV ink
Enclose.Therefore this kind of UV ink solves the problems, such as that in the market the heat-resisting yellowing resistance of UV ink is poor.
The preparation method of above-mentioned UV ink, concrete preparation method is as follows：
Resin, pigment, filler, light trigger, dispersant, antioxidant, defoamer, thickening agent are added into homogenizer
In stir, with three-roller grind 3～5 times, fineness≤25 μm obtain final product UV ink.
Compared with prior art, the present invention has the advantages that：
Prepared using phenolic aldehyde, bisphenol-a epoxy acrylate resin more than traditional UV ink, the tree of this kind of UV ink
Fat heat resistance in high temperature not enough, can produce Yellowing.UV ink prepared by the present invention adopts the epoxy of heat-resisting color inhibition
Acrylate oligomer, overcomes the defect of the easy xanthochromia of traditional UV ink, and the adhesive force of the UV ink is strong, and base material is made
It is wide with scope, can be with silk-screen on PE, PP, PET, glass, wiring board etc..
（1）The characteristics of modified resin synthesized by the present invention has heat-resisting, color inhibition and high glaze, while having good
Ultraviolet light polymerization performance.
（2）Compared with traditional UV ink of domestic production, UV ink prepared by the present invention has bloom to the ink of the present invention
Pool property, excellent thermostability, yellowing resistance and applied range.
Specific implementation method
With reference to embodiment, the present invention will be further described.These embodiments are only that the typical case to the present invention retouches
State, but the invention is not restricted to this.Test method used if no special instructions, is conventional method in following embodiments, is made
Raw material, reagent etc., if no special instructions, being can be from the raw material and reagent that routinely commercial sources such as commercial are obtained.
Performance test:
1. the fineness of ink is determined according to GB/T 13217.3-2008；
2. attachment fastness of the ink to glass is determined according to GB/T 13217.7-2009；
3. the viscosity of ink, rotating cylinder viscometer method are determined according to GB/T 13217.4-2008；
4. the glossiness of ink is determined according to GB/T 13217.2-2009；
5. acid resistance：Glass plate after UV solidifies is put in the sulfuric acid solution that mass fraction is 10%, is soaked
20min, taking-up is cleaned with clear water, is dried naturally, and with adhesive tape adhesion the glass plate of ink has been applied, and observation ink falls damage situation；
6. alkali resistance：Glass plate after UV solidifies is put in the sodium hydroxide solution that mass fraction is 10%, is soaked
20min, taking-up is cleaned with clear water, is dried naturally, and with adhesive tape adhesion the glass plate of ink has been applied, and observation ink falls damage situation；
7. ink xanthochromia performance：The whiteness of the ink Jing after UV solidifications is tested with SBDY-1 digital display whiteness instrument, then is placed into
150 DEG C of baking oven, toasts 60min, and taking-up is placed into room temperature, tests its whiteness；
8. ink cracking situation：Put the glass plate after UV solidifies into 150 DEG C of baking oven, toast 60min, taking-up is put
Put room temperature, observation ink cracking situation.
Embodiment 1
（1）The synthesis of epoxy acrylate oligomer TGICAHHPA
In equipped with overhead type stirrer, thermometer, the four-neck flask of the 100mL of bulb condensation pipe device, 14.8g is added
（0.05mol）TGIC and 10.8g（0.15mol）AA, oil bath heating to 90 DEG C.After TGIC and AA are completely dissolved, 100 are warmed up to
DEG C, agitator is started, while adding 0.15g Triethylamine catalysts, 4h is reacted, 0.1g hydroquinone of polymerization retarder is added, obtain
Bright sticky mass.15.4g is added in reaction bulb（0.1mol）HHPA, oil bath heating to 100 DEG C reacts 30min, then
Solvent drop is glutinous to add 15g acetone to do, and 90min is reacted in continuation, adds 5g HDDA as reactive diluent, and regulation system viscosity is cold
But discharge, obtain clear viscous shape material, its GPC check weighings average molecular weight is 1031, and molecular weight distribution index is 1.02.
（2）The preparation of ink and method of testing
60 parts of TGICAHHPA；
36 parts of titanium dioxide r902；
2 parts of oleyl amine acetate；
2 parts of Calcium Carbonate；
819 8 parts of light trigger Easepi；
2 parts of 2,6 di tert butyl 4 methyl phenol；
3 parts of silicon dioxide N20；
2 parts of TEGO Foamex N defoamer.
A. above-mentioned material is mixed according to formula ratio, is then disperseed with high speed dispersor, rate of dispersion 1000rpm, stirring
Dispersion 30min, is ground 4 times with three-roller, and fineness is determined below 25 μm with fineness gauge, obtains final product UV ink, tests its performance.
B. 43T is adopted（110 mesh）Screen process press the UV ink for preparing is printed to glass plate, be put into ultraviolet
Light（280～385nm）Lower solidification 3min, carries out performance test.
The chalk that embodiment 1 is prepared, viscosity is 11000cp at 25 DEG C, and fineness is 20 μm, and attachment fastness is 100%,
Glossiness is 97 °, and Jing after soda acid immersion, ink does not fall off, and whiteness is 95 ° before ink baking, and whiteness is 94 ° after baking, and is dried
Ink does not ftracture after roasting, and the ink has the performances such as good heat-resisting, color inhibition, high gloss.
Embodiment 2
（1）The synthesis of epoxy acrylate oligomer TGICAMA
In equipped with overhead type stirrer, thermometer, the four-neck flask of the 100mL of bulb condensation pipe device, 14.8g is added
（0.05mol）TGIC and 10.8g（0.15mol）AA, while adding 0.1g hydroquinone of polymerization retarder.Oil bath heating is treated to 90 DEG C
After TGIC and AA are completely dissolved, 100 DEG C are warmed up to, start agitator, while adding 0.15g Triethylamine catalysts, react 4h, obtained
To clear viscous shape material.9.8g is added in reaction bulb（0.1mol）MA, oil bath heating to 100 DEG C reacts 30min, so
Solvent drop is glutinous to add 15g acetone to do afterwards, and 90min is reacted in continuation, adds 5g diacrylate -1,6- hexanediol esters（HDDA）As work
Property diluent, regulation system viscosity, cooling discharging obtains clear viscous shape material, and its GPC check weighings average molecular weight is 1525, point
Son amount breadth coefficient is 1.03.
（2）The preparation of ink and method of testing
60 parts of TGICAMA；
72 parts of Phthalocyanine Green G NX PG；
2 parts of oleyl amine acetate；
2 parts of barium sulfate；
819 8 parts of light trigger Easepi；
2 parts of 2,6 di tert butyl 4 methyl phenol；
3 parts of silicon dioxide N20；
1 part of TEGO Foamex N defoamer.
A. above-mentioned material is mixed according to formula ratio, is then disperseed with high speed dispersor, rate of dispersion 1000rpm, stirring
Dispersion 30min, is ground 4 times with three-roller, and fineness is determined below 25 μm with fineness gauge, adds defoamer to stir, and is obtained final product
UV ink, tests its performance.
B. 43T is adopted（110 mesh）Screen process press the UV ink for preparing is printed to PET sheet, be put into purple
Outer light（280～385nm）Lower solidification 3min, carries out performance test.
The green ink that embodiment 2 is prepared, viscosity is 10000cp at 25 DEG C, and fineness is 20 μm, and attachment fastness is 100%,
Glossiness is 98 °.
Embodiment 3
（1）The synthesis of epoxy acrylate oligomer TGICATMA
In equipped with overhead type stirrer, thermometer, the four-neck flask of the 100mL of bulb condensation pipe device, 14.8g is added
（0.05mol）TGIC and 10.8g（0.15mol）AA, while adding 0.1g hydroquinone of polymerization retarder.Oil bath heating is treated to 90 DEG C
After TGIC and AA are completely dissolved, 100 DEG C are warmed up to, start agitator, while adding 0.15g Triethylamine catalysts, react 4h, obtained
To clear viscous shape material.19.2g is added in reaction bulb（0.1mol）TMA, oil bath heating to 100 DEG C reacts 30min, so
Solvent drop is glutinous to add 15g acetone to do afterwards, and 90min is reacted in continuation, adds 5g diacrylate -1,6- hexanediol esters（HDDA）As work
Property diluent, regulation system viscosity, cooling discharging obtains clear viscous shape material, and its GPC check weighings average molecular weight is 1428, point
Son amount breadth coefficient is 1.02.
（2）The preparation of ink and method of testing
60 parts of TGICATMA；
2 parts of C lake red CAN'T LCY；
2 parts of oleyl amine acetate；
2 parts of barium sulfate；
819 8 parts of light trigger Easepi；
2 parts of 2,6 di tert butyl 4 methyl phenol；
3 parts of silicon dioxide N20；
1 part of TEGO Foamex N defoamer.
A. above-mentioned material is mixed according to formula ratio, is then disperseed with high speed dispersor, rate of dispersion 1000rpm, stirring
Dispersion 30min, is ground 4 times with three-roller, and fineness is determined below 25 μm with fineness gauge, adds defoamer to stir, and is obtained final product
UV ink, tests its performance.
B. 43T is adopted（110 mesh）Screen process press by the UV ink for preparing print to Jing flame treatments PE mould
On material bottle, ultraviolet light is put into（280～385nm）Lower solidification 3min, carries out performance test.
The red ink that embodiment 3 is prepared, viscosity is 11000cp at 25 DEG C, and fineness is 20 μm, and attachment fastness is 100%,
Glossiness is 97 °.
Claims (9)
1. a kind of heat-resisting color inhibition epoxy acrylate oligomer, it is characterised in that make by the following method：By isocyanuric acid three
There is addition esterification in ethylene oxidic ester, acrylic compounds organic acid, obtain isocyanuric acid three-glycidyl third under catalyst
Olefin(e) acid ester, then anhydride modified isocyanuric acid three-glycidyl acrylate is obtained with anhydride reaction, be eventually adding thinner and
Reactive diluent, regulation system viscosity is obtained final product；
Triglycidyl isocyanurate is 1.0 with the mol ratio of acrylic compounds organic acid, anhydride：（2.8～3.2）：2.0；Urge
The amount of agent accounts for the 0.6% of triglycidyl isocyanurate and acrylic compounds organic acid gross weight；The addition of the thinner
Account for the 33～45% of reactant gross weight；The addition of the reactive diluent accounts for the 10～15% of reactant gross weight；
The synthetic method of epoxy acrylate oligomer is：Equipped with overhead type stirrer, thermometer, bulb condensation pipe device
In the four-neck flask of 100mL, 14.8gTGIC and 10.8gAA, oil bath heating to 90 DEG C are added；After TGIC and AA are completely dissolved,
100 DEG C are warmed up to, agitator is started, while adding 0.15g Triethylamine catalysts, 4h is reacted, 0.1g polymerization inhibitors is added to benzene two
Phenol, obtains clear viscous shape material；15.4g HHPA, oil bath heating to 100 DEG C is added to react 30min, then in reaction bulb
Solvent drop is glutinous to add 15g acetone to do, and 90min is reacted in continuation, adds 5g HDDA as reactive diluent, and regulation system viscosity is cold
But discharge, obtain clear viscous shape material.
2. heat-resisting color inhibition epoxy acrylate oligomer according to claim 1, it is characterised in that described acrylic acid
Class organic acid is one or more mixture in acrylic acid, methacrylic acid.
3. heat-resisting color inhibition epoxy acrylate oligomer according to claim 1, it is characterised in that described catalyst
For toluene sulfonic acide, phosphoric acid, triethylamine, N, one or more mixture in N- dimethyl cyclohexyl amines, triethanolamine.
4. heat-resisting color inhibition epoxy acrylate oligomer according to claim 1, it is characterised in that described anhydride is
One or more mixture in HHPA, maleic anhydride, trimellitic anhydride.
5. heat-resisting color inhibition epoxy acrylate oligomer according to claim 1, it is characterised in that described thinner
For one or more mixture in toluene, ethyl acetate, acetone；Described reactive diluent is phenyl glycidyl ether, second
One or more mixture in Hexanediol diglycidyl ether, diacrylate -1,6-HD ester.
6. the heat-resisting color inhibition epoxy acrylate oligomer described in claim 1 to 5 any claim is preparing UV ink
In application.
7. a kind of UV ink of heat-resisting color inhibition, it is characterised in that by the material composition of following parts by weight：
40～60 parts of epoxy acrylate oligomer；
1～40 part of pigment；
1～2 part of dispersant；
1～10 part of filler；
2～8 parts of light trigger；
1～2 part of antioxidant；
1～3 part of thickening agent；
1～2 part of defoamer；
The epoxy acrylate oligomer is the heat-resisting color inhibition epoxyacrylate oligomers described in any one of claim 1-5
Thing.
8. the UV ink of heat-resisting color inhibition according to claim 7, it is characterised in that described pigment is rutile type titanium
One or more mixing in white lead, Griffith's zinc white. powder, C lake red CAN'T, medium chrome yellow, ultramarine, phthalocyanine blue, phthalocyanine green, titanium chrome green, white carbon black
Thing.
9. the preparation method of the UV ink of heat-resisting color inhibition described in claim 7, it is characterised in that comprise the steps：Will tree
Fat, pigment, filler, light trigger, dispersant, antioxidant, defoamer, thickening agent are added and are sufficiently stirred in homogenizer
It is even, to be ground 3～5 times with three-roller, fineness≤25 μm obtain final product UV ink.
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| CN106752316A (en) * | 2016-12-26 | 2017-05-31 | 武汉长盈鑫科技有限公司 | A kind of resistant to elevated temperatures optical fiber coloring ink |
| CN106977988B (en) * | 2017-05-11 | 2020-02-18 | 京东方科技集团股份有限公司 | Protective coating, preparation method and mask plate |
| CN107203095B (en) * | 2017-07-19 | 2020-08-18 | 江苏广信感光新材料股份有限公司 | White alkali-soluble photosensitive composition and preparation method and application thereof |
| CN107353707B (en) * | 2017-08-21 | 2020-12-18 | 浙江银鹿化工有限公司 | Preparation method of heat-resistant ink composition |
| CN107722713B (en) * | 2017-10-09 | 2020-11-13 | 广东高仕电研科技有限公司 | Double-component liquid photosensitive white solder resist ink for PCB and preparation method thereof |
| CN107760102A (en) * | 2017-11-03 | 2018-03-06 | 苏州工业园区汇统科技有限公司 | A kind of back up label |
| CN108003271B (en) * | 2017-12-25 | 2020-06-16 | 广东三求光固材料股份有限公司 | Alkali-soluble electroplating-resistant photosensitive resin and preparation method and application thereof |
| TWI666670B (en) * | 2018-05-18 | 2019-07-21 | 致伸科技股份有限公司 | Keycap structure and manufacturing method thereof |
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