CN104877446A - Ultraviolet-thermal dual-curing glass printing ink and preparation method thereof - Google Patents

Ultraviolet-thermal dual-curing glass printing ink and preparation method thereof Download PDF

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Publication number
CN104877446A
CN104877446A CN201510344639.6A CN201510344639A CN104877446A CN 104877446 A CN104877446 A CN 104877446A CN 201510344639 A CN201510344639 A CN 201510344639A CN 104877446 A CN104877446 A CN 104877446A
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China
Prior art keywords
ultraviolet
weight part
glass ink
printing ink
dual cure
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Granted
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CN201510344639.6A
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Chinese (zh)
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CN104877446B (en
Inventor
姚娜
李刚
李令明
余逸
刘丽湘
王慧
李鸣伟
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Tianjin Synthetic Material Industry Research Institute Co Ltd
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Tianjin Synthetic Material Industry Research Institute Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof

Abstract

The invention provides ultraviolet-thermal dual-curing glass printing ink. The glass printing ink comprises resin containing epoxy groups and double bonds, urethane acrylate, acrylic ester active monomers, and the glass printing ink further comprises a latent curing agent, photoinitiator, promoter, an antifoaming agent, a flatting agent, padding materials, a polymerization inhibitor and organic dyestuff. The printing ink is cured type glazed printing ink, excellent adhesive force is achieved on various types of glass, and the printing ink has the advantages of being good in water resistance, solvent resistance and grease resistance, free of net-blocking and high in ultraviolet curing speed, the printing ink is particularly suitable for being used for printing some certain exquisite images and texts, a full, distinct, bright and sharp printing effect is achieved, and meanwhile the high hiding rate is achieved.

Description

A kind of ultraviolet-heat dual cure glass ink and preparation method thereof
Technical field
The invention belongs to technical field of ink, particularly relate to a kind of ultraviolet-heat dual cure glass ink and preparation method thereof.
Background technology
Ink product of the prior art generally belongs to high temperature sintering type ink, needs to consume a large amount of energy; In addition, a lot of product all uses volatile solvent, can to environment; Although existing water color ink is avoided using volatile solvent, environment is more friendly, but water color ink curing speed is slow, general one week of needs just can reach higher-strength, and in thermofixation link, solidification face is vulnerable to pollute, when needs multicolor overprint, need frequent operation, use very inconvenient; Nowadays ultraviolet curing glass printing ink on the market has the advantage of environmental protection, fast setting, raising products production efficiency, but it is poor that ultraviolet curing glass printing ink also exists water tolerance, cannot be applied in glass surface that water tolerance is had higher requirements, as shower house, beverage bottle etc.
Summary of the invention
The problem to be solved in the present invention is for above-mentioned deficiency, improves a kind of ultraviolet-heat dual cure glass ink, and to solve, common ink curing speed is slow and ultraviolet curing glass printing ink sticking power is low, the problem of poor water resistance.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
A kind of ultraviolet-heat dual cure glass ink, this glass ink comprises the resin containing epoxide group and double bond of 20-50 weight part, the urethane acrylate of 10-30 weight part; The acrylate reactive monomer of 15-40 weight part.
Further, this glass ink also comprises latent curing agent, light trigger, aided initiating, defoamer, flow agent, filler, stopper and organic dye.
Further, this glass ink also comprises the latent curing agent of 2-4 weight part, the light trigger of 2-5 weight part, the aided initiating of 0.5-3 weight part, the defoamer of 0.5-2 weight part, the flow agent of 0.5-2 weight part, the filler of 5-10 weight part, the stopper of 0.02-0.1 weight part, the organic dye of 5-10 weight part.
Further, the described resin containing epoxide group and double bond is obtained by reacting by one or more and the vinylformic acid that comprise in bisphenol A epoxide resin, bisphenol F epoxy resin, aliphatic epoxy resin, novolac epoxy.
Further, resin containing epoxide group and double bond (can referred to as half ester) prepares by the following method: add containing N in any one epoxy resin above-mentioned, the vinylformic acid of N-dimethyl benzylamine and MEHQ, temperature control about 100 DEG C, stirring reaction, when the acid number of reaction system is less than 3mgKOH/g, terminates reaction, to obtain final product.
Further, described urethane acrylate is one or more in aliphatic urethane acrylate or aromatic urethane acrylate, is preferably aliphatic urethane acrylate.This urethane acrylate adopts known method to prepare, such as, adopt isophorone diisocyanate (IPDI), hexamethylene-diisocyanate (HDI) or two ring ethyl methane vulcabond (HMDI) and polyether glycol to react, then react with Hydroxyethyl acrylate or Propylene glycol monoacrylate and obtain urethane acrylate.
Further, described acrylate reactive monomer is methacrylic ester, lauryl methacrylate(LMA) (LA), isobornyl methacrylate (IBOA), N, the mixture of one or more and a kind of acrylate monomer containing epoxide group in N-DMAA (DMAA), 1,4 butanediol diacrylate (HDDA), methacrylic acid.
Further, described a kind of acrylate monomer containing epoxide group is glycidyl methacrylate (GMA).
Further, described latent curing agent is imidazole curing agent, is preferably imidazoles, glyoxal ethyline, 2-ethyl-4-methylimidazole, 2-phenylimidazole, and the mixture of one or more and Dyhard RU 100 in PN-23, is more preferably the mixture of PN-23 and Dyhard RU 100.
Further, described light trigger is but is not limited to the trade mark 1173,184,651,369, BP, TPO, the one in ITX or several arbitrarily.
Concrete, 1173 is 2-hydroxy-2-methyl-1-phenyl-acetone; 184 is 1-hydroxy cyclohexyl phenylketone; 651 is α, α '-dimethyl benzil ketals; BP is benzophenone; TPO is 2,4,6-trimethyl benzoyl diphenyl base phosphorus oxide; ITX is 2-isopropyl thioxanthone.
Further, described stopper is quinhydrones (HQ), para benzoquinone (PBQ), one or more in 2,6 ditertiary butyl p cresol.
The present invention also provides the preparation method of any one ultraviolet-heat dual cure glass ink above-mentioned, comprises the steps:
(1) add the resin containing epoxide group and double bond, urethane acrylate, part propylene acid esters reactive monomer, stopper, initiator, aided initiating, filler and organic dye, stir evenly pre-dispersed;
(2) by the triple-roller mill of material by cooling water control, be rolled;
(3) in material, add latent curing agent, stir, by the triple-roller mill of material by cooling water control, rolling, controls fineness below 10 μm;
(4) point ink cleared is added defoamer, flow agent, and remaining acrylate reactive monomer, stir and get product.
The advantage that the present invention has and positively effect are:
1, this glass ink adopt resin and monomer contain epoxide group and double bond, can make photocuring reaction and thermofixation reaction well combine, make reaction system homogeneous, curing performance is excellent, and Cohesion reliability is high, and save energy is applied widely.
2, this ink is the high bright ink of curing, has excellent sticking power to all kinds of glass, and has the well characteristic such as water-fast, solvent and grease.
3, this ink has not network blocking and the fireballing characteristic of ultra-violet curing, and special society and some meticulous picture and text of printing, have plentiful, clear, bright and sharp printing effect, also have high hiding rare simultaneously.
4, use this ink greatly to enhance productivity, reduce taking of production space, save the energy significantly.
Embodiment
Embodiment 1 (Lan Mo)
Each raw material is accurately weighed, epoxy acrylic half ester 45g, bifunctional urethane acrylate 14g by following weight, 2,6 ditertiary butyl p cresol 0.1g, glycidyl methacrylate 20g, 6511.5g, benzophenone 1.5g, 11731.5g, titanium dioxide 8g, phthalocyanine blue 6g, opens and stirs 300-400rpm, pre-dispersed 20 minutes, by the triple-roller mill of cooling water control after being uniformly dispersed, rolling twice.Add Dyhard RU 100 1.5g again, PN-230.8g, stir, by the triple-roller mill of material by cooling water control, rolling one time, requires that fineness is below 10 μm.Point ink cleared is added organic silicone oil 0.5g and TEGOFoamex N 0.5g and methacrylic ester 8g.Moderate-speed mixer 20 minutes, stirs, is finished product.
The preparation method of epoxy acrylic half ester:
The epoxy resin 618 of 200g is added in 500mL there-necked flask, mechanical stirring, oil bath 100 DEG C, then add containing 0.25g N, the vinylformic acid 37g of N-dimethyl benzylamine and 0.25g MEHQ, every 20min sampling and measuring acid number, when the acid number in reaction system is less than 3mgKOH/g, namely think that esterification completes, obtain epoxy acrylic half ester.Epoxy acrylic half ester is directly coated on KBr salt sheet, measures with infrared spectrometer (RFX-65A FTIR), can see in the infrared spectra spectrogram of the epoxy acrylic half ester before solidification, there is obvious double bond group characteristic peak (1640cm -1, 810cm -1) and the absorption peak (980cm of epoxide group -1, 910cm -1, 771cm -1).
Embodiment 2 (tusche)
Each raw material is accurately weighed, epoxy acrylic half ester 40g, trifunctional urethane acrylate 30g by following weight, 2,6 ditertiary butyl p cresol 0.1g, glycidyl methacrylate 18g, 3692g, ITX 0.6g, titanium dioxide 5g, carbon black 5g, open and stir 300-400rpm, pre-dispersed 20 minutes, by the triple-roller mill of cooling water control after being uniformly dispersed, rolling twice.Add Dyhard RU 100 2g again, PN-230.6g, stir, by the triple-roller mill of material by cooling water control, rolling one time, requires that fineness is below 10 μm.Point ink cleared is added organic silicone oil 0.8g and TEGO Foamex N 0.6g and methacrylic ester 5g.Moderate-speed mixer 20 minutes, stirs, is finished product.
The preparation method of epoxy acrylic half ester is with embodiment 1.
Glass baseplate should be cleaned up 2. half tones before printing by the using method of glass ink of the present invention: l.: 250 order-420 orders, ink film thickness: be advisable to be less than 10 μm.3.UV lamp power: be greater than 100W/CM.4., time as regelate, UV ink first solidifies under uv lamps, carries out thermosetting once again after completing whole chromatography through drying tunnel.5. thermosetting condition: 5-15 minute at 160 DEG C of temperature.7., when printing multi-laminate additive color, answer look UV intensity of illumination before Hypoprosexia, avoid the phenomenon causing rear look additivity poor due to front look over-curing.8., when printing environment temperature is 25 DEG C, ink reaches best printing performance.
By the experimental test embodiment of the present invention below the performance of ultraviolet-heat dual cure glass ink.
Testing method: 1. printing material: sheet glass; 2. silk screen printing, half tone 300 order; 3. set time: UV solidifies 15 stopwatches dry (ultraviolet lamp power: be greater than 100W/CM); Post-heating solidifies: 160 DEG C are heated 15 minutes.Test result is as shown in the table:
Project Test condition Result
Sticking power Cross-hatching, tape stripping, draws compartment apart from 1mm 100％
Hardness Pencil hardness >4H
Resistant to acetone is tested Be soaked with the face ball wiping of acetone 200 times
Alkali resistance Be soaked with the cotton balls of salt solution, 300 grams of pressure wipings 100 times Be as good as shape
Acid resistance Be soaked with the cotton balls of sulfiting agent, wiping 100 times Be as good as shape
Water tolerance Immerse in the boiling water of 100 DEG C and boil 200 hours Do not come off
Grease resistance To be soaked in salad oil (normal temperature) 8 hours Be as good as shape
By the following method by the sample of embodiment and the ink prepared by patent CN200910154787 embodiment (abbreviation comparative example), after solidification, carry out the contrast test of performance:
Project The present invention Comparative example
Sticking power 100％ 100％
Hardness >4H 2H
Resistant to acetone 200 times 100 times
Water tolerance 200 hours, do not come off 12 hours, come off
Above embodiments of the invention have been described in detail, but described content being only preferred embodiment of the present invention, can not being considered to for limiting practical range of the present invention.All equalizations done according to the present patent application scope change and improve, and all should still belong within patent covering scope of the present invention.

Claims (10)

1. a ultraviolet-heat dual cure glass ink, is characterized in that: this glass ink comprises the resin containing epoxide group and double bond of 20-50 weight part, the urethane acrylate of 10-30 weight part; The acrylate reactive monomer of 15-40 weight part.
2. ultraviolet-heat dual cure glass ink according to claim 1, is characterized in that: this glass ink also comprises latent curing agent, light trigger, aided initiating, defoamer, flow agent, filler, stopper and organic dye.
3. ultraviolet-heat dual cure glass ink according to claim 2, it is characterized in that: this glass ink comprises the latent curing agent of 2-4 weight part, the light trigger of 2-5 weight part, the aided initiating of 0.5-3 weight part, the defoamer of 0.5-2 weight part, the flow agent of 0.5-2 weight part, the filler of 5-10 weight part, the stopper of 0.02-0.1 weight part, the organic dye of 5-10 weight part.
4. according to the arbitrary described ultraviolet-heat dual cure glass ink of claim 1-3, it is characterized in that: the described resin containing epoxide group and double bond is obtained by reacting by one or more and the vinylformic acid that comprise in bisphenol A epoxide resin, bisphenol F epoxy resin, aliphatic epoxy resin, novolac epoxy.
5. ultraviolet-heat dual cure glass ink according to claim 4, it is characterized in that: described urethane acrylate is one or more in aliphatic urethane acrylate or aromatic urethane acrylate, is preferably aliphatic urethane acrylate.
6. the ultraviolet-heat dual cure glass ink according to claim 1 or 2 or 3 or 5, it is characterized in that: described acrylate reactive monomer is methacrylic ester, lauryl methacrylate(LMA), isobornyl methacrylate, N, the mixture of one or more and a kind of acrylate monomer containing epoxide group in N-DMAA, 1,4 butanediol diacrylate, methacrylic acid.
7. ultraviolet-heat dual cure glass ink according to claim 6, is characterized in that: described a kind of acrylate monomer containing epoxide group is glycidyl methacrylate.
8. the ultraviolet-heat dual cure glass ink according to claim 1 or 2 or 3 or 5 or 7, it is characterized in that: described latent curing agent is imidazole curing agent, be preferably imidazoles, glyoxal ethyline, 2-ethyl-4-methylimidazole, 2-phenylimidazole, the mixture of one or more and Dyhard RU 100 in PN-23, is more preferably the mixture of PN-23 and Dyhard RU 100.
9. ultraviolet-heat dual cure glass ink according to claim 8, is characterized in that: described light trigger is but is not limited to the trade mark 1173,184,651,369, BP, TPO, the one in ITX or several arbitrarily.
10. the preparation method of the arbitrary described ultraviolet-heat dual cure glass ink of claim 1-9, is characterized in that, comprise the steps:
(1) add the resin containing epoxide group and double bond, urethane acrylate, part propylene acid esters reactive monomer, stopper, initiator, aided initiating, filler and organic dye, stir evenly pre-dispersed;
(2) by the triple-roller mill of material by cooling water control, be rolled;
(3) in material, add latent curing agent, stir, by the triple-roller mill of material by cooling water control, rolling, controls fineness below 10 μm;
(4) point ink cleared is added defoamer, flow agent, and remaining acrylate reactive monomer, stir and get product.
CN201510344639.6A 2015-06-19 2015-06-19 A kind of ultraviolet hot dual cure glass ink and preparation method thereof Active CN104877446B (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107141881A (en) * 2017-05-18 2017-09-08 苏州昭奇凯虹精细化工有限公司 LED cured printing inks and its preparation, curing for part surface of painting
CN107337958A (en) * 2017-07-27 2017-11-10 广东印彩科技有限公司 A kind of LED dual cures transfer novel ink and preparation method thereof
CN109294303A (en) * 2018-09-30 2019-02-01 无锡卡秀堡辉涂料有限公司 A kind of ultraviolet-heat dual cure glass coating
CN109777192A (en) * 2017-11-15 2019-05-21 洛阳尖端技术研究院 A kind of UV curable ink and preparation method thereof
CN110669377A (en) * 2019-09-09 2020-01-10 广州视源电子科技股份有限公司 Glass printing ink, preparation method and application
EP3814023A4 (en) * 2018-05-10 2021-07-21 Sun Chemical Corporation Actinic radiation curable compositions including semiconductor metal oxide materials
CN113980501A (en) * 2021-11-19 2022-01-28 国网江苏省电力有限公司电力科学研究院 Photo-induced front-line polymerized graphene super-hydrophobic anticorrosive coating and preparation method thereof

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107141881A (en) * 2017-05-18 2017-09-08 苏州昭奇凯虹精细化工有限公司 LED cured printing inks and its preparation, curing for part surface of painting
CN107337958A (en) * 2017-07-27 2017-11-10 广东印彩科技有限公司 A kind of LED dual cures transfer novel ink and preparation method thereof
CN109777192A (en) * 2017-11-15 2019-05-21 洛阳尖端技术研究院 A kind of UV curable ink and preparation method thereof
EP3814023A4 (en) * 2018-05-10 2021-07-21 Sun Chemical Corporation Actinic radiation curable compositions including semiconductor metal oxide materials
US11254830B2 (en) 2018-05-10 2022-02-22 Sun Chemical Corporation Actinic radiation curable compositions including semiconductor metal oxide materials
CN109294303A (en) * 2018-09-30 2019-02-01 无锡卡秀堡辉涂料有限公司 A kind of ultraviolet-heat dual cure glass coating
CN110669377A (en) * 2019-09-09 2020-01-10 广州视源电子科技股份有限公司 Glass printing ink, preparation method and application
CN113980501A (en) * 2021-11-19 2022-01-28 国网江苏省电力有限公司电力科学研究院 Photo-induced front-line polymerized graphene super-hydrophobic anticorrosive coating and preparation method thereof

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