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CN106366755A - Photo-cured printing ink composition for food, medicine and cosmetic package - Google Patents

Photo-cured printing ink composition for food, medicine and cosmetic package Download PDF

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Publication number
CN106366755A
CN106366755A CN201610775856.5A CN201610775856A CN106366755A CN 106366755 A CN106366755 A CN 106366755A CN 201610775856 A CN201610775856 A CN 201610775856A CN 106366755 A CN106366755 A CN 106366755A
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CN
China
Prior art keywords
acrylate
monomer
ink
compound
compositionss
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201610775856.5A
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Chinese (zh)
Inventor
武瑞
张齐
董月国
赵建新
姚娜
赵国锋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tianjin Jiuri New Materials Co Ltd
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Tianjin Jiuri New Materials Co Ltd
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Priority to CN201610775856.5A priority Critical patent/CN106366755A/en
Publication of CN106366755A publication Critical patent/CN106366755A/en
Pending legal-status Critical Current

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Classifications

    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

The invention provides a photo-cured printing ink composition with good aridity, low mobility and good adhesive force. The composition can not only be applied to packaging materials of toys and various foods paying attention to safety and wholesomeness, but also be widely applied to package purposes of sanitary equipment, cosmetics and pharmaceuticals. The composition comprises a low-mobility thioxathone photoinitiator, bifunctional and polyfunctional acrylic ester composition monomer, resin oligomer with polymerized groups and polymerizable phosphonate compound.

Description

Light-curable ink compositionss for food, medicine and cosmetic package
Technical field
The invention belongs to Photocurable composition field and its for packages printing ink area and in particular to a kind of use
Light-curable ink compositionss in food, medicine and cosmetic package.
Background technology
According to its drying mode, ink composite substantially can be divided into following five kinds:
1st, water base ink, its drying mechanism is related to absorb, permeate and evaporate；
2nd, the ink of solvent base, its drying relates generally to evaporate；
3rd, the ink of oil base, its drying is related to absorb and permeates；
4th, heat melt or phase transformation ink, wherein this ink is liquid under injection temperation, but is solid at room temperature, and Wherein instead of drying with solidification；
5th, can uv solidification ink, with polymerization instead of drying.
It will be clear that the ink composite of first three types is more suitable for absorbefacient base material, and the oil that heat is melted Ink and can uv cured printing ink due to being also used on the base material of nonabsorbable, especially uv cured printing ink has won in printer More and more pay close attention in industry.Uv curing technology with its own unique environmental protection and energy saving advantage, uv ink be widely used in furniture, The various fields such as electrical equipment, electronic product, automotive trim, medicated cigarette, food, medicine and cosmetic package.
To the concern of environmental problem and require more and more higher with the whole world, especially to food, medicine and toiletry bag In charge of oil ink cured layer, transportable residue there may be health risk, and therefore it should be maintained at absolute minimum amount, that is, be suitable for In the limit value of regulation, packaging ink decree sr817.023.21 of described regulation such as Switzerland.The animal migration of ink and toxicity, this Be the whole world all in the problem of concern, such as U.S. f d a clear stipulaties u v ink cannot be used for there is directly contact with food Leaflet；European radiation curing association it is also proposed that, in uv ink some kinds of light trigger after ink solidification, residue Migration can pollute to packing material.Meanwhile, the odor problem of light trigger also limit uv ink in food, hygienic article side The application in face.These problems are in the field of business to cause extensive concern, reduces or eliminate residual light trigger in uv ink further Animal migration, toxicity and abnormal smells from the patient have become as the new research topic of industry.
Usually, uv light-curable ink comprises light trigger, coloring agent, activated monomer and prepolymer.Reduce and carry out self-curing The animal migration of the light trigger of ink layer, the known means of toxicity are using polymerization or polymerizable photoinitiator and coinitiator, The conventional low molecular weight compound of replacement, such as patent cn200410093977.9, cn201010218422.8, cn201410441880.6.
Coloring agent for light-curable ink can be dyestuff, but usually color pigment, its be attached to described pigment The polymeric dispersant on surface together, is generally difficult to extract.
For can extracting, a remaining difficult problem is monomer.Polymerizable oligomerses or crosslinkable polymer substitute low-molecular-weight Monomer using only possible up to a certain amount in ink, need ink to have under injection temperation especially for ink jet printing Caused by having low viscous restriction.Document (as ep2053101, ep2053103) is had to report for making the unreacted monomer that can extract Amount be reduced to minimum.But monomer can be extracted and can cause problem by way of other two kinds are different: set-off (set-off) and Migration.Set-off occurs in volume to volume printing, and now the printed front of packaging material starts and the rear-face contact not printed, and not The monomer set-off of reaction is on the back side being intended for direct food contact.Unreacted monomer is unnecessarily transferred to food, is Carried out by packaging material migration.
Additionally, food, medicine and cosmetic package ink not only will consider the number of its mobility, it is also contemplated that ink The adhesive force to packaging base material itself.
Content of the invention
It is an object of the invention to provide a kind of light-curable ink compositionss, it has good drying property and is used for eating The hypotoxicity of product, medicine and cosmetic package purposes, low migration, adhesive force are strong, wearability, not set-off.
The light-curable ink that the present invention provides, compared with the past, adopt that performance is good by appropriately combined thing, safety, low toxicity, The polymeric photoinitiators of low migration, monomer and polymer oligomer are such that it is able to realize above-mentioned purpose, and then complete this Bright.
The light-curable ink compositionss that the present invention provides, it contains light trigger, acrylate monomer, has polymer-based group Resin oligomers, polymerism phosphonate compound.
Light trigger mentioned here can be one-component, can also be double-component or multicomponent polymerization or polyfunctional group Thioxanthone photoinitiators, it is selected from the combination of one or more of following formula structural compounds,
Wherein:
Each r1Independently selected from: hydrogen, halogen, c1-c12 alkyl, c3-c6 cycloalkyl, c1-c12 alkoxyl；
r2And r3Each is independently selected from hydrogen, halogen, c1-c18 alkyl, c3-c6 cycloalkyl, c1-c18 alkoxyl；
r4Selected from hydrogen, halogen, c1-c12 alkyl, c1-c12 alkoxyl；
X is 2-6 or c1-c18 alkoxyl independently selected from the residue of polyhydric alcohol, wherein hydroxyl value；
N=0 or 1
M number is 1-6.
The acid ester substituent of thiaxanthone can be 1,2,3 or 4.
X is the residue of c2-c6 ployalkylene glycol, and wherein alkylene moiety has 2 to 6 carbon atoms or c2-c10 polyhydric alcohol Residue.The residue of c2-c10 polyhydric alcohol can be the polyhydric alcohol of straight or branched or ring-type.X preferably be selected from ethylene glycol, 1,2- or 1,3- propylene glycol, 1,2-, 1,3- or 1,4- butanediol, pentanediol, isoprene, Polyethylene Glycol, polypropylene glycol, polytetramethylene glycol, Trimethylolpropane, tetramethylolmethane, 1,2-, 1,3- or 1,4- cyclohexanediol, 1,4- hydroxymethyl-cyclohexane, glycerol, two seasons penta The residue of tetrol.
The polymeric polyhydroxy residue of x, it forms the core of the material of the present invention, and the behavior to this material has main shadow Ring.It is preferred according the present invention, that it should have aggregation property, because produced material is often liquid or has low Fusing point, thus contribute to the dispersion in recipe ingredient.There are similar structures but the compound of non-polymerization is often joined at these It is solid or soluble in Fang Zufen.The residue of the preferred x of the present invention is not it should have too high molecular weight；And preferably, x is residual Base should have no more than 2000 molecular weight, and more preferably no more than 1200.
The preferred having structure of n=1 up-to-date style compound is shown in Table 1:
Table 1
The preferred having structure of n=0 up-to-date style compound is shown in Table 2:
Table 2
In wherein above-mentioned table 1 part light trigger and table 2, light trigger needs and coinitiator is used together and just can reach anticipation Effect, coinitiator be selected from formula structural compounds:
Wherein:
A+b=n, 2≤n≤6, n is integer, and a, b are the integer more than or equal to 1；
r1、r2Identical or different, it is independently selected from the alkyl of c1-c4；
X is selected from o, s, nr3；
r3Selected from h, c1-c10 alkyl, aryl, aralkyl, alkaryl；
L is selected from the residue of the residue, the residue of multiamino compound or many sulfhydryl compounds of aliphatic polyhydroxy compound, hydroxyl The number of base, amino or sulfydryl is n；
It is preferably propylene glycol, butanediol, glycerol, 2,2- propylene glycol, Polyethylene Glycol, polypropylene glycol, polytetramethylene glycol, trihydroxy methyl Propane, the residue of 2- trimethylolpropane, tetramethylolmethane or 2- tetramethylolmethane；Dithioglycol, dimercaptopropane, succinimide mercaptans, third Three mercaptan, 2,2- dimercaptopropane, poly- dithioglycol, poly- dimercaptopropane, polybutadiene mercaptan, three thiopurine methyltransferase propane, 2- tri- hydroxyl mercapto first The residue of base propane, Ji Wusi mercaptan or 2- season penta 4 mercaptan；
R be selected from ethylenic unsaturated functional group, preferred acrylate, substituted acrylate, methacrylate, styrene, Acrylamide, Methacrylamide, allyl ester.
The preferred table of structural compounds 3 structure.
Table 3
The above-mentioned light trigger and/or coinitiator consumption in ink composite be selected from 0.2 ~ 20 weight % scope, preferably 1 ~ 10%.
In the light-curable ink compositionss that the present invention provides, acrylate monomer adopts bifunctional acrylate's monomer and many officials The mixing of acrylate monomer can be rolled into a ball.
Bifunctional acrylate's monomer that the present invention uses is preferred: double (methyl) acrylate of diethylene glycol, two contractings Double (methyl) acrylate of ethylene glycol, triethylene Glycol (methyl) acrylate, tripropylene glycol (methyl) acrylate, four contractings Ethylene glycol (methyl) acrylate, Polyethylene Glycol (200/400/600) (methyl) acrylate, 1,4- butanediol (methyl) propylene Acid esters, neopentyl glycol (methyl) acrylate, the third oxidation (2) neopentyl glycol (methyl) acrylate, the double (first of 1,6- ethylene glycol Base) acrylate, phthalic acid two (methyl) acrylate, double (methyl) acrylate of phthalic acid diethylene glycol, Ethoxyquin (10) bis-phenol a(methyl) acrylate and/or Hydroxypivalyl hydroxypivalate two (methyl) acrylate etc.. Multi-functional acrylate's monomer wherein trifunctional monomer is preferred: trimethylolpropane tris (methyl) acrylate, ethoxyquin Trimethylolpropane tris (methyl) acrylate, the third oxidation trihydroxy methyl (methyl) propane triacrylate, the third oxidation glycerol Three (methyl) acrylic resins and/or tetramethylolmethane three (methyl) acrylate etc.；Four-functional group and above monomer are preferred: season penta Tetrol four (methyl) acrylate, Bis(pentaerythritol) five (methyl) acrylate, double-trimethylolpropane four (methyl) acrylic acid Ester, ethoxyquin tetramethylolmethane four (methyl) acrylate, the third oxidation tetramethylolmethane four (methyl) acrylate and/or double Ji Wusi Alcohol six (methyl) acrylate etc..
The present invention provide light-curable ink compositionss in acrylate monomer content in the composition preferably with respect to More than 10 weight % of composition weight, preferably its content is 10 ~ 75 weight %, and wherein bifunctional acrylate's monomer accounts for and always mixes The part by weight closing monomer is selected from 0.1 ~ 50%.The viscosity that the consumption of monomer is not only for regulation composition to meet different need The mobility wanted, can also adjust resulting materials intensity and rigidity simultaneously.Although polyfunctional monomer can increase crosslinking points, can increase Plus the intensity of material, but in experimentation, inventor's discovery can lead to material brittle, and bifunctional monomer can increase material The rigidity of material is it is therefore desirable to be used in mixed way difunctional and polyfunctional monomer, and also ensures that curing rate, drying property And low migration.
The present invention provide light-curable ink compositionss in oligomer be selected from hyperbranched uv resin, polyester acrylate, three Official's polyester chloride acrylic ester, epoxy soybean oil acrylate, epoxy acrylate, modified epoxy acrylic ester and/or poly- ammonia Ester acrylate, preferably hyperbranched uv resin, polyester acrylate, epoxy acrylate, modified epoxy acrylic ester, polyurethane Acrylate.Such as polyurethane acrylate resin refers in particular to ebecryl 8402, ebecryl 8296；Polyester acrylate refers in particular to ebecryl 811、ebecryl 572；Epoxy acrylate refers in particular to ebecryl 648, ebecry 3708.
Content in ink composite for the above-mentioned oligomer is preferably with respect to 10 ~ 80 weight % of total composition.For Hyperbranched uv resin can be on a small quantity using being also to meet part needs not even using monomer.
Additionally, provide the essential component of compositionss: polymerism phosphonate compound as the present invention, refer at least contain 2 Ethylenic unsaturated bond, preferred acrylate group, methacrylic acid ester group, its consumption be selected from composition total weight 0.1 ~ 10%.The preferred table of polymerism phosphonate compound 4 structure:
As coloring agent, it is possible to use conventional organic or inorganic pigment or dyestuff, it is possible to use solubility AZOpigments, difficulty Insoluble azo pigment, condensed azo pigment, metallophthalocyanine pigment, no metallophthalocyanine pigment, charcoal blacks, quinacridone pigment, Other pigment such as anthraquione pigmentss.
The compositionss that the present invention provides optionally can also be suitably and with not anti-with other compositions beyond described compound The compound of the safety non-toxic answered, such as filler, antioxidant, inhibitor, levelling agent etc..
As the ink composite printing element of the present invention, be not particularly limited, can be various stationeries such as art paper, Art paper, thin paper, ground paper and various synthetic paper；Polyester resin, acrylic resin, vinyl chloride resin, polyethylene, poly- third The films such as alkene, nylon, Merlon or piece；Aluminium foil, cellophane；Wood materials, metal material glass material etc..
The preparation method of compositionss of the present invention: above-mentioned monomer, oligomer, light trigger, coloring agent or other are added Plus the cooperation such as agent stir mixing with mixer etc., it is ground using dispersion machines such as three Kun grinding machines, ball mills and prepare.
Specific embodiment
The present invention will be further illustrated with by following nonlimiting examples, use in concrete Photopolymer System Resin is profound new naval stores, and light trigger and monomer are all from Tianjin Jiu new material limited company, and auxiliary agent is derived from Changxing Chemical Material (Zhuhai) Co., Ltd..
The evaluation methodology of ink composite:
1st, curable
For the curable of ink composite, using 22 μm of bar spreaders, the Photocurable composition preparing is coated in base On material.Coated sample is installed on tape, conveys this sample under medium pressure mercury lamp.Quarter scraping is repeatedly pressed not produce the marking with fingernail For being fully cured standard, record does not produce the conveyor speeds the fastest of the marking.Therefore, conveyor speeds are faster, black liquid dry Dry property is better.
2nd, animal migration
Photocurable composition is fully cured by above-mentioned photo curing condition, the powder of certain mass under grinding respectively in curing system End, weighs, and can calculate the quality of light trigger by known proportioning；Powder is separately immersed in the acetonitrile of certain volume One month, carry out quantitation to identify using light-initiated and to the concentration of each dissolution using liquid chromatographic mass analysis, thus calculating Go out that how many light trigger moves in solution.The quality of the light trigger migrating out/theoretical light initiator quality=mobility.
3rd, cohesive
To the cured film being cured on each base material, use for reference the method for jis g3320 to be carved into latticed otch.Then, exist Adhesive tape is attached on cured film and is peeled off, thus observe the stripping situation of cured film.According to unstripped in every 100 grids The number of grid is evaluating the cohesive of cured film.More than 50/100 is available for practicality.
Evaluation result is as shown in the table:
Table 1
Table 2
Table 3
Table 4
For the light-curable ink described in embodiment, irradiated by ultraviolet light light source and obtain good curing performance, drying property Adhesive ability good, that low migration is good, can not only be applied to safety-sensitive, the toy of wholesomeness, various food Packaging material are additionally it is possible to be widely used in the packaging applicationss of sanitary equipment, cosmetics, pharmaceuticals etc..

Claims (9)

1. a kind of light-curable ink compositionss for food, medicine and cosmetic package are it is characterised in that be to draw containing light Send out agent, acrylate monomer, the resin oligomers with polymer-based group, polymerism phosphonate compound curable compositions.
2. compositionss according to claim 1 are it is characterised in that described light trigger is selected from formula i compound:
Wherein:
Each r1Independently selected from: hydrogen, halogen, c1-c12 alkyl, c3-c6 cycloalkyl, c1-c12 alkoxyl；
r2And r3Each is independently selected from hydrogen, halogen, c1-c18 alkyl, c3-c6 cycloalkyl, c1-c18 alkoxyl；
r4Selected from hydrogen, halogen, c1-c12 alkyl, c1-c12 alkoxyl；
X is 2-6 or c1-c18 alkoxyl independently selected from the residue of polyhydric alcohol, wherein hydroxyl value；
N=0 or 1；
M number is 1-6；
And/or formula ii compound:
Wherein:
A+b=n, 2≤n≤6, n is integer, and a, b are the integer more than or equal to 1；
r1、r2Identical or different, it is independently selected from the alkyl of c1-c4；
X is selected from o, s, nr3；
r3Selected from h, c1-c10 alkyl, aryl, aralkyl, alkaryl；
L is selected from the residue of the residue, the residue of multiamino compound or many sulfhydryl compounds of aliphatic polyhydroxy compound, hydroxyl The number of base, amino or sulfydryl is n；
R be selected from ethylenic unsaturated functional group, preferred acrylate, substituted acrylate, methacrylate, styrene, Acrylamide, Methacrylamide, allyl ester.
3. compositionss according to claim 1 are it is characterised in that its consumption of described light trigger is selected from composition total weight 0.2 ~ 20 %.
4. compositionss according to claim 1 are it is characterised in that described acrylate monomer is bifunctional acrylate Monomer and the mixing of multi-functional acrylate's monomer.
5. compositionss according to claim 1 are it is characterised in that the content in described acrylate monomer compositions is selected from With respect to 10 ~ 75 % of composition total weight, wherein bifunctional acrylate's monomer accounts for the part by weight choosing of total mix monomer From 0.1 ~ 50%.
6. compositionss according to claim 1 are it is characterised in that described oligomer is selected from hyperbranched uv resin, polyester Acid esters, three official's polyester chloride acrylic esters, epoxy soybean oil acrylate, epoxy acrylate, modified epoxy acrylic ester and/ Or urethane acrylate, preferably hyperbranched uv resin, polyester acrylate, epoxy acrylate, modified epoxy acrylic ester, Urethane acrylate.
7. compositionss according to claim 1 are it is characterised in that content in ink composite for the described oligomer is selected from 10 ~ 80 % with respect to total composition.
8. compositionss according to claim 1 are it is characterised in that described polymerism phosphonate compound is total selected from compositionss The 0.1 ~ 10% of weight.
9. a kind of printed article, it is print obtained from ink composite any one of usage right requirement 1 ~ 8 is printed Brush thing.
CN201610775856.5A 2016-08-31 2016-08-31 Photo-cured printing ink composition for food, medicine and cosmetic package Pending CN106366755A (en)

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
CN110366584A (en) * 2017-02-24 2019-10-22 富士胶片株式会社 Light curable inks composition and image forming method
CN111662588A (en) * 2020-07-10 2020-09-15 河南功能高分子膜材料创新中心有限公司 UV gravure white ink for PETG heat shrinkable film label and preparation method thereof
CN113166573A (en) * 2018-11-28 2021-07-23 东洋油墨Sc控股株式会社 Active energy ray-curable inkjet ink, inkjet recorded matter, and method for producing inkjet recorded matter
US20210397088A1 (en) * 2020-06-19 2021-12-23 Canon Kabushiki Kaisha Photo-curable composition and methods for preparing cured film, optical component, circuit substrate, electrical component and replica mold using the same
CN116376438A (en) * 2023-02-28 2023-07-04 滁州金桥德克新材料有限公司 UV (ultraviolet) curing coating composition applied to galvanized sheet

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CN102199377A (en) * 2011-03-23 2011-09-28 长兴（广州）精细涂料有限公司 Ultraviolet curing processing agent
CN104262511A (en) * 2014-09-02 2015-01-07 天津久日化学股份有限公司 Novel polymerizable coinitiator and UV-curable composition
CN104892798A (en) * 2015-06-23 2015-09-09 天津久日化学股份有限公司 Novel thioxanthone photoinitiator and application of UV-LED (ultraviolet-light-emitting diode) light curing
CN104910131A (en) * 2015-06-23 2015-09-16 天津久日化学股份有限公司 New thioxanthone carboxylic ester photoinitiator and preparation method thereof

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CN101906095A (en) * 2010-07-06 2010-12-08 天津久日化学工业有限公司 Thioxathone-4-carboxylic ester and preparation method as well as photoinitiator composition and application
CN102199377A (en) * 2011-03-23 2011-09-28 长兴（广州）精细涂料有限公司 Ultraviolet curing processing agent
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110366584A (en) * 2017-02-24 2019-10-22 富士胶片株式会社 Light curable inks composition and image forming method
US11795334B2 (en) 2017-02-24 2023-10-24 Fujifilm Corporation Photo-curable ink composition and method for forming image
CN113166573A (en) * 2018-11-28 2021-07-23 东洋油墨Sc控股株式会社 Active energy ray-curable inkjet ink, inkjet recorded matter, and method for producing inkjet recorded matter
US20210397088A1 (en) * 2020-06-19 2021-12-23 Canon Kabushiki Kaisha Photo-curable composition and methods for preparing cured film, optical component, circuit substrate, electrical component and replica mold using the same
US11835858B2 (en) * 2020-06-19 2023-12-05 Canon Kabushiki Kaisha Photo-curable composition and methods for preparing cured film, optical component, circuit substrate, electrical component and replica mold using the same
CN111662588A (en) * 2020-07-10 2020-09-15 河南功能高分子膜材料创新中心有限公司 UV gravure white ink for PETG heat shrinkable film label and preparation method thereof
CN116376438A (en) * 2023-02-28 2023-07-04 滁州金桥德克新材料有限公司 UV (ultraviolet) curing coating composition applied to galvanized sheet
CN116376438B (en) * 2023-02-28 2023-11-10 金桥德克新材料股份有限公司 UV (ultraviolet) curing coating composition applied to galvanized sheet

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Application publication date: 20170201