WO2008003190A1 - Radiation curable adhesion promoter - Google Patents
Radiation curable adhesion promoter Download PDFInfo
- Publication number
- WO2008003190A1 WO2008003190A1 PCT/CN2006/003384 CN2006003384W WO2008003190A1 WO 2008003190 A1 WO2008003190 A1 WO 2008003190A1 CN 2006003384 W CN2006003384 W CN 2006003384W WO 2008003190 A1 WO2008003190 A1 WO 2008003190A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- radiation curable
- adhesion promoter
- adhesion
- groups
- adhesives
- Prior art date
Links
- 230000005855 radiation Effects 0.000 title claims abstract description 26
- 239000002318 adhesion promoter Substances 0.000 title claims abstract description 20
- 238000000576 coating method Methods 0.000 claims abstract description 14
- 239000000853 adhesive Substances 0.000 claims abstract description 12
- 230000001070 adhesive effect Effects 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 3
- 239000011248 coating agent Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 12
- 239000000976 ink Substances 0.000 abstract description 10
- 239000000758 substrate Substances 0.000 abstract description 7
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- HCZBMENVWKFZDJ-UHFFFAOYSA-N 3-trimethylsilylpropane-1-thiol Chemical compound C[Si](C)(C)CCCS HCZBMENVWKFZDJ-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical group CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Definitions
- This invention relates to a new type of radiation curable adhesion promoters, which can be applied to coatings, inks and adhesives to improve adhesion between cured materials and substrates. In particular they can be applied to radiation curable coatings and adhesives to promote adhesion between cured materials and substrates.
- Radiation curable materials have been developed rapidly in the past 20 years. They have been widely used in coatings, inks and adhesives etc since they provide high productivity, low energy consumption and zero environment pollution. Radiation curable materials are in general composed of four ingredients: oligomers, reactive monomers, photoinitiators and additives. Radiation curable materials are commonly first coated on the substrates, and cured via radiation resources (ultraviolet light or electron beam). The adhesion between the substrates and the cured radiation curable materials varies considerably from system to system. Adhesion promoters are the most common additives that improve adhesion between cured materials and substrates. The most common adhesion promoters are alkoxysilanes.
- Alkoxysilane adhesion promoters are generally polymerization inactive-can not participate in polymerization reactions of monomers and oligomers during curing. As a result, their levels in formulations are considerably limited.
- the only commonly used polymerizable alkoxysilane adhesion promoter in industry is methacryloxypropyl trimethoxysilane. However it contains a certain level of starting material-allylmethacrylate, which is a volatile and odorous compound. Therefore its applicability is limited. See Waldman, Silane Coupling Agents Improving Performance, Modern Paints and Coatings, February, 1996.
- WO 96/12749 discloses an oligomer containing alkoxysilanes and optical fiber coating containing the oligomer.
- the silane oligomers are high in molecular weight (500-11000) and a high level of silane oligomers in the composition is needed (5-99%).
- Such oligomers are typically polyurethane materials.
- this invention provides a radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilanes containing mercapto groups, with monomers containing two or more acrylate or methacrylate groups, in the presence of organic amine catalyst under mild conditions (for example at 65 0 C for one hour), as shown in Equation
- Above radiation curable adhesion promoter has (meth)acrylate at one end which is polymerable; and an alkoxysilane group at the other end which is adhesion promotive.
- the radiation curable adhesion promoter of this invention due to its polymerization activity, are unrestricted in quantity in their application to coatings, inks, and adhesives.
- HDDA hexane-l,6-diol diacrylate
- HDDA 12% hexane-l,6-diol diacrylate
- trimethlolpropane triacrylate (TMPTA)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
This invention relates to a new type of adhesion promoter, which in particular can be used in radiation curable coatings and adhesives. This adhesion promoter is obtained by fast reaction of alkoxysilanes containing mercapto groups, with monomers containing two or more acrylate or methacrylate groups, in the presence of organic amines under mild conditions. This adhesion promoter has adhesion promotive functional groups such as alkoxysilanes at one end, and polymerable groups of (meth)acrylate at the other end. The invention can be applied to coatings, inks and adhesives to improve adhesion between cured materials and substrates.
Description
RADIATION CURABLE ADHESION PROMOTER
Technical Field
This invention relates to a new type of radiation curable adhesion promoters, which can be applied to coatings, inks and adhesives to improve adhesion between cured materials and substrates. In particular they can be applied to radiation curable coatings and adhesives to promote adhesion between cured materials and substrates. Background Art
Radiation curable materials (including ultraviolet light curable materials and electron beam curable materials) have been developed rapidly in the past 20 years. They have been widely used in coatings, inks and adhesives etc since they provide high productivity, low energy consumption and zero environment pollution. Radiation curable materials are in general composed of four ingredients: oligomers, reactive monomers, photoinitiators and additives. Radiation curable materials are commonly first coated on the substrates, and cured via radiation resources (ultraviolet light or electron beam). The adhesion between the substrates and the cured radiation curable materials varies considerably from system to system. Adhesion promoters are the most common additives that improve adhesion between cured materials and substrates. The most common adhesion promoters are alkoxysilanes.
Alkoxysilane adhesion promoters are generally polymerization inactive-can not participate in polymerization reactions of monomers and oligomers during
curing. As a result, their levels in formulations are considerably limited. The only commonly used polymerizable alkoxysilane adhesion promoter in industry is methacryloxypropyl trimethoxysilane. However it contains a certain level of starting material-allylmethacrylate, which is a volatile and odorous compound. Therefore its applicability is limited. See Waldman, Silane Coupling Agents Improving Performance, Modern Paints and Coatings, February, 1996.
On May 2, 1996, WO 96/12749 discloses an oligomer containing alkoxysilanes and optical fiber coating containing the oligomer. The silane oligomers are high in molecular weight (500-11000) and a high level of silane oligomers in the composition is needed (5-99%). Such oligomers are typically polyurethane materials.
On the other hand, US patent US6391463B1 discloses a new polymerisable alkoxysilane monomer, which is obtained by hydrosilylation reactions. Disclosure of Invention
Aiming at above-mentioned shortcomings of current technologies, it is an object of this invention to provide an easily made and industrialized new adhesion promoter, which is polymerizable and can be widely applied to radiation curable coatings, inks, and adhesives at high contents.
In order to solve above technical problems, this invention provides a radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilanes containing mercapto groups, with monomers containing two or more acrylate or methacrylate groups, in the presence of organic amine catalyst
under mild conditions (for example at 650C for one hour), as shown in Equation
1 :
(R1
Equation 1
Above radiation curable adhesion promoter has (meth)acrylate at one end which is polymerable; and an alkoxysilane group at the other end which is adhesion promotive.
In contrast to current techniques, the radiation curable adhesion promoter of this invention due to its polymerization activity, are unrestricted in quantity in their application to coatings, inks, and adhesives. Particularly in radiation curable coatings, inks and adhesives use of above adhesion promoters in large quantities can greatly change adhesion power between cured materials and substrates. Modes for Carrying Out the Invention
This invention will be further described with following illustrative examples: Example 1
According to Equation 1, 19.6g of 3-mercapto propyl trimethylsilane, 22.6g
of hexane-l,6-diol diacrylate and O.lg of diethylamine were added into a dry and clean reactor. The mixture was heated to 650C under uniform stirring. 3-mercapto propyl trimethylsilane was completely reacted according to testing by gas chromatography. The resulting colorless liquid was radiation curable adhesion promoter A. Example 2-UV curable coating
50% aromatic polyurethane acrylate oligomer (RMAT 650)
42% hexane-l,6-diol diacrylate (HDDA)
3% 1 -hydroxy cyclohexyl phenyl ketone (Irgacure 184)
1% 2,4,6-trimethylρhenol (Irganox 1010)
4% radiation curable adhesion promoter A
Above ingredients were added successively into a reactor. After agitation at 600C for two hours an UV curable coating was obtained via filtration. Its viscosity was 2100 cps at 250C. This UV curable coating has good bonding to glass, metals, and some plastics. Example 3-UV curable ink
45% aromatic polyurethane acrylate oligomer (RMAT 650)
12% hexane-l,6-diol diacrylate (HDDA)
20% trimethlolpropane triacrylate (TMPTA)
15% white color paste (55% titanium dioxide dispersed in TMPTA)
3% 1 -hydroxy cyclohexyl phenyl ketone (Irgacure 184)
1% 2,4,6-trimethylphenol (Irganox 1010)
4% radiation curable adhesion promoter A
Above ingredients were added successively into a reactor. After agitation at 600C for two hours an UV curable ink was obtained via filtration. Its viscosity was 1600 cps at 250C. This UV curable ink has good bonding to glass, metals, and some plastics. Other colored inks can be made in a similar way to above. Example 4-Radiation curable adhesive
50% radiation curable adhesion promoter A
47% isobornyl acrylate (IBOA)
3% 1 -hydroxycyclohexyl phenyl ketone (Irgacure 184)
Above ingredients were added successively into a reactor. After agitation at 600C for two hours an UV curable adhesive was obtained via filtration. Its viscosity was 400 cps at 250C. The adhesive can be used in bonding metals and glass etc. with very tight adhesion.
Claims
1. A radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilanes containing mercapto groups, with monomers containing two or more acrylate or methacrylate groups, in the presence of organic amine catalyst under mild conditions,
2. A radiation curable coating, which contains 0.1-60% radiation curable promoters of claim 1 or/ and 2.
3. A radiation curable adhesive, which contains 0.1-99% radiation curable promoters of claim 1 or/and 2.
4. A radiation curable ink, which contains 0.1-10% radiation curable promoters of claim 1 or/and 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2006100281180A CN101096473A (en) | 2006-06-26 | 2006-06-26 | Adhesive property promoter for radiation curing material |
| CN200610028118.0 | 2006-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008003190A1 true WO2008003190A1 (en) | 2008-01-10 |
Family
ID=38894170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2006/003384 WO2008003190A1 (en) | 2006-06-26 | 2006-12-13 | Radiation curable adhesion promoter |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN101096473A (en) |
| WO (1) | WO2008003190A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011023409A1 (en) | 2009-08-31 | 2011-03-03 | Byk-Chemie Gmbh | Adhesion promoter for coatings on different substrate surfaces |
| WO2020104302A1 (en) * | 2018-11-20 | 2020-05-28 | Agfa-Gevaert Nv | Radiation curable inkjet ink for manufacturing printed circuit boards |
| WO2021089358A1 (en) * | 2019-11-07 | 2021-05-14 | Agfa-Gevaert Nv | Radiation curable inkjet ink for manufacturing printed circuit boards |
| US11028214B2 (en) | 2018-01-22 | 2021-06-08 | Corning Incorporated | Synthesis of oligomer for optical fiber coating |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102140109A (en) * | 2010-09-08 | 2011-08-03 | 上海飞凯光电材料股份有限公司 | Radiation curing activated monomer with high adhesive force and application thereof |
| KR102661529B1 (en) * | 2021-11-30 | 2024-04-26 | 한국생산기술연구원 | Adhesive materials and their use |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5318850A (en) * | 1991-11-27 | 1994-06-07 | General Electric Company | UV curable abrasion-resistant coatings with improved weatherability |
| JP2001261741A (en) * | 2000-03-16 | 2001-09-26 | Kansai Paint Co Ltd | Curable composition and method for forming coating film of the composition |
| US6706779B2 (en) * | 2000-05-12 | 2004-03-16 | Dow Corning Corporation | Radiation curable compositions containing alkenyl ether functional polyisobutylenes |
| US6818133B1 (en) * | 1998-09-10 | 2004-11-16 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Semipermeable membranes |
-
2006
- 2006-06-26 CN CNA2006100281180A patent/CN101096473A/en active Pending
- 2006-12-13 WO PCT/CN2006/003384 patent/WO2008003190A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5318850A (en) * | 1991-11-27 | 1994-06-07 | General Electric Company | UV curable abrasion-resistant coatings with improved weatherability |
| US6818133B1 (en) * | 1998-09-10 | 2004-11-16 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Semipermeable membranes |
| JP2001261741A (en) * | 2000-03-16 | 2001-09-26 | Kansai Paint Co Ltd | Curable composition and method for forming coating film of the composition |
| US6706779B2 (en) * | 2000-05-12 | 2004-03-16 | Dow Corning Corporation | Radiation curable compositions containing alkenyl ether functional polyisobutylenes |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011023409A1 (en) | 2009-08-31 | 2011-03-03 | Byk-Chemie Gmbh | Adhesion promoter for coatings on different substrate surfaces |
| US8778458B2 (en) | 2009-08-31 | 2014-07-15 | Byk-Chemie Gmbh | Adhesion promoter for coatings on different substrate surfaces |
| US9593246B2 (en) | 2009-08-31 | 2017-03-14 | Byk-Chemie Gmbh | Object or an article whose surface is provided with a coating produced using and adhesion promoter |
| US11028214B2 (en) | 2018-01-22 | 2021-06-08 | Corning Incorporated | Synthesis of oligomer for optical fiber coating |
| WO2020104302A1 (en) * | 2018-11-20 | 2020-05-28 | Agfa-Gevaert Nv | Radiation curable inkjet ink for manufacturing printed circuit boards |
| JP2022511422A (en) * | 2018-11-20 | 2022-01-31 | アグフア－ゲヴエルト，ナームローゼ・フエンノートシヤツプ | Radiation-curable inkjet ink for manufacturing printed circuit boards |
| WO2021089358A1 (en) * | 2019-11-07 | 2021-05-14 | Agfa-Gevaert Nv | Radiation curable inkjet ink for manufacturing printed circuit boards |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101096473A (en) | 2008-01-02 |
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