CN109553733B - Synthetic method and application of UV-curable maleated rosin acrylate resin - Google Patents
Synthetic method and application of UV-curable maleated rosin acrylate resin Download PDFInfo
- Publication number
- CN109553733B CN109553733B CN201811414219.0A CN201811414219A CN109553733B CN 109553733 B CN109553733 B CN 109553733B CN 201811414219 A CN201811414219 A CN 201811414219A CN 109553733 B CN109553733 B CN 109553733B
- Authority
- CN
- China
- Prior art keywords
- weight
- acrylate
- parts
- resin
- rosin
- 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.)
- Active
Links
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 91
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 91
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 34
- 238000010189 synthetic method Methods 0.000 title claims abstract description 5
- 229910000679 solder Inorganic materials 0.000 claims abstract description 46
- 239000011347 resin Substances 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 32
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims abstract description 16
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 (methyl) hydroxyethyl (propyl) acrylate Chemical compound 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 36
- 239000003112 inhibitor Substances 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 34
- 239000003085 diluting agent Substances 0.000 claims description 33
- 239000003504 photosensitizing agent Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000000945 filler Substances 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 17
- 239000004408 titanium dioxide Substances 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 16
- 238000000227 grinding Methods 0.000 claims description 16
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 238000004321 preservation Methods 0.000 claims description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 5
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 5
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 claims description 2
- 229940044119 2-tert-butylhydroquinone Drugs 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- 150000007527 lewis bases Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- NOZAVIHXELGKOE-UHFFFAOYSA-J [C+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C Chemical group [C+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C NOZAVIHXELGKOE-UHFFFAOYSA-J 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 238000007039 two-step reaction Methods 0.000 abstract description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 56
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 28
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 15
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical group O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 15
- 239000012752 auxiliary agent Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 14
- 238000007599 discharging Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000004383 yellowing Methods 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 238000005476 soldering Methods 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 238000002310 reflectometry Methods 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000003466 welding Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
-
- 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
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a synthetic method and application of a maleic rosin acrylate resin capable of being cured by UV, and belongs to the technical field of ultraviolet curing resins. The main raw materials comprise maleic rosin, (methyl) hydroxyethyl (propyl) acrylate and glycidyl (methyl) acrylate, and the resin is prepared by two-step reaction, the resin contains a rigid condensed multi-alicyclic structure, has better heat resistance and is not yellowed at high temperature, carboxyl is generated by grafting anhydride and hydroxyethyl methacrylate, terminal double bonds are introduced, the generated carboxyl is used for reacting with the glycidyl methacrylate, the terminal double bonds are further introduced, the flexibility of the resin product is endowed by the introduction of an acrylate carbon chain, the ultraviolet light curing performance of the resin is ensured by the introduction of two terminal C ═ C double bonds, and the prepared maleic rosin acrylate resin is prepared into the ultraviolet light curing white solder resist ink.
Description
Technical Field
The invention belongs to the technical field of ultraviolet curing resin, and particularly relates to a synthetic method and application of a maleic rosin acrylate resin capable of being cured by UV.
Background
The white solder resist ink is a special functional material printed on a circuit board of an LED product, and mainly plays roles in solder resist and light reflection. As is well known, white light reflection has the highest efficiency, so that light loss can be greatly reduced, and the light source can save more energy. However, most white ink turns yellow after soldering, and because the temperature in the soldering process is higher than 288 ℃, ordinary solder resist ink cannot bear the temperature, and the light loss is increased due to the fact that the lamp panel is attractive due to yellowing of the surface of the lamp panel and the fire is caused. The method is in line with the requirements of the white solder resist ink on the welding resistance, the yellowing resistance and the mechanical property, the white solder resist ink used in the market at present is mainly photosensitive imaging type, the photosensitive imaging type white solder resist ink needs to obtain the part needing soldering by a developing method, the application process is complex, and the production cost is high; when the photo-curing white solder resist ink is used, a curing film can be obtained only by printing and exposure, the production process is simple, the cost is saved, and meanwhile, the electricity is saved.
The photo-curing white solder resist ink used in the market at present is less, and the cured film layer has poor mechanical property and is far inferior to a photosensitive imaging type in high temperature resistance and yellowing resistance. In order to prepare the high-performance photo-curing white solder resist ink, firstly, a high-temperature-resistant and yellowing-resistant UV resin needs to be synthesized, and meanwhile, a proper active diluent, a proper photoinitiator and the like are selected, so that the solder resistance, the yellowing resistance and the mechanical property of the ink meet the requirements.
Rosin and its derivatives are common natural resins, and maleic rosin is also called maleic anhydride rosin, which is a product obtained by the addition reaction of rosin and maleic anhydride (maleic anhydride), and after the addition reaction, conjugated double bonds disappear, and the tendency of oxidative discoloration is reduced, so the resin can be used for manufacturing light-colored oil-based resin paint. The rosin-based rigid condensed multi-element alicyclic structure has high heat resistance and is not yellowed at high temperature. The maleic acid modified rosin ester resin can be mixed with a plurality of resins and used for screen printing ink to improve the heat resistance, hardness, gloss and the like of a system. However, no rosin-modified resin which can be cured by UV has been reported.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a synthesis method and application of a maleic rosin acrylate resin capable of being cured by UV, the maleic rosin acrylate resin prepared by the invention has better high temperature resistance and yellowing resistance, and the maleic rosin acrylate resin is applied to white solder resist ink, so that the ink product has the excellent performances of quick curing, low shrinkage, high gloss, good adhesion, high temperature resistance and yellowing resistance.
The invention provides a maleic rosin acrylate resin capable of being cured by UV, which has a chemical structural general formula as follows:
wherein n is 2 or 3, R1Is H or CH3，R2Is H or CH3。
The invention provides a synthesis method of the UV-curable maleated rosin acrylate resin, which comprises the following steps:
step 1: mixing maleated rosin and acrylate derivative, heating to dissolve, adding a polymerization inhibitor and a catalyst, and carrying out heat preservation reaction until the acid value reaches a theoretical value;
step 2: adding glycidyl acrylate or glycidyl methacrylate into the product obtained in the step (1), continuously adding a catalyst and a polymerization inhibitor, and carrying out heat preservation reaction until the acid value reaches a theoretical value;
and step 3: cooling the product obtained in the step 2 to obtain maleic rosin acrylate resin;
wherein the acrylate derivative is one or more of hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate or hydroxypropyl methacrylate.
Further, in the step 1, the molar weight ratio of the maleated rosin to the acrylate derivative is 1: 2-1: 10.
Further, in the steps 1 and 2, the temperature of heating, dissolving and heat preservation reaction is 90-120 ℃.
Further, in steps 1 and 2, the catalyst comprises a lewis base.
Further, in steps 1 and 2, the catalyst is any one of triphenylphosphine and p-toluenesulfonic acid.
Further, in steps 1 and 2, the polymerization inhibitor comprises any one or more of Hydroquinone (HQ), p-benzoquinone (PBQ), methyl hydroquinone (THQ), p-hydroxyanisole (hqme), 2-tert-butylhydroquinone (MTBHQ), and 2, 5-di-tert-butylhydroquinone (2, 5-DTBHQ).
Further, in the steps 1 and 2, the amount of the catalyst is 0.1-1 wt% of the amount of the resin.
Further, in the step 1, the amount of the polymerization inhibitor is 0.1 to 1 wt% of the acrylate derivative, and in the step 2, the amount of the polymerization inhibitor is 0.1 to 1 wt% of the glycidyl acrylate or the glycidyl methacrylate.
Furthermore, in the step 2, the feeding amount of the glycidyl acrylate or the glycidyl methacrylate is 0.1-0.5 of the molar amount of the maleated rosin.
Further, in step 3, the temperature is reduced to below 50 ℃.
The invention also provides a white solder resist ink, and the raw materials of the white solder resist ink comprise the maleic rosin acrylate resin, an active diluent, a photoinitiator, titanium dioxide and a filler.
Further, the white solder resist ink comprises: based on the weight portion, the weight portion of the material,
the invention provides a preparation method of the white solder resist ink, which comprises the steps of uniformly mixing the raw materials, and then grinding the mixture until the fineness is less than 8 mu m to obtain the white solder resist ink.
The invention provides the white solder resist ink which mainly plays roles of solder resist and light reflection on the circuit board of the LED product.
By the scheme, the invention at least has the following advantages:
1. the maleic rosin acrylate resin is prepared by two-step reaction by using maleic rosin, hydroxyethyl (propyl) methacrylate and glycidyl methacrylate as main raw materials, contains a rigid fused multi-alicyclic structure, has good heat resistance and does not yellow at high temperature. The carboxyl is generated by grafting anhydride and hydroxyethyl (propyl) acrylate (methyl) to introduce a terminal double bond, the generated carboxyl is used for reacting with glycidyl (methyl) acrylate to further introduce the terminal double bond, the introduction of an acrylate carbon chain endows the resin with flexibility, and the introduction of a terminal C ═ C double bond ensures the ultraviolet curing performance of the resin.
2. According to the invention, a maleic rosin structure is introduced with two terminal C ═ C double bonds, so that the maleic rosin acrylate resin capable of being cured by UV is synthesized, and the blank that the rosin derivative can not be applied to the field of ultraviolet light curing is filled. 3. The natural structure of the maleated rosin, namely the rigid condensed multielement alicyclic structure, is utilized, the structure ensures that the product has better heat resistance and is not yellowed at high temperature, the synthesized resin is used for ultraviolet curing white ink, the requirements of high temperature resistance and yellowing resistance of the ink in a welding-resistant process are met, and the ink product is endowed with excellent performances of quick curing, low shrinkage, high gloss, good adhesion, high temperature resistance and yellowing resistance.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention.
The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.
The active diluent is EM231/EM2380/EM2382 provided by Changxing chemistry; the photosensitizer is a mixture of Irgacure184 and TPO produced by Ciba specialty Chemicals, and the mixing ratio is 1: 1-4; the titanium dioxide is DuPont R-706; the filler is talcum powder GD-25 produced by Xinnuxier mining Co.
Acid value: the number of milligrams of potassium hydroxide required to neutralize the acid in 1g of product is in mgKOH/g.
Example 1
(1) Putting 1 part by weight of maleic rosin and 1 part by weight of hydroxyethyl methacrylate into a reaction kettle according to a molar weight ratio of 1:5, heating to 110 ℃ for dissolution, adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine), keeping the temperature at 110 ℃ for reaction until the acid value reaches 107, and taking excessive hydroxyethyl methacrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 10 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and carrying out heat preservation reaction at 110 ℃ until the acid value reaches 100; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (DuPont R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 2
(1) Putting 1 part by weight of maleic rosin and hydroxypropyl acrylate into a reaction kettle according to a molar weight ratio of 1:5, heating to 110 ℃ for dissolution, keeping the temperature of 110 ℃ for reaction until the acid value reaches 107 by using 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine), and taking excessive hydroxypropyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 20 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and carrying out heat preservation reaction at 110 ℃ until the acid value reaches 94; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (DuPont R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 3
(1) Putting 1 part by weight of maleic rosin and 1 part by weight of hydroxypropyl methacrylate into a reaction kettle according to a molar weight ratio of 1:5, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxypropyl methacrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 30 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphorus) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and carrying out heat preservation reaction at 110 ℃ until the acid value reaches 87; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (DuPont R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 4
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl acrylate in a molar weight ratio of 1:5 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 40 percent of maleated rosin, 0.001 part of supplementary catalyst (triphenyl phosphorus) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and carrying out heat preservation reaction at 110 ℃ until the acid value reaches 81; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 5
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl acrylate in a molar weight ratio of 1:5 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 75; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 6
(1) Putting 1 part by weight of maleic rosin and 1 part by weight of hydroxyethyl methacrylate in a reaction kettle according to a molar weight ratio of 1:6, heating to 110 ℃ to dissolve, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 95, and taking excessive hydroxyethyl methacrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 67; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 7
(1) Putting 1 part by weight of maleic rosin and 1 part by weight of hydroxyethyl methacrylate in a reaction kettle according to a molar weight ratio of 1:7, heating to 110 ℃ to dissolve, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 86, and taking excessive hydroxyethyl methacrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 61; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 8
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl methacrylate in a molar weight ratio of 1:8 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 80, and taking excessive hydroxyethyl methacrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 56; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 9
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl methacrylate in a molar weight ratio of 1:9 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 72, and taking excessive hydroxyethyl methacrylate as a system diluent;
(2) adding glycidyl acrylate with the molar weight of the maleic rosin of 50 percent, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and carrying out heat preservation reaction at 110 ℃ until the acid value reaches 51; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 10
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl acrylate in a molar weight ratio of 1:5 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 75; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) Taking 25 parts by weight of the resin prepared in the step (2), 30 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness is less than 8 mu m to prepare the white solder resist ink capable of being cured by ultraviolet light.
Example 11
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl acrylate in a molar weight ratio of 1:5 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 75; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 30 parts by weight of the resin prepared in the step (2), 25 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
Example 12
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl acrylate in a molar weight ratio of 1:5 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 75; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) Taking 35 parts of the resin prepared in the step (2), 20 parts of reactive diluent (Changxing EM231), 25 parts of titanium dioxide (Du R-706), 15 parts of filler (talcum powder GD-25), 1 part of photosensitizer (Irgacure184), 2 parts of photosensitizer (TPO) and 2 parts of auxiliary agent (KS66) according to parts by weight, uniformly mixing, and grinding by a three-roll machine until the fineness is less than 8 mu m to prepare the white solder resist ink capable of being cured by ultraviolet light.
Example 13
(1) Putting 1 part of maleic rosin and 1 part of hydroxyethyl acrylate in a molar weight ratio of 1:5 into a reaction kettle, heating to 110 ℃ to dissolve the maleic rosin, and adding 0.003 part of polymerization inhibitor (p-methyl phenol) and 0.01 part of catalyst (triphenyl phosphine). Keeping the temperature at 110 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl acrylate as a system diluent;
(2) adding glycidyl methacrylate with the molar weight of 50 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and keeping the temperature at 110 ℃ until the acid value reaches 75; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) Taking 45 parts by weight of the resin prepared in the step (2), 20 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (Du R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll mill until the fineness of the mixture is less than 8 mu m to prepare the white solder resist ink capable of being cured by ultraviolet light
Example 14
(1) Putting 1 part by weight of maleic rosin and 1 part by weight of hydroxyethyl methacrylate into a reaction kettle according to a molar weight ratio of 1:5, heating to 90 ℃ to dissolve the maleic rosin, adding 0.008 part by weight of polymerization inhibitor (p-methyl phenol) and 0.005 part by weight of catalyst (triphenyl phosphine), keeping the temperature at 90 ℃ to react until the acid value reaches 107, and taking excessive hydroxyethyl methacrylate as a system diluent;
(2) adding glycidyl acrylate with the molar weight of 10 percent of maleic rosin, 0.001 part of supplementary catalyst (triphenyl phosphine) and 0.001 part of polymerization inhibitor (p-methyl phenol) into the reaction product prepared in the step (1), and carrying out heat preservation reaction at 110 ℃ until the acid value reaches 100; and cooling to below 50 ℃ and discharging to obtain the UV-cured maleic rosin acrylate resin.
(3) And (3) taking 40 parts by weight of the resin prepared in the step (2), 15 parts by weight of reactive diluent (Changxing EM231), 25 parts by weight of titanium dioxide (DuPont R-706), 15 parts by weight of filler (talcum powder GD-25), 1 part by weight of photosensitizer (Irgacure184), 2 parts by weight of photosensitizer (TPO) and 2 parts by weight of auxiliary agent (KS66) to be uniformly mixed, and grinding the mixture by a three-roll machine until the fineness of the mixture is less than 8 mu m to prepare the white ultraviolet-curable solder resist ink.
The ultraviolet curing white solder resist ink prepared in the examples 1 to 13 is printed on a single-sided copper clad laminate by 200-mesh screen printing, and is irradiated for 40 to 60 seconds by ultraviolet light (with the maximum absorption wavelength of 365nm) of a high-pressure mercury lamp at room temperature, and the adhesive force, the glossiness, the reflectivity, the soldering resistance and the yellowing resistance of the film are tested after the film is cured. The test items, indexes and methods are detailed in table 1, and the test results are respectively shown in tables 2, 3 and 4:
TABLE 1 test items according to the invention and corresponding test methods and indexes
TABLE 2 influence of molar ratio of maleated rosin and hydroxyethyl methacrylate on UV-curable white solder resist ink
TABLE 3 influence of molar ratio of maleated rosin and glycidyl methacrylate on UV-curable white solder resist ink
TABLE 4 influence of amount of addition of maleated rosin-modified acrylate resin to ink on UV-curable white solder resist ink
According to the test results in table 2, it can be seen that when the proportion of hydroxyethyl (meth) acrylate as a diluent in the system is higher, the viscosity of the ink product is reduced, the thickness of the printed film is reduced, and the reflectivity is affected; in addition, the crosslinking density of the product is greatly influenced, so that the adhesive force is reduced, the soldering resistance is reduced, and the comprehensive performance of the system is deviated.
According to the test results in table 3, when the ratio of glycidyl methacrylate is increased, the total amount of double bonds at the terminal of the resin is increased, the adhesive force of the ink is improved, and the comprehensive performance is excellent.
According to the test results in table 4, it can be seen that, for the determined maleic rosin modified acrylate resin finished product, the amount of the product in the ink formula system is increased, and the adhesion, the glossiness and the reflectivity of the paint film can be obviously improved.
In combination with the above examples, only example 10 had poor adhesion and resistance to solder blistering.
Therefore, the maleic rosin acrylate resin capable of being cured by UV, which is prepared by the invention, can be used for ultraviolet curing white solder resist ink, and outstanding performance can be obtained.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (9)
1. A synthetic method of maleic rosin acrylate resin capable of being cured by UV is characterized in that: the method comprises the following steps:
step 1: mixing maleated rosin and acrylate derivative, heating to dissolve, adding a polymerization inhibitor and a catalyst, and carrying out heat preservation reaction until the acid value reaches a theoretical value;
step 2: adding glycidyl acrylate or glycidyl methacrylate into the product obtained in the step (1), continuously adding a catalyst and a polymerization inhibitor, and carrying out heat preservation reaction until the acid value reaches a theoretical value;
and step 3: cooling the product obtained in the step 2 to obtain maleic rosin acrylate resin;
wherein the acrylate derivative is one or more of hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate or hydroxypropyl methacrylate;
the chemical structural general formula of the UV-curable maleated rosin acrylate resin is as follows:
wherein n is 2 or 3, R1Is H or CH3，R2Is H or CH3。
2. The method of synthesis according to claim 1, characterized in that: in the step 1, the molar weight ratio of the maleated rosin to the acrylate derivative is 1: 2-1: 10.
3. The method of synthesis according to claim 1, characterized in that: in steps 1 and 2, the catalyst is a lewis base.
4. The method of synthesis according to claim 1, characterized in that: in the steps 1 and 2, the polymerization inhibitor is any one or more of hydroquinone, p-benzoquinone, methyl hydroquinone, p-hydroxyanisole, 2-tert-butylhydroquinone and 2, 5-di-tert-butylhydroquinone.
5. The method of synthesis according to claim 1, characterized in that: in the step 2, the feeding amount of the glycidyl acrylate or the glycidyl methacrylate is 0.1-0.5 of the molar weight of the maleated rosin.
6. A white solder resist ink is characterized by comprising the maleated rosin acrylic ester resin prepared by the method of any one of claims 1 to 5, a reactive diluent, a photosensitizer, titanium dioxide and a filler.
7. The white solder mask ink of claim 6, wherein the white solder mask ink comprises: based on the weight portion, the weight portion of the material,
8. a method for preparing a white solder resist ink according to claim 6 or 7, characterized in that: and uniformly mixing the raw materials, and then grinding the mixture until the fineness of the mixture is less than 8 mu m to obtain the white solder resist ink.
9. An LED product circuit board or an LED lamp containing the white solder mask ink of claim 6 or 7 or the white solder mask ink prepared by the preparation method of claim 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811414219.0A CN109553733B (en) | 2018-11-26 | 2018-11-26 | Synthetic method and application of UV-curable maleated rosin acrylate resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811414219.0A CN109553733B (en) | 2018-11-26 | 2018-11-26 | Synthetic method and application of UV-curable maleated rosin acrylate resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109553733A CN109553733A (en) | 2019-04-02 |
| CN109553733B true CN109553733B (en) | 2021-12-28 |
Family
ID=65867261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811414219.0A Active CN109553733B (en) | 2018-11-26 | 2018-11-26 | Synthetic method and application of UV-curable maleated rosin acrylate resin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109553733B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6663124B1 (en) * | 2019-07-24 | 2020-03-11 | 千住金属工業株式会社 | Modified rosin, flux for soldering and solder paste |
| CN110746528A (en) * | 2019-10-29 | 2020-02-04 | 四会市邦得利化工有限公司 | Method for preparing maleic rosin hydroxyethyl methacrylate polymer from rosin |
| CN111394018B (en) * | 2020-04-27 | 2021-11-02 | 四川省新康意新材料科技有限公司 | Oil stain-resistant EVA hot melt adhesive with good anti-aging performance and preparation method thereof |
| CN111978784B (en) * | 2020-09-15 | 2022-03-04 | 中山市富日印刷材料有限公司 | Preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104194643A (en) * | 2014-09-28 | 2014-12-10 | 广州宏昌胶粘带厂 | Fumaric rosin bi-2-(acryloyl oxygen) ethyl ester, as well as preparation method and application thereof |
| CN107602768A (en) * | 2017-09-29 | 2018-01-19 | 郑州大学 | A kind of modified rosin base UV light-cured resins and its preparation method and application |
| CN108219676A (en) * | 2016-12-22 | 2018-06-29 | 谭海剑 | A kind of special modified rosin resin, preparation method and its application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5212213A (en) * | 1990-10-26 | 1993-05-18 | Westvaco Corporation | Radiation-curable rosin-based resins |
-
2018
- 2018-11-26 CN CN201811414219.0A patent/CN109553733B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104194643A (en) * | 2014-09-28 | 2014-12-10 | 广州宏昌胶粘带厂 | Fumaric rosin bi-2-(acryloyl oxygen) ethyl ester, as well as preparation method and application thereof |
| CN108219676A (en) * | 2016-12-22 | 2018-06-29 | 谭海剑 | A kind of special modified rosin resin, preparation method and its application |
| CN107602768A (en) * | 2017-09-29 | 2018-01-19 | 郑州大学 | A kind of modified rosin base UV light-cured resins and its preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109553733A (en) | 2019-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109553733B (en) | Synthetic method and application of UV-curable maleated rosin acrylate resin | |
| JP6203874B2 (en) | White curable resin composition, cured product thereof, printed wiring board having the cured product, and reflector for light-emitting element comprising the cured product | |
| CN110078895B (en) | Toughening modified UV (ultraviolet) light-cured epoxy acrylate resin and preparation method thereof | |
| JP5892221B2 (en) | (Meth) acryloyl group-containing resin, curable composition, cured product thereof, and resist material | |
| JP5479821B2 (en) | Solder resist layer and printed wiring board | |
| CN108034041B (en) | Alkali-soluble photocuring epoxy resin containing cinnamic acid or coumarin group, preparation method thereof and solder resist prepared from resin | |
| CN110615865A (en) | Resin for high-temperature-resistant low-yellowing solder-resistant UV (ultraviolet) ink and preparation method thereof | |
| JP2015531753A (en) | Ketocoumarins as photoinitiators and photosensitizers in inks | |
| WO2007123017A1 (en) | Polymerizable unsaturated compound and method for producing the same | |
| EP1829909B1 (en) | Method for producing branched polyether resin composition and method for producing acid-pendant branched polyether resin composition | |
| CN105061671A (en) | Liquid photosensitive solder-resist resin for LED and preparation method thereof | |
| JP6402967B2 (en) | (Meth) acryloyl group-containing resin, method for producing (meth) acryloyl group-containing resin, curable resin material, cured product thereof, and resist material | |
| JP6402968B2 (en) | (Meth) acryloyl group-containing resin, method for producing (meth) acryloyl group-containing resin, curable resin material, cured product thereof, and resist material | |
| JPH0411626A (en) | Resin composition, solder resist resin composition, and cured product | |
| JP2015168775A (en) | Acid group-containing (meth)acrylate resin, production method of acid group-containing (meth)acrylate resin, curable resin material, cured product of the same, and resist material | |
| JP4389137B2 (en) | Photocurable resin composition | |
| JP7324595B2 (en) | Black photosensitive resin composition, cured product thereof, and rigid flexible printed wiring board | |
| JP4684435B2 (en) | Unsaturated polyester compound, method for producing the same, and curable composition | |
| JPH01278585A (en) | Ultraviolet ray curable resist ink | |
| CN115819361B (en) | Modified TGIC auxiliary agent for UV photosensitive solder resist ink and preparation method thereof | |
| JP6476559B2 (en) | Acid group-containing (meth) acrylate resin, method for producing acid group-containing (meth) acrylate resin, curable resin material, cured product thereof, and resist material | |
| JP4606223B2 (en) | Ultraviolet curable resin composition and cured coating film thereof | |
| JP2004143455A (en) | Polyester-(meth)acrylate | |
| JPS5929246A (en) | Composition for forming ultraviolet-cured pattern | |
| JP2006137738A (en) | Terpene-based (meth)acrylic acid ester and its curable composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230201 Address after: No. 18, Huacheng Road, Industrial Concentration Zone, Qingyang Town, Jiangyin City, Wuxi City, Jiangsu Province 214400 Patentee after: JIANGSU KUANGSHUN PHOTOSENSITIVITY NEW-MATERIAL STOCK Co.,Ltd. Address before: 214400 east of Jiasheng South Road and west of Yangtze River Avenue, Jiangyin Lingang Economic Development Zone, Wuxi City, Jiangsu Province Patentee before: JIANGYIN GUANGYU PHOTOSENSITIVE MATERIALS CO.,LTD. |