CN108181788A - Photosensitive polymer combination - Google Patents
Photosensitive polymer combination Download PDFInfo
- Publication number
- CN108181788A CN108181788A CN201711236139.6A CN201711236139A CN108181788A CN 108181788 A CN108181788 A CN 108181788A CN 201711236139 A CN201711236139 A CN 201711236139A CN 108181788 A CN108181788 A CN 108181788A
- Authority
- CN
- China
- Prior art keywords
- mass parts
- photosensitive polymer
- polymer combination
- ingredient
- ammonium salt
- 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
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- 229920000642 polymer Polymers 0.000 title claims abstract description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000004615 ingredient Substances 0.000 claims abstract description 72
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 57
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 51
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 44
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 38
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 36
- 239000000440 bentonite Substances 0.000 claims abstract description 20
- 229910000278 bentonite Inorganic materials 0.000 claims abstract description 20
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 239000003085 diluting agent Substances 0.000 claims abstract description 16
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 239000011630 iodine Substances 0.000 claims abstract description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 64
- 239000003822 epoxy resin Substances 0.000 claims description 62
- -1 free radical Compound Chemical class 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims description 5
- 238000000016 photochemical curing Methods 0.000 claims description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 3
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- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 235000003642 hunger Nutrition 0.000 claims description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 230000021523 carboxylation Effects 0.000 claims 1
- 238000006473 carboxylation reaction Methods 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 238000005507 spraying Methods 0.000 abstract description 25
- 238000000576 coating method Methods 0.000 abstract description 24
- 239000011248 coating agent Substances 0.000 abstract description 22
- 230000035945 sensitivity Effects 0.000 abstract description 17
- 150000002118 epoxides Chemical class 0.000 abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 34
- 239000002585 base Substances 0.000 description 18
- 239000004020 conductor Substances 0.000 description 18
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
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- 230000001681 protective effect Effects 0.000 description 8
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- 230000000052 comparative effect Effects 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 3
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical group CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 3
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 3
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- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical class C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
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- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
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- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Abstract
The present invention provides a kind of photosensitive polymer combination, the photosensitive polymer combination for applying thicker even with spray coating method, it may have excellent sensitivity, and turned-down edge can be prevented, so as to form the cured coating film of excellent appearance.Photosensitive polymer combination contains：(A) photoresist containing carboxyl；(B) Photoepolymerizationinitiater initiater；(C) reactive diluent；(D) epoxide；(E) quaternary ammonium salt represented by the following general formula (I) treated bentonite, [R is utilized1R2R3R4‑N]+X‑(I) in formula, R1、R2、R3、R4The saturated aliphatic hydrocarbons that carbon number is 1~25 or the unsaturated fatty hydrocarbons base that carbon number is 2~25 are each independently represented, X represents the halogen in fluorine, chlorine, bromine and iodine；And (F) hydrophobic silica, relative to 100 mass parts of the photoresist containing carboxyl of (A) ingredient, containing 4.5 mass parts~20 (F) hydrophobic silicas described in mass parts.
Description
Technical field
The present invention relates to suitable for covering material, such as being covered in printed circuit board substrate formed conductor circuit figure
The photosensitive polymer combination of the covering material of case, make the photosensitive polymer combination cure after solidfied material and covered with this
The printed circuit board of solidfied material.
Background technology
Electronic component is equipped on to the weldering of the pattern for the formation conductor circuit pattern on substrate and by being brazed
Disk covers pad using printed circuit boards such as flexible printed circuit board, rigid circuit boards, and using protective film (such as solder mask)
Circuit part in addition.As a result, when electronic component is welded in printed circuit board, solder attachment is prevented in unnecessary portion
Point, and circuit conductor to be prevented to be directly exposed in air be corroded due to oxidation, humidity.
In addition, it is sometimes than previous general thickness (10 μm~25 μm left sides by the conductor design for forming conductor circuit pattern
It is right) thick (35 μm or more, such as 50 μm~100 μm of thickness).When the shape on the printed circuit board with thicker conductor circuit
Into solder mask when protective films, correspondingly, it is also necessary to the film thickness (such as 60 μm~110 μm thickness) of protective film is thickeied,
Therefore, it is necessary to apply thicker by photosensitive polymer combination (such as 70 μm~150 μm thickness).
Therefore, it is proposed to the stacking knot that light-cured type solder mask is formed as being made of lower floor's solder resist and upper strata solder resist
The printed circuit board (patent document 1) of structure.
But as described in Patent Document 1, if using as the photosensitive polymer combination of the raw material of protective film apply compared with
Thickness, then ultraviolet light is difficult to reach the deep of film when causing due to the thickness of film in ultraviolet exposure, and accordingly, there exist ask as follows
Topic：The sensitivity (particularly film bottom near sensitivity) of film is insufficient, can not obtain fine definition and good sometimes
Linearity configuration.
Furthermore, it is contemplated that it is operational, photosensitive polymer combination is coated on printed circuit board sometimes with spray coating method.But
It is that, if applying thicker by photosensitive polymer combination as described above using spray coating method, there are the following problems：It is applying
Turned-down edge is led to the problem of in film, the problem of good appearance of film can not be obtained.
Existing technical literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2010-129575 bulletins
Invention content
The subject that the invention solves
In view of said circumstances, the purpose of the present invention is to provide photosensitive polymer combination, have the photoresist group
The circuit boards such as the printed circuit board of photocuring film of object are closed, apply the photosensitive polymer combination even with spray coating method
It is thicker, it can also be formed with excellent sensitivity, the cured coating film of turned-down edge and excellent appearance can be prevented.
Means for solving the problems
The solution of the present invention is a kind of photosensitive polymer combination, is contained：(A) photoresist containing carboxyl (with
Under, sometimes referred to as " photoresist containing carboxyl of (A) ingredient "), be with free-radical polymerised unsaturated group and
The glycidyl compound of epoxy group and the carboxyl of the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid
The reaction product reacted and generated, the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid is polyacid
Or its acid anhydrides and free-radical polymerised unsaturated monocarboxylic epoxy resin hydroxyl reaction and the compound that generates, the freedom
Base polymerism unsaturated monocarboxylic epoxy resin be have in 1 molecule the multi-functional epoxy resin of 2 or more epoxy groups with
The reaction product of free-radical polymerised unsaturated monocarboxylic；(B) Photoepolymerizationinitiater initiater；(C) reactive diluent；(D) epoxidation
Close object；(E) using the quaternary ammonium salt represented by the following general formula (I) treated bentonite (hereinafter, being sometimes referred to as the " utilization of E ingredients
Quaternary ammonium salt treated bentonite "),
[R1R2R3R4-N]+X- (I)
(in formula, R1、R2、R3、R4It is 2~25 to each independently represent saturated aliphatic hydrocarbons that carbon number is 1~25 or carbon number
Unsaturated fatty hydrocarbons base, X represent the halogen in fluorine, chlorine, bromine and iodine.)；And (F) hydrophobic silica, relative to
The photoresist containing carboxyl of above-mentioned (A) ingredient of 100 mass parts, containing 4.5 mass parts~20 mass parts above-mentioned (F) dredge
Aqueous silica.
In said program, since the photoresist containing carboxyl of (A) ingredient is that have free-radical polymerised insatiable hunger
With group and the glycidyl compound of epoxy group further with the free-radical polymerised unsaturated monocarboxylic of modified by polyacid
The chemical constitution that the carboxyl reaction of epoxy resin forms, therefore, has the characteristic that photonasty is improved.In addition, " 100 mass
Photoresist of the part containing carboxyl " represents the mass parts of the solid constituent of the photoresist containing carboxyl.
The solution of the present invention is a kind of photosensitive polymer combination, wherein, relative to above-mentioned (A) ingredient of 100 mass parts
Photoresist containing carboxyl, containing 5.0 mass parts~20 mass parts above-mentioned (E) ingredient treated using quaternary ammonium salt
Bentonite.
The solution of the present invention is a kind of photosensitive polymer combination, wherein, relative to above-mentioned (A) ingredient of 100 mass parts
Photoresist containing carboxyl, containing 5.5 mass parts~13.5 mass parts above-mentioned (F) hydrophobic silica, relative to
The photoresist containing carboxyl of above-mentioned (A) ingredient of 100 mass parts, containing 8.0 mass parts~18 mass parts above-mentioned (E) into
Point utilize quaternary ammonium salt treated bentonite.
The solution of the present invention is a kind of photosensitive polymer combination, wherein, after the utilization quaternary ammonium salt treatment of above-mentioned (E) ingredient
Bentonitic quality：The value of the quality of above-mentioned (F) hydrophobic silica is 1.0：0.30~3.0 range.
The solution of the present invention is a kind of photosensitive polymer combination, wherein, above-mentioned (F) hydrophobic silica is utilizes alkane
Silica after base silicyl (alkylsilyl) modification.
The solution of the present invention is a kind of photosensitive polymer combination, wherein, above-mentioned quaternary ammonium salt is distearyl dimethyl ammonium
Salt.
The solution of the present invention is the photocured product of above-mentioned photosensitive polymer combination.
The solution of the present invention is circuit board, the photocuring film with above-mentioned photosensitive polymer combination.
Invention effect
Scheme according to the present invention contains carboxyl using above-mentioned (A) ingredient of characteristic being improved with photonasty
Photoresist as the photoresist containing carboxyl, and be combined with (E) ingredient using quaternary ammonium salt, that treated is swollen
Profit soil and be the mass parts of 4.5 mass parts~20 relative to the photoresist containing carboxyl of 100 mass parts (A) ingredient
(F) hydrophobic silica, thus, it is possible to obtain following photosensitive polymer combination：It is applied even with spray coating method
Thicker photosensitive polymer combination, it may have excellent sensitivity, and turned-down edge can be prevented, so as to form excellent appearance
Cured coating film.
Scheme according to the present invention relative to the photoresist containing carboxyl of 100 mass parts (A) ingredient, is combined with
(E) ingredient of the mass parts of 5.0 mass parts~20 using quaternary ammonium salt treated bentonite, so as to even with spray coating method
The photosensitive polymer combination for applying thicker will not be damaged excellent sensitivity, be reliably prevented from collapsing for film
Side, and can further improve the appearance of cured coating film.
Scheme according to the present invention relative to the photoresist containing carboxyl of (A) ingredient of 100 mass parts, contains
The profit of (E) ingredient of the mass parts of (F) hydrophobic silica of the mass parts of 5.5 mass parts~13.5 and 8.0 mass parts~18
With quaternary ammonium salt treated bentonite, so as to even with the photosensitive polymer combination that spray coating method applies thicker, also not
It can be damaged excellent sensitivity, turned-down edge can be prevented and harmonious can improve appearance of film well.
Scheme according to the present invention, (E) ingredient utilize quaternary ammonium salt treated bentonitic quality：(F) hydrophobicity two
The value of the quality of silica is 1.0：0.30~3.0, thus, it is possible to obtain following photosensitive polymer combination：Even with
The photosensitive polymer combination that spray coating method applies thicker is also reliably prevented from turned-down edge, and can form excellent appearance
Cured coating film.
Scheme according to the present invention, (F) hydrophobic silica are the silica after being modified using aIkylsilyl groups,
So as to even with the photosensitive polymer combination that spray coating method applies thicker, can also be more reliably prevented from collapsing for film
Side.
Scheme according to the present invention, quaternary ammonium salt is distearyl dimethyl ammonium, thus, it is possible to obtain following photonasty tree
Oil/fat composition：Turned-down edge can be more reliably prevented from, so as to form the cured coating film of excellent appearance.
Specific embodiment
Next, the photosensitive polymer combination of the present invention is carried out as described below.The photosensitive resin composition of the present invention
Object contains：(A) photoresist containing carboxyl is that the shrink with free-radical polymerised unsaturated group and epoxy group is sweet
Oil-based compounds are reacted with the carboxyl of the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid and are generated anti-
Product is answered, the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid is polyacid or its acid anhydrides and freedom
The hydroxyl reaction of base polymerism unsaturated monocarboxylic epoxy resin and the compound generated, the free-radical polymerised unsaturation
Mono-carboxylic acid's epoxy resin be have in 1 molecule the multi-functional epoxy resin of 2 or more epoxy groups with it is free-radical polymerised not
The reaction product of saturation monocarboxylic acid；(B) Photoepolymerizationinitiater initiater；(C) reactive diluent；(D) epoxide；(E) using by
Quaternary ammonium salt treated the bentonite that the following general formula (I) represents,
[R1R2R3R4-N]+X- (I)
(in formula, R1、R2、R3、R4It is 2~25 to each independently represent saturated aliphatic hydrocarbons that carbon number is 1~25 or carbon number
Unsaturated fatty hydrocarbons base, X represent the halogen in fluorine, chlorine, bromine and iodine.)；And (F) hydrophobic silica, relative to
The photoresist containing carboxyl of above-mentioned (A) ingredient of 100 mass parts, containing 4.5 mass parts~20 mass parts above-mentioned (F) dredge
Aqueous silica.
(A) photoresist containing carboxyl of ingredient
(A) photoresist containing carboxyl of ingredient is the resin obtained as follows：Make acrylic acid, methacrylic acid (with
Down sometimes referred to as " (methyl) acrylic acid ".) etc. there are 2 or more epoxies in free-radical polymerised unsaturated monocarboxylic and 1 molecule
At least part epoxy reaction of the multi-functional epoxy resin of base, thus to obtain free radicals such as epoxy (methyl) acrylate
Polymerism unsaturated monocarboxylic epoxy resin makes polyacid or its acid anhydrides and the free-radical polymerised unsaturated monocarboxylic of generation
Change the hydroxyl reaction of epoxy resin, thus to obtain modified by polyacid radical polymerizations such as modified by polyacid epoxy (methyl) acrylate
Conjunction property unsaturated monocarboxylic epoxy resin, and make the contracting with 1 or more free-radical polymerised unsaturated group and epoxy group
Water glycerine based compound and a part of carboxylic of the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid obtained
Base reacts, thus to obtain the photoresist containing carboxyl of (A) ingredient.
The photoresist containing carboxyl of (A) ingredient joined together, is logical in the photosensitive polymer combination of the present invention
Crossing reacts glycidyl compound and the carboxyl of the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid,
Free-radical polymerised unsaturated group is further introduced into the free-radical polymerised unsaturated monocarboxylic asphalt mixtures modified by epoxy resin of modified by polyacid
The side chain of fat, therefore, compared with the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid, of the invention is photosensitive
Property resin have excellent photobehavior.
Therefore, in order to be designed to be in the conductor for being used to form conductor circuit pattern it is thicker (thickness be 35 μm or more, such as
50 μm~100 μm of thickness) printed circuit board on form the protective film of film thickness thicker (such as thickness be 60 μm~110 μm),
And photosensitive polymer combination is applied thicker (such as thickness is 70 μm~150 μm), and nonetheless, the sensitivity of film
(sensitivity particularly near film bottom) is also excellent, therefore, it is possible to obtain with fine definition and good linearity configuration
Cured coating film.
For above-mentioned multi-functional epoxy resin, as long as epoxy resin more than 2 functions, then can use any more officials
It can property epoxy resin.The epoxide equivalent of multi-functional epoxy resin is not particularly limited, preferably 3000 hereinafter, more preferably
For 2000 hereinafter, particularly preferably 100~500.For multi-functional epoxy resin, for example, can enumerate biphenyl type epoxy resin,
Rubber modified epoxy resins, the ε such as naphthalene type epoxy resin, dicyclopentadiene type epoxy resin, modifying epoxy resin by organosilicon-oneself in
Phenol novolak type epoxy resins, the o-cresol phenolic aldehyde such as ester modified epoxy resin, bisphenol A-type, bisphenol-f type, bisphenol-A D types are clear
The multi-functional asphalt mixtures modified by epoxy resin of the cresol novolak type epoxy resins such as paint shaped, phenol novolak type epoxy resin, bisphenol A novolac type epoxy resin, annular aliphatic
The multi-functional epoxy resin of fat, glycidyl ester type, glycidic amine type polyfunctional epoxy resin, the multi-functional ring of hetero ring type
Oxygen resin, bis-phenol modified novolac type epoxy resin, multi-functional modified novolac type epoxy resin, phenols are with having phenol
Condensation product type epoxy resin of aromatic aldehyde of property hydroxyl etc..The halogen such as Br, Cl are imported in these resins alternatively, it is also possible to use
Product obtained from plain atom.Above-mentioned multi-functional epoxy resin is can be used alone, what can also be mixed with two or more is upper
State multi-functional epoxy resin.
Free-radical polymerised unsaturated monocarboxylic is not particularly limited, for example, can enumerate acrylic acid, methacrylic acid,
Crotonic acid, cinnamic acid etc., preferably acrylic acid, methacrylic acid.It can be used alone above-mentioned free-radical polymerised unsaturated single carboxylic
Acid, the above-mentioned free-radical polymerised unsaturated monocarboxylic that can also be used in mixed way on 2 kinds.
The reaction method of multi-functional epoxy resin and free-radical polymerised unsaturated monocarboxylic is not particularly limited,
It such as can be by being carried out in appropriate diluent to multi-functional epoxy resin and free-radical polymerised unsaturated monocarboxylic
It heats and reacts them.
Polyacid or multi-anhydride are for passing through above-mentioned multi-functional epoxy resin and free-radical polymerised unsaturated list
The reaction of carboxylic acid and generate hydroxyl reaction, so that the carboxyl to dissociate is introduced into resin.Polyacid or its acid anhydrides are had no
It is particularly limited to, saturation, undersaturated polyacid or its acid anhydrides can use.For polyacid, such as succinic acid, horse can be enumerated
Come sour, adipic acid, citric acid, phthalic acid, tetrahydrophthalic acid, 3- methyl tetrahydrophthalic acid, 4- methyl tetrahydrochysenes
Phthalic acid, 3- ethyls tetrahydrophthalic acid, 4- ethyls tetrahydrophthalic acid, hexahydrophthalic acid, 3- methyl six
Hydrogen phthalic acid, 4- methylhexahydrophthaacid acids, 3- ethyls hexahydrophthalic acid, 4- ethyls hexahydrophthalic acid,
Methyl tetrahydrophthalic acid, methylhexahydrophthaacid acid, endo-methylene group tetrahydrophthalic acid, methylendomethylene tetrahydrochysene
Phthalic acid, trimellitic acid, Pyromellitic Acid and diglycolic acid etc. as multi-anhydride, can enumerate above-mentioned polyacid
Acid anhydrides.Above compound is can be used alone, the above compound that can also be mixed with two or more.
The free-radical polymerised unsaturated group and the glycidyl compound of epoxy group that have 1 or more are had no
Be particularly limited to, for example, can enumerate glycidyl acrylate, glycidyl methacrylate, allyl glycidyl ether,
Pentaerythritol triacrylate monoglycidyl ether, pentaerythritol acrylate trimethyl monoglycidyl ether etc..It needs to illustrate
, can have multiple glycidyls in 1 molecule.Above-mentioned has 1 or more free-radical polymerised unsaturated group
It can be used alone, can also be mixed with two or more with the compound of epoxy group.
The acid value of the photoresist containing carboxyl of (A) ingredient is not particularly limited, it is contemplated that reliably carry out
Alkali development, lower limiting value are preferably 30mgKOH/g, particularly preferably 40mgKOH/g.On the other hand, from preventing by alkaline developer
From the aspect of caused exposure portion dissolving, the upper limit value of acid value is preferably 200mgKOH/g, from the moisture-proof for preventing solidfied material
From the aspect of the deterioration of electrical characteristics, particularly preferably 150mgKOH/g.
In addition, the matter average molecular weight of the photoresist containing carboxyl of (A) ingredient is not particularly limited, from curing
From the aspect of the obdurability and dry to touch of object, lower limiting value is preferably 3000, and particularly preferably 5000.The opposing party
Face, from the aspect of smoothly alkali-developable, the upper limit value of matter average molecular weight is preferably 200000, and particularly preferably 50000.
(B) Photoepolymerizationinitiater initiater
It, can be with as long as Photoepolymerizationinitiater initiater used in general, is not particularly limited for Photoepolymerizationinitiater initiater
Use any Photoepolymerizationinitiater initiater.Specifically, ethyl ketone can be for example enumerated, 1- [9- ethyls -6- (2- methyl benzoyls) -9H-
Carbazole -3- bases] -1- (O- acetyl group oxime), bis- (2,4,6- trimethylbenzoyls) phosphine oxides of phenyl, benzoin, benzoin first
Base ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethyl
Aminoacetophenone, 2,2- dimethoxy -2- phenyl acetophenones, 2,2- diethoxy -2- phenyl acetophenones, 2- methyl -4 '-(first
Sulfenyl) -2- morphlinophenyls ethyl ketone, 2- hydroxy-2-methyl -1- phenyl-propane -1- ketone, 1- hydroxycyclohexylphenylketones,
4- (2- hydroxyl-oxethyls) phenyl -2- (hydroxyl -2- propyl) ketone, benzophenone, to phenyl benzophenone, 4,4 '-diethyl amino
Base benzophenone, dichloro benzophenone, 2-methylanthraquinone, 2- ethyl hydrazine, 2- tertiary butyls anthraquinone, 2- amino anthraquinones, 2- methyl
Thioxanthones, 2- ethyls thioxanthones, 2-chlorothioxanthone, 2,4- dimethyl thioxanthones, 2,4- diethyl thioxanthones, benzil dimethyl
Ketal, acetophenone dimethyl ketal, p- dimethyl amino benzoate etc..Above-mentioned substance is can be used alone, can also be mixed
It closes and uses above-mentioned substance of more than two kinds.
The content of Photoepolymerizationinitiater initiater is not particularly limited, for example, containing relative to 100 mass parts (A) ingredient
The photoresist (solid constituent, same as below) of carboxyl, the mass parts of preferably 5 mass parts~20.
(C) reactive diluent
Reactive diluent is, for example, photopolymerization monomer, is the chemical combination that every 1 molecule at least has 1 polymeric double bond
Object, preferably every 1 molecule at least have the compound of 2 polymeric double bonds.In order to make the photocuring of photosensitive polymer combination
The solidfied material with acid resistance, heat resistance, alkali resistance etc. is fully obtained, uses reactive diluent.
As long as reactive diluent above compound, is not particularly limited, such as can enumerate methacrylic acid 2-
Hydroxy methacrylate, phenoxyethyl methacrylate, diethylene glycol monomethyl acrylate, acrylic acid 2- hydroxyl -3- phenoxy-propyls,
1,4- butanediols two (methyl) acrylate, 1,6-HD two (methyl) acrylate, neopentyl glycol two (methyl) acrylic acid
Ester, diethylene glycol (DEG) two (methyl) acrylate, NPGA neopentyl glycol adipate two (methyl) acrylate, hydroxy new pentane acid neopentyl glycol
Two (methyl) acrylate, Bicvclopentyl two (methyl) acrylate, caprolactone modification double cyclopentenyl two (methyl) acrylic acid
Ester, ethylene-oxide-modified di(2-ethylhexyl)phosphate (methyl) acrylate, allylation cyclohexyl two (methyl) acrylate, isocyanuric acid ester
Two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, two (trimethylolpropane) four (methyl) acrylic acid
Ester, dipentaerythritol three (methyl) acrylate, dipentaerythritol three (methyl) acrylate, pentaerythrite three (methyl) propylene
Acid esters, epoxy pronane modification trimethylolpropane tris (methyl) acrylate, three (acryloyl-oxyethyl) isocyanuric acid esters, third
Modified dipentaerythritol five (methyl) acrylate of acid, dipentaerythritol six (methyl) acrylate, two season penta of caprolactone modification
Tetrol six (methyl) acrylate, carbamate (methyl) esters of acrylic acid etc..Above-mentioned substance is can be used alone, it can also
The above-mentioned substance being mixed with two or more.
The content of reactive diluent is not particularly limited, for example, (A) ingredient relative to 100 mass parts contains
There is a photoresist of carboxyl, the mass parts of preferably 2.0 mass parts~200, the mass parts of particularly preferably 10 mass parts~100.
(D) epoxide
Epoxide is used to improve the crosslink density of solidfied material to obtain the solidfied material with sufficient intensity, such as can lift
Go out epoxy resin.As epoxy resin, such as biphenyl type epoxy resin, bisphenol A type epoxy resin, novolaks type ring can be enumerated
Oxygen resin (phenol novolak type epoxy resin, o-cresol Novolac type epoxy resin, p-tert-butylphenol phenolic varnish type
Deng), epichlorohydrin is made to be reacted with Bisphenol F, bisphenol S and is obtained bisphenol-f type, bisphenol-s epoxy resin and with oxidation hexamethylene
Alicyclic epoxy resin, the isocyanuric acid three (2,3- glycidyl) of alkenyl, oxidation adamantyl, cyclopentene oxide base etc.
Ester, isocyanuric acid triglycidyl group three (2- hydroxyethyls) ester etc. have the triglycidyl isocyanurate, double of triazine ring
Cyclopeutadiene type epoxy resin, adamantane type epoxy resin.Above compound is can be used alone, 2 kinds can also be used in mixed way
Above above compound.
The content of epoxide is not particularly limited, is examined in terms of the film that sufficient intensity is obtained after the curing
Consider, for example, the photoresist containing carboxyl of (A) ingredient relative to 100 mass parts, the matter of preferably 10 mass parts~200
Measure part, the mass parts of particularly preferably 20 mass parts~100.
(E) ingredient utilizes quaternary ammonium salt treated bentonite
By utilizing quaternary ammonium salt treated swelling with what aftermentioned (F) hydrophobic silica coordinated (E) ingredient together
Soil, so as to, the photosensitive polymer combination for being applied even with spray coating method thicker can also prevent turned-down edge, so as to
Enough form the cured coating film of excellent appearance.
(E) ingredient using quaternary ammonium salt, treated that bentonite is utilizes the quaternary ammonium salt treatment represented by the following general formula (I)
Bentonite afterwards,
[R1R2R3R4-N]+X- (I)
(in formula, R1、R2、R3、R4It is 2~25 to each independently represent saturated aliphatic hydrocarbons that carbon number is 1~25 or carbon number
Unsaturated fatty hydrocarbons base, X represent the halogen in fluorine, chlorine, bromine and iodine.).
The R of quaternary ammonium salt1、R2、R3、R4As long as saturated aliphatic hydrocarbons or carbon number that respectively carbon number is 1~25 are 2~25
Unsaturated fatty hydrocarbons base, be not particularly limited, but from be reliably prevented turned-down edge and formed excellent appearance curing apply
From the aspect of film, preferably with carbon number be 1~5 saturated aliphatic hydrocarbons and carbon number be 7~22 saturated aliphatic hydrocarbons
Quaternary ammonium salt, particularly preferably with carbon number be 1~2 saturated aliphatic hydrocarbons and carbon number be 15~20 saturated aliphatic hydrocarbons
Quaternary ammonium salt.
As the concrete example of quaternary ammonium salt, VARISOFT TA100, distearyl ditallowdimethyl ammonium bromide etc. can be enumerated
Stearyl trimethyls ammonium salt, the moons such as distearyl dimethyl ammonium, stearyl trimethyl ammonium chloride, stearyl trimethyl ammonium bromide
The lauryl trimethyls ammonium salts such as osmanthus base trimethyl ammonium chloride, lauryl trimethyl ammonium bromide, INCROQUAT TMC-80,
The behenyl trimethyl ammonium salts such as behenyl ammonium bromide, Quaternium 24, dioctyl dimethyl
Dioctyl dimethyls ammonium salt such as ammonium bromide etc..In above-mentioned substance, the curing of excellent appearance is formed from turned-down edge is more reliably prevented from
From the aspect of film, the preferred distearyls dimethyl such as VARISOFT TA100, distearyl ditallowdimethyl ammonium bromide
Ammonium salt.
For (E) ingredient, using quaternary ammonium salt, treated that bentonitic content is not particularly limited, for example, relative to
The photoresist containing carboxyl of (A) ingredient of 100 mass parts, from the aspect of turned-down edge is reliably prevented, lower limiting value
Preferably 5.0 mass parts, from the aspect of the spreadability near the conductors such as copper foil is improved, lower limiting value is particularly preferably 8.0
Mass parts.In addition, the photoresist containing carboxyl of (A) ingredient relative to 100 mass parts, from make spraying become easily,
And from the aspect of securely maintaining excellent cured coating film appearance, upper limit value is preferably 20 mass parts, particularly preferably 18 matter
Measure part.
(F) hydrophobic silica
By with above-mentioned (E) ingredient, using quaternary ammonium salt, treated that bentonite coordinates (F) hydrophobicity titanium dioxide together
Silicon, so as to even with the photosensitive polymer combination that spray coating method applies thicker, can also prevent turned-down edge, and then can
Form the cured coating film of excellent appearance.
Hydrophobic silica is, for example, to the hydrophilic silicon oxides with silanol group using hydrophobic compound
Surface carries out the silica after silicic acid anhydride, which is spherical or approximate sphericity particle.As thin
Aqueous silica, such as can enumerate and utilize the organosilicons such as silane compound, the silicone compounds as hydrophobic compound
Compound, the aerosil obtained to silicon tetrachloride through flame hydrolysis (fumed silica), white carbon (silica
) etc. aerogel the surface of fine particle silicas carries out the product obtained by silicic acid anhydride.As having for above-mentioned hydrophobic compound
Organic silicon compound, such as methacryloxypropyl silane, methylchlorosilane, dimethyldichlorosilane, two silicon of hexamethyl can be enumerated
Azane, dimethyl siloxane, Trimethoxyoctylsilane, methacryl base silane, acryl silane etc..Wherein, from i.e.
Make be the photosensitive polymer combination for applying thicker using spray coating method also it is possible to more reliably prevent the turned-down edge of film in terms of examine
Consider, the hydrophobic silica after being modified preferably by aIkylsilyl groups to surface.
The primary particle size of hydrophobic silica is not particularly limited, from the aspect of dispersibility, preferably 3nm
~100nm, particularly preferably 5nm~50nm.In addition, the BET specific surface area for hydrophobic silica is not particularly limited,
Such as preferably 50m2/ g~500m2/g。
Relative to 100 mass parts of photoresist containing carboxyl of (A) ingredient, the content of hydrophobic silica is
The mass parts of 4.5 mass parts~20.Using spray coating method by the present invention photosensitive polymer combination apply it is thicker in the case of,
Relative to the photoresist containing carboxyl of 100 mass parts (A) ingredient, if less than 4.5 mass parts, it sometimes can not be abundant
Turned-down edge is prevented, if it exceeds 20 mass parts, then the appearance of excellent cured coating film can not be obtained sometimes with spray coating method.In addition,
Relative to the photoresist containing carboxyl of 100 mass parts (A) ingredient, the lower limiting value of the content of hydrophobic silica is preferred
For 5.5 mass parts, relative to the photoresist containing carboxyl of 100 mass parts (A) ingredient, the content of hydrophobic silica
Upper limit value be preferably 13.5 mass parts.
In addition, it will not make from the photosensitive polymer combination for applying thicker even with spray coating method excellent sensitive
Degree it is impaired and prevent turned-down edge and it is harmonious improve appearance of film well from the aspect of, relative to 100 mass parts (A) ingredient
Photoresist containing carboxyl preferably comprises the hydrophobic silica of the mass parts of 5.5 mass parts~13.5 and contains 8.0
(E) ingredient of the mass parts of mass parts~18 utilizes quaternary ammonium salt treated bentonite.
The ratio of quaternary ammonium salt treated bentonitic quality and the quality of hydrophobic silica is utilized for (E) ingredient
Rate is not particularly limited, and is also reliably prevented from from the photosensitive polymer combination for applying thicker even with spray coating method
Turned-down edge is formed from the aspect of the cured coating film of excellent appearance, and (E) ingredient utilizes quaternary ammonium salt treated bentonitic matter
Amount：The quality of hydrophobic silica is preferably 1.0：0.30~3.0, more preferably 1.0：0.50~2.5, particularly preferably
1.0：0.80~1.5.
It, can be according to need other than above-mentioned (A) ingredient~(F) ingredient in the photosensitive polymer combination of the present invention
It wants and coordinates various composition, such as the non-reactive diluents such as colorant, various additives, organic solvent, filler can be coordinated
Deng.
Colorant is not particularly limited, for example, as white color agents, the inorganic pigments such as titanium oxide can be enumerated, is made
For the colorant other than white, the yellow such as the cyan colorants such as the green colourants such as phthalocyanine green, phthalocyanine blue, anthraquinone system can be enumerated and
The inorganic pigments such as the black colorants such as the organic pigments such as toner, carbon black.
For various additives, such as the antifoaming agent, dispersant, silicon of silicon-type, hydrocarbon system and acrylic acid series etc. can be enumerated
Coupling agent, boron trifluoride-amine complex, dicyandiamide (DICY) and its derivative of methane series, titanate esters system and alumina series etc. have
Machine acid hydrazides, diaminomaleonitrile (DAMN) and its derivative, guanamines and its derivative, melamine and its derivative, amination
Metal salt, the alkene of the acetylacetone,2,4-pentanediones such as potentialities curing agent, zinc acetylacetonate and the chromium acetylacetonate such as acid imide (AI) and polyamines
The imidazoles such as amine, tin octoate, season sulfonium salt, triphenylphosphine, 2-mercaptobenzimidazole, imidazole salt and triethanolamine borate
Wait thixotropic agent such as thermosetting accelerators, polycarboxylic acids amide etc..
Filler helps to improve the physical strength of the film of photosensitive polymer combination, for example, can enumerate talcum, barium sulfate,
Silica, aluminium oxide, aluminium hydroxide, mica etc..
Non-reactive diluent is used to adjust the drying property of photosensitive polymer combination, coating viscosity, such as can enumerate
Solvent.For organic solvent, such as the ketones such as methyl ethyl ketone, cyclohexanone can be enumerated；The fragrance such as toluene, dimethylbenzene, durol
Race's hydro carbons；Methyl cellosolve, ethyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether,
The glycol ethers such as diethylene glycol monomethyl ether, carbiphene, dihydroxypropane single-ethyl ether, triethylene glycol monoethyl ether；Acetic acid
Ethyl ester, butyl acetate, cellosolve acetate, diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether acetate, propylene glycol list first
The esters such as the carboxylate of base ether acetic acid ester and above-mentioned glycol ethers；Alcohols such as ethyl alcohol, propyl alcohol, ethylene glycol, propylene glycol etc..
The manufacturing method of above-mentioned photosensitive polymer combination is not limited to specific method, such as can be to provide ratio
After example coordinates above-mentioned each ingredient, make above-mentioned each ingredient mixing dispersion using three rollers at room temperature and manufacture photonasty
Resin combination.Furthermore it is possible to it is pre-mixed before above-mentioned mixing dispersion using blender as needed.
Next, user's rule of the photosensitive polymer combination of the present invention is illustrated.Here, with will be of the invention
The method that is applied as the insulating protective film (such as solder mask etc.) of printed circuit board of photosensitive polymer combination be
Example illustrates.
By spray (flush coater method) for example with being etched to copper foil the circuit pattern that is formed (such as leading
The thickness of the copper foil of body is 50 μm or more) substrate, i.e. on printed circuit board, make the photonasty of the invention obtained as described above
Wet-film thickness when resin combination is formed as 60 μm or more using required thickness, such as thickness of dry film is 70 μm or more of thickness
Degree, is applied and forms film.Next, contain the non-reactive diluents such as organic solvent in photosensitive polymer combination
In the case of, in order to which non-reactive diluent is made to volatilize, carry out heating 15 minutes~60 at a temperature of 60 DEG C~80 DEG C or so
The predrying of or so minute, is consequently formed tack-free film.
Next, on the film after having carried out predrying, bonding is with the position other than the pad for causing circuit pattern
The minus film (photomask) of pattern with translucency, and ultraviolet light is irradiated from the upper side (for example, wavelength is 300~400nm's
Range).Then, non-exposed areas corresponding with above-mentioned pad is removed using dilute alkaline aqueous solution, thus develop film.For aobvious
Image method is then using spray-on process, spray process etc., as used dilute alkaline aqueous solution, such as can enumerate the matter of 0.5 mass %~5
Measure the aqueous sodium carbonate of %.Next, drying machine using heated air circulation type etc. carried out at 130 DEG C~170 DEG C 20 minutes~
The rear curing of 80 minutes, thus, it is possible to form the insulating protective films such as the solder mask as target on a printed circuit.
In addition, as coating method, can replace spraying (flush coater method) and use silk-screen printing, bar coater, applicator,
Other well known coating methods such as scraper plate coating machine, blade coating machine, roll coater, gravure coating machine.
Embodiment
Next, being illustrated to the embodiment of the present invention, but as long as without departing from its purport, the present invention is not limited to this
A little examples.
Examples 1 to 7, comparative example 1~7
Each ingredient shown in table 1 below is coordinated with the ratio shown in table 1 below, is made at room temperature using three rollers
Thus the mixing dispersion of each ingredient prepares Examples 1 to 7, the photosensitive polymer combination used in comparative example 1~7.Then,
The photosensitive polymer combination being prepared is applied in the following manner and makes test film.Number in table 1 below
Represent mass parts.In addition, the empty column in table 1 below represents unmated.
【Table 1】
In addition, the details about each ingredient in table 1, as described below.
(A) photoresist containing carboxyl of ingredient
Make cresol novolak type epoxy resin (Sumitomo Chemical Company Ltd's manufacture, the ESCN- of 220 mass parts
220, epoxide equivalent 220) and the acrylic acid of 72 mass parts be dissolved in the carbitol acetate of 250 mass parts, returning it
It is reacted under stream mode, thus to obtain cresol novolak type epoxy acrylate.Next, six by 138.6 mass parts
Hydrogen phthalic anhydride is added in obtained cresol novolak type epoxy acrylate, it is made to carry out back flow reaction, until
Until acid value reaches theoretical value, then add in the glycidyl methacrylate of 56.8 mass parts and make them further anti-
Should, thus to obtain the photoresist containing carboxyl, the i.e. synthetic resin (A-1) of (A) ingredient that solid constituent is 65 mass %.
(B) Photoepolymerizationinitiater initiater
·IRGACURE 907：BASF Amada Co., Ltd.s
·KAYACURE DETX：Nippon Kayaku K. K
(C) reactive diluent
·DPHA：Toagosei Co., Ltd
(D) epoxide
·EPICOAT 828、YX-4000K：Mitsubishi chemical Co., Ltd
(E) ingredient utilizes quaternary ammonium salt treated bentonite
·THIXOGEL VP：United Catalyst Corporation
(F) hydrophobic silica
·AEROSIL R974：Surface is modified using dimetylsilyl, Japanese AEROSIL Co., Ltd.
Filler
Barium sulfate B-34：Sakai Chemical Industry Co., Ltd.
·FH105：Talcum Co., Ltd. of Fuji
Colorant
·Fastogen Green：DIC Corporation
Various additives
Melamine：Nissan Chemical Ind Ltd
·DICY-7：Japanese epoxy resin Co., Ltd.
·Antage MB：Chemical industry Co., Ltd. of Kawaguchi
·Disperbyk-103、BYK-410：Bi Ke chemistry Amada Co., Ltd.
Non-reactive diluent
·PMA：Chemical conversion product Co., Ltd. of Sanyo
(A) photoresist containing carboxyl other than ingredient
·Ripoxy SP-4621：Showa Denko K. K
(E) quaternary ammonium salt treated bentonite is utilized other than ingredient
·THIXOGEL LG：United Catalyst Corporation
Hydrophilic silicon oxides
AEROSIL #380：Japanese AEROSIL Co., Ltd.
Test film production process
Substrate：Printed circuit board (glass epoxy substrate " FR-4 ", plate thickness 1.6mm, conductor (Cu foils) thickness for 18 μm~
90μm)
Substrate surface process：Polishing
Coating：Spraying
Coating condition：Spray volume (110cc/min), transmission speed (2.3m/min), disc rotation speed (30000rpm) apply voltage
(-35KV)
Wet-film thickness：100 μm~110 μm
Predrying：80 DEG C, 20 minutes
Exposure：On photosensitive polymer combination, 300mJ/cm2(dominant wavelength 365nm, ORC Manufacturing Co.,
Ltd. " HMW-680GW " made)
Alkali development：The Na of 1 mass %2CO3Aqueous solution, fluid temperature be 30 DEG C, injection pressure be 0.2MPa, developing time 60
Second
After cure：150 DEG C, 60 minutes
Assessment item is as follows.
(1) thixotropic ratio
60 seconds~65 seconds (25 DEG C) (being measured using rock field (Iwata) cup) is diluted to using solvent (propylene glycol monomethyl ether), so
Afterwards, it is respectively 5rpm to mandrel (spindle) rotating speed using the rich RVT type viscosimeters for strangling and flying (Brookfield) company and manufacturing
And temperature be 25 DEG C when photosensitive polymer combination BF viscosity (η 5) and mandrel rotating speed is 50rpm and temperature is 25 DEG C
When the BF viscosity (η 50) of photosensitive polymer combination be determined.Moreover, according to these measured values and to thixotropic ratio (η 5/
η 50) it is calculated.
(2) turned-down edge
In above-mentioned test film production process, for having carried out the substrate after predrying in an upright manner, according to
The film of lower benchmark visual valuation photosensitive polymer combination.
◎：The turned-down edge of film is not found in the thread pattern portion that conductor thickness is 90 μm
○：Although in the thread pattern portion that conductor thickness is 90 μm, there are the turned-down edges of film, are 60 μm thin in conductor thickness
Line pattern portion does not find the turned-down edge of film
△：Although in the thread pattern portion that conductor thickness is 60 μm, there are the turned-down edges of film, are 35 μm thin in conductor thickness
Line pattern portion does not find the turned-down edge of film
×：The thread pattern portion that conductor thickness is 35 μm there are film turned-down edge (in the thread pattern that conductor thickness is 18 μm
Portion does not find the turned-down edge of film)
(3) sensitivity
In above-mentioned test film production process, on the film of the substrate after the predrying for having carried out 80 DEG C, 20 minutes, setting
Sensitivity determination by stage exposure meter, uses accumulative quantometer (" UV- with stage exposure meter (Kodak, 21 sections)
351 ", ORC MANUFACTURING CO., LTD. are manufactured) the ultraviolet irradiation light quantity that dominant wavelength is 365nm is measured, and will
With 300mJ/cm2Substrate after being irradiated uses the Na of 1 mass % as test film2CO3Aqueous solution, the injection with 0.2MPa
Pressure develop within 60 seconds, then, for the part that exposed portion is not removed, is recorded, and press using number (number of stages)
It is evaluated according to following standard.
○：8 more than the stage
×：Below 7 stages
(4) sprayability
Observe the appearance of the film coated surface in above-mentioned test film production process after predrying by visual observation, and according to following standard into
Evaluation is gone.
◎：Bubble, orange peel line are not found, levelability is good
○：There are the coating near a small amount of orange peel line or Cu foils is thin
△：Other than there are a small amount of orange peel line, film coated surface slightly tarnishes
×：There are orange peel line or can not spray
Above-mentioned evaluation result is shown in table 2 below.
【Table 2】
As shown in above-mentioned table 2, in Examples 1 to 7, in the photoresist containing carboxyl, ((A) ingredient contains carboxylic
The photoresist of base) in corresponding synthetic resin (A-1), coordinate the quaternary ammonium salt pair represented using and by above-mentioned logical formula (I)
The VARISOFT TA100 answered treated bentonite, i.e. (E) ingredient using quaternary ammonium salt treated bentonite, with
And relative to (A) ingredient 100 mass parts of photoresist containing carboxyl be the mass parts of about 5.0 mass parts~about 18 (F)
Hydrophobic silica, the photoresist containing carboxyl have free-radical polymerised unsaturated group and epoxy group
Glycidyl compound is reacted with the carboxyl of the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid and is obtained
The reaction product arrived, in these embodiments, will be photosensitive even with spray coating method for the conductive pattern that thickness is 35 μm or more
Property resin combination applies thicker and so that wet-film thickness reaches 100 μm~110 μm, it may have excellent sensitivity and can
Turned-down edge is prevented, in addition, the cured coating film of excellent appearance can be formed in spraying.
In addition, it is combined with about 6.0 mass in 100 mass parts of photoresist containing carboxyl relative to (A) ingredient
Part~(E) ingredients of the mass parts of about 13 (F) hydrophobic silica of mass parts, about 9.0 mass parts~about 18 utilizes quaternary ammonium
In bentonitic embodiment 2~4 after salt treatment, even with spray coating method by wet-film thickness coating for 100 μm~110 μm compared with
Thick photosensitive polymer combination, will not be damaged excellent sensitivity, even if for the conductive pattern that thickness is 60 μm,
Turned-down edge can be prevented, and the appearance of cured coating film can also further improve.
On the other hand, as shown in Table 2 above, in 100 mass parts of photoresist containing carboxyl relative to (A) ingredient
And be combined in the comparative example 1 of (F) hydrophobic silica of about 4.0 mass parts, although wet-film thickness is 100 μm~110 μm
When, sensitivity is also good, but then produces turned-down edge for the conductive pattern that thickness is 35 μm.In addition, relative to (A) ingredient
100 mass parts of photoresist containing carboxyl and be combined with the comparative example 4 of (F) hydrophobic silica of about 27 mass parts
In, although wet-film thickness is 100 μm~110 μm, sensitivity is also good, and good appearance is not obtained in spraying.Separately
Outside, be combined with not make to have free-radical polymerised unsaturated group and the glycidyl of epoxy group and modified by polyacid from
The comparison of the photoresist containing carboxyl as obtained from the carboxyl reaction of base polymerism unsaturated monocarboxylic epoxy resin
In example 2,7, good sensitivity is not obtained.
In addition, it is combined in the comparative example 3 of hydrophilic silicon oxides in substitution (F) hydrophobic silica, for thickness
The conductive pattern spent for 35 μm produces turned-down edge.In addition, in unmated (E) ingredient, using quaternary ammonium salt, that treated is bentonitic
Comparative example 5 and above-mentioned (E) ingredient of substitution have been coordinated using quaternary ammonium salt treated bentonite and have been utilized stearyl benzyl two
In ammonio methacrylate treated bentonitic comparative example 6, turned-down edge is produced for the conductive pattern that thickness is 35 μm, and then,
Good appearance is still obtained in spraying.
Industrial availability
In the present invention, the photosensitive polymer combination for being applied even with spray coating method thicker, it may have excellent
Sensitivity, turned-down edge can be prevented, and the cured coating film of excellent appearance can be formed, thus, for example with thicker conductor
The printed circuit board of pattern (such as thickness be 35 μm or more) is set in the fields of insulating protective films such as solder mask, utility value compared with
It is high.
Claims (10)
1. a kind of photosensitive polymer combination, contains：
(A) photoresist containing carboxyl is the glycidol with free-radical polymerised unsaturated group and epoxy group
Based compound reacts obtained from being reacted with the carboxyl of the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid
Product, the free-radical polymerised unsaturated monocarboxylic epoxy resin of modified by polyacid is polyacid or its acid anhydrides and free radical
Compound obtained from the hydroxyl reaction of polymerism unsaturated monocarboxylic epoxy resin, it is described free-radical polymerised unsaturated single
Carboxylation epoxy resin is the multi-functional epoxy resin in 1 molecule with 2 or more epoxy groups and free-radical polymerised insatiable hunger
With the reaction product of monocarboxylic acid；
(B) Photoepolymerizationinitiater initiater；
(C) reactive diluent；
(D) epoxide；
(E) using the quaternary ammonium salt represented by the following general formula (I) treated bentonite,
[R1R2R3R4-N]+X- (I)
In formula, R1、R2、R3、R4It each independently represents saturated aliphatic hydrocarbons that carbon number is 1~25 or carbon number is not 2~25 not
Saturated aliphatic hydrocarbons, X represent the halogen in fluorine, chlorine, bromine and iodine；And
(F) hydrophobic silica,
Relative to the photoresist containing carboxyl of (A) ingredient described in 100 mass parts, containing 4.5 mass parts~20 mass parts
(F) hydrophobic silica.
2. photosensitive polymer combination according to claim 1, wherein, relative to containing for (A) ingredient described in 100 mass parts
Have the photoresist of carboxyl, containing 5.0 mass parts~20 (E) ingredient described in mass parts using quaternary ammonium salt, that treated is swollen
Profit soil.
3. photosensitive polymer combination according to claim 1 or 2, wherein, relative to (A) ingredient described in 100 mass parts
The photoresist containing carboxyl, containing 5.5 mass parts~13.5 (F) hydrophobic silicas described in mass parts, also,
Relative to the photoresist containing carboxyl of (A) ingredient described in 100 mass parts, containing 8.0 mass parts~18 mass parts institute
That states (E) ingredient utilizes quaternary ammonium salt treated bentonite.
4. photosensitive polymer combination according to claim 1 or 2, wherein, (E) ingredient utilizes quaternary ammonium salt treatment
Bentonitic quality afterwards：The quality of (F) hydrophobic silica is 1.0：0.30~3.0 range.
5. photosensitive polymer combination according to claim 3, wherein, after the utilization quaternary ammonium salt treatment of (E) ingredient
Bentonitic quality：The quality of (F) hydrophobic silica is 1.0：0.30~3.0 range.
6. according to the photosensitive polymer combination described in claim 1,2 or 5, wherein, (F) hydrophobic silica is profit
Silica after being modified with aIkylsilyl groups.
7. photosensitive polymer combination according to claim 3, wherein, (F) hydrophobic silica is utilizes alkane
Silica after the modification of base silicyl.
8. according to the photosensitive polymer combination described in claim 1,2,5 or 7, wherein, the quaternary ammonium salt is distearyl two
Methyl ammonium salt.
9. a kind of photocured product is the photocured product of photosensitive polymer combination described in any item of the claim 1 to 8.
10. a kind of circuit board, the photocuring film with photosensitive polymer combination described in any item of the claim 1 to 8.
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| JP6542435B2 (en) * | 2017-07-14 | 2019-07-10 | 株式会社タムラ製作所 | Photosensitive resin composition |
| CN111635723B (en) * | 2020-06-08 | 2022-03-22 | 武汉市三选科技有限公司 | Single-component dam material composition and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08134155A (en) * | 1994-11-14 | 1996-05-28 | Hitachi Chem Co Ltd | Thixotropic resin composition |
| CN104076603A (en) * | 2013-03-26 | 2014-10-01 | 株式会社田村制作所 | Photosensitive resin composition |
| CN105008471A (en) * | 2013-03-08 | 2015-10-28 | 中国涂料株式会社 | Anti-corrosion paint composition, anti-corrosion coating, and method for preventing corrosion of base material |
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| JP6524572B2 (en) * | 2013-07-01 | 2019-06-05 | 互応化学工業株式会社 | Composition for solder resist and printed wiring board |
| JP6204734B2 (en) * | 2013-07-16 | 2017-09-27 | 互応化学工業株式会社 | Resin composition for solder resist |
| JP5941180B1 (en) * | 2015-03-20 | 2016-06-29 | 太陽インキ製造株式会社 | Curable resin composition, dry film, cured product and printed wiring board |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08134155A (en) * | 1994-11-14 | 1996-05-28 | Hitachi Chem Co Ltd | Thixotropic resin composition |
| CN105008471A (en) * | 2013-03-08 | 2015-10-28 | 中国涂料株式会社 | Anti-corrosion paint composition, anti-corrosion coating, and method for preventing corrosion of base material |
| CN104076603A (en) * | 2013-03-26 | 2014-10-01 | 株式会社田村制作所 | Photosensitive resin composition |
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| CN112526823A (en) * | 2019-09-19 | 2021-03-19 | 株式会社田村制作所 | Photosensitive resin composition |
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