CN110007559A - A kind of photosensitive polymer combination and preparation method thereof with high storage stability - Google Patents
A kind of photosensitive polymer combination and preparation method thereof with high storage stability Download PDFInfo
- Publication number
- CN110007559A CN110007559A CN201910301741.6A CN201910301741A CN110007559A CN 110007559 A CN110007559 A CN 110007559A CN 201910301741 A CN201910301741 A CN 201910301741A CN 110007559 A CN110007559 A CN 110007559A
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- CN
- China
- Prior art keywords
- photosensitive polymer
- polymer combination
- storage stability
- diazonium
- high storage
- 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.)
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Classifications
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- 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
-
- 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
- G03F7/016—Diazonium salts or compounds
- G03F7/021—Macromolecular diazonium compounds; Macromolecular additives, e.g. binders
-
- 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
Abstract
The invention discloses a kind of photosensitive polymer combination and preparation method thereof with high storage stability, including a kind of photosensitive polymer combination with high storage stability, using phosphoric acid as reaction medium, it enables substituted 4- diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde is condensed to yield phosphate diazo resin liquid, and the molar ratio of substituted 4- diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde is 1:1.15-1:3.5, in specific preparation process, synthetic phosphate diazo resin liquid and the photoresist liquid prepared are subjected to impregnation according to a certain percentage and finally obtain photosensitive polymer combination, the photosensitive polymer combination of phosphate diazo liquid resin provided by the invention has There is preservation to stablize excellent, the characteristics of light-sensitive surface of exposure performance and formation is had excellent performance, and prepare simple, it can be improved industrial production efficiency.
Description
Technical field
The present invention relates to silk-screen printing photosensitive polymer combinations, in particular to a kind of phosphate diazo resin
Liquid and photosensitive polymer combination comprising it, more particularly to water development can be used, there is longer stability after the mixing of two liquid
Photosensitive polymer combination.
Background technique
In order to form required pattern on carrier, the mode of printings such as intaglio plate, relief printing plate, silk-screen printing have his own strong points.
The industries such as circuit board, stamp mainly use the mode of silk-screen printing to realize the transfer of pattern now, and print in screen printing process
The production of brush halftone, which just lacks, can't do without photosensitive polymer combination, photosensitive polymer combination is coated on substrate (polyester webs,
Stainless (steel) wire, polyester piece etc.), using have the substrate after figuratum exposure mask and coating in high-pressure mercury-vapor lamp or metal halid lamp or
It is exposed under LED light, is exposed to unexposed portion using photosensitive polymer combination and the dissolution sex differernce of developer solution is carried out
Development is to obtain required image.
As silk-screen printing industry printing product further increases the requirements such as halftone precision, patience, photonasty tree
Oil/fat composition caters to the market demand also towards high sensitivity, high-precision, high patience, the development of high storage stability.
However conventional diazo resin be it is powdered, when use dissolved using pure water after photosensitive polymer combination is added
In be just coated with plate-making exposure after apply, deposit upon mixing that the pot-life is not for the photosensitive polymer combination of diazonium system
It is long, it is sometimes desirable to refrigeration just can guarantee performance, and it is also harsher to be coated with unexposed halftone preservation, be often easy to appear due to
Save it is bad and caused by quality problems, conventional diazo resin using the mixed acid that sulfuric acid or sulfuric acid and phosphoric acid form as be situated between
Matter, reactant temperature is added at 10 DEG C hereinafter, condition is harsher and the processing of conventional powders diazo resin post-synthesis phase in make
It is embathed with a large amount of methanol, ethyl alcohol or isopropanol, generates more solvent slop, later period three-protection design higher cost.
Summary of the invention
Goal of the invention: in order to solve deficiency present in above-mentioned technology, the present invention provides a kind of with high storage stability
Photosensitive polymer combination and preparation method thereof, it includes phosphate diazo liquid resin photosensitive polymer combination
Preservation is stablized excellent, and exposure performance and the light-sensitive surface of formation are had excellent performance, and it is wide to provide a kind of synthesis temperature requirement
Pine reduces the synthesis process of the phosphate diazo liquid of later period solvent treatment process.
Technical solution: a kind of photosensitive polymer combination with high storage stability, including phosphate diazo resin liquid
2-10%, polyvinyl alcohol based polymer 1-25%, resin aqueous emulsion 1-80%, light-cured resin 2-35%, photopolymerization cause
Agent 0.1-4%, water 5-55%, additive 0.1-10% enable substituted 4- diazonium diphenylamines using phosphoric acid as reaction medium
Sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde are condensed to yield phosphate diazo resin liquid, and by
The molar ratio of substituted 4- diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde is
1:1.15-1:3.5。
As a kind of preferred embodiment of the invention, the phosphate diazo resin liquid contains admittedly for 15-50%.
As a kind of preferred embodiment of the invention, the polyvinyl alcohol based polymer be polyvinyl alcohol, anion or sun from
The modified polyvinylalcohol of son, epoxy modifying polyethylene alcohols, the photosensitive base containing SBQ polyvinyl alcohol it is one or more above
The alcoholysis degree of polyvinyl alcohol mixture, the polyvinyl alcohol or modified polyvinylalcohol is 85-99mol%, polymer 300-
3500。
As a kind of preferred embodiment of the invention, the resin aqueous emulsion is film forming water-insoluble materials.
As a kind of preferred embodiment of the invention, the light-cured resin is at least containing more than one vinyl unsaturated group
The oil-soluble of group and/or the mixture of water soluble compound.
As a kind of preferred embodiment of the invention, the Photoepolymerizationinitiater initiater is the oil-soluble and/or water of free radical polymerization
Soluble initiator.
As a kind of preferred embodiment of the invention, the additive includes defoaming agent, levelling agent, mill base, preservative and can
Mould agent.
A kind of preparation method of the photosensitive polymer combination with high storage stability, comprising the following steps:
(a) it the synthesis of phosphate diazo resin liquid: after the phosphoric acid of metering is added, is warming up to and is added and can be taken at 20-60 DEG C
The 4- diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate in generation stir 1-5h；Paraformaldehyde is slow
It is added portionwise, 8-20h is stirred to react at 20-60 DEG C into the slightly saturating viscous fluid of sepia；It will be used after completely reacted viscous fluid cooling
Pure water is diluted to required solid content；
(b) prepared by photoresist liquid: by the 90% of polyvinyl alcohol based polymer formula water in 70-90 DEG C of condition height
Fast stirring and dissolving is abundant, and water-base resin liquid, light-cured resin, Photoepolymerizationinitiater initiater, the 10% of formula water, additive point is added
Filtering after dissipating uniformly；
(c) impregnation: a certain proportion of photoresist liquid and phosphate diazo resin liquid, which are uniformly mixed, can be obtained sense
Photosensitive resin composition.
The present invention realize it is following the utility model has the advantages that
For the present invention during synthesizing phosphate liquid diazo resin, temperature control is loose, without rear solvent treatment process, reduces
The photosensitive polymer combination containing phosphate diazo liquid resin of energy consumption and solvent slop treatment process, preparation also has
Longer storage stability, in addition, loose using the halftone conditions of exposure of photosensitive polymer combination of the present invention preparation, halftone is comprehensive
Close better performances.
Specific embodiment
The following is a clear and complete description of the technical scheme in the embodiments of the invention, it is clear that described embodiment
Only a part of the embodiment of the present invention, instead of all the embodiments.
A kind of photosensitive polymer combination with high storage stability, including phosphate diazo resin liquid 2-10% gather
Vinyl alcohol polymer 1-25%, resin aqueous emulsion 1-80%, light-cured resin 2-35%, Photoepolymerizationinitiater initiater 0.1-4%,
Water 5-55%, additive 0.1-10%, using phosphoric acid as reaction medium, enable substituted 4- diazonium diphenylamines sulfate and/
Or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde are condensed to yield phosphate diazo resin liquid, and substituted 4-
The molar ratio of diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde is 1:1.15-1:
3.5。
As a kind of preferred embodiment of the invention, phosphate diazo resin liquid contains admittedly for 15-50%.
As a kind of preferred embodiment of the invention, polyvinyl alcohol based polymer is polyvinyl alcohol, anion or cation
Modified polyvinylalcohol, epoxy modifying polyethylene alcohols, the photosensitive base containing SBQ polyvinyl alcohol one or more above poly- second
The alcoholysis degree of alkene alcohol-based mixtures, polyvinyl alcohol or modified polyvinylalcohol is 85-99mol%, polymer 300-3500.
As a kind of preferred embodiment of the invention, resin aqueous emulsion is film forming water-insoluble matter.
As a kind of preferred embodiment of the invention, light-cured resin is at least containing more than one vinyl unsaturated group
The mixture of oil-soluble and/or water soluble compound.
As a kind of preferred embodiment of the invention, Photoepolymerizationinitiater initiater is the oil-soluble and/or water solubility of free radical polymerization
Initiator.
As a kind of preferred embodiment of the invention, additive includes defoaming agent, levelling agent, mill base, preservative and plasticizer.
In specific preparation process, phosphate diazo liquid resins synthesis:
Embodiment 1
By in 85% phosphoric acid of the 4- diazonium diphenylamines disulfate 50g 44g for being dissolved in 40 DEG C of constant temperature in batches, at 50 DEG C
Under paraformaldehyde 6g, isothermal reaction 8h are added in batches；Addition 26g water dispersion is uniform after cooling obtains sepia phosphate liquid weight
Nitrogen resin liquid.
Embodiment 2
4- diazonium diphenylamines disulfate 50g is dissolved in batches in 85% phosphoric acid of 30 DEG C of 43g of constant temperature, at normal temperature
Paraformaldehyde 10g, normal-temperature reaction 14h are added in batches；Addition 157g water dispersion is uniform after cooling obtains sepia phosphate liquid
Diazo resin liquid.
Comparative example 1
4- diazonium diphenylamines disulfate 50g is dissolved in the nitration mixture of the sulfuric acid 75g of 65% phosphoric acid 75g and 80%,
In 10 DEG C or less addition paraformaldehyde 6g, 6h is reacted at normal temperature, obtained dispersion liquid is dispersed in 2L isopropanol and stands 12h
After filter, be cleaned multiple times with isopropanol 0.4L, be dried at 25 DEG C or less, obtain yellow green diazo resin powder 50.4g.
The preparation of photosensitive polymer combination:
Emulsion 1
It is dissolved completely in using polyvinyl alcohol (degree of polymerization 2000) 22.5g of the partial alcoholysis of alcoholysis degree 87-89mol%
In 127.5g pure water, polyvinyl alcohol water solution is obtained, homemade vinyl acetate-acrylic is added in polyvinyl alcohol water solution
Ester copolymer emulsion 750g (solid content 47%) and aqueous blue mill base 0.18g (raw 8301 mill bases of Shanghai coloured silk), uses blender
It is uniformly dispersed.
Emulsion 2
It is dissolved completely in using polyvinyl alcohol (degree of polymerization 2000) 97.5g of the partial alcoholysis of alcoholysis degree 87-89mol%
In 552.5g pure water, polyvinyl alcohol water solution is obtained.Homemade polyvinyl acetate emulsion is added in polyvinyl alcohol water solution
250g (solid content 48%) and aqueous blue mill base 0.18g (raw 8301 mill bases of Shanghai coloured silk), is uniformly dispersed using blender.
Emulsion 3
476g is dissolved completely in using polyvinyl alcohol (degree of polymerization 2000) 84g of the partial alcoholysis of alcoholysis degree 87-89mol%
In pure water, polyvinyl alcohol water solution is obtained.Be added in polyvinyl alcohol water solution homemade polyvinyl acetate emulsion 160g (Gu
Content 47%), pentaerythritol triacrylate 84.5g (East Asia DIC M-305), tripropylene glycol diacrylate 88.5g (east
Sub- DIC M-220) Photoepolymerizationinitiater initiater 7g (Changsha Sunyu ITX) and aqueous blue mill base 0.18g (raw 8301 colors of Shanghai coloured silk
Slurry), it is uniformly dispersed using blender.
Add 1 phosphate diazo resin liquid 7.5g of embodiment, embodiment 2 respectively in above-mentioned emulsion 1, emulsion 2, emulsion 3
The diazo resin powder 3g of phosphate diazo resin liquid 15g and comparative example 1, after mixing, with the polyester net (Japan of 250T
Day is special) filtering, prepare 9 kinds of photosensitive polymer combinations.
Plate-making experiment: by obtain 9 kinds of photosensitive polymer combinations, using scraper, on the yellow-coloured polyester silk screen of 250 mesh
It is coated and dried the photosensitive film that 15 μ m-thicks are made, is exposed and is made a plate with 3KW metal halid lamp.Obtain the plate-making result of table 1；
Herein it should be noted that in table: zero indicates image clearly；△ indicates that image is general；╳ indicates that image is unavailable.
Table 1
| Embodiment 1 | Embodiment 2 | Comparative example 1 | |
| Emulsion 1 | △ | ○ | △ |
| Emulsion 2 | ○ | ○ | ○ |
| Emulsion 3 | ○ | ○ | △ |
Storage stability test: the photosensitive resin composition that emulsion 2 and embodiment 1, embodiment 2 and comparative example 1 are made into
Object under 40 DEG C of baking ovens and normal temperature condition in be kept in dark place, periodic detection viscosity and observation state the results are shown in Table 2.
Table 2
The above embodiments merely illustrate the technical concept and features of the present invention, and the purpose is to allow the skill for being familiar with the technical field
Art personnel can understand the content of the present invention and implement it accordingly, and can not be limited the scope of the invention with this.All bases
Equivalent changes or modifications made by spirit of the invention, should be covered by the protection scope of the present invention.
Claims (8)
1. a kind of photosensitive polymer combination with high storage stability, including phosphate diazo resin liquid 2-10%, poly- second
Enol quasi polymer 1-25%, resin aqueous emulsion 1-80%, light-cured resin 2-35%, Photoepolymerizationinitiater initiater 0.1-4%, water
5-55%, additive 0.1-10%, which is characterized in that using phosphoric acid as reaction medium, enable substituted 4- diazonium diphenylamines
Sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde are condensed to yield phosphate diazo resin liquid, and by
The molar ratio of substituted 4- diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate and paraformaldehyde is
1:1.15-1:3.5。
2. a kind of photosensitive polymer combination with high storage stability according to claim 1, which is characterized in that institute
Phosphate diazo resin liquid is stated to contain admittedly for 15-50%.
3. a kind of photosensitive polymer combination with high storage stability according to claim 1, which is characterized in that institute
State polyvinyl alcohol based polymer be polyvinyl alcohol, the modified polyvinylalcohol of anion or cation, epoxy modifying polyethylene alcohols,
One or more above polyvinyl alcohol mixtures of the polyvinyl alcohol of the photosensitive base containing SBQ, the polyvinyl alcohol or modification
The alcoholysis degree of polyvinyl alcohol is 85-99mol%, polymer 300-3500.
4. a kind of photosensitive polymer combination with high storage stability according to claim 1, which is characterized in that institute
Resin aqueous emulsion is stated as film forming water-insoluble materials.
5. a kind of photosensitive polymer combination with high storage stability according to claim 1, which is characterized in that institute
State the mixing that light-cured resin is the oil-soluble and/or water soluble compound at least containing more than one vinyl unsaturated group
Object.
6. a kind of photosensitive polymer combination with high storage stability according to claim 1, which is characterized in that institute
State the oil-soluble and/or water soluble starter that Photoepolymerizationinitiater initiater is free radical polymerization.
7. a kind of photosensitive polymer combination with high storage stability according to claim 1, which is characterized in that institute
Stating additive includes defoaming agent, levelling agent, mill base, preservative and plasticizer.
8. a kind of preparation method of the photosensitive polymer combination with high storage stability, which is characterized in that the photonasty
Resin combination is photosensitive polymer combination described in claim 1, and preparation method includes the following steps:
(a) synthesis of phosphate diazo resin liquid: after the phosphoric acid of metering is added, being warming up to addition at 20-60 DEG C can be substituted
4- diazonium diphenylamines sulfate and/or 4- diazonium -3- methoxy diphenylamine sulfate stir 1-5h；Slowly in batches by paraformaldehyde
It is added, 8-20h is stirred to react at 20-60 DEG C into the slightly saturating viscous fluid of sepia；Pure water will be used after completely reacted viscous fluid cooling
It is diluted to required solid content；
(b) prepared by photoresist liquid: by the 90% of polyvinyl alcohol based polymer formula water in 70-90 DEG C of condition high-speed stirring
It mixes and dissolves sufficiently, water-base resin liquid, light-cured resin, Photoepolymerizationinitiater initiater, the 10% of formula water, additive dispersion is added
Filtering after even；
(c) impregnation: a certain proportion of photoresist liquid and phosphate diazo resin liquid, which are uniformly mixed, can be obtained photonasty
Resin combination.
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| CN201910301741.6A CN110007559A (en) | 2019-04-16 | 2019-04-16 | A kind of photosensitive polymer combination and preparation method thereof with high storage stability |
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| CN201910301741.6A CN110007559A (en) | 2019-04-16 | 2019-04-16 | A kind of photosensitive polymer combination and preparation method thereof with high storage stability |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279986A (en) * | 2020-10-29 | 2021-01-29 | 浙江荣生科技有限公司 | Preparation method of diazo photosensitizer |
| CN113406863A (en) * | 2021-06-16 | 2021-09-17 | 田菱智能科技(昆山)有限公司 | Photo-thermal dual-curing photosensitive glue, and preparation method and application method thereof |
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| JP2010055125A (en) * | 2003-08-25 | 2010-03-11 | Hitachi Chem Co Ltd | Photosensitive resin composition for permanent resist, photosensitive film for permanent resist, method for forming resist pattern, and printed wiring board |
| CN102311529A (en) * | 2010-07-07 | 2012-01-11 | 参太富有限公司 | Diazoresin, photosensitive resin composition and photosensitive film for screen plate |
| CN102523756A (en) * | 2010-09-03 | 2012-06-27 | 株式会社村上 | Photosensitive resin composition, and stencil for screen printing using said photosensitive resin composition |
| JP2012215862A (en) * | 2011-03-26 | 2012-11-08 | Suntype Co Ltd | Photosensitive resin composition, photosensitive film and screen plate for screen printing |
| US20150212413A1 (en) * | 2012-09-25 | 2015-07-30 | Suntype Co., Ltd. | Photosensitive resin composition for screen printing, photosensitive film, and screen plate |
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2019
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Patent Citations (6)
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| WO2005008338A1 (en) * | 2003-07-17 | 2005-01-27 | Hitachi Chemical Co., Ltd. | Negative photosensitive resin composition and negative photosensitive element |
| JP2010055125A (en) * | 2003-08-25 | 2010-03-11 | Hitachi Chem Co Ltd | Photosensitive resin composition for permanent resist, photosensitive film for permanent resist, method for forming resist pattern, and printed wiring board |
| CN102311529A (en) * | 2010-07-07 | 2012-01-11 | 参太富有限公司 | Diazoresin, photosensitive resin composition and photosensitive film for screen plate |
| CN102523756A (en) * | 2010-09-03 | 2012-06-27 | 株式会社村上 | Photosensitive resin composition, and stencil for screen printing using said photosensitive resin composition |
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| CN112279986A (en) * | 2020-10-29 | 2021-01-29 | 浙江荣生科技有限公司 | Preparation method of diazo photosensitizer |
| CN113406863A (en) * | 2021-06-16 | 2021-09-17 | 田菱智能科技(昆山)有限公司 | Photo-thermal dual-curing photosensitive glue, and preparation method and application method thereof |
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