CN106750338A - A kind of photosensitive resin and preparation method thereof - Google Patents
A kind of photosensitive resin and preparation method thereof Download PDFInfo
- Publication number
- CN106750338A CN106750338A CN201611192158.9A CN201611192158A CN106750338A CN 106750338 A CN106750338 A CN 106750338A CN 201611192158 A CN201611192158 A CN 201611192158A CN 106750338 A CN106750338 A CN 106750338A
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- China
- Prior art keywords
- resin
- photosensitive resin
- reaction
- polyvinyl alcohol
- sbq
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
Abstract
The invention belongs to chemical field technical field, a kind of photosensitive resin and preparation method thereof is particularly related to.Wherein, the structure of the photosensitive resin that the present invention is provided includes at least two structural property of portfolio in polyvinyl alcohol, three kinds of structures of stibazole and resin.The photosensitive resin polymer has stronger photosensitive activity, stronger cohesiveness and hardness, pliability higher and good water dispersible, to meet macromolecular material especially demand of the aqueous UV photosensitive resins development of special material industry to Multifunction macromolecule resin material.
Description
Technical field
The invention belongs to chemical field technical field, a kind of photosensitive resin and preparation method thereof is particularly related to.
Background technology
With domestic polymeric material field especially special material field and its printing printing and dyeing, coating, electron chemistry
The application of the industries such as product, binder manufacture needs, and being badly in need of a class both has photosensitive activity higher, and attached with higher cohering
Ability and hardness and flexible while having water miscible macromolecule resin material again.Domestic and international market is so-called at present
Photo-curing monomer and photosensitive resin, itself no photolytic activity is, it is necessary to additionally add light trigger.
The content of the invention
In order to solve the above-mentioned shortcoming and defect mentioned in the prior art, the present invention provides a kind of photosensitive resin and its preparation
Method.Official of the present invention in the grafting principle of Polymer Materials ' Structure Functional Design and the structure of above-mentioned three classes compound
Feature can be rolled into a ball, using resin as basal body structure, three grafting of building block can be realized using chemical method.Specifically,
The present invention be grafted with the resin containing active group by by the polyvinyl alcohol with oh group, afterwards again with light
The SbQ containing aldehyde radical of quick activity carries out acetalation to prepare polyvinyl alcohol-SbQ- resinous polymers, obtains having concurrently above-mentioned
The multifunctional macromolecule special material of material advantages, with stronger photosensitive activity, stronger cohesiveness and hardness, higher soft
Toughness and good water dispersible.The resin is under ultraviolet (UV) light irradiation, you can crosslink curing reaction, is applied to light and consolidates
Change materials industry.
A kind of photosensitive resin that the present invention is provided is adopted the following technical scheme that：
A kind of photosensitive resin, its structure includes at least two in polyvinyl alcohol, three kinds of structures of stibazole and resin
Plant structural property of portfolio.
Further, structural property of portfolio includes block structure or repeats the architectural feature of block structure.
Further, including following weight raw material be obtained：
Resin 100-300 parts；
Polyvinyl alcohol 10-100 parts；
SbQ 1-20 parts.
Further, including following weight raw material be obtained：
200 parts of resin；
50 parts of polyvinyl alcohol；
5 parts of SbQ.
Further, the structure of resin at least includes the epoxy resin containing reaction active groups, phenolic resin, polyester tree
One or more of fat, acrylic resin, alkyd resin, amino resins, polyurethane resin, silane resin or acrylamide resin.
Further, its structural formula is：
Wherein resin part include the structure of various types of resins.
Further, when the resin is epoxy resin, its structural formula is：
The present invention also provides a kind of preparation method of above-mentioned photosensitive resin, including graft reaction and acetalation, its
In：
Graft reaction includes matching resin and polyvinyl alcohol according to certain part by weight and mixes in melting or the aqueous solution
It is even, catalyst is added, 5 DEG C~200 DEG C of controlling reaction temperature monitors reaction process, treats that the desired value of resin is reduced to a fixed number
After value, stop reaction, obtain using resin as basal body structure and polyvinyl alcohol graft copolymerized intermediate product；
Acetalation is included in after the intermediate product water dissolves obtained in graft reaction or is directly added into a certain amount of
SbQ, 5 DEG C~100 DEG C of controlling reaction temperature, stirring reaction monitors reaction process, after SbQ is converted completely, is neutralized with aqueous alkali
To faintly acid or neutrality, terminate reaction and obtain water photosensitive resin emulsion.
The present invention also provides the preparation method of another above-mentioned photosensitive resin, including：By resin, polyvinyl alcohol and
SbQ is well mixed in aqueous, adds catalyst, and 5 DEG C~100 DEG C of controlling reaction temperature after stirring reaction terminates, uses buck
Solution is neutralized to faintly acid, and cooling is to obtain water photosensitive resin emulsion.
Further, solvent is added in water photosensitive resin emulsion, that is, has Precipitation, filtered, drying to obtain solid
Photosensitive resin.
Further, the catalyst for being used in the said process acid such as Bronsted acid and solid acid such as including sulfuric acid, hydrochloric acid, phosphoric acid
Property compound.
Further, the range of reaction temperature in said process is 5~100 DEG C, and preferable reaction temperature scope is 40~80
℃。
Further, the mode of course of reaction is monitored in said process and (refers in particular to epoxy resin work herein for epoxide number is determined
Be matrix resin, other resinoids use corresponding index instead), viscosity measurement, electrophoresis method, spectrum and chromatographic process.
Further, the precipitation solvent for being used in said process is including various aliphatic hydrocarbons, ketone, ethers, esters, alcohols etc.
One or more mixed solvent, preferably use aliphatic hydrocarbon and acetone.
In current existing macromolecular material can part the high molecular polymer for meeting above-mentioned requirements have various types of resins,
Polyvinyl alcohol and styryl pyridine compound.In various types of resins, epoxy resin (Epoxy resin) is contained in molecule
The macromolecular compound of two or more epoxide groups, its molecular structure is to contain active epoxide group in strand
Be characterized, make its can with polytype curing agent crosslink reaction and formed it is insoluble, do not melt with tridimensional network
High polymer.Epoxy resin after solidification has good physics, chemical property, its surface tool to metal and nonmetallic materials
There is excellent bonding action, dielectric properties are good, and product size good stability, hardness is high, and pliability is preferable, to alkali and major part
Solvent-stable, thus be widely used in national defence, each department of national economy, is used as to pour into a mould, impregnates, lamination material, bonding agent, coating etc.
On the way.The active group having in various types of resins can carry out the modified suitable reaction site of offer of structural modification for it, be a class
Very promising new material develops matrix, and conventional resin includes above-mentioned epoxy resin, phenolic resin, polyester resin, acrylic acid
Resin, alkyd resin, amino resins, polyurethane resin, silane resin, acrylamide tree etc..Polyvinyl alcohol (PVA) is a class
Important Organic Chemicals, is also a kind of polyhydroxylated polymer being widely used, due to having great amount of hydroxy group in its molecule
Functional group, makes it have good hydrophily.Mainly for the manufacture of Pioloform, polyvinyl acetal, emulsifying agent, binder, fabric treating
The fields such as agent, paper coating and medical material.Styryl pyridine compound has good photosensitive activity, can be in illumination
The intermolecular polymerisation of life is issued, the manufacture of the photosensitive materials such as photoresists is commercially used for.Stibazole Methylsulfate
(SbQ) be organic stibazole salt resin photoresists emulsion, with ISO.In print field, than what is commonly used
Wire mark sensitivity of photographic material is high 3~4 times, and the consumption of SbQ emulsion is considerably less, and only 1~5%mol of hydroxyl can just have
Satisfied speed, it is not necessary to add sensitizing initiator, widely should obtain in terms of printing industry and photoresist
With.
The present invention according to the block principle design of Molecular Design it is new with water dispersible, cohesive force high, soft
Toughness and adhesive force and with the resin material of very strong photosensitive activity.With chemical constitution block fashion, by chemical reaction, contracting
Aldehyde reaction has obtained block polymer product.Develop the preparation technology for synthesizing such compound, and purifying and analysis prison
Prosecutor method.Product resin has reached the purpose of design of material through performance evaluation, with light sensitivity, water solubility, through ultraviolet light (UV)
Irradiation possesses the characteristics such as certain intensity, pliability and adhesive force after crosslinking solidification.
Product resin, can be not limited to waterborne UV coating, aqueous UV ink and aqueous UV binders etc..
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
The accompanying drawing to be used needed for having technology description is briefly described, it should be apparent that, drawings in the following description are the present invention
Some embodiments, for those of ordinary skill in the art, on the premise of not paying creative work, can also basis
These accompanying drawings obtain other accompanying drawings.
Fig. 1 is the resin-polyvinyl alcohol-SbQ polymer architecture ideographs of photosensitive resin provided in an embodiment of the present invention；
Fig. 2 is the structural representation of resin matrix (epoxy resin) and polyvinyl alcohol and stibazole；
Fig. 3 is the epoxy resin-polyvinyl alcohol-SbQ polymer architecture patterns of photosensitive resin provided in an embodiment of the present invention
Figure.
Specific embodiment
To make the purpose, technical scheme and advantage of the embodiment of the present invention clearer, below in conjunction with the embodiment of the present invention
In accompanying drawing, the technical scheme in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment is
A part of embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art
The every other embodiment obtained under the premise of creative work is not made, belongs to the scope of protection of the invention.
With reference to embodiment, the present invention is further described, and specific embodiment (is matched somebody with somebody by following weight portion as shown in table 1
The raw material of ratio is obtained)：
Table 1
Lower its preparation method is illustrated by taking embodiment 1 as an example below.The preparation method of embodiment 1 can be divided into two kinds, one kind
It is " step synthesis " that one kind is " one-step synthesis ".
(1) step synthesis：
Step synthesis include graft reaction and acetalation, wherein：
Graft reaction includes being added to 50g polyvinyl alcohol in 450g deionized waters, is made into homogeneous solution；Add 200 rings
Oxygen tree fat E44 stirs, and adds catalyst phosphoric acid 8g, is warming up to 40 DEG C~90 DEG C, and 10~20h of stirring reaction determines ring
Oxygen value (refering in particular to epoxy resin herein as matrix resin, other resinoids use corresponding index instead) monitors reaction process, treats ring
Oxygen value is reduced to close to after 0 (such as 0.01g/100g), stops reaction, obtains embedding with polyvinyl alcohol as basal body structure using resin
The intermediate product of section copolymer, the product is directly applied in the next step without separation；
Acetalation include upwards step reactant mixture in add SbQ 5g, be warming up to 40 DEG C~90 DEG C, stirring reaction
15h~40h, reaction process is monitored by viscosity measurement, IR, after SbQ is converted completely, terminates reaction, water-soluble with NaOH
Liquid is neutralized to pH value 4.5~6.5, obtains water photosensitive resin emulsion, can be used directly to prepare waterborne radiation curable coating, ink
Deng；Or to acetone 2000mL is added in reactant mixture, there is Precipitation, and filter, it is dried to obtain target product (the photosensitive tree of solid
Fat) 250g.
(2) one-step synthesis：
50g polyvinyl alcohol 1788 is added in 450g deionized waters, homogeneous solution is made into；Add 200g epoxy resin
E44 stirs, and adds catalyst phosphoric acid 8g, is warming up to 40~90 DEG C；Add 5g SbQ to stir, be warming up to reaction temperature
60~90 DEG C of degree, 20~40h of stirring reaction, is determined by epoxide number and viscosity measurement monitors course of reaction, treats epoxide number to connect
Near is 0, and when viscosity increases to specified numerical value, reaction terminates, cooling, and pH value 4.5~6.5 is neutralized to sodium hydrate aqueous solution,
Water photosensitive resin emulsion is obtained, can be used directly to prepare waterborne radiation curable coating, ink etc..Or added in reactant mixture
Acetone 2000mL, makes the product Precipitation of generation, filtering, dries, and obtains target product 250g.
Fig. 1 is the resin-polyvinyl alcohol-SbQ polymer architecture ideographs of photosensitive resin provided in an embodiment of the present invention, figure
Resin part represent the structure of various types of resins in 1, such as including the epoxy resin containing reaction active groups, phenolic resin,
In polyester resin, acrylic resin, alkyd resin, amino resins, polyurethane resin, silane resin or acrylamide resin one
Plant or various.
The principle of the above-mentioned preparation technology foundation of the present invention is：Due to having reactive functional group in resin matrix configuration
(the epoxy construction functional group such as in epoxy resin), the functional group can be with the hydroxy functional group of polyvinyl alcohol with/without catalysis
Under conditions of agent, reacted uniform condition is sufficiently mixed, so as to resin matrix is grafted in polyvinyl alcohol structures.By
In the introducing of polyvinyl alcohol structures, make to increased substantial amounts of hydroxy functional group in molecular structure, the design feature can be in acidity
Under the conditions of with SbQ structures in aldehyde radical occur acetalation, SbQ structures are grafted on molecular structure.
By taking epoxy resin as an example, by the analysis (as shown in Figure 2) of the chemical constitution of above-mentioned three kinds of materials, epoxy resin structural two
Functional group's epoxy radicals at end can occur condensation etherification reaction with polyvinyl alcohol, and the aldehyde radical in SbQ structures can be with polyvinyl alcohol
Hydroxyl in block carries out splicing of the acetalation so as to realize above three fragment and obtains epoxy resin-polyvinyl alcohol-SbQ
Polymer (as shown in Figure 3).It should be noted that this structural formula is by taking epoxy resin as an example, other resins are similar, i.e.,
" epoxy resin part " can be other resins.
The invention has the characteristics that：
The present invention according to the block principle design of Molecular Design one class it is new with water dispersible, bonding high
Power, pliability and adhesive force and with the resin material of very strong photosensitive activity.With chemical constitution block fashion, by chemical anti-
Answer, acetalation has obtained block polymer product.The preparation technology for synthesizing such compound is developed, and is purified and is divided
Analysis monitoring method.Product resin has reached the purpose of design of material through performance evaluation, with light sensitivity, water solubility, through ultraviolet light
(UV) irradiation possesses the characteristics such as certain intensity, pliability and adhesive force after crosslinking solidification.It is that a kind of self-initiating is photosensitive
(UV) resin, i.e., need not additionally add light trigger, under uv illumination can crosslink solidification, can extensively using direction in
Aqueous (instead of oiliness, no-solvent type) UV coating, UV ink, UV binders etc..
Finally it should be noted that various embodiments above is merely illustrative of the technical solution of the present invention, rather than its limitations；To the greatest extent
Pipe has been described in detail with reference to foregoing embodiments to the present invention, it will be understood by those within the art that：Its according to
The technical scheme described in foregoing embodiments can so be modified, or which part or all technical characteristic are entered
Row equivalent；And these modifications or replacement, the essence of appropriate technical solution is departed from various embodiments of the present invention technology
The scope of scheme.
Claims (10)
1. a kind of photosensitive resin, it is characterised in that its structure is included in polyvinyl alcohol, three kinds of structures of stibazole and resin
At least two structural property of portfolio.
2. photosensitive resin according to claim 1, it is characterised in that structural property of portfolio includes block structure or repeats embedding
The architectural feature of segment structure.
3. photosensitive resin according to claim 1, it is characterised in that the raw material including following weight is obtained：
Resin 100-300 parts；
Polyvinyl alcohol 10-100 parts；
SbQ 1-20 parts.
4. photosensitive resin according to claim 3, it is characterised in that the raw material including following weight is obtained：
200 parts of resin；
50 parts of polyvinyl alcohol；
5 parts of SbQ.
5. photosensitive resin according to claim 1, it is characterised in that the structure of resin at least includes containing reactivity base
Epoxy resin, phenolic resin, polyester resin, acrylic resin, alkyd resin, amino resins, polyurethane resin, the silane tree of group
One or more in fat or acrylamide resin.
6. photosensitive resin according to claim 1, it is characterised in that its structural formula is：
Wherein resin part include the structure of various types of resins.
7. photosensitive resin according to claim 1, it is characterised in that when the resin is epoxy resin, its structural formula is：
8. the preparation method of the photosensitive resin described in a kind of any one of claim 1~7, it is characterised in that including graft reaction
And acetalation, wherein：
Graft reaction includes according to certain part by weight proportioning being well mixed resin and polyvinyl alcohol in melting or the aqueous solution, plus
Enter catalyst, 5 DEG C~200 DEG C of controlling reaction temperature monitors reaction process, after the desired value of resin is reduced to certain numerical value,
Stop reaction, obtain using resin as basal body structure and polyvinyl alcohol graft copolymerized intermediate product；
Acetalation is included in after the intermediate product water dissolves obtained in graft reaction or is directly added into a certain amount of SbQ,
5 DEG C~100 DEG C of controlling reaction temperature, stirring reaction monitors reaction process, after SbQ reacts completely, is neutralized with aqueous alkali and arrives weak
Acidity, terminates reaction and obtains water photosensitive resin emulsion.
9. the preparation method of the photosensitive resin described in a kind of any one of claim 1~7, it is characterised in that including：By resin,
Polyvinyl alcohol and SbQ are well mixed in aqueous according to certain part by weight proportioning, add catalyst, 5 DEG C of controlling reaction temperature
~100 DEG C, stirring reaction after SbQ reacts completely, is neutralized to faintly acid with aqueous alkali, and cooling is to obtain water photosensitive resin
Emulsion.
10. the preparation method of photosensitive resin according to claim 8 or claim 9, it is characterised in that in water photosensitive resin emulsion
Solvent is added, that is, has Precipitation, filtered, drying to obtain solid photosensitive resin.
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| CN201611192158.9A CN106750338A (en) | 2016-12-21 | 2016-12-21 | A kind of photosensitive resin and preparation method thereof |
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| CN201611192158.9A CN106750338A (en) | 2016-12-21 | 2016-12-21 | A kind of photosensitive resin and preparation method thereof |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04358151A (en) * | 1991-06-04 | 1992-12-11 | Sanyo Kokusaku Pulp Co Ltd | Image forming method |
| KR20000025644A (en) * | 1998-10-13 | 2000-05-06 | 구자홍 | Method for forming fluorescent film of color cathode ray tube |
| CN1766102A (en) * | 2005-08-31 | 2006-05-03 | 农业部环境保护科研监测所 | PVA-SbQ synthesis and acetylcholinesterase fixing by same |
| CN101018819A (en) * | 2004-09-13 | 2007-08-15 | 旭化成化学株式会社 | Process for producing cured product of photosensitive resin |
| CN101592864A (en) * | 2008-05-30 | 2009-12-02 | 上海中大科技发展有限公司 | Single-component water-emulsion type rotary screen stenciling sensitive material |
| CN103279010A (en) * | 2013-06-20 | 2013-09-04 | 浙江荣生科技有限公司 | Method for preparing dual-curing single-component silk-screen printing photosensitive adhesive |
| CN103645604A (en) * | 2013-11-28 | 2014-03-19 | 浙江荣生科技有限公司 | Preparation method of chromium-free rotary screen photosensitive adhesive |
| CN106146753A (en) * | 2015-04-01 | 2016-11-23 | 合肥杰事杰新材料股份有限公司 | A kind of modified light-sensitive resin for Stereolithography and preparation method thereof |
-
2016
- 2016-12-21 CN CN201611192158.9A patent/CN106750338A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04358151A (en) * | 1991-06-04 | 1992-12-11 | Sanyo Kokusaku Pulp Co Ltd | Image forming method |
| KR20000025644A (en) * | 1998-10-13 | 2000-05-06 | 구자홍 | Method for forming fluorescent film of color cathode ray tube |
| CN101018819A (en) * | 2004-09-13 | 2007-08-15 | 旭化成化学株式会社 | Process for producing cured product of photosensitive resin |
| CN1766102A (en) * | 2005-08-31 | 2006-05-03 | 农业部环境保护科研监测所 | PVA-SbQ synthesis and acetylcholinesterase fixing by same |
| CN101592864A (en) * | 2008-05-30 | 2009-12-02 | 上海中大科技发展有限公司 | Single-component water-emulsion type rotary screen stenciling sensitive material |
| CN103279010A (en) * | 2013-06-20 | 2013-09-04 | 浙江荣生科技有限公司 | Method for preparing dual-curing single-component silk-screen printing photosensitive adhesive |
| CN103645604A (en) * | 2013-11-28 | 2014-03-19 | 浙江荣生科技有限公司 | Preparation method of chromium-free rotary screen photosensitive adhesive |
| CN106146753A (en) * | 2015-04-01 | 2016-11-23 | 合肥杰事杰新材料股份有限公司 | A kind of modified light-sensitive resin for Stereolithography and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 郑武城，等: "《光学化工辅料》", 30 April 1985, 测绘出版社 * |
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Application publication date: 20170531 |