CN106588860A - Dimethyl dioxane pentyl alkanol methacrylate monomer and application thereof - Google Patents
Dimethyl dioxane pentyl alkanol methacrylate monomer and application thereof Download PDFInfo
- Publication number
- CN106588860A CN106588860A CN201610968412.3A CN201610968412A CN106588860A CN 106588860 A CN106588860 A CN 106588860A CN 201610968412 A CN201610968412 A CN 201610968412A CN 106588860 A CN106588860 A CN 106588860A
- Authority
- CN
- China
- Prior art keywords
- methacrylate monomer
- monomer
- application
- dimethyl
- film
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
Abstract
The invention discloses a dimethyl dioxane pentyl alkanol methacrylate monomer with function of UV Curable and application thereof. The structural formula is (img file='DDA0001146219900000011.TIF' wi='660' he='486' /). The dimethyl dioxane pentyl alkanol methacrylate monomer is a good photo-curing agent, which is capable of modifying epoxy acrylic resin oligomer so that a solidified film can be formed.
Description
Technical field
The present invention relates to photocuring technology field, more particularly to dimethyl dioxin-pentane alcohol methacrylate light curing agent
Monomer and application.
Background technology
Photocuring system is made up of oligomer, reactive diluent, light trigger and various additives, is divided into free radical
Curing system and Cationic curing systems, at present main application is radical UV curing system.With ultraviolet in photocuring technology
Photocuring technology is with the fastest developing speed, and compared to heat cure etc., other curing systems have energy-conservation, film to UV curing system
The advantages of performance is good, production efficiency is high, expense is low, speed is fast and pollution is few.Ultra-violet curing membrane material is substantially free of in itself volatilization
Property solvent, curing rate is rapid, therefore the environment-friendly type that is otherwise known as (SE types) coating.UV-curing technology belongs to chemical method, it
It is, by ultraviolet light initiating chamical reaction, to make original liquid small molecule by specific functional group, such as ethylene linkage, epoxy bond etc. are sent out
Raw polyreaction and molding.In China, with the pay attention to day by day of the continuous expansion and people of economic scale to environmental conservation, make
Correlational study, development and application for the ultraviolet-curing paint of environment-friendly type " green " technique has also increasingly been goed deep into and has been popularized.
Light curing agent monomer, is also called photocuring reactive diluent or photocuring functional monomer, is that one kind contains polymerizable
The organic molecule of functional group.In ultra-violet curing system, methacrylate light curing agent monomer is important component part, it
Can be used for diluting oligomer, reduce viscosity, particularly with molecular weight oligomers system, reach curing system desired glutinous
Degree, and Light Curing is participated in, the curing rate of system is determined together with photosensitizer, while being reduced to up to needed for being fully cured
The time wanted, the physical and mechanical property of the photo-cur ing kinetics, extent of polymerization and generated cured film of system is affected, increase and hand over
Connection density, the final performance for determining product.Light curing agent monomer be divided into methyl acrylic ester, vinyl-based, vinyl ethers,
Epoxiess etc.；Also free radical type and the big class of cationic two can be divided into.Methyl acrylic ester, it is vinyl-based be typical light consolidate
Change reactive diluent, curing reaction is carried out by radical polymerization.At present, common on market light curing agent monomer is most
For acrylic ester monomer.
The monomer of different degrees of functionality is that degree of functionality is bigger, hardness is higher on the universal law that hardness of film affects, therefore is increased
Plus the consumption of polyfunctional monomer, hardness of film can be improved.To same functionality monomer, monomer structure also has very big shadow to hardness of film
Ring, polyfunctional monomer is used in a large number in photocureable coating system, increased hardness of film, but adhesive force, resistance to punching
Hitting property etc. has declined, thus can using some have rigid structure low degree of functionality monomer increase hardness of film it is same
When, there is preferable adhesive force again to material.Common mono-functional reactive's monomer lower crosslink density, have impact on the painting after photocuring
Film properties, the problems such as the high polyfunctional group photoactive monomer of crosslink density easily causes larger volume contraction, therefore, design and
Exploitation has diluting power strong, low surface tension, low volume shrinkage factor, has swollen material ability, and after solidifying film have compared with
Application of the new type functional esters of acrylic acid photocuring activated monomer of good hardness and resistance to photocuring film material has
Significance.
The content of the invention
Present patent application is expanded the purposes of solketal, and using ester exchange reaction, synthesis dimethyl two dislikes penta
Alkanol methacrylate light curing agent, and photocuring film is prepared under ultraviolet lighting, the result of study to solidifying film character
Show, its hardness, adhesive force, thermostability, resistance to water are good.
The structural formula of the dimethyl dioxin-pentane alcohol methacrylate light curing agent monomer is：
Prepare above-mentioned dimethyl dioxin-pentane alcohol methacrylate light curing agent monomer to concretely comprise the following steps：
Solketal synthesizes
It is acetone by mol ratio:Glycerol=1:1.4, catalyst p-methyl benzenesulfonic acid consumption is 2gmol-1(it is with acetone
Basis), the silica gel that changes colour (water that adsorption reaction is produced) consumption is 1gmol-1(based on acetone), is added to returned cold
In the 50mL flasks of solidifying pipe, magnetic stirring apparatuss are opened, after backflow is heated at 80 DEG C, then reacted 6 hours, reaction terminates
Afterwards, a small amount of Na is added in flask2CO3Neutralization acidic catalyst to reaction solution is in alkalescence, recycles Rotary Evaporators to this
Solution is rotated, and removes unreacted raw material acetone, and remaining liq is carried out into vacuum distillation, and temperature is 120-130 DEG C, pressure
Under the conditions of power -0.1Mpa, the fraction of collection is solketal product.
2) dimethyl dioxin-pentane alcohol methacrylic acid Lipase absobed
It is solketal by mol ratio:Methyl methacrylate=1:4, the consumption of hydroquinone of polymerization retarder is acetone contracting
The 0.6% of both glycerol and methyl methacrylate gross mass, and the catalyst dibutyltin cinnamic acid two of solketal quality 3%
Butyl tin, adds to 50mL and is equipped with the there-necked flask of condensing reflux pipe and water knockout drum, unlatching magnetic agitation, heat temperature raising,
Controlling reaction temperature is reacted 8 hours at 110 DEG C, has the azeotrope of methyl methacrylate and methanol in course of reaction in 55-75
DEG C it is distilled out of, after reaction terminates, carries out vacuum distillation, in 80 DEG C of temperature, under the conditions of pressure -0.1Mpa, further removes not anti-
The methyl methacrylate answered and by-product carbinol, obtain reacting coarse product --- and oxazole alkanols methacrylate light is consolidated
Agent monomer.
In photocureable coating, oligomer is above-mentioned dimethyl dioxin-pentane alcohol methacrylate light curing agent monomer applications
Modified epoxy acrylate resin RJ34713, light trigger is 184, prepares cured film.
Specific embodiment
The present invention is further elucidated with reference to specific embodiment, but embodiment is not intended to limit protection scope of the present invention.
Embodiment：
(1) solketal synthesis
It is acetone by mol ratio:Glycerol=1:1.4, catalyst p-methyl benzenesulfonic acid consumption is 2gmol-1(it is with acetone
Basis), using discoloration silica gel, its consumption is 1gmol to the water that adsorption reaction is produced-1(based on acetone), is added to and carries
In the 50mL flasks of reflux condensing tube, magnetic stirring apparatuss are opened, after backflow is heated at 80 DEG C, then react 6 hours, instead
After should terminating, a small amount of Na is added in flask2CO3Neutralization acidic catalyst to reaction solution is in alkalescence, recycles rotary evaporation
Instrument is rotated to this solution, removes unreacted raw material acetone, and remaining liq is carried out into vacuum distillation, and temperature is 120-130
DEG C, under the conditions of pressure -0.1Mpa, the fraction of collection is solketal product.Product is rolled on Abbe refractometer
Rate measure is penetrated, its refractive index is measured and is kissed substantially for solketal refractive index (1.433-1.435) in 1.4355, with list of references
Close.
(2) dimethyl dioxin-pentane alcohol methacrylic acid Lipase absobed
It is solketal by mol ratio:Methyl methacrylate=1:4, the consumption of hydroquinone of polymerization retarder is acetone contracting
The 0.6% of both glycerol and methyl methacrylate gross mass, and the catalyst dibutyltin cinnamic acid two of solketal quality 3%
Butyl tin, adds to 50mL and is equipped with the there-necked flask of condensing reflux pipe and water knockout drum, unlatching magnetic agitation, heat temperature raising,
Controlling reaction temperature is reacted 8 hours at 110 DEG C, has the azeotrope of methyl methacrylate and methanol in course of reaction in 55-75
DEG C it is distilled out of, after reaction terminates, carries out vacuum distillation, in 80 DEG C of temperature, under the conditions of pressure -0.1Mpa, further removes not anti-
The methyl methacrylate answered and by-product carbinol, obtain reacting coarse product --- and oxazole alkanols methacrylate light is consolidated
Agent monomer.
(3) preparation of photocuring film
Monomer dimethyl dioxin-pentane alcohol methacrylate, the initiator 1- hydroxy-cyclohexyl benzene that step (2) is synthesized
Base ketone light, oligomer modified epoxy acrylate resin, are added in beaker by the cured film proportioning of table 1, are stirred until light
Initiator all dissolves, and is made into paint binder.
The basic recipe of the cured film of table 1
The paint binder for preparing is smeared on the glass sheet, then sheet glass is put into into 18 volts of ultra violet lamps, lamp away from for
15 centimetres, until cured film reaches surface drying, hardening time is 25 minutes, that is, obtain cured film.Through test, the solidification film hardness
According to GB/T6739-1996 " hardness of paint film pencil algoscopy " carry out test for 2H, adhesive force according to GB/T9286-1998 standards
It is measured as 3.
Claims (2)
1. a kind of dimethyl dioxin-pentane alcohol methacrylate monomer, it is characterised in that the dimethyl dioxin-pentane alcohol methyl
The structural formula of acrylate monomer is：
2. dimethyl dioxin-pentane alcohol methacrylate monomer according to claim 1, it is characterised in that described two
It is low that methyl dioxolane alcohol methacrylate monomer is used for ultraviolet light polymerization modified epoxy acrylate resin as light curing agent
Polymers, makes epoxy acrylic resin oligomer form cured film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610968412.3A CN106588860A (en) | 2016-11-06 | 2016-11-06 | Dimethyl dioxane pentyl alkanol methacrylate monomer and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610968412.3A CN106588860A (en) | 2016-11-06 | 2016-11-06 | Dimethyl dioxane pentyl alkanol methacrylate monomer and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106588860A true CN106588860A (en) | 2017-04-26 |
Family
ID=58590669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610968412.3A Pending CN106588860A (en) | 2016-11-06 | 2016-11-06 | Dimethyl dioxane pentyl alkanol methacrylate monomer and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106588860A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110272408A (en) * | 2018-03-16 | 2019-09-24 | 杭州盛弗泰新材料科技有限公司 | A kind of preparation method of light curing agent dimethyl dioxin-pentane alcohol methacrylate |
| CN114790187A (en) * | 2022-04-10 | 2022-07-26 | 河北凯瑞化工有限公司 | Preparation method and application of oxacycloalkane |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194547A (en) * | 1990-06-08 | 1993-03-16 | Dainippon Ink & Chemicals, Inc. | Anionic living polymers, their derivatives and composition comprising them |
| US20020042549A1 (en) * | 1999-04-16 | 2002-04-11 | Barry Charles Holdstock | Process for the preparation of a diol |
| JP2004059435A (en) * | 2002-07-24 | 2004-02-26 | Osaka Organic Chem Ind Ltd | Method for producing dioxolane compound |
| CN102653576A (en) * | 2010-12-02 | 2012-09-05 | 罗门哈斯电子材料有限公司 | Polymers, photoresist compositions and methods of forming photolithographic patterns |
-
2016
- 2016-11-06 CN CN201610968412.3A patent/CN106588860A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194547A (en) * | 1990-06-08 | 1993-03-16 | Dainippon Ink & Chemicals, Inc. | Anionic living polymers, their derivatives and composition comprising them |
| US20020042549A1 (en) * | 1999-04-16 | 2002-04-11 | Barry Charles Holdstock | Process for the preparation of a diol |
| JP2004059435A (en) * | 2002-07-24 | 2004-02-26 | Osaka Organic Chem Ind Ltd | Method for producing dioxolane compound |
| CN102653576A (en) * | 2010-12-02 | 2012-09-05 | 罗门哈斯电子材料有限公司 | Polymers, photoresist compositions and methods of forming photolithographic patterns |
Non-Patent Citations (1)
| Title |
|---|
| JUI-HSIANG LIU ET AL.: "Preparation and Characterization of Novel Polymers Having Pendent Ketal Moieties for Positive Photoresists", 《MACROMOLECULAR CHEMISTRY AND PHYSICS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110272408A (en) * | 2018-03-16 | 2019-09-24 | 杭州盛弗泰新材料科技有限公司 | A kind of preparation method of light curing agent dimethyl dioxin-pentane alcohol methacrylate |
| CN114790187A (en) * | 2022-04-10 | 2022-07-26 | 河北凯瑞化工有限公司 | Preparation method and application of oxacycloalkane |
| CN114790187B (en) * | 2022-04-10 | 2024-03-05 | 河北凯瑞化工有限公司 | Preparation method and application of oxacycloalkane |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1754915B (en) | Silicone resin composition and molded product thereof | |
| CN101875710B (en) | Siloxane-group light-initiated polyacrylic ester/silicon dioxide nanometer material and preparation method thereof | |
| CN101747594A (en) | Epoxy acrylate prepolymer resin and preparation method thereof and application in photocurable coating | |
| CN108384406B (en) | Graphene oxide UV (ultraviolet) curing coating and preparation method thereof | |
| CN107501463A (en) | A kind of ultraviolet light self-crosslinking polyacrylates and preparation method thereof | |
| CN101831176B (en) | Solidification composition of aryl mercaptan-olefinic unsaturated double-bond polyether sulfone | |
| CN101962430A (en) | Method for producing ultraviolet curable amino acrylate resin | |
| CN106588860A (en) | Dimethyl dioxane pentyl alkanol methacrylate monomer and application thereof | |
| CN113388051A (en) | Styrene-maleic anhydride esterified substance, preparation method and application thereof | |
| CN110229317B (en) | UV-curable unsaturated polyester resin with high vinyl functionality, and preparation method and application thereof | |
| CN113121792B (en) | UV-cured fluorine-modified waterborne epoxy resin and preparation method thereof | |
| CN101983959B (en) | Multifunctional acrylic ester monomer for photopolymerization and preparing method thereof | |
| CN113248636B (en) | Thioxanthone visible light initiator, preparation method and application | |
| JP2015021045A (en) | Optical three-dimensional contouring resin composition consisting of cyclic ether group-containing (meth)acrylate | |
| CN106543448A (en) | A kind of ultraviolet light high speed curable dendroid resin and its divergent method preparation method and applications | |
| CN106479328A (en) | A kind of quick-dry type ultraviolet-cured paint | |
| Montefusco et al. | New difunctional fluoro-epoxide monomers: synthesis, photopolymerization and characterization | |
| Palanisamy et al. | Tetrafunctional acrylates based on β-hydroxy alkyl amides as crosslinkers for UV curable coatings | |
| CN115710457B (en) | Ultraviolet light curing composition and preparation method and application thereof | |
| CN105669446A (en) | Ultraviolet-curable resin and preparation method thereof | |
| JP4880249B2 (en) | Photoradical crosslinking polymer and photocurable resin composition | |
| CN103435757B (en) | A kind of UV coating fluorine-containing epoxy FRP pipe and preparation method thereof | |
| CN107075016B (en) | Triacrylate compound and its manufacturing method and composition | |
| CN105037158B (en) | Dihydric alcohol hyperbranched monomer based on maleic anhydride and preparation method thereof | |
| CN113816929A (en) | Aliphatic epoxy compound and pouring sealant prepared from same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170426 |
|
| RJ01 | Rejection of invention patent application after publication |