CN108676125B - Organic silicon graft modified glass ultraviolet curing resin - Google Patents
Organic silicon graft modified glass ultraviolet curing resin Download PDFInfo
- Publication number
- CN108676125B CN108676125B CN201810569717.6A CN201810569717A CN108676125B CN 108676125 B CN108676125 B CN 108676125B CN 201810569717 A CN201810569717 A CN 201810569717A CN 108676125 B CN108676125 B CN 108676125B
- Authority
- CN
- China
- Prior art keywords
- diisocyanate
- parts
- organic silicon
- grafted
- graft modified
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides an organic silicon grafted and modified glass ultraviolet curing resin, which comprises glycidyl methacrylate, organic silicon grafted methyl acrylate carbamate, methacrylate, methacryloxy functional group silane and an antioxidant 1010; the preparation method of the organic silicon grafted methacrylic carbamate uses high-activity hydroxyl generated by hydrolysis of dichlorosilane to perform silane grafting reaction with isocyanate grafted to polycaprolactone diol; adding a second batch of diisocyanate, and reacting with dihydroxy silane grafted to isocyanate to keep the activity of the reaction of the oligomer and the methacrylic acid hydroxy ester; finally, adding methacrylic acid hydroxy ester to prepare organosilicon grafted methacrylic acid carbamate with uniform silane grafting and high silicon content; the organosilicon grafted methacrylic acid carbamate can obviously improve the hardness, wear resistance, ethanol resistance and boiling resistance of the light-cured resin.
Description
Technical Field
The invention relates to the field of light-cured resin for glass, in particular to glass ultraviolet light-cured resin modified by organic silicon grafting.
Background
At present, most of the glass ultraviolet curing resins used in the market have poor adhesive force and moisture resistance, and are mainly represented as follows: the initial adhesive strength satisfies the requirements, but the adhesive strength is greatly reduced with the increase of the adhesive time, particularly after being left in a humid and hot environment for a certain period of time. In addition, the ultraviolet curing resin is difficult to store and poor in environmental protection property, and has the problems of large curing shrinkage rate, low curing speed and large product brittleness in the using process.
Disclosure of Invention
In view of the problems in the background art, the invention aims to provide a glass ultraviolet curing resin modified by grafting organic silicon, which improves the adhesion, hardness, boiling resistance, ethanol resistance and wear resistance of the light curing resin and glass and solves the problems of easy peeling and poor weather resistance of the existing light curing resin.
In order to achieve the purpose, the invention provides an organosilicon graft modified glass ultraviolet curing resin which is prepared from the following raw materials in percentage by mass:
further, the preparation method of the organic silicon grafted methyl acrylic carbamate comprises the following steps:
(1) heating and drying polycaprolactone diol for 3 hours at the temperature of 105 ℃ and the vacuum degree of 0.1MPa, and then cooling to 80-90 ℃ to obtain pretreated polycaprolactone diol;
(2) putting 100 parts of the preprocessed polycaprolactone diol obtained in the step (1) and 1-3 parts of a catalyst into a reaction vessel protected by inert gas by mole fraction, stirring uniformly, adding 100 parts of diisocyanate in a molten state by mole fraction in batches, stirring continuously, and reacting for 2-3 hours at the temperature of 80-90 ℃ to obtain a pre-reaction base solution;
(3) adding 10-20 parts of dichlorosilane dropwise into the pre-reaction base liquid in the step (2) under the protection of a flowing inert gas by mole fraction and keeping stirring, then adding 20-40 parts of deionized water dropwise, reacting for 2 hours at the temperature of 80-90 ℃, finally adding 100 parts of diisocyanate in a molten state, and continuing to react for 2-3 hours to obtain a grafting reaction base liquid;
(4) adding 50 parts by mole of hydroxy methacrylate into the grafting reaction base liquid in the step (3), reacting completely, distilling, and cooling to obtain the organic silicon grafted methacrylic carbamate.
Further, the diisocyanate is one or a combination of hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, toluene diisocyanate, dimethyl methane diisocyanate and xylylene diisocyanate.
Further, the hydroxyl methacrylate is one or a combination of hydroxyethyl methacrylate and hydroxypropyl methacrylate.
Further, the dichlorosilane is one of dimethyldichlorosilane, diethyldichlorosilane, diisopropyldichlorosilane and phenyldichlorosilane.
Further, the catalyst is one of dibutyltin laurate and stannous octoate.
Further, the inert gas is one of nitrogen and argon.
The invention mixes methacrylic acid epoxy ester and organic silicon grafted methacrylic acid carbamate according to a certain proportion as photosensitive matrix resin, and adopts an original preparation process: under the protection of inert gas, utilizing intermediate dihydroxy silane generated after dichlorosilane and water molecules are subjected to hydrolysis reaction, wherein the dihydroxy silane has high-activity hydroxyl and can be subjected to grafting reaction with isocyanato grafted to polycaprolactone diol, and the dihydroxy silane is an oligomer with the polymerization degree of less than 3; then adding a second batch of diisocyanate, and reacting with dihydroxy silane grafted to isocyanate to keep the activity capable of reacting with the hydroxy methacrylate; finally, adding methacrylic acid hydroxy ester to prepare organosilicon grafted methacrylic acid carbamate with uniform silane grafting and high silicon content; the organosilicon grafted methacrylic carbamate is a main factor for improving the hardness, the wear resistance, the ethanol resistance and the water boiling resistance of the ultraviolet curing resin.
Other features of the present invention and its advantages will become apparent from the following detailed description of exemplary embodiments of the invention.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to make the aforementioned objects, features and advantages of the invention more comprehensible.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
The organic silicon graft modified glass ultraviolet curing resin comprises the following raw materials in percentage by mass:
in the silicone graft-modified glass ultraviolet curable resin according to the present invention, the preparation method of the silicone graft-methacrylic urethane comprises the steps of:
(1) heating and drying polycaprolactone diol for 3 hours at the temperature of 105 ℃ and the vacuum degree of 0.1MPa, and then cooling to 80-90 ℃ to obtain pretreated polycaprolactone diol;
(2) putting 100 parts of the preprocessed polycaprolactone diol obtained in the step (1) and 1-3 parts of a catalyst into a reaction vessel protected by inert gas by mole fraction, stirring uniformly, adding 100 parts of diisocyanate in a molten state by mole fraction in batches, stirring continuously, and reacting for 2-3 hours at the temperature of 80-90 ℃ to obtain a pre-reaction base solution;
(3) adding 10-20 parts of dichlorosilane dropwise into the pre-reaction base liquid in the step (2) under the protection of a flowing inert gas by mole fraction and keeping stirring, then adding 20-40 parts of deionized water dropwise, reacting for 2 hours at the temperature of 80-90 ℃, finally adding 100 parts of diisocyanate in a molten state, and continuing to react for 2-3 hours to obtain a grafting reaction base liquid;
(4) adding 50 parts by mole of hydroxy methacrylate into the grafting reaction base liquid in the step (3), reacting completely, distilling, and cooling to obtain the organic silicon grafted methacrylic carbamate.
In the silicone graft-modified uv-curable resin for glass according to the present invention, the diisocyanate is one or a combination of hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, toluene diisocyanate, dimethyl methane diisocyanate, and xylylene diisocyanate.
In the silicone graft-modified glass ultraviolet curable resin according to the present invention, the hydroxy methacrylate is one or a combination of hydroxyethyl methacrylate and hydroxypropyl methacrylate.
In the organosilicon graft-modified glass ultraviolet curing resin, the dichlorosilane is one or a combination of dimethyldichlorosilane, diethyldichlorosilane, diisopropyldichlorosilane and phenyldichlorosilane.
In the organosilicon graft modified glass ultraviolet light curing resin, the catalyst is one of dibutyltin laurate and stannous octoate.
In the silicone graft-modified glass ultraviolet curable resin according to the present invention, the inert gas is one of nitrogen and argon.
The invention mixes methacrylic acid epoxy ester and organic silicon grafted methacrylic acid carbamate according to a certain proportion as photosensitive matrix resin, and adopts an original preparation process: under the protection of inert gas, utilizing intermediate dihydroxy silane generated after dichlorosilane and water molecules are subjected to hydrolysis reaction, wherein the dihydroxy silane has high-activity hydroxyl and can be subjected to grafting reaction with isocyanato grafted to polycaprolactone diol, and the dihydroxy silane is an oligomer with the polymerization degree of less than 3; then adding a second batch of diisocyanate, and reacting with dihydroxy silane grafted to isocyanate to keep the activity capable of reacting with the hydroxy methacrylate; finally, adding methacrylic acid hydroxy ester to prepare organosilicon grafted methacrylic acid carbamate with uniform silane grafting and high silicon content; the organosilicon grafted methacrylic carbamate is a main factor for improving the hardness, the wear resistance, the ethanol resistance and the water boiling resistance of the ultraviolet curing resin. The chemical reaction mechanism is as follows:
wherein the reaction equation of the hydrolysis of dichlorosilane to generate intermediate dihydroxysilane is
The glass uv curable resin grafted and modified with silicone according to the present invention will be described in detail with reference to specific examples.
Example 1
Weighing the following components in percentage by mass, mixing and uniformly stirring to prepare the organic silicon graft modified glass ultraviolet curing resin
Wherein, the preparation of the organosilicon grafted methacrylic acid carbamate comprises the following steps:
(1) heating and drying polycaprolactone diol for 3 hours at the temperature of 105 ℃ and the vacuum degree of 0.1MPa, and then cooling to 80 ℃ to obtain pretreated polycaprolactone diol;
(2) putting 100 parts of the preprocessed polycaprolactone diol obtained in the step (1) and 1 part of dibutyltin laurate into a reaction vessel protected by nitrogen together according to the mole fraction, stirring uniformly, adding 100 parts of molten hexamethylene diisocyanate according to the mole fraction in batches, stirring continuously, and reacting for 2 hours at the temperature of 80 ℃ to obtain a pre-reaction base solution;
(3) adding 10 parts of dimethyldichlorosilane dropwise into the pre-reaction base liquid in the step (2) under the protection of flowing nitrogen gas by mole fraction and keeping stirring, then adding 20 parts of deionized water dropwise, reacting for 2 hours at the temperature of 80 ℃, finally adding 100 parts of molten hexamethylene diisocyanate, and continuing to react for 2 hours to obtain a grafting reaction base liquid;
(4) adding 50 parts by mole of hydroxyethyl methacrylate into the grafting reaction base liquid in the step (3), reacting completely, distilling, and cooling to obtain the organic silicon grafted methyl methacrylate carbamate.
Example 2
Weighing the following components in percentage by mass, mixing and uniformly stirring to prepare the organic silicon graft modified glass ultraviolet curing resin
The preparation method of the organic silicon grafted methacrylic acid carbamate comprises the following steps:
(1) heating and drying polycaprolactone diol for 3 hours at the temperature of 110 ℃ and the vacuum degree of 0.1MPa, and then cooling to 90 ℃ to obtain pretreated polycaprolactone diol;
(2) putting 100 parts of the preprocessed polycaprolactone diol obtained in the step (1) and 3 parts of stannous octoate into a reaction container protected by argon together according to the mole fraction, stirring uniformly, adding 100 parts of molten isophorone diisocyanate according to the mole fraction in batches, stirring continuously, and reacting for 3 hours at the temperature of 90 ℃ to obtain a pre-reaction base solution;
(3) adding 20 parts of diethyldichlorosilane dropwise into the pre-reaction base liquid in the step (2) under the protection of flowing argon gas by mole fraction and keeping stirring, then adding 40 parts of deionized water dropwise, reacting for 2 hours at the temperature of 90 ℃, finally adding 100 parts of isophorone diisocyanate in a molten state, and continuing to react for 3 hours to obtain a grafting reaction base liquid;
(4) adding 50 parts by mole of hydroxypropyl methacrylate into the grafting reaction base liquid in the step (3), reacting completely, distilling, and cooling to obtain the organosilicon grafted methyl methacrylate carbamate.
Example 3
Weighing the following components in percentage by mass, mixing and uniformly stirring to prepare the organic silicon graft modified glass ultraviolet curing resin
The preparation method of the organic silicon grafted methacrylic acid carbamate comprises the following steps:
(1) heating and drying polycaprolactone diol for 3 hours at the temperature of 108 ℃ and the vacuum degree of 0.1MPa, and then cooling to 85 ℃ to obtain pretreated polycaprolactone diol;
(2) putting 100 parts of the preprocessed polycaprolactone diol obtained in the step (1) and 2 parts of stannous octoate into a reaction container protected by nitrogen together according to the mole fraction, stirring uniformly, adding 100 parts of molten dicyclohexylmethane diisocyanate according to the mole fraction in batches, stirring continuously, and reacting for 2.5 hours at the temperature of 85 ℃ to obtain a pre-reaction base solution;
(3) adding 15 parts of diisopropyldichlorosilane dropwise into the pre-reaction base liquid in the step (2) under the protection of flowing nitrogen gas by mole fraction and keeping stirring, then adding 30 parts of deionized water dropwise, reacting for 2 hours at the temperature of 85 ℃, finally adding 100 parts of molten dicyclohexylmethane diisocyanate, and continuing to react for 2.5 hours to obtain a grafting reaction base liquid;
(4) adding 50 parts by mole of hydroxypropyl methacrylate into the grafting reaction base liquid in the step (3), reacting completely, distilling, and cooling to obtain the organosilicon grafted methyl methacrylate carbamate.
Example 4
The procedure of example 1 was repeated, except that tolylene diisocyanate was used instead of hexamethylene diisocyanate and phenyldichlorosilane was used instead of dimethyldichlorosilane.
Example 5
The procedure was as in example 1 except that dimethylmethane diisocyanate was used instead of hexamethylene diisocyanate.
Example 6
The procedure was as in example 1 except that xylylene diisocyanate was used instead of hexamethylene diisocyanate.
Comparative example 1
Weighing the following components in percentage by mass, mixing and uniformly stirring to prepare the glass ultraviolet curing resin:
performance testing
1. Sample preparation
The photo-curing resin and the poly-p-phenylene diacrylate (photoinitiator) of each example are mixed according to the mass ratio of 100:2, uniformly mixed, vacuumed, defoamed, coated on a glass sheet subjected to electrostatic dust removal, and cured by ultraviolet irradiation at 50 ℃ to obtain a sample with the film thickness of 20 microns.
2. Sample testing
Adhesion force: one hundred lattice method (3M600,3 times);
pencil hardness: mitsubishi pencil (1KG force);
boiling resistance: soaking the sample at 100 deg.c for 1 hr;
ethanol resistance: soaking in absolute ethyl alcohol at 60 ℃ for 72 hours;
wear resistance: the abrasion resistance of the colored paint and the varnish is tested according to the standard rotating rubber grinding wheel method (GB/T1768-2006).
Performance comparison table
| Adhesion force | Hardness of pencil | Resistance to boiling in water | Resistance to ethanol | Wear resistance | |
| Example 1 | 5B | 3H | Without change | Without change | Without wearing through |
| Example 2 | 5B | 3H | Without change | Without change | Without wearing through |
| Example 3 | 5B | 3H | Without change | Without change | Without wearing through |
| Example 4 | 5B | 3H | Without change | Without change | Without wearing through |
| Example 5 | 5B | 3H | Without change | Without change | Without wearing through |
| Example 6 | 5B | 3H | Without change | Without change | Without wearing through |
| Comparative example 1 | 3B | 2H | Film peeling | Film wrinkling | Wearing-in |
The embodiment shows that the adhesive prepared by the organosilicon graft modified glass ultraviolet curing resin is relatively unmodified, has higher adhesive force, hardness, boiling resistance, ethanol resistance and wear resistance, and completely meets the industrial application requirements.
Although some specific embodiments of the present invention have been described in detail by way of illustration, it should be understood by those skilled in the art that the above illustration is only for the purpose of illustration and is not intended to limit the scope of the invention. It will be appreciated by those skilled in the art that modifications may be made to the above embodiments without departing from the scope and spirit of the invention. The scope of the invention is defined by the appended claims.
Claims (6)
1. The organic silicon graft modified glass ultraviolet curing resin is characterized by comprising the following raw materials in percentage by mass:
the preparation method of the organic silicon grafted methacrylic acid carbamate comprises the following steps:
(1) heating and drying polycaprolactone diol for 3 hours at the temperature of 105 ℃ and the vacuum degree of 0.1MPa, and then cooling to 80-90 ℃ to obtain pretreated polycaprolactone diol;
(2) putting 100 parts of the preprocessed polycaprolactone diol obtained in the step (1) and 1-3 parts of a catalyst into a reaction vessel protected by inert gas by mole fraction, stirring uniformly, adding 100 parts of diisocyanate in a molten state by mole fraction in batches, stirring continuously, and reacting for 2-3 hours at the temperature of 80-90 ℃ to obtain a pre-reaction base solution;
(3) adding 10-20 parts of dichlorosilane dropwise into the pre-reaction base liquid in the step (2) under the protection of a flowing inert gas by mole fraction and keeping stirring, then adding 20-40 parts of deionized water dropwise, reacting for 2 hours at the temperature of 80-90 ℃, finally adding 100 parts of diisocyanate in a molten state, and continuing to react for 2-3 hours to obtain a grafting reaction base liquid;
(4) adding 50 parts by mole of hydroxy methacrylate into the grafting reaction base liquid in the step (3), reacting completely, distilling, and cooling to obtain the organic silicon grafted methacrylic carbamate.
2. The silicone graft modified uv-curable glass resin according to claim 1, wherein the diisocyanate is one or a combination of hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, toluene diisocyanate, and xylylene diisocyanate.
3. The silicone graft modified glass ultraviolet curable resin according to claim 1, wherein the hydroxy methacrylate is one or a combination of hydroxyethyl methacrylate and hydroxypropyl methacrylate.
4. The silicone graft modified uv curable glass resin according to claim 1, wherein the dichlorosilane is one or a combination of dimethyldichlorosilane, diethyldichlorosilane, diisopropyldichlorosilane, and phenyldichlorosilane.
5. The silicone graft modified glass ultraviolet curable resin according to claim 1, wherein the catalyst is one of dibutyltin laurate and stannous octoate.
6. The silicone graft modified glass uv curable resin according to claim 1, wherein the inert gas is one of nitrogen and argon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810569717.6A CN108676125B (en) | 2018-06-05 | 2018-06-05 | Organic silicon graft modified glass ultraviolet curing resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810569717.6A CN108676125B (en) | 2018-06-05 | 2018-06-05 | Organic silicon graft modified glass ultraviolet curing resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108676125A CN108676125A (en) | 2018-10-19 |
| CN108676125B true CN108676125B (en) | 2020-04-28 |
Family
ID=63809832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810569717.6A Active CN108676125B (en) | 2018-06-05 | 2018-06-05 | Organic silicon graft modified glass ultraviolet curing resin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108676125B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321984B (en) * | 2020-11-12 | 2023-03-10 | 广东省瑞晟新材料科技有限公司 | Silicon-modified 3D printing photocuring resin, 3D printing product and application thereof |
| CN114292574B (en) * | 2021-08-13 | 2022-08-05 | 荆门科顺新材料有限公司 | Single-component polyurethane waterproof paint and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000007979A (en) * | 1998-06-23 | 2000-01-11 | Nippon Paper Industries Co Ltd | Coating resin composition for polyolefin and its production |
| CN102559038A (en) * | 2012-02-16 | 2012-07-11 | 长沙市原鹏化工科技有限公司 | Organosilicon-modified polyurethane-acrylic ester photocurable coating and preparation method thereof |
| CN102585689A (en) * | 2011-12-30 | 2012-07-18 | 深圳市嘉卓成科技发展有限公司 | Voltage-withstand photo-cured anode oxidation coating, as well as preparation method and using method thereof |
| CN103881031A (en) * | 2014-02-20 | 2014-06-25 | 常州市嘉诺有机硅有限公司 | Special organic silicon resin for photocureable coating and preparation process of organic silicon resin |
-
2018
- 2018-06-05 CN CN201810569717.6A patent/CN108676125B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000007979A (en) * | 1998-06-23 | 2000-01-11 | Nippon Paper Industries Co Ltd | Coating resin composition for polyolefin and its production |
| CN102585689A (en) * | 2011-12-30 | 2012-07-18 | 深圳市嘉卓成科技发展有限公司 | Voltage-withstand photo-cured anode oxidation coating, as well as preparation method and using method thereof |
| CN102559038A (en) * | 2012-02-16 | 2012-07-11 | 长沙市原鹏化工科技有限公司 | Organosilicon-modified polyurethane-acrylic ester photocurable coating and preparation method thereof |
| CN103881031A (en) * | 2014-02-20 | 2014-06-25 | 常州市嘉诺有机硅有限公司 | Special organic silicon resin for photocureable coating and preparation process of organic silicon resin |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108676125A (en) | 2018-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5557274B2 (en) | Ultraviolet curable hard coat resin composition, hard coat film and hard coat molded article using the same | |
| CN104558501B (en) | A kind of ultraviolet and moisture dual cure type modified polyurethane and preparation method thereof | |
| CN102079810B (en) | Synthesis and application of light-cured polyurethane-acrylic acid-epoxy resin adhesive | |
| CN108977056B (en) | Ultra-wear-resistant ultraviolet curing coating | |
| CN103370384A (en) | UV curable coating composition having self-healing capabilities, coating film and method for preparing coating film | |
| JP6032383B1 (en) | Active energy ray-curable resin composition, paint, coating film, and film | |
| KR20100026014A (en) | Hard-coating composition and hard-coating film | |
| CN109251301B (en) | Preparation method and composition of photopolymerization organosilicon polyurethane acrylate water-based oligomer | |
| CN112831278B (en) | Photocurable resin composition | |
| CN108676125B (en) | Organic silicon graft modified glass ultraviolet curing resin | |
| JP2015108093A (en) | Curable resin composition, cured article and laminate | |
| CN112708099B (en) | Nano silica sol hybrid polyurethane acrylate with photo-curable double-bond groups and preparation method thereof | |
| CN113088238A (en) | Preparation method of high-peel-force fast-packaging OCA adhesive for low-surface-energy interface lamination | |
| JP2011042770A (en) | Active energy ray-curable oligomer, active energy ray-curable resin composition, cured coating film, and plastic film | |
| Jiao et al. | High tensile strength UV-cured castor oil-based silicone-modified polyurethane acrylates | |
| KR20130120424A (en) | Thermoset coating composition having self-healing capacity, coating film, and preparation method of coating film | |
| CN111978502B (en) | Urethane oil acrylate photocuring resin and preparation method thereof | |
| CN115558112B (en) | Low-migration silicon-containing macromolecular photoinitiator and preparation method and application thereof | |
| JP2016221922A (en) | Film for processing, processed film, and method for producing them | |
| CN112851902B (en) | Nano calcium carbonate modified waterborne polyurethane acrylate with photosensitive group and preparation method thereof | |
| CN116218006A (en) | Antistatic optical protection film and preparation method thereof | |
| CN109762131B (en) | Siloxane end-capping agent, preparation method thereof and light-moisture dual-curing polyurethane pressure-sensitive adhesive applying end-capping agent | |
| Yoon et al. | UV-curable water-borne polyurethane primers for aluminum and polycarbonate interfaces | |
| CN112321842A (en) | Ultraviolet light curing hyperbranched acrylate resin and preparation method thereof | |
| CN105801805B (en) | Photopolymerization urethane acrylate and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |