CN102718941A - Preparation method of silane macromolecular coupling agent polymer system - Google Patents
Preparation method of silane macromolecular coupling agent polymer system Download PDFInfo
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Abstract
The invention belongs to the technical field of chemical production, and provides a preparation method of a silane macromolecular coupling agent polymer system. According to the preparation method, polyurethane and epoxy resin form a composite system with superior comprehensive performance by mutual winding of molecular chains and chemical reaction; the amino-containing siloxane is adopted to modify the polyurethane-epoxy resin multi-component polymer system so as to prepare a silane macromolecular coupling agent; and the amino of micromolecular siloxane can react with the isocyanate group in the polyurethane and the epoxy group in the epoxy resin so as to form the macromolecular coupling agent which has an interpenetrating polymer network structure. With such interpenetrating polymer network structure, the macromolecular coupling agent can integrate the functions of the organic polymer and the coupling agent; the flexibility of the macromolecular coupling agent is adjusted by changing the content of polyurethane; the strength of the macromolecular coupling agent is adjusted by changing the content of the epoxy resin; and when an inorganic reinforcing material is added to the polymer matrix after being treated by the macromolecular coupling agent, the polymer composite material can form a better interface, and the overall compressive performance of the composite material is improved.
Description
Technical field
The invention belongs to chemical production technical field, relate in particular to a kind of preparation method of silicane macromolecular coupling agent polymeric system.
Background technology
Along with the continuous promotion and application of polymer composite, the requirement of the over-all properties of polymer composite is further improved.A principal element of decision Inorganic Fillers Filled polymer composites physical and mechanical property is mineral filler and matrix in the composite system consistency and interface bonding state.For improving the consistency between mineral filler and the matrix, need carry out surface treatment to mineral filler.The solution that general employing silane coupling agent etc. are handled its surface.Coupling agent can make the physical and chemical performance of matrix material be significantly improved in 1% to 3% of interpolation base-material amount usually.
Silane coupling agent contains activated siloxy group, can with the surface of mineral filler form firm combine and coupling agent in organic moiety and polymeric matrix between produce physics and chemical interaction and reach the consistency that improves between inorganics and organism.But formed interfacial layer is than thin and fragile in matrix material for the small molecules coupling agent, and effect is undesirable.Therefore existing small molecules coupling agent can not satisfy the high performance requirements of matrix material fully.When adopting macromolecular coupling agent; On the one hand because of the coupling agent molecule chain of inorganic filler surface can with the interactions such as polymer molecule chain formation intensive physics winding of matrix; On the other hand through changing the chain structure and the composition of macromole silane coupling agent; Can regulate the intensity and the flexible control and the optimization that realizes interface structure between filler in the matrix material and the matrix of silane macromolecular coupling agent, thereby reach the purpose that improves composite property.
Summary of the invention
The invention provides a kind of preparation method of silicane macromolecular coupling agent polymeric system; Be intended to solve silane coupling agent and contain activated siloxy group; Thereby can with the surface of mineral filler form firm combine and coupling agent in organic moiety and polymeric matrix between produce physics and chemical interaction and reach the consistency that improves between inorganics and organism and set up the interfacial layer that adapts to; But the small molecules coupling agent in matrix material formed interfacial layer than thin and fragile, the unfavorable problem of effect.
The object of the present invention is to provide a kind of preparation method of silicane macromolecular coupling agent polymeric system, this preparation method may further comprise the steps:
Further, the prepared silicane macromolecular coupling agent of this preparation method is the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin.
Further, in step 2, the mol ratio of contained total hydroxy is 1.5～2.5/1 in contained NCO of vulcabond and polyethers, the epoxy resin.
Further, in step 3, γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine account for 10%～40% of NCO mass contg.
Further, the vulcabond that in step 2, is adopted is a ditan-4,4 '-vulcabond or tolylene diisocyanate.
Further, the bisphenol A type epoxy resin that in step 1, adopts is bisphenol A type epoxy resin E-44 or E-51.
Further, the polyethers that in step 1, adopts is polyethers N330 or polyethers 2000.
Further, the catalyzer that in step 4, adopts is dibutyl tin laurate, stannous octoate, quality be contain the polyurethane/epoxy resin silicane macromolecular coupling agent system 0.01%～2%.
Further, the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin that this preparation method is prepared is applied in preparation matrix material, damping material, Reinforced Rubber, tackiness agent, automotive industry with in material, medical macromolecular materials and the low temperature material.
The preparation method of silicane macromolecular coupling agent polymeric system provided by the invention; By urethane and two kinds of polymkeric substance of epoxy resin through molecular chain twine each other, chemical reaction; Form the compound system of excellent combination property; To have better consistency and some performances of matrix material are improved between polymkeric substance and inorganic reinforcement in order to make in the matrix material, adopt the amino-contained siloxanes that urethane-epoxy resin multicomponent polymeric system is carried out modification and prepare the silane macromolecular coupling agent; The amido of small molecules siloxanes can with the epoxy reaction in isocyanate groups in the urethane and the epoxy resin; Make it to become the macromolecular coupling agent that contains the interpenetrating polymer networks structure; This specific molecule structure and composition make it compile organic polymer and the coupling agent function is an one; Change the flexibility that polyurethane content is regulated macromolecular coupling agent,, after handling inorganic reinforcement, add in the polymeric matrix with it through changing the intensity that epoxy resin content is regulated macromolecular coupling agent; Can make polymer composites form reasonable interface, reach the purpose that improves matrix material overall synthetic performance; The preparation method of this silicane macromolecular coupling agent polymeric system, simple and practical, have stronger popularization and using value.
Description of drawings
Fig. 1 is the preparing method's of the silicane macromolecular coupling agent polymeric system that provides of the embodiment of the invention realization flow figure;
Fig. 2 be the embodiment of the invention provide work as urethane: the epoxy resin mass ratio is 90: 10, and the silicane macromolecular coupling agent system of different polyethers 2000 content is solidified the infrared spectrum of back sample.
Embodiment
In order to make the object of the invention, technical scheme and advantage clearer,, the present invention is further specified below in conjunction with accompanying drawing and embodiment.Should be appreciated that specific embodiment described herein only in order to explanation the present invention, and be not used in the qualification invention.
Fig. 1 shows the preparing method's of the silicane macromolecular coupling agent polymeric system that the embodiment of the invention provides realization flow.
This preparation method may further comprise the steps:
In step S101,, be below 0.01% to the moisture content mass percent two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin raw material drying;
In step S102; Exsiccant two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin and vulcabond are added reaction kettle; React 3～6 hours generation urethane-epoxy resin multicomponent polymeric systems under the 60-80 ℃ of condition, bisphenol A epoxide resin accounts for the 5%-20% of urethane-epoxy resin multicomponent polymeric system quality percentage composition;
In step S103, add γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine, under 30-60 ℃ of condition, reacted 1～3 hour, make the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin;
In step S104, add catalyzer in the silicane macromolecular coupling agent system of polyurethane/epoxy resin, stir and airtight preservation.
In embodiments of the present invention, the prepared silicane macromolecular coupling agent of this preparation method is the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin.
In embodiments of the present invention, in step S102, the mol ratio of contained total hydroxy is 1.5～2.5/1 in contained NCO of vulcabond and polyethers, the epoxy resin.
In embodiments of the present invention, in step S103, γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine account for 10%～40% of NCO mass contg.
In embodiments of the present invention, the vulcabond that in step S102, is adopted is a ditan-4,4 '-vulcabond or tolylene diisocyanate.
In embodiments of the present invention, the bisphenol A type epoxy resin that in step S101, adopts is bisphenol A type epoxy resin E-44 or E-51.
In embodiments of the present invention, the polyethers that in step S101, adopts is polyethers N330 or polyethers 2000.
In embodiments of the present invention, the catalyzer that in step S104, adopts is dibutyl tin laurate, stannous octoate, quality be contain the polyurethane/epoxy resin silicane macromolecular coupling agent system 0.01%～2%.
In embodiments of the present invention; The silicane macromolecular coupling agent that contains the polyurethane/epoxy resin that this preparation method is prepared is applied in preparation matrix material, damping material, Reinforced Rubber, tackiness agent, automotive industry with in material, medical macromolecular materials and the low temperature material.
Below in conjunction with accompanying drawing and specific embodiment application principle of the present invention is further described.
The technical scheme that the present invention solves the problems of the technologies described above employing provides a kind of preparation method who contains the silicane macromolecular coupling agent of polyurethane/epoxy resin, contains the following step:
1) two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin is dry, be below 0.01% to the moisture mass percent;
2) exsiccant two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin and vulcabond are added reaction kettle generation urethane-epoxy resin multicomponent polymeric system;
3) add the reaction of γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine in urethane-epoxy resin multicomponent polymeric system and generate the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin;
4) the silicane macromolecular coupling agent of polyurethane/epoxy resin adds catalyzer, stirs airtight preservation.
Wherein all contain hydroxyl in polyethers, the bisphenol A type epoxy resin, contain in the vulcabond NCO can with hydroxyl reaction; Step 2. on the polyethers, bisphenol A type epoxy resin hydroxyl all with the isocyanic ester radical reaction, thereby couple together epoxy resin and urethane the urethane-epoxy resin multicomponent polymeric system of formation performance complement; Step 3. in, γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] thus the reaction of amine and isocyanate groups and epoxide group generates the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin.The different add-ons of urethane and epoxy resin can be regulated the flexibility and the intensity of silane macromolecular coupling agent.
Work out a kind of technological process and processing condition according to such scheme:
1. wetting ability two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin is dry, be below 0.01% to the moisture content mass percent;
2. exsiccant two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin and vulcabond are added reaction kettle; React 3～6 hours generation urethane-epoxy resin multicomponent polymeric systems under the 60-80 ℃ of condition, bisphenol A epoxide resin accounts for the 5%-20% of urethane-epoxy resin multicomponent polymeric system quality percentage composition;
3. add γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine, reacted 1～3 hour under 30～60 ℃ of conditions, make the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin; Wherein the mol ratio of contained total hydroxy is 1.5～2.5/1 in contained NCO of vulcabond and polyethers, the epoxy resin; Described γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine account for 10%～40% of isocyanate groups amount percentage composition;
4. the silicane macromolecular coupling agent of polyurethane/epoxy resin adds catalyzer, stirs airtight preservation.
Polyethers is: polyethers N330, polyethers 2000.
Vulcabond is a ditan-4,4 '-vulcabond, Toluene-2,4-diisocyanate, 4-vulcabond.
Epoxy resin is bisphenol A type epoxy resin E-44 or E-51.
Catalyzer is dibutyl tin laurate, stannous octoate, quality be contain the polyurethane/epoxy resin silane macromolecular coupling agent system 0.01%～2%.
The used solvent of catalyzer is ETHYLE ACETATE, 2-butanone or their mixture, and it adds quality is 100%～300% of catalyst quality.
Embodiment 1: raw material drying to moisture content mass percent is below 0.01%; With molecular weight is that 4800 polyethers N330, molecular weight are that 2000 polyethers 2000 and bisphenol A type epoxy resin E-44 add in 60 ℃ of there-necked flasks; Add Toluene-2,4-diisocyanate after stirring half a hour; Behind the 4-vulcabond (TDI) temperature is risen to 80 ℃ of reactions 3 hours, obtain urethane-epoxy resin multicomponent polymeric; Be cooled to 60 ℃, add γ-amine propyl-triethoxysilicane stirring reaction after 1 hour, the ethyl acetate solution of the dibutyl tin laurate of adding 0.01% under the room temperature, the airtight preservation in back stirs.Bisphenol A type epoxy resin accounts for 5% of urethane-epoxide resin polymer system quality percentage composition when feeding intake; Polyethers N330: polyethers 2000=60: 40; γ-amine propyl-triethoxysilicane accounts for isocyanate groups mol ratio 10%; The total mol ratio of NCO and hydroxyl is 1.5: 1 in the polymeric system.
Embodiment 2: raw material drying to moisture content mass percent is below 0.01%; With molecular weight is that 4800 polyethers N330, molecular weight are that 2000 polyethers 2000 and bisphenol A type epoxy resin E-44 add in 60 ℃ of there-necked flasks; Add Toluene-2,4-diisocyanate after stirring half a hour; 4-vulcabond (TDI) reaction 6 hours obtains urethane-epoxy resin multicomponent polymeric; Be cooled to 30 ℃, add γ-amine propyl-triethoxysilicane stirring reaction after 3 hours, the ethyl acetate solution of the dibutyl tin laurate of adding 0.02% under the room temperature, the airtight preservation in back stirs.Bisphenol A type epoxy resin accounts for 10% of urethane-epoxide resin polymer system quality percentage composition when feeding intake; Polyethers N330: polyethers 2000=70: 30; γ-amine propyl-triethoxysilicane accounts for isocyanate groups mol ratio 40%; The total mol ratio of NCO and hydroxyl is 2.5: 1 in the polymeric system.
Embodiment 3: raw material drying to moisture content mass percent is below 0.01%; With molecular weight is that 4800 polyethers N330, molecular weight are that 2000 polyethers 2000 and bisphenol A type epoxy resin E-51 add in 60 ℃ of there-necked flasks; Add ditan-4 after stirring half a hour; Behind 4 '-vulcabond (MDI) temperature is risen to 70 ℃ of reactions 5 hours, obtain urethane-epoxy resin multicomponent polymeric; Be cooled to 60 ℃, add two [3-(triethoxysilicane) propyl group] amine stirring reactions after 1 hour, the ethyl acetate solution of the dibutyl tin laurate of adding 0.01% under the room temperature, the airtight preservation in back stirs.Bisphenol A type epoxy resin accounts for 15% of urethane-epoxide resin polymer system quality percentage composition when feeding intake; Polyethers N330: polyethers 2000=90: 10; γ-amine propyl-triethoxysilicane accounts for isocyanate groups mol ratio 10%; The total mol ratio of NCO and hydroxyl is 2: 1 in the polymeric system.
Embodiment 4: raw material drying to moisture content mass percent is below 0.01%; With molecular weight is that 4800 polyethers N330, molecular weight are that 2000 polyethers 2000 and bisphenol A type epoxy resin E-51 add in 60 ℃ of there-necked flasks; Add ditan-4 after stirring half a hour; Behind 4 '-vulcabond (MDI) temperature is risen to 70 ℃ of reactions 5 hours, obtain urethane-epoxy resin multicomponent polymeric; Be cooled to 60 ℃, add two [3-(triethoxysilicane) propyl group] amine stirring reactions after 1 hour, the ethyl acetate solution of the dibutyl tin laurate of adding 0.5% under the room temperature, the airtight preservation in back stirs.Bisphenol A type epoxy resin accounts for 15% of urethane-epoxide resin polymer system quality percentage composition when feeding intake; Polyethers N330: polyethers 2000=90: 10; γ-amine propyl-triethoxysilicane accounts for isocyanate groups mol ratio 10%; The total mol ratio of NCO and hydroxyl is 1.5: 1 in the polymeric system.
Embodiment 5: raw material drying to moisture content mass percent is below 0.01%; With molecular weight is that 4800 polyethers N330, molecular weight are that 2000 polyethers 2000 and bisphenol A type epoxy resin E-51 add in 60 ℃ of there-necked flasks; Add ditan-4 after stirring half a hour; Behind 4 '-vulcabond (MDI) temperature is risen to 70 ℃ of reactions 5 hours, obtain urethane-epoxy resin multicomponent polymeric; Be cooled to 60 ℃, add two [3-(triethoxysilicane) propyl group] amine stirring reactions after 1 hour, the ethyl acetate solution of the stannous octoate of adding 2% under the room temperature, the airtight preservation in back stirs.Bisphenol A type epoxy resin accounts for 15% of urethane-epoxide resin polymer system quality percentage composition when feeding intake; Polyethers N330: polyethers 2000=90: 10; γ-amine propyl-triethoxysilicane accounts for isocyanate groups mol ratio 40%; The total mol ratio of NCO and hydroxyl is 2.5: 1 in the polymeric system.
Embodiment 6: raw material drying to moisture content mass percent is below 0.01%; With molecular weight is that 4800 polyethers N330, molecular weight are that 2000 polyethers 2000 and bisphenol A type epoxy resin E-44 add in 60 ℃ of there-necked flasks; Add ditan-4 after stirring half a hour; Behind 4 '-vulcabond (MDI) temperature is risen to 70 ℃ of reactions 5 hours, obtain urethane-epoxy resin multicomponent polymeric; Be cooled to 50 ℃, add two [3-(triethoxysilicane) propyl group] amine stirring reactions after 2 hours, the ethyl acetate solution of the stannous octoate of adding 1% under the room temperature, the airtight preservation in back stirs.Bisphenol A type epoxy resin accounts for 20% of urethane-epoxide resin polymer system quality percentage composition when feeding intake; Polyethers N330: polyethers 2000=90: 10; γ-amine propyl-triethoxysilicane accounts for isocyanate groups mol ratio 30%; The total mol ratio of NCO and hydroxyl is 2.2: 1 in the polymeric system.
Table 1 is the Elongation test data of the polyurethane/epoxy resin polymerization objects system of the different polyethers 2000 that provides of the embodiment of the invention;
Table 1 contains the mechanics data of the silane macromolecular coupling agent of polyurethane/epoxy resin
Fig. 2 be the embodiment of the invention provide work as urethane: the epoxy resin mass ratio is 90: 10; The silicane macromolecular coupling agent system of different polyethers 2000 content is solidified the infrared spectrum of back sample, and polyethers 2000 in 1,2,3,4 among the figure: polyethers 300 mass ratioes are for being respectively 10: 90,20: 80,30: 70,40: 60.
Have excellent properties such as weather-proof, outstanding surface hydrophobicity, protection against the tide, good film-forming properties, electrical apparatus insulation, anti-ozone, difficult combustion, chemicalstability with the matrix material of the silicane macromolecular coupling agent preparation that contains the polyurethane/epoxy resin.The material that contains the silicane macromolecular coupling agent preparation of polyurethane/epoxy resin can be used in fields such as matrix material, automotive industry, fan clutch, electronic industry.The material that utilization contains the silicane macromolecular coupling agent preparation of polyurethane/epoxy resin will improve security, the safety of electronic product and increase the service life; The mechanical property of the silicane macromolecular coupling agent material that contains the polyurethane/epoxy resin of the present invention is all higher.
The preparation method of the silicane macromolecular coupling agent polymeric system that the embodiment of the invention provides; By urethane and two kinds of polymkeric substance of epoxy resin through molecular chain twine each other, chemical reaction; Form the compound system of excellent combination property; To have better consistency and some performances of matrix material are improved between polymkeric substance and inorganic reinforcement in order to make in the matrix material, adopt the amino-contained siloxanes that urethane-epoxy resin multicomponent polymeric system is carried out modification and prepare the silane macromolecular coupling agent; The amido of small molecules siloxanes can with the epoxy reaction in isocyanate groups in the urethane and the epoxy resin; Make it to become the macromolecular coupling agent that contains the interpenetrating polymer networks structure; This specific molecule structure and composition make it compile organic polymer and the coupling agent function is an one; Change the flexibility that polyurethane content is regulated macromolecular coupling agent,, after handling inorganic reinforcement, add in the polymeric matrix with it through changing the intensity that epoxy resin content is regulated macromolecular coupling agent; Can make polymer composites form reasonable interface, reach the purpose that improves matrix material overall synthetic performance; The preparation method of this silicane macromolecular coupling agent polymeric system, simple and practical, have stronger popularization and using value.
More than be merely preferred embodiment of the present invention,, all any modifications of within spirit of the present invention and principle, being done, be equal to and replace and improvement etc., all should be included within protection scope of the present invention not in order to restriction the present invention.
Claims (9)
1. the preparation method of a silicane macromolecular coupling agent polymeric system is characterized in that, this preparation method may further comprise the steps:
Step 1 with two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin raw material drying, is below 0.01% to the moisture content mass percent;
Step 2; Exsiccant two functionality or three-functionality-degree polyethers, bisphenol A type epoxy resin and vulcabond are added reaction kettle; React 3～6 hours generation urethane-epoxy resin multicomponent polymeric systems under the 60-80 ℃ of condition, bisphenol A epoxide resin accounts for the 5%-20% of urethane-epoxy resin multicomponent polymeric system quality percentage composition;
Step 3 adds γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine, under 30-60 ℃ of condition, reacts 1～3 hour, makes the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin;
Step 4 adds catalyzer in the silicane macromolecular coupling agent system of polyurethane/epoxy resin, stirs and airtight preservation.
2. preparation method as claimed in claim 1 is characterized in that, the prepared silicane macromolecular coupling agent of this preparation method is the silicane macromolecular coupling agent that contains the polyurethane/epoxy resin.
3. preparation method as claimed in claim 1 is characterized in that, in step 2, the mol ratio of contained total hydroxy is 1.5～2.5/1 in contained NCO of vulcabond and polyethers, the epoxy resin.
4. preparation method as claimed in claim 1 is characterized in that, in step 3, γ-amine propyl-triethoxysilicane or two [3-(triethoxysilicane) propyl group] amine account for 10%～40% of NCO mass contg.
5. preparation method as claimed in claim 3 is characterized in that the vulcabond that in step 2, is adopted is a ditan-4,4 '-vulcabond or tolylene diisocyanate.
6. preparation method as claimed in claim 1 is characterized in that, the bisphenol A type epoxy resin that in step 1, adopts is bisphenol A type epoxy resin E-44 or E-51.
7. preparation method as claimed in claim 1 is characterized in that, the polyethers that in step 1, adopts is polyethers N330 or polyethers 2000.
8. preparation method as claimed in claim 1 is characterized in that, the catalyzer that in step 4, adopts is dibutyl tin laurate, stannous octoate, quality be contain the polyurethane/epoxy resin silicane macromolecular coupling agent system 0.01%～2%.
9. preparation method as claimed in claim 1; It is characterized in that; The silicane macromolecular coupling agent that contains the polyurethane/epoxy resin that this preparation method is prepared is applied in preparation matrix material, damping material, Reinforced Rubber, tackiness agent, automotive industry with in material, medical macromolecular materials and the low temperature material.
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| CN103342795A (en) * | 2013-06-09 | 2013-10-09 | 合肥宏光研磨科技有限公司 | Preparation method for polyurethane polishing material by using network interpenetration |
| CN103819498A (en) * | 2014-01-27 | 2014-05-28 | 合肥工业大学 | Closed isocyanate coupling agent and application thereof |
| CN107151307A (en) * | 2017-04-24 | 2017-09-12 | 苏州金枪新材料股份有限公司 | A kind of organic silicon modified polyurethane sealant |
| CN111039136A (en) * | 2019-12-30 | 2020-04-21 | 浙江万立汽配有限公司 | Anti-aging escalator roller |
| CN112175159A (en) * | 2020-10-26 | 2021-01-05 | 衡阳拓创聚合新材料有限公司 | Silicon-modified elastic epoxy resin and preparation method thereof |
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| CN102417595A (en) * | 2011-11-20 | 2012-04-18 | 浙江精业生化有限公司 | Preparation method of polyurethane modified organic silica gel |
| CN102504524A (en) * | 2012-01-06 | 2012-06-20 | 常州大学 | Polysiloxane modified polyurethane-epoxy resin polymer material, preparation method thereof and use thereof |
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| CN102408866A (en) * | 2011-10-31 | 2012-04-11 | 东莞市普赛达密封粘胶有限公司 | Preparation method of water-swellable single-component polyurethane sealant |
| CN102417595A (en) * | 2011-11-20 | 2012-04-18 | 浙江精业生化有限公司 | Preparation method of polyurethane modified organic silica gel |
| CN102504524A (en) * | 2012-01-06 | 2012-06-20 | 常州大学 | Polysiloxane modified polyurethane-epoxy resin polymer material, preparation method thereof and use thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342795A (en) * | 2013-06-09 | 2013-10-09 | 合肥宏光研磨科技有限公司 | Preparation method for polyurethane polishing material by using network interpenetration |
| CN103819498A (en) * | 2014-01-27 | 2014-05-28 | 合肥工业大学 | Closed isocyanate coupling agent and application thereof |
| CN103819498B (en) * | 2014-01-27 | 2017-01-11 | 合肥工业大学 | Closed isocyanate coupling agent and application thereof |
| CN107151307A (en) * | 2017-04-24 | 2017-09-12 | 苏州金枪新材料股份有限公司 | A kind of organic silicon modified polyurethane sealant |
| CN111039136A (en) * | 2019-12-30 | 2020-04-21 | 浙江万立汽配有限公司 | Anti-aging escalator roller |
| CN112175159A (en) * | 2020-10-26 | 2021-01-05 | 衡阳拓创聚合新材料有限公司 | Silicon-modified elastic epoxy resin and preparation method thereof |
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Application publication date: 20121010 |