CN103865065B - A kind of preparation method of MT resin - Google Patents
A kind of preparation method of MT resin Download PDFInfo
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- CN103865065B CN103865065B CN201410114528.1A CN201410114528A CN103865065B CN 103865065 B CN103865065 B CN 103865065B CN 201410114528 A CN201410114528 A CN 201410114528A CN 103865065 B CN103865065 B CN 103865065B
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- trifluoromethanesulfonic acid
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
A kind of preparation method of MT resin; comprise the following steps: the first step: in reaction vessel, add dry toluene, dehydrated alcohol and alkoxy silane; then under the conditions of 50～70 DEG C; and under nitrogen protection; with fluorine-containing methanesulfonic acid or fluorine-containing mesylate as catalyst, in reaction vessel, drip acetic acid make alkoxy silane react with described acetic acid；Wherein, alkoxy silane and acetic acid mol ratio between the two are 1 0.95～1.2；Second step: the solvent in elimination reaction container；3rd step: under the conditions of 80～100 DEG C, adds tetramethyl two hydrogen-based disiloxane in reaction vessel, i.e. obtains MT resin after dripping acetic acid, fully reaction the most again in reaction vessel；Wherein, tetramethyl two hydrogen-based disiloxane and alkoxy silane mol ratio between the two are 1 0.45～0.55；Acetic acid and alkoxy silane mol ratio between the two are 1 0.9～1.2.The method that the present invention prepares MT resin is simple, and the MT resin structure prepared is stable.
Description
Technical field
The present invention relates to the preparation method of a kind of MT resin, belong to technical field of adhesive preparation.
Background technology
In industrial quarters, the bonding agent being applicable on transparent optical element has the materials such as epoxy adhesive, rubber adhesive, acrylic resin modified binding agent, polyurethane adhesive.
The shortcoming of epoxy resin is that anti-yellowing property is poor, and meanwhile, the performance of its cracking resistance and impact is also weak.The shortcoming of rubber adhesive is poor storage stability.Polyurethane adhesive shortcoming is that temperature tolerance is poor, facile hydrolysis under high temperature.The touch screen OCA glue being widely used at present is the highest due to cost and price, and technique is loaded down with trivial details, has bigger limitation.Although Silica hydrogel has preferable transparency, but cannot be directly used as the binding agent of transparent optical element because its viscosity is low, need the crosslink density adding auxiliary agent to promote Silica hydrogel.
Summary of the invention
It is an object of the present invention to provide the preparation method of a kind of MT resin.
For reaching above-mentioned purpose, the technical solution used in the present invention is: the preparation method of a kind of MT resin, comprises the following steps:
The first step: add dry toluene, dehydrated alcohol and alkoxy silane in reaction vessel; then under the conditions of 50～70 DEG C; and under nitrogen protection; with fluorine-containing methanesulfonic acid or fluorine-containing mesylate as catalyst, in described reaction vessel, drip acetic acid make described alkoxy silane react with described acetic acid；Wherein, described alkoxy silane and acetic acid mol ratio between the two are 1 0.95～1.2；
Second step: remove the solvent in described reaction vessel；
3rd step: under the conditions of 80～100 DEG C, adds tetramethyl two hydrogen-based disiloxane in described reaction vessel, i.e. obtains MT resin after dripping acetic acid, fully reaction the most again in described reaction vessel；Wherein, described tetramethyl two hydrogen-based disiloxane and alkoxy silane mol ratio between the two are 1 0.45～0.55；Described acetic acid and alkoxy silane mol ratio between the two are 1 0.9～1.2.
Preferably technical scheme is: described alkoxy silane is selected from MTMS, MTES, methyl tripropoxy silane, dimethyldimethoxysil,ne, dimethyldiethoxysilane, ethyl trimethoxy silane, n-pro-pyl trimethoxy silane, trimethoxysilane, isobutyl triethoxy silane, n-octytriethoxysilane, n-octyl trimethoxy silane, trimethylmethoxysilane, trimethylethoxysilane, trimethylmethoxysilane.
Preferably technical scheme is: described fluorine-containing methanesulfonic acid is trifluoromethanesulfonic acid.
Preferably technical scheme is: described fluorine-containing mesylate is cuprous selected from copper trifluoromethanesulfcomposite, silver trifluoromethanesulfonate, trifluoromethanesulfonic acid magnesium, trifluoromethanesulfonic acid zinc, trifluoromethanesulfonic acid, trifluoromethanesulfonic acid cerium, trifluoromethanesulfonic acid samarium, trifluoromethanesulfonic acid europium, Ytterbiumtriflate, trifluoromethanesulfonic acid praseodymium, trifluoromethanesulfonic acid lanthanum, trifluoromethanesulfonic acid neodymium, trifluoromethanesulfonic acid erbium, trifluoromethanesulfonic acid dysprosium.
Preferably technical scheme is: after the 3rd EOS, and in described reaction vessel, the acetic anhydride of the material amount such as addition and tetramethyl two hydrogen-based disiloxane is to absorb the water generated in the 3rd step.
Owing to technique scheme is used, the present invention compared with prior art has following advantages and an effect:
1, the present invention prepares the method for MT resin simply, and the MT resin structure prepared is stable.
2, the present invention is in full laminating Silica hydrogel caking agent series, can improve the hot strength of Silica hydrogel system.
Accompanying drawing explanation
Accompanying drawing 1 is the infrared spectrum of MT silicones.
Accompanying drawing 2 is the nucleus magnetic hydrogen spectrum of MT silicones.
Accompanying drawing 3 is the nuclear-magnetism silicon spectrum of MT silicones.
Detailed description of the invention
Below in conjunction with the accompanying drawings and embodiment the invention will be further described:
Embodiment one: the preparation method of a kind of MT resin
The preparation method of a kind of MT resin, comprises the following steps:
The first step: add dry toluene, dehydrated alcohol and MTMS in reaction vessel; then under the conditions of 50～70 DEG C; and under nitrogen protection; specifically refer to reaction vessel be placed under nitrogen atmosphere; temperature conditions and nitrogen protective condition are indispensable; then in reaction vessel, it is initially charged trifluoromethanesulfonic acid as catalyst, in described reaction vessel, then drips acetic acid make described MTMS and described acetic acid carry out reacting prepared intermediate product；Wherein, described MTMS and acetic acid mol ratio between the two are 11.
Second step: remove the solvent in described reaction vessel；The method of desolvation specifically heating evaporation.
3rd step: under the conditions of 80～100 DEG C, tetramethyl two hydrogen-based disiloxane is added in described reaction vessel, acetic acid is dripped the most again in described reaction vessel, the intermediate product reaction that acetic acid and the first step prepare generates silicone hydroxyl, and silicone hydroxyl is prepared MT resin by tetramethyl two hydrogen-based disiloxane end-blocking；The most cooled, wash, distill after i.e. obtain pure MT organic siliconresin.Wherein, described tetramethyl two hydrogen-based disiloxane and MTMS mol ratio between the two are 1 0.5；Described acetic acid and MTMS mol ratio between the two are 11.
The simplification planar structure formula of the MT resin prepared is as follows, is not drawn into part for repeating silica structure unit.
The simplification of the MT resin prepared is three-dimensional as follows:
。
The MT resin spectrogram prepared is as shown in accompanying drawing 1～3.
In Fig. 1,2965cm-1It is the absworption peak of C-H, 1268 cm-1It is Si-CH3Absworption peak, 1018 cm-1It it is the absworption peak of Si-O-Si.
Embodiment two: the preparation method of a kind of MT resin
The preparation method of a kind of MT resin, comprises the following steps:
The first step: add dry toluene, dehydrated alcohol and dimethyldiethoxysilane in reaction vessel; then under the conditions of 50～70 DEG C; and under nitrogen protection; specifically refer to reaction vessel be placed under nitrogen atmosphere; temperature conditions and nitrogen protective condition are indispensable; then in reaction vessel, it is initially charged trifluoromethanesulfonic acid zinc as catalyst, in described reaction vessel, then drips acetic acid make described dimethyldiethoxysilane and described acetic acid carry out reacting prepared intermediate product；Wherein, described dimethyldiethoxysilane and acetic acid mol ratio between the two are 1 1.1.
Second step: remove the solvent in described reaction vessel；The method of desolvation specifically heating evaporation.
3rd step: under the conditions of 80～100 DEG C, tetramethyl two hydrogen-based disiloxane is added in described reaction vessel, acetic acid is dripped the most again in described reaction vessel, the intermediate product reaction that acetic acid and the first step prepare generates silicone hydroxyl, and silicone hydroxyl is prepared MT resin by tetramethyl two hydrogen-based disiloxane end-blocking.In described reaction vessel, the acetic anhydride of the material amount such as addition and tetramethyl two hydrogen-based disiloxane is to absorb the water generated in the 3rd step.The most cooled, wash, distill after i.e. obtain pure MT organic siliconresin.Wherein, described tetramethyl two hydrogen-based disiloxane and dimethyldiethoxysilane mol ratio between the two are 1 0.52；Described acetic acid and dimethyldiethoxysilane mol ratio between the two are 1 1.05.
Embodiment three: the preparation method of a kind of MT resin
The preparation method of a kind of MT resin, comprises the following steps:
The first step: adding dry toluene, dehydrated alcohol, n-pro-pyl trimethoxy silane and the mixture of methyl tripropoxy silane, n-pro-pyl trimethoxy silane and methyl tripropoxy silane mass ratio between the two in reaction vessel is 11.Then under the conditions of 50～70 DEG C; and under nitrogen protection; specifically refer to reaction vessel be placed under nitrogen atmosphere; temperature conditions and nitrogen protective condition are indispensable; then in reaction vessel, it is initially charged trifluoromethanesulfonic acid praseodymium as catalyst, in described reaction vessel, then drips acetic acid make the mixture of described n-pro-pyl trimethoxy silane and methyl tripropoxy silane and described acetic acid carry out reacting prepared intermediate product；Wherein, the mixture of described n-pro-pyl trimethoxy silane and methyl tripropoxy silane and acetic acid mol ratio between the two are 1 1.1.
Second step: remove the solvent in described reaction vessel；The method of desolvation specifically heating evaporation.
3rd step: under the conditions of 80～100 DEG C, tetramethyl two hydrogen-based disiloxane is added in described reaction vessel, acetic acid is dripped the most again in described reaction vessel, the intermediate product reaction that acetic acid and the first step prepare generates silicone hydroxyl, and silicone hydroxyl is prepared MT resin by tetramethyl two hydrogen-based disiloxane end-blocking.In described reaction vessel, the acetic anhydride of the material amount such as addition and tetramethyl two hydrogen-based disiloxane is to absorb the water generated in the 3rd step.The most cooled, wash, distill after i.e. obtain pure MT organic siliconresin.Wherein, the mixture of described tetramethyl two hydrogen-based disiloxane and n-pro-pyl trimethoxy silane and methyl tripropoxy silane mol ratio between the two is 1 0.5；The mixture of described acetic acid and n-pro-pyl trimethoxy silane and methyl tripropoxy silane mol ratio between the two is 11.
Embodiment four: the preparation method of a kind of MT resin
The preparation method of a kind of MT resin, comprises the following steps:
The first step: add dry toluene in reaction vessel, dehydrated alcohol and trimethylethoxysilane, then under the conditions of 50～70 DEG C, and under nitrogen protection, specifically refer to reaction vessel be placed under nitrogen atmosphere, temperature conditions and nitrogen protective condition are indispensable, then in reaction vessel, Ytterbiumtriflate and copper trifluoromethanesulfcomposite it are initially charged as catalyst (Ytterbiumtriflate and copper trifluoromethanesulfcomposite mass ratio between the two is 1 1), then dripping acetic acid in described reaction vessel makes described trimethylethoxysilane and described acetic acid carry out reacting prepared intermediate product；Wherein, described trimethylethoxysilane and acetic acid mol ratio between the two are 1 1.1.
Second step: remove the solvent in described reaction vessel；The method of desolvation specifically heating evaporation.
3rd step: under the conditions of 80～100 DEG C, tetramethyl two hydrogen-based disiloxane is added in described reaction vessel, acetic acid is dripped the most again in described reaction vessel, the intermediate product reaction that acetic acid and the first step prepare generates silicone hydroxyl, and silicone hydroxyl is prepared MT resin by tetramethyl two hydrogen-based disiloxane end-blocking.In described reaction vessel, the acetic anhydride of the material amount such as addition and tetramethyl two hydrogen-based disiloxane is to absorb the water generated in the 3rd step.The most cooled, wash, distill after i.e. obtain pure MT organic siliconresin.Wherein, described tetramethyl two hydrogen-based disiloxane and trimethylethoxysilane mol ratio between the two are 1 0.55；Described acetic acid and trimethylethoxysilane mol ratio between the two are 11.
Above-described embodiment only for technology design and the feature of the present invention are described, its object is to allow person skilled in the art will appreciate that present disclosure and to implement according to this, can not limit the scope of the invention with this.All equivalence changes made according to spirit of the invention or modification, all should contain within protection scope of the present invention.
Claims (5)
1. the preparation method of a MT resin, it is characterised in that: comprise the following steps:
The first step: add dry toluene, dehydrated alcohol and alkoxy silane in reaction vessel; then under the conditions of 50～70 DEG C; and under nitrogen protection; with fluorine-containing methanesulfonic acid or fluorine-containing mesylate as catalyst, in described reaction vessel, drip acetic acid make described alkoxy silane react with described acetic acid；Wherein, described alkoxy silane and acetic acid mol ratio between the two are 1:0.95～1.2；
Second step: remove the solvent in described reaction vessel；
3rd step: under the conditions of 80～100 DEG C, adds tetramethyl two hydrogen-based disiloxane in described reaction vessel, i.e. obtains MT resin after dripping acetic acid, fully reaction the most again in described reaction vessel；Wherein, described tetramethyl two hydrogen-based disiloxane and alkoxy silane mol ratio between the two are 1:0.45～0.55；Described acetic acid and alkoxy silane mol ratio between the two are 1:0.9～1.2.
The preparation method of MT resin the most according to claim 1, it is characterized in that: described alkoxy silane is selected from MTMS, MTES, methyl tripropoxy silane, ethyl trimethoxy silane, n-pro-pyl trimethoxy silane, trimethoxysilane, isobutyl triethoxy silane, n-octytriethoxysilane, n-octyl trimethoxy silane, trimethylmethoxysilane, trimethylethoxysilane, trimethylmethoxysilane.
The preparation method of MT resin the most according to claim 1, it is characterised in that: described fluorine-containing methanesulfonic acid is trifluoromethanesulfonic acid.
The preparation method of MT resin the most according to claim 1, it is characterised in that: described fluorine-containing mesylate is cuprous selected from copper trifluoromethanesulfcomposite, silver trifluoromethanesulfonate, trifluoromethanesulfonic acid magnesium, trifluoromethanesulfonic acid zinc, trifluoromethanesulfonic acid, trifluoromethanesulfonic acid cerium, trifluoromethanesulfonic acid samarium, trifluoromethanesulfonic acid europium, Ytterbiumtriflate, trifluoromethanesulfonic acid praseodymium, trifluoromethanesulfonic acid lanthanum, trifluoromethanesulfonic acid neodymium, trifluoromethanesulfonic acid erbium, trifluoromethanesulfonic acid dysprosium.
The preparation method of MT resin the most according to claim 1, it is characterised in that: after the 3rd EOS, in described reaction vessel, the acetic anhydride of the material amount such as addition and tetramethyl two hydrogen-based disiloxane is to absorb the water generated in the 3rd step.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410114528.1A CN103865065B (en) | 2014-03-26 | 2014-03-26 | A kind of preparation method of MT resin |
| PCT/CN2014/001070 WO2015143592A1 (en) | 2014-03-26 | 2014-12-01 | Method for preparing mt resin |
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| CN201410114528.1A CN103865065B (en) | 2014-03-26 | 2014-03-26 | A kind of preparation method of MT resin |
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| CN103865065A CN103865065A (en) | 2014-06-18 |
| CN103865065B true CN103865065B (en) | 2017-01-04 |
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| CN103865065B (en) * | 2014-03-26 | 2017-01-04 | 苏州桐力光电股份有限公司 | A kind of preparation method of MT resin |
| CN112708137B (en) * | 2020-08-24 | 2022-04-01 | 惠州市永卓科技有限公司 | Preparation method of low-hydroxyl-content MDT silicone oil with end capped by dimethylvinylsiloxy group |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004073626A2 (en) * | 2003-02-14 | 2004-09-02 | Revlon Consumer Products Corporation | Cosmetic compositions containing siloxane polymers |
| CN102875810A (en) * | 2012-09-29 | 2013-01-16 | 中昊晨光化工研究院有限公司 | Phenyl-containing MT type resin and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS5966422A (en) * | 1982-10-08 | 1984-04-14 | Japan Synthetic Rubber Co Ltd | Preparation of silicone resin |
| US20060211836A1 (en) * | 2005-03-15 | 2006-09-21 | General Electric Company | Disproportionation of hydridosiloxanes and crosslinked polysiloxane network derived therefrom |
| DE102007055485A1 (en) * | 2007-11-21 | 2009-06-04 | Evonik Goldschmidt Gmbh | Process for the preparation of branched SiH-functional polysiloxanes and their use for the preparation of SiC- and SiOC-linked, branched organomodified polysiloxanes |
| CN101875724B (en) * | 2009-04-30 | 2012-08-08 | 东莞市贝特利新材料有限公司 | Preparation method of phenyl silicone resin |
| CN101891893B (en) * | 2010-07-23 | 2012-01-04 | 深圳市安品有机硅材料有限公司 | Preparation method of phenyl-based hydrogen-based silicone resin for encapsulating LED |
| CN103242531B (en) * | 2013-05-09 | 2015-04-22 | 成都硅宝新材料有限公司 | Preparation method of phenyl hydrogen-containing MT silicone resin |
| CN103865065B (en) * | 2014-03-26 | 2017-01-04 | 苏州桐力光电股份有限公司 | A kind of preparation method of MT resin |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004073626A2 (en) * | 2003-02-14 | 2004-09-02 | Revlon Consumer Products Corporation | Cosmetic compositions containing siloxane polymers |
| CN102875810A (en) * | 2012-09-29 | 2013-01-16 | 中昊晨光化工研究院有限公司 | Phenyl-containing MT type resin and preparation method thereof |
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| CN103865065A (en) | 2014-06-18 |
| WO2015143592A1 (en) | 2015-10-01 |
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Inventor after: Shi Dong Inventor before: Shi Dong Inventor before: Ji Jinhong |
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Address after: Suzhou City, Jiangsu province 215000 Industrial Park Weiting kuangtang West JINDA Road No. 8 Applicant after: SUZHOU TONGLI PHOTOELECTRIC CO., LTD. Address before: 215000 No. 166 benevolence Road, Suzhou, Jiangsu Applicant before: Suzhou Tong Li photoelectric technology Services Co., Ltd |
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