CN102617628A - Preparation method of bisamide-based silane coupling agent - Google Patents
Preparation method of bisamide-based silane coupling agent Download PDFInfo
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- CN102617628A CN102617628A CN2012100486152A CN201210048615A CN102617628A CN 102617628 A CN102617628 A CN 102617628A CN 2012100486152 A CN2012100486152 A CN 2012100486152A CN 201210048615 A CN201210048615 A CN 201210048615A CN 102617628 A CN102617628 A CN 102617628A
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- coupling agent
- silane coupling
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- aminosilane
- midbody
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Abstract
The invention provides a preparation method of a bisamide-based silane coupling agent, which comprises the steps of: firstly adding caprolactam to a reaction vessel containing a solvent, then dropwise adding acryloyl chloride to the reaction vessel for performing dropwise adding reaction, after reaction is finished, performing solid-liquid separation, then washing with alkali, separating to obtain an intermediate, and dropwise adding the intermediate to aminosilane for reaction to obtain an end product. According to the invention, the method is simple in process and convenient for operation; and the bisamide-based silane coupling agent prepared by the method is milder in coupling performance and stronger in stability, and has a significant application effect in the aspects of nylon 6, nylon66, and polyamide-based composite material and other materials.
Description
Technical field
The present invention relates to high score organic materials preparation field, be specifically related to a kind of preparation method of bisamide base silane coupling agent.
Background technology
Silane coupling agent is by trichlorosilane (HSiCl3) and has unsaturated olefin addition under the catalysis of platinum chloric acid of reactive group, gets through alcoholysis.It has KH550 at home, KH560, KH570, KH792, DL602, these several kinds of models of DL171.Silane coupling agent comes down to one type of silane with organo-functional group, in its molecule, has ability and the chemically combined reactive group of inanimate matter material (like glass, silica sand, metal etc.) and and the chemically combined reactive group of organic material (synthetic resins etc.) simultaneously.The present invention provides a kind of preparation method of new type double carboxamido-group silane coupling agent, and technology is simple, and is easy to operate.
Summary of the invention
The invention provides a kind of preparation method of bisamide base silane coupling agent, the inventive method technology is simple, and is easy to operate, the bisamide base silane coupling agent of the inventive method preparation, and the coupling performance is gentle, and has stronger stability.
The technical scheme that adopts for the present invention of realization above-mentioned purpose is following:
A kind of preparation method of bisamide base silane coupling agent is characterized in that may further comprise the steps:
(1) non-polar solvent is joined in the reaction vessel, the mass ratio of non-polar solvent and hexanolactam is (0.8-1.2): 1;
(2) the hexanolactam solid is joined in the reaction vessel that fills non-polar solvent, under 60-120 ℃ condition, drip acrylate chloride, be incubated 2-3 hour again after dripping, wherein, the mass ratio of hexanolactam and acrylate chloride is (220-230): 90;
(3) after insulation finishes, let it naturally cool to room temperature after, carry out solid-liquid separation again;
(4) with sodium hydroxide solution liquid phase is washed, obtain organic phase and inorganic mutually stratified two phase liquid, separate two phase liquid;
(5) organic phase is carried out underpressure distillation, obtain intermediate product;
(6) under the condition of room temperature, the midbody of step (5) gained is dropped in the aminosilane, after dropwising system is warming up to 28-32 ℃; Get the finished product bisamide base silane coupling agent; Wherein, the dropping ratio of midbody and aminosilane is (1-2): 1
Reaction formula is following:
The formation reaction formula of a, midbody
The reaction formula that b, final product generate is:
When (1) molar ratio of midbody and aminosilane was 1:1, the reaction formula that final product generates was:
When (2) ratio of midbody and aminosilane was 2:1, the reaction formula that final product generates was:
Wherein,
R1 represents alkyl
R2, R3 represent alkyl or alkoxyl group.
The preparation method of described bisamide base silane coupling agent is characterized in that: the described non-polar solvent of step (1) is selected from a kind of in hexanaphthene, normal hexane, benzene, sherwood oil, the chloroform.
The preparation method of described bisamide base silane coupling agent is characterized in that: the described concentration of sodium hydroxide solution of step (4) is 5%.
The preparation method of described bisamide base silane coupling agent; It is characterized in that: the described aminosilane of step (6) is selected from aminopropyl trimethoxysilane, aminopropyl methyl dimethoxysilane, aminopropyl triethoxysilane; Y-aminopropyl methyldiethoxysilane; The aminoethyl aminopropyl trimethoxysilane, 3-aminoethyl aminopropyl triethoxysilane, one or more in N-aminoethyl-3-aminopropyl methyl dimethoxysilane.
Beneficial effect of the present invention:
The inventive method technology is simple, and is easy to operate, the bisamide base silane coupling agent of preparation; The coupling performance is gentle, and has stronger stability, can be applied to the glass surface treatment; To the good applicability ability is arranged in the glass fiber enhanced nylon field; For the lagging material aspect, certain prospect is arranged, particularly aviation field of heat insulating materials simultaneously.
Embodiment
Embodiment 1
Under nonpolar solvent condition, add hexanolactam solid 226g, under 80 ℃ condition, drip the acrylate chloride of 90g; Dropwised back insulation 2 hours, and carried out solid-liquid separation after the cooling, extracting liq also adopts 5% sodium hydroxide solution to wash; Separate two phase liquid; Organic phase is carried out underpressure distillation, collect intermediate product, productive rate 75%.
Under the condition of room temperature, be the condition of 1:1 according to the ratio of midbody and aminopropyl trimethoxysilane, midbody is dropped in the aminosilane, be warming up to 30 ℃ after finishing, 290 gram the finished product.
Embodiment 2
Under nonpolar solvent condition, add hexanolactam solid 225g, under 100 ℃ condition, drip the acrylate chloride of 90g; Dropwised back insulation 3 hours, and carried out solid-liquid separation after the cooling, extracting liq also adopts 5% sodium hydroxide solution to wash; Separate two phase liquid; Organic phase is carried out underpressure distillation, collect intermediate product, productive rate 80%.
Under the condition of room temperature, be the condition of 2:1 according to the ratio of midbody and aminosilane, midbody is dropped in the aminoethyl aminopropyl trimethoxysilane, be warming up to 30 ℃ after finishing, 221 gram the finished product.
Experimental data
This coupling agent structure contains hexanolactam base and the dual functional group of carboxamido-group, aspect the cohesive force of resin, significant effect is arranged, and particularly the effect for the processing aspect of nylon 6, nylon 66 and polyamide-based matrix material is remarkable.Is example with coupling agent to the performance of glass fiber reinforced nylon 6/wollastonite, and data see the following form:
| Project | Use the aminopropyl trimethoxysilane coupling agent | Use bisamide base silane coupling agent |
| Shock strength/(KJ.m -2) | 14.5 | 16.8 |
| Tensile strength/MPa | 160.5 | 185.6 |
| Compressive strength/MPa | 222.1 | 236.3 |
Claims (4)
1. the preparation method of a bisamide base silane coupling agent is characterized in that may further comprise the steps:
(1) non-polar solvent is joined in the reaction vessel, the mass ratio of non-polar solvent and hexanolactam is (0.8-1.2): 1;
(2) the hexanolactam solid is joined in the reaction vessel that fills non-polar solvent, under 60-120 ℃ condition, drip acrylate chloride, be incubated 2-3 hour again after dripping, wherein, the mass ratio of hexanolactam and acrylate chloride is (220-230): 90;
(3) after insulation finishes, let it naturally cool to room temperature after, carry out solid-liquid separation again;
(4) with sodium hydroxide solution liquid phase is washed, obtain organic phase and inorganic mutually stratified two phase liquid, separate two phase liquid;
(5) organic phase is carried out underpressure distillation, obtain intermediate product;
(6) under the condition of room temperature, the midbody of step (5) gained is dropped in the aminosilane, after dropwising system is warming up to 28-32 ℃; Get the finished product bisamide base silane coupling agent; Wherein, the dropping ratio of midbody and aminosilane is (1-2): 1
Reaction formula is following:
The formation reaction formula of a, midbody
，
The reaction formula that b, final product generate is:
When (1) molar ratio of midbody and aminosilane was 1:1, the reaction formula that final product generates was:
When (2) ratio of midbody and aminosilane was 2:1, the reaction formula that final product generates was:
Wherein,
R1 represents alkyl
R2, R3 represent alkyl or alkoxyl group.
2. the preparation method of bisamide base silane coupling agent according to claim 1 is characterized in that: the described non-polar solvent of step (1) is selected from a kind of in hexanaphthene, normal hexane, benzene, sherwood oil, the chloroform.
3. the preparation method of bisamide base silane coupling agent according to claim 1 is characterized in that: the described concentration of sodium hydroxide solution of step (4) is 5%.
4. the preparation method of bisamide base silane coupling agent according to claim 1; It is characterized in that: the described aminosilane of step (6) is selected from aminopropyl trimethoxysilane, aminopropyl methyl dimethoxysilane, aminopropyl triethoxysilane; Y-aminopropyl methyldiethoxysilane; The aminoethyl aminopropyl trimethoxysilane, 3-aminoethyl aminopropyl triethoxysilane, one or more in N-aminoethyl-3-aminopropyl methyl dimethoxysilane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210048615.2A CN102617628B (en) | 2012-02-29 | 2012-02-29 | Preparation method of bisamide-based silane coupling agent |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210048615.2A CN102617628B (en) | 2012-02-29 | 2012-02-29 | Preparation method of bisamide-based silane coupling agent |
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| CN102617628A true CN102617628A (en) | 2012-08-01 |
| CN102617628B CN102617628B (en) | 2015-06-10 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07179745A (en) * | 1993-12-24 | 1995-07-18 | Mitsubishi Gas Chem Co Inc | Flame-retardant resin composition |
| EP0699745A2 (en) * | 1994-08-31 | 1996-03-06 | The Procter & Gamble Company | Automatic dishwashing compositions comprising quaternary ammonium compounds bleach activators and quaternary ammonium |
| CN1718409A (en) * | 2004-07-29 | 2006-01-11 | 南京理工大学 | Preparation method of nylon composite gradient pipe |
| CN1796459A (en) * | 2004-12-28 | 2006-07-05 | 上海杰事杰新材料股份有限公司 | Method for preparing nylon in lightweight |
| EP2236288A2 (en) * | 2009-04-01 | 2010-10-06 | Xerox Corporation | Imaging member |
-
2012
- 2012-02-29 CN CN201210048615.2A patent/CN102617628B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07179745A (en) * | 1993-12-24 | 1995-07-18 | Mitsubishi Gas Chem Co Inc | Flame-retardant resin composition |
| EP0699745A2 (en) * | 1994-08-31 | 1996-03-06 | The Procter & Gamble Company | Automatic dishwashing compositions comprising quaternary ammonium compounds bleach activators and quaternary ammonium |
| CN1718409A (en) * | 2004-07-29 | 2006-01-11 | 南京理工大学 | Preparation method of nylon composite gradient pipe |
| CN1796459A (en) * | 2004-12-28 | 2006-07-05 | 上海杰事杰新材料股份有限公司 | Method for preparing nylon in lightweight |
| EP2236288A2 (en) * | 2009-04-01 | 2010-10-06 | Xerox Corporation | Imaging member |
Non-Patent Citations (3)
| Title |
|---|
| BERND ROBERTZ等,: "Synthesis of cyclo(amide-ester)s by ring-expansion of N-(acyl)-lactams", 《MACROMOL. CHEM. PHYS.》 * |
| 胡乃昌，: "硅橡胶粘接用双酰胺基硅烷偶联剂的合成研究", 《化学工程师》 * |
| 黄虹文等,: "原位聚合La2O3/MC尼龙复合材料的制备与性能", 《塑料》 * |
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| CN102617628B (en) | 2015-06-10 |
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Address after: 238251 Anhui Ma'anshan county and Wujiang fine chemical base Patentee after: Anhui silicone silicone new material Co., Ltd. Address before: 238251 Anhui Ma'anshan county and Wujiang fine chemical base Patentee before: GBXF Silicones Co., Ltd. |