CN108239284B - Addition type liquid silicone rubber tackifier and preparation method thereof - Google Patents
Addition type liquid silicone rubber tackifier and preparation method thereof Download PDFInfo
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- CN108239284B CN108239284B CN201611227643.5A CN201611227643A CN108239284B CN 108239284 B CN108239284 B CN 108239284B CN 201611227643 A CN201611227643 A CN 201611227643A CN 108239284 B CN108239284 B CN 108239284B
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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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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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
- C08G77/08—Preparatory processes characterised by the catalysts used
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- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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Abstract
The invention relates to a multipurpose organic silicon tackifier and a preparation method thereof, wherein the organic silicon tackifier is prepared by taking dimethyl dialkoxy silane, diphenyl dialkoxy silane, methyl vinyl dialkoxy silane, gamma-glycidyl ether oxygen propyl trialkoxy silane and gamma- (methacryloyloxy) propyl trialkoxy silane as raw materials through hydrolysis reaction and equilibrium reaction. The tackifier prepared by the invention has good transparency; the addition of a small amount of the silicon rubber can improve the adhesive property of the silicon rubber to base materials such as metal and organic synthetic materials; the tackifier with the refractive index ranging from 1.43 to 1.56 can be prepared by adopting the preparation method, and the tackifier can be suitable for liquid silicone rubber with different refractive index requirements without influencing the light transmittance; the process operation is simple and easy.
Description
Technical Field
The invention relates to an addition type liquid silicone rubber tackifier and a preparation method thereof, belonging to the technical field of high polymer materials.
Background
As is well known, addition type liquid silicone rubber has excellent application performance after vulcanization, and has been widely applied in various fields, such as potting compounds for electronic components, potting compounds for L ED lamps and the like.
At present, measures for improving the adhesive property of addition type silicon rubber are as follows: (1) treating the surface of the substrate with a silane coupling agent such as KH550, KH560 as a primer; however, when a silane coupling agent such as gamma-aminopropyltriethoxysilane (i.e., KH 550) and gamma-glycidoxypropyltrimethoxysilane (i.e., KH 560) is used alone as a primer, the silicone rubber has a certain adhesion to a substrate, but the effect is limited, and many adverse effects are caused, such as: the appearance of the product is changed due to the hydrolysis of the self alkoxy; producing an unpleasant odor; affecting the light transmittance of the product, etc. (2) The adhesive is obtained by reacting low-viscosity hydroxyl silicone oil with a silane coupling agent. However, due to the limitation of molecular structure, the bonding effect is not ideal, and due to the limitation of low refractive index, the low refractive index silicon rubber is only matched with the full methyl addition type silicon rubber with the refractive index of about 1.41 at room temperature, and is not suitable for addition type silicon rubber containing higher phenyl.
Disclosure of Invention
In order to solve the defects of unsatisfactory bonding effect and single purpose of the existing addition type liquid silicone rubber tackifier, the invention provides a preparation method of a multipurpose organic silicon tackifier.
The technical scheme adopted by the invention is as follows:
an addition-type liquid silicon rubber tackifier is prepared from dimethyl dialkoxy silane, diphenyl dialkoxy silane, methyl vinyl dialkoxy silane, gamma-glycidyl ether oxygen propyl trialkoxy silane and gamma- (methacryloyloxy) propyl trialkoxy silane through hydrolysis reaction and balancing reaction.
The structure of the obtained addition type liquid silicone rubber tackifier is as follows:
wherein M, n, a, b and c are integers of 0-100, and M represents an end-capping.
The reaction molar ratio of the dimethyl dialkoxyl silane, the diphenyl dialkoxyl silane, the methyl vinyl dialkoxyl silane, the gamma-glycidyl ether oxygen propyl trialkoxy silane to the gamma- (methacryloyloxy) propyl trialkoxy silane is as follows: 1: (0-1.5): (0.01-0.1): (0.02-0.5): (0.02-0.5). Preferably, the molar ratio of the raw materials is 1: (0-0.6): (0.03-0.08): (0.02-0.05): (0.02-0.03).
The hydrolysis reaction is specifically operated as follows: adding the raw materials and hydrochloric acid into an organic solvent, heating to a reflux temperature, dropwise adding water, and maintaining a reflux reaction for 3-4 hours.
The organic solvent is selected from methanol or ethanol; the dosage of the organic solvent is 2-5 times of the molar dosage of the dimethyldialkoxysilane.
The dosage of the hydrochloric acid is 0.005-0.01 time of the molar dosage of the dimethyldialkoxysilane. In order to ensure the hydrolysis effect, concentrated hydrochloric acid is preferably used in the invention.
The using amount of the water is 1.5-2.7 times of the molar using amount of the dimethyl dialkoxy silane.
The reflux temperature is 70-85 ℃.
The equilibrium reaction refers to the reaction of the hydrolysate and the blocking agent under the action of the alkaline catalyst.
The alkaline catalyst is selected from tetramethylammonium hydroxide.
The end-capping agent is divinyltetramethyldisiloxane or hexamethyldisiloxane. The using amount of the end-capping agent is 0.5-1 time of the molar using amount of the dimethyl dialkoxy silane.
Before the equilibrium reaction, the system after the hydrolysis reaction is finished is cooled to room temperature, neutralized, and removed alcohol and excessive water. The reagent adopted for neutralization is sodium carbonate or sodium bicarbonate. The temperature for removing the alcohols and the water is not more than 110 ℃.
The invention also comprises post-treatment, in particular to heating the system after the equilibrium reaction to break enzyme and removing low-boiling-point substances under the conditions of high temperature and reduced pressure to obtain a final product. The high temperature is 150-160 ℃, and the reduced pressure is-0.08-0.09 MPa.
The reaction mechanism of the invention is as follows:
wherein m, n, a, b and c are integers from 0 to 100, R is methyl, and MM is represented as an end-capping agent.
The invention has the beneficial effects that: the tackifier prepared by the invention has good transparency; the addition of a small amount of the silicon rubber can improve the adhesive property of the silicon rubber to base materials such as metal and organic synthetic materials; the tackifier with the refractive index ranging from 1.43 to 1.56 can be prepared by adopting the preparation method, and the tackifier can be suitable for liquid silicone rubber with different refractive index requirements without influencing the light transmittance; the process operation is simple and easy.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
120g of dimethyldimethoxysilane (1mol), 122g of diphenyldimethoxysilane (0.5mol), 10g of methylvinyldimethoxysilane (0.075mol), 10g of gamma-glycidoxypropyltrimethoxysilane (silane coupling agent KH-560, 0.042mol), 5g of gamma- (methacryloyloxy) propyltrimethoxysilane (KH-570, 0.02mol) were added to a 1L three-necked flask containing 200g of methanol, stirred, 0.1g of concentrated hydrochloric acid was added dropwise, the temperature was raised to 70 ℃, 60g of water was added dropwise, the reflux temperature was maintained for 3 hours, the temperature was lowered to room temperature, 2g of sodium bicarbonate was added for neutralization and washing to neutrality, water and methanol were removed at-0.09 MPa and 100 ℃, 1g of hexamethyldisiloxane (0.006mol), 0.01g of tetramethylammonium hydroxide (0.0001mol) was added thereto, and after reaction at 100 ℃ for 3 hours, the enzyme was broken to give a refractive index of 1.53 and a viscosity of 30mm2(s) colorless transparent liquid.
Example 2
120g of dimethyldimethoxysilane (1mol), 30g of diphenyldimethoxysilane (0.12mol), 5g of methylvinyldimethoxysilane (0.038mol), 7g of gamma-glycidoxypropyltrimethoxysilane (silane coupling agent KH-560, 0.029mol), 5g of gamma- (methacryloyloxy) propyltrimethoxysilane (KH-570, 0.02mol) were added to a 1L three-necked flask containing 200g of methanol, stirred, 0.1g of concentrated hydrochloric acid was added dropwise, the temperature was raised to 70 ℃, 55g of water was added dropwise, the reflux temperature was maintained for 3 hours, the temperature was lowered to room temperature, 2g of sodium bicarbonate was added for neutralization and washing with water to neutrality, water and methanol were removed at-0.09 MPa and 100 ℃, 1g of hexamethyldisiloxane, 0.01g of tetramethylammonium hydroxide were added thereto at room temperature, the enzyme was broken after reaction at 100 ℃ for 3 hours, and the refractive index was 1.45 and the viscosity was 15mm, and the enzyme was obtained2(s) colorless transparent liquid.
Example 3
148g of dimethyldiethoxysilane (1mol), 75g of diphenyldiethoxysilane (0.275mol), 12g of methylvinyldiethoxysilane (0.075mol), 14g of gamma-glycidyloxypropyltriethoxysilane (silane coupling agent KH-561, 0.05mol), 6g of gamma- (methacryloyloxy) propyltriethoxysilane (0.02mol) were added to a solution containing 150g of ethyldiethoxysilane (1mol)Stirring in a 1L three-necked alcohol bottle, dropwise adding 0.1g of concentrated hydrochloric acid, heating to 80 ℃, dropwise adding 70g of water, maintaining the reflux temperature for 4 hours, cooling to room temperature, adding 2g of sodium bicarbonate for neutralization, washing with water to be neutral, removing water and alcohol at 100 ℃ of-0.09 MPa, cooling to room temperature, adding 1.1g of divinyl tetramethyl disiloxane and 0.01g of tetramethyl ammonium hydroxide, reacting at 100 ℃ for 3 hours, and then breaking the enzyme to obtain the product with the refractive index of 1.47 and the viscosity of 25mm2(s) colorless transparent liquid.
Example 4
148g of dimethyldiethoxysilane (1mol), 148g of diphenyldiethoxysilane (0.544mol), 12g of methylvinyldiethoxysilane (0.075mol), 14g of gamma-glycidoxypropyltriethoxysilane (0.05mol), 6g of gamma- (methacryloyloxy) propyltriethoxysilane (0.02mol) were charged into a 1L three-necked flask containing 150g of ethanol, stirred, 0.1g of concentrated hydrochloric acid was added dropwise, the temperature was raised to 80 ℃ C., 70g of water was added dropwise, the reflux temperature was maintained for 4 hours, the temperature was lowered to room temperature, 2g of sodium bicarbonate was added for neutralization and washing with water to neutrality at-0.09 MPa, 100 ℃ C. to remove water and alcohol, 1g of hexamethyldisiloxane and 0.01g of tetramethylammonium hydroxide were added thereto at room temperature, the enzyme was destroyed after reaction for 3 hours at 100 ℃ C., and the refractive index was 1.51 and the viscosity was 27mm were obtained2(s) colorless transparent liquid.
Example 5
148g of dimethyldiethoxysilane (1mol), 12g of methylvinyldiethoxysilane (0.075mol), 14g of gamma-glycidoxypropyltriethoxysilane (0.05mol) and 6g of gamma- (methacryloyloxy) propyltriethoxysilane (0.02mol) were charged into a 1L three-necked flask containing 150g of ethanol, stirred, 0.1g of concentrated hydrochloric acid was added dropwise, the temperature was raised to 80 ℃ C., 70g of water was added dropwise, the reflux temperature was maintained for 4 hours, the temperature was lowered to room temperature, 2g of sodium bicarbonate was added for neutralization and washing with water to neutrality, water and alcohol were removed at-0.09 MPa and 100 ℃ C., 0.5g of tetramethyldisiloxane and 0.01g of tetramethylammonium hydroxide were added to the cooled to room temperature, and after 3 hours of reaction at 100 ℃ C, the enzyme was broken to obtain a divinyl solution having a refractive index of 1.42 and a viscosity of 10mm2(s) colorless transparent liquid.
Example 6
150g of dimethyldimethoxysilane (1.25mol), 170g of diphenyldimethoxysilane (0.696mol),7g of methylvinyldiethoxysilane (0.044mol), 11g of gamma-glycidoxypropyltrimethoxysilane (0.046mol) and 8g of gamma- (methacryloyloxy) propyltrimethoxysilane (0.032mol) were added to a 1L three-necked flask containing 150g of ethanol, stirred, 0.1g of concentrated hydrochloric acid was added dropwise, the temperature was raised to 80 ℃, 70g of water was added dropwise, the reflux temperature was maintained for 4 hours, the mixture was cooled to room temperature, 2g of sodium bicarbonate was added for neutralization and washed with water to neutrality, water and alcohol were removed at-0.09 MPa and 100 ℃, 0.5g of divinyltetramethyldisiloxane and 0.01g of tetramethylammonium hydroxide were added thereto, the reaction was carried out at 100 ℃ for 3 hours, and the enzyme was broken to obtain a compound having a refractive index of 1.42 and a viscosity of 10mm2(s) colorless transparent liquid.
Effect verification
An addition liquid silicone rubber base compound was prepared from 100g of a vinyl silicone oil having a viscosity of 2000 mPas, 40g of a methyl silicone resin having a vinyl content of 6%, 10g of a hydrogen-containing silicone oil having a hydrogen content of 4%, 0.2g of an inhibitor, and 0.1g of a platinum catalyst. Taking 7 equal parts of base rubber, wherein each part is 20g, the parts are respectively marked as example 1, example 2, example 3, example 4, example 5 and example 6, and blank samples, respectively adding 0.5g of the tackifier prepared in each example according to the corresponding relation, adding no other reagent into the blank samples, uniformly stirring the blank samples, smearing the blank samples on a PC board substrate, vulcanizing the blank samples at 120 ℃ for 2 hours, and then testing the adhesive strength of the blank samples by using a material testing machine. The test results are shown in table 1:
TABLE 1
The table shows that the addition of a proper amount of the tackifier synthesized by the invention can obviously improve the shear strength of the additive liquid silicone rubber, and the tackifier synthesized by the invention can greatly improve the bonding performance of the organosilicon sealant.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (4)
1. An addition type liquid silicon rubber tackifier is characterized in that dimethyl dialkoxy silane, diphenyl dialkoxy silane, methyl vinyl dialkoxy silane, gamma-glycidyl ether oxygen propyl trialkoxy silane and gamma- (methacryloyloxy) propyl trialkoxy silane are used as raw materials and are obtained through hydrolysis reaction and equilibrium reaction;
wherein the reaction molar ratio of the dimethyldialkoxysilane, the diphenyldialkoxysilane, the methylvinyldialkoxysilane, the gamma-glycidoxypropyltrialkoxysilane is as follows: 1: (0-1.5): (0.01-0.1): (0.02-0.5): (0.02-0.5);
the hydrolysis reaction is specifically operated as follows: adding raw materials and hydrochloric acid into an organic solvent, heating to a reflux temperature, dropwise adding water, and maintaining a reflux reaction for 3-4 hours;
the equilibrium reaction refers to the reaction of the hydrolysate and the end capping agent under the action of the alkaline catalyst;
wherein the basic catalyst is selected from tetramethylammonium hydroxide;
the end-capping agent is divinyl tetramethyl disiloxane or hexamethyl disiloxane;
the using amount of the end-capping agent is 0.5-1 time of the molar using amount of the dimethyl dialkoxy silane;
before the equilibrium reaction is carried out, the system after the hydrolysis reaction is finished is cooled to room temperature, neutralized, and removed alcohols and excessive water;
heating the system after the equilibrium reaction to break enzyme, and removing low-boiling-point substances under the conditions of high temperature and reduced pressure to obtain a final product; wherein the high temperature is 150-160 ℃, and the reduced pressure is-0.08-0.09 MPa.
2. The addition liquid silicone rubber tackifier of claim 1, wherein the organic solvent is selected from methanol or ethanol;
the dosage of the organic solvent is 2-5 times of the molar dosage of the dimethyldialkoxysilane;
the dosage of the hydrochloric acid is 0.005-0.01 time of the molar dosage of the dimethyldialkoxysilane.
3. The addition type liquid silicone rubber tackifier according to claim 1, wherein the reflux temperature is 70-85 ℃.
4. The addition liquid silicone rubber tackifier of claim 1, wherein the agent used for neutralization is sodium carbonate or sodium bicarbonate;
the temperature for removing the alcohols and the water is not more than 110 ℃.
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| CN109054022A (en) * | 2018-07-19 | 2018-12-21 | 深圳市希顺有机硅科技有限公司 | Low-temperature fast-curing additional organosilicon tackifier and preparation method thereof in one kind |
| CN108893092A (en) * | 2018-07-19 | 2018-11-27 | 深圳市希顺有机硅科技有限公司 | Low-temperature fast-curing additional organosilicon is bonded silicon rubber in one kind |
| CN109337074A (en) * | 2018-09-29 | 2019-02-15 | 烟台德邦先进硅材料有限公司 | A kind of synthetic method of LED packaging plastic bonding agent |
| CN109897182A (en) * | 2019-03-02 | 2019-06-18 | 江西省龙海化工有限公司 | A kind of aqueous macromolecular amount silane coupling agent and preparation method thereof |
| CN110982077B (en) * | 2019-12-03 | 2022-02-18 | 万华化学集团股份有限公司 | Modified tackifier, preparation method and application |
| CN115418192B (en) * | 2022-10-15 | 2023-06-23 | 江苏矽时代材料科技有限公司 | Addition type room-temperature-curing pouring sealant with high bonding strength and preparation method and application thereof |
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| CN103739848A (en) * | 2013-12-25 | 2014-04-23 | 北京化工大学 | Tackifier for addition type organosilicone packaging glue and preparation method thereof |
| CN104892942A (en) * | 2015-06-04 | 2015-09-09 | 成都拓利化工实业有限公司 | Tackifier for addition-type organic silicon rubber and preparation method thereof |
| CN105400446A (en) * | 2015-12-18 | 2016-03-16 | 东莞市贝特利新材料有限公司 | Tackifier for high-refractive index LED liquid casting glue and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103739848A (en) * | 2013-12-25 | 2014-04-23 | 北京化工大学 | Tackifier for addition type organosilicone packaging glue and preparation method thereof |
| CN104892942A (en) * | 2015-06-04 | 2015-09-09 | 成都拓利化工实业有限公司 | Tackifier for addition-type organic silicon rubber and preparation method thereof |
| CN105400446A (en) * | 2015-12-18 | 2016-03-16 | 东莞市贝特利新材料有限公司 | Tackifier for high-refractive index LED liquid casting glue and preparation method thereof |
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