CN112029464A - Cross dehydrogenation coupling reaction-based low-modulus MS sealant and preparation method thereof - Google Patents
Cross dehydrogenation coupling reaction-based low-modulus MS sealant and preparation method thereof Download PDFInfo
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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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
- C08K2003/265—Calcium, strontium or barium carbonate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Abstract
The invention relates to a low-modulus MS sealant based on cross dehydrogenation coupling reaction and a preparation method thereof. The adhesive is prepared by mixing 45-60 parts by weight of silane-terminated polyether, 20-35 parts by weight of inorganic filler, 2-8 parts by weight of thixotropic agent, 5-15 parts by weight of plasticizer and 0.5-2 parts by weight of crosslinking type silane coupling agent. Multifunctional hydroxyl-terminated polyoxypropylene ether, bilateral hydrogen silane and unilateral hydrogen silane are adopted to successfully prepare silane-terminated polyether with the number average molecular weight of 5000-50000 g/mol through cross dehydrogenation coupling reaction. The synthetic route has mild reaction conditions and simple and convenient process. Based on the silane terminated polyether, the silane terminated polyether is compounded with inorganic filler and a crosslinking silane coupling agent, so that the MS sealant with low modulus and excellent bonding performance can be obtained. Free isocyanate groups and urethane bonds in molecular chains of the product are crosslinked through Si-O-Si bonds, and the advantages of polyurethane sealant and silicone adhesive can be integrated.
Description
Technical Field
The invention relates to a low-modulus MS sealant based on cross dehydrogenation coupling reaction and a preparation method thereof, belonging to the technical field of sealants.
Background
The low-modulus silane-terminated polyether sealant (MS sealant) is an ideal material for filling gaps of prefabricated parts of outer walls of prefabricated parts of prefabricated buildings, and can effectively deal with the displacement of the prefabricated parts and simultaneously keep good adhesion. Polyurethane sealants and silicone sealants can theoretically achieve low modulus, but the former have the problems of poor weather resistance and easy failure of long-term adhesion, and the latter have the problem of substrate contamination due to silicone oil exudation.
The MS sealing glue and the core technology are silane end capping polyether, and the general synthetic route is that high molecular weight polyether and allyl chloride are subjected to Williams' reaction in the presence of alkali catalyst to obtain allyl end capping polyether, and then Pt or chloroplatinic acid is used as catalyst to react with dimethoxy methyl silane to obtain silane end capping polyether. The unique technical route and the commercial products are respectively developed by the Japanese Brillouin chemistry, Switzerland Wake and the U.S. Dow chemistry, and the production and the use of the upstream raw material silane-terminated polyether are limited under the patent protection and pricing rights, so the market share of the MS sealant in China is very low. The new synthetic route is opened to bypass the limitation of foreign patents, so that the technical barrier can be really broken and the market monopoly can be broken.
Disclosure of Invention
In order to solve the problems, the invention provides a low-modulus MS sealant based on a cross dehydrogenation coupling reaction and a preparation method thereof.
The invention relates to a cross dehydrogenation coupling reaction-based low-modulus MS sealant and a preparation method thereof, wherein the cross dehydrogenation coupling reaction-based low-modulus MS sealant comprises the following components in parts by weight:
45-60 parts of silane terminated polyether;
20-35 parts of an inorganic filler;
2-8 parts of thixotropic agent
5-15 parts of plasticizer
0.5-2 parts of a crosslinking silane coupling agent.
Preferably, the silane-terminated polyether is prepared by cross dehydrogenation coupling reaction of polyether polyol, bilateral hydrogen silane and unilateral hydrogen silane, and the number average molecular weight is 5000-50000 g/mol.
Preferably, in the preparation of the silane-terminated polyether, the polyether polyol has a functionality of 2.0-3.0, a number average molecular weight of 1000-8000 g/mol, and a main chain structure of polyoxypropylene ether, and is one or a mixture of more of the polyether polyol and the polyoxyalkylene ether.
Preferably, in the preparation of the silane-terminated polyether, the double-sided hydrogen-terminated silane is one or more of 1,1,3, 3-tetramethyldisiloxane (CAS number: 3277-26-7), 1,3,3,5, 5-hexamethyltrisiloxane (CAS number: 1189-93-1), 1, 4-bis (dimethylsilyl) benzene (CAS number: 2488-01-9), 1,4, 4-tetramethyl-1, 4-disilabutane (CAS number: 20152-11-8).
Preferably, in the preparation of the silane-terminated polyether, the one-side hydrogen-terminated silane is one or a mixture of two of trimethoxy silane (CAS number: 1189-93-1) and triethoxy silane (CAS number: 998-30-1).
Preferably, the inorganic filler is one or a mixture of heavy calcium carbonate, light calcium carbonate, nano calcium carbonate, carbon black and titanium dioxide.
Preferably, the thixotropic agent is fumed silica.
Preferably, the plasticizer is one or more of dioctyl phthalate (DOP), dioctyl nonyl phthalate (DINP), diisodecyl phthalate (DIDP).
Preferably, the crosslinking type silane coupling agent is one or two mixtures of methyl triethoxysilane and methyl triethoxysilane.
The preparation method of the silane-terminated polyether comprises the following steps: adding polyether polyol into a reactor according to a set formula, heating to 120 ℃, controlling the vacuum degree to be not more than-0.095 MPa, and dewatering for 1-2 hours under the condition; and cooling to 25-70 ℃, adding hydrogen silane and a catalyst at two sides for chain extension, stirring for 12-48 hours under the protection of nitrogen, adding hydrogen silane at one side, stirring for 12-48 hours under the protection of nitrogen, obtaining silane-terminated polyether, and sealing and storing for later use.
Preferably, in the preparation of the silane-terminated polyether, the average functionality of one or more polyether polyols is controlled to be 2.0-2.2, the molar charge ratio of polyether polyol/bilateral terminal hydrosilane/unilateral terminal hydrosilane is controlled to be 1: 0.5-0.8: 0.2-0.5, and the molar ratio of lateral terminal hydrosilane/catalyst is controlled to be 1.0-10.0 x 103。
Preferably, the silane-terminated polyether is catalyzed in its preparationThe agent is platinum (0) -1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane (Karstedt catalyst, CAS number: 81032-58-8), Karstedt catalyst solution (CAS number: 68478-92-2), and tris (dibenzylideneacetone) dipalladium (Pd)2(dba)3CAS number: 16941), 10% Pd/C catalyst, triphenylphosphine rhodium chloride (PdCl)2(PPh3)3CAS number: 14694-95-2), bis (triphenylphosphine) palladium dichloride (RhCl (PPh)3)3CAS number: 13965-03-2).
The low-modulus MS sealant based on the cross dehydrogenation coupling reaction and the preparation method thereof are as follows: controlling the temperature in the reactor to be 25-30 ℃, adding silane terminated polyether, inorganic filler, thixotropic agent, plasticizer and crosslinking type silane coupling agent according to a set formula, stirring and mixing for 0.5-1 hour, metering and discharging, and sealing and packaging to obtain the product.
The cross dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof have the beneficial effects that: (1) the multifunctional hydroxyl-terminated polyoxypropylene ether, the bilateral hydrogen silane and the unilateral hydrogen silane are subjected to cross dehydrogenation coupling reaction to prepare the high molecular weight silane terminated polyether, the reaction conditions are mild, the product does not contain free isocyanate groups and urethane bonds, the weather resistance and the thermal stability are equivalent to those of the traditional silane terminated polyether, the controllability of the high molecular weight silane terminated polyether is good, and the low modulus can be realized; (2) the silane-terminated polyether is matched with a crosslinking silane coupling agent, so that the rapid curing under the moisture condition can be realized.
Detailed description of the preferred embodiment
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to specific examples.
The following raw materials are used in the experiments in the examples and comparative examples of the present invention, but the present invention is not limited to the following raw materials, and the following raw materials are only specific examples to further specifically illustrate the effects of the long-acting low-odor low-VOC one-component polyurethane sealant described in the present application:
polyether polyol: functionality 2.0, number average molecular weight 2000g/mol, PPG2000, east China Lanzhou Dongdong.
Double-sided hydrogen-terminated silane and single-sided hydrogen-terminated silane: 1,1,3, 3-tetramethyldisiloxane, trimethoxysilane, Shanghai Miruil.
Crosslinking type silane coupling agent: methyltriethoxysilane, shanghai meier.
Catalyst: karstedt catalyst solution, shanghai michelin.
Inorganic filler: NAK-2108 nano calcium carbonate and NC-60A heavy calcium carbonate are mixed according to the mass ratio of 1:6, and the Xufeng powder is obtained.
Thixotropic agent: fumed silica, R972, degussa.
Plasticizer: nanjing Rongji chemical DOP.
The comprehensive performance is tested according to the method specified in GB/T14683-2017 for MS-I-R-20LM, and the technical index refers to the standard specification.
Surface drying time: the test is carried out by referring to the method A specified in GB/T13477.5-2002, and the surface drying time is less than or equal to 24 hours specified in GB/T14683-2017.
Sag: the test is carried out by referring to the method specified in GB/T13477.6-2002, and GB/T14683-2017 specifies that the vertical direction is less than or equal to 3mm and the horizontal direction is not deformed.
Extrudability: the test is carried out by referring to the method specified in GB/T13477.3-2017, and GB/T14683-2017 specifies that the extrusion property is more than or equal to 150 mL/min.
Permanent deformation at definite elongation: the test is carried out by referring to the method A specified in GB/T13477.17-2017, the elongation percentage is 100 percent, the stretching rate is 5mm/min, and the permanent set of the fixed elongation is more than 50 percent specified in GB/T14683-2017.
Tensile modulus: the test is carried out by referring to the method A specified in GB/T13477.8-2017, and the tensile modulus at 23 ℃ is less than or equal to 0.4MPa and the tensile modulus at 20 ℃ is less than or equal to 0.6MPa according to GB/T14683-2017.
Setting and stretching cohesiveness: the test was carried out with reference to the method specified in GB/T13477.10-2017, GB/T14683-2017 specifies that the stretch-setting adhesion should be non-destructive.
And (3) the fixed-extension cohesiveness after soaking: the test was carried out with reference to the method specified in GB/T13477.11-2017, GB/T14683-2017 specifies that the stretch-setting adhesion should be non-destructive.
And (3) the fixed-stretching cohesiveness after cold drawing and hot pressing: the test was carried out with reference to the method specified in GB/T13477.13-2017, GB/T14683-2017 specifies that the stretch-setting adhesion should be non-destructive.
Mass loss rate: the test is carried out by referring to a GB/T13477.19-2017 method, and the GB/T14683-2017 stipulates that the mass loss rate is less than or equal to 5 percent.
The examples and comparative examples were prepared as follows:
the invention sets the embodiments 1-8 and the comparative examples 1-3, the experimental steps and the method are the same, a series of single-component transparent high-bonding-strength silane-modified polyurethane corner-combining adhesives are obtained, and the preparation method comprises the following steps:
step (1): controlling the average functionality of one or more polyether polyols to be 2.0-2.2, controlling the molar charge ratio of the polyether polyol PPG 2000/bilateral terminal hydrosilane/unilateral terminal hydrosilane to be 1:0.8:0.2, and controlling the molar ratio of the lateral terminal hydrosilane/catalyst to be 5.0 x 103Firstly, putting polyether glycol PPG2000 into a reactor, heating to 120 ℃, controlling the vacuum degree to be not more than-0.095 MPa, dewatering for 1-2 hours under the condition, cooling to 50 ℃, putting bilateral end hydrosilane, dripping Karstedt catalyst solution, stirring for 24 hours under the protection of nitrogen, putting unilateral end hydrosilane, stirring for 24 hours under the protection of nitrogen, obtaining silane-terminated polyether, and sealing and storing for later use. Step (2): controlling the temperature in the reactor to be 25-30 ℃, adding the mixture of silane-terminated polyether, NAK-2108 nano calcium carbonate and NC-60A heavy calcium carbonate, fumed silica thixotropic agent, plasticizer DOP and crosslinking type silane coupling agent methyltrimethoxysilane according to a set formula, stirring and mixing for 0.5-1 hour, metering and discharging, sealing and packaging to obtain the product
The cross dehydrogenation coupling reaction-based low-modulus MS sealant of examples 1 to 8 and comparative examples 1 to 3, and the preparation method, formula and performance thereof are shown in Table 1
The properties of examples 1 to 8 are shown in Table 1
Comparative examples 1 to 6 Properties are shown in Table 2
Table 1 examples 1 to 8 all had excellent workability (extrudability, sagging property, open time), mechanical strength and adhesion. In comparative examples 1 to 6, the workability, tensile modulus and adhesiveness were not met. The synthesized high molecular weight silane terminated polyether can reach the indexes of low modulus and permanent set by reasonably matching the inorganic filler and the thixotropic agent, and can synergistically improve the adhesion and the surface drying time by matching the crosslinking silane coupling agent.
The above description is only an example of the present invention, and is not intended to limit the present invention. The invention is susceptible to various modifications and alternative forms. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (13)
1. The cross dehydrogenation coupling reaction-based low-modulus MS sealant is characterized by being prepared by mixing 45-60 parts by weight of silane-terminated polyether, 20-35 parts by weight of inorganic filler, 2-8 parts by weight of thixotropic agent, 5-15 parts by weight of plasticizer and 0.5-2 parts by weight of crosslinking type silane coupling agent.
2. The cross-dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof as claimed in claim 1, wherein the silane terminated polyether is prepared by cross-dehydrogenation coupling reaction of polyether polyol, bilateral hydrogen silane and unilateral hydrogen silane, and the number average molecular weight is 5000-50000 g/mol.
3. The cross-dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof as claimed in claims 1-2, wherein in the preparation of the silane-terminated polyether, the polyether polyol has a functionality of 2.0-3.0, a number average molecular weight of 1000-8000 g/mol, and a main chain structure of polyoxypropylene ether, and is one or more of a mixture.
4. The low-modulus MS sealant based on the cross-dehydrogenation coupling reaction and the preparation method thereof as claimed in claims 1 to 3, wherein the silane terminated polyether is prepared by one or more of 1,1,3, 3-tetramethyldisiloxane (CAS number: 3277-26-7), 1,3,3,5, 5-hexamethyltrisiloxane (CAS number: 1189-93-1), 1, 4-bis (dimethylsilyl) benzene (CAS number: 2488-01-9), 1,4, 4-tetramethyl-1, 4-disilabutane (CAS number: 20152-11-8).
5. The low-modulus MS sealant based on the cross dehydrogenation coupling reaction and the preparation method thereof as claimed in claims 1-4, wherein in the preparation of the silane terminated polyether, the unilateral hydrogen-terminated silane is one or a mixture of trimethoxy silane (CAS number 1189-93-1) and triethoxy silane (CAS number 998-30-1).
6. The low-modulus MS sealant based on the cross dehydrogenation-coupling reaction and the preparation method thereof as claimed in claims 1-5, wherein the inorganic filler is one or more of heavy calcium carbonate, light calcium carbonate, nano calcium carbonate, carbon black and titanium dioxide.
7. The cross-dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof as claimed in claims 1 to 6, wherein the thixotropic agent is fumed silica.
8. The cross-dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof according to claims 1 to 7, wherein the plasticizer is one or more of dioctyl phthalate (DOP), dioctyl nonyl phthalate (DINP) and diisodecyl phthalate (DIDP).
9. The low-modulus MS sealant based on the cross-dehydrogenation coupling reaction and the preparation method thereof as claimed in claims 1 to 8, wherein the cross-linking type silane coupling agent is one or two of methyl triethoxysilane and methyl triethoxysilane.
10. The cross dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof as claimed in claims 1-9, wherein the preparation method of the silane terminated polyether is as follows: adding polyether polyol into a reactor according to a set formula, heating to 120 ℃, controlling the vacuum degree to be not more than-0.095 MPa, and dewatering for 1-2 hours under the condition; and cooling to 25-70 ℃, adding hydrogen silane and a catalyst at two sides for chain extension, stirring for 12-48 hours under the protection of nitrogen, adding hydrogen silane at one side, stirring for 12-48 hours under the protection of nitrogen, obtaining silane-terminated polyether, and sealing and storing for later use.
11. The cross-dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof as claimed in claims 1 to 10, wherein in the preparation of the silane-terminated polyether, the average functionality of one or more of the polyether polyols is controlled to be 2.0 to 2.2, the molar charge ratio of the polyether polyol/the bilateral hydrosilane/the unilateral hydrosilane is controlled to be 1:0.4 to 0.8:0.2 to 0.6, and the molar ratio of the lateral hydrosilane/the catalyst is 1.0 to 10.0 x 103。
12. The cross-dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof as claimed in claims 1-11, wherein in the preparation of the silane-terminated polyether, the catalyst is platinum (0) -1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane (Karstedt catalyst, CAS number: 81032-58-8) or Karstedt catalyst solution (Karstedt catalyst solution)CAS number: 68478-92-2), tris (dibenzylideneacetone) dipalladium (Pd)2(dba)3CAS number: 16941), 10% Pd/C catalyst, triphenylphosphine rhodium chloride (PdCl)2(PPh3)3CAS number: 14694-95-2), bis (triphenylphosphine) palladium dichloride (RhCl (PPh)3)3CAS number: 13965-03-2).
13. The cross dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof according to claims 1 to 11, wherein the cross dehydrogenation coupling reaction-based low-modulus MS sealant and the preparation method thereof are prepared by the following steps: controlling the temperature in the reactor to be 25-30 ℃, adding silane terminated polyether, inorganic filler, thixotropic agent, plasticizer and crosslinking type silane coupling agent according to a set formula, stirring and mixing for 0.5-1 hour, metering and discharging, and sealing and packaging to obtain the product.
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| CN105153984A (en) * | 2015-10-10 | 2015-12-16 | 诸暨市科凌新材料科技有限公司 | Heat-conducting silane-terminated polyether sealant and preparation method thereof |
| CN105219336A (en) * | 2015-09-09 | 2016-01-06 | 浙江汇杰有机硅股份有限公司 | A kind of environmentally friendly seal gum and preparation method thereof |
| WO2017102944A1 (en) * | 2015-12-15 | 2017-06-22 | Dsm Ip Assets B.V. | Process for the production of biaryl compounds |
| CN108329478A (en) * | 2018-02-02 | 2018-07-27 | 无锡龙驰氟硅新材料有限公司 | A kind of Silante terminated MS resins and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105219336A (en) * | 2015-09-09 | 2016-01-06 | 浙江汇杰有机硅股份有限公司 | A kind of environmentally friendly seal gum and preparation method thereof |
| CN105153984A (en) * | 2015-10-10 | 2015-12-16 | 诸暨市科凌新材料科技有限公司 | Heat-conducting silane-terminated polyether sealant and preparation method thereof |
| WO2017102944A1 (en) * | 2015-12-15 | 2017-06-22 | Dsm Ip Assets B.V. | Process for the production of biaryl compounds |
| CN108329478A (en) * | 2018-02-02 | 2018-07-27 | 无锡龙驰氟硅新材料有限公司 | A kind of Silante terminated MS resins and preparation method thereof |
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