CN114805712A - Silane modified SBR resin, sealant and preparation method thereof - Google Patents
Silane modified SBR resin, sealant and preparation method thereof Download PDFInfo
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- CN114805712A CN114805712A CN202210443133.0A CN202210443133A CN114805712A CN 114805712 A CN114805712 A CN 114805712A CN 202210443133 A CN202210443133 A CN 202210443133A CN 114805712 A CN114805712 A CN 114805712A
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- silane
- modified sbr
- sbr resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/02—Vinyl aromatic monomers and conjugated dienes
- C09J153/025—Vinyl aromatic monomers and conjugated dienes modified
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Sealing Material Composition (AREA)
Abstract
The invention belongs to the technical field of high polymer materials, and particularly relates to a silane modified SBR resin, and further discloses a silane modified SBR resin enhanced sealant, and further discloses a preparation method thereof. The silane modified SBR resin is a block copolymer polymerized by amino organosilicon terminated PS and PB based on an anionic polymerization system to obtain the needed silane modified SBR resin. The silane modified SBR resin enhanced sealant is based on the traditional polyether/polyurethane system sealant material, and can effectively improve the tensile strength of the sealant material, further improve the influence performance of the sealant material and expand the application of the sealant material in the high dynamic load application field by adding the silane end-capped modified SBR resin.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to a silane modified SBR resin, and further discloses a silane modified SBR resin enhanced sealant, and further discloses a preparation method thereof.
Background
The sealant is a material for filling gaps (cavities or joints), has the characteristics of deformation along with the shape of a sealing surface, difficulty in flowing and certain cohesiveness, can play a role in sealing, and has the functions of leakage prevention, water prevention, vibration prevention, sound insulation, heat insulation and the like. The sealant material has various types, and mainly comprises an organic silicon sealant and a polyurethane sealant material. Wherein, the organosilicon sealant material has the best adhesive property and aging resistance, but the mechanical properties such as tensile strength and shear strength are lower; the polyurethane sealant material has excellent mechanical properties, but has almost no cohesiveness to certain substrates such as glass and aluminum materials, and the application field is severely limited. Therefore, the organosilicon modified polyurethane sealant material has the advantages of excellent mechanical properties of polyurethane sealant, good adhesion and aging resistance of organosilicon sealant material, and the like, and becomes the first choice of sealant material.
At present, most of organosilicon modified polyurethane sealant materials widely applied in the market are silane modified polyether/polyurethane system materials, and the organosilicon modified polyurethane sealant materials are widely applied to sealing of doors, windows, bathrooms due to the advantages of good flexibility, no toxicity, environmental protection and the like. However, the tensile strength, the elongation at break and other properties of the material are not very outstanding, so that the material does not have product advantages when being applied to the application field of high dynamic load. Therefore, how to further improve the mechanical properties such as tensile strength and the like of the silane modified polyurethane sealant system material meets the requirements of the high dynamic load application field, and has positive significance for development and popularization of sealant materials.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to provide a silane modified SBR resin, wherein the silane modified SBR can effectively improve the tensile strength of a sealant material;
the second technical problem to be solved by the invention is to provide a silane modified SBR resin enhanced sealant, so as to solve the problem that the mechanical properties such as tensile strength and the like of a silane modified polyurethane sealant material in the prior art are not ideal;
the third technical problem to be solved by the invention is to provide the preparation methods of the silane modified SBR resin and the silane modified SBR resin reinforced sealant material.
In order to solve the technical problems, the preparation method of the silane modified SBR resin comprises the following steps:
(1) synthesis of blocking agent
Taking aminosilane and benzaldehyde as raw materials, reacting in an organic solvent system, collecting a crude product, and filtering and distilling under reduced pressure to obtain a blocking agent for later use;
(2) synthesis of silane modified SBR resin
Introducing measured PS and PB under a protective atmosphere, adding measured n-butyllithium to initiate a polymerization reaction, then adding the end capping agent obtained in the step (1) to perform end capping treatment, and discharging to obtain the product;
specifically, in the step (1), the aminosilane comprises silane KH-550.
Specifically, in the step (1), the molar ratio of the benzaldehyde to the aminosilane is 1.1: 1.0.
specifically, in the step (1), the reaction temperature is 40-60 ℃, and the reaction time is 3-5 h.
Specifically, in the step (1), the organic solvent includes toluene.
Specifically, in the step (2), the PS, PB, and n-butyllithium (based on Li) + Amount) and the capping agent in a molar ratio of 1: 3: 2: 2.
specifically, in the step (2), the temperature in the polymerization step is 40-60 ℃, and the temperature in the end capping step is 50-70 ℃.
The invention also discloses the silane modified SBR resin prepared by the method.
The invention also discloses application of the silane modified SBR resin in preparing a sealant material.
The invention also discloses a silane modified SBR resin enhanced sealant which comprises the following components in parts by weight:
10-90 parts by weight of silane modified SBR resin;
10-90 parts by weight of silane modified polyether/polyurethane resin;
5-80 parts of filler;
1-10 parts of antioxidant;
1-10 parts of rheological additive;
1-10 parts of a water removing agent;
1-10 parts by weight of a silane coupling agent;
0.1-2 parts of catalyst.
Specifically, the silane modified SBR resin reinforced sealant comprises the following components in parts by weight:
preferably, the molecular weight of the silane modified polyether/polyurethane resin is 10000-30000;
the filler comprises at least one of light calcium or heavy calcium;
the silane coupling agent comprises one or a mixture of more than two of 3-aminopropyl trimethoxy silane, N-beta- (aminoethyl) -gamma-aminopropyl trimethoxy silane, vinyl trimethoxy silane, gamma-aminopropyl triethoxy silane and gamma-glycidoxypropyl trimethoxy silane;
the catalyst comprises at least one of an organotin catalyst or an organobismuth catalyst.
The antioxidant, the rheological aid and the water removal agent are prepared from conventional preparations in the field.
Preferably, the molecular weight of the silane-modified SBR resin is 10000-30000.
The invention also discloses a method for preparing the silane modified SBR resin enhanced sealant, which comprises the steps of taking selected amounts of the silane modified SBR resin, the silane modified polyether/polyurethane, a filler, an antioxidant, a rheological aid, a water scavenger, a silane coupling agent and a catalyst, fully mixing uniformly and discharging in a low-humidity environment protection atmosphere.
The silane modified SBR resin is a segmented copolymer polymerized by PS and PB terminated by amino organosilicon based on an anionic polymerization system to obtain the needed silane modified SBR resin, can effectively improve the mechanical properties such as tensile strength and the like of a sealant, further improves the influence performance of a sealant material, and expands the application of the sealant material in the field of high dynamic load application.
The silane modified SBR resin enhanced sealant is based on the traditional polyether/polyurethane system sealant material, and can effectively improve the tensile strength of the sealant material, further improve the influence performance of the sealant material and expand the application of the sealant material in the high dynamic load application field by adding the silane end-capped modified SBR resin.
Detailed Description
In the following preparation examples of the present invention, the preparation method of the silane-modified SBR resin comprises the following steps:
(1) synthesis of blocking agent
Taking aminosilane and benzaldehyde as raw materials, reacting in an organic solvent system, collecting a crude product, and filtering and distilling under reduced pressure to obtain a blocking agent for later use;
(2) synthesis of silane-modified SBR resin
Introducing measured PS and PB under a protective atmosphere, adding measured n-butyllithium to initiate a polymerization reaction, then adding the end capping agent obtained in the step (1) to perform end capping treatment, and discharging to obtain the product;
preparation example 1
Taking toluene as a solvent, firstly dripping aminosilane KH-550 and then dripping benzaldehyde, and controlling the molar ratio of the benzaldehyde to the aminosilane to be 1.1: 1.0, controlling the reaction temperature to be 50 ℃, reacting for 4 hours, filtering and distilling the obtained crude product under reduced pressure to obtain the product, namely the end-capping reagent.
A1000 ml round-bottom flask was used, and metered amounts of PS and PB were introduced under argon protectionStirring at 1000r/min, injecting trace n-butyl lithium to kill impurities to light yellow, immediately injecting metered n-butyl lithium, placing into a 50 ℃ water bath to initiate polymerization, and injecting the end capping agent to control the PS, PB and n-butyl lithium (based on Li) + In terms of) and capping agent in a molar ratio of 1: 3: 2: 2, putting the mixture into a water bath kettle at the temperature of 60 ℃ for sealing and processing for 30min, discharging, sealing and storing to obtain the needed silane modified SBR resin.
Preparation example 2
Taking toluene as a solvent, firstly dripping aminosilane KH-550 and then dripping benzaldehyde, and controlling the molar ratio of the benzaldehyde to the aminosilane to be 1.1: 1.0, controlling the reaction temperature to be 40 ℃, reacting for 5 hours, filtering and distilling the obtained crude product under reduced pressure to obtain a product, namely the end-capping reagent.
Introducing a metered PS (PS), PB and n-butyllithium (based on Li) into a 1000ml round-bottom flask under the protection of argon, stirring at the rotating speed of 1000r/min, injecting a trace amount of n-butyllithium to kill impurities to be light yellow, and immediately injecting metered n-butyllithium + Amount) and the capping agent in a molar ratio of 1: 3: 2: and 2, then placing the mixture into a water bath kettle at 40 ℃ to initiate polymerization, then injecting and adding the end capping agent, placing the mixture into a water bath kettle at 50 ℃ to perform end capping treatment for 30min, and discharging, sealing and storing to obtain the needed silane modified SBR resin.
Preparation example 3
Taking toluene as a solvent, firstly dripping aminosilane KH-550 and then dripping benzaldehyde, and controlling the molar ratio of the benzaldehyde to the aminosilane to be 1.1: 1.0, controlling the reaction temperature to be 60 ℃, reacting for 3 hours, filtering and distilling the obtained crude product under reduced pressure to obtain the product, namely the end-capping reagent.
Introducing a metered PB (based on Li) into a 1000-ml round-bottom flask under the protection of argon, stirring at the rotating speed of 1000r/min, injecting a trace amount of n-butyl lithium to kill impurities to be light yellow, and immediately injecting metered n-butyl lithium to control the PS, PB and n-butyl lithium (based on Li) + Amount) and the capping agent in a molar ratio of 1: 3: 2: 2, then placing the mixture into a water bath kettle at 60 ℃ to initiate polymerization reaction, then injecting and adding the end capping agent, and placing the mixture into water at 70 DEG CAnd (3) carrying out end-capping treatment in a bath kettle for 30min, discharging, sealing and storing to obtain the needed silane modified SBR resin.
Examples 1 to 6
The raw materials and the mixture ratio of the silane modified enhanced sealant disclosed in the following examples 1-6 are detailed in the following table 1:
the silane-modified SBR resin is the modified SBR resin prepared in the preparation example 1;
MAX-350 resin is selected as the silane modified polyether/polyurethane;
the filler is light calcium (the grain diameter is less than 10 mu m);
the antioxidant is Irganox 245;
the rheological aid is Crayvallac SL;
the water removing agent is A-171;
the silane coupling agent is selected from KH 560;
the catalyst is SUL-11A organotin catalyst.
The preparation method of the silane modified enhanced sealant disclosed in the following embodiments 1-6 comprises the steps of taking selected amounts of the silane modified SBR resin, the silane modified polyether/polyurethane, the filler, the antioxidant, the rheological aid, the water removal agent, the silane coupling agent and the catalyst, fully mixing uniformly and discharging in a low-humidity environment protection atmosphere.
Table 1 examples 1-6 raw materials and ratios
Example 7
The silane modified SBR resin enhanced sealant comprises the following components in parts by weight:
preparing 40 parts by weight of the silane modified SBR resin of the class 1;
60 parts of MAX-350 resin;
80 parts of heavy calcium carbonate;
irganox 2451 serving as an antioxidant;
rheological additive Crayvallac SL 1 weight portion;
water removing agent A-1711 weight parts;
5601 parts by weight of silane coupling agent KH;
SUL-11A organotin catalyst 0.1 parts by weight.
Example 8
The silane modified SBR resin enhanced sealant comprises the following components in parts by weight:
preparing 40 parts by weight of the silane modified SBR resin of the class 1;
60 parts of MAX-350 resin;
70 parts of heavy calcium carbonate;
irganox 2455 weight portions as antioxidant;
10 parts by weight of a rheological aid Crayvallac SL;
water removing agent A-17110 weight portions;
56010 parts by weight of a silane coupling agent KH;
SUL-11A organotin catalyst 1 part by weight.
Comparative example 1
The sealant of this comparative example was prepared as described in example 4 except that the silane modified SBR resin was not added.
Comparative example 2
The sealant of this comparative example was prepared as described in example 4, except that the SBR resin was used in place of the silane modified SBR resin.
Comparative example 3
The sealant of this comparative example was prepared as described in example 4, except that the same amount of PB was selected for silane modification in the preparation of the silane-modified SBR resin.
Comparative example 4
The sealant of this comparative example was prepared in the same manner as in example 4 except that the same amount of PS was selected for silane modification in the preparation of the silane-modified SBR resin.
Comparative example 5
The sealant of this comparative example was prepared in the same manner as in example 1 except that in the preparation of the silane-modified SBR resin, the same amount of PB was selected for the silane modification.
Comparative example 6
The sealant of this comparative example was prepared in the same manner as in example 1 except that the same amount of PS was selected for silane modification in the preparation of the silane-modified SBR resin.
Examples of the experiments
1. Mechanical Properties
The mechanical properties of the sealants prepared in examples 1 to 6 and comparative examples 1 to 4 were tested, and the specific test method included:
1. shear strength: bonding material glass/glass, according to standard ISO 4587;
2. tensile property: reference standard astm d-412;
the test results are shown in table 2 below.
TABLE 2 Performance test results for sealants of the examples
As can be seen from the data in the table, the sealant material can effectively improve the tensile strength of the sealant by adding the block copolymer polymerized by the organosilicon end-capping PS and PB based on an anionic polymerization system.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. The preparation method of the silane modified SBR resin is characterized by comprising the following steps:
(1) synthesis of blocking agent
Taking aminosilane and benzaldehyde as raw materials, reacting in an organic solvent system, collecting a crude product, and filtering and distilling under reduced pressure to obtain a blocking agent for later use;
(2) synthesis of silane-modified SBR resin
Introducing measured PS and PB under a protective atmosphere, adding measured n-butyllithium to initiate a polymerization reaction, then adding the end capping agent obtained in the step (1) to perform end capping treatment, and discharging to obtain the product;
2. the method for preparing the silane-modified SBR resin of claim 1, wherein in the step (1), the aminosilane comprises KH 550;
the molar ratio of the benzaldehyde to the aminosilane is 1.1: 1.0.
3. the method of preparing silane-modified SBR resin of any one of claims 1 to 3, wherein in the step (1), the organic solvent comprises toluene;
the reaction temperature is 40-60 ℃, and the reaction time is 3-5 h.
4. The method of preparing silane-modified SBR resin according to any one of claims 1 to 3, wherein in the step (2), the molar ratio of PS, PB, n-butyllithium and the blocking agent is 1: 3: 2: 2.
5. the method of preparing silane-modified SBR resin according to any one of claims 1 to 4, wherein in the step (2), the temperature of the polymerization step is 40 to 60 ℃ and the temperature of the capping step is 50 to 70 ℃.
6. A silane-modified SBR resin produced by the process of any one of claims 1 to 5.
7. Use of the silane-modified SBR resin of claim 6 for the preparation of sealant materials.
8. The silane modified SBR resin enhanced sealant is characterized by comprising the following components in parts by weight:
10-90 parts by weight of the silane-modified SBR resin of claim 6;
10-90 parts by weight of silane modified polyether/polyurethane resin;
5-80 parts of filler;
1-10 parts of antioxidant;
1-10 parts of rheological additive;
1-10 parts of a water removing agent;
1-10 parts by weight of a silane coupling agent;
0.1-2 parts of catalyst.
9. The silane-modified SBR resin-reinforced sealant as claimed in claim 8, wherein:
the filler comprises at least one of light calcium or heavy calcium;
the silane coupling agent comprises at least one of 3-aminopropyltrimethoxysilane, N-beta- (aminoethyl) -gamma-aminopropyltrimethoxysilane, vinyl trimethoxysilane, gamma-aminopropyltriethoxysilane and gamma-glycidoxypropyltrimethoxysilane;
the catalyst comprises at least one of an organotin catalyst or an organobismuth catalyst.
10. The method for preparing the silane modified SBR resin reinforced sealant as claimed in claim 9 or 10, which comprises the steps of taking selected amounts of the silane modified SBR, the silane modified polyether/polyurethane, the filler, the antioxidant, the rheological aid, the water removal agent, the silane coupling agent and the catalyst, fully mixing and discharging under the protection atmosphere of low humidity environment.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210443133.0A CN114805712A (en) | 2022-04-25 | 2022-04-25 | Silane modified SBR resin, sealant and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210443133.0A CN114805712A (en) | 2022-04-25 | 2022-04-25 | Silane modified SBR resin, sealant and preparation method thereof |
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| CN114805712A true CN114805712A (en) | 2022-07-29 |
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| CN202210443133.0A Pending CN114805712A (en) | 2022-04-25 | 2022-04-25 | Silane modified SBR resin, sealant and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650269A (en) * | 2013-11-20 | 2015-05-27 | 中国石油化工股份有限公司 | Modified olefin polymer, preparation method and application thereof |
| US20200140726A1 (en) * | 2018-11-02 | 2020-05-07 | H.B. Fuller Company | Moisture curable hot melt sealant composition including silane functional polyurethane |
| CN114008125A (en) * | 2019-06-18 | 2022-02-01 | Jsr株式会社 | Polymer composition, crosslinked polymer, and tire |
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2022
- 2022-04-25 CN CN202210443133.0A patent/CN114805712A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650269A (en) * | 2013-11-20 | 2015-05-27 | 中国石油化工股份有限公司 | Modified olefin polymer, preparation method and application thereof |
| US20200140726A1 (en) * | 2018-11-02 | 2020-05-07 | H.B. Fuller Company | Moisture curable hot melt sealant composition including silane functional polyurethane |
| CN114008125A (en) * | 2019-06-18 | 2022-02-01 | Jsr株式会社 | Polymer composition, crosslinked polymer, and tire |
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