CN114686154B - Heat-to-phase-change damping potting adhesive and preparation method thereof - Google Patents
Heat-to-phase-change damping potting adhesive and preparation method thereof Download PDFInfo
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- CN114686154B CN114686154B CN202210193683.1A CN202210193683A CN114686154B CN 114686154 B CN114686154 B CN 114686154B CN 202210193683 A CN202210193683 A CN 202210193683A CN 114686154 B CN114686154 B CN 114686154B
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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
- C09J175/06—Polyurethanes from polyesters
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The application relates to the field of C09J175/04, in particular to a heat-to-phase change damping potting adhesive and a preparation method thereof, 30-100 parts of polyurethane prepolymer component A and 10-100 parts of curing agent component B are adopted, and polyurethane elastomer with higher crystallinity and excellent damping performance at room temperature is prepared by controlling the soft and hard segment proportion of polyurethane and the prepolymer degree, solid-solid phase change occurs at first when the temperature is heated, and solid-liquid phase change occurs when the temperature is further increased, and a large amount of heat is absorbed in the phase change process, so that the aim of controlling the temperature is fulfilled, the heat-to-phase change damping adhesive can be used for damping, vibration reduction, high-temperature combustion, shock resistance and other environments, electronic components and the like in the shock environment are protected from being damaged, and the heat-to-phase change damping adhesive has high practical application value and market application potential.
Description
Technical Field
The application relates to the field of C09J175/04, in particular to a heat-to-phase change damping potting adhesive and a preparation method thereof.
Background
The prior electronic pouring sealant mainly comprises polyurethane pouring sealant, organic silicon pouring sealant and epoxy resin pouring sealant, and the different use environments have different requirements on the performance and safety of the pouring sealant, so that the types of the pouring sealant adopted are different, and the materials of the pouring sealant, the use amount of each material and the selection of the corresponding preparation process are different.
Chinese patent CN103396655B discloses a pouring sealant for magnetorheological damper and a preparation and use method thereof, and the preparation of epoxy powder pouring sealant is performed according to the strength, heat resistance and operability of the epoxy pouring sealant, and the provided epoxy pouring sealant has low viscosity and long operation time, but has weak cold and hot change resistance, is easy to generate cracks after being subjected to cold and hot impact, causes water vapor to infiltrate into electronic components from the cracks, and has poor moistureproof capability. And the cured gel has high hardness and brittleness, is easy to strain electronic components, cannot be opened after encapsulation, and has bad repairability. The polyurethane pouring sealant is mainly soft and elastic after being cured and can be repaired, chinese patent CN102102006B discloses a preparation method of the double-component polyurethane pouring sealant and a product thereof, wherein polyether polyol, a defoamer, an oligomer polyol, a catalyst, a plasticizer and a flame retardant are used as components A, and polyether polyol, isocyanate, an antioxidant, a plasticizer and a catalyst are used as components B to prepare the double-component polyurethane pouring sealant.
Therefore, the polyurethane elastomer with higher crystallinity and excellent damping performance at room temperature is prepared by controlling the proportion of soft and hard segments of polyurethane and the pre-polymerization degree of the pre-polymer, solid-solid phase change occurs when the temperature is heated, solid-liquid phase change occurs when the temperature is further increased, and a large amount of heat is absorbed in the phase change process, so that the purpose of controlling the temperature is achieved, the polyurethane elastomer can be used for damping, vibration reduction, high-temperature combustion, impact resistance and other environments, and electronic components and the like in the impact environment are protected from being damaged, and the polyurethane elastomer has high practical application value and market application potential.
Disclosure of Invention
The application provides a heat-to-phase change damping potting adhesive, which comprises the following raw materials in parts by weight: 30-100 parts of polyurethane prepolymer component A and 10-100 parts of curing agent component B.
The polyurethane pouring sealant has completely different performance differences due to different raw materials, the consumption of each raw material and the corresponding preparation process, and in order to ensure that the provided pouring sealant meets the requirements of service environments such as actual damping, vibration reduction, high-temperature combustion, impact resistance and the like and protects electronic components and the like under the impact environment from being damaged, the application is proved by a large number of creative tests, and when the mass ratio of the polyurethane prepolymer component A to the curing agent component B in the system is (30-100): and (35-100), the provided potting adhesive has excellent damping performance, bonding strength and mechanical property, effectively realizes the temperature control from heat to phase change, is applied to effective potting in damping, vibration reduction and impact resistance use environments, and effectively protects sensitive circuits or electronic components for a long time.
As a preferred embodiment, the polyurethane prepolymer component a comprises at least a diisocyanate; as a preferred technical scheme, the polyurethane prepolymer component A further comprises polyester diol and an organotin catalyst; as a preferred technical scheme, the curing agent component B at least comprises a polyol and an organotin catalyst;
as a preferable technical scheme, the diisocyanate in the polyurethane prepolymer component A is diphenylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate with symmetrical structure;
as a preferable technical scheme, the polyester diol in the polyurethane prepolymer component A is polycaprolactone diol, the number average molecular weight of the polycaprolactone diol is 500-3000, and the molecular distribution coefficient is 1.2-1.5; preferably, the polycaprolactone diol has a number average molecular weight of 1000;
as a preferable technical scheme, the organotin catalyst in the polyurethane prepolymer component A is at least one selected from dibutyltin dilaurate, dibutyltin oxide and stannous octoate; preferably, the organotin catalyst in the polyurethane prepolymer component A is stannous octoate or dibutyltin oxide;
as a preferable technical scheme, the polyol in the curing agent component B is at least one of polycaprolactone diol, castor oil, polyether polyol N210, polyether polyol N303 and 1, 4-butanediol; preferably, the polyol in the curing agent component B is polyether polyol N303 or polycaprolactone diol;
as a preferable technical scheme, the organotin catalyst in the curing agent component B is at least one selected from dibutyltin dilaurate, dibutyltin oxide and stannous octoate; preferably, the organotin catalyst in the curing agent component B is dibutyl tin dilaurate or stannous octoate;
the application also provides a preparation method of the heat-to-phase change damping potting adhesive, which at least comprises the following steps:
and adding the curing agent component B into the polyurethane prepolymer component A, carrying out vacuum defoaming for 5-10min, reacting for 1-5h at room temperature, and then curing for 2-10h at 60-100 ℃ to obtain the heat-to-phase change damping potting adhesive for pouring and potting.
As a preferable technical scheme, the preparation method of the heat-to-phase change damping potting adhesive specifically comprises the following steps:
(1) Polyol dehydration: adding polyalcohol into a three-mouth bottle with stirring, starting stirring, controlling stirring speed to 40-60 r/min, heating, vacuumizing and dehydrating when the temperature rises to 90 ℃, keeping the temperature at 100-140 ℃ and the vacuum degree below-0.098 MPa, dehydrating for 3-4h, and keeping the vacuum temperature below 33 ℃ after dehydrating is completed for standby;
(2) And (3) synthesizing a polyurethane prepolymer component A: preheating diisocyanate to 30-40 ℃, adding the dehydrated polyester diol and the organotin catalyst into a three-mouth bottle with stirring, controlling the stirring speed to 40-60 r/min, and performing moisture-proof reaction for 2-5h at 60-100 ℃ to obtain a polyurethane prepolymer component A for later use;
(3) And (3) preparing a curing agent component B: mixing the dehydrated polyol with an organotin catalyst to obtain a curing agent component B;
(4) Curing: and adding the curing agent component B into the polyurethane prepolymer component A, carrying out vacuum defoaming for 5-10min, reacting for 1-5h at room temperature, and then curing for 2-10h at 60-100 ℃ to obtain the heat-to-phase change damping potting adhesive for pouring and potting.
As a preferable technical scheme, the mass ratio of the polyurethane prepolymer component A to the curing agent component B is (30-45): (80-100), wherein the polyurethane prepolymer component A is diisocyanate, the curing agent component B comprises polyol and an organotin catalyst, and the mass ratio of the polyol to the organotin catalyst in the curing agent component B is 100: (0.1-0.001);
as a preferable technical scheme, the mass ratio of the polyurethane prepolymer component A to the curing agent component B is 100: (40-60), wherein the polyurethane prepolymer component A comprises diisocyanate, polyester diol and an organotin catalyst, and the mass ratio of the diisocyanate, the polyester diol and the organotin catalyst in the polyurethane prepolymer component A is (60-90): (80-100): 0.005; the curing agent component B comprises polyol and an organotin catalyst, and the mass ratio of the polyol to the organotin catalyst in the curing agent component B is 100:0.001;
the application uses polycaprolactone diol with the number average molecular weight of 500-3000 and the molecular distribution coefficient of 1.2-1.5 and diphenylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate with symmetrical structure as raw materials, and controls the soft and hard segment proportion of polyurethane and the pre-polymerization degree of prepolymer, so that the provided phase-change damping potting adhesive has higher crystallinity at room temperature, and the damping coefficient is more than or equal to 0.3 at 25-50 ℃, thereby being applicable to damping, vibration reduction, high-temperature combustion, impact resistance and other environments.
The heat-to-phase transition damping potting adhesive provided by the application firstly generates solid-solid phase transition when being heated, generates solid-liquid phase transition when the temperature is further increased, absorbs a large amount of heat in the phase transition process, thereby achieving the purpose of controlling the temperature, being applicable to environments such as damping, vibration reduction, high-temperature combustion, impact resistance and the like, protecting electronic components and the like in the impact environment from being damaged, and having high practical application value and market application potential.
According to the specific formula of the system, the polyol is dehydrated and then reacts with the diisocyanate, and vacuum defoaming is carried out during the reaction, so that the diisocyanate and the polyol in the system are ensured to fully react, the provided heat-to-phase change damping potting adhesive has excellent tensile strength, elongation at break and bonding tensile shear strength, a large amount of foaming after potting is avoided, the surface of the solidified colloid is smooth, and the service life of the potting adhesive is prolonged.
The beneficial effects are that:
1. the mass ratio of the polyurethane prepolymer component A to the curing agent component B is controlled to be (30-100): and (35-100), the provided potting adhesive has excellent damping performance, bonding strength and mechanical property, effectively realizes the temperature control from heat to phase change, is applied to effective potting in damping, vibration reduction and impact resistance use environments, and effectively protects sensitive circuits or electronic components for a long time.
2. The application uses polycaprolactone diol with the number average molecular weight of 500-3000 and the molecular weight distribution coefficient of 1.2-1.5 and diphenylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate with symmetrical structure as raw materials, and controls the soft and hard segment proportion of polyurethane and the pre-polymerization degree of prepolymer, so that the provided phase-change damping potting adhesive has higher crystallinity at room temperature, and the damping coefficient is more than or equal to 0.3 at 25-50 ℃, thereby being applicable to damping, vibration reduction, high-temperature combustion, impact resistance and other environments.
3. The heat-to-phase transition damping potting adhesive provided by the application firstly generates solid-solid phase transition when being heated, generates solid-liquid phase transition when the temperature is further increased, absorbs a large amount of heat in the phase transition process, thereby achieving the purpose of controlling the temperature, being applicable to environments such as damping, vibration reduction, high-temperature combustion, impact resistance and the like, protecting electronic components and the like in the impact environment from being damaged, and having high practical application value and market application potential.
4. According to the specific formula of the system, the polyol is dehydrated and then reacts with the diisocyanate, and vacuum defoaming is carried out during the reaction, so that the diisocyanate and the polyol in the system are ensured to fully react, the provided heat-to-phase change damping potting adhesive has excellent tensile strength, elongation at break and bonding tensile shear strength, a large amount of foaming after potting is avoided, the surface of the solidified colloid is smooth, and the service life of the potting adhesive is prolonged.
Detailed Description
Example 1
In one aspect, embodiment 1 of the application provides a heat-to-phase change damping potting adhesive, which is prepared from the following raw materials in parts by weight: 45 parts of polyurethane prepolymer component A and 80 parts of curing agent component B.
The mass ratio of the polyurethane prepolymer component A to the curing agent component B is 45:80, wherein the polyurethane prepolymer component A is diisocyanate, the curing agent component B comprises polyol and an organotin catalyst, and the mass ratio of the polyol to the organotin catalyst in the curing agent component B is 100:0.08;
the diisocyanate in the polyurethane prepolymer component A is diphenylmethane-4, 4' -diisocyanate with symmetrical structure; the diphenylmethane-4, 4' -diisocyanate was liquefied MDI, purchased from plumeria chemical group co.
The organotin catalyst in the polyurethane prepolymer component A is dibutyl tin oxide;
the polyol in the curing agent component B is polycaprolactone diol, and the number average molecular weight of the polycaprolactone diol is 1000;
the organic tin catalyst in the curing agent component B is stannous octoate;
example 2
In one aspect, embodiment 2 of the application provides a heat-to-phase change damping potting adhesive, which is prepared from the following raw materials in parts by weight: 100 parts of polyurethane prepolymer component A and 60 parts of curing agent component B.
The mass ratio of the polyurethane prepolymer component A to the curing agent component B is 100:60, wherein the polyurethane prepolymer component A comprises diisocyanate, polyester diol and an organotin catalyst, and the mass ratio of the diisocyanate, the polyester diol and the organotin catalyst in the polyurethane prepolymer component A is 80:100:0.005; the curing agent component B comprises polyol and an organotin catalyst, and the mass ratio of the polyol to the organotin catalyst in the curing agent component B is 100:0.001;
the diisocyanate in the polyurethane prepolymer component A is diphenylmethane-4, 4' -diisocyanate with symmetrical structure; the diphenylmethane-4, 4' -diisocyanate was liquefied MDI, purchased from plumeria chemical group co.
The polyester diol in the polyurethane prepolymer component A is polycaprolactone diol, and the number average molecular weight of the polycaprolactone diol is 1000;
the organotin catalyst in the polyurethane prepolymer component A is stannous octoate;
the polyol in the curing agent component B is polyether polyol N303;
the organic tin catalyst in the curing agent component B is stannous octoate;
the embodiment 2 of the application provides a preparation method of a heat-to-phase change damping potting adhesive, which comprises the following steps:
(1) Polyol dehydration: adding polyalcohol into a three-mouth bottle with stirring, starting stirring, controlling stirring speed to be 50 r/min, heating, vacuumizing and dehydrating when the temperature rises to 90 ℃, keeping the temperature at 120 ℃ and the vacuum degree below-0.098 MPa, dehydrating for 3 hours, and keeping the vacuum and cooling to below 33 ℃ for standby after dehydrating;
(2) And (3) synthesizing a polyurethane prepolymer component A: preheating diisocyanate to 35 ℃, adding the polyester diol and the organotin catalyst after water removal cooling into a three-port bottle with stirring, controlling the stirring speed to be 50 r/min, and performing moisture-proof reaction for 3 hours at 80 ℃ to obtain a polyurethane prepolymer component A for later use;
(3) And (3) preparing a curing agent component B: mixing the dehydrated polyol with an organotin catalyst to obtain a curing agent component B;
(4) Curing: and adding the curing agent component B into the polyurethane prepolymer component A, carrying out vacuum defoaming for 8min, reacting for 1h at room temperature, and then curing for 4h at 70 ℃ to obtain the heat-to-phase change damping potting adhesive for pouring and potting.
The damping coefficient of the heat-to-phase-change damping potting adhesive is more than 0.3 at 25-60 ℃, solid-solid phase change can be generated at room temperature of 110 ℃, and solid-liquid phase change can be generated at the temperature of more than 110 ℃.
Comparative example 1
Comparative example 1 of the present application provides a heat-to-phase change damping potting adhesive, which is different from example 1 in that the polyol in the curative component B is polycaprolactone diol P210.
Comparative example 2
Comparative example 2 of the present application provides a heat-to-phase change damping potting adhesive, which is different from example 1 in that the diisocyanate in the polyurethane prepolymer component a is toluene diisocyanate.
Comparative example 3
Comparative example 3 of the present application provides a heat to phase change damping potting adhesive, which is different from example 1 in that the polyol in the curative component B is polyether polyol N210.
Performance test method
(1) The tensile strength of the heat-to-phase change damping potting adhesive prepared in examples and comparative examples was tested with reference to the national standard.
(2) The thermal-to-phase-change damping potting adhesive prepared in examples and comparative examples was tested for elongation at break with reference to national standards.
(3) The aluminum-aluminum bonding tensile shear strength of the heat-to-phase change damping potting adhesives prepared in examples and comparative examples was tested with reference to the national standard.
(4) The hardness of the heat-to-phase change damping potting adhesive prepared in examples and comparative examples was tested with reference to the national standard.
Table 1 the performance test results of the heat-to-phase change damping potting adhesives prepared in examples 1-2 and comparative examples 1-3.
Claims (6)
1. The heat-to-phase change damping potting adhesive is characterized by comprising the following raw materials in parts by weight: 30-100 parts of polyurethane prepolymer component A and 10-100 parts of curing agent component B;
the polyurethane prepolymer component A at least comprises diisocyanate, wherein the diisocyanate in the polyurethane prepolymer component A is diphenylmethane-4, 4' -diisocyanate or hexamethylene diisocyanate with symmetrical structure;
the polyurethane prepolymer component A also comprises polyester diol, wherein the polyester diol in the polyurethane prepolymer component A is polycaprolactone diol, the number average molecular weight of the polycaprolactone diol is 1000, and the molecular distribution coefficient is 1.2-1.5;
the curing agent component B at least comprises polyol and an organotin catalyst.
2. The heat-to-phase change damping potting adhesive according to claim 1, wherein the mass ratio of the polyurethane prepolymer component A to the curing agent component B is (30-100): (35-100).
3. The heat to phase change damping potting adhesive of claim 1, wherein the polyurethane prepolymer component a further comprises an organotin catalyst.
4. The heat-to-phase change damping potting adhesive of claim 1, wherein the polyol in the hardener component B is at least one of polycaprolactone diol, castor oil, polyether polyol N210, polyether polyol N303, 1, 4-butanediol.
5. The heat-to-phase change damping potting adhesive of claim 4, wherein the organotin catalyst in the hardener component B is at least one selected from the group consisting of dibutyltin dilaurate, dibutyltin oxide, and stannous octoate.
6. A method of preparing a heat to phase change damping potting adhesive according to any one of claims 1 to 5, comprising at least the steps of: and adding the curing agent component B into the polyurethane prepolymer component A, carrying out vacuum defoaming for 5-10min, reacting for 1-5h at room temperature, and then curing for 2-10h at 60-100 ℃ to obtain the heat-to-phase change damping potting adhesive for pouring and potting.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210193683.1A CN114686154B (en) | 2022-03-01 | 2022-03-01 | Heat-to-phase-change damping potting adhesive and preparation method thereof |
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| CN202210193683.1A CN114686154B (en) | 2022-03-01 | 2022-03-01 | Heat-to-phase-change damping potting adhesive and preparation method thereof |
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| CN114686154B true CN114686154B (en) | 2023-09-26 |
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| EP1632515A2 (en) * | 2003-12-13 | 2006-03-08 | Dow Gloval Technologies Inc. | Polyurethane reactive composition |
| CN102102006A (en) * | 2010-12-20 | 2011-06-22 | 东莞市宏达聚氨酯有限公司 | Method for preparing bi-component polyurethane pouring sealant and product thereof |
| CN105885767A (en) * | 2016-06-24 | 2016-08-24 | 绵阳惠利电子材料有限公司 | MDI-base polyurethane electronic pouring sealant as well as preparation method and application method thereof |
| CN110606927A (en) * | 2019-08-12 | 2019-12-24 | 黎明化工研究设计院有限责任公司 | High-performance polyurethane damping material and preparation method thereof |
| CN111533883A (en) * | 2020-05-11 | 2020-08-14 | 青岛爱尔家佳新材料股份有限公司 | Ship filling sealing damping vibration attenuation material and preparation method thereof |
| CN113429541A (en) * | 2021-07-15 | 2021-09-24 | 盛鼎高新材料有限公司 | Preparation method of polyurethane elastomer |
-
2022
- 2022-03-01 CN CN202210193683.1A patent/CN114686154B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1632515A2 (en) * | 2003-12-13 | 2006-03-08 | Dow Gloval Technologies Inc. | Polyurethane reactive composition |
| CN102102006A (en) * | 2010-12-20 | 2011-06-22 | 东莞市宏达聚氨酯有限公司 | Method for preparing bi-component polyurethane pouring sealant and product thereof |
| CN105885767A (en) * | 2016-06-24 | 2016-08-24 | 绵阳惠利电子材料有限公司 | MDI-base polyurethane electronic pouring sealant as well as preparation method and application method thereof |
| CN110606927A (en) * | 2019-08-12 | 2019-12-24 | 黎明化工研究设计院有限责任公司 | High-performance polyurethane damping material and preparation method thereof |
| CN111533883A (en) * | 2020-05-11 | 2020-08-14 | 青岛爱尔家佳新材料股份有限公司 | Ship filling sealing damping vibration attenuation material and preparation method thereof |
| CN113429541A (en) * | 2021-07-15 | 2021-09-24 | 盛鼎高新材料有限公司 | Preparation method of polyurethane elastomer |
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| CN114686154A (en) | 2022-07-01 |
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