CN113801294B - High-strength, wide-temperature-range and high-damping polyurethane elastomer material and preparation method thereof - Google Patents

High-strength, wide-temperature-range and high-damping polyurethane elastomer material and preparation method thereof Download PDF

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CN113801294B
CN113801294B CN202110916372.9A CN202110916372A CN113801294B CN 113801294 B CN113801294 B CN 113801294B CN 202110916372 A CN202110916372 A CN 202110916372A CN 113801294 B CN113801294 B CN 113801294B
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prepolymer
temperature
chain
damping
polyurethane elastomer
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CN113801294A (en
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卢珣
蒋晓霖
王敏慧
马元浩
张文聪
张亚楠
容浩翔
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South China University of Technology SCUT
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
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    • C08G2350/00—Acoustic or vibration damping material

Abstract

The invention belongs to the technical field of damping materials, and discloses a high-strength wide-temperature-range high-damping polyurethane elastomer material and a preparation method thereof. The high-strength wide-temperature-range high-damping polyurethane elastomer material is mainly prepared from the following components: 11-45 parts of polyurethane prepolymer, 2-6 parts of small molecular chain extender and 4-16 parts of suspension chain prepolymer; the suspension chain prepolymer is obtained by the reaction of a hydroxyl-terminated compound and diisocyanate trimer under the action of a catalyst; the hydroxyl-terminated compound is a hydroxyl-terminated polymer, the polymer is obtained by polymerizing or copolymerizing acrylate monomers, and hydroxyl is introduced into the terminal group of the polymer. The invention also discloses a preparation method of the polyurethane elastomer material. The polyurethane elastomer material has the properties of high strength, wide temperature range and high damping, the effective damping temperature range (tan delta is more than or equal to 0.3) of the polyurethane elastomer material exceeds 150 ℃, and the tensile strength of the polyurethane elastomer material exceeds 15MPa.

Description

High-strength, wide-temperature-range and high-damping polyurethane elastomer material and preparation method thereof
Technical Field
The invention belongs to the technical field of damping materials, relates to a polyurethane elastomer, and particularly relates to a high-strength, wide-temperature-range and high-damping polyurethane elastomer material based on hydrogen bonding between a polyacrylate suspension chain and a main chain or a side chain and a preparation method thereof.
Background
With the rapid development of social science and technology, various mechanical automation is gradually popularized, and more mechanical vibration and noise are generated. On one hand, vibration and noise pollute the environment and harm the physical and psychological health of human beings; on the other hand, the precision, the stability and the reliability of mechanical equipment are greatly reduced. The adoption of the damping material is one of effective measures for controlling vibration and noise, and the good damping material can effectively absorb vibration mechanical energy, convert the vibration mechanical energy into heat energy and dissipate the heat energy, thereby reducing the adverse effects of harmful vibration and noise. The polymer base, especially the elastomer material has excellent damping characteristics due to the specific viscoelastic property, and is an important damping material. The wide temperature range high damping polyurethane material is required to be at least in the temperature range of 60-80 ℃, and the loss factor tan delta is more than or equal to 0.3. At present, research shows that damping and damping temperature range of the elastomer can be effectively improved by introducing a suspension branched chain on the main chain of the elastomer, but the mechanical strength of the elastomer is often low, and the actual use requirement cannot be met.
Chinese invention patents CN107033324A and CN110894277A disclose two wide temperature range polyurethane elastomer damping materials with long suspension connection, which are respectively prepared from the following components: patent CN107033324A: 11-37 parts of polyurethane prepolymer, 7-30 parts of suspension chain prepolymer and 1-25 parts of hydroxyl-terminated hyperbranched polyester; the polyurethane prepolymer is obtained by the reaction of polyester diol and diisocyanate under the action of a catalyst; the effective damping temperature range width of the damping material is about 170 ℃, the damping performance is excellent within the temperature range (-50 ℃ to 120 ℃), and the damping factor tan delta is more than or equal to 0.3. Patent CN110894277A: 12-48 parts of polyurethane prepolymer, 2-8 parts of small molecular chain extender containing disulfide bonds and 5-25 parts of suspension chain prepolymer; the polyurethane prepolymer is obtained by reacting polyurethane dihydric alcohol and diisocyanate under the action of a catalyst, and the pendant chain prepolymer is obtained by reacting a terminal monohydroxy compound and a diisocyanate trimer under the action of a catalyst. The damping material has an effective temperature range of over 170 ℃, excellent damping performance in a temperature range (-58-120 ℃) of the temperature range, a damping factor tan delta of more than or equal to 0.3, and can be used for a long time at 120 ℃. Although the effective damping temperature ranges of the two polyurethanes reach 170 ℃, the mechanical properties of the two polyurethanes are respectively 2.4MPa and 6.4MPa, and the mechanical properties still need to be further improved.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention aims to provide a high-strength, wide-temperature-range and high-damping polyurethane elastomer material and a preparation method thereof. The damping material is prepared by preparing single-end hydroxyl (methyl) acrylate oligomer (the molecular weight is about 1000-4000) by using a solution polymerization reaction method, then reacting the single-end hydroxyl (methyl) acrylate oligomer with diisocyanate trimer to prepare a suspension chain prepolymer, reacting polyester diol with diisocyanate to prepare a polyurethane prepolymer, then carrying out chain extension reaction on the polyurethane prepolymer by using a bifunctional micromolecule chain extender, and finally mixing the suspension chain prepolymer with the polyurethane prepolymer after chain extension to react. The damping material prepared by the method has the effective damping temperature range of about 150 ℃ (-52 ℃ -100 ℃), and the mechanical property of over 15MPa (17.42 +/-0.68 MPa).
The polyurethane elastomer damping material has excellent performance, a self-synthesized hydroxyl-terminated acrylate oligomer is introduced as a pendant chain, the pendant chain is designed to be simultaneously provided with a proton donor and a proton acceptor, and hydrogen bonding effects are formed between the pendant chain and between the pendant chain and a main chain, so that on one hand, the microphase separation degree of a system can be reduced, the damping performance of the material is improved, on the other hand, the loss of the mechanical property of the material caused by the introduction of a small amount of the pendant chain is compensated by the hydrogen bonding effect, and the balance of the damping and the mechanical property is realized.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a high-strength, wide-temperature-range and high-damping polyurethane elastomer material is mainly prepared from the following components: 11-45 parts of polyurethane prepolymer, 2-6 parts of small molecular chain extender and 4-16 parts of suspension chain prepolymer;
the polyurethane prepolymer is obtained by reacting polyester diol and diisocyanate under the action of a catalyst, wherein the weight ratio of the polyester diol to the diisocyanate is (10-40): (1-5), and the polyester diol needs to be subjected to vacuum dehydration treatment before reaction.
The molecular weight of the polyester dihydric alcohol is 1000-4000.
The polyester diol is more than one of polybutylene adipate, polybutylene succinate and polyethylene glycol adipate.
The diisocyanate is more than one of isophorone diisocyanate, 4' -diphenylmethane diisocyanate, hexamethylene diisocyanate and 2, 4-toluene diisocyanate.
In the polyurethane prepolymer, the catalyst is more than one of dibutyltin dilaurate or stannous octoate. The addition amount of the catalyst is 0.01-3 per mill of the weight of the polyester diol and the diisocyanate.
The micromolecule chain extender is more than one of 2,2 '-diaminodiphenyl disulfide, 4' -diaminodiphenyl disulfide, 2 '-dithiodibenzoic acid, 4' -dithiodibenzoic acid, bis (2-hydroxyethyl) disulfide and adipic dihydrazide.
The suspension chain prepolymer is obtained by reacting a hydroxyl-terminated compound with a diisocyanate trimer under the action of a catalyst, wherein the weight ratio of the hydroxyl-terminated compound to the diisocyanate trimer is (3-12): (1-4).
The hydroxyl-terminated compound is synthesized by acrylate micromolecule monomers through a solution polymerization method under the action of an initiator and a chain transfer agent.
The acrylate small molecular monomer is more than one of methyl methacrylate, ethyl methacrylate, butyl methacrylate, methyl acrylate, ethyl acrylate and butyl acrylate.
The molecular weight of the hydroxyl-terminated compound is 1000-4000;
the hydroxyl-terminated compound is preferably at least one of hydroxyl-terminated polymethyl methacrylate, hydroxyl-terminated polyethylmethacrylate, hydroxyl-terminated polybutyl methacrylate, hydroxyl-terminated polymethyl acrylate, hydroxyl-terminated polyethylacrylate, hydroxyl-terminated polybutyl acrylate, hydroxyl-terminated methyl methacrylate ethyl acrylate copolymer, hydroxyl-terminated methyl methacrylate butyl acrylate copolymer and hydroxyl-terminated ethyl acrylate butyl acrylate copolymer.
When the hydroxyl-terminated compound is a hydroxyl-terminated copolymer, the acrylate monomer is two or more of methyl methacrylate, ethyl methacrylate, butyl methacrylate, methyl acrylate, ethyl acrylate and butyl acrylate; such as: when the hydroxyl methyl methacrylate ethyl acrylate copolymer is prepared, the acrylate monomers are methyl methacrylate and ethyl acrylate; when the hydroxyl-terminated compound is a hydroxyl-terminated homopolymer, the acrylate monomer is one of methyl methacrylate, ethyl methacrylate, butyl methacrylate, methyl acrylate, ethyl acrylate and butyl acrylate;
in the case of a copolymer, the molar ratio between the two monomers is 1: (0.5-2); such as: when the hydroxyl-terminated methyl methacrylate-ethyl acrylate copolymer is adopted, the molar ratio of methyl methacrylate to ethyl methacrylate is 1: (0.5-2).
The initiator is azobisisobutyronitrile or dibenzoyl peroxide. The addition amount of the initiator is 0.5 to 8 percent of the weight of the acrylate small molecular monomer.
The chain transfer agent is mercaptoethanol or 3-mercapto-1-propanol. The dosage of the chain transfer agent is 1-60% of the weight of the acrylate micromolecule monomer.
In the suspension chain prepolymer, the diisocyanate trimer is more than one of toluene diisocyanate trimer, isophorone diisocyanate trimer and hexamethylene diisocyanate trimer; the catalyst is dibutyltin dilaurate or stannous octoate.
The addition amount of the catalyst is 0.01-3% of the weight of the terminal monohydroxy compound and the diisocyanate trimer.
The hydroxyl-terminated compound is prepared by the following method: reacting the acrylate micromolecule monomer at 60-70 ℃ for 1-3 h under the action of an initiator in a protective atmosphere and in a solvent, adding a chain transfer agent, continuously reacting for 5-8 h, and removing the solvent to obtain the hydroxyl-terminated compound. The solvent is ethyl acetate and the like.
The preparation method of the suspension chain prepolymer comprises the following steps: under the protective atmosphere, reacting a hydroxyl-terminated compound with diisocyanate trimer for 1-2 h at the temperature of 60-70 ℃ under the action of a catalyst to obtain a suspension chain prepolymer;
the specific preparation method of the polyurethane prepolymer comprises the following steps: under the protective atmosphere, the dehydrated polyester diol and diisocyanate react for 2 to 4 hours at 70 to 80 ℃ under the action of a catalyst to obtain the polyurethane prepolymer.
The preparation method of the high-strength, wide-temperature-range and high-damping polyurethane elastomer material comprises the following steps:
(1) Preparation of pendant chain prepolymers
Under the protective atmosphere, reacting a hydroxyl-terminated compound with diisocyanate trimer for 1-2 h at the temperature of 60-70 ℃ under the action of a catalyst to obtain a suspension chain prepolymer;
(2) Preparation of polyurethane prepolymers
Dehydrating the polyester dihydric alcohol to obtain dehydrated polyester dihydric alcohol; under the protective atmosphere, reacting dehydrated polyester diol with diisocyanate at 70-80 ℃ for 2-4 h under the action of a catalyst to obtain a polyurethane prepolymer;
(3) Chain extension of polyurethane prepolymer
Dissolving the micromolecular chain extender by using a solvent to obtain micromolecular chain extender solution; mixing the small molecular chain extender solution with the polyurethane prepolymer, and reacting for 1-2 h at 60-70 ℃ to obtain a chain-extended prepolymer;
(4) Preparation of polyurethane elastomer damping material
Under a protective atmosphere, uniformly mixing the chain-extended prepolymer with the suspension chain prepolymer, and molding and curing to obtain a high-strength wide-temperature-range high-damping polyurethane elastomer material; the curing condition is constant temperature of 60-70 ℃ for 12-24 h. The blending refers to rapid stirring and blending, and the stirring speed is 500-800 rpm.
And vacuumizing before curing.
In the step (3), the solvent is more than one of N, N-dimethylacetamide, toluene and acetone.
The polyurethane prepolymer in the step (2) is specifically prepared by: under the protective atmosphere, the dehydrated polyester dihydric alcohol and diisocyanateUniformly mixing cyanate ester, heating to 70-80 ℃, adding a catalyst, and keeping the temperature for 2-4 hours to obtain an elastic main chain prepolymer, namely a polyurethane prepolymer; the protective atmosphere is N 2 (ii) a The dehydration condition is that the vacuum dehydration is carried out for 1 to 2 hours at the temperature of between 100 and 120 ℃.
According to the invention, the acrylate oligomer suspension chain is introduced into the polyurethane, and the damping performance of the material is improved through the relaxation mode that the suspension chain is rich and different from the main chain. And hydrogen bonds can be formed between the suspension chains and between the suspension chains and the main chain, so that on one hand, the microphase separation degree of the system is reduced, the damping performance of the material is further improved, on the other hand, the mechanical performance loss of the material caused by the introduction of a small amount of suspension chains is compensated by virtue of the hydrogen bond action, and the balance of the damping performance and the mechanical performance of the material is realized.
Compared with the prior art, the invention has the following characteristics:
1) Aiming at the defects of the existing polyurethane damping material: the invention is based on the designability of the polyurethane material structure, and introduces the end monohydroxy acrylate oligomer into a polyurethane network as a suspension chain through the end monohydroxy acrylate oligomer. The damping performance of the material is improved by utilizing the suspension chains, and the mechanical property of the material is improved by forming intensive hydrogen bond actions between the suspension chains and the main chain.
2) The effective damping temperature range of the polyurethane damping material is more than 150 ℃, the damping performance is excellent in the temperature range of-52 ℃ to 100 ℃, the damping factor tan delta is more than or equal to 0.3, and the tensile strength of the material can reach 17.42 +/-0.68 MPa. The mechanical property of the existing polyurethane elastomer material with wide temperature range is lower than 10MPa.
Drawings
FIG. 1 is a schematic structural diagram of a high-strength, wide-temperature-range and high-damping polyurethane elastomer based on hydrogen bonding between suspension chains according to the present invention;
FIG. 2 is a graph comparing the tensile strength of polyurethane elastomers prepared in example 1, comparative example 1, and comparative example 2;
FIG. 3 is a dynamic mechanical spectrum at 10Hz of the polyurethane elastomers prepared in example 1, comparative example 1 and comparative example 2.
Detailed Description
The present invention will be further described with reference to specific examples, but the embodiments of the present invention are not limited thereto.
The damping performance test and the mechanical property test methods of the polyurethanes of the examples and the comparative examples are as follows:
and (3) testing molecular weight:
the molecular weight of the self-synthesized monohydroxy acrylate oligomer was measured by gel permeation chromatography (THF phase).
And (3) testing the damping performance:
the examples and comparative examples were subjected to dynamic mechanical test analysis using a DMA 242C dynamic mechanical analyzer (navy corporation, germany) under the following test conditions: and in a stretching mode, the scanning temperature range is-90-100 ℃, the heating rate is 5 ℃/min, and the test frequency is 10Hz.
And (3) testing mechanical properties:
tensile strength tests were carried out on the examples and comparative examples using an electronic universal tester (Zwick, germany) at a tensile rate of 100mm/min.
Example 1
A preparation method of a high-strength, wide-temperature-range and high-damping polyurethane elastomer comprises the following steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight of 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.01 part of dibutyltin dilaurate serving as a catalyst, reacting at constant temperature for 4 hours to obtain a prepolymer, and adding N 2 Storing in an atmosphere;
(2) Dissolving 2 parts by weight of 2,2' -diaminodiphenyl disulfide by using N, N-dimethylacetamide (DMAc), adding the solution into the prepolymer, and reacting at 60 ℃ for 2 hours to obtain a polyurethane prepolymer after chain extension;
(3) In weight fraction, in N 2 Under the protection of atmosphere, adding 1 part of HDI trimer into 3 parts of monohydroxy polyethylmethacrylate (molecular weight 1102) at constant speedStirring, keeping the temperature at 70 ℃, dropwise adding 0.01 part of catalyst dibutyltin dilaurate, keeping the temperature for 2 hours, stopping reaction to obtain a suspension chain prepolymer, N 2 Storing in an atmosphere;
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2) (the weight parts of the polyurethane prepolymer, the chain extender and the suspension chain prepolymer are respectively 24 parts, 2 parts and 4 parts), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
The specific preparation method of the hydroxyl-terminated compound in this embodiment is to dissolve 1 part of ethyl methacrylate and 0.05 part of azobisisobutyronitrile in 5 parts of ethyl acetate by weight, raise the temperature to 60 ℃, stir at constant temperature and constant speed (200 rad/min) for reaction for 1 hour, then add 0.5 part of mercaptoethanol, continue the reaction for 6 hours; and then placing the mixture in a vacuum oven, removing the solvent in vacuum, and keeping the mixture at 70 ℃ for 12 hours to obtain the hydroxyl-terminated poly (ethyl methacrylate).
Example 2
A preparation method of a high-strength, wide-temperature-range and high-damping polyurethane elastomer comprises the following process steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of catalyst dibutyltin dilaurate, reacting for 4 hours at constant temperature to obtain prepolymer, and reacting N 2 Storing in atmosphere;
(2) Dissolving 2 parts by weight of 2,2' -diamino diphenyl disulfide by 5 parts by weight of N, N-dimethyl acetamide, adding the dissolved solution into a prepolymer, and reacting at 60 ℃ for 2 hours to obtain a polyurethane prepolymer after chain extension;
(3) In terms of weight fraction, in N 2 Under the protection of atmosphere, adding 2 parts of HDI trimer into 6 parts of hydroxyl-terminated poly (ethyl methacrylate) (molecular weight 2404), uniformly stirring, keeping the temperature at 70 ℃, dropwise adding 0.01 part of catalyst dibutyltin dilaurate, keeping the temperature for 2 hours, stopping reaction to obtain a suspension chain prepolymer, and adding N 2 Storing in atmosphere.
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2) (the weight parts of the polyurethane prepolymer, the chain extender and the suspension chain prepolymer are respectively 24 parts, 2 parts and 8 parts), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
The specific preparation method of the hydroxyl-terminated compound in this embodiment is to dissolve 1 part of ethyl methacrylate and 0.05 part of azobisisobutyronitrile in 5 parts of solvent by weight, raise the temperature to 60 ℃, stir at constant temperature and constant speed (200 rad/min) for reaction for 2 hours, then add 0.35 part of mercaptoethanol, continue the reaction for 6 hours; and then placing the mixture in a vacuum oven, removing the solvent in vacuum, and keeping the mixture at 70 ℃ for 12 hours to obtain the hydroxyl-terminated poly (ethyl methacrylate).
Example 3
A preparation method of a high-strength, wide-temperature-range and high-damping polyurethane elastomer comprises the following process steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of catalyst dibutyltin dilaurate, reacting for 4 hours at constant temperature to obtain prepolymer, and reacting N 2 Storing in an atmosphere;
(2) Dissolving 2 parts by weight of 2,2' -diamino diphenyl disulfide by 5 parts by weight of N, N-dimethyl acetamide, adding the dissolved solution into a prepolymer, and reacting at 60 ℃ for 2 hours to obtain a polyurethane prepolymer after chain extension;
(3) In terms of weight fraction, in N 2 Under the protection of atmosphere, adding 3 parts of HDI tripolymer into 9 parts of hydroxyl-terminated poly (ethyl methacrylate) (molecular weight 3841), uniformly stirring, keeping the temperature at 70 ℃, dropwise adding 0.01 part of catalyst dibutyltin dilaurate, keeping the temperature for 2 hours, stopping reaction to obtain a suspension chain prepolymer, and adding N 2 Storing in atmosphere.
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
The specific preparation method of the hydroxyl-terminated compound in this embodiment is to dissolve 1 part of ethyl methacrylate and 0.05 part of azobisisobutyronitrile in 5 parts of solvent by weight, raise the temperature to 60 ℃, stir at constant temperature and constant speed (200 rad/min) for reaction for 3 hours, then add 0.25 part of mercaptoethanol, continue the reaction for 6 hours; and then placing the mixture in a vacuum oven, removing the solvent in vacuum, and keeping the mixture at the temperature of 70 ℃ for 12 hours to obtain the hydroxyl-terminated poly (ethyl methacrylate).
Example 4
The preparation method of the high-strength, wide-temperature-range and high-damping polyurethane elastomer comprises the following process steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of catalyst dibutyltin dilaurate, reacting for 4 hours at constant temperature to obtain prepolymer, and reacting N 2 Storing in an atmosphere;
(2) Dissolving 2 parts by weight of 2,2' -diamino diphenyl disulfide by using N, N-dimethyl acetamide, adding the dissolved solution into a prepolymer, and reacting for 2 hours at the temperature of 60 ℃ to obtain a polyurethane prepolymer after chain extension;
(3) In weight fraction, in N 2 Under the protection of atmosphere, adding 1 part of HDI tripolymer into 3 parts of hydroxyl-terminated poly-N-butyl methacrylate (with the molecular weight of 986), stirring at a constant speed, keeping the temperature at 70 ℃, dropwise adding 0.01 part of catalyst dibutyltin dilaurate, keeping the temperature for 2 hours, stopping reaction to obtain a suspension chain prepolymer, and adding N 2 Storing in atmosphere.
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
The specific preparation method of the hydroxyl-terminated compound in this embodiment is to dissolve 1 part of butyl methacrylate and 0.05 part of azobisisobutyronitrile in 5 parts of solvent by weight, raise the temperature to 60 ℃, stir at constant temperature and constant speed (200 rad/min) for reaction for 1 hour, then add 0.5 part of mercaptoethanol, continue the reaction for 6 hours; and then placing the mixture in a vacuum oven, removing the solvent in vacuum, and keeping the mixture at 70 ℃ for 12 hours to obtain the hydroxyl-terminated poly (ethyl methacrylate).
Example 5
A preparation method of a high-strength, wide-temperature-range and high-damping polyurethane elastomer comprises the following process steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of catalyst dibutyltin dilaurate, reacting for 4 hours at constant temperature to obtain prepolymer, and reacting N 2 Storing in an atmosphere;
(2) Dissolving 2 parts by weight of 2,2' -diamino diphenyl disulfide by using N, N-dimethyl acetamide, adding the dissolved solution into a prepolymer, and reacting for 2 hours at the temperature of 60 ℃ to obtain a polyurethane prepolymer after chain extension;
(3) In terms of weight fraction, in N 2 Under the protection of atmosphere, adding 2 parts of HDI tripolymer into 6 parts of hydroxyl-terminated poly-methyl butyl propionate (with the molecular weight of 1833), uniformly stirring, keeping the temperature at 70 ℃, dropwise adding 0.01 part of catalyst dibutyltin dilaurate, keeping the temperature for 2 hours, stopping reaction to obtain a suspension chain prepolymer, and adding N 2 Storing in atmosphere.
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
The specific preparation method of the hydroxyl-terminated compound in this embodiment is to dissolve 1 part of butyl methacrylate and 0.05 part of azobisisobutyronitrile in 5 parts of solvent by weight, raise the temperature to 60 ℃, stir at constant temperature and constant speed (200 rad/min) for reaction for 2 hours, then add 0.4 part of mercaptoethanol, continue the reaction for 6 hours; and then placing the mixture in a vacuum oven, removing the solvent in vacuum, and keeping the mixture at 70 ℃ for 12 hours to obtain the hydroxyl-terminated poly (ethyl methacrylate).
Example 6
A preparation method of a high-strength, wide-temperature-range and high-damping polyurethane elastomer comprises the following process steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of dibutyltin dilaurate serving as a catalyst, reacting at constant temperature for 4 hours to obtain prepolymer, and obtaining N 2 Storing in atmosphere;
(2) Dissolving 2 parts by weight of 2,2' -diamino diphenyl disulfide by 5 parts by weight of N, N-dimethyl acetamide, adding the dissolved solution into a prepolymer, and reacting at 60 ℃ for 2 hours to obtain a polyurethane prepolymer after chain extension;
(3) In weight fraction, in N 2 Under the protection of atmosphere, adding 3 parts of HDI tripolymer into 9 parts of hydroxyl-terminated poly-methyl butyl propionate (molecular weight 2610), stirring at a constant speed, keeping the temperature at 70 ℃, dropwise adding 0.01 part of catalyst dibutyltin dilaurate, keeping the temperature for 2 hours, stopping reaction to obtain a suspension chain prepolymer, and adding N 2 Storing in atmosphere.
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
The specific preparation method of the hydroxyl-terminated compound in this embodiment is to dissolve 1 part of butyl methacrylate and 0.05 part of azobisisobutyronitrile in 5 parts of solvent by weight, raise the temperature to 60 ℃, stir at constant temperature and constant speed (200 rad/min) for reaction for 3 hours, then add 0.3 part of mercaptoethanol, continue the reaction for 6 hours; and then placing the mixture in a vacuum oven, removing the solvent in vacuum, and keeping the mixture at the temperature of 70 ℃ for 12 hours to obtain the hydroxyl-terminated poly (ethyl methacrylate).
Comparative example 1
A preparation method of polyurethane elastomer containing a pendant chain comprises the following steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of catalyst dibutyltin dilaurate, reacting for 4 hours at constant temperature to obtain prepolymer, and reacting N 2 Storing in an atmosphere;
(2) Dissolving 2 parts by weight of 4,4' -diaminodiphenyl disulfide by using N, N-dimethylacetamide, adding the solution into the prepolymer, and reacting for 2 hours at 60 ℃ to obtain a polyurethane prepolymer after chain extension;
(3) In weight fraction, in N 2 Under the protection of atmosphere, adding 1 part of HDI trimer into 3 parts of terminal monohydroxy polysiloxane (molecular weight is 1000), stirring at a constant speed, keeping the temperature at 70 ℃, adding 0.01 part of catalyst dibutyltin dilaurate, and reacting at a constant temperature for 2 hours to obtain a pendant chain prepolymer;
(4) And (3) adding the suspension chain prepolymer obtained in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
Comparative example 2
A preparation method of polyurethane elastomer containing a pendant chain comprises the following steps:
(1) According to weight percentage, 20 parts of polybutylene adipate (molecular weight 2000) is stirred at 110 ℃ and vacuumized to remove water for 1 hour, the temperature is reduced to 80 ℃ after the water removal is finished, and N is introduced 2 Protecting, adding 4 parts of isophorone diisocyanate and 0.02 part of catalyst dibutyltin dilaurate, and reacting for 4 hours at constant temperature to obtain a prepolymer;
(2) Dissolving 2 parts by weight of 4,4' -diaminodiphenyl disulfide by using N, N-dimethylacetamide, adding the dissolved solution into a prepolymer, and reacting at 60 ℃ for 2 hours to obtain a polyurethane prepolymer after chain extension;
(3) In terms of weight fraction, in N 2 Under the protection of atmosphere, adding 1 part of HDI trimer into 3 parts of terminal monohydroxy polyethylene glycol monomethyl ether (molecular weight is 1000), stirring at constant speed, keeping the temperature at 70 ℃, and adding 0.01 part of catalystReacting dibutyltin dilaurate serving as a catalyst for 2 hours at constant temperature to obtain a suspension chain prepolymer;
(4) And (3) adding the suspension chain prepolymer in the step (3) into the polyurethane prepolymer subjected to chain extension in the step (2), quickly stirring uniformly, pouring into a polytetrafluoroethylene mold, defoaming in vacuum, curing and molding at 60 ℃, and keeping the temperature for 12 hours to obtain the polyurethane elastomer.
Compared with the example 1, the introduction of the polyacrylate pendant chain can be seen to form more hydrogen bonds in a system and influence the mechanical property of the material.
The examples and comparative performance test data are shown in table 1.
Table 1 shows the damping properties and mechanical properties of examples 1 to 6 and comparative examples 1 and 2
Figure BDA0003204794180000121
FIG. 1 is a schematic structural diagram of a high-strength, wide-temperature-range and high-damping polyurethane elastomer based on hydrogen bonding between suspension chains.
FIG. 2 is a graph showing mechanical properties of example 1 and comparative examples 1 and 2. As can be seen from FIG. 2, the polyacrylate pendant chain is adopted, and the hydrogen bond effect formed between the pendant chain and between the pendant chain and the main chain has an obvious effect on the improvement of the mechanical properties of the material.
FIG. 3 is a tan delta-T curve for example 1 and comparative examples 1, 2. As can be seen from FIG. 3, the use of the pendant polyacrylate chains, although increasing the hydrogen bonding between the chain segments, does not completely restrict the molecular motion of the pendant chains and thus reduces internal friction, and the material still has a damping temperature range exceeding 150 ℃ (-52 ℃ -100 ℃). Comparing the damping and mechanical properties of the embodiment 1 and the comparative examples 1 and 2, the finding shows that the design adopts the dangling chain with the proton donor and the proton acceptor, and through the hydrogen bond action between the dangling chain and between the dangling chain and the main chain, the method not only improves the microphase separation degree of the system and endows the material with better damping property, but also makes up the loss of the mechanical property of the material caused by the introduction of a small amount of dangling chain by virtue of the hydrogen bond action, and realizes the balance of the damping property and the mechanical property of the polyurethane material.
The polyurethane elastomer provided by the invention has obviously improved mechanical strength and has wider application fields such as aerospace, transportation and the like. For example, the suspension damper top rubber in the automobile shock absorption system is used as a structural material, and needs to have good mechanical property besides necessary damping property, the embodiment of the invention can meet the requirements on the aspects of damping property and mechanical property, and the Chinese patent application CN107033324A and CN110894277A are difficult to be applied in the fields because of lower mechanical property, and the high-strength, wide-temperature-range and high-damping polyurethane elastomer material obviously expands the application of high-damping polyurethane in the field of mechanical structure shock absorption materials.
The above examples are examples of the process for preparing high-strength, wide-temperature range and high-damping polyurethane elastomer according to the present invention, but the embodiments of the present invention are not limited by the above examples, and any other changes, modifications, substitutions, combinations and simplifications which do not depart from the spirit and principle of the present invention and are intended to be equivalent to the above examples are included in the scope of the present invention.

Claims (9)

1. A high-strength wide-temperature-range high-damping polyurethane elastomer material is characterized in that: the composition is mainly prepared from the following components: 11-45 parts of polyurethane prepolymer, 2-6 parts of micromolecule chain extender and 4-16 parts of suspension chain prepolymer;
the polyurethane prepolymer is obtained by reacting polyester diol and diisocyanate under the action of a catalyst;
the micromolecule chain extender is more than one of 2,2 '-diaminodiphenyl disulfide, 4' -diaminodiphenyl disulfide, 2 '-dithiodibenzoic acid, 4' -dithiodibenzoic acid and bis (2-hydroxyethyl) disulfide;
the pendant chain prepolymer is obtained by reacting a terminal monohydroxy compound and a diisocyanate trimer under the action of a catalyst;
the terminal monohydroxy compound is a terminal monohydroxy polymer, the polymer is obtained by polymerizing or copolymerizing acrylate monomers, and hydroxyl is introduced into the terminal monohydroxy group of the polymer;
in the pendant chain prepolymer, the weight ratio of the terminal monohydroxy compound to the diisocyanate trimer is (3-12): (1-4);
the molecular weight of the monohydroxy-terminated compound is 1000-4000; the terminal monohydroxy compound is obtained by polymerizing an acrylate small molecular monomer under the action of an initiator and a chain transfer agent; the chain transfer agent is mercaptoethanol or 3-mercapto-1-propanol;
the high-strength, wide-temperature-range and high-damping polyurethane elastomer material is prepared by the following method: and carrying out chain extension reaction on the polyurethane prepolymer and a micromolecular chain extender, and mixing the suspension chain prepolymer and the polyurethane prepolymer after chain extension reaction.
2. The high-strength wide-temperature-range high-damping polyurethane elastomer material as claimed in claim 1, wherein:
the acrylate small molecular monomer is more than one of methyl methacrylate, ethyl methacrylate, butyl methacrylate, methyl acrylate, ethyl acrylate and butyl acrylate;
the initiator is azobisisobutyronitrile or dibenzoyl peroxide;
the dosage of the chain transfer agent is 1-60% of the weight of the acrylate micromolecule monomer;
the addition amount of the initiator is 0.5-8% of the weight of the acrylate micromolecule monomer.
3. The high-strength, wide-temperature-range and high-damping polyurethane elastomer material according to claim 1, wherein: the terminal monohydroxy compound is prepared by the following method: reacting acrylate small molecular monomers in a protective atmosphere and a solvent at 60 to 70 ℃ for 1 to 3h under the action of an initiator, adding a chain transfer agent, continuously reacting for 5 to 8h, and removing the solvent to obtain the monohydroxy compound.
4. The high-strength, wide-temperature-range and high-damping polyurethane elastomer material according to claim 1, wherein: the terminal monohydroxy compound is more than one of terminal monohydroxy polymethyl methacrylate, terminal monohydroxy polyethyl methacrylate, terminal monohydroxy polybutyl methacrylate, terminal monohydroxy polymethyl acrylate, terminal monohydroxy polyethyl acrylate, terminal monohydroxy polybutyl acrylate, terminal monohydroxy ethyl methacrylate acrylate copolymer, terminal monohydroxy methyl methacrylate butyl acrylate copolymer and terminal monohydroxy ethyl acrylate butyl acrylate copolymer.
5. The high-strength wide-temperature-range high-damping polyurethane elastomer material as claimed in claim 1, wherein:
in the pendant chain prepolymer, the diisocyanate trimer is more than one of toluene diisocyanate trimer, isophorone diisocyanate trimer and hexamethylene diisocyanate trimer; the catalyst is dibutyltin dilaurate or stannous octoate;
in the polyurethane prepolymer, the weight ratio of the polyester diol to the diisocyanate is (10-40): (1-5);
in the polyurethane prepolymer, the molecular weight of the polyester diol is 1000-4000;
in the polyurethane prepolymer, the diisocyanate is more than one of isophorone diisocyanate, 4' -diphenylmethane diisocyanate, hexamethylene diisocyanate and 2, 4-toluene diisocyanate;
in the polyurethane prepolymer, the catalyst is more than one of dibutyltin dilaurate or stannous octoate.
6. The high-strength, wide-temperature-range and high-damping polyurethane elastomer material according to claim 1, wherein: the polyester diol needs to be subjected to vacuum dehydration treatment before reaction;
in the polyurethane prepolymer, the addition amount of the catalyst is 0.01-3 per mill of the weight of the polyester diol and the diisocyanate;
in the suspension chain prepolymer, the addition amount of the catalyst is 0.01 per mill to 3 per mill of the weight of the terminal monohydroxy compound and the diisocyanate trimer.
7. The high-strength, wide-temperature-range and high-damping polyurethane elastomer material according to claim 1, wherein:
the preparation method of the pendant chain prepolymer comprises the following steps: under the protective atmosphere, reacting a terminal monohydroxy compound with diisocyanate trimer at the temperature of 60-70 ℃ for 1-2h under the action of a catalyst to obtain a suspension chain prepolymer;
the specific preparation method of the polyurethane prepolymer comprises the following steps: and (2) reacting the dehydrated polyester diol with diisocyanate under the action of a catalyst for 2 to 4 hours at 70 to 80 ℃ in a protective atmosphere to obtain the polyurethane prepolymer.
8. The preparation method of the high-strength, wide-temperature-range and high-damping polyurethane elastomer material according to any one of claims 1 to 7, which is characterized by comprising the following steps: the method comprises the following steps:
1) Dissolving the micromolecular chain extender by using a solvent to obtain micromolecular chain extender solution; mixing the small-molecular chain extender solution with the polyurethane prepolymer, and reacting at 60 to 70 ℃ for 1 to 2h to obtain a chain-extended prepolymer;
2) Under a protective atmosphere, uniformly mixing the chain-extended prepolymer with the suspension chain prepolymer, and molding and curing to obtain a high-strength wide-temperature-range high-damping polyurethane elastomer material; the curing condition is constant temperature of 60 to 70 ℃ for 12 to 24h.
9. The application of the high-strength, wide-temperature-range and high-damping polyurethane elastomer material as claimed in any one of claims 1 to 7, is characterized in that:
the high-strength, wide-temperature-range and high-damping polyurethane elastomer material is used in the fields of aerospace and/or transportation and serves as a mechanical structure damping material.
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