CN113354788A - Polyurethane elastomer and preparation method thereof - Google Patents
Polyurethane elastomer and preparation method thereof Download PDFInfo
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- CN113354788A CN113354788A CN202110455068.9A CN202110455068A CN113354788A CN 113354788 A CN113354788 A CN 113354788A CN 202110455068 A CN202110455068 A CN 202110455068A CN 113354788 A CN113354788 A CN 113354788A
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- 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
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- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
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- C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6655—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
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- 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
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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Abstract
The invention discloses a polyurethane elastomer and a preparation method thereof, wherein the polyurethane elastomer comprises the following components: 60-65% of polyester polyol, 30-33% of diisocyanate and 1-9.5% of mixed chain-extending cross-linking agent, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate.
Description
Technical Field
The invention belongs to the field of polyurethane, and particularly relates to a polyurethane elastomer and a preparation method thereof.
Background
The polyurethane elastomer has the advantages of strong structure designability, high mechanical strength, wear resistance, recyclability, low rolling resistance and the like, but the polyurethane has poor heat resistance, particularly for the polyurethane elastomer only subjected to physical crosslinking, the long-term service temperature cannot exceed 80 ℃, and the application of the polyurethane elastomer in the industrial field is limited. Changing the hard segment content and the type of chain extender is the most important method for improving the heat resistance of the polyurethane elastomer.
Toluene diisocyanate and diphenylmethane diisocyanate are the most used diisocyanate, however, toluene diisocyanate exists isomer and two isocyanic acid radicals in diphenylmethane diisocyanate are not in the same plane due to methylene action, so that the rigid segment regularity of the prepared polyurethane elastomer is not high, and the heat resistance is poor. Meanwhile, due to the asymmetric structures of the toluene diisocyanate and the diphenylmethane diisocyanate, the synthesized polyurethane elastomer has high dynamic heat generation, which limits the application of the polyurethane elastomer. In order to improve the heat resistance of the polyurethane elastomer and expand the application range of the polyurethane elastomer, it is important to provide a polyurethane elastomer with good heat resistance.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a polyurethane elastomer and a preparation method thereof, and the method solves the problem that the polyurethane elastomer is poor in heat resistance;
in order to achieve the purpose, the invention provides the following technical scheme:
a polyurethane elastomer comprising: 60-65% of polyester polyol, 30-33% of diisocyanate and 1-9.5% of mixed chain-extending cross-linking agent, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is (1-3): (1-2): (1-5).
Preferably, the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 3: 1: 5.
preferably, the polyester polyol is a polycaprolactone polyol or a polycarbonate diol.
Preferably, the mixed chain extending crosslinker is two or more of 3,3 ' -dichloro-4, 4 ' -diaminodiphenylmethane, 3,5 dimethylthiotoluenediamine, 1, 4-butanediol, 1, 3-butanediol, 2, 3-butanediol, ethylene glycol, 1, 3-propanediol, 1, 3-cyclohexanol, 1, 4-cyclohexanediol, 2,2 ' -dimethyl-1, 3-propanediol, glycerol, 1, 6-hexanediol, diethanolamine, and trimethylolpropane.
A method of preparing a polyurethane elastomer comprising the steps of: 1) dehydrating polyester polyol at 90-100 ℃ in vacuum, and reacting the dehydrated polyester polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
2) mixing the mixed chain extension crosslinking agent and the diatomite powder, and performing ball milling to obtain a mixture;
3) and 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
Preferably, 2) mixing the chain-extending cross-linking agent and diatomite powder, performing ball milling, and mixing with the modified silicon carbide to obtain a mixture.
Preferably, the preparation method of the modified silicon carbide comprises the following steps: soaking silicon carbide in a surface treatment solvent for surface treatment, wherein the surface treatment solvent is one of acetone, chloroform, tetrahydrofuran, dioxane or dimethylformamide; then preparing a monomer acrylamide aqueous solution, adding a cross-linking agent into the monomer acrylamide aqueous solution, wherein the cross-linking agent is glycerol, and adjusting the pH value of the solution to 7-12; adding potassium persulfate and sodium bisulfite; and then carrying out polymerization at the polymerization temperature of 40-80 ℃ for 2-3 h to obtain the modified silicon carbide after polymerization.
Has the advantages that:
(1) according to the invention, the diisocyanate is prepared from dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, so that the structural symmetry and rigidity of the diisocyanate are high, and the polyurethane elastomer obtained by the preparation method has excellent heat resistance and skid resistance under the specific proportion.
(2) According to the preparation method of the polyurethane elasticity, provided by the invention, the polyurethane elasticity is prepared by a prepolymer method, and the obtained polyurethane elasticity is high in rigid section regularity and good in heat resistance by matching with specific diisocyanate.
Detailed Description
The present invention is further described in the following examples, which should not be construed as limiting the scope of the invention, but rather as providing the following examples which are set forth to illustrate and not limit the scope of the invention.
Example 1
1) Vacuum dehydrating polycaprolactone polyol at 90-100 ℃, and reacting the dehydrated polycaprolactone polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
60% of polyester polyol, 30% of diisocyanate, 8% of a mixed chain extension crosslinking agent and 2% of other components, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 1: 1: 1;
2) mixing the mixed chain extension crosslinking agent and the diatomite powder, and performing ball milling to obtain a mixture;
the mixed chain extension crosslinking agent is a mixture of 3,3 '-dichloro-4, 4' -diaminodiphenylmethane and 3, 5-dimethylthio toluene diamine.
3) And 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
Example 2
1) Vacuum dehydrating polycaprolactone polyol at 90-100 ℃, and reacting the dehydrated polycaprolactone polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
65% of polyester polyol, 33% of diisocyanate, 1% of a mixed chain-extending cross-linking agent and 1% of other components, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 3: 2: 5;
2) mixing the mixed chain extension crosslinking agent and the diatomite powder, and performing ball milling to obtain a mixture;
the mixed chain extension crosslinking agent is a mixture of glycerol, 1, 6-hexanediol, diethanolamine and trimethylolpropane.
3) And 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
Example 3
1) Vacuum dehydrating polycaprolactone polyol at 90-100 ℃, and reacting the dehydrated polycaprolactone polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
63% of polyester polyol, 32% of diisocyanate and 3% of mixed chain-extending cross-linking agent, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 2: 2: 1;
2) mixing the mixed chain extension crosslinking agent and the diatomite powder, and performing ball milling to obtain a mixture;
the mixed chain-extending crosslinking agent is two or more of 3,3 ' -dichloro-4, 4 ' -diaminodiphenylmethane, 3, 5-dimethylthiotoluenediamine, 1, 4-butanediol, 1, 3-butanediol, 2, 3-butanediol, ethylene glycol, 1, 3-propanediol, 1, 3-cyclohexanol, 1, 4-cyclohexanediol, 2,2 ' -dimethyl-1, 3-propanediol, glycerol, 1, 6-hexanediol, diethanolamine and trimethylolpropane
3) And 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
Example 4
1) Vacuum dehydrating polycaprolactone polyol at 90-100 ℃, and reacting the dehydrated polycaprolactone polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
60% of polyester polyol, 30% of diisocyanate and 9.5% of mixed chain-extending cross-linking agent, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 1: 1: 5
2) Mixing the mixed chain extension crosslinking agent and the diatomite powder, and performing ball milling to obtain a mixture;
the mixed chain extension crosslinking agent is a mixture of 3,3 '-dichloro-4, 4' -diaminodiphenylmethane, 3, 5-dimethylthiotoluenediamine, 1, 4-butanediol and 1, 3-butanediol;
3) and 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
Example 5
1) Vacuum dehydrating polycaprolactone polyol at 90-100 ℃, and reacting the dehydrated polycaprolactone polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
63% of polyester polyol, 32% of diisocyanate and 4% of mixed chain-extending cross-linking agent, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 3: 1: 5;
2) mixing the mixed chain extension crosslinking agent and diatomite powder, performing ball milling, and mixing the ball milled mixture with modified silicon carbide to obtain a mixture, wherein the preparation method of the modified silicon carbide comprises the following steps: soaking silicon carbide in a surface treatment solvent for surface treatment, wherein the surface treatment solvent is acetone; then preparing a monomer acrylamide aqueous solution, adding a cross-linking agent into the monomer acrylamide aqueous solution, wherein the cross-linking agent is glycerol, and adjusting the pH value of the solution to 7-12; adding potassium persulfate and sodium bisulfite; then carrying out polymerization at the polymerization temperature of 40-80 ℃ for 2-3 h to obtain modified silicon carbide after polymerization;
the mixed chain-extending crosslinking agent is two or more of 3,3 ' -dichloro-4, 4 ' -diaminodiphenylmethane, 3, 5-dimethylthiotoluenediamine, 1, 4-butanediol, 1, 3-butanediol, 2, 3-butanediol, ethylene glycol, 1, 3-propanediol, 1, 3-cyclohexanol, 1, 4-cyclohexanediol, 2,2 ' -dimethyl-1, 3-propanediol, glycerol, 1, 6-hexanediol, diethanolamine and trimethylolpropane
3) And 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
Comparative example 1
Comparative example 1 differs from example 1 only in that the polyurethane prepolymer does not contain diisocyanate and other preparation conditions and preparation method are the same as those of example 1.
Comparative example 2
Comparative example 1 differs from example 1 only in that the polyurethane prepolymer does not contain p-phenylene diisocyanate, and other preparation conditions and preparation methods are the same as those of example 1.
Comparative example 3
Comparative example 1 differs from example 1 only in that the polyurethane prepolymer does not contain 1, 5-naphthalene diisocyanate, and other preparation conditions and preparation methods are the same as those of example 1.
The performance data for examples 1-5 and comparative examples 1-3 are shown in Table 1 below
TABLE 1
As can be seen from Table 1, the polyurethane elastomers obtained in examples 1 to 5 have high elongation at break, high right-angle tear load, high tensile strength, and high right-angle tear strength at 80 ℃, and as can be seen from comparison of comparative examples 1 to 3 with example 1, the dimethylbiphenyl diisocyanate, p-phenylene diisocyanate, and 1, 5-naphthalene diisocyanate in the present invention play a decisive role as diisocyanates in the mechanical strength of the polyurethane elastomers at high temperatures, and the dimethylbiphenyl diisocyanate, p-phenylene diisocyanate, and 1, 5-naphthalene diisocyanate synergistically ensure that the obtained polyurethane elastomers have excellent heat resistance, and as a result of detection, the polyurethane elastomers obtained in examples 1 to 5 and comparative examples 1 to 3 have excellent wet skid resistance and low rolling resistance.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (7)
1. A polyurethane elastomer, comprising: 60-65% of polyester polyol, 30-33% of diisocyanate and 1-9.5% of mixed chain-extending cross-linking agent, wherein the diisocyanate comprises dimethyl biphenyl diisocyanate, p-phenylene diisocyanate and 1, 5-naphthalene diisocyanate, and the mass ratio of the dimethyl biphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is (1-3): (1-2): (1-5).
2. The polyurethane elastomer according to claim 1, wherein the mass ratio of the dimethylbiphenyl diisocyanate to the p-phenylene diisocyanate to the 1, 5-naphthalene diisocyanate is 3: 1: 5.
3. the polyurethane elastomer of claim 1, wherein the polyester polyol is a polycaprolactone polyol or a polycarbonate diol.
4. The polyurethane elastomer of claim 1, wherein the hybrid chain-extended crosslinker is two or more of 3,3 ' -dichloro-4, 4 ' -diaminodiphenylmethane, 3,5 dimethylthiotoluenediamine, 1, 4-butanediol, 1, 3-butanediol, 2, 3-butanediol, ethylene glycol, 1, 3-propanediol, 1, 3-cyclohexanol, 1, 4-cyclohexanediol, 2,2 ' -dimethyl-1, 3-propanediol, glycerol, 1, 6-hexanediol, diethanolamine, and trimethylolpropane.
5. A process for preparing the polyurethane elastomer of any one of claims 1-4, comprising the steps of: 1) dehydrating polyester polyol at 90-100 ℃ in vacuum, and reacting the dehydrated polyester polyol with diisocyanate at 80-90 ℃ for 1-2h in a heat preservation manner to obtain a polyurethane prepolymer;
2) mixing the mixed chain extension crosslinking agent and the diatomite powder, and performing ball milling to obtain a mixture;
3) and 2) mixing the polyurethane prepolymer and the mixture obtained in the step 2), adding a curing agent, uniformly mixing, pouring into a mold, defoaming in vacuum, and drying to obtain the polyurethane elastomer.
6. The method of polyurethane elastomer according to claim 5, wherein the step 2) is specifically,
2) and mixing the mixed chain extension crosslinking agent and the diatomite powder, performing ball milling, and mixing with the modified silicon carbide to obtain a mixture.
7. The method of preparing the polyurethane elastomer according to claim 6, wherein the modified silicon carbide is prepared by the following steps: soaking silicon carbide in a surface treatment solvent for surface treatment, wherein the surface treatment solvent is one of acetone, chloroform, tetrahydrofuran, dioxane or dimethylformamide; then preparing a monomer acrylamide aqueous solution, adding a cross-linking agent into the monomer acrylamide aqueous solution, wherein the cross-linking agent is glycerol, and adjusting the pH value of the solution to 7-12; adding potassium persulfate and sodium bisulfite; and then carrying out polymerization at the polymerization temperature of 40-80 ℃ for 2-3 h to obtain the modified silicon carbide after polymerization.
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| CN1417265A (en) * | 2002-12-16 | 2003-05-14 | 中国科学院长春应用化学研究所 | Silicon carbide surface modifying method |
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| CN1417265A (en) * | 2002-12-16 | 2003-05-14 | 中国科学院长春应用化学研究所 | Silicon carbide surface modifying method |
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| CN111187508A (en) * | 2020-02-25 | 2020-05-22 | 吴超群 | Preparation method of heat-resistant polyurethane elastomer |
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