CN113896859A - Bio-based polyurethane damping material and preparation method and application thereof - Google Patents
Bio-based polyurethane damping material and preparation method and application thereof Download PDFInfo
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- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
Abstract
The invention relates to a bio-based polyurethane damping material and a preparation method and application thereof, relating to the field of damping materials and comprising the following raw materials in parts by weight: 23-40 parts by weight of bio-based polyurethane prepolymer, 6-36 parts by weight of suspension chain prepolymer and 1-5 parts by weight of cross-linking agent; the bio-based polyurethane prepolymer is obtained by reacting bio-based polyol and diisocyanate under the action of a catalyst, wherein the weight ratio of the bio-based polyol to the diisocyanate is (12-25): (9-16); the suspension chain prepolymer is obtained by reacting a terminal monohydroxy compound dissolved in a solvent with diisocyanate under the action of a catalyst. According to the invention, the branched chain is introduced into the main chain of the bio-based polyurethane prepolymer, and the bio-based polyol is used for replacing petroleum-based polyol, so that the damping effect is greatly improved, and the application range of the bio-based polyurethane damping material is widened.
Description
Technical Field
The invention relates to the technical field of damping materials, in particular to a bio-based polyurethane damping material, a preparation method of the bio-based polyurethane damping material and application of the bio-based polyurethane damping material.
Background
With the rapid development of scientific technology and the wide use of high-tech products, the vibration and noise generated by high-degree automation are visible everywhere in life and work, even can seriously damage the nervous system of people, harm the health of people, influence the normal use of equipment and instruments, reduce the precision of the equipment, shorten the service life of the equipment and the like, the influence of the vibration noise on daily production life is not small, and the improvement of the vibration noise is particularly critical.
With the rapid development of the industry, the conventional fossil fuel faces two challenges, firstly, the conventional fossil fuel is a non-renewable energy source, the gradual exhaustion of the conventional fossil fuel leads to the shortage of the fossil fuel resources around the world now, the price fluctuation is very large, secondly, the environmental problem is solved, the harm of the fossil fuel to the environment in the utilization process is huge, the influence of pollutants generated in the combustion process on the environment can cause the global climate change, carbon in the fossil fuel is converted into carbon dioxide to enter the atmosphere, the concentration of the carbon dioxide in the atmosphere is increased, the greenhouse effect is caused, and the gradual exhaustion of the conventional fossil fuel and the harm to the environment lead to the important significance of the development of bio-based renewable materials.
When the damping material, namely the vibration attenuation material, is subjected to the action of alternating stress, mechanical energy acting on an elastic component is stored like potential energy, then the mechanical energy is returned to an external material to be changed into elasticity, and the mechanical energy acting on a viscous part is not returned to the outside, the mechanical energy is converted into heat to be consumed due to internal consumption of the material, the heat is consumed, the amplitude of vibration is rapidly attenuated along with time, and the damping effect is achieved, the conversion and the dissipation of the energy are the damping effect, the damping effect can be represented by the dynamic mechanical characteristics of the material, including the storage modulus and the loss factor, the loss factor is a characteristic value representing damping, and the larger the loss factor is (tan delta is more than or equal to 0.3), and the better the damping effect is.
Polyurethane has become one of damping materials with higher research value and stronger practicability due to various raw material types, strong structural designability, simple preparation process, balanced property and wide application. The loss factor of the polyurethane damping material is low, the effective damping temperature range is generally 20-30 ℃ (when the damping factor tan delta is more than or equal to 0.3), and the temperature range is narrow, so that the range is greatly limited. Therefore, polyurethane damping materials must be modified to meet the demand for higher and higher damping materials.
Disclosure of Invention
Object of the Invention
In order to solve the problems of low loss factor and narrow effective damping temperature range of polyurethane damping materials in the prior art, the invention aims to provide a bio-based polyurethane damping material, a preparation method of the bio-based polyurethane damping material and application of the bio-based polyurethane damping material.
According to the invention, a branched chain is introduced into a main chain of bio-based polyurethane through molecular structure design, internal consumption is increased by increasing friction among molecular chains, and then, a suspension chain also contains abundant polar groups, so that a hydrogen bond can be formed with the polar groups in the main chain, energy is consumed through the breakage and recombination of the hydrogen bond, and the two are in mutual cooperation, so that excellent damping performance is endowed to the bio-based polyurethane damping material.
In the current research, in order to improve the damping performance of the bio-based polyurethane, a suspension chain is introduced through the molecular structure design, the friction between molecular chains is increased, and the bio-based polyol is used for replacing petroleum-based polyol, so that the damping effect is improved, and the application range of the bio-based polyurethane damping material is further widened.
Solution scheme
In order to achieve the purpose of the invention, the embodiment of the invention provides a bio-based polyurethane damping material, 23-40 parts by weight of bio-based polyurethane prepolymer, 6-36 parts by weight of suspension chain prepolymer and 1-5 parts by weight of cross-linking agent;
the bio-based polyurethane prepolymer is obtained by reacting bio-based polyol and diisocyanate under the action of a catalyst, wherein the weight ratio of the bio-based polyol to the diisocyanate is (12-25): (9-16);
the suspension chain prepolymer is obtained by reacting a terminal monohydroxy compound dissolved in a solvent with diisocyanate under the action of a catalyst, wherein the weight ratio of the terminal monohydroxy compound to the diisocyanate is (2-15): 3.5, the weight ratio of the solvent to the terminal monohydroxy compound is 1: (1-5), wherein the solvent in the suspension chain prepolymer can be removed in the preparation process of the bio-based polyurethane damping material.
Further, in the bio-based polyurethane prepolymer, the weight ratio of the bio-based polyol to the diisocyanate is (14-25): (9-15);
optionally, the bio-based polyol is one or two of sorbitol, soybean oil-based polyol, tung oil-based polyol, olive oil-based polyol, hydroxyl terminated polylactic acid and castor oil, optionally castor oil;
optionally, in the bio-based polyurethane prepolymer, the molecular weight of the bio-based polyol is 500-3000, and the average functionality is 2-4;
optionally, in the bio-based polyurethane prepolymer, the diisocyanate is one or two of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, dicyclohexylmethane diisocyanate and naphthalene diisocyanate; optionally toluene diisocyanate or diphenylmethane diisocyanate, optionally toluene diisocyanate (TDI100) or diphenylmethane diisocyanate (MDI 50).
Further: in the suspension chain prepolymer, the diisocyanate is toluene diisocyanate, and optionally toluene diisocyanate (TDI 100);
optionally, the terminal monohydroxy compound is one or more of diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, polyethylene glycol monomethyl ether 350, polyethylene glycol monomethyl ether 550 and polyethylene glycol monomethyl ether 750, and optionally one or more of diethylene glycol monobutyl ether, polyethylene glycol monomethyl ether 350, polyethylene glycol monomethyl ether 550 and polyethylene glycol monomethyl ether 750; optionally polyethylene glycol monomethyl ether 550.
Optionally, in the suspension chain prepolymer, a solvent is one or two of ethyl acetate, toluene, N-dimethylformamide and acetone; optionally acetone.
Optionally, in the pendant chain prepolymer, the weight ratio of the solvent to the terminal monohydroxy compound is 1:1.
Further, when the bio-based polyol is castor oil, the diisocyanate is toluene diisocyanate or diphenylmethane diisocyanate; the weight ratio of the bio-based polyol to the diisocyanate is 18.7: (9-15).
Alternatively, when the diisocyanate is toluene diisocyanate, the weight ratio of bio-based polyol to diisocyanate is 18.7: (9.5-11), optionally 18.7:10, optionally, the diisocyanate is toluene diisocyanate (TDI 100).
Alternatively, when the diisocyanate is diphenylmethane diisocyanate, the weight ratio of bio-based polyol to diisocyanate is 18.7: (13.5-15), optionally 18.7:14, optionally, the diisocyanate is diphenylmethane diisocyanate (MDI 50).
Further: the feed comprises the following raw materials in parts by weight: 28.7-32.7 parts by weight of bio-based polyurethane prepolymer, 9.98-25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent.
Optionally, the feed comprises the following raw materials in parts by weight: 28.7-32.7 parts by weight of bio-based polyurethane prepolymer, 25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent; optionally, the suspension chain prepolymer is obtained by reacting a solvent, polyethylene glycol monomethyl ether 550 and toluene diisocyanate according to a weight ratio of 11:11: 3.5; optionally, the bio-based polyurethane prepolymer is prepared from castor oil and diisocyanate in a weight ratio of 18.7: (10-14) obtaining a suspension chain prepolymer through reaction.
Optionally, the feed comprises the following raw materials in parts by weight: 28.7 parts by weight of bio-based polyurethane prepolymer, 25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent; optionally, the bio-based polyurethane prepolymer is obtained by reacting castor oil and toluene diisocyanate according to a weight ratio of 18.7: 10; optionally, the suspension chain prepolymer is obtained by reacting a solvent, polyethylene glycol monomethyl ether 550 and toluene diisocyanate according to a weight ratio of 11:11: 3.5;
optionally, the feed comprises the following raw materials in parts by weight: 32.7 parts by weight of bio-based polyurethane prepolymer, 25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent; optionally, the bio-based polyurethane prepolymer is obtained by reacting castor oil and diphenylmethane diisocyanate according to a weight ratio of 18.7: 14; optionally, the suspension chain prepolymer is obtained by reacting a solvent, polyethylene glycol monomethyl ether 550 and toluene diisocyanate in a weight ratio of 11:11: 3.5.
The weight ratio of the bio-based polyol and diisocyanate of the present invention is determined by the molar ratio of the average functionalities of the two, which may be 1: (1-1.2), for example, the molar ratio of functionality of 18.7g of castor oil to 10g of toluene diisocyanate is 1: 1.08.
Further: the cross-linking agent is trimethylolpropane or glycerol, optionally trimethylolpropane;
optionally, the solvent further comprises a second solvent for dissolving a cross-linking agent, wherein the weight ratio of the cross-linking agent to the second solvent is (3-5) to 10, optionally 3.3: 10; optionally, the second solvent adopts one or two of ethyl acetate, toluene, N-dimethylformamide and acetone; optionally acetone.
Optionally, in the bio-based polyurethane prepolymer or the pendant chain prepolymer, the catalyst is one or two of dibutyltin dilaurate, stannous octoate, triethylamine, triethylenediamine, zinc octoate and lead octoate.
On the other hand, the preparation method of the bio-based polyurethane damping material is characterized by comprising the following steps:
1) preparation of bio-based polyurethane prepolymer
Under the conditions of inert gas protection and medium-speed stirring, mixing the dehydrated bio-based polyol with diisocyanate, heating to 60-80 ℃, dropwise adding a catalyst, reacting for 0.5-2 h, and stopping the reaction to obtain an isocyanate-terminated bio-based polyurethane prepolymer;
2) preparation of suspension chain prepolymer
Under the conditions of inert gas protection and medium-speed stirring, mixing a terminal monohydroxy compound with a solvent, adding diisocyanate, mixing, heating to 60-70 ℃, adding a catalyst, and reacting for 1-2 hours to stop reaction to obtain an isocyanate-terminated pendant chain prepolymer;
3) synthesis of bio-based polyurethane damping material
Under the conditions of inert gas protection and medium-speed stirring, mixing the bio-based polyurethane prepolymer in the step 1) with the suspension chain prepolymer in the step 2), adding a cross-linking agent solution for mixing, reacting at 60-80 ℃ for 0.5-1 h to stop the reaction, vacuumizing to remove bubbles and most of solvent, casting and molding, standing at room temperature to fully volatilize residual solvent, then putting into an oven, heating to 60-80 ℃, preserving heat for 4-8 h, and standing at room temperature to obtain the bio-based polyurethane damping material.
Further, the inert gas in the steps 1) and 2) is N2；
Optionally, in the step 3), the crosslinking agent solution is obtained by dissolving a crosslinking agent in a second solvent;
alternatively, the method of removing the solvent and bubbles is: and reacting for 2-10 min under a vacuum condition.
Further, the dehydrated bio-based polyol process is: and (3) vacuumizing by using a vacuum pump at the heating temperature of 100-120 ℃, and dehydrating for 1-2.5 hours at the stirring speed of 200-450 r/min.
Further, the medium-speed stirring in the steps 1), 2) and 3) is 150-250 r/min.
In still another aspect, there is provided a use of the bio-based polyurethane damping material or the bio-based polyurethane damping material prepared by the method, wherein the bio-based polyurethane damping material is used to replace most petroleum-based polyurethane, and optionally, the application field includes transportation field including ships.
Advantageous effects
(1) According to the invention, the dangling chain is introduced into the polyurethane in a molecular structure design mode, so that on one hand, fossil energy is saved and the environment is protected, on the other hand, the damping performance of the bio-based polyurethane is improved, and the two are combined with each other, so that the application field of the bio-based polyurethane is greatly expanded. According to the invention, the branched chain is introduced into the main chain of the bio-based polyurethane prepolymer, the internal consumption is increased by increasing the friction between molecular chains, and the suspension chain prepolymer also contains abundant polar groups, so that hydrogen bonds can be formed with the polar groups in the main chain, and the energy is consumed by the breakage and recombination of the hydrogen bonds, so that the two groups are synergistic with each other, and the bio-based polyurethane has excellent damping performance. The loss factor of the bio-based polyurethane damping material reaches 1.56 (the performance of the existing damping material is mostly less than 1.0), the effective damping temperature range reaches 51 ℃, is far higher than the conventional temperature range (20-30 ℃), and belongs to a high-damping polyurethane elastomer material.
(2) The solvent is added into the suspension chain prepolymer, and the suspension chain prepolymer not only has the dissolving effect, but also has the main effect of preventing the reaction speed from being too high, and avoiding the generation of solid similar to foam, which causes the failure of subsequent experiments.
(3) According to the bio-based polyurethane damping material designed based on the molecular structure, firstly, bio-based polyol is used for replacing petroleum-based polyol to serve as a soft segment part, so that the exhaustion of fossil energy and the growing environmental problem can be relieved, and the interest of people in developing green composite materials by utilizing renewable resources is stimulated. And then a suspension chain is introduced into the hard segment by a molecular structure design method, so that the damping performance of the suspension chain is improved, the damping factor is greater than 1 and is as high as 1.56, and the application range of the bio-based polyurethane is widened to a great extent.
Drawings
One or more embodiments are illustrated by the corresponding figures in the drawings, which are not meant to be limiting. The word "exemplary" is used exclusively herein to mean "serving as an example, embodiment, or illustration. Any embodiment described herein as "exemplary" is not necessarily to be construed as preferred or advantageous over other embodiments.
FIG. 1 is a DMA comparison chart of comparative example 1, example 1 of the present invention, example 2, and example 3.
FIG. 2 is a DMA comparison of comparative example 1, comparative example 2, comparative example 3, inventive example 4.
FIG. 3 is a DMA comparison chart of comparative example 1, inventive example 3, and inventive example 4.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. Throughout the specification and claims, unless explicitly stated otherwise, the word "comprise", or variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated element or component but not the exclusion of any other element or component.
Furthermore, in the following detailed description, numerous specific details are set forth in order to provide a better understanding of the present invention. It will be understood by those skilled in the art that the present invention may be practiced without some of these specific details. In some embodiments, materials, elements, methods, means, and the like that are well known to those skilled in the art are not described in detail in order to not unnecessarily obscure the present invention.
Example 1
A preparation method of a bio-based polyurethane damping material based on molecular structure design comprises the following steps:
(1) placing 100g of Castor Oil (CO) into a three-neck flask connected with a stirrer and a vacuum pump, rapidly heating to 110 ℃ under the condition of rapid stirring (250r/min), and carrying out vacuum drying treatment (vacuum degree of-0.1 MPa) for 2h to obtain the dehydrated castor oil.
(2) Weighing 18.7g of the castor oil subjected to drying treatment in the step (1), placing the castor oil into a three-neck flask, adding 10g of toluene diisocyanate (TDI100), uniformly stirring at room temperature, connecting a stirrer (the rotating speed is 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the bio-based polyurethane prepolymer.
(3) 3..24g of diethylene glycol monobutyl ether was added to a three-necked flask, then the same amount of acetone solvent was added, and 3.5g of toluene diisocyanate (TDI100) was slowly added thereto over a period of N2Heating to 60 ℃ under the condition of atmosphere and moderate-speed stirring, and reacting for 1h to obtain the suspension chain prepolymer.
(4) 2.4g of Trimethylolpropane (TMP) is weighed into a beaker, 10g of acetone is added, and the beaker is placed in an oven at 70 ℃ until the trimethylolpropane is completely dissolved. The prepolymer and dissolved TMP in step (2) and step (3) are then rapidly mixed in N2Keeping the temperature at 60 ℃ for 0.5h under stirring in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the bio-based polyurethane damping material.
The damping performance of the bio-based polyurethane damping material of the embodiment is as follows: as shown in figure 1, the loss factor is 1.08, the temperature range is 38 ℃, and the damping performance is excellent within 27-65 ℃.
Example 2
A preparation method of a bio-based polyurethane damping material based on molecular structure design comprises the following steps:
(1) placing 100g of Castor Oil (CO) into a three-neck flask connected with a stirrer and a vacuum pump, rapidly heating to 110 ℃ under the condition of rapid stirring (250r/min), and carrying out vacuum drying treatment (vacuum degree of-0.1 MPa) for 2h to obtain the dehydrated castor oil.
(2) Weighing 18.7g of the castor oil subjected to drying treatment in the step (1), placing the castor oil into a three-neck flask, adding 10g of toluene diisocyanate (TDI100), uniformly stirring at room temperature, connecting a stirrer (the rotating speed is 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the bio-based polyurethane prepolymer.
(3) 7g of polyethylene glycol monomethyl ether 350 are placed in a three-necked flask, then an equal amount of acetone solvent is added, 3.5g of toluene diisocyanate (TDI100) is slowly added, and the mixture is stirred in a nitrogen atmosphere2Heating to 60 ℃ under the condition of atmosphere and moderate-speed stirring, and reacting for 1h to obtain the suspension chain prepolymer.
(4) Weighing 3.3g of Trimethylolpropane (TMP) into a beaker, adding 10g of acetone, and placing the beaker in an oven at 70 ℃ until the trimethylolpropane is completely dissolved. The prepolymer and dissolved TMP in step (2) and step (3) are then rapidly mixed in N2Keeping the temperature at 60 ℃ for 0.5h under stirring in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the bio-based polyurethane damping material.
The damping performance of the bio-based polyurethane damping material of the embodiment is as follows: as shown in figure 1, the loss factor is 1.2, the temperature range is 46 ℃, and the damping performance is excellent within 13-39 ℃.
Example 3
A preparation method of a bio-based polyurethane damping material based on molecular structure design comprises the following steps:
(1) placing 100g of Castor Oil (CO) into a three-neck flask connected with a stirrer and a vacuum pump, rapidly heating to 110 ℃ under the condition of rapid stirring (250r/min), and carrying out vacuum drying treatment (vacuum degree of-0.1 MPa) for 2h to obtain the dehydrated castor oil.
(2) Weighing 18.7g of the castor oil subjected to drying treatment in the step (1), placing the castor oil into a three-neck flask, adding 10g of toluene diisocyanate (TDI100), uniformly stirring at room temperature, connecting a stirrer (the rotating speed is 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the bio-based polyurethane prepolymer.
(3) 11g of polyethylene glycol monomethyl ether 550 was placed in a three-necked flask, followed by the addition of an equal amount of acetone solvent, 3.5g of toluene diisocyanate (TDI100) was slowly added thereto, and the mixture was heated under reduced pressure to room temperature2Heating to 60 ℃ under the condition of atmosphere and moderate-speed stirring, and reacting for 1h to obtain the suspension chain prepolymer.
(4) Weighing 3.3g of Trimethylolpropane (TMP) into a beaker, adding 10g of acetone, and placing the beaker in an oven at 70 ℃ until the trimethylolpropane is completely dissolved. The prepolymer and dissolved TMP in step (2) and step (3) are then rapidly mixed in N2Keeping the temperature at 60 ℃ for 0.5h under stirring in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the bio-based polyurethane damping material.
The damping performance of the bio-based polyurethane damping material of the embodiment is as follows: as shown in figures 1 and 3, the loss factor is 1.56, the temperature range is 51 ℃, and the damping performance is excellent within the temperature range of-6 ℃ to 45 ℃.
Example 4
A preparation method of a bio-based polyurethane damping material based on molecular structure design comprises the following steps:
(1) placing 100g of Castor Oil (CO) into a three-neck flask connected with a stirrer and a vacuum pump, rapidly heating to 110 ℃ under the condition of rapid stirring (250r/min), and carrying out vacuum drying treatment (vacuum degree of-0.1 MPa) for 2h to obtain the dehydrated castor oil.
(2) Weighing 18.7g of the castor oil subjected to drying treatment in the step (1), placing the castor oil in a three-neck flask, adding 14g of diphenylmethane diisocyanate (MDI50), uniformly stirring at room temperature, connecting a stirrer (rotating speed of 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the bio-based polyurethane prepolymer.
(3) 11g of polyethylene glycol monomethyl ether 550 was added to a three-necked flask, followed by addition of an equal amount of acetone solvent and slow addition of 3.5g of formazanPhenylene diisocyanate (TDI100) in N2Heating to 60 ℃ under the condition of atmosphere and moderate-speed stirring, and reacting for 1h to obtain the suspension chain prepolymer.
(4) Weighing 3.3g of Trimethylolpropane (TMP) into a beaker, adding 10g of acetone, and placing the beaker in an oven at 70 ℃ until the trimethylolpropane is completely dissolved. The prepolymer and dissolved TMP in step (2) and step (3) are then rapidly mixed in N2Keeping the temperature at 60 ℃ for 0.5h under stirring in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the bio-based polyurethane damping material.
The damping performance of the bio-based polyurethane damping material of the embodiment is as follows: as shown in figures 2 and 3, the loss factor is 1.57, the temperature range is 51 ℃, and the damping performance is excellent within the temperature range of 2-53 ℃.
Comparative example 1
A preparation method of a bio-based polyurethane damping material comprises the following steps:
(1) placing 100g of Castor Oil (CO) into a three-neck flask connected with a stirrer and a vacuum pump, rapidly heating to 110 ℃ under the condition of rapid stirring (250r/min), and carrying out vacuum drying treatment (vacuum degree of-0.1 MPa) for 2h to obtain the dehydrated castor oil.
(2) Weighing 18.7g of the castor oil subjected to drying treatment in the step (1), placing the castor oil into a three-neck flask, adding 10g of toluene diisocyanate (TDI100), uniformly stirring at room temperature, connecting a stirrer (the rotating speed is 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the bio-based polyurethane prepolymer.
(3) Weighing 2.4g of trimethylolpropane, putting the trimethylolpropane into a beaker, adding 10g of acetone, putting the beaker into a 70 ℃ oven, pouring the mixture into the step (2) after the mixture is completely dissolved, and adding N2Stirring at medium speed (180r/min) for 0.5h in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, then pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the bio-based polyurethane damping material.
The damping performance of the bio-based polyurethane damping material of the comparative example is as follows: the loss factor is 0.85, the temperature range is 30 ℃, and the damping performance is excellent within 35-65 ℃.
Comparative example 2
A preparation method of a damping material of petroleum-based polyurethane comprises the following steps:
(1) 100g of polytetrahydrofuran ether glycol (PTMG1000) is placed in a three-neck flask connected with a stirrer and a vacuum pump, the temperature is rapidly raised to 110 ℃ under the condition of rapid stirring (250r/min), and vacuum drying treatment (vacuum degree of-0.1 MPa) is carried out for 2h, thus obtaining the dehydrated polyol.
(2) Weighing the dried PTMG20g obtained in the step (1), placing the PTMG20g into a three-neck flask, adding 10.5g of diphenylmethane diisocyanate (MDI50), stirring uniformly at room temperature, connecting a stirrer (rotating speed of 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the polyurethane prepolymer.
(3) Weighing 1.8g of trimethylolpropane, putting the trimethylolpropane into a beaker, adding 10g of acetone, putting the beaker into a 70 ℃ oven, pouring the mixture into the step (2) after the mixture is completely dissolved, and adding N2Stirring at medium speed (180r/min) for 0.5h in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, then pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the petroleum-based polyurethane damping material.
The damping performance of the petroleum-based (PTMG1000) polyurethane damping material of the comparative example is as follows: the loss factor is 0.6, the temperature range is 35 ℃, and the damping performance is achieved within the temperature range of-22-13 ℃.
Comparative example 3
A preparation method of a petroleum-based polyurethane damping material based on molecular structure design comprises the following steps:
(1) 100g of polytetrahydrofuran ether glycol (PTMG) is placed in a three-neck flask connected with a stirrer and a vacuum pump, the temperature is rapidly raised to 110 ℃ under the condition of rapid stirring (250r/min), and vacuum drying treatment (vacuum degree of-0.1 MPa) is carried out for 2h to obtain the dehydrated polyol.
(2) Weighing the dried PTMG20g obtained in the step (1), placing the PTMG20g into a three-neck flask, adding 10.5g of diphenylmethane diisocyanate (MDI50), stirring uniformly at room temperature, connecting a stirrer (rotating speed of 180r/min), slowly heating to 70 ℃, and carrying out heat preservation reaction for 0.5h to obtain the polyurethane prepolymer.
(3) 8.3g of polyethylene glycol monomethyl ether 550 was placed in a three-necked flask, followed by the addition of an equal amount of acetone solvent, and then 2.6g of toluene diisocyanate (TDI100) was slowly added thereto in the presence of N2Heating to 60 ℃ under the condition of atmosphere and moderate-speed stirring, and reacting for 1h to obtain the suspension chain prepolymer.
(4) 2.6g of Trimethylolpropane (TMP) is weighed into a beaker, 10g of acetone is added, and the beaker is placed in an oven at 70 ℃ until the trimethylolpropane is completely dissolved. The prepolymer and dissolved TMP in step (2) and step (3) are then rapidly mixed in N2Keeping the temperature at 60 ℃ for 0.5h under stirring in the atmosphere, reacting for 3min in a vacuum state, removing the solvent and bubbles, pouring into a preheated polytetrafluoroethylene mold, standing at room temperature for 12h to naturally volatilize the solvent, then placing in an oven at 80 ℃ for 8h, and standing at room temperature for 2 days to obtain the petroleum-based polyurethane damping material.
The damping performance of the petroleum-based (PTMG) polyurethane damping material of the comparative example is as follows: the loss factor is 0.9, the temperature range is 75 ℃, and the damping performance is achieved at the temperature of minus 20-55 ℃.
Comparative example 4
The difference from example 3 is that no solvent is added in the preparation process of the suspension chain prepolymer in step (3), and the result shows that the reaction speed of step (3) is very high, so that the suspension chain prepolymer reacts to form a solid similar to foam, and subsequent experiments cannot be carried out.
It can be known from the above embodiments and as shown in fig. 1 to 3 that the bio-based polyurethane damping materials prepared in embodiments 1 to 4 have loss factors greater than 1, and the loss factors of embodiments 3 and 4 are as high as 1.56 and 1.57, and belong to damping materials with high damping performance, the bio-based polyurethane damping material prepared in comparative example 1 does not contain suspension chain prepolymer, the damping factor is only 0.85, the damping temperature range is 35 ℃, and the damping factors of comparative examples 2 and 3 are less than 1, and do not belong to materials with high damping performance.
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 such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (10)
1. The bio-based polyurethane damping material is characterized by comprising the following raw materials in parts by weight: 23-40 parts by weight of bio-based polyurethane prepolymer, 6-36 parts by weight of suspension chain prepolymer and 1-5 parts by weight of cross-linking agent;
the bio-based polyurethane prepolymer is obtained by reacting bio-based polyol and diisocyanate under the action of a catalyst, wherein the weight ratio of the bio-based polyol to the diisocyanate is (12-25): (9-16);
the suspension chain prepolymer is obtained by reacting a terminal monohydroxy compound dissolved in a solvent with diisocyanate under the action of a catalyst, wherein the weight ratio of the terminal monohydroxy compound to the diisocyanate is (2-15): 3.5, the weight ratio of the solvent to the terminal monohydroxy compound is 1: (1-5), wherein the solvent in the suspension chain prepolymer can be removed in the preparation process of the bio-based polyurethane damping material.
2. The bio-based polyurethane damping material according to claim 1, wherein: in the bio-based polyurethane prepolymer, the weight ratio of the bio-based polyol to diisocyanate is (14-25): (9-15);
optionally, the bio-based polyol is one or two of bio-based sorbitol-based polyol, soybean oil-based polyol, tung oil-based polyol, olive oil-based polyol, hydroxyl terminated polylactic acid and castor oil, optionally castor oil;
optionally, in the bio-based polyurethane prepolymer, the molecular weight of the bio-based polyol is 500-3000, and the average functionality is 2-4;
optionally, in the bio-based polyurethane prepolymer, the diisocyanate is one or two of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, dicyclohexylmethane diisocyanate and naphthalene diisocyanate; optionally toluene diisocyanate or diphenylmethane diisocyanate, optionally toluene diisocyanate TDI100 or diphenylmethane diisocyanate MDI 50.
3. The bio-based polyurethane damping material according to claim 1 or 2, wherein: in the suspension chain prepolymer, diisocyanate is toluene diisocyanate, and optionally toluene diisocyanate TDI 100;
optionally, the terminal monohydroxy compound is one or more of diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, polyethylene glycol monomethyl ether 350, polyethylene glycol monomethyl ether 550 and polyethylene glycol monomethyl ether 750, and optionally one or more of diethylene glycol monobutyl ether, polyethylene glycol monomethyl ether 350, polyethylene glycol monomethyl ether 550 and polyethylene glycol monomethyl ether 750; optionally polyethylene glycol monomethyl ether 550;
optionally, in the suspension chain prepolymer, a solvent is one or two of ethyl acetate, toluene, N-dimethylformamide and acetone; optionally acetone;
optionally, in the pendant chain prepolymer, the weight ratio of the solvent to the terminal monohydroxy compound is 1:1.
4. The bio-based polyurethane damping material according to any one of claims 1 to 3, wherein: when the bio-based polyol is castor oil, the diisocyanate is toluene diisocyanate or diphenylmethane diisocyanate; the weight ratio of the bio-based polyol to the diisocyanate is 18.7: (9-15);
alternatively, when the diisocyanate is toluene diisocyanate, the weight ratio of bio-based polyol to diisocyanate is 18.7: (9.5-11), optionally 18.7:10, optionally, the diisocyanate is toluene diisocyanate TDI 100;
alternatively, when the diisocyanate is diphenylmethane diisocyanate, the weight ratio of bio-based polyol to diisocyanate is 18.7: (13.5-15), optionally 18.7:14, optionally, the diisocyanate is diphenylmethane diisocyanate MDI 50.
5. The bio-based polyurethane damping material according to any one of claims 1 to 4, wherein: the feed comprises the following raw materials in parts by weight: 28.7-32.7 parts by weight of bio-based polyurethane prepolymer, 9.98-25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent;
optionally, the feed comprises the following raw materials in parts by weight: 28.7-32.7 parts by weight of bio-based polyurethane prepolymer, 25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent; optionally, the bio-based polyurethane prepolymer is prepared from castor oil and diisocyanate in a weight ratio of 18.7: (10-14) reacting to obtain a suspension chain prepolymer; optionally, the suspension chain prepolymer is obtained by reacting a solvent, polyethylene glycol monomethyl ether 550 and toluene diisocyanate according to a weight ratio of 11:11: 3.5;
optionally, the feed comprises the following raw materials in parts by weight: 28.7 parts by weight of bio-based polyurethane prepolymer, 25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent; optionally, the bio-based polyurethane prepolymer is obtained by reacting castor oil and toluene diisocyanate according to a weight ratio of 18.7: 10; optionally, the suspension chain prepolymer is obtained by reacting a solvent, polyethylene glycol monomethyl ether 550 and toluene diisocyanate according to a weight ratio of 11:11: 3.5;
optionally, the feed comprises the following raw materials in parts by weight: 32.7 parts by weight of bio-based polyurethane prepolymer, 25.5 parts by weight of suspension chain prepolymer and 3.3 parts by weight of cross-linking agent; optionally, the bio-based polyurethane prepolymer is obtained by reacting castor oil and diphenylmethane diisocyanate according to a weight ratio of 18.7: 14; optionally, the suspension chain prepolymer is obtained by reacting a solvent, polyethylene glycol monomethyl ether 550 and toluene diisocyanate in a weight ratio of 11:11: 3.5.
6. The bio-based polyurethane damping material according to any one of claims 1 to 5, wherein: the cross-linking agent adopts trimethylolpropane or glycerol, and is optionally trimethylolpropane;
optionally, the solvent further comprises a second solvent for dissolving a cross-linking agent, wherein the weight ratio of the cross-linking agent to the second solvent is (3-5) to 10, optionally 3.3: 10; optionally, the second solvent adopts one or two of ethyl acetate, toluene, N-dimethylformamide and acetone; optionally acetone;
optionally, in the bio-based polyurethane prepolymer or the pendant chain prepolymer, the catalyst is one or two of dibutyltin dilaurate, stannous octoate, triethylamine, triethylenediamine, zinc octoate and lead octoate.
7. A method for preparing the bio-based polyurethane damping material according to any one of claims 1 to 6, comprising:
1) preparation of bio-based polyurethane prepolymer
Under the conditions of inert gas protection and medium-speed stirring, mixing the dehydrated bio-based polyol with diisocyanate, heating to 60-80 ℃, dropwise adding a catalyst, reacting for 0.5-2 h, and stopping the reaction to obtain an isocyanate-terminated bio-based polyurethane prepolymer;
2) preparation of suspension chain prepolymer
Under the conditions of inert gas protection and medium-speed stirring, mixing a terminal monohydroxy compound with a solvent, adding diisocyanate for mixing, heating to 60-70 ℃, adding a catalyst, and reacting for 1-2 hours to stop reaction to obtain an isocyanate-terminated suspension chain prepolymer;
3) synthesis of bio-based polyurethane damping material
Under the conditions of inert gas protection and medium-speed stirring, mixing the bio-based polyurethane prepolymer in the step 1) with the suspension chain prepolymer in the step 2), adding a cross-linking agent solution for mixing, reacting at 60-80 ℃ for 0.5-1 h to stop the reaction, vacuumizing to remove bubbles and part of the solvent, casting and molding, standing at room temperature to fully volatilize the residual solvent, then putting into an oven, heating to 60-80 ℃, preserving heat for 4-8 h, and standing at room temperature to obtain the bio-based polyurethane damping material.
8. The preparation method of bio-based polyurethane damping material according to claim 7, wherein the inert gas in the steps 1) and 2) is N2；
Optionally, in the step 3), the crosslinking agent solution is obtained by dissolving a crosslinking agent in a second solvent;
alternatively, the method of removing the solvent and bubbles is: reacting for 2-10 min under a vacuum condition;
and/or the medium-speed stirring in the steps 1), 2) and 3) is 150-250 r/min.
9. The method for preparing bio-based polyurethane damping material according to claim 7 or 8, wherein the dehydrated bio-based polyol method is: and (3) vacuumizing by using a vacuum pump at the heating temperature of 100-120 ℃, and dehydrating for 1-2.5 hours at the stirring speed of 200-450 r/min.
10. Use of the bio-based polyurethane damping material according to any one of claims 1 to 6 or the bio-based polyurethane damping material prepared by the method according to any one of claims 7 to 9, wherein the bio-based polyurethane damping material is used in place of petroleum-based polyurethane damping material, optionally in applications including transportation fields including ships.
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| US20180022855A1 (en) * | 2016-07-21 | 2018-01-25 | John I. Nanos | Bio-based and hydrophilic polyurethane prepolymer and foam made therefrom |
| CN109863187A (en) * | 2016-09-30 | 2019-06-07 | 科思创德国股份有限公司 | Resin combination for damping material |
| CN107033324A (en) * | 2017-04-25 | 2017-08-11 | 华南理工大学 | A kind of wide temperature range polyurethane elastomer damping material designed based on network structure and method and application |
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