Polyurethane foam material for bicycle seat cushion and preparation method thereof

By using green chemical means in polyurethane foaming materials to prepare new polyisocyanates and graft antibacterial agents, the problem that polyurethane soft foaming materials are prone to contamination with sweat and breeding microorganisms is solved, achieving a high antibacterial rate and mechanical properties, and meeting the requirements of green chemistry.

CN119241810BActive Publication Date: 2025-04-04天津市全福车业有限公司
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Patent Information

Application Number
CN202411766353.2
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-12-04
Publication Date
2025-04-04
Estimated Expiration
2044-12-04

AI Technical Summary

Technical Problem

Existing polyurethane soft foam materials are prone to be contaminated with sweat and cause microorganisms to grow when in contact with the human body, which is difficult to disassemble and clean, resulting in fading, stains and odor residues, accelerate biodegradation, reduce mechanical strength, shorten product service life, and pose a threat to human health.

Method used

A new polyisocyanate was prepared by green chemical means, and three different antibacterial agents were grafted onto the polyether polyol to prepare polyurethane foaming materials with antibacterial properties through polycondensation reaction.

Benefits of technology

It achieves a high antibacterial rate of polyurethane foamed materials, while maintaining the mechanical properties of the materials, reducing the use of toxic raw materials and pollutant emissions, and complying with green chemical requirements.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention belongs to the technical field of antibacterial polyurethane materials, and in particular, relates to a polyurethane foam material for bicycle seat cushions and a preparation method thereof. The above-mentioned polyurethane foam material for bicycle seat cushions is prepared by mixing and foaming the following materials in parts by weight: 30-35 parts of polyisocyanate; 12-16 parts of antibacterial polyether polyol; 40-50 parts of polyether polyol; 1-2 parts of catalyst; 3-5 parts of foaming agent; 2-4 parts of cross-linking agent; 0.5-1.5 parts of surfactant; the present invention adopts green chemical means to prepare polyisocyanate containing three isocyanate groups, which reduces the use of toxic raw materials and reduces pollutant emissions; three different antibacterial agents are grafted on polyether polyol, and then polyisocyanate, antibacterial polyether polyol and conventional polyether polyol are polycondensed to prepare polyurethane foam material with antibacterial properties, which provides a new synthesis idea for preparing antibacterial polyurethane.
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Description

Technical Field

[0001] The invention belongs to the technical field of antibacterial polyurethane materials, and in particular relates to a polyurethane foam material for a bicycle seat cushion and a preparation method thereof. Background Art

[0002] Polyurethane materials are a type of synthetic resin with various product forms. They have rich raw material varieties, multiple formula combinations, and a wide range of product forms and application fields. The main product forms include soft and hard foam plastics, elastomers, coatings, adhesives, synthetic leather, waterproof materials, and paving materials. Polyurethane products are widely used in furniture cushions, vehicle seat cushions, and various soft laminated composite cushions. Polyurethane materials are mostly synthesized from petrochemical raw materials and are highly toxic. However, with increasing concerns about future raw material sources and resource scarcity, monomer design based on renewable resources is becoming a demand.

[0003] There are three main methods for synthesizing polyurethane foam materials: one-step method, semi-prepolymer method, and prepolymer method, among which the semi-prepolymer method and prepolymer method are also called two-step method. The one-step method refers to a method in which raw materials such as polyether or polyester polyol, isocyanate, chain extender crosslinker, foaming agent, foam stabilizer, catalyst, etc. are mixed together at one time after metering, and then reacted and cured to obtain a hard foam product. Since most of the one-step foam synthesis is carried out at room temperature, there are more requirements for the raw materials, such as the raw materials must be liquid at room temperature, the raw materials must have high mutual solubility between the components, and there should be no obvious stratification. The semi-prepolymer method refers to a method in which excess isocyanate is first reacted with polyol to form a prepolymer with a high free-NCO content. During the reaction, the prepolymer is mixed with polyol, chain extender crosslinker and other additives to obtain a foam product. The difference between the prepolymer method and the semi-prepolymer method is that in addition to the polyol in the prepolymer, no polyol is added to react, and the prepolymer is directly reacted with the chain extender crosslinker, foaming agent and other additives.

[0004] Polyurethane soft foam is mainly used in furniture and vehicle seat cushions. Since these materials often come into contact with the human body over a large area, they are easily contaminated with sweat and cause microbial growth. At the same time, due to their large size, they are difficult to disassemble and clean, which will cause fading, stains and odor residues, accelerate biodegradation, and ultimately reduce mechanical strength and shorten product life. More importantly, these problems will bring great harm to human health. Therefore, antibacterial and mildew-proof modification of polyurethane soft foam has very important application value.

[0005] The common method of antibacterial modification of polyurethane is to add antibacterial agents to the system and blend them. There are many types of antibacterial agents, which are usually divided into three categories: natural antibacterial agents, inorganic antibacterial agents and organic antibacterial agents. Natural antibacterial agents are restricted by raw materials and processing conditions, while inorganic antibacterial agents and organic antibacterial agents are mostly used in practical applications. Inorganic antibacterial agents are mainly silver-based antibacterial agents, which have the advantages of good safety, heat resistance and durability, but the disadvantages are high price, easy discoloration, slow antibacterial efficiency, poor compatibility with polymer materials, etc. Organic antibacterial agents mainly include quaternary ammonium salts, quaternary phosphate salts, guanidines, phenols, and pyridines. Organic antibacterial agents have the advantages of fast sterilization speed and wide antibacterial range, but they also have problems such as poor heat resistance, easy exudation, and toxicity of dissolved substances.

[0006] At present, the main method for improving the antibacterial property of polyurethane is to add fillers. There is less attention paid to the development of bio-based polyisocyanate monomers, especially aromatic isocyanates. The reason is that the current mature aromatic isocyanate routes mostly involve the use of phosgene, and the acute toxicity of phosgene limits the development of bio-based polyisocyanate monomers. Therefore, how to use the active functional groups on polyether polyols to introduce a variety of antibacterial agents and develop a special polyether polyol for antibacterial polyurethane is important for introducing a variety of antibacterial groups to expand the application range of antibacterial polyurethane; how to prepare aromatic polyisocyanates without using phosgene is of great significance. Summary of the invention

[0007] In order to overcome the shortcomings of the prior art, one of the purposes of the present invention is to provide a method for preparing a polyurethane foam material for a bicycle seat cushion, using the active functional groups on the polyether polyol to introduce a variety of antibacterial agents and prepare aromatic polyisocyanates without using phosgene.

[0008] One of the purposes of the present invention is achieved by the following technical solution:

[0009] A method for preparing a polyurethane foam material for a bicycle seat cushion is disclosed. The polyurethane foam material is prepared by mixing and foaming the following raw materials in parts by weight: 30-35 parts of a new polyisocyanate; 12-16 parts of an antibacterial polyether polyol; 40-50 parts of a polyether polyol; 1-2 parts of a catalyst; 3-5 parts of a blowing agent; 2-4 parts of a cross-linking agent; and 0.5-1.5 parts of a surfactant.

[0010] Furthermore, the preparation method of the antibacterial polyether polyol comprises the following steps: adding a phosphine ligand and an antibacterial agent to a polyether polyol solution, stirring at -3 to 2°C to obtain a mixed solution; adding azodicarboxylic acid ester to the mixed solution, heating to room temperature, reacting for 2 to 5 hours to obtain a reaction solution; purifying the reaction solution to obtain the antibacterial polyether polyol; the antibacterial agent is any one of 4-hydroxyphenylpropionaldehyde, 4-(3-oxo-1-en-1-yl)benzoic acid, and 3-methoxy-4-mercaptobenzaldehyde.

[0011] Furthermore, the molar ratio of the polyether polyol, the phosphine ligand, the antibacterial agent, and the azodicarbonate is 1:(1.2-1.5):1:(1.2-1.5).

[0012] Furthermore, the polyether polyol is one of polyethylene glycol and polypropylene glycol, the phosphine ligand is one of triphenylphosphine and tributylphosphine, and the azodicarboxylic acid ester is one of diisopropyl azodicarboxylate and diethyl azodicarboxylate.

[0013] Furthermore, the polyether polyol solution is a tetrahydrofuran solution of polyether polyol.

[0014] Furthermore, the preparation method of the novel polyisocyanate comprises the following steps:

[0015]

[0016] (1) In the presence of potassium carbonate and iodine salt, hesperidin and bromopropionamide are reacted at 40-50°C for 3-4 hours, and then a strong base is added to the reaction solution, and the reaction is continued at 60-65°C for 3-4 hours to obtain compound 1;

[0017] (2) In the presence of 4-dimethylaminopyridine, compound 1 is reacted with di-tert-butyl dicarbonate for 2 to 3 hours. After the reaction is completed, the reaction solution is purified to obtain the novel polyisocyanate.

[0018] Furthermore, the molar ratio of hesperidin, potassium carbonate, iodide salt, bromopropionamide and strong base is 1: (4.5-6): (0.3-0.5): (3-3.2): (6-10); the molar ratio of compound 1, 4-dimethylaminopyridine and di-tert-butyl dicarbonate is 1: (0.15-0.3): (3-3.5); the iodide salt is one of potassium iodide and sodium iodide, the bromopropionamide is 2-bromopropionamide; the strong base is one of sodium hydroxide and potassium hydroxide.

[0019] Furthermore, the catalyst is a mixture of triethylenediamine and lead acetate; the foaming agent is a mixture of water and dichloromethane; the crosslinking agent is one of glycerol and trimethylolpropane; and the surfactant is an organosilicon surfactant.

[0020] Furthermore, the mass ratio of triethylenediamine to lead acetate is 1:1, and the mass ratio of water to dichloromethane is 3:2.

[0021] A second object of the present invention is to provide a polyurethane foam material for a bicycle seat.

[0022] The second object of the present invention is achieved by adopting the following technical solution:

[0023] A polyurethane foam material for a bicycle seat cushion is prepared according to the preparation method.

[0024] The third object of the present invention is to provide a polyurethane foam material for bicycle seat cushions for use in the field of bicycle seat cushions.

[0025] The third object of the present invention is achieved by adopting the following technical solution:

[0026] The invention discloses an application of a polyurethane foam material for a bicycle seat in the field of bicycle seat.

[0027] Compared with the prior art, the present invention has the following beneficial effects:

[0028] 1. The present invention adopts green chemistry to prepare a novel polyisocyanate containing three isocyanate groups, and also grafts three different antibacterial agents on polyether polyols, and then polycondenses the novel polyisocyanate, antibacterial polyether polyols and conventional polyether polyols to prepare a polyurethane foam material with antibacterial properties, which provides a new synthetic idea for the preparation of antibacterial polyurethane.

[0029] 2. The preparation process of the present invention reduces the use of toxic raw materials and reduces pollutant emissions, which meets the requirements of green chemistry. In addition, the polyurethane foam material prepared by the present invention has a high antibacterial rate and its mechanical properties are not significantly affected. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 The present invention provides a novel polyisocyanate preparation route;

[0031] Figure 2 The preparation route of the antibacterial polyether polyol of Example 1 of the present invention;

[0032] Figure 3 The preparation route of the antibacterial polyether polyol of Example 2 of the present invention;

[0033] Figure 4 This is the preparation route of the antibacterial polyether polyol of Example 3 of the present invention. DETAILED DESCRIPTION

[0034] Below, in conjunction with the accompanying drawings and specific embodiments, the present invention is further described. It should be noted that, under the premise of no conflict, the embodiments described below or the technical features can be arbitrarily combined to form new embodiments. The specific conditions not specified in the embodiments are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used, unless otherwise specified, are conventional products obtained through commercial channels.

[0035] Example 1

[0036] A method for preparing a polyurethane foam material for a bicycle seat cushion, which is made from the following materials in parts by weight: 35 parts of a new polyisocyanate; 14 parts of an antibacterial polyether polyol; 41 parts of polyethylene glycol 400; 1 part of a catalyst; 5 parts of a foaming agent; 3 parts of a cross-linking agent; and 1 part of a surfactant. Specifically, the following steps are included:

[0037] (1) Preparation of new polyisocyanates

[0038] The preparation route of the novel polyisocyanate of the present invention is as follows Figure 1 As shown, the specific steps are:

[0039] Take 1g of hesperidin (1eq) and place it in a reaction bottle containing 8mL of N,N-dimethylacetamide (DMAC), then add potassium carbonate (4.5eq), potassium iodide (0.3eq), and 2-bromopropionamide (3eq) in sequence, stir evenly at room temperature, and then heat to 40°C for 6h; after TLC detection of hesperidin reaction is complete, cool the reaction solution to room temperature, add potassium hydroxide (6eq) to the reaction solution, and heat to 65°C at the same time, and continue stirring for 1.5h; then add 8mL of water to the reaction system, and continue stirring the reaction solution under reflux for 1.5h. Add 16mL of water to stop heating, let the reaction solution gradually cool to room temperature, filter the reaction solution, collect the filter cake and dry it to obtain compound 1;

[0040] 1 g of compound 1 (1 eq) was placed in a reaction bottle containing 8 mL of acetonitrile, and 4-dimethylaminopyridine (DMAP, 0.15 eq) and di-tert-butyl dicarbonate (Boc2O, 3.3 eq) were added in sequence, and the reaction was carried out at room temperature for 2 h. After TLC detected that the reaction of compound 1 was complete, the reaction solution was cooled to room temperature, and the reaction solution was concentrated and separated by column chromatography (the eluent was n-heptane: ethyl acetate = 8:2) to obtain a new polyisocyanate.

[0041] The novel polyisocyanate 1 The HNMR results are: 1HNMR (400MHz, DMSO-d6) δ: 7.30 (m, 2H), 7.01 (d, 1H), 6.85 (d, 1H), 6.71 (d, 1H), 5.53 (t, 1H), 4.05 (s, 3H), 3.25 (m, 2H).

[0042] (2) Preparation of antibacterial polyether polyols

[0043] The preparation route of antibacterial polyether polyols is as follows Figure 2 As shown, the specific steps are:

[0044] Take 1g of polyethylene glycol 400 (1eq) and dilute it with 5mL of tetrahydrofuran, then add triphenylphosphine (1.2eq) and 3-methoxy-4-mercaptobenzaldehyde (1eq) to the polyethylene glycol solution in sequence, mix well to obtain a reaction solution; then cool the reaction solution to 0°C, and then add diisopropyl azodicarboxylate (DIAD, 1.2eq) dropwise to the reaction solution, react at 0°C for 5 minutes, then gradually raise the temperature to 25°C (remove the cooling bath and naturally raise to room temperature) and react for 2 hours; after the reaction solution is detected by TLC plate and shows that the polyethylene glycol reaction is complete, the reaction solution is subjected to negative pressure distillation to separate the raw material and the product to obtain an antibacterial polyether polyol.

[0045] (3) Preparation of polyurethane foam material

[0046] By weight, 35 parts of novel polyisocyanate, 14 parts of antibacterial polyether polyol and 21 parts of polyethylene glycol 400 were charged into a reaction bottle and mixed to obtain material A; the remaining 20 parts of polyethylene glycol 400, 0.5 parts of triethylenediamine, 0.5 parts of lead acetate, 3 parts of water, 2 parts of dichloromethane, 3 parts of glycerol and 1 part of Silstab 2000 siltech silicone surfactant in the formula were mixed as material B; material A and material B were mixed, stirred evenly and foamed at 25° C. The stirrer speed was 1500 r / min and the mixture was allowed to stand for 5 minutes. The obtained product was a polyurethane foam material.

[0047] Example 2

[0048] A method for preparing a polyurethane foam material for a bicycle seat cushion, which is made from the following materials in parts by weight: 30 parts of a new polyisocyanate; 12 parts of an antibacterial polyether polyol; 48 parts of polypropylene glycol 500; 1.8 parts of a catalyst; 3.5 parts of a foaming agent; 3.2 parts of a cross-linking agent; and 1.5 parts of a surfactant. Specifically, the following steps are included:

[0049] (1) Preparation of new polyisocyanates

[0050] Take 1g of hesperidin (1eq) and place it in a reaction bottle containing 5mL of N,N-dimethylacetamide (DMAC), then add potassium carbonate (6eq), potassium iodide (0.5eq), and 2-bromopropionamide (3.2eq) in sequence, stir evenly at room temperature, and then heat to 50℃ for 3h; after TLC detection of hesperidin reaction is complete, cool the reaction solution to room temperature, add potassium hydroxide (10eq) to the reaction solution, and heat to 60℃ and continue stirring for 2h; then add 5mL of water to the reaction system, and continue stirring the reaction solution under reflux for 1h. Add 10mL of water to stop heating, let the reaction solution gradually cool to room temperature, filter the reaction solution, collect the filter cake and dry it to obtain compound 1;

[0051] 1g of compound 1 (1eq) was placed in a reaction bottle containing 10mL of acetonitrile, and then 4-dimethylaminopyridine (DMAP, 0.3eq) and di-tert-butyl dicarbonate (Boc2O, 3.5eq) were added in sequence, and the reaction was carried out at room temperature for 2h; after TLC detection of compound 1, the reaction solution was cooled to room temperature, and the reaction solution was concentrated and separated by column chromatography (eluent was n-heptane: ethyl acetate = 8:2) to obtain a novel polyisocyanate. The novel polyisocyanate 1 The HNMR results were consistent with those in Example 1.

[0052] (2) Preparation of antibacterial polyether polyols

[0053] The preparation route of antibacterial polyether polyols is as follows Figure 3 As shown, the specific preparation steps are:

[0054] Take 1g of polypropylene glycol 500 (1eq) and dilute it with 8mL of tetrahydrofuran, then add tributyl phosphine (1.5eq) and 4-hydroxyphenylpropionaldehyde (1eq) to the polypropylene glycol 500 solution in sequence, mix well to obtain a reaction solution; then cool the reaction solution to 2°C, and then add diisopropyl azodicarboxylate (DIAD, 1.5eq) dropwise to the reaction solution, react at 2°C for 5 minutes, then gradually raise the temperature to 25°C (remove the cooling bath and naturally raise to room temperature) and react for 3 hours; after the reaction solution is detected by TLC plate and shows that the polyethylene glycol reaction is complete, the reaction solution is subjected to negative pressure distillation to separate the raw material and the product to obtain an antibacterial polyether polyol.

[0055] (3) Preparation of polyurethane foam material

[0056] By weight, 30 parts of novel polyisocyanate, 12 parts of antibacterial polyether polyol, and 18 parts of polypropylene glycol 500 are charged into a reaction bottle and mixed to obtain material A; the remaining 30 parts of polypropylene glycol 500, 0.9 parts of triethylenediamine, 0.9 parts of lead acetate, 2.1 parts of water, 1.4 parts of dichloromethane, 3.2 parts of trimethylolpropane, and 1.5 parts of Silstab 2000 siltech silicone surfactant in the formula are used as material B; material A and material B are mixed and stirred evenly, and foamed at 22°C with a stirrer speed of 1700 r / min. The mixture is allowed to stand for 8 minutes, and the resulting product is a polyurethane foam material.

[0057] Example 3

[0058] A method for preparing a polyurethane foam material for a bicycle seat cushion, which is made from the following materials in parts by weight: 32 parts of a new polyisocyanate; 12.8 parts of an antibacterial polyether polyol; 45.2 parts of polypropylene glycol 500; 2 parts of a catalyst; 4 parts of a foaming agent; 2 parts of a cross-linking agent; and 1 part of a surfactant. Specifically, the following steps are included:

[0059] (1) Preparation of new polyisocyanates

[0060] Take 1g of hesperidin (1eq) and place it in a reaction bottle containing 12mL of N,N-dimethylacetamide (DMAC), then add potassium carbonate (5eq), potassium iodide (0.5eq), and 2-bromopropionamide (3.1eq) in sequence, stir evenly at room temperature, and then heat to 40°C for 4h; after TLC detection of hesperidin reaction is complete, cool the reaction solution to room temperature, add sodium hydroxide (6eq) to the reaction solution, and heat to 65°C at the same time, and continue stirring for 2h; then add 10mL of water to the reaction system, and continue stirring the reaction solution under reflux for 2h. Add 16mL of water to stop heating, let the reaction solution gradually cool to room temperature, filter the reaction solution, collect the filter cake and dry it to obtain compound 1;

[0061] 1g of compound 1 (1eq) was placed in a reaction bottle containing 8mL of acetonitrile, and then 4-dimethylaminopyridine (DMAP, 0.2eq) and di-tert-butyl dicarbonate (Boc2O, 3eq) were added in sequence, and the reaction was carried out at room temperature for 3h; after TLC detection of the complete reaction of compound 1, the reaction solution was cooled to room temperature, and the reaction solution was concentrated and separated by column chromatography (the eluent was n-heptane: ethyl acetate = 8:2) to obtain a novel polyisocyanate. The novel polyisocyanate 1 The HNMR results were consistent with those in Example 1.

[0062] (2) Preparation of antibacterial polyether polyols

[0063] The preparation route of antibacterial polyether polyols is as follows Figure 4 As shown, the specific preparation steps are:

[0064] Take 1g of polyethylene glycol 400 (1eq) and dilute it with 10mL of tetrahydrofuran, then add triphenylphosphine (1.3eq) and 4-(3-oxo-1-en-1-yl)benzoic acid (1eq) to the polyethylene glycol solution in sequence, mix well to obtain a reaction solution; then cool the reaction solution to -3°C, and then add diethyl azodicarboxylate (DEAD, 1.3eq) dropwise to the reaction solution, react at -3°C for 5 minutes, then gradually raise the temperature to 25°C (remove the cooling bath and naturally raise to room temperature) and react for 2 hours; after the reaction solution is detected by TLC plate and shows that the polyethylene glycol reaction is complete, the reaction solution is subjected to negative pressure distillation to separate the raw material and the product to obtain an antibacterial polyether polyol.

[0065] (3) Preparation of polyurethane foam material

[0066] By weight, 32 parts of novel polyisocyanate, 12.8 parts of antibacterial polyether polyol and 19.2 parts of polypropylene glycol 500 were charged into a reaction bottle and mixed to obtain material A; the remaining 26 parts of polypropylene glycol 500, 1 part of triethylene diamine, 1 part of lead acetate, 2.4 parts of water, 1.6 parts of dichloromethane, 2 parts of glycerol and 1 part of Silstab 2000 siltech silicone surfactant in the formula were used as material B; material A and material B were mixed and stirred evenly, and foamed at 27°C with a stirrer speed of 1800 r / min. The mixture was allowed to stand for 10 minutes, and the obtained product was a polyurethane foam material.

[0067] Comparative Example 1

[0068] A novel polyurethane foam material is basically the same as Example 1, except that the antibacterial polyether polyol is replaced by polyethylene glycol 400.

[0069] Comparative Example 2

[0070] A method for preparing an antibacterial polyurethane foam material is basically the same as that of Example 1, except that the novel polyisocyanate is replaced by 4,4'-methylenebis(phenyl isocyanate).

[0071] Comparative Example 3

[0072] A method for preparing a composite antibacterial polyurethane foam material is basically the same as that of Example 1, except that step (2) is omitted, and the antibacterial polyether polyol is replaced by a mixture of 3-methoxy-4-mercaptobenzaldehyde and polyethylene glycol 400, that is, a novel polyisocyanate, 3-methoxy-4-mercaptobenzaldehyde and polyethylene glycol 400 are mixed to obtain material A.

[0073] Test Example 1

[0074] The performance test results of the products of Examples 1 to 3 and Comparative Examples 1 to 3 are summarized in Table 1, wherein the antibacterial performance test refers to GB / T 20944.3-2008 "Evaluation of antibacterial properties of textiles Part 3: Oscillation method", the tensile strength test refers to GB / T 6344-2008 "Determination of tensile strength and elongation at break of flexible foam polymeric materials", the tear strength test refers to GB / T 10808-2006 "Determination of tear strength of polymer porous elastic materials", the rebound rate test refers to GB / T 6670-2008 "Determination of rebound properties of flexible foam polymeric materials by falling ball method", and the depression hardness performance test (load at 65% depression) refers to GB / T 10807-2006 "Determination of hardness of flexible foam polymeric materials (depression method)".

[0075] Table 1

[0076]

[0077] It can be seen from Table 1 that the polyurethane foam materials prepared in Examples 1 to 3 have a high antibacterial rate and have no obvious effect on the density of polyurethane and mechanical properties such as tensile strength, tear strength, rebound rate, and 65% indentation load; the antibacterial performance of the antibacterial polyurethane foam material prepared in Comparative Example 2 is weaker than that of the polyurethane foam material prepared in Example 1, which proves that the new polyisocyanate used to prepare the polyurethane foam material in Example 1 is grafted with more antibacterial groups, and its ability to carry antibacterial groups is higher than that of 4,4'-methylenebis(phenyl isocyanate).

[0078] Test Example 2

[0079] The polyurethane foam material prepared in Example 1 and the composite antibacterial polyurethane foam material prepared in Comparative Example 3 with equal surface areas were immersed in a mixed solvent (the volume ratio of water, ethanol and acetic acid was 1:1:1), and placed in a constant temperature box at 37°C. The polyurethane foam material prepared in Example 1 and the composite antibacterial polyurethane foam material prepared in Comparative Example 3 were taken out at time points of 0d, 1d, 5d, 7d, 10d, 15d, and 30d, respectively, and the antibacterial rate was determined according to the antibacterial rate test method in Test Example 1. The results are shown in Table 2.

[0080] Table 2

[0081]

[0082] As can be seen from Table 2, the polyurethane foam material prepared in Example 1 still maintains an antibacterial rate of 99% after one week in an environment simulating common solvents, and the antibacterial rate only slightly decreases on the 10th day, but still maintains an antibacterial rate of 98%. The antibacterial polyurethane foam material prepared in Comparative Example 3 has an antibacterial rate of 99% at the beginning, but the antibacterial rate is lower than 50% on the 5th day, and has no antibacterial performance on the 15th day, which proves that the polyurethane foam material grafted with antibacterial groups has excellent long-term antibacterial performance.

[0083] The above-mentioned embodiments are only preferred embodiments of the present invention and cannot be used to limit the scope of protection of the present invention. Any non-substantial changes and substitutions made by technicians in this field on the basis of the present invention shall fall within the scope of protection required by the present invention.

Claims

1. A method for preparing a polyurethane foam material for a bicycle seat cushion, characterized in that: The polyisocyanate is prepared by mixing and foaming the following raw materials in parts by weight: 30-35 parts of polyisocyanate; 12-16 parts of antibacterial polyether polyol; 40-50 parts of polyether polyol; 1-2 parts of catalyst; 3-5 parts of foaming agent; 2-4 parts of cross-linking agent; 0.5-1.5 parts of surfactant. The preparation method of the polyisocyanate comprises the following steps: (1) In the presence of potassium carbonate and iodine salt, hesperidin and bromopropionamide are reacted at 40-50° C. for 3-4 hours, and then a strong base is added to the reaction solution and the reaction is continued at 60-65° C. for 3-4 hours to obtain compound 1; the strong base is one of sodium hydroxide and potassium hydroxide; (2) In the presence of 4-dimethylaminopyridine, compound 1 is reacted with di-tert-butyl dicarbonate for 2 to 3 hours. After the reaction is completed, the reaction solution is purified to obtain the polyisocyanate.

2. The method for preparing the polyurethane foam material for bicycle seat cushion according to claim 1, characterized in that: The preparation method of the antibacterial polyether polyol comprises the following steps: adding a phosphine ligand and an antibacterial agent to a polyether polyol solution, stirring at -3 to 2°C to obtain a mixed solution; adding azodicarboxylic acid ester to the mixed solution, heating to room temperature, reacting for 2 to 5 hours to obtain a reaction solution; purifying the reaction solution to obtain the antibacterial polyether polyol; the antibacterial agent is any one of 4-hydroxyphenylpropionaldehyde, 4-(3-oxo-1-en-1-yl)benzoic acid, and 3-methoxy-4-mercaptobenzaldehyde.

3. The method for preparing the polyurethane foam material for bicycle seat cushion according to claim 2, characterized in that: The molar ratio of the polyether polyol, the phosphine ligand, the antibacterial agent and the azodicarbonate is 1:(1.2-1.5):1:(1.2-1.5).

4. The method for preparing the polyurethane foam material for bicycle seat cushion according to claim 3, characterized in that: The polyether polyol is one of polyethylene glycol and polypropylene glycol, the phosphine ligand is one of triphenylphosphine and tributylphosphine, and the azodicarboxylic acid ester is one of diisopropyl azodicarboxylate and diethyl azodicarboxylate.

5. The method for preparing the polyurethane foam material for bicycle seat cushion according to claim 1, characterized in that: The molar ratio of hesperidin, potassium carbonate, iodide salt, bromopropionamide and strong base is 1: (4.5-6): (0.3-0.5): (3-3.2): (6-10); the molar ratio of compound 1, 4-dimethylaminopyridine and di-tert-butyl dicarbonate is 1: (0.15-0.3): (3-3.5); the iodide salt is one of potassium iodide and sodium iodide, and the bromopropionamide is 2-bromopropionamide.

6. The method for preparing the polyurethane foam material for bicycle seat cushion according to claim 1, characterized in that: The catalyst is a mixture of triethylenediamine and lead acetate; the foaming agent is a mixture of water and dichloromethane; the crosslinking agent is one of glycerol and trimethylolpropane; and the surfactant is an organic silicon surfactant.

7. The method for preparing the polyurethane foam material for bicycle seat cushion according to claim 6, characterized in that: The mass ratio of the triethylenediamine to lead acetate is 1:1, and the mass ratio of the water to dichloromethane is 3:

2.

8. The polyurethane foam material for bicycle seat prepared according to the preparation method according to any one of claims 1 to 7.

9. Application of the polyurethane foam material for bicycle seat according to claim 8 in the field of bicycle seat.

Citation Information

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