CN114456387A - Silicone oil for waterproof and weather-resistant shoe material and preparation method thereof - Google Patents

Silicone oil for waterproof and weather-resistant shoe material and preparation method thereof Download PDF

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Publication number
CN114456387A
CN114456387A CN202111646122.4A CN202111646122A CN114456387A CN 114456387 A CN114456387 A CN 114456387A CN 202111646122 A CN202111646122 A CN 202111646122A CN 114456387 A CN114456387 A CN 114456387A
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silicone oil
hydrogen
preparation
weather
waterproof
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李光
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Nantong Hengguangda Polyurethane Material Co ltd
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Nantong Hengguangda Polyurethane Material Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • A—HUMAN NECESSITIES
    • A43—FOOTWEAR
    • A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
    • A43B1/00—Footwear characterised by the material
    • A43B1/14—Footwear characterised by the material made of plastics
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)

Abstract

The application relates to waterproof and weather-resistant silicone oil for shoe materials, which is prepared from the following raw materials: the preparation method of the hydrogen-containing silicone oil, the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, the catalyst and the isopropanol comprises the following steps: s1, drying allyl-terminated polyoxyethylene polyoxypropylene epoxy ether by using anhydrous sodium sulfate; s2, placing hydrogen-containing silicone oil into a container, and adding allyl-terminated polyoxyethylene polyoxypropylene epoxy ether and isopropanol; s3, connecting N2Exhausting air, stirring to mix uniformly, heating, adding catalyst to start reaction; and S4, decompressing and desolventizing after the reaction is finished, and filtering to obtain a silicone oil product. The application adopts the formula and adopts the methodThe prepared silicone oil product is applied to the production of polyurethane shoe materials, and is beneficial to improving the weather resistance of the polyurethane shoe materials.

Description

Silicone oil for waterproof and weather-resistant shoe material and preparation method thereof
Technical Field
The application relates to the technical field of processing aids, in particular to silicone oil for waterproof and weather-resistant shoe materials and a preparation method thereof.
Background
Compared with common rubber shoe materials, the polyurethane shoe material has the characteristics of light weight, good wear resistance and the like. The polyurethane shoe material is prepared by taking polyurethane resin as a main raw material, and in the preparation process, silicone oil is usually added to improve the physical and chemical properties of the polyurethane shoe material, wherein the silicone oil is used for the polyurethane shoe material.
The silicone oil for polyurethane shoe materials is mainly used as a surfactant and generally has the functions of lubrication, adhesion resistance, high temperature resistance, oxidation resistance and the like. The commonly used silicone oil for polyurethane shoe materials in the market is usually methyl silicone oil, and because the shoe materials are greatly influenced by the environment outdoors, the weather resistance requirement on the shoe materials is usually higher, but the improvement effect of the addition of the methyl silicone oil on the weather resistance of the polyurethane shoe materials is limited.
There is a need for a silicone oil product with good weatherability for improving the weatherability of polyurethane shoe materials prepared therefrom.
Disclosure of Invention
In order to improve the weather resistance of the silicone oil, the application provides the silicone oil for the waterproof and weather-resistant shoe material and the preparation method thereof.
In a first aspect, the application provides a waterproof and weather-resistant silicone oil for shoe materials, which adopts the following technical scheme:
the silicone oil for the waterproof and weather-resistant shoe material is prepared from the following raw materials: hydrogen-containing silicone oil, allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, a catalyst and isopropanol.
In a second aspect, the application provides a preparation method of silicone oil for waterproof and weather-resistant shoe materials, which adopts the following technical scheme:
a preparation method of silicone oil for waterproof and weather-resistant shoe materials comprises the following steps:
s1, drying allyl-terminated polyoxyethylene polyoxypropylene epoxy ether by using anhydrous sodium sulfate;
s2, placing hydrogen-containing silicone oil into a container, and adding allyl-terminated polyoxyethylene polyoxypropylene epoxy ether and isopropanol;
s3, connecting N2Exhausting air, stirring to mix uniformly, heating, adding catalyst and starting reaction;
and S4, decompressing and desolventizing after the reaction is finished, and filtering to obtain a silicone oil product.
Preferably, the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is (1-1.4): 1.
preferably, the reaction temperature is 80-100 ℃, and the reaction time is 5.2-5.8 h.
Preferably, the catalyst is chloroplatinic acid, and the using amount is 30-40 mu g/g.
Preferably, the isopropanol is used in an amount of 35-45 wt%.
Preferably, before the hydrogen-containing silicone oil is put into preparation, the hydrogen-containing silicone oil is modified, and the modification method comprises the following steps: 1) mixing the heptafluorobutyl methacrylate and the dimethylbenzene with the catalyst uniformly at room temperature; 2) slowly dripping hydrogen-containing silicone oil, wherein the dripping time is controlled to be 30-40 min; 3) and heating the system to 40-60 ℃, reacting for 2.5-3.5 h at constant temperature, and distilling under reduced pressure to obtain the modified hydrogen-containing silicone oil.
Preferably, the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: (1-1.3).
Preferably, the catalyst is cuprous bromide, and the using amount is 10-20 mg/g.
Preferably, the amount of the xylene is 30-40 wt%.
In summary, the present application has the following beneficial effects:
1. according to the preparation method, the epoxy group in the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether is adopted to replace the hydrogen terminal group of the hydrogen-containing silicone oil to prepare the epoxy-terminated silicone oil, the epoxy group has excellent tolerance, and the toughening of the silicone oil and the improvement of the weather resistance of the silicone oil are facilitated, so that the weather resistance of the polyurethane shoe material prepared by using the silicone oil is improved.
2. The polyoxyethylene group and the polyoxypropylene group in the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether have good hydrophobic performance, and the groups are blocked to the main chain segment of the hydrogen-containing silicone oil, so that the hydrophobicity of the hydrogen-containing silicone oil is favorably improved, and the hydrophobicity of the polyurethane shoe material prepared by the hydrogen-containing silicone oil is improved.
3. According to the preparation method, before the hydrogen-containing silicone oil is terminated, heptafluorobutyl methacrylate is used for modifying, the fluoroalkyl block is added into the chain segment of the hydrogen-containing silicone oil, so that the hydrophobicity of the silicone oil is further improved, and the carbon-carbon double bond block is favorable for improving the structural stability and the weather resistance of the silicone oil, so that the water resistance and the weather resistance of the polyurethane shoe material prepared by the silicone oil are further improved.
Detailed Description
The raw materials used in the application are all purchased from the market.
Allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, n (EO)/n (PO) =2/3, molar mass 1000 g/mol.
The present application will be described in further detail with reference to examples.
Examples
Example 1
The silicone oil for the waterproof and weather-resistant shoe material is prepared from the following raw materials: hydrogen-containing silicone oil, allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, a catalyst and isopropanol.
The preparation method of the silicone oil specifically comprises the following steps:
s1, drying allyl-terminated polyoxyethylene polyoxypropylene epoxy ether by using 3wt% of anhydrous sodium sulfate;
s2, placing hydrogen-containing silicone oil into a three-neck flask provided with a reflux condenser pipe, a thermometer and a stirrer, and adding allyl-terminated polyoxyethylene polyoxypropylene epoxy ether and isopropanol;
wherein the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is 1: 1, the using amount of the isopropanol is 35 wt%;
s3, connecting N2Exhausting air, stirring to mix uniformly, heating, adding chloroplatinic acid with the dosage of 30 mu g/g, and starting to react at the reaction temperature of 80 ℃ for 5.2 h;
and S4, after the reaction is finished, reducing the pressure to remove the isopropanol, and filtering to obtain a silicone oil product.
Before the hydrogen-containing silicone oil is put into preparation, the hydrogen-containing silicone oil is modified, and the modification method comprises the following steps:
1) uniformly mixing heptafluorobutyl methacrylate, dimethylbenzene and cuprous bromide at room temperature, wherein the dosage of the cuprous bromide is 10mg/g, and the dosage of the dimethylbenzene is 30 wt%;
2) slowly dropwise adding hydrogen-containing silicone oil, wherein the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: 1, controlling the dripping time to be 30 min;
3) and (3) heating the system to 40 ℃, reacting at a constant temperature for 2.5 hours, and after the reaction is finished, distilling under reduced pressure to remove xylene to obtain the modified hydrogen-containing silicone oil.
Example 2
The silicone oil for the waterproof and weather-resistant shoe material is prepared from the following raw materials: hydrogen-containing silicone oil, allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, a catalyst and isopropanol.
The preparation method of the silicone oil specifically comprises the following steps:
s1, drying allyl-terminated polyoxyethylene polyoxypropylene epoxy ether by using 3wt% of anhydrous sodium sulfate;
s2, placing hydrogen-containing silicone oil into a three-neck flask provided with a reflux condenser pipe, a thermometer and a stirrer, and adding allyl-terminated polyoxyethylene polyoxypropylene epoxy ether and isopropanol;
wherein the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is 1.2: 1, the using amount of the isopropanol is 40 wt%;
s3, connecting N2Exhausting air, stirring to mix uniformly, heating, adding chloroplatinic acid with the dosage of 35 mu g/g, and starting to react at the reaction temperature of 90 ℃ for 5.6 h;
and S4, after the reaction is finished, reducing the pressure to remove the isopropanol, and filtering to obtain a silicone oil product.
Before the hydrogen-containing silicone oil is put into preparation, the hydrogen-containing silicone oil is modified, and the modification method comprises the following steps:
1) uniformly mixing heptafluorobutyl methacrylate, xylene and cuprous bromide at room temperature, wherein the dosage of the cuprous bromide is 15mg/g, and the dosage of the xylene is 35 wt%;
2) slowly dropwise adding hydrogen-containing silicone oil, wherein the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: 1.15, the dripping time is controlled to be 35 min;
3) and (3) heating the system to 50 ℃, reacting for 3 hours at constant temperature, and after the reaction is finished, distilling under reduced pressure to remove xylene to obtain the modified hydrogen-containing silicone oil.
Example 3
The silicone oil for the waterproof and weather-resistant shoe material is prepared from the following raw materials: hydrogen-containing silicone oil, allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, a catalyst and isopropanol.
The preparation method of the silicone oil specifically comprises the following steps:
s1, drying allyl-terminated polyoxyethylene polyoxypropylene epoxy ether by using 3wt% of anhydrous sodium sulfate;
s2, placing hydrogen-containing silicone oil into a three-neck flask provided with a reflux condenser pipe, a thermometer and a stirrer, and adding allyl-terminated polyoxyethylene polyoxypropylene epoxy ether and isopropanol;
wherein the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is 1.4: 1, the using amount of the isopropanol is 45 wt%;
s3, connecting N2Exhausting air, stirring to mix uniformly, heating, adding chloroplatinic acid with the dosage of 40 mu g/g, and starting to react at the reaction temperature of 100 ℃ for 5.8 h;
and S4, after the reaction is finished, reducing the pressure to remove the isopropanol, and filtering to obtain a silicone oil product.
Before the hydrogen-containing silicone oil is put into preparation, the hydrogen-containing silicone oil is modified, and the modification method comprises the following steps:
1) uniformly mixing heptafluorobutyl methacrylate, xylene and cuprous bromide at room temperature, wherein the dosage of the cuprous bromide is 20mg/g, and the dosage of the xylene is 40 wt%;
2) slowly dropwise adding hydrogen-containing silicone oil, wherein the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: 1.3, controlling the dripping time to be 40 min;
3) and (3) heating the system to 60 ℃, reacting at constant temperature for 3.5h, and after the reaction is finished, distilling under reduced pressure to remove xylene to obtain the modified hydrogen-containing silicone oil.
Example 4 differs from example 2 in that:
the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is 1: 1.
example 5 differs from example 2 in that:
the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is 1.4: 1.
example 6 differs from example 2 in that:
in the preparation process of the silicone oil, the reaction temperature is 80 ℃.
Example 7 differs from example 2 in that:
in the preparation process of the silicone oil, the reaction temperature is 100 ℃.
Example 8, the difference from example 2 is that:
in the preparation process of the silicone oil, the reaction time is 5.2 h.
Example 9, the difference from example 2 is that:
in the preparation process of the silicone oil, the reaction time is 5.8 h.
Example 10, the difference from example 2 is that:
the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: 1.
example 11 differs from example 2 in that:
the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: 1.3.
example 12 differs from example 2 in that:
in the modification process of the hydrogen-containing silicone oil, the temperature of the system is raised to 40 ℃.
Example 13 differs from example 2 in that:
in the modification process of the hydrogen-containing silicone oil, the temperature of the system is raised to 60 ℃.
Example 14, which differs from example 2 in that:
and in the process of modifying the hydrogen-containing silicone oil, reacting for 2.5 hours at constant temperature.
Example 15 differs from example 2 in that:
and in the process of modifying the hydrogen-containing silicone oil, reacting for 3.5 hours at constant temperature.
Example 16, which differs from example 2 in that:
the hydrogen-containing silicone oil is not modified.
Comparative example
Comparative example 1
The hydrogen-containing silicone oil is used for preparing the polyurethane shoe material.
Comparative example 2, which differs from example 2 in that:
the silicone oil is prepared using an epoxy-free capped allyl polyether.
Comparative example 3, which differs from example 2 in that:
silicone oils were prepared using capped allyl polyethers without polyoxyethylene polyoxypropylene groups.
Performance test
Using the silicone oils prepared in examples 1 to 16 and comparative examples 1 to 3, test pieces for polyurethane shoe materials were prepared, and the test pieces were subjected to the following property test tests.
1. Weather resistance test
The tensile strength and tear strength of the material were measured using an Instron4201 tensile tester in accordance with GB/T531-76 and CBl681-82, and the test pieces were subjected to weathering resistance in accordance with GB/T14835-93, and comparative data on the physical and mechanical properties of the test pieces after exposure to strong sunlight were recorded in Table 1.
TABLE 1 comparative data of physical and mechanical Properties of test pieces
Figure 380871DEST_PATH_IMAGE001
2. Hydrophobicity test
The hydrophobicity of the polyurethane shoe material is tested by adopting a water wetting method, the wetting degree of liquid to solid is generally represented by the size of a contact angle between liquid and solid, the larger the contact angle is, the lower the corresponding solid surface energy is, the better the hydrophobicity and the oleophobicity are, and the test data are recorded in table 2.
TABLE 2 hydrophobicity test data for Silicone oils
Figure 336189DEST_PATH_IMAGE002
By combining examples 1-3 and examples 4-5 and table 1, it can be seen that the dosage ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil affects the quality of the silicone oil, and the dosage ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is controlled to be within a proper range, so that the silicone oil has better weather resistance, and when the silicone oil is applied to polyurethane shoe materials, the weather resistance of the polyurethane shoe materials is favorably improved.
Combining examples 1-3 with examples 6-9 and combining table 1, it can be seen that the reaction temperature and reaction time affect the weatherability of the silicone oil when the silicone oil is prepared, and therefore, adjusting the reaction time and reaction temperature in the appropriate range is a lot of creative work of the inventor, thereby obtaining a silicone oil product with high weatherability.
By combining examples 1-3 and examples 10-11 and table 1, it can be seen that the feeding ratio of heptafluorobutyl methacrylate to hydrogen-containing silicone oil affects the quality of the silicone oil, and the feeding ratio of heptafluorobutyl methacrylate to hydrogen-containing silicone oil is controlled to be in a proper range, so that the silicone oil has better weather resistance, and when the silicone oil is applied to polyurethane shoe materials, the weather resistance of the polyurethane shoe materials is favorably improved.
Combining examples 1-3 with examples 12-15 and combining table 1, it can be seen that the reaction temperature and reaction time affect the weatherability of the silicone oil when the silicone oil is modified, and therefore, adjusting the reaction time and reaction temperature in the appropriate range is a lot of creative work of the inventor, thereby obtaining a silicone oil product with high weatherability.
By combining examples 1 to 3 and example 16 with tables 1 and 2, it can be seen that the hydrophobic property of the silicone oil is significantly reduced without modification treatment of the silicone oil, which indicates that the modification treatment is beneficial to improving the hydrophobic property of the silicone oil, thereby improving the waterproofness of the polyurethane shoe material.
Combining examples 1-3 with comparative example 1 and combining tables 1 and 2, it can be seen that the polyurethane shoe material produced by using only hydrogen-containing silicone oil has poor hydrophobicity and weather resistance, and conversely, the silicone oil prepared by the present application has excellent weather resistance and hydrophobicity.
By combining examples 1-3 with comparative example 2 and combining tables 1 and 2, it can be seen that the weather resistance of the silicone oil prepared by using the epoxy-free terminated allyl polyether is obviously reduced, which indicates that the replacement of the hydrogen terminal group by the epoxy group has the effect of improving the weather resistance of the silicone oil.
As can be seen by combining examples 1-3 with comparative example 3 and by combining tables 1 and 2, the hydrophobicity and weather resistance of the silicone oil prepared by using the capped allyl polyether without polyoxyethylene polyoxypropylene group are remarkably reduced, which shows that the polyoxyethylene polyoxypropylene group has a positive effect on the improvement of the hydrophobicity and weather resistance of the silicone oil.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.

Claims (10)

1. The silicone oil for the waterproof and weather-resistant shoe material is characterized in that: the feed is prepared from the following raw materials: hydrogen-containing silicone oil, allyl-terminated polyoxyethylene polyoxypropylene epoxy ether, a catalyst and isopropanol.
2. A method for preparing the silicone oil for the waterproof and weather-resistant shoe material according to claim 1, which is characterized in that: the method specifically comprises the following steps:
s1, drying allyl-terminated polyoxyethylene polyoxypropylene epoxy ether by using anhydrous sodium sulfate;
s2, placing hydrogen-containing silicone oil into a container, and adding allyl-terminated polyoxyethylene polyoxypropylene epoxy ether and isopropanol;
s3, connecting N2Exhausting air, stirring to mix uniformly, heating, adding catalyst and starting reaction;
and S4, decompressing and desolventizing after the reaction is finished, and filtering to obtain a silicone oil product.
3. The preparation method of the silicone oil for the waterproof and weather-resistant shoe material according to claim 2, wherein the preparation method comprises the following steps: the feeding ratio of the allyl-terminated polyoxyethylene polyoxypropylene epoxy ether to the hydrogen-containing silicone oil is (1-1.4): 1.
4. the preparation method of the silicone oil for the waterproof and weather-resistant shoe material according to claim 2, wherein the preparation method comprises the following steps: the reaction temperature is 80-100 ℃, and the reaction time is 5.2-5.8 h.
5. The preparation method of the silicone oil for the waterproof and weather-resistant shoe material according to claim 2, wherein the preparation method comprises the following steps: the catalyst is chloroplatinic acid, and the using amount is 30-40 mu g/g.
6. The preparation method of the silicone oil for the waterproof and weather-resistant shoe material according to claim 2, wherein the preparation method comprises the following steps: the dosage of the isopropanol is 35-45 wt%.
7. The preparation method of the silicone oil for the waterproof and weather-resistant shoe material according to claim 2, wherein the preparation method comprises the following steps: before the hydrogen-containing silicone oil is put into preparation, the hydrogen-containing silicone oil is modified, and the modification method comprises the following steps: 1) uniformly mixing heptafluorobutyl methacrylate, dimethylbenzene and a catalyst at room temperature; 2) slowly dripping hydrogen-containing silicone oil, wherein the dripping time is controlled to be 30-40 min; 3) and heating the system to 40-60 ℃, reacting for 2.5-3.5 h at constant temperature, and distilling under reduced pressure to obtain the modified hydrogen-containing silicone oil.
8. The method for preparing the silicone oil for the waterproof and weather-resistant shoe material according to claim 7, wherein the method comprises the following steps: the feeding ratio of the heptafluorobutyl methacrylate to the hydrogen-containing silicone oil is 1: (1-1.3).
9. The method for preparing the silicone oil for the waterproof and weather-resistant shoe material according to claim 7, wherein the method comprises the following steps: the catalyst is cuprous bromide, and the using amount is 10-20 mg/g.
10. The method for preparing the silicone oil for the waterproof and weather-resistant shoe material according to claim 7, wherein the method comprises the following steps: the dosage of the dimethylbenzene is 30-40 wt%.
CN202111646122.4A 2021-12-30 2021-12-30 Silicone oil for waterproof and weather-resistant shoe material and preparation method thereof Withdrawn CN114456387A (en)

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Application Number Priority Date Filing Date Title
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