CN112574419A - Single-ended acryloyloxy polysiloxane and preparation method thereof - Google Patents
Single-ended acryloyloxy polysiloxane and preparation method thereof Download PDFInfo
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- CN112574419A CN112574419A CN202010780832.5A CN202010780832A CN112574419A CN 112574419 A CN112574419 A CN 112574419A CN 202010780832 A CN202010780832 A CN 202010780832A CN 112574419 A CN112574419 A CN 112574419A
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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
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
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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
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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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
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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Abstract
The invention relates to the field of high polymer materials, in particular to single-ended acryloxy polysiloxane and a preparation method thereof; the acrylic emulsion modified by the functional monomer prepared by the invention has the average particle size of 60-150nm, has good surface hand feeling, water resistance and dirt resistance and good stability, can be used for surface treatment of leather, fabrics and the like, has the functions of softness, smoothness and the like, and can be widely applied to the fields of textiles, leather, coatings, water-based ink and the like.
Description
Technical Field
The invention relates to the field of high polymer materials, in particular to a preparation method and application of organosilicon with end group reaction groups.
Technical Field
The acrylic emulsion has excellent film forming property, good weather resistance, gloss and adhesive force, low price and no pollution, and is one of the most widely applied coatings at present. However, the acrylic emulsion generally has the defects of poor water resistance, hot stickiness and cold brittleness and contradiction between hand feeling and fastness of pigment printed fabrics, and the application range of the acrylic emulsion is limited. The acrylic emulsion is structurally modified by utilizing the characteristics of low surface energy, high and low temperature resistance, good hydrophobicity, good air permeability and the like of the organic silicon material, so that the inherent defects of the acrylic polymer can be eliminated, and the emulsion performance is greatly improved.
From the current research situation at home and abroad, most of the modification of acrylic emulsion by organosilicon is carried out by using a micromolecule silane coupling agent with unsaturated groups or micromolecule hydroxyl silicone oil emulsion, the emulsion synthesized is poor in stability and easy to gel after being placed, and hydrolysis and acid and alkali are not resisted. The invention synthesizes polysiloxane with acryloyloxy at one end, in particular polydimethylsiloxane with acryloyloxy at one end, and modifies acrylic emulsion.
Disclosure of Invention
Technical problem to be solved
The invention aims to provide a single-end acryloxy polysiloxane which can be used for modifying acrylic ester. The acryloxy polysiloxane prepared by the invention only contains one reactive group in each molecular chain, is relatively resistant to hydrolysis, is not easy to gel, is positioned at a terminal group, and has higher reactivity than common vinyl silicone oil. The modified acrylate emulsion has the average particle size of 60-150nm, has good surface hand feeling, hydrophobicity and stability, can be used for surface treatment of leather, fabrics and the like, has the functions of softness, smoothness and the like, and can be widely applied to the fields of textiles, leather, coatings, water-based ink and the like.
(II) technical scheme
The invention provides single-ended acryloxy polysiloxane, which is prepared by the addition reaction of single-ended hydrogen-containing silicone oil and unsaturated hydroxyl derivatives in a solvent under the catalytic action of a Pt-based catalyst, and the esterification reaction of the single-ended hydroxyl polysiloxane and unsaturated carboxylic acid derivatives in a polymerization inhibitor and a catalyst.
The Pt catalyst is prepared by reacting 1g of chloroplatinic acid with 50ml of solvent, wherein the solvent is one of toluene, ethanol, isopropanol and acetone.
The molecular weight of the single-end hydrogen-containing silicone oil is 500-3000, or the molecular weight of the single-end hydrogen-containing silicone oil is 500-3000.
The unsaturated hydroxyl derivative is one of allyl alcohol, octenol, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, allyl polyoxyethylene ether, allyl polyoxypropylene ether and ethylene glycol monoallyl ether.
The solvent is toluene or xylene.
The unsaturated carboxylic acid derivative is acrylic acid or methacrylic acid.
The polymerization inhibitor is one of hydroquinone, hydroquinone monomethyl ether, 2, 5-di-tert-butyl hydroquinone and 2-tert-butyl hydroquinone.
The catalyst for the esterification reaction is one of p-toluenesulfonic acid, butyl titanate, acidic ion exchange resin and dibutyltin dilaurate.
The single-ended acryloyloxy polysiloxane is used for preparing acrylic emulsion.
The preparation method of the single-ended acryloyloxy polysiloxane comprises the following steps:
step 1: adding single-end hydrogen-containing silicone oil, unsaturated hydroxyl derivatives, a catalyst and a solvent into a three-neck flask, heating to a certain temperature, reacting for a period of time, and performing suction filtration to obtain single-end hydroxyl polysiloxane;
step 2: adding single-end hydroxyl polysiloxane, acrylic acid or methacrylic acid, toluene, a catalyst for esterification reaction and a polymerization inhibitor into a three-neck flask, reacting for a period of time at a certain temperature, and carrying out reduced pressure distillation to obtain the single-end acryloxy polysiloxane.
The invention has the beneficial technical effects that:
the invention adopts single-end acryloxy polydimethylsiloxane, and because a certain polyoxyethylene chain segment is introduced, the hydrophilicity is good, the silicon modified acrylic emulsion has better compatibility with monomers polymerized by acrylic emulsion, and the silicon modified acrylic emulsion with high silicon content and good stability is prepared.
Through modification of the single-end-functional polysiloxane, organosilicon is more easily distributed on the surface of resin when the acrylic emulsion is formed into a film, and polysiloxane forms a surface structure like hair, so that the water resistance, stain resistance, anti-sticking property, dry and wet rubbing wear resistance of the coating are improved, and the smooth and soft hand feeling of the coating is provided.
Detailed Description
Example 1
A single-ended acryloxy polysiloxane prepared by the following method:
firstly, adding single-end hydrogen-containing silicone oil with the molecular weight of 1000, allyl polyoxyethylene ether with the molecular weight of 350 and chloroplatinic acid isopropanol solution with the molar ratio of 1:1.1 and the total mass of 0.1 wt% of the two as catalysts and toluene with the mass fraction of 15 wt% of monomers into a three-neck flask, heating, introducing nitrogen, stirring, slowly heating to 90 ℃ for reaction for 4 hours, and carrying out reduced pressure distillation at 120 ℃ to obtain the single-end hydroxyl polysiloxane.
The method comprises the steps of weighing single-terminal hydroxyl polysiloxane and acrylic acid according to a molar ratio of 1:1.1, adding toluene with the mass of 30 wt% of monomer for carrying out water, p-toluenesulfonic acid with the mass of 5% of monomer as a catalyst, hydroquinone with the mass of 0.1% of monomer as a polymerization inhibitor into a three-neck flask, connecting with a water separator, introducing nitrogen, heating, stirring, heating to 115 ℃, measuring an acid value after reacting for a period of time, heating to 140 ℃, carrying out reduced pressure distillation, cooling to room temperature, and filtering to obtain the single-terminal acryloxy polysiloxane.
Example 2
A single-ended acryloxy polysiloxane prepared by the following method:
firstly, adding a single-end hydrogen-containing silicone oil with the molecular weight of 1500 and allyl alcohol into a three-neck flask according to the molar ratio of 1:1.05, a chloroplatinic acid isopropanol solution which is 0.5 wt% of the total mass of the two as a catalyst and toluene with the mass fraction of 30 wt% of a monomer, heating, introducing nitrogen, stirring, slowly heating to 80 ℃ for reaction for 6 hours, and carrying out reduced pressure distillation at 120 ℃ to obtain the single-end hydroxyl polysiloxane.
The method comprises the steps of weighing single-terminal hydroxyl polysiloxane and acrylic acid according to a molar ratio of 1:1.2, adding toluene with 70 wt% of monomer mass for carrying out water, p-toluenesulfonic acid with 5% of monomer mass as a catalyst, hydroquinone with 0.5% of monomer mass as a polymerization inhibitor into a three-neck flask, connecting a water separator, introducing nitrogen, heating, stirring, heating to 100 ℃, measuring an acid value after reacting for a period of time, heating to 140 ℃, carrying out reduced pressure distillation, cooling to room temperature, and filtering to obtain the single-terminal acryloxy polysiloxane.
Example 3
A single-ended acryloxy polysiloxane prepared by the following method:
firstly, adding single-end hydrogen-containing silicone oil with the molecular weight of 500, 4-hydroxybutyl acrylate and chloroplatinic acid isopropanol solution with the molar ratio of 1:1.2 and 0.2 wt% of the total mass of the two as a catalyst and toluene with the monomer mass fraction of 50 wt% into a three-neck flask, heating, introducing nitrogen, stirring, slowly heating to 120 ℃ for reaction for 2 hours, and carrying out reduced pressure distillation at 120 ℃ to obtain the single-end hydroxyl polysiloxane.
Weighing single-terminal hydroxyl polysiloxane and methacrylic acid according to a molar ratio of 1:1.05, adding 100 wt% of toluene for carrying out water, 2 wt% of p-toluenesulfonic acid as a catalyst and 1 wt% of hydroquinone as a polymerization inhibitor into a three-neck flask, connecting with a water separator, introducing nitrogen, heating, stirring, heating to 120 ℃, measuring the acid value after reacting for a period of time, heating to 160 ℃, distilling under reduced pressure, cooling to room temperature, and filtering to obtain the single-terminal acryloxy polysiloxane.
Test example:
preparation of a single-ended acryloxy polysiloxane-modified acrylate emulsion: preparing an emulsifier solution from sodium dodecyl sulfate and an emulsifier OP-10 according to the mass ratio of 1: 1.5 for later use. By K2S2O8Preparing an initiator with the mass fraction of 1.5% for later use; adding single-end acryloxy polysiloxane and n-butyl acrylate (3.6g) into a certain amount of emulsifier aqueous solution, stirring at high speed and carrying out ultrasonic treatment for 30 min; reducing the stirring speed, dropwise adding 4/9 initiator aqueous solution, and reacting for a period of time to obtain an emulsion which is a seed emulsion; keeping the temperature for 30min after the blue light is presented, and adding water to the mixtureAnd slowly dripping the rest initiator aqueous solution into a reaction container of the seed emulsion, reacting at constant temperature for 60-90 min after dripping, cooling to room temperature after the reaction is finished, and filtering by using a 200-mesh screen to obtain the product.
Preparation of acrylate emulsion: preparing an emulsifier solution from sodium dodecyl sulfate and an emulsifier OP-10 according to the mass ratio of 1: 1.5 for later use. By K2S2O8Preparing an initiator with the mass fraction of 1.5% for later use; adding n-butyl acrylate (3.6g) into a certain amount of emulsifier aqueous solution, stirring at high speed and carrying out ultrasonic treatment for 30 min; reducing the stirring speed, dropwise adding 4/9 initiator aqueous solution, and reacting for a period of time to obtain an emulsion which is a seed emulsion; and (3) keeping the temperature for 30min after the blue light is presented, slowly dropwise adding the rest initiator aqueous solution into a reaction container containing the seed emulsion, reacting at the constant temperature for 60-90 min, cooling to room temperature after the reaction is finished, and filtering by using a 200-mesh screen to obtain the product.
The finishing process of the linen fabric comprises the following steps: preparing the prepared fluorine-containing silicon polymer emulsion finishing agent into finishing liquid with a certain concentration by using deionized water, then placing the finishing liquid into an ultrasonic processor for ultrasonic treatment for 30min (adopting stepped ultrasonic treatment), padding linen fabric, pre-drying, baking, washing and drying.
1. Emulsion Performance test
Method for determining emulsion particle morphology: the average particle size of the emulsion was measured using a Nano-S90 type laser particle size Analyzer. When in test, the emulsion is diluted by deionized water, and is subjected to ultrasonic high-frequency oscillation for 3min to fully disperse agglomerated particles in the emulsion, wherein the test temperature is 25 ℃, and the results are shown in the following table 1.
Test method for storage stability: the prepared emulsion was placed in a glass test tube, sealed and left to stand, and whether or not it was delaminated was observed, and if it was not delaminated within the storage time, it was considered that the storage stability was good, otherwise, it was considered that the storage stability was poor, and the results are shown in table 1 below.
Testing of contact Angle: diluting the emulsion to 0.5%, spin-coating on clean glass sheet at 3000r/min, drying the emulsion film at 80 deg.C for 3h to remove solvent, and annealing at 120 deg.C overnight. The results of measuring the contact angle of the reference solution on the surface of the latex film at 20 ℃ by using deionized water (72.8mN/m) as the reference solution are shown in the following table:
TABLE 1 emulsion Performance test results
| Examples | Example 1 | Example 2 | Example 3 | Acrylic ester emulsion | Blank control |
| Average particle diameter (nm) | 102.4 | 108.2 | 103.5 | 187 | — |
| Stability of | Not layering | Not layering | Not layering | Not layering | — |
| Contact angle (°) | 109.32° | 110.01° | 109.59° | 128.33° | 131.63° |
Table 1 shows that the acrylic ester emulsion has a large particle size, the average particle size of the emulsion modified by the single-ended acryloxy polysiloxane prepared by the present invention is rapidly reduced, and the emulsion has good stability, and the contact angle of the linen fabric finished by the single-ended acryloxy polysiloxane modified acrylic ester emulsion prepared by the present invention to water is significantly improved compared with the unmodified acrylic ester emulsion. The acrylate emulsion modified by the single-ended acryloyloxy polysiloxane prepared by the invention has good hydrophobicity.
2. Test of wearability
Air permeability test method: the air permeability test was carried out by using an air permeability tester according to GB/T5453-1997 determination of textile fabric air permeability, GB/T4689.22-1996 determination of leather air permeability, the results of which are shown in Table 2.
The moisture permeability test method comprises the following steps: according to GB/T12704.1-2009 part 1 of determination of moisture permeability of textile fabrics: wet blotting ", the results are shown in table 2.
The breaking strength test method comprises the following steps: according to GB/T3923.1-2013 part 1 of tensile properties of textile fabrics: determination of breaking Strength and elongation at Break-strip method ", the results are shown in Table 2.
Flexural rigidity test method: determination of the flexural Properties of textiles according to GB T18318.5-2009, part 5: pure bending method ", the results are shown in Table 2.
The friction factor test method comprises the following steps: the test was carried out using a friction coefficient meter MXD-01 according to the following procedure,
1. a test specimen was mounted flat on a horizontal test stand with the test surface facing upward. The test specimen and the test bed should be parallel in length.
2. The test surface of the other sample is faced downwards, the slide block is wrapped, and the sample is fixed on the front edge and the upper surface of the slide block by using an adhesive tape.
3. If the sample is thick or rigid, bending moment may occur and the pressure distribution may be uneven, a 63mm × 63mm sample should be used. The sample was held between the bottom surface of the slide and the non-test surface of the sample with a double-sided tape.
4. Both samples were held flat, without wrinkles and scratches that could alter the frictional properties. The edges of the sample should be smooth; the test surface of the test specimen should be free of dust, fingerprints, and any foreign substances that might alter the surface properties.
5. The slide block with the fixed samples is placed in the center of the first sample without impact, the test directions of the two samples are parallel to the sliding direction, and the force measuring system is just not stressed.
6. The two samples were held in contact for 15 seconds. The instrument is activated to move the two samples relative to each other.
7. The first peak in force is static friction. The average value of the forces (excluding the static friction) within 6cm of the relative movement of the two samples was the kinetic friction.
8. If force value oscillations occur after the static friction force, the kinetic friction force cannot be measured. At this time, a spring between the slider and the load sensor is eliminated, and the dynamic friction force is measured independently.
The results are shown in Table 2.
TABLE 2 indexes of various properties of the finished linen fabric
As can be seen from Table 2, the moisture permeability and air permeability of the linen fabric finished by the prepared single-ended acryloxy polysiloxane modified acrylate emulsion are not greatly different from those of the untreated linen fabric, but the tensile capacity is obviously improved, the bending rigidity is obviously reduced, and the fabric friction is slightly reduced, which shows that the invention can improve the defect that the linen fabric is easy to wrinkle, and simultaneously, the fabric is smooth and flexible.
Claims (10)
1. A single-end acryloxy polysiloxane is characterized in that under the catalytic action of a Pt-series catalyst, single-end hydrogen-containing silicone oil and an unsaturated hydroxyl derivative are subjected to addition reaction in a solvent to prepare the single-end hydroxyl polysiloxane, and the single-end hydroxyl polysiloxane and an unsaturated carboxylic acid derivative are subjected to esterification reaction in the presence of a polymerization inhibitor and an esterification reaction catalyst to prepare the single-end acryloxy polysiloxane.
2. The single-ended acryloxypolysiloxane according to claim 1, characterized in that: the Pt catalyst is prepared by reacting 1g of chloroplatinic acid with 50ml of solvent, wherein the solvent is one of toluene, ethanol, isopropanol and acetone.
3. The single-ended acryloxypolysiloxane according to claim 1, characterized in that: the molecular weight of the single-end hydrogen-containing silicone oil is 500-3000, or the molecular weight of the single-end hydrogen-containing silicone oil is 500-3000.
4. The single-ended acryloxypolysiloxane according to claim 1, characterized in that: the unsaturated hydroxyl derivative is one of allyl alcohol, octenol, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, 4-hydroxybutyl acrylate, allyl polyoxyethylene ether, allyl polyoxypropylene ether and ethylene glycol monoallyl ether.
5. The single-ended acryloxypolysiloxane according to claim 1, characterized in that: the solvent is toluene or xylene.
6. The single-ended acryloxypolysiloxane according to claim 1, characterized in that: the unsaturated carboxylic acid derivative is acrylic acid or methacrylic acid.
7. The single-ended acryloxypolysiloxane according to claim 1, characterized in that: the polymerization inhibitor is one of hydroquinone, hydroquinone monomethyl ether, 2, 5-di-tert-butyl hydroquinone and 2-tert-butyl hydroquinone.
8. The single-ended acryloxypolysiloxane according to claim 1, wherein the catalyst for the esterification reaction is one of p-toluenesulfonic acid, butyl titanate, acidic ion exchange resin, dibutyltin dilaurate.
9. The single-ended acryloxy polysiloxane of claim 1, wherein said single-ended acryloxy polysiloxane is used to prepare an acrylic emulsion.
10. A preparation method of single-ended acryloyloxy polysiloxane is characterized by comprising the following steps:
step 1: adding single-end hydrogen-containing silicone oil, unsaturated hydroxyl derivatives, a catalyst and a solvent into a three-neck flask, heating to a certain temperature, reacting for a period of time, and performing suction filtration to obtain single-end hydroxyl polysiloxane;
step 2: adding single-end hydroxyl polysiloxane, acrylic acid or methacrylic acid, toluene, a catalyst for esterification reaction and a polymerization inhibitor into a three-neck flask, reacting for a period of time at a certain temperature, and carrying out reduced pressure distillation to obtain the single-end acryloxy polysiloxane.
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Cited By (3)
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| CN115181271A (en) * | 2022-08-17 | 2022-10-14 | 浙江工业职业技术学院 | Fluorine-containing vinyl polysiloxane, printing raw paste and preparation method thereof |
| CN115260863A (en) * | 2022-08-23 | 2022-11-01 | 广东多正树脂科技有限公司 | Water-repellent water-based acrylic resin coating and preparation method and use method thereof |
| CN116120559A (en) * | 2022-12-09 | 2023-05-16 | 广州硅碳新材料有限公司 | Polyester silicone wax and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115181271A (en) * | 2022-08-17 | 2022-10-14 | 浙江工业职业技术学院 | Fluorine-containing vinyl polysiloxane, printing raw paste and preparation method thereof |
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| CN116120559A (en) * | 2022-12-09 | 2023-05-16 | 广州硅碳新材料有限公司 | Polyester silicone wax and preparation method thereof |
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Application publication date: 20210330 |