CN114672029A - Preparation method of nonionic organic silicon surfactant - Google Patents
Preparation method of nonionic organic silicon surfactant Download PDFInfo
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- 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
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Abstract
The invention discloses a preparation method of a nonionic organic silicon surfactant. The coordination addition reaction between the silicon-hydrogen bond of hydrogen-containing silicone oil and the double bond of allyl polyoxyethylene methyl ether is utilized to synthesize a non-ionic silicone surfactant without hydroxyl, the non-ionic silicone surfactant is used as an emulsifier of silicone oil, and the obtained emulsion is used for preparing water-based silicone leather, synthetic leather and textile coatings. The nonionic silicone surfactant prepared by the invention has good compatibility with silicone oil, and can remarkably reduce the interfacial tension between water and silicone oil phases so as to form a stable oil-in-water emulsion. The preparation method has the advantages of adjustable surface activities such as HLB (hydrophilic-lipophilic balance), CMC (critical micelle concentration), cloud point and the like. In addition, the nonionic organic silicon surfactant provided by the invention does not use any organic solvent in the preparation process, can realize the cleanness of the preparation process, and provides a key auxiliary agent support for the development of environment-friendly organic silicon coating materials for leather, synthetic leather and textiles.
Description
Technical Field
The invention relates to a preparation method of a nonionic organic silicon surfactant, belonging to the field of organic silicon materials.
Background
Silicon is rich in nature (occupies 23 percent of shell), and organic silicon compounds are various in variety and are chemical materials independent of petrochemical resources. Because of the unique structure of polysiloxane, a series of excellent performances are shown, and particularly when the polysiloxane is used as a coating material for leather, synthetic leather and textile, the polysiloxane has excellent performances such as weather resistance, wear resistance, scratch resistance, aging resistance, hydrophobicity, antifouling property and the like, so that the polysiloxane is widely used as a novel coating material.
Chinese patent CN108221396B discloses a healthy and safe silicone rubber leather and a coating process thereof, and the raw materials of the composition comprise a silicone rubber raw material which is safe for human health and a bright hand feeling oil. The addition type silicon rubber active group only has carbon-carbon double bonds and silicon-hydrogen bonds, belongs to a two-component addition reaction system, has no by-product, and has no adverse reaction on human body; chinese patent CN111809402A discloses a preparation method of a cyano-modified organic silicon synthetic leather coating, which comprises nonvolatile organic silicon oil and vinyl cyanide monomer as raw materials, and can obtain an organic silicon synthetic leather coating with excellent recoating and bonding properties. The method uses the silicon-based material to replace a carbon-based material to prepare leather, synthetic leather and textile coatings, and provides a new way for promoting carbon peak reaching and carbon neutralization.
Although the organosilicon material has many advantages, the viscosity of the vinyl silicone oil used as the raw material is high when the coating is prepared by the silicon-hydrogen addition reaction, and a nonpolar alkane solvent is required to be added to dilute and reduce the viscosity during application, so that the pollution of VOCs cannot be avoided, and the current development concept of green ecology is not met. The method for preparing the organic silicon coating by preparing the high-viscosity silicone oil into the aqueous emulsion through the surfactant and then performing silicon-hydrogen addition by using the micro-emulsification technology is an effective way for solving the problem of VOCs pollution caused by viscosity reduction of an organic solvent at present. However, the existing surfactant has a series of problems of poor compatibility with vinyl silicone oil and hydrogen-containing silicone oil, large using amount of an emulsifier, dehydrogenation reaction of contained terminal hydroxyl and the hydrogen-containing silicone oil and the like, and the preparation of the water-based silicone oil emulsion is seriously influenced, so that the green application of the organic silicon material in the fields of leather, synthetic leather, textile coatings and the like is limited.
Disclosure of Invention
The invention aims to provide a preparation method of a nonionic organosilicon surfactant aiming at the defects of the prior art. Active hydrogen in the single-end hydrogen-containing silicone oil and double bonds in allyl polyoxyethylene methyl ether are respectively utilized for coordination addition reaction to synthesize a non-ionic organosilicon surfactant without hydroxyl, the non-ionic organosilicon surfactant is used as a silicone oil emulsifier, and the obtained emulsion is used for preparing organosilicon leather, synthetic leather and textile coatings, so that the problem of VOCs (volatile organic compounds) emission caused by viscosity reduction by using an organic solvent is avoided, and the organic solvent is not used in the whole production process, so that the environment-friendly development concept is met.
The invention provides a preparation method of an organic silicon surfactant, which is characterized by comprising the following steps of:
(1) preparation of high HLB nonionic silicone surfactant: adding 12-16 parts of single-end hydrogen-containing silicone oil and 10-14 parts of allyl polyoxyethylene methyl ether into a reaction kettle, controlling the molar ratio of-C = C/-Si-H to be 0.9-1.3, heating to 80-90 ℃, adding 0.1-0.3 part of platinum catalyst, reacting for 1-2H at 100-120 ℃, determining that the content of residual-Si-H groups reaches a theoretical value by a bromoacetic acid titration method, and preparing the compound with the structural formula of
The high HLB value nonionic organosilicon surfactant is disclosed, wherein the value of n is 5-8, and the structural formula of R is-CH2-CH2O(CH2CH2O)mCH3M is 5-10;
(2) preparation of low HLB value nonionic silicone surfactant: adding 10-14 parts of double-end hydrogen-containing silicone oil and 15-18 parts of allyl polyoxyethylene methyl ether into a reaction kettle, controlling the molar ratio of-C = C/-Si-H to be 0.8-1.2, heating to 80-90 ℃, adding 0.2-0.4 part of platinum catalyst, reacting for 2-3H at 110-130 ℃, determining the residual-Si-H group reaction to reach the theoretical value by bromoacetic acid titration, and preparing the compound with the structural formula of
The low HLB value nonionic organosilicon surfactant is disclosed, wherein the value of p is 14-18, and the structural formula of R is-CH2-CH2O(CH2CH2O)mCH3And m is 5 to 10.
The preparation method of the nonionic organosilicon surfactant is characterized in that the hydrogen content of the single-end hydrogen-containing silicone oil is 0.16-0.22%, and the hydrogen content of the double-end hydrogen-containing silicone oil is 0.15-0.18%.
The preparation method of the organosilicon surfactant is characterized in that the platinum catalyst in the method is a complex (Karster catalyst) of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane and chloroplatinic acid (H)2PtCI6·6H2O) isopropanol solution (siebol catalyst).
The preparation method of the nonionic organic silicon surfactant is characterized in that the high-HLB nonionic organic silicon surfactant has a hydrophilic-lipophilic balance HLB of 10-14, a cloud point of 60-68 ℃ and a critical micelle concentration CMC of 0.19-0.25 g/L; the low HLB nonionic organosilicon surfactant has a hydrophilic-lipophilic balance HLB of 3-6, a cloud point of 45-55 ℃, and a critical micelle concentration CMC of 0.07-0.15 g/L.
Compared with the prior art, the invention has the following positive effects:
(1) according to the invention, the allyl polyoxyethylene methyl ether is covalently grafted on two hydrogen-containing silicone oil chains at the ends through a silicon-hydrogen addition reaction, so that the hydroxyl-free nonionic organic silicon surfactant is prepared, has good compatibility with organic silicon components, high reaction activity and high conversion rate, does not need to be separated and purified, does not need any solvent in the preparation process, and meets the requirements of environmental protection;
(2) the hydrophilic-lipophilic balance (HLB), the Critical Micelle Concentration (CMC), the cloud point and the like of the prepared organosilicon surfactant can be regulated and controlled by the lengths of molecular chains of hydrogen-containing silicone oil and allyl polyoxyethylene methyl ether, and the organosilicon surfactant is used alone or in a compound way to provide convenience for preparing organosilicon microemulsion;
(3) compared with the common nonionic surfactant, the molecular chain of the nonionic organic silicon surfactant prepared by the invention is blocked by methyl, and does not contain hydroxyl, so that side reactions such as dehydrogenation and the like generated when the traditional hydroxyl-blocked nonionic surfactant emulsifies hydrogen-containing silicone oil are avoided.
Detailed Description
The present invention is described in detail by the following embodiments, it should be noted that the following embodiments are only used for further illustration of the present invention, and should not be construed as limiting the scope of the present invention, and those skilled in the art can make some insubstantial modifications and adaptations based on the above disclosure, and still fall within the scope of the present invention.
Example 1:
(1) preparation of nonionic silicone surfactant: adding 14 parts of single-end hydrogen-containing silicone oil with the hydrogen content of 0.17 percent and 11 parts of allyl polyoxyethylene methyl ether with the molecular weight of 290 g/mol into a reaction kettle, controlling the molar ratio of-C = C and-Si-H to be 1.0, heating to 85 ℃, adding 0.1 part of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, and reacting at 100 ℃ for 1.5 hours to prepare the nonionic organosilicon surfactant with the high HLB value; 11 parts of hydrogen-terminated polysiloxane with hydrogen content of 0.16 percent and 14 parts of allyl polyoxyethylene methyl ether with molecular weight of 380 g/mol are added into a reaction kettle, the molar ratio of-C = C and-Si-H is controlled at 0.8, the temperature is raised to 85 ℃, 0.2 part of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane is added, and the reaction is carried out for 1.5 hours at 110 ℃, thus obtaining the low HLB value nonionic organosilicon surfactant.
Tests show that the critical surface tension of the prepared nonionic organosilicon surfactant with the high HLB value is 24.5 mN/m, the critical micelle concentration is 0.20 g/L, the HLB value is 11.5, and the cloud point is 66 ℃; the critical surface tension of the low HLB nonionic silicone surfactant is 21.5 mN/m, the critical micelle concentration is 0.09 g/L, the HLB value is 4.0, and the cloud point is 48 ℃. The two surfactants are used independently or compounded, are transparent and uniform after being blended with silicone oil with different viscosities, and show good compatibility.
Example 2:
(1) preparation of nonionic silicone surfactant: adding 15 parts of single-end hydrogen-containing silicone oil with the hydrogen content of 0.19 percent and 12 parts of allyl polyoxyethylene methyl ether with the molecular weight of 330 g/mol into a reaction kettle, controlling the molar ratio of-C = C and-Si-H to be 1.1, heating to 80 ℃, adding 0.2 part of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, and reacting at 110 ℃ for 1H to prepare the nonionic silicone surfactant with the high HLB value; adding 12 parts of hydrogen-containing silicone oil with double ends and hydrogen content of 0.17 percent and 16 parts of allyl polyoxyethylene methyl ether with molecular weight of 420 g/mol into a reaction kettle, controlling the molar ratio of-C = C and-Si-H to be 1.0, heating to 80 ℃, adding 0.2 part of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane, and reacting for 1H at 120 ℃ to obtain the low HLB value nonionic silicone surfactant.
Tests show that the critical surface tension of the prepared nonionic organosilicon surfactant with the high HLB value is 25.3 mN/m, the critical micelle concentration is 0.26 g/L, the HLB value is 12, and the cloud point is 68 ℃; the critical surface tension of the low HLB nonionic silicone surfactant is 22.0 mN/m, the critical micelle concentration is 0.07 g/L, the HLB value is 3.8, and the cloud point is 45 ℃. The two surfactants are used independently or compounded, are transparent and uniform after being blended with silicone oil with different viscosities, and show good compatibility.
Example 3:
(1) preparation of nonionic silicone surfactant: 16 parts of single-end hydrogenpolysiloxane with hydrogen content of 0.22 percent and 13 parts of allyl polyoxyethylene methyl ether with molecular weight of 460 g/mol are added into a reaction kettle, the molar ratio of-C = C and-Si-H is controlled to be 1.2, the temperature is raised to 90 ℃, 0.1 part of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane and chloroplatinic acid (H) are added2PtCI6·6H2O) 0.2 portion of isopropanol solution, and reacting for 2 hours at 115 ℃ to prepare the nonionic organosilicon surfactant with high HLB value; 11 parts of hydrogen-terminated polysiloxane with hydrogen content of 0.17 percent and 13 parts of allyl polyoxyethylene methyl ether with molecular weight of 510 g/mol are added into a reaction kettle, the molar ratio of-C = C and-Si-H is controlled to be 1.2, the temperature is raised to 90 ℃, 0.1 part of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane and chloroplatinic acid (H) are added2PtCI6·6H2O) 0.2 portion of isopropanol solution, and reacting for 2.5 hours at 130 ℃ to prepare the low HLB value nonionic organosilicon surfactant.
Tests show that the critical surface tension of the prepared nonionic organosilicon surfactant with the high HLB value is 25.0 mN/m, the critical micelle concentration is 0.23 g/L, the HLB value is 11, and the cloud point is 62 ℃; the critical surface tension of the low HLB nonionic silicone surfactant is 21.0 mN/m, the critical micelle concentration is 0.11 g/L, the HLB value is 4.5, and the cloud point is 50 ℃. The two surfactants are used independently or compounded, are transparent and uniform after being blended with silicone oil with different viscosities, and show good compatibility.
Claims (4)
1. A preparation method of a nonionic organic silicon surfactant is characterized by comprising the following steps of:
(1) preparation of high HLB nonionic silicone surfactant: adding 12-16 parts of single-end hydrogen-containing silicone oil and 10-14 parts of allyl polyoxyethylene methyl ether into a reaction kettle, controlling the molar ratio of-C = C/-Si-H to be 0.9-1.3, heating to 80-90 ℃, adding 0.1-0.3 part of platinum catalyst, reacting for 1-2H at 100-120 ℃, determining that the content of residual-Si-H groups reaches a theoretical value by a bromoacetic acid titration method, and preparing the compound with the structural formula of
The high HLB value nonionic organosilicon surfactant is disclosed, wherein the value of n is 5-8, and the structural formula of R is-CH2-CH2O(CH2CH2O)mCH3M is 5-10;
(2) preparation of low HLB nonionic silicone surfactant: adding 10-14 parts of double-end hydrogen-containing silicone oil and 15-18 parts of allyl polyoxyethylene methyl ether into a reaction kettle, controlling the molar ratio of-C = C/-Si-H to be 0.8-1.2, heating to 80-90 ℃, adding 0.2-0.4 part of platinum catalyst, reacting for 2-3 hours at 110-130 ℃, determining the residual-Si-H group reaction to a theoretical value by bromoacetic acid titration, and obtaining the compound with the structural formula of
The low HLB value nonionic organosilicon surfactant is disclosed, wherein the value of p is 14-18, and the structural formula of R is shown in the specification-CH2-CH2O(CH2CH2O)mCH3And m is 5 to 10.
2. The method according to claim 1, wherein the hydrogen content of the single-end hydrogen-containing silicone oil is 0.16-0.22%, and the hydrogen content of the double-end hydrogen-containing silicone oil is 0.15-0.18%.
3. The method according to claim 1, wherein the platinum catalyst is a complex of platinum-1, 3-divinyl-1, 1,3, 3-tetramethyldisiloxane (Karster's catalyst), chloroplatinic acid (H), or a mixture thereof2PtCI6·6H2O) isopropanol solution (siebol catalyst).
4. The method for preparing the nonionic silicone surfactant according to claim 1, wherein the high HLB nonionic silicone surfactant has a hydrophilic-lipophilic balance HLB of 10 to 14, a cloud point of 60 to 68 ℃, and a critical micelle concentration CMC of 0.19 to 0.25 g/L; the low HLB nonionic organosilicon surfactant has a hydrophilic-lipophilic balance HLB of 3-6, a cloud point of 45-55 ℃, and a critical micelle concentration CMC of 0.07-0.15 g/L.
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