CN111718490A - Modified block silicone oil containing trace low-ring bodies and preparation method thereof - Google Patents
Modified block silicone oil containing trace low-ring bodies and preparation method thereof Download PDFInfo
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- CN111718490A CN111718490A CN202010756019.4A CN202010756019A CN111718490A CN 111718490 A CN111718490 A CN 111718490A CN 202010756019 A CN202010756019 A CN 202010756019A CN 111718490 A CN111718490 A CN 111718490A
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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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Abstract
The application provides modified block silicone oil containing trace low-ring bodies and a preparation method thereof, which comprises the steps of firstly mixing a linear body with a silane coupling agent KH-560 to obtain an epoxy silicone oil intermediate; and then sequentially adding polyether amine and a solvent into the epoxy silicone oil intermediate to prepare the block silicone oil. The block silicone oil provided by the application adopts a linear body with low ring body content, and is beneficial to synthesizing a more environment-friendly silicone oil product compared with the prior art; the reactive polyether amine is adopted for modification, so that the hydrophilic property of the silicone oil is improved, and the self-emulsification of the silicone oil is realized; the silicone oil provided by the application can endow the textile with better soft, smooth and loose hand feeling, and meanwhile, the yellow degree is lowered; the whole synthesis process is safe to operate and does not need special safety equipment.
Description
Technical Field
The application relates to the technical field of silicone oil, in particular to modified block silicone oil containing trace low ring bodies and a preparation method thereof.
Background
At present, amino silicone oil and modified amino silicone oil endow fabric with special hand feeling, and simultaneously are difficult to avoid the problems of demulsification, roll sticking, yellowing and the like of floating oil in the use process. In recent years, block silicone oils have become popular in the market, and their superior low yellowing property and stability make up for the deficiencies of amino silicone oils, even surpassing amino silicone oils in terms of hand, hydrophilicity and durability. In the synthesis process of the block silicone oil, the epoxy silicone oil is generally synthesized by taking D4(Octamethyl cyclotetramisoxane) and an epoxy end-capping agent as raw materials, and then the epoxy silicone oil and polyether amine are used for synthesizing the ternary copolymerized silicone oil.
The REACH regulation has stipulated that the content of D4 in water-washable cosmetics must be less than 0.1%, with a limit value of < 0.1% (<1000 mg/kg; all product grades) under the newly added test item "silicone", all certifications having come into effect since 4/1 of 2019. Since D4 belongs to the substance tested under the 'siloxane' test item, and the block silicone oil prepared by using D4 as a raw material is one of the raw materials of the silicone softener, in order to meet the requirement of the 'siloxane' content in the REACH regulation, the development of the block silicone oil with low ring body content is urgently needed.
Disclosure of Invention
The application provides modified block silicone oil containing trace low ring bodies and a preparation method thereof, and aims to solve the problem of high siloxane content in the existing block silicone oil preparation process.
In a first aspect of the application, a modified block silicone oil containing trace low ring bodies is provided, wherein the block silicone oil has the following structural formula:
wherein A is:
b is as follows:
c is as follows:
n＝2～5，m＝60～80；
y 9, x + z 3.6 or y 12.5, x + z 6.
In a second aspect of the present application, there is provided a method for preparing a modified block silicone oil containing trace amounts of low ring bodies, comprising:
mixing a linear body and a silane coupling agent KH-560, heating to 80-100 ℃, adding a catalyst, and carrying out heat preservation reaction for 1-2 hours to obtain an epoxy silicone oil intermediate, wherein the linear body is a linear body containing trace low ring bodies;
and sequentially adding polyetheramine and a solvent into the epoxy silicone oil intermediate, heating to 110-130 ℃, carrying out heat preservation reaction for 4-6 h, adding glacial acetic acid at 90-110 ℃, cooling to 40-45 ℃, and discharging to obtain the block silicone oil.
Optionally, the weight ratio of the linear body to the silane coupling agent KH-560 is (35-40): 1.
Optionally, the weight ratio of the epoxy silicone oil intermediate, the polyether amine and the solvent is (90-100): 6-8): 50-60.
Optionally, the polyetheramine is ED-600, ED-900 or a combination of both.
Optionally, the polyether amine is ED-600 and ED-900 according to a molar ratio ED-600: ED-900 ═ 1 to 2: (1-2) mixing.
Optionally, the solvent is one or more selected from butyl glycol ether, tertiary butyl glycol ether and isopropanol.
Optionally, the catalyst is selected from one of potassium hydroxide, sodium hydroxide and tetramethylammonium hydroxide.
In a third aspect of the present application, there is provided the use of a blocked silicone oil as provided by the first aspect, for improving fabric softness.
According to the technical scheme, the application provides modified block silicone oil containing trace low-ring bodies and a preparation method thereof, and firstly, a linear body is mixed with a silane coupling agent KH-560 to obtain an epoxy silicone oil intermediate; and then sequentially adding polyether amine and a solvent into the epoxy silicone oil intermediate to prepare the block silicone oil. The block silicone oil provided by the application adopts a linear body with low ring body content, and is beneficial to synthesizing a more environment-friendly silicone oil product compared with the prior art; the reactive polyether amine is adopted for modification, so that the hydrophilic property of the silicone oil is improved, and the self-emulsification of the silicone oil is realized; the silicone oil provided by the application can endow the textile with better soft, smooth and loose hand feeling, and meanwhile, the yellow degree is lowered; the whole synthesis process is safe to operate and does not need special safety equipment.
Detailed Description
The present invention is further described in conjunction with the following specific embodiments, the features and advantages of which will become more apparent and apparent as the description proceeds.
The present invention is described in detail below.
The application provides a preparation method of modified block silicone oil containing trace low ring bodies, which comprises the following steps:
step 1, mixing a linear body and a silane coupling agent KH-560, heating to 80-100 ℃, adding a catalyst, and carrying out heat preservation reaction for 1-2 hours to obtain an epoxy silicone oil intermediate, wherein the linear body is a linear body containing trace low ring bodies.
The linear body used in the application is a linear body with the model of PMX-0156, and the molecular formula is as follows: HO-Si (CH)3)2-O-[Si(CH3)2]n-Si(CH3)2-OH. The linear body is low molecular weight polydimethylsiloxane terminated by silicon hydroxyl, belongs to low viscosity hydroxyl silicone oil, is applied to production of amino silicone oil in large quantity, has a per pass conversion rate of over 99 percent, and can better generate directional adsorption with carboxyl on the surface of fabric when being used for preparing the amino silicone oil due to containing active hydroxyl, so that the friction coefficient between fibers is obviously reduced, the softness and the smoothness of the fabric are obviously improved, and the washability of the fabric can be improved. The amino silicone oil produced by the linear body has all the properties of the amino silicone oil and also has the property of being easy to be mixed with milkThe lipophilic group combination of the emulsifier, easy emulsion, good dispersibility, good emulsion transparency, small particle size, stable emulsion and the like.
The components provided by the application can be used for synthesizing a more environment-friendly silicone oil product, and the reason is that: the content of low-ring bodies in the American Dow linear body is below 0.1 percent; secondly, when alkali is added for chain extension, a small amount of low ring bodies have partial ring opening; and thirdly, adding a solvent to dilute the content of the low-ring bodies.
In the application, a silane coupling agent KH-560, namely, gamma-glycidoxypropyltrimethoxysilane, which is an epoxy functional group silane, is selected, so that macromolecules can be arranged in a planar matrix instead of a traditional linear arrangement, and the fabric has more ideal hand feeling.
In a practical mode, the weight ratio of the linear body to the silane coupling agent KH-560 is (35-40): 1.
In an achievable form, the catalyst is selected from one of potassium hydroxide, sodium hydroxide, tetramethylammonium hydroxide.
And 2, sequentially adding polyetheramine and a solvent into the epoxy silicone oil intermediate, heating to 110-130 ℃, carrying out heat preservation reaction for 4-6 hours, adding glacial acetic acid at 90-110 ℃, cooling to 40-45 ℃, and discharging to obtain the block silicone oil.
The polyether amine contains amine, is a polymer with a main chain of a polyether structure and an active functional group at the tail end of the polymer as amino, and can enable fabrics to achieve soft and smooth handfeel compared with the traditional active polyether.
In one achievable mode, the polyetheramine is ED-600, ED-900, or a combination of both. Wherein ED-600 is a water-soluble aliphatic diamine with the following structural formula: NH (NH)2CH(CH3)CH2-[OCH(CH3)CH2]X-[OCH2CH2]Y-[OCH2CH(CH3)]Z-NH2Wherein, Y is approximately equal to 9, (X + Z) is equal to 3.6; ED-900 is a water-soluble aliphatic diamine having the following structural formula: NH (NH)2CH(CH3)CH2-[OCH(CH3)CH2]X-[OCH2CH2]Y-[OCH2CH(CH3)]Z-NH2Wherein, Y ≈ 12.5, (X + Z) ═ 6.
According to the application direction of the product, the single mode can be adopted, or the ED-600 and ED-900 can be combined according to different molar ratios, and the ratio can be 1:2 or 2: 1. Whether the combination is needed is determined according to the application point of the product, for example, the combination mode is considered in cotton, polyester cotton, nylon, acrylic fiber and the like.
In one realizable manner, the polyetheramines are ED-600 and ED-900 in the molar ratio ED-600: ED-900 ═ 1 to 2: (1-2) mixing.
In one implementation, the weight ratio of the epoxy silicone oil intermediate, the polyetheramine and the solvent is (90-100): 6-8): 50-60.
In an achievable manner, the solvent is selected from one or more of ethylene glycol butyl ether, ethylene glycol tertiary butyl ether, isopropanol.
The reaction mechanism of the present application is: under the alkaline environment, the silicon-oxygen bond on the linear body and the methoxyl on the coupling agent KH-560 are inoculated into the macromolecule through esterification reaction, the open loop of the active epoxy group at the other end of the coupling agent reacts with the amino groups at the two ends of the amino polyether to form the matrix-type structure macromolecule, and the structural formula is as follows:
wherein A is:
b is as follows:
c is as follows:
n＝2～5，m＝60～80；
y 9, x + z 3.6 or y 12.5, x + z 6.
According to the technical scheme, the block silicone oil containing trace low-ring modification and the preparation method thereof are provided, the block silicone oil provided by the application adopts a linear body with low ring content, and compared with the prior art, the block silicone oil is beneficial to synthesizing a more environment-friendly silicone oil product; the reactive polyether amine is adopted for modification, so that the hydrophilic property of the silicone oil is improved, and the self-emulsification of the silicone oil is realized; the silicone oil provided by the application can endow the textile with better soft, smooth and loose hand feeling, and meanwhile, the yellow degree is lowered; the whole synthesis process is safe to operate and does not need special safety equipment.
The present application is further illustrated below with reference to specific examples.
Example 1
1) Preparation of epoxy silicone oil intermediate: adding 200g of linear PMX-0156 and 5g of silane coupling agent into a 500mL four-mouth bottle provided with a stirrer, a thermometer and a reflux condenser, heating to 90 ℃, adding a potassium hydroxide solution, and carrying out heat preservation reaction for 1-2 hours;
2) preparing modified silicone oil: taking 100g of the synthesized epoxy silicone oil intermediate, sequentially adding 6g of polyetheramine ED-900 and 50g of ethylene glycol butyl ether into the epoxy silicone oil intermediate, heating to 110-130 ℃, reacting for 4-6 h under the condition of heat preservation, adding glacial acetic acid at about 100 ℃, cooling to 45 ℃ and discharging.
Example 2
1) Preparation of epoxy silicone oil intermediate: adding 200g of linear PMX-0156 and 5g of silane coupling agent into a 500mL four-mouth bottle provided with a stirrer, a thermometer and a reflux condenser, heating to 90 ℃, adding a potassium hydroxide solution, and carrying out heat preservation reaction for 1-2 hours;
2) preparing modified silicone oil: taking 100g of the synthesized epoxy silicone oil intermediate, sequentially adding 6g of polyetheramine ED-900 and 50g of isopropanol into the synthesized epoxy silicone oil intermediate, heating to 110-130 ℃, reacting for 4-6 hours under the condition of heat preservation, adding glacial acetic acid at about 100 ℃, cooling to 45 ℃, and discharging.
Example 3
1) Preparation of epoxy silicone oil intermediate: firstly adding 175g of linear PMX-0156 and 5g of silane coupling agent into a 500mL four-mouth bottle provided with a stirrer, a thermometer and a reflux condenser, heating to 90 ℃, adding a potassium hydroxide solution, and carrying out heat preservation reaction for 1-2 hours;
2) preparing modified silicone oil: taking 100g of the synthesized epoxy silicone oil intermediate, sequentially adding 7g of polyetheramine ED-600 and 60g of ethylene glycol butyl ether into the synthesized epoxy silicone oil intermediate, heating to 110-130 ℃, carrying out heat preservation reaction for 4-6 h, adding glacial acetic acid at about 100 ℃, cooling to 45 ℃, and discharging.
Example 4
Isopropanol and polyetheramine were selected.
1) Preparation of epoxy silicone oil intermediate: firstly adding 175g of linear PMX-0156 and 5g of silane coupling agent into a 500mL four-mouth bottle provided with a stirrer, a thermometer and a reflux condenser, heating to 90 ℃, adding a potassium hydroxide solution, and carrying out heat preservation reaction for 1-2 hours;
2) preparing modified silicone oil: taking 100g of the synthesized epoxy silicone oil intermediate, sequentially adding 7g of polyetheramine ED-600 and 60g of isopropanol into the synthesized epoxy silicone oil intermediate, heating to 110-130 ℃, reacting for 4-6 hours under the condition of heat preservation, adding glacial acetic acid at about 100 ℃, cooling to 45 ℃, and discharging.
Comparative example
Two commercially available types of block silicone oils were used as comparative example 1 and comparative example 2, respectively.
Block silicone oil emulsions were prepared using the block silicone oils prepared in examples 1 to 4 and comparative examples 1 to 2, and performance comparisons were made.
The silicone oil emulsion is prepared by the following method:
and (3) taking 40g of the synthesized block silicone oil, adding glacial acetic acid accounting for 2% of the weight of the block silicone oil, uniformly stirring, and then slowly adding water while stirring to obtain the silicone oil emulsion with the concentration of 40%.
The reference emulsion formulation was as follows:
40g of silicone oil;
glacial acetic acid 0.8 g;
water was added to a total of 100 g.
Preparing 20g/L finishing liquid from the prepared silicone oil emulsion, and applying the finishing liquid to all-cotton knitted fabrics, wherein the steps are as follows: the fabric was dipped twice and rolled twice (room temperature, the percentage of the residue after rolling was 70%), pre-baked (100 ℃ C.. times.3 min), baked (140 ℃ C.. times.60 s), and then performance evaluation was performed.
Evaluation method of whiteness of fabric: the whiteness of the finished fabric was measured using a whiteness meter and then compared to a blank fabric. After finishing, the larger the whiteness of the fabric is, the smaller the difference value of the whiteness with the blank fabric is, which indicates that the color change degree of the fabric is smaller.
The hand feeling evaluation method comprises the following steps: the comparison criteria were rated by hand touch for the best hand, softness, smoothness, bulk, grade 5, for the unfinished fabric, grade 1, and for the other finished fabrics against this criteria.
Hydrophilicity evaluation method: the time taken for the fabric to absorb 1 drop of water in the static condition was measured by dropping a drop of water with a standard dropper (25 drops/mL) from a vertical height of 2cm from the fabric onto the surface of the fabric spread horizontally.
The sample performance comparisons are shown in the following table:
table 1 comparison of properties on white all-cotton knitted fabrics
As shown in the table above, after the fabric is treated by the block silicone oil containing trace amounts of low-ring modification prepared in examples 1 to 4, compared with the original cloth and the two comparative examples, the fabric has the best comprehensive hand feeling, is less in yellowing, and has less influence on the hydrophilicity of the fabric, wherein example 1 is the most preferable example of the present application and is a hand feeling finishing agent with market prospect.
The present application has been described in detail with reference to specific embodiments and illustrative examples, but the description is not intended to limit the application. Those skilled in the art will appreciate that various equivalent substitutions, modifications or improvements may be made to the presently disclosed embodiments and implementations thereof without departing from the spirit and scope of the present disclosure, and these fall within the scope of the present disclosure. The protection scope of this application is subject to the appended claims.
Claims (9)
1. The modified block silicone oil containing trace low ring bodies is characterized by having the following structural formula:
wherein A is:
b is as follows:
c is as follows:
n＝2～5，m＝60～80；
y 9, x + z 3.6 or y 12.5, x + z 6.
2. A preparation method of modified block silicone oil containing trace low-ring bodies is characterized by comprising the following steps:
mixing a linear body and a silane coupling agent KH-560, heating to 80-100 ℃, adding a catalyst, and carrying out heat preservation reaction for 1-2 hours to obtain an epoxy silicone oil intermediate, wherein the linear body is a linear body containing trace low ring bodies;
and sequentially adding polyetheramine and a solvent into the epoxy silicone oil intermediate, heating to 110-130 ℃, carrying out heat preservation reaction for 4-6 h, adding glacial acetic acid at 90-110 ℃, cooling to 40-45 ℃, and discharging to obtain the block silicone oil.
3. The production method according to claim 2, wherein the weight ratio of the linear body to the silane coupling agent KH-560 is (35-40): 1.
4. The method of claim 2, wherein the weight ratio of the epoxy silicone oil intermediate, the polyetheramine and the solvent is (90-100): 6-8): 50-60.
5. The method of claim 2, wherein the polyetheramine is ED-600, ED-900, or a combination thereof.
6. The process according to claim 5, wherein the polyetheramine is ED-600 and ED-900 in a molar ratio ED-600: ED-900 ═ 1 to 2: (1-2) mixing.
7. The preparation method according to claim 2, wherein the solvent is one or more selected from ethylene glycol butyl ether, ethylene glycol tertiary butyl ether and isopropanol.
8. The method of claim 2, wherein the catalyst is selected from potassium hydroxide, sodium hydroxide, and tetramethylammonium hydroxide.
9. Use of a blocked silicone oil according to claim 1 for improving fabric softness.
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| CN113373696A (en) * | 2021-06-18 | 2021-09-10 | 广东宏昊化工有限公司 | Softening agent for bamboo fiber fabric and preparation method thereof |
| CN114672026A (en) * | 2022-04-25 | 2022-06-28 | 广东科峰新材料科技有限公司 | Quinary copolymerized super-soft and smooth hydrophilic silicone oil and synthetic method thereof |
| CN114736378A (en) * | 2022-05-13 | 2022-07-12 | 湛江嘉力手套制品有限公司 | Isolating agent component for rubber glove production and synthesis method and application thereof |
| CN115073748A (en) * | 2022-06-29 | 2022-09-20 | 安庆中拓新材料科技有限公司 | Non-ionic water-based organic silicon resin and preparation method thereof |
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| CN113373696A (en) * | 2021-06-18 | 2021-09-10 | 广东宏昊化工有限公司 | Softening agent for bamboo fiber fabric and preparation method thereof |
| CN114672026A (en) * | 2022-04-25 | 2022-06-28 | 广东科峰新材料科技有限公司 | Quinary copolymerized super-soft and smooth hydrophilic silicone oil and synthetic method thereof |
| CN114736378A (en) * | 2022-05-13 | 2022-07-12 | 湛江嘉力手套制品有限公司 | Isolating agent component for rubber glove production and synthesis method and application thereof |
| CN115073748A (en) * | 2022-06-29 | 2022-09-20 | 安庆中拓新材料科技有限公司 | Non-ionic water-based organic silicon resin and preparation method thereof |
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