CN109627445B - A kind of preparation method of straight-chain tertiary amine block amino silicone oil - Google Patents

A kind of preparation method of straight-chain tertiary amine block amino silicone oil Download PDF

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CN109627445B
CN109627445B CN201811531617.0A CN201811531617A CN109627445B CN 109627445 B CN109627445 B CN 109627445B CN 201811531617 A CN201811531617 A CN 201811531617A CN 109627445 B CN109627445 B CN 109627445B
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silicone oil
tertiary amine
amino silicone
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CN109627445A (en
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雷志涛
陶海峰
陈贵龙
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Zhejiang Hanbang new materials Co.,Ltd.
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ZHEJIANG HAPPY CHEMICAL 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
    • C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
    • 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
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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

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Abstract

The invention discloses a preparation method of straight-chain tertiary amine type block amino silicone oil, which comprises the following steps: (1) reacting first double-end oxidation silicone oil with the number of siloxy links of 50-100 with methylethanolamine to generate hydroxyl-end straight-chain tertiary amine amino silicone oil; (2) and (2) carrying out ultrasonic reaction on the terminal hydroxyl straight-chain tertiary amine type amino silicone oil prepared in the step (1) and second double-terminal epoxy silicone oil with the number of silicone-oxygen chain links of 1-5 in the presence of a tertiary amine catalyst to generate straight-chain tertiary amine type block amino silicone oil. The straight-chain tertiary amine type block amino silicone oil prepared by the method has no active hydrogen, so that the phenomena of yellowing and color change caused in the storage and use processes are avoided; and in the whole preparation process, no organic solvent is used, the washing fastness is improved, the environmental protection pressure is reduced, and the use amount of the block silicone oil for achieving the same hand feeling is less than that of the conventional block silicone oil in the after-finishing process of the textile.

Description

Preparation method of straight-chain tertiary amine type block amino silicone oil
Technical Field
The invention relates to a preparation method of straight-chain tertiary amine type block amino silicone oil.
Background
At present, the types of organic silicon used in the textile after-finishing market mainly comprise 2 types, namely amino silicone oil and block silicone oil. These 2 major classes of afterfinish aids each have advantages and also suffer from the following disadvantages: one, amino silicone oil: firstly, the emulsion has poor stability, secondly, the compatibility is poor, and thirdly, the finished textile is hydrophobic and has static electricity; and fourthly, the yellowing and the color change of the fabric are easily caused. Diblock silicone oil: the washing fastness is not good, the washing agent contains solvent, and the block silicone oil has no effect on natural fiber compared with amino silicone oil, and the using amount is large.
In order to overcome the application defects of amino silicone oil and block silicone oil, the method generally adopted is as follows: grafting polyether hydrophilic groups on branched chains of amino silicone oil to seal active hydrogen on amino groups, improving yellowing and color change, and improving hydrophilicity and antistatic property, but causing the reduction of a softening effect; when the block silicone oil is prepared, a low-solvent or solvent-free manufacturing process is adopted, but the raw materials and conditions of the synthesis process are more limited, and the obtained product has a use effect which is not as good as that of the original block silicone oil.
Disclosure of Invention
In view of the above-mentioned disadvantages, the present invention aims to provide a method for preparing a linear tertiary amine type block amino silicone oil.
In order to achieve the purpose of the invention, the invention adopts the following technical scheme: a preparation method of linear tertiary amine type block amino silicone oil comprises the following steps:
(1) preparation of hydroxyl-terminated straight-chain tertiary amine type amino silicone oil: mixing and reacting a first double-terminal epoxy group silicone oil raw material and methyl ethanolamine raw material according to a molar ratio of 1: 2-2.2 to generate a linear chain tertiary amine amino silicone oil; wherein the reaction equation is as follows:
Figure BDA0001905790720000011
(2) preparation of straight-chain tertiary amine type block amino silicone oil: taking the hydroxyl-terminated linear tertiary amine type amino silicone oil obtained in the step (1) as a raw material, adding a second double-terminal epoxy silicone oil and a tertiary amine catalyst as raw materials, and carrying out ultrasonic reaction to generate linear tertiary amine type block amino silicone oil; wherein, the reaction equation is as follows:
Figure BDA0001905790720000021
wherein X is represented by-CH2CH2CH2OCH2-，a＝50～100，a1＝1～5，b≥1。
In the above technical solution, preferably, in the step (1), the reaction conditions for preparing the hydroxyl-terminated linear tertiary amine type amino silicone oil are as follows: controlling the reaction temperature at 75-80 ℃, and carrying out ultrasonic stirring reaction for 2-4 hours with the ultrasonic power of 40-60 watts.
In the above technical solution, preferably, in the step (1), the raw material of the first epoxy-terminated silicone oil and the raw material of the methylethanolamine are pretreated, specifically: vacuumizing at the temperature of 105-110 ℃, stirring for 1-3 hours under the vacuum degree of-0.01-0.03 MPa, and removing the dimethyl siloxane ring body and water remained in the raw material.
In the above technical solution, preferably, in the step (2), the reaction conditions for preparing the linear tertiary amine type block aminosilicone oil are as follows: the temperature is controlled to be 110-130 ℃, the ultrasonic stirring reaction is carried out for 4-6 hours, and the ultrasonic power is 100-200 watts.
In the above technical solution, in the step (2), the amount of the tertiary amine catalyst is preferably 0.1 to 5% of the total weight of the raw material second double-terminal epoxy silicone oil and the raw material hydroxyl-terminal straight-chain tertiary amine type amino silicone oil. .
In the above technical solution, preferably, the tertiary amine catalyst is one or a mixture of two or more of N- (γ' -dimethylaminopropyl) - γ -aminopropylmethyldimethoxysilane, dimethyldodecyl tertiary amine, and tris- (dimethylaminomethyl) phenol.
Compared with the prior art, the invention has the following beneficial effects: 1) the straight-chain tertiary amine type block amino silicone oil prepared according to the invention has no active hydrogen, and the phenomena of yellowing and color change caused in the storage and use processes are avoided; 2) according to the process for preparing the linear-chain tertiary amine type block amino silicone oil, an organic solvent is not used, the washing fastness is improved, and the environmental protection pressure is reduced; 3) the proportion of the linear tertiary amine type block amino silicone oil hydrophilic polyether group prepared according to the invention is smaller, and the use amount of the linear tertiary amine type block amino silicone oil hydrophilic polyether group reaching the same hand feeling is less than that of the conventional block silicone oil in the after-finishing process of textiles.
Detailed Description
In order to explain the technical solution, the achieved objects and the effects of the present invention in detail, several embodiments will be enumerated below.
In the various embodiments described below, it is preferred that,
example 1
A first epoxy-terminated silicone oil (chemical formula is
Figure BDA0001905790720000031
The following examples are the same) and methyl ethanolamine raw materials are pretreated, specifically: vacuumizing at 105-110 ℃, controlling the vacuum degree at-0.01 to-0.03 MPa, stirring for 2 hours, and removing the dimethyl siloxane ring body and the water remained in the raw material.
136.6 g of first epoxy terminated silicone oil with the siloxane chain segment a of 50 and 3.02 g of methylethanolamine are weighed, added into a 500 ml four-neck reaction flask, put into an ultrasonic machine, heated and stirred, the temperature is controlled to be 75-80 ℃, the ultrasonic power is 40 watts, and the reaction is carried out for 2 hours.
Adding siloxane chain segment a1A second epoxy-terminated silicone oil of formula 1
Figure BDA0001905790720000032
The following examples are the same as above), 7.24 g of N- (γ '-dimethylaminopropyl) - γ -aminopropylmethyldimethoxysilane is added, 1.5 g of N- (γ' -dimethylaminopropyl) - γ -aminopropylmethyldimethoxysilane is added, the temperature is raised to 110 ℃, the ultrasonic power is 100 watts, the mixture is stirred and reacted for 6 hours, 1 g of glacial acetic acid is added, and the mixture is stirred for 30 minutes, so that the linear tertiary amine type block amino silicone oil is obtained.
Example 2
The method comprises the following steps of pretreating a first double-end epoxy group silicone oil raw material and methyl ethanolamine raw material: vacuumizing at 105-110 ℃, controlling the vacuum degree to be-0.01-0.03 MPa, stirring for 2 hours, and removing the dimethyl siloxane ring body and the water remained in the raw material.
136.6 g of first epoxy terminated silicone oil with the siloxane chain segment a of 50 and 3.02 g of methylethanolamine are weighed, added into a 500 ml four-neck reaction flask, put into an ultrasonic machine, heated and stirred, the temperature is controlled to be 75-80 ℃, the ultrasonic power is 40 watts, and the reaction is carried out for 2 hours.
Adding siloxane chain segment a1Adding 17.8 g of second double-terminal epoxy group silicone oil of 5, adding 1 g of N- (gamma' -dimethylaminopropyl) -gamma-aminopropyl methyl dimethoxysilane and 1 g of tri- (dimethylaminomethyl) phenol, heating to 110 ℃, enabling the ultrasonic power to be 100 watts, stirring for reacting for 6 hours, adding 1 g of glacial acetic acid, and stirring for 30 minutes to obtain the linear chain tertiary amine type block amino silicone oil.
Example 3
The method comprises the following steps of pretreating a first double-end epoxy group silicone oil raw material and methyl ethanolamine raw material: vacuumizing at the temperature of 105-110 ℃, stirring for 2 hours under the vacuum degree of-0.01-0.03 MPa, and removing the dimethyl siloxane ring body and the water remained in the raw materials.
189.4 g of first dual-end epoxy silicone oil with siloxane chain segment a of 70 and 3.02 g of methylethanolamine are weighed, added into a 500 ml four-neck reaction flask, put into an ultrasonic machine, heated and stirred, the temperature is controlled to be 75-80 ℃, the ultrasonic power is 40 watts, and the reaction is carried out for 3 hours.
Adding siloxane chain segment a1Adding 7.24 g of second epoxy-terminated silicone oil of 1, adding 2.5 g of N- (gamma' -dimethylaminopropyl) -gamma-aminopropylmethyldimethoxysilane, heating to 110 ℃, enabling ultrasonic power to be 100 watts, stirring for reacting for 6 hours, adding 1 g of glacial acetic acid, and stirring for 30 minutes to obtain the linear tertiary amine type blocked amino silicone oil.
Example 4
The method comprises the following steps of pretreating a first double-end epoxy group silicone oil raw material and methyl ethanolamine raw material: vacuumizing at the temperature of 105-110 ℃, stirring for 2 hours under the vacuum degree of-0.01-0.03 MPa, and removing the dimethyl siloxane ring body and the water remained in the raw materials.
189.4 g of first dual-end epoxy silicone oil with siloxane chain segment a of 70 and 3.02 g of methylethanolamine are weighed, added into a 500 ml four-neck reaction flask, put into an ultrasonic machine, heated and stirred, the temperature is controlled to be 75-80 ℃, the ultrasonic power is 40 watts, and the reaction is carried out for 3 hours.
Adding siloxane chain segment a117.8 g of second double-terminal epoxy group silicone oil of 5, 4 g of tris- (dimethylaminomethyl) phenol is added, the temperature is raised to 120 ℃, the ultrasonic power is 150 watts, the stirring reaction is carried out for 6 hours, 1 g of glacial acetic acid is added, and the stirring is carried out for 30 minutes, so as to obtain the straight-chain tertiary amine type block amino silicone oil.
Example 5
The method comprises the following steps of pretreating a first double-end epoxy group silicone oil raw material and methyl ethanolamine raw material: vacuumizing at the temperature of 105-110 ℃, stirring for 2 hours under the vacuum degree of-0.01-0.03 MPa, and removing the dimethyl siloxane ring body and the water remained in the raw materials.
268.6 g of first epoxy terminated silicone oil with siloxane chain segment a of 100 and 3.02 g of methylethanolamine are weighed, added into a 500 ml four-neck reaction flask, put into an ultrasonic machine, heated and stirred, the temperature is controlled to be 75-80 ℃, the ultrasonic power is 60 watts, and the reaction is carried out for 4 hours.
Adding siloxane chain segment a17.24 grams of second epoxy-terminated silicone oil of 1, N- (γ' -dimethylamino) was added2.5 g of propyl) -gamma-aminopropyl methyl dimethoxysilane and 3.5 g of tris- (dimethylaminomethyl) phenol are heated to 120 ℃, the ultrasonic power is 150 watts, the mixture is stirred and reacted for 6 hours, 1 g of glacial acetic acid is added, and the mixture is stirred for 30 minutes. Obtaining the straight-chain tertiary amine block amino silicone oil.
Example 6
The method comprises the following steps of pretreating a first double-end epoxy group silicone oil raw material and methyl ethanolamine raw material: vacuumizing at the temperature of 105-110 ℃, stirring for 2 hours under the vacuum degree of-0.01-0.03 MPa, and removing the dimethyl siloxane ring body and the water remained in the raw materials.
268.6 g of first epoxy terminated silicone oil with siloxane chain segment a of 100 and 3.02 g of methylethanolamine are weighed, added into a 500 ml four-neck reaction flask, put into an ultrasonic machine, heated and stirred, the temperature is controlled to be 75-80 ℃, the ultrasonic power is 60 watts, and the reaction is carried out for 4 hours
Adding siloxane chain segment a1Adding 17.8 g of second double-terminal epoxy silicone oil of 5, adding 3 g of tris- (dimethylaminomethyl) phenol, 3 g of dimethyldodecyl tertiary amine and 4 g of N- (gamma' -dimethylaminopropyl) -gamma-aminopropyl methyldimethoxysilane, heating to 130 ℃, controlling the ultrasonic power at 200 watts, stirring for reacting for 6 hours, adding 1 g of glacial acetic acid, and stirring for 30 minutes to obtain the linear tertiary amine type block amino silicone oil.
The following performance tests were performed on the linear tertiary amine block amino silicone oil prepared by the method selected from the above examples in 3 examples, specifically as follows:
the linear tertiary amine type block amino silicone oil prepared in example 1 emulsified into a softening finish with a solid content of 20%, designated as sample-1 the linear tertiary amine type block amino silicone oil prepared in example 3, emulsified into a softening finish with a solid content of 20%, designated as sample-2 the linear tertiary amine type block amino silicone oil prepared in example 6, emulsified into a softening finish with a solid content of 20%, designated as sample-3 the conventional amino silicone oil, emulsified into a softening finish with a solid content of 20%, designated as sample-4
Conventional block silicone oil emulsified into a soft finish with 20% solids, sample-5
Textile materials for experiments: pure cotton white woven fabric, pure polyester white woven fabric,
the finishing process comprises the following steps: preparing working solution 40 g/L, padding, drying at 95-105 ℃, and shaping at 150-160 ℃ for 60 seconds.
The test contents are as follows:
and (3) evaluation of softening effect: the test is touched by human hands, 5 persons/group, and the test is divided into 1-5 grades, the worst grade 1, and the best yellowing test grade 5: reference is made to GB/T8424.2-2001 textile color fastness test relative whiteness instrument evaluation method.
And (3) determining washing fastness: the test is carried out with reference to GB/T3921.1-1997 colour fastness to washing of the textile colour fastness test.
The performance test of the straight-chain tertiary amine type block amino silicone oil is shown in Table 1
TABLE 1 Performance test results for straight-chain tertiary amine type block amino silicone oils
Figure BDA0001905790720000061
Figure BDA0001905790720000071
The specific embodiments are only for explaining the present invention, and the present invention is not limited thereto, and those skilled in the art can make modifications without inventive contribution to the present embodiments 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 invention.

Claims (6)

1.一种直链叔胺型嵌段氨基硅油制备方法，其特征在于，按照以下步骤进行：1. a straight-chain tertiary amine type block amino silicone oil preparation method, is characterized in that, carry out according to the following steps: (1)端羟基直链叔胺型氨基硅油的制备：将原料第一双端环氧基硅油和原料甲基乙醇胺按照1:2～2.2的摩尔比混合反应，生成端羟基直链叔胺型氨基硅油；其中，反应方程式为：(1) Preparation of hydroxyl-terminated linear tertiary amine type amino silicone oil: the raw material first double-ended epoxy-based silicone oil and the raw material methylethanolamine are mixed and reacted in a molar ratio of 1:2 to 2.2 to generate hydroxyl-terminated linear tertiary amine type Amino silicone oil; wherein, the reaction equation is:
Figure FDA0002815809080000011
Figure FDA0002815809080000011
 (2)直链叔胺型嵌段氨基硅油制备：将上述步骤(1)生成的端羟基直链叔胺型氨基硅油作为原料，加入原料第二双端环氧基硅油和叔胺类催化剂，超声反应，生成直链叔胺型嵌段氨基硅油；其中，反应方程式如下：(2) preparation of straight-chain tertiary amine block amino silicone oil: using the hydroxyl-terminated straight-chain tertiary amine-type amino silicone oil generated in the above step (1) as a raw material, adding the second double-ended epoxy-based silicone oil and a tertiary amine catalyst of the raw material, Ultrasonic reaction generates straight-chain tertiary amine block amino silicone oil; wherein, the reaction equation is as follows:
Figure FDA0002815809080000012
Figure FDA0002815809080000012
 其中，上述X为-CH2CH2CH2OCH2-，a＝50～100，a1＝1～5，b≥1。The above-mentioned X is -CH 2 CH 2 CH 2 OCH 2 -, a=50 to 100, a 1 =1 to 5, and b≧1. 2.根据权利要求1所述的制备方法，其特征在于，在上述步骤(1)中，制备所述端羟基直链叔胺型氨基硅油的反应条件为：控制反应温度在75～80℃，超声搅拌反应2～4小时，超声功率在40～60瓦。2. preparation method according to claim 1 is characterized in that, in above-mentioned step (1), the reaction condition of preparing described hydroxyl-terminated linear tertiary amine type amino silicone oil is: control reaction temperature at 75～80 ℃, The ultrasonic stirring reaction is carried out for 2 to 4 hours, and the ultrasonic power is 40 to 60 watts. 3.根据权利要求1或2所述的制备方法，其特征在于，在上述步骤(1)中，原料第一双端环氧基硅油和原料甲基乙醇胺要进行预处理，具体为：在温度为105～110℃的条件下抽真空，真空度为-0.01～-0.03MPa，搅拌1～3小时，去除残留在原料中的二甲基硅氧烷环体和水分。3. preparation method according to claim 1 and 2, is characterized in that, in above-mentioned step (1), raw material first double-ended epoxy silicone oil and raw material methyl ethanolamine will carry out pretreatment, be specially: at temperature Under the condition of 105～110℃, vacuumize, the vacuum degree is -0.01～-0.03MPa, stir for 1～3 hours, and remove the dimethylsiloxane ring body and water remaining in the raw material. 4.根据权利要求1所述的制备方法，其特征在于，在上述步骤(2)中，制备直链叔胺型嵌段氨基硅油制备的反应条件为：控制温度在110～130℃，超声搅拌反应4～6小时，超声功率在100-200瓦。4. preparation method according to claim 1, is characterized in that, in above-mentioned step (2), the reaction condition that prepares linear tertiary amine type block amino silicone oil preparation is: control temperature at 110～130 ℃, ultrasonic stirring The reaction was carried out for 4-6 hours, and the ultrasonic power was 100-200 watts. 5.根据权利要求1所述的制备方法，其特征在于，在上述步骤(2)中，所述的叔胺类催化剂的用量为原料端羟基直链叔胺型氨基硅油和原料第二双端环氧基硅油的投入总重量的0.1～5％。5. preparation method according to claim 1, is characterized in that, in above-mentioned step (2), the consumption of described tertiary amine catalyst is raw material end hydroxyl straight chain tertiary amine type amino silicone oil and raw material second double end 0.1-5% of the total input weight of epoxy-based silicone oil. 6.根据权利要求1或5所述的制备方法，其特征在于，所述的叔胺类催化剂为N-(γˊ-二甲氨丙基)-γ-氨丙基甲基二甲氧基硅烷、二甲基十二烷基叔胺、三-(二甲胺基甲基)苯酚中的一种或两种以上的混合物。6. preparation method according to claim 1 or 5 is characterized in that, described tertiary amine catalyst is N-(γˊ-dimethylaminopropyl)-γ-aminopropylmethyldimethoxysilane , dimethyl dodecyl tertiary amine, tris-(dimethylaminomethyl) phenol, one or a mixture of two or more.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007024792A1 (en) * 2005-08-25 2007-03-01 Henkel Corporation Rtv silicone compositions using carbamate functional alpha silane crosslinkers
CN102504260A (en) * 2011-11-07 2012-06-20 邬元娟 Method for synthesizing dihydroxyl-terminated polysiloxane
CN107820527A (en) * 2015-05-26 2018-03-20 鲁道夫有限公司 Polyurethane organopolysiloxane

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007024792A1 (en) * 2005-08-25 2007-03-01 Henkel Corporation Rtv silicone compositions using carbamate functional alpha silane crosslinkers
CN102504260A (en) * 2011-11-07 2012-06-20 邬元娟 Method for synthesizing dihydroxyl-terminated polysiloxane
CN107820527A (en) * 2015-05-26 2018-03-20 鲁道夫有限公司 Polyurethane organopolysiloxane

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Denomination of invention: Preparation method of linear tertiary amine block amino silicone oil

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