CN109867790B - Organic silicon polyether copolymer and preparation method thereof - Google Patents
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Abstract
The invention discloses a preparation method of an organic silicon polyether copolymer, which belongs to the technical field of organic silicon surfactants and aims to solve the problems of more side reactions and difficult control in the hydrosilylation reaction process in the prior art, octamethylcyclotetrasiloxane, tetramethylcyclotetrasiloxane, hexamethyldisiloxane and an acid catalyst are added into a reactor according to a certain proportion, the temperature is raised to the reaction temperature, and hydrogen-containing polymethylsiloxane is prepared by heat preservation; adding the prepared hydrogen-containing polymethylsiloxane, the terminal allyl polyether, the catalyst, the hindered amine and the antioxidant into a reactor, heating to a certain temperature under normal pressure, and preserving heat to obtain the organic silicon polyether copolymer. By adopting the compounding of the hindered amine and the antioxidant, the invention not only effectively controls the formation of dehydropolycondensation and acetal, avoids the autoxidation of polyether, reduces the generation of side reaction, but also reduces the dosage of the catalyst to a certain extent, and can accelerate the reaction rate by adding the antioxidant in the reaction.
Description
Technical Field
The invention relates to a copolymer and a preparation method thereof, in particular to an organic silicon polyether copolymer and a preparation method thereof, belonging to the technical field of organic silicon surfactants.
Background
Silicone surfactants have been widely used as foam homogenizers, softening finishes, high-efficiency emulsifiers, defoamers, coating wetting agents, plastic additives, personal care product raw materials and auxiliaries, due to their outstanding water solubility, compatibility, emulsifiability and surface activity. However, in the hydrosilylation reaction, when the unsaturated terminal compound contains a hydroxyl group, side reactions such as dehydrocondensation and acetal formation, polyether autooxidation, and the like are liable to occur, and the performance of the product is seriously affected. In order to reduce the influence of side reactions, researchers find through experiments that the side reactions can be effectively controlled by adding some substances in the hydrosilylation reaction process, and the reaction selectivity is improved, so that the product viscosity is reduced, and the water solubility of the product is increased.
U.S. Pat. No. 4, 6372874, 1, U.S. Pat. No. 5,973, 20150105576, 1 and U.S. Pat. No. 3, 20160160009, 1 disclose a method for controlling side reactions in hydrosilylation, which is characterized in that secondary amine or tertiary amine containing hydroxyl, carbonyl or ether bonds is used as a catalyst buffer agent, added into a reaction system according to a certain proportion, heated and reacted for a certain time to obtain a low-viscosity product, thereby effectively reducing the formation of byproducts such as dehydropolycondensation and acetal. European patent EP0314903, US patent US005159096A, US4847398, etc. disclose that carboxylic acid or carboxylate is used as hydrosilylation reaction additive to avoid the use of solvent in traditional process and inhibit acetal formation effectively, while carboxylate additive inhibits main reaction to some extent, resulting in more catalyst, longer induction period and darker product color.
The method analyzes the automatic oxidation reaction of polyether and the influence of the automatic oxidation reaction on the hydrosilylation reaction process by the polyether, researches the control effect of adding antioxidant to pre-treat the polyether on the content of cross-linking by-products in the product, and shows that the antioxidant propyl gallate has the best inhibition effect on side reactions, and can obviously reduce the content of cross-linking products in the product under the conditions that the adding amount is 2 percent (wt) of the total amount of the polyether, the treatment temperature is 80 ℃, and the treatment time is 1 h.
Although the method can effectively control the side reaction in the hydrosilylation reaction, for the hydrogen-containing polymethylhydrosiloxane with high hydrogen content to easily generate the cross-linking side reaction in the hydrosilylation reaction, the generation of the side product can not be effectively reduced only by singly adopting one steric hindrance amine or antioxidant, or the proceeding of the side reaction can be effectively reduced under the excessive using amount of the steric hindrance amine, but the main reaction speed can also be inhibited, so that the using amount of the catalyst is increased, and the production cost is increased; in addition, although the antioxidant additive can effectively reduce the autoxidation reaction of polyether, the inhibition effect on the side reaction of dehydrogenation polycondensation and acetal formation is relatively weak, the reaction yield is low, and the product viscosity is high.
Disclosure of Invention
The invention mainly aims to solve the problems of more side reactions and difficult control in the hydrosilylation reaction process in the prior art, and provides a preparation method of an organic silicon polyether copolymer.
The purpose of the invention can be achieved by adopting the following technical scheme:
a silicone polyether copolymer having the structure:
wherein: m is 8-70, n is 0-15, and m + n is 10-90;
the structure of R is: -CH2CH2CH2O(CH2CH2O)a(CH2CH(CH3)O)bR1A is 0 to 20, b is 1 to 20, a + b is 1 to 20, R1Alkyl with 1-4 carbon atoms or hydrogen.
A preparation method of a silicone polyether copolymer comprises the following steps:
s1: adding octamethylcyclotetrasiloxane, tetramethylcyclotetrasiloxane, hexamethyldisiloxane and an acidic catalyst into a reactor according to a certain proportion, heating to a reaction temperature, and preserving heat for a certain time to prepare hydrogen-containing polymethylsiloxane;
s2: adding the prepared hydrogen-containing polymethylsiloxane, the terminal allyl polyether, the catalyst, the hindered amine and the antioxidant into a reactor, heating to a certain temperature under normal pressure, and reacting for a certain time under heat preservation to obtain the organic silicon polyether copolymer.
In step S1, the reaction temperature is 40-90 ℃ and the heat preservation time is 3-8 h.
In step S2, the reaction temperature is 65-120 ℃, the reaction time is 30-240min, and the catalyst dosage is 3-20ppm of the total material.
In step S2, the hindered amine is a secondary or tertiary amine containing a hydroxyl, carbonyl, or ether linkage.
The molecular formula of the hindered amine is as follows: NZxZ1yZ2z
Wherein: z can be H or alkyl with 1-13C, aryl with 4-10C or non-terminal alkenyl with 3-8C, and x is 0 or 1 or 2;
z1 is alkyl with 1-13C, aryl with 4-10C or non-terminal alkenyl with 3-8C, and y is 0 or 1;
z2 is a branched group of 2-3C, and Z is 1 or 2.
The hindered amine is at least one of diethanolamine, triethanolamine, acetamide, triethylamine, N-butylethanolamine, 2-aminobutanol, 1-diethylamino-3-butanone, and 5-diethylamino-2-pentanol.
The antioxidant is diphenylamine, hydroquinone, N-di-sec-butyl-p-phenylenediamine, propyl gallate, bis (2, 4-di-tert-butylphenol) pentaerythritol diphosphite, tert-butyl-p-hydroxyanisole, tris (2, 4-di-tert-butylphenyl) phosphite, 6- (4-hydroxy-3, 5-di-tert-butylphenyl) -2, 4-di-N-octylthio-1, 3, 5-triazine, pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], N-octadecyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ]), At least one of N, N-bis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine and isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate.
In step S2, the compounded hindered amine and the antioxidant are added before the reaction.
The compounding of the hindered amine and the antioxidant is the compounding of the hindered amine and at least one antioxidant and at most three antioxidants, the compounding ratio of the hindered amine to the antioxidant is 1: 2-15: 0-15, and the addition amount of the hindered amine and the antioxidant is 0.01-1% of the total mass of the product.
The invention has the beneficial technical effects that:
according to the organic silicon polyether copolymer and the preparation method thereof, the hindered amine and the antioxidant are compounded for use, so that the dehydropolycondensation and the formation of acetal are effectively controlled, the autoxidation of polyether is avoided, the generation of side reactions is reduced, the dosage of the catalyst can be reduced to a certain degree, and the reaction rate can be accelerated by adding the antioxidant in the reaction.
The invention provides an organic silicon polyether copolymer and a preparation method thereof. The compounding use of the sterically hindered amine and the antioxidant can reduce the using amount of the sterically hindered amine to a certain extent, and does not influence the inhibition effect on side reactions, thereby reducing the inhibition effect on main reactions and reducing the using amount of the catalyst.
Detailed Description
The present invention will be described in further detail below in order to make the technical solutions of the present invention more clear and definite to those skilled in the art, but the embodiments of the present invention are not limited thereto.
Example 1:
step 1: adding 106.28g of octamethylcyclotetrasiloxane, 50.92g of tetramethylcyclotetrasiloxane, 22.8g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 75 ℃, keeping the temperature for reacting for 8 hours after the temperature is stabilized, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: adding 31.0g of hydrogen-containing polymethylsiloxane, 101.33g of allyl polyether, 0.07g of N-butyl ethanolamine (B5), 0.45g of tris (2, 4-di-tert-butylphenyl) phosphite (A7) and 10ppm of catalyst into a three-neck flask, heating to 115 ℃ under normal pressure for reaction, generating heat when the reaction temperature is reached, keeping the temperature for reaction for 1H after 13min of transparency of the reaction liquid, detecting that the Si-H reaction is complete, cooling and cooling to obtain the organic silicon polyether copolymer with the viscosity of 375 mPas.
Example 2:
step 1: adding 106.28g of octamethylcyclotetrasiloxane, 50.92g of tetramethylcyclotetrasiloxane, 22.8g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 75 ℃, keeping the temperature for reacting for 8 hours after the temperature is stabilized, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: adding 31.0g of hydrogen-containing polymethylsiloxane, 101.33g of allyl-terminated polyether, 0.08g of 5-diethylamino-2-pentanol (B8), 0.99g of N, N-di-sec-butyl-p-phenylenediamine (A3) and 10ppm of catalyst into a three-neck bottle, heating to 115 ℃ under normal pressure for reaction, generating an exothermic phenomenon when the reaction temperature is reached, keeping the temperature for reaction for 1H after 9min of transparent reaction liquid, detecting that the Si-H reaction is complete, cooling and cooling to obtain the organic silicon polyether copolymer with the viscosity of 366 mPas.
Example 3:
step 1: adding 106.28g of octamethylcyclotetrasiloxane, 50.92g of tetramethylcyclotetrasiloxane, 22.8g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 75 ℃, keeping the temperature for reacting for 8 hours after the temperature is stabilized, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: adding 31.0g of hydrogen-containing polymethylsiloxane, 101.33g of terminal allyl polyether, 0.06g of 1-diethylamino-3-butanone (B7), 0.47g of beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) n-octadecyl propionate (A10) and 9ppm of catalyst into a three-neck flask, heating to 115 ℃ under normal pressure for reaction, generating an exothermic phenomenon when the reaction temperature is reached, allowing the reaction solution to be transparent for 22min, continuing to perform heat preservation reaction for 1H, detecting that the Si-H reaction is complete, cooling to obtain an organic silicon polyether copolymer with the viscosity of 361 mPas.
Example 4:
step 1: adding 144.81g of octamethylcyclotetrasiloxane, 24.98g of tetramethylcyclotetrasiloxane, 30.21g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 65 ℃, keeping the temperature for reaction for 9 hours after the temperature is stable, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: adding 50.0g of hydrogen-containing polymethylsiloxane, 70.13g of allyl polyether, 0.06g of 2-aminobutanol (B6), 0.58g of N, N-bis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine (A12) and 9ppm of catalyst into a three-neck flask, heating to 115 ℃ under normal pressure for reaction, generating an exothermic phenomenon when the reaction temperature is reached, allowing the reaction solution to be transparent within 17min, continuing to perform heat preservation reaction for 1H, detecting that the Si-H reaction is complete, cooling and cooling to obtain an organic silicon polyether copolymer with the viscosity of 272mPa & s.
Example 5:
step 1: adding 144.81g of octamethylcyclotetrasiloxane, 24.98g of tetramethylcyclotetrasiloxane, 30.21g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 65 ℃, keeping the temperature for reaction for 9 hours after the temperature is stable, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: 50.0g of hydrogen-containing polymethylsiloxane, 70.13g of allyl polyether, 0.02g of triethanolamine (B2), 0.14g of diphenylamine (A1), 0.14g of tris (2, 4-di-tert-butylphenyl) phosphite (A7) and 10ppm of catalyst are added into a three-neck flask, the mixture is heated to 115 ℃ under normal pressure to react, the exothermic phenomenon occurs when the reaction temperature is reached, the reaction solution is transparent for 10min, the heat preservation reaction is continued for 1H, the complete Si-H reaction is detected, and the organosilicon polyether copolymer is obtained after cooling, wherein the viscosity is 286mPa & s.
Example 6:
step 1: adding 144.81g of octamethylcyclotetrasiloxane, 24.98g of tetramethylcyclotetrasiloxane, 30.21g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 65 ℃, keeping the temperature for reaction for 9 hours after the temperature is stable, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: adding 50.0g of hydrogen-containing polymethylsiloxane, 70.13g of allyl polyether, 0.06g of acetamide (B3), 0.72g of tert-butyl p-hydroxyanisole (A6) and 9ppm of catalyst into a three-neck flask, heating to 115 ℃ under normal pressure to react, generating heat when the reaction temperature is reached, keeping the temperature for 1H after 15min of transparent reaction liquid, detecting that the Si-H reaction is complete, cooling and cooling to obtain the organic silicon polyether copolymer with the viscosity of 290mPa & s.
Comparative example 1:
step 1: adding 106.28g of octamethylcyclotetrasiloxane, 50.92g of tetramethylcyclotetrasiloxane, 22.8g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 75 ℃, keeping the temperature for reaction for 8 hours after the temperature is stable, and preparing hydrogen-containing polymethylsiloxane;
step 2: adding 31.0g of hydrogen-containing polymethylsiloxane, 101.33g of allyl-terminated polyether and 10ppm of catalyst into a three-neck flask, heating to 115 ℃ under normal pressure for reaction, generating heat when the reaction temperature is reached, keeping the temperature for reaction for 1H after 20min is transparent, detecting that the Si-H reaction is complete, cooling and cooling to obtain the organic silicon polyether copolymer with the viscosity of 988mPa & s.
Comparative example 2:
step 1: adding 106.28g of octamethylcyclotetrasiloxane, 50.92g of tetramethylcyclotetrasiloxane, 22.8g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 75 ℃, keeping the temperature for reacting for 8 hours after the temperature is stabilized, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: adding 31.0g of hydrogen-containing polymethylsiloxane, 101.33g of allyl polyether, 0.07g of N-butyl ethanolamine (B5) and 12ppm of catalyst into a three-neck flask, heating to 115 ℃ under normal pressure for reaction, generating heat when the reaction temperature is reached, keeping the temperature for reaction for 1H after 25min, detecting that the Si-H reaction is complete, cooling and cooling to obtain the organic silicon polyether copolymer with the viscosity of 400 mPas.
Comparative example 3:
step 1: adding 106.28g of octamethylcyclotetrasiloxane, 50.92g of tetramethylcyclotetrasiloxane, 22.8g of hexamethyldisiloxane and a certain amount of acid catalyst into a three-necked bottle, heating to 75 ℃, keeping the temperature for reacting for 8 hours after the temperature is stabilized, cooling and filtering to obtain hydrogenous polymethylsiloxane;
step 2: 31.0g of hydrogen-containing polymethylsiloxane, 101.33g of allyl polyether, 0.45g of tris (2, 4-di-tert-butylphenyl) phosphite (A7) and 10ppm of catalyst are added into a three-neck flask, the three-neck flask is heated to 115 ℃ under normal pressure to react, the exothermic phenomenon occurs when the reaction temperature is reached, the reaction solution is transparent after 20min, the heat preservation reaction is continued for 1H, the complete reaction of Si-H is detected, and the organosilicon polyether copolymer with the viscosity of 682 mPas is obtained after cooling.
In the above examples, the effect of compounding hindered amine with antioxidant on hydrosilylation reaction is shown in table 1:
TABLE 1 Effect of compounding hindered amine with antioxidant on hydrosilylation reaction
In the above embodiment, as shown in table 1, the hindered amine and the antioxidant are compounded according to a certain ratio, and then added into a hydrosilylation reaction system, so that the dehydropolycondensation and the formation of acetal are effectively inhibited, the auto-oxidation reaction of polyether is avoided, the generation of side reactions is reduced, the use amounts of the hindered amine and the catalyst can be reduced to a certain extent, and the inhibition effect on the side reactions is not affected.
The above description is only for the purpose of illustrating the present invention and is not intended to limit the scope of the present invention, and any person skilled in the art can substitute or change the technical solution of the present invention and its conception within the scope of the present invention.
Claims (9)
1. A preparation method of an organic silicon polyether copolymer is characterized in that the structure of the organic silicon polyether copolymer is as follows:
wherein: the value of m is 8-70, the value of n = is 0-15, and m + n = 10-90;
the structure of R is: -CH2CH2CH2O(CH2CH2O)a(CH2CH(CH3)O)bR1A is 0 to 20, b is 1 to 20, a + b is 1 to 20, R1Alkyl with 1-4 carbon atoms or hydrogen;
the preparation method comprises the following steps:
s1: adding octamethylcyclotetrasiloxane, tetramethylcyclotetrasiloxane, hexamethyldisiloxane and an acidic catalyst into a reactor according to a certain proportion, heating to a reaction temperature, and preserving heat for a certain time to prepare hydrogen-containing polymethylsiloxane;
s2: adding the prepared hydrogen-containing polymethylsiloxane, the terminal allyl polyether, the catalyst, the hindered amine and the antioxidant into a reactor, heating to a certain temperature under normal pressure, and reacting for a certain time under heat preservation to obtain the organic silicon polyether copolymer.
2. The method of claim 1, wherein in step S1, the reaction temperature is 40-90 ℃ and the holding time is 3-8 h.
3. The method of claim 1, wherein in step S2, the reaction temperature is 65-120 ℃, the reaction time is 30-240min, and the amount of the catalyst is 3-20ppm of the total amount of the materials.
4. The method of claim 1, wherein in step S2, the hindered amine is a secondary or tertiary amine containing hydroxyl, carbonyl or ether linkages.
5. The method of claim 4, wherein the hindered amine has the formula: NZxZ1yZ2z
Wherein: z is H or alkyl with 1-13C, aryl with 4-10C or non-terminal alkenyl with 3-8C, and x is 0 or 1 or 2;
z1 is alkyl with 1-13C, aryl with 4-10C or non-terminal alkenyl with 3-8C, and y is 0 or 1;
z2 is a branched group of 2-3C, and Z is 1 or 2.
6. The method of claim 4, wherein the hindered amine is at least one of diethanolamine, triethanolamine, acetamide, triethylamine, N-butylethanolamine, 2-aminobutanol, 1-diethylamino-3-butanone, and 5-diethylamino-2-pentanol.
7. The method of claim 1, wherein the antioxidant is diphenylamine, hydroquinone, N-di-sec-butyl-p-phenylenediamine, propyl gallate, bis (2, 4-di-tert-butylphenol) pentaerythritol diphosphite, tert-butyl-p-hydroxyanisole, tris (2, 4-di-tert-butylphenyl) phosphite, 6- (4-hydroxy-3, 5-di-tert-butylphenylamino) -2, 4-di-N-octylthio-1, 3, 5-triazine, pentaerythrityl tetrakis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], N-octadecyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 2-thiobis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], N-bis [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine and isooctyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate.
8. The method of claim 1, wherein in step S2, the formulated hindered amine and the antioxidant are added before the reaction.
9. The preparation method of the organic silicon polyether copolymer as claimed in claim 8, wherein the compounding of the hindered amine and the antioxidant is the compounding of the hindered amine and at least one antioxidant and at most three antioxidants, the compounding ratio of the hindered amine to the antioxidant is 1 (2-15) to (0-15), and the addition amount of the hindered amine and the antioxidant is 0.01-1% of the total mass of the product.
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| CN111040175A (en) * | 2019-12-26 | 2020-04-21 | 江苏美思德化学股份有限公司 | Polyether modified siloxane and synthesis method thereof |
| CN111004396B (en) * | 2019-12-27 | 2022-07-05 | 江苏美思德化学股份有限公司 | Tertiary amino modified organic silicon polyether copolymer and preparation method and application thereof |
| CN113024798B (en) * | 2021-03-01 | 2024-01-16 | 浙江润禾有机硅新材料有限公司 | Modified organosilicon hydrogen addition continuous production method and equipment |
| CN113024818B (en) * | 2021-03-01 | 2022-07-08 | 浙江润禾有机硅新材料有限公司 | Preparation method of high-purity low-byproduct polyether modified siloxane |
| CN113234313B (en) * | 2021-06-01 | 2022-10-21 | 上海抚佳精细化工有限公司 | Antioxidant composition and allyl polyether treatment method |
| CN113461970B (en) * | 2021-07-26 | 2022-07-12 | 浙江新安化工集团股份有限公司 | Organic silicon wax emulsion and preparation method thereof |
| CN116804086B (en) * | 2023-08-25 | 2023-11-07 | 成都思立可科技有限公司 | Long-chain alkyl-polar group co-modified polysiloxane and preparation method thereof |
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