CN109867790A - A kind of organic silicon polyether copolymer and preparation method thereof - Google Patents
A kind of organic silicon polyether copolymer and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of preparation methods of organic silicon polyether copolymer, belong to organic silicon surfactant technical field, in order to solve the problems, such as that side reaction is more, not easy to control during hydrosilylation in the prior art, octamethylcy-clotetrasiloxane, tetramethyl-ring tetrasiloxane and hexamethyldisiloxane and acidic catalyst are added in reactor by a certain percentage, it is warming up to reaction temperature, keeps the temperature and hydrogen containing polysiloxane is made；The hydrogen containing polysiloxane of preparation, allyl-terminated polyether, catalyst, bulky amine and antioxidant are added in reactor, certain temperature is heated under normal pressure, keeps the temperature and organic silicon polyether copolymer is made.The present invention is used in compounding by using bulky amine and antioxidant, the not only effectively formation of control dehydrogenation polycondensation and acetal, avoids the autoxidation for generating polyethers, reduces the generation of side reaction, catalyst amount can be reduced to a certain extent simultaneously, and antioxidant is added in the reaction can accelerate reaction rate.
Description
Technical field
The present invention relates to a kind of copolymers and preparation method thereof, more particularly to a kind of organic silicon polyether copolymer and its system
Preparation Method belongs to organic silicon surfactant technical field.
Background technique
Organic silicon surfactant is used as extensively with its water solubility, compatibility, emulsibility and surface-active outstanding
Foam stabilizer, soft finishing agent, efficient emulsifier, defoaming agent, coating wetting agent, plastic additive, personal care products raw material and
Auxiliary agent etc..But in hydrosilylation, when unsaturated end group compound contains hydroxyl, it is prone to dehydrogenation polycondensation and
The side reactions such as acetal, polyethers autoxidation are formed, the performance of product is seriously affected.In order to reduce the influence of side reaction, researcher
It is discovered by experiment that some substances are added during hydrosilylation can effectively control side reaction, the choosing of reaction is improved
Selecting property increases the water solubility of product to reduce product viscosity.
United States Patent (USP) US6372874B1, United States Patent (USP) US5191103, United States Patent (USP) US20150105576A1 and the U.S. are special
Sharp US20160160009A1 etc. discloses a kind of method that side reaction is controlled in hydrosilylation, which is characterized in that contain
Hydroxyl, the secondary amine of carbonyl or ehter bond or tertiary amine are added in reaction system by a certain percentage, add as catalyst buffer
Hot temperature reaction after a certain period of time obtain low viscosity product, the formation of the by-products such as dehydrogenation polycondensation and acetal is effectively reduced.Europe
Continent patent EP0314903, United States Patent (USP) US005159096A, United States Patent (USP) US4847398 etc. are disclosed using carboxylic acid or carboxylic acid
Salt avoids the use of traditional handicraft solvent as hydrosilylation additive, effectively acetal is inhibited to be formed, however metal carboxylate
Additive inhibits main reaction to a certain extent, causes to need more catalyst, induction period is longer, and product colour is deeper.
Yu Qiong etc. analyzes the Auto-oxidation reaction of polyethers and its influence for hydrosilylation process, has studied and adds
Enter antioxidant pretreatment polyethers for the control action of cross-linking by-products content in product, the results showed that antioxidant gallic acid third
Ester is best to the inhibitory effect of side reaction, and in 2% (wt) that additional amount is polyethers total amount, treatment temperature is 80 DEG C, handles the time
For the content that can significantly reduce cross-linking agent in product under conditions of 1h.
The above method is although the side reaction in hydrosilylation can be controlled effectively, for the hydrogeneous poly- of high hydrogen content
Methyl hydrogen siloxane is easy to happen crosslinking side reaction in hydrosilylation, only individually uses a kind of bulky amine or antioxidant not
By-product generation can be effectively reduced, though or the progress of side reaction can be effectively reduced under excessive bulky amine dosage, can also press down
Main reaction speed processed, causes catalyst amount to be promoted, and increases production cost；Though in addition, antioxygen agent addition agent can effectively reduce it is poly-
The Auto-oxidation reaction of ether, but it is relatively weak for dehydrogenation polycondensation and acetal formation side reaction inhibiting effect, and reaction yield is low, produces
Product viscosity is big.
Summary of the invention
The main object of the present invention is that side reaction is more, not easy to control during solving hydrosilylation in the prior art
The problem of, and a kind of preparation method of organic silicon polyether copolymer is provided.
The purpose of the present invention can reach by using following technical solution:
A kind of organic silicon polyether copolymer, the structure of the organic silicon polyether copolymer are as follows:
Wherein: the value that the value of m is 8~70, n=is 0~15, m+n=10~90；
The structure of R are as follows:-CH2CH2CH2O(CH2CH2O)a(CH2CH(CH3)O)bR1, the value that the value of a is 0~20, b is 1~
20, a+b value is 1~20, R1For the alkyl or hydrogen of 1~4 carbon atom number.
A kind of preparation method of organic silicon polyether copolymer, includes the following steps:
S1: octamethylcy-clotetrasiloxane, tetramethyl-ring tetrasiloxane and hexamethyldisiloxane and acidic catalyst are pressed
Certain proportion is added in reactor, is warming up to reaction temperature, and hydrogen containing polysiloxane is made in held for some time；
S2: the hydrogen containing polysiloxane of preparation, allyl-terminated polyether, catalyst, bulky amine and antioxidant are added to
In reactor, certain temperature is heated under normal pressure, organic silicon polyether copolymer is made in insulation reaction certain time.
In step S1, reaction temperature is 40-90 DEG C, soaking time 3-8h.
In step S2, reaction temperature is 65-120 DEG C, reaction time 30-240min, and catalyst amount is total inventory
3-20ppm.
In step S2, bulky amine is secondary amine or tertiary amine containing hydroxyl, carbonyl or ehter bond.
Bulky amine molecular formula is as follows: NZxZ1yZ2z
Wherein: Z can be the alkyl of H or 1~13 C or the non-end alkenyl of the aryl of 4~10 C or 3~8 C, x 0
Or 1 or 2；
The non-end alkenyl of the aryl or 3~8 C of alkyl that Z1 is 1~13 C or 4~10 C, y is 0 or 1；
Z2 is the branched group of 2~3 C, and z is 1 or 2.
Bulky amine is diethanol amine, triethanolamine, acetamide, triethylamine, N- butylethanolamine, 2- amino butanol, 1- bis-
At least one of ethylamino- -3- butanone and 5- diethyl amido -2- amylalcohol.
Antioxidant is diphenylamines, hydroquinone, N, N- di-sec-butyl-p-phenyl enediamine, propylgallate, bis- (bis- uncles of 2,4-
Butylphenol) pentaerythritol diphosphites, butylated hydroxyarisol, three (2,4- di-tert-butyl-phenyl) phosphite esters,
The just pungent sulfenyl -1,3,5-triazines of 6- (4- hydroxyl -3,5- di-t-butyl phenylamino) -2,4- bis-, four [β-(3,5- di-t-butyl -4-
Hydroxy phenyl) propionic acid] pentaerythritol ester, β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid n-octadecyl alcohol ester, 2,2- be thio
Bis- [3- (3,5- di-tert-butyl-hydroxy phenyl) propionic esters], N, N- bis- [β-(3,5- di-tert-butyl-hydroxy phenyl) propionyl]
At least one of hydrazine and β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid isoctanol ester.
In step S2, the bulky amine of compounding is added before the reaction with antioxidant.
Bulky amine compounds for a kind of bulky amine at least one, most three kinds of antioxidant with compounding for antioxidant, steric hindrance
The compounding of amine and antioxidant is compared for 1:2~15:0~15:0~15, and the additional amount of bulky amine and antioxidant is product gross mass
0.01%~1%.
Advantageous effects of the invention:
A kind of organic silicon polyether copolymer provided by the invention and preparation method thereof, it is multiple by using bulky amine and antioxidant
With use, the effective formation for controlling dehydrogenation polycondensation and acetal avoids the autoxidation for generating polyethers, reduces the generation of side reaction,
Catalyst amount can be reduced to a certain extent simultaneously, and antioxidant is added in the reaction can accelerate reaction rate.
A kind of organic silicon polyether copolymer provided by the invention and preparation method thereof, first by bulky amine and antioxidant by certain
Ratio compounding, be then added in hydrosilylation system, inhibit dehydrogenation polycondensation and acetal to be formed, reduce the automatic of polyethers
Oxidation reaction prepares organosilicon copolyether.Bulky amine and being used in compounding for antioxidant can be to a certain extent in the present invention
Bulky amine dosage is reduced, and does not influence the inhibitory effect to side reaction, to reduce the inhibiting effect to main reaction, reduces catalysis
Agent dosage is accelerated in addition, antioxidant employed in the present invention can also promote the progress of hydrosilylation to a certain extent
Reaction speed.
Specific embodiment
To make the more clear and clear technical solution of the present invention of those skilled in the art, the present invention is made below further
Detailed description, embodiments of the present invention are not limited thereto.
Embodiment 1:
Step 1: by 106.28g octamethylcy-clotetrasiloxane, 50.92g tetramethyl-ring tetrasiloxane, 22.8g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 75 DEG C, the insulation reaction after temperature is stablized
8h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 31.0g hydrogen containing polysiloxane, 101.33g allyl-terminated polyether, 0.07gN- butylethanolamine
(B5) it is added in there-necked flask with 0.45g tri- (2,4- di-tert-butyl-phenyl) phosphite ester (A7) and 10ppm catalyst, under normal pressure
115 DEG C of reactions are heated to, exothermic phenomenon occur when reaching reaction temperature, 13min reaction solution is transparent, continues insulation reaction
1h detects Si-H fully reacting, cools to obtain organic silicon polyether copolymer, viscosity 375mPas.
Embodiment 2:
Step 1: by 106.28g octamethylcy-clotetrasiloxane, 50.92g tetramethyl-ring tetrasiloxane, 22.8g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 75 DEG C, the insulation reaction after temperature is stablized
8h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 31.0g hydrogen containing polysiloxane and 101.33g allyl-terminated polyether, 0.08g5- diethyl amido-
2- amylalcohol (B8) and 0.99gN, N- di-sec-butyl-p-phenyl enediamine (A3) and 10ppm catalyst are added in there-necked flask, are added under normal pressure
Heat is warming up to 115 DEG C of reactions, exothermic phenomenon occurs when reaching reaction temperature, and 9min reaction solution is transparent, continues insulation reaction 1h, inspection
Si-H fully reacting is surveyed, cools to obtain organic silicon polyether copolymer, viscosity 366mPas.
Embodiment 3:
Step 1: by 106.28g octamethylcy-clotetrasiloxane, 50.92g tetramethyl-ring tetrasiloxane, 22.8g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 75 DEG C, the insulation reaction after temperature is stablized
8h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 31.0g hydrogen containing polysiloxane and 101.33g allyl-terminated polyether, 0.06g1- diethylin -3-
Butanone (B7) adds with 0.47g β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid n-octadecyl alcohol ester (A10) and 9ppm catalyst
Enter into there-necked flask, 115 DEG C of reactions are heated under normal pressure, exothermic phenomenon, 22min reaction solution occurs when reaching reaction temperature
It is transparent, continue insulation reaction 1h, detects Si-H fully reacting, cool to obtain organic silicon polyether copolymer, viscosity is
361mPa·s。
Embodiment 4:
Step 1: by 144.81g octamethylcy-clotetrasiloxane, 24.98g tetramethyl-ring tetrasiloxane, 30.21g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 65 DEG C, the insulation reaction after temperature is stablized
9h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 50.0g hydrogen containing polysiloxane and 70.13g allyl-terminated polyether, 0.06g2- amino butanol (B6)
With 0.58gN, bis- [β-(3, the 5- di-tert-butyl-hydroxy phenyl) propionyl] hydrazines (A12) of N- and 9ppm catalyst are added to there-necked flask
In, it is heated to 115 DEG C of reactions under normal pressure, exothermic phenomenon occurs when reaching reaction temperature, 17min reaction solution is transparent, continues
Insulation reaction 1h detects Si-H fully reacting, cools to obtain organic silicon polyether copolymer, viscosity 272mPas.
Embodiment 5:
Step 1: by 144.81g octamethylcy-clotetrasiloxane, 24.98g tetramethyl-ring tetrasiloxane, 30.21g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 65 DEG C, the insulation reaction after temperature is stablized
9h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 50.0g hydrogen containing polysiloxane, 70.13g allyl-terminated polyether, 0.02g triethanolamine (B2) with
0.14g diphenylamines (A1) and 0.14g tri- (2,4- di-tert-butyl-phenyl) phosphite ester (A7) and 10ppm catalyst are added to three mouthfuls
In bottle, it is heated to 115 DEG C of reactions under normal pressure, exothermic phenomenon occurs when reaching reaction temperature, 10min reaction solution is transparent, after
Continuous insulation reaction 1h, detects Si-H fully reacting, cools to obtain organic silicon polyether copolymer, viscosity 286mPas.
Embodiment 6:
Step 1: by 144.81g octamethylcy-clotetrasiloxane, 24.98g tetramethyl-ring tetrasiloxane, 30.21g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 65 DEG C, the insulation reaction after temperature is stablized
9h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 50.0g hydrogen containing polysiloxane, 70.13g allyl-terminated polyether, 0.06 acetamide (B3) with
0.72g butylated hydroxyarisol (A6) and 9ppm catalyst are added in there-necked flask, and 115 DEG C are heated under normal pressure instead
It answers, exothermic phenomenon occurs when reaching reaction temperature, 15min reaction solution is transparent, continues insulation reaction 1h, and detection Si-H has reacted
Entirely, it cools to obtain organic silicon polyether copolymer, viscosity 290mPas.
Comparative example 1:
Step 1: by 106.28g octamethylcy-clotetrasiloxane, 50.92g tetramethyl-ring tetrasiloxane, 22.8g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 75 DEG C, the insulation reaction after temperature is stablized
Hydrogen containing polysiloxane is made in 8h；
Step 2: 31.0g hydrogen containing polysiloxane, 101.33g allyl-terminated polyether and 10ppm catalyst are added to
In there-necked flask, it is heated to 115 DEG C of reactions under normal pressure, exothermic phenomenon occurs when reaching reaction temperature, 20min reaction solution is saturating
It is bright, continue insulation reaction 1h, detects Si-H fully reacting, cool to obtain organic silicon polyether copolymer, viscosity is
988mPa·s。
Comparative example 2:
Step 1: by 106.28g octamethylcy-clotetrasiloxane, 50.92g tetramethyl-ring tetrasiloxane, 22.8g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 75 DEG C, the insulation reaction after temperature is stablized
8h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 31.0g hydrogen containing polysiloxane, 101.33g allyl-terminated polyether, 0.07gN- butylethanolamine
(B5) it is added in there-necked flask with 12ppm catalyst, 115 DEG C of reactions is heated under normal pressure, occurred when reaching reaction temperature
Exothermic phenomenon, 25min reaction solution is transparent, continues insulation reaction 1h, detects Si-H fully reacting, and it is poly- to cool to obtain organosilicon
Ether copolymer, viscosity 400mPas.
Comparative example 3:
Step 1: by 106.28g octamethylcy-clotetrasiloxane, 50.92g tetramethyl-ring tetrasiloxane, 22.8g hexamethyl two
Siloxanes and a certain amount of acidic catalyst are added in there-necked flask, are heated to 75 DEG C, the insulation reaction after temperature is stablized
8h, cooling, which is filtered, is made hydrogen containing polysiloxane；
Step 2: by 31.0g hydrogen containing polysiloxane, 101.33g allyl-terminated polyether, (the tertiary fourth of 2,4- bis- of 0.45g tri-
Base phenyl) phosphite ester (A7) and 10ppm catalyst be added in there-necked flask, 115 DEG C of reactions be heated under normal pressure, are reached
Occurs exothermic phenomenon when reaction temperature, 20min reaction solution is transparent, continues insulation reaction 1h, detects Si-H fully reacting, cooling drop
Temperature obtains organic silicon polyether copolymer, viscosity 682mPas.
In the above-described embodiments, influence of the compounding bulky amine and antioxidant to hydrosilylation is as shown in table 1:
Table 1 compounds the influence of bulky amine and antioxidant to hydrosilylation
In the above-described embodiments, in conjunction with shown in table 1, by compounding bulky amine according to a certain percentage with antioxidant, then
It is added in hydrosilylation system, the effective formation for inhibiting dehydrogenation polycondensation and acetal avoids the autoxidation of polyethers anti-
It answers, reduces the generation of side reaction, while the dosage of bulky amine and catalyst can be reduced to a certain extent, and do not influence to secondary anti-
The inhibitory effect answered can also promote the progress of hydrosilylation using antioxidant in the present invention to a certain extent, accelerate anti-
Answer rate.
The above, further embodiment only of the present invention, but scope of protection of the present invention is not limited thereto, and it is any
Within the scope of the present disclosure, according to the technique and scheme of the present invention and its design adds those familiar with the art
With equivalent substitution or change, protection scope of the present invention is belonged to.
Claims (10)
1. a kind of organic silicon polyether copolymer, which is characterized in that the structure of the organic silicon polyether copolymer is as follows:
Wherein: the value that the value of m is 8~70, n=is 0~15, m+n=10~90；
The structure of R are as follows:-CH2CH2CH2O(CH2CH2O)a(CH2CH(CH3)O)bR1, the value that the value of a is 0~20, b is 1~20, a+b
Value be 1~20, R1For the alkyl or hydrogen of 1~4 carbon atom number.
2. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 2, which is characterized in that including walking as follows
It is rapid:
S1: by octamethylcy-clotetrasiloxane, tetramethyl-ring tetrasiloxane and hexamethyldisiloxane and acidic catalyst by certain
Ratio is added in reactor, is warming up to reaction temperature, and hydrogen containing polysiloxane is made in held for some time；
S2: the hydrogen containing polysiloxane of preparation, allyl-terminated polyether, catalyst, bulky amine and antioxidant are added to reaction
In device, certain temperature is heated under normal pressure, organic silicon polyether copolymer is made in insulation reaction certain time.
3. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 2, which is characterized in that in step S1, instead
Answering temperature is 40-90 DEG C, soaking time 3-8h.
4. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 2, which is characterized in that in step S2, instead
Answering temperature is 65-120 DEG C, reaction time 30-240min, and catalyst amount is the 3-20ppm of total inventory.
5. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 2, which is characterized in that in step S2, position
Hindering amine is secondary amine or tertiary amine containing hydroxyl, carbonyl or ehter bond.
6. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 5, which is characterized in that bulky amine molecular formula
It is as follows: NZxZ1yZ2z
Wherein: Z can be the alkyl of H or 1~13 C or the non-end alkenyl of the aryl of 4~10 C or 3~8 C, and x is 0 or 1
Or 2；
The non-end alkenyl of the aryl or 3~8 C of alkyl that Z1 is 1~13 C or 4~10 C, y is 0 or 1；
Z2 is the branched group of 2~3 C, and z is 1 or 2.
7. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 5, which is characterized in that bulky amine is diethyl
Hydramine, triethanolamine, acetamide, triethylamine, N- butylethanolamine, 2- amino butanol, 1- diethylin -3- butanone and 5- diethyl
At least one of base amido -2- amylalcohol.
8. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 2, which is characterized in that antioxidant is hexichol
Amine, hydroquinone, N, N- di-sec-butyl-p-phenyl enediamine, propylgallate, bis- (2,4- DI-tert-butylphenol compounds) pentaerythrites two
Phosphite ester, butylated hydroxyarisol, three (2,4- di-tert-butyl-phenyl) phosphite esters, 6- (the tertiary fourth of 4- hydroxyl -3,5- two
Base phenylamino) the just pungent sulfenyl -1,3,5-triazines of -2,4- bis-, four [β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid] Ji Wusi
Alcohol ester, β-(3,5- di-tert-butyl-hydroxy phenyl) propionic acid n-octadecyl alcohol ester, 2,2- thiobis [3- (3,5- di-t-butyl-
4- hydroxy phenyl) propionic ester], N, bis- [β-(3, the 5- di-tert-butyl-hydroxy phenyl) propionyl] hydrazines of N- and β-(3,5- bis- tertiary fourths
At least one of base -4- hydroxy phenyl) propionic acid isoctanol ester.
9. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 2, which is characterized in that multiple in step S2
The bulky amine matched is added before the reaction with antioxidant.
10. a kind of preparation method of organic silicon polyether copolymer as claimed in claim 9, which is characterized in that bulky amine and anti-
The compounding of oxygen agent is that a kind of bulky amine is compounded at least one, most three kinds of antioxidant, and bulky amine compounds ratio with antioxidant
For 1:2~15:0~15:0~15, the additional amount of bulky amine and antioxidant is the 0.01%~1% of product gross mass.
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| CN111004396A (en) * | 2019-12-27 | 2020-04-14 | 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 |
| 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 |
| CN113024818A (en) * | 2021-03-01 | 2021-06-25 | 浙江润禾有机硅新材料有限公司 | Preparation method of high-purity low-byproduct polyether modified siloxane |
| CN113024798A (en) * | 2021-03-01 | 2021-06-25 | 浙江润禾有机硅新材料有限公司 | Continuous production method and equipment for modified organic silicon hydrogen addition |
| CN113234313A (en) * | 2021-06-01 | 2021-08-10 | 上海抚佳精细化工有限公司 | Antioxidant composition and allyl polyether treatment method |
| CN113461970A (en) * | 2021-07-26 | 2021-10-01 | 浙江新安化工集团股份有限公司 | Organic silicon wax emulsion and preparation method thereof |
| CN116804086A (en) * | 2023-08-25 | 2023-09-26 | 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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