CN110423351A - A kind of Vinyl MQ silicon resin and preparation method thereof - Google Patents
A kind of Vinyl MQ silicon resin and preparation method thereof Download PDFInfo
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- CN110423351A CN110423351A CN201910688859.9A CN201910688859A CN110423351A CN 110423351 A CN110423351 A CN 110423351A CN 201910688859 A CN201910688859 A CN 201910688859A CN 110423351 A CN110423351 A CN 110423351A
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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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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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
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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Abstract
The invention discloses a kind of Vinyl MQ silicon resins and preparation method thereof, are made of the component of following mass fraction meter: 30~50 parts of tetra functional silicon monomer;3~20 parts of vinyl silicane coupling agent;0.1~15 part of catalyst;1~20 part of alcohol;5~30 parts of deionized water;5~30 parts of siloxane blocking agent.The Vinyl MQ silicon resin molecular weight that the present invention synthesizes more is concentrated, and product purity is higher, and various physical properties, chemical property are excellent, can effectively improve the peeling force of the filler of Silicone pressure sensitive glue, is had outstanding hydrophobic property, be can be applied to water-repellent paint.
Description
Technical field
The invention belongs to organosilicon technical fields, and in particular to a kind of Vinyl MQ silicon resin and preparation method thereof.
Background technique
MQ silicone resin is a kind of special polyorganosiloxane resin, is one kind by simple function group (abbreviation M group) organosilicon oxygen
Alkane closes chain link R3SiO1/2With four-functional group (abbreviation Q group) organosiloxane chain link SiO2Condensation is hydrolyzed, with Si-O key
The polysiloxane of highly branched solid (non-linear) structure constituted for skeleton.Due to synthesis condition and the kind that feeds intake
Class, the difference of ratio, obtained MQ silicone resin often have different physical property and chemical property, and basis herein
On can add multiple functions group MQ silicone resin is modified, relatively common having introduces aromatic compound, annelation
Object is closed, for changing the refractive index in its physical property;Also have and change resisting in its physical property by adding heavy metal element
Impact;It introduces aliphatic compound and improves its transmissivity etc..The property and high-molecular organic material, inorganic height of MQ silicone resin
Molecular material has larger difference, therefore is generally acknowledged that its property falls between, unapproachable resistance to general resin
The chemical properties such as burn into high temperature resistant, hydrophobic.In addition, MQ silicone resin also has a series of excellent physical properties, and such as: it is mechanical
Intensity is big, insulation performance is strong, heat resistance is stable, has preferable flexibility with some strength, is easy film forming
The features such as good with cementability.In addition, MQ silicone resin industrially also has very big application value, it is mainly used as Silicone pressure sensitive
The filler of glue, the reinforced filling of add-on type liquid silicon rubber, aqueous laminating adhesive defoaming agent and tackifier.Using MQ silicone resin as base
Material, the various products such as insullac, laminated material, moulding compound, anti-blushing agent and remover for being made into using its physical property are being changed
The fields such as cosmetic, electronics, electric appliance, motor, aviation and building all have been widely used.There are mainly two types of prepare MQ silicon at present
The method of resin, one of method are sodium metasilicate methods, which has cost of material low and be easy to get, and have business
The advantages of feasibility, but the preparation method has easy gelation in reaction process, the relatively low disadvantage of yield;There are also a kind of sides
Method is ethyl orthosilicate method, its advantage is that yield is higher, is not easy gel, but prepared by Vinyl MQ silicon resin in the prior art
During that there are side reactions is more, the MQ silicone resin molecular weight distribution of synthesis is wider, and what the ratio of M/Q can not be controlled effectively asks
Topic, so that the application of the MQ silicone resin of synthesis in actual production is restricted.
United States Patent (USP) US4707531A reports the influence of MQ ratio, during the reaction, by controlling feed ratio, one
Determine adjustable MQ ratio in degree, the structure proportion of final product is regulated and controled.United States Patent (USP) US2857356A report
The influence of water and solvent for last MQ silicone resin, the addition sequence and dosage of water and solvent can all influence last molecule
Amount.
Summary of the invention
To solve the shortcomings and deficiencies of the prior art, the primary purpose of the present invention is that providing a kind of vinyl MQ silicon
Resin.
To achieve the above object, The technical solution adopted by the invention is as follows:
A kind of Vinyl MQ silicon resin, the component including following mass fraction meter are made:
Preferably, the tetra functional silicon monomer is at least one in sodium metasilicate, methyl orthosilicate and ethyl orthosilicate
Kind.
Preferably, the vinyl silicane coupling agent is vinyltriethoxysilane, vinyl methyl diethoxy
At least one of silane, vinyl benzene radical siloxane and dimethoxy-methyl vinylsiloxane.
Preferably, the catalyst is at least one of hydrochloric acid, sulfuric acid, p-methyl benzenesulfonic acid.
Preferably, the alcohol is ethyl alcohol, 1- propyl alcohol, n-butyl alcohol, 1- propyl alcohol, 1- amylalcohol, 2- propyl alcohol, 2- amylalcohol and hexamethylene
At least one of alcohol.
Preferably, the siloxane blocking agent is hexamethyldisiloxane, hexaphenyldisiloxane base, methoxyl group front three
At least one of base silane, hexamethyldisilazane and trimethylethoxysilane.
Another object of the present invention is to provide a kind of preparation methods of Vinyl MQ silicon resin, by following technical solution
It realizes:
A kind of specific preparation method of Vinyl MQ silicon resin, comprising the following steps:
(1) deionized water, catalyst, pure and mild siloxane blocking agent are sequentially added in the reaction vessel in 30 DEG C~60 DEG C items
0.5h~2h is stirred to react under part;
(2) tetra functional silicon monomer and vinyl silicane coupling agent are slowly added dropwise on the basis of step (1), controls temperature
At 40 DEG C~60 DEG C, time for adding is controlled in 0.5h~3h, after being added dropwise, continues to be stirred to react 2h~6h;
(3) continue to increase reaction temperature on the basis of step (2) to 60 DEG C~75 DEG C, react 0.5h~2h;
(4) solution in step (3) is extracted, is washed, revolving and vacuum drying remove solvent and low-boiling-point substance, obtain
Final product Vinyl MQ silicon resin.
Preferably, acid starts to carry out siloxanes envelope after being used as catalyst, material to touch catalyst in the step (1)
Agent hydrolysis is held, hydrolysate, which is conducive to reaction, to carry out, therefore the charging sequence should be noted that and deionized water is first added,
In the case where adding catalyst, pure and mild siloxane blocking agent, obtained Vinyl MQ silicon resin is not likely to produce gel.
Preferably, due to tetra functional monomer and vinyl silicane coupling agent easily water in air in the step (2)
Solution, should quickly weigh in dry and ventilated cupboard, and after weighing, stirring magneton be added, sealing prevents from being exposed at once
Denaturation is hydrolyzed in air;If tetra functional monomer and vinyl silicane coupling agent rate of addition is too fast or rate of addition variation
Larger, may cause in reaction process has gel generation, and the MQ silicone resin molecular weight distribution of generation is larger, using wriggling when dropwise addition
Pump is to control constant slow rate of addition;The process of the mixed liquor of tetra functional silicon monomer and vinyl silicane coupling agent is added dropwise
It is middle to use magnetic agitation, it is added dropwise while stirring, the solution composition for controlling mixed liquor is evenly distributed.
Preferably, in the step (3) after reaction carries out to a certain extent, temperature is increased, the raising of yield is conducive to.
Preferably, the organic solvent that toluene, acetone etc. can be selected outstanding in extraction in the step (4), but be
The silicon of the same race that the last purity of product is pursued with stability, in the invention solvent selection and previous experiments as one of raw material
Oxygen alkane end-capping reagent is (for example, end-capping reagent uses trimethylethoxysilane in experiment, then last extractant also uses trimethyl
Ethoxysilane);Extract layer is washed to neutrality with deionized water when washing;It is subsequent in order to accelerate after washing terminates
Experimental procedure carries out, and desiccant appropriate can be added in extract layer, and in order to avoid introducing impurity, desiccant type is because of catalysis
Depending on agent type.(for example, catalyst uses the concentrated sulfuric acid, then should select corresponding sulfate when selection desiccant
Class desiccant, should be at (50 DEG C~80 DEG C) using bath temperature in revolving, and in order to increase revolving surface area, the revolving of selection turns
Speed is answered slightly larger, and the revolving revolving speed of selection is 4~6 grades of EYELA N-1100 type Rotary Evaporators, when revolving (5min~1h) revolving
Between be (5min~1h).
Preferably, it rotates and removes preliminary low-boiling-point substance, after organic solvent, be not easy to wave using vacuum drying removing is remaining
The solvent of hair, temperature should be controlled at (80 DEG C~120 DEG C) dry (1h~4h).
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) present invention is matched by the various conditions of control reaction and the type of material, and in the excellent of aftertreatment technology
Change and select, the Vinyl MQ silicon resin that the present invention is synthesized is under the characteristic for retaining Vinyl MQ silicon resin, relatively
The ratio that its molecular weight and M/Q must be controlled is relatively stable, concentrates its molecular weight more.
(2) inventive formulation is simple, strong operability, can be effectively reduced the production cycle, can in the industry extensively
Application.
(3) Vinyl MQ silicon resin prepared by the present invention, product purity is higher, and various physical properties, chemical property are excellent.
(4) Vinyl MQ silicon resin prepared by the present invention can effectively improve the peeling force of mould release.
(5) Vinyl MQ silicon resin prepared by the present invention has outstanding hydrophobic property, can be applied to water-repellent paint.
(6) present invention can reduce bad smell, improves product, is entirely synthetically produced process and does not destroy to environment.
Detailed description of the invention
Fig. 1 is Vinyl MQ silicon resin reaction mechanism;
Fig. 2 is the H H NMR spectroscopy Local map for implementing 1 medium vinyl MQ silicone resin 1;
Fig. 3 is the H H NMR spectroscopy Local map for implementing 2 medium vinyl MQ silicone resin 2;
Fig. 4 is the H H NMR spectroscopy Local map for implementing 3 medium vinyl MQ silicone resin 3;
Fig. 5 is the H H NMR spectroscopy Local map for implementing 4 medium vinyl MQ silicone resin 4.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail, and embodiments of the present invention are not limited thereto,
Tetra functional silicon monomer described in following examples, vinyl silicane coupling agent and siloxane blocking agent are bought from Shanghai Aladdin
Biochemical technology limited liability company.
Embodiment 1
The present embodiment provides a kind of preparation methods of Vinyl MQ silicon resin.
In terms of mass fraction, a kind of Vinyl MQ silicon resin includes following raw material:
Preparation method: perfluor stirrer is first added in three-neck flask, then sequentially adds deionized water, concentrated hydrochloric acid, second
Alcohol, hexamethyldisiloxane are stirred to react 0.5h under the conditions of temperature is 60 DEG C;The ethyl orthosilicate being gradually added dropwise in stirring
With the mixed liquor of dimethoxy-methyl vinylsiloxane, time for adding is controlled in 1h;After being added dropwise, reaction temperature control exists
Continue to be stirred to react 3h under conditions of 55 DEG C;It then heats to 70 degrees Celsius and is stirred to react 0.5h;Pregnancy is added after the reaction was completed
Base disiloxane stands 6h after sufficiently vibrating, and is washed with deionized, and washing to hexamethyldisiloxane is mutually to neutrality, at 65 DEG C
Lower revolving 0.5h removes low-boiling-point substance and cosolvent;In order to increase revolving surface area, the revolving revolving speed of selection answer it is slightly larger, selection
Revolving revolving speed is 4~6 grades of EYELA N-1100 type Rotary Evaporators;Product is placed into setting in a vacuum drying oven after revolving
Temperature is 100 DEG C, and dry 4h obtains Vinyl MQ silicon resin 1.
Embodiment 2
The present embodiment provides a kind of preparation methods of Vinyl MQ silicon resin.
In terms of mass fraction, a kind of Vinyl MQ silicon resin includes following raw material:
Preparation method: perfluor stirrer is first added in three-neck flask, then sequentially adds deionized water, the concentrated sulfuric acid, second
Alcohol, hexamethyldisiloxane are stirred to react 0.5h under the conditions of temperature is 50 DEG C;Gradually be added dropwise stirring in ethyl orthosilicate and
The mixed liquor of dimethoxy-methyl vinylsiloxane, time for adding are controlled in 0.5h;After being added dropwise, reaction temperature control exists
Continue to be stirred to react 2.5h under conditions of 50 DEG C;It then heats to 70 degrees Celsius and is stirred to react 2h;Pregnancy is added after the reaction was completed
Base disiloxane stands 6h after sufficiently vibrating, and is washed with deionized, and washing hexamethyldisiloxane is mutually to neutrality, at 70 DEG C
0.5h is rotated, low-boiling-point substance and cosolvent are removed;In order to increase revolving surface area, the revolving revolving speed of selection answers slightly larger, the rotation of selection
Steaming revolving speed is 4~6 grades of EYELA N-1100 type Rotary Evaporators;Product is placed in a vacuum drying oven after revolving, setting temperature
Degree is 120 DEG C, and dry 3h obtains Vinyl MQ silicon resin 2.
Embodiment 3
The present embodiment provides a kind of preparation methods of Vinyl MQ silicon resin.
In terms of mass fraction, a kind of Vinyl MQ silicon resin includes following raw material:
Preparation method: perfluor stirrer is first added in three-neck flask, then sequentially adds deionized water, concentrated hydrochloric acid, second
Alcohol, trimethylethoxysilane are stirred to react 0.5h under the conditions of temperature is 55 DEG C;The ethyl orthosilicate in stirring is gradually added dropwise
With the mixed liquor of dimethoxy-methyl vinylsiloxane, time for adding is controlled in 1h;After being added dropwise, reaction temperature control exists
Continue to be stirred to react 3h under conditions of 65 DEG C;It then heats to 70 DEG C and is stirred to react 1h;Trimethyl ethoxy is added after the reaction was completed
Base silane stands 6h after sufficiently vibrating, and is washed with deionized, and washing trimethylethoxysilane is mutually to neutrality, in 60 DEG C of backspins
1h is steamed, low-boiling-point substance and cosolvent are removed;In order to increase revolving surface area, the revolving revolving speed of selection answers slightly larger, the revolving turn of selection
Speed is 4~6 grades of EYELA N-1100 type Rotary Evaporators;Product is placed in a vacuum drying oven after revolving, setting temperature is
105 DEG C, dry 4h obtains Vinyl MQ silicon resin 3.
Embodiment 4
The present embodiment provides a kind of preparation methods of Vinyl MQ silicon resin.
In terms of mass fraction, a kind of Vinyl MQ silicon resin includes following raw material:
Preparation method: first in three-neck flask be added perfluor stirrer, then sequentially add deionized water, the concentrated sulfuric acid,
Ethyl alcohol, trimethylethoxysilane are stirred to react 0.5h under the conditions of temperature is 50 DEG C;The positive silicic acid second in stirring is gradually added dropwise
The mixed liquor of ester and vinyltriethoxysilane, time for adding are controlled in 0.5h;After being added dropwise, reaction temperature is controlled 60
Continue to be stirred to react 4h under conditions of DEG C;It then heats to 65 DEG C and is stirred to react 1.5h;Trimethyl ethoxy is added after the reaction was completed
Base silane stands 6h after sufficiently vibrating, and is washed with deionized, and washing trimethylethoxysilane is mutually to neutrality, in 60 DEG C of backspins
1h is steamed, low-boiling-point substance and cosolvent are removed;In order to increase revolving surface area, the revolving revolving speed of selection answers slightly larger, the revolving turn of selection
Speed is 4~6 grades of EYELA N-1100 type Rotary Evaporators;Product is placed in a vacuum drying oven after revolving, setting temperature is
120 DEG C, dry 2h obtains Vinyl MQ silicon resin 4.
It is tested by above-mentioned formula, obtains following table:
Molecular weight data table 1
Mn-number-average molecular weight;Mw-weight average molecular weight;Mp-peak molecular weight;Mz-average molecular weight Mz/Mw-points
Dissipate coefficient.
From upper table 1 it is found that obtained Vinyl MQ silicon resin molecular weight distribution is more concentrated, physical property, chemical property
More excellent, indices are good;Its middle-molecular-weihydroxyethyl Mz/Mw illustrates that its coefficient of dispersion is lower, molecular weight more collects closer to 1
In;
Off-type force influences table 2
20min peeling force | 24H peeling force | 24H aging peeling force | |
Embodiment 1 | 1.03% | 18.22% | 28.43% |
Embodiment 2 | 0.92% | 16.21% | 30.26% |
Embodiment 3 | 2.12% | 15.67% | 30.38% |
Embodiment 4 | 2.42% | 14.53% | 29.17% |
From the test of 2 peeling force of table it is found that being separately added into 10% implementation into mould release (Silicone pressure sensitive glue) sample
After the MQ silicone resin that example 1 to 4 synthesizes, the peeling force of the mould release sample of the embodiment of silicone resin containing MQ 1 to 4 after 20 min is measured,
Aging peeling force after peeling force and 24H after 24H, it was concluded that the MQ silicone resin that the present invention synthesizes significant can must improve
Aging peeling force after peeling force and 24H after mould release 24H.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (8)
1. a kind of Vinyl MQ silicon resin, which is characterized in that the component including following mass fraction meter is made:
2. Vinyl MQ silicon resin according to claim 1, which is characterized in that the tetra functional silicon monomer is silicic acid
At least one of sodium, methyl orthosilicate and ethyl orthosilicate.
3. Vinyl MQ silicon resin according to claim 1, which is characterized in that the vinyl silicane coupling agent is second
Alkenyl triethoxysilane, vinyl methyl diethoxy silane, vinyl benzene radical siloxane and dimethoxy-methyl vinyl
At least one of siloxanes.
4. Vinyl MQ silicon resin according to claim 1, which is characterized in that the catalyst is hydrochloric acid, sulfuric acid, right
At least one of toluenesulfonic acid.
5. Vinyl MQ silicon resin according to claim 1, which is characterized in that the alcohol is ethyl alcohol, 1- propyl alcohol, 1- fourth
At least one of alcohol, 1- propyl alcohol, 1- amylalcohol, 2- propyl alcohol, 2- amylalcohol and cyclohexanol.
6. Vinyl MQ silicon resin according to claim 1, which is characterized in that the siloxane blocking agent is hexamethyl
In disiloxane, hexaphenyldisiloxane base, methoxytrimethylsilane, hexamethyldisilazane and trimethylethoxysilane
At least one.
7. a kind of preparation method of such as Vinyl MQ silicon resin as claimed in any one of claims 1 to 6, which is characterized in that including
Following steps:
(1) deionized water, catalyst, pure and mild siloxane blocking agent are sequentially added in the reaction vessel under the conditions of 30 DEG C~60 DEG C
It is stirred to react 0.5h~2h;
(2) on the basis of step (1), tetra functional silicon monomer and vinyl silicane coupling agent is slowly added dropwise, control temperature exists
40 DEG C~60 DEG C, time for adding is controlled in 0.5h~3h, after being added dropwise, continues to be stirred to react 2h~6h;
(3) continue to increase reaction temperature on the basis of step (2) to 60 DEG C~75 DEG C, react 0.5h~2h;
(4) solution in step (3) is extracted, is washed, revolving and vacuum drying remove solvent and low-boiling-point substance, obtain final
Product ethylene base MQ silicone resin.
8. the preparation method of Vinyl MQ silicon resin according to claim 7, feature exist:
Bath temperature is 50 DEG C~80 DEG C when revolving in the step (4), and the revolving time is 5min~1h;Vacuum drying temperature control
System is at 80 DEG C~120 DEG C, drying time 1h~4h.
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CN111393650A (en) * | 2020-04-01 | 2020-07-10 | 中科院广州化学有限公司 | Modified vinyl MQ silicon resin and preparation method and application thereof |
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CN115947943A (en) * | 2021-12-08 | 2023-04-11 | 四川晨光博达新材料有限公司 | MQ silicon resin with ultrahigh vinyl content and preparation method thereof |
CN114316270A (en) * | 2022-01-07 | 2022-04-12 | 深圳市康利邦科技有限公司 | Preparation method of modified MQ silicon resin and ketoxime-removed single-component room temperature vulcanization adhesive |
CN115678012A (en) * | 2022-11-01 | 2023-02-03 | 中科院广州化学有限公司 | Multi-terminal alkylene branched polysiloxane and preparation method and application thereof |
CN115678012B (en) * | 2022-11-01 | 2023-07-14 | 中科院广州化学有限公司 | Multi-terminal olefin-based branched polysiloxane, and preparation method and application thereof |
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