CN115785450B - Side chain silicon hydroxyl modified linear polydimethylsiloxane and preparation method thereof - Google Patents
Side chain silicon hydroxyl modified linear polydimethylsiloxane and preparation method thereof Download PDFInfo
- Publication number
- CN115785450B CN115785450B CN202310087813.8A CN202310087813A CN115785450B CN 115785450 B CN115785450 B CN 115785450B CN 202310087813 A CN202310087813 A CN 202310087813A CN 115785450 B CN115785450 B CN 115785450B
- Authority
- CN
- China
- Prior art keywords
- side chain
- linear polydimethylsiloxane
- silicon hydroxyl
- modified linear
- chain silicon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Abstract
The invention provides side chain silicon hydroxyl modified linear polydimethylsiloxane and a preparation method thereof, and belongs to the field of organosilicon preparation. The side chain silicon hydroxyl modified linear polydimethylsiloxane is prepared through the following steps: (1) Mixing linear polydimethylsiloxane with a side chain of hydrogen group, water, an organic solvent and a metal catalyst at the temperature of 0-50 ℃ and reacting for 0.1-3 hours to obtain a reaction solution; (2) And filtering the reaction solution, and removing water to obtain the side chain silicon hydroxyl modified linear polydimethylsiloxane product. The method overcomes the defect that the traditional silicon hydroxyl modified polydimethylsiloxane is easy to generate a random polymer and cannot obtain a linear polymer, and the obtained side chain silicon hydroxyl modified linear polydimethylsiloxane can replace hydroxyl silicone oil to be used as an additive of silicone rubber and has good application prospects in the aspects of daily chemicals, plant finishing, emulsifying agents and the like.
Description
Technical Field
The invention belongs to the field of organosilicon preparation, and relates to side chain silicon hydroxyl modified linear polydimethylsiloxane and a preparation method thereof.
Background
Linear polydimethylsiloxane with Si (CH) 3 ） 2 O is a main repeating unit, the side chain groups of the O are all methyl groups, and the methyl groups are inert groups, so that the application of the O is limited.The application properties of the polysiloxane such as high temperature resistance, hydrophilic property, low temperature resistance and the like can be improved by modifying the polydimethylsiloxane. The modification of the linear polydimethylsiloxane mainly introduces modification groups by a hydrosilylation mode or a silane coupling agent, which greatly limits the types of modified polysiloxanes.
The silicon hydroxyl group is the most basic reactive group in polysiloxane, and in most organosilicon reactions, the silicon hydroxyl group exists briefly in the form of an intermediate, because the silicon hydroxyl group is a group with very high reactivity, and even a trace amount of acid and alkali in a system can cause condensation of the silicon hydroxyl group to form Si-O-Si bond. If the stable silicon hydroxyl modified linear polydimethylsiloxane can be prepared, various modified groups and structure-controllable modified polydimethylsiloxane can be prepared through the reaction of silicon hydroxyl, and the preparation process of the modified polysiloxane is faster and more environment-friendly.
The traditional process for preparing the silicon hydroxyl polymer mainly comprises the steps of reacting silicon alkoxy with water under the catalysis of acid or alkali to obtain the silicon hydroxyl polymer, wherein the reaction environment is acidic or alkaline, so that when silicon hydroxyl is positioned at two ends of polydimethylsiloxane, the molecular weight and the viscosity of a system are increased; when the silicon hydroxyl groups are located in the side chains, crosslinking of the main chain occurs. Therefore, the silicon hydroxyl modified linear polydimethylsiloxane product obtained by the traditional silicon hydroxyl modification method is mainly a silicon resin product with a highly crosslinked system, and cannot obtain a linear product with a silicon hydroxyl side chain.
Chinese patent document CN115093568A provides a method for preparing organohydrocarbyl hydroxy silicone oil with high silica repeating units, adding double-end silane, water, metallic cobalt catalyst, ligand and organic solvent into a reaction bottle equipped with a stirrer under air atmosphere; and uniformly mixing the obtained materials, stirring for 10 hours at 80 ℃, and filtering after the reaction is finished to obtain the organic hydrocarbon hydroxyl silicone oil. Although this patent is capable of converting terminal Si-H bonds to Si-OH, the molecular weight of the final product is significantly increased, and significant silicon-hydroxyl condensation occurs during the reaction. There has been no report so far on linear polydimethylsiloxane having a side chain modified with a silicon hydroxyl group, and therefore, it is of great importance to provide linear polydimethylsiloxane having a side chain modified with a silicon hydroxyl group, and a method for producing the same.
Disclosure of Invention
The invention provides side chain silicon hydroxyl modified linear polydimethylsiloxane and a preparation method thereof, and aims to solve the problems that linear polydimethylsiloxane polymers with side chains of silicon hydroxyl are unstable and are easy to condense in the preparation process.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the side chain silicon hydroxyl modified linear polydimethylsiloxane has the following structural formula:
wherein R is 1 The radical being a neutral radical, R 2 The radical being a neutral radical, R 1 And R is 2 The same or different; m+n is 2 to 1500, m is 0 to 1499, and n is 2 to 1500.
Preferably, R 1 、R 2 Is a hydrocarbon group or a hydroxyl group; more preferably, R 1 、R 2 The group is vinyl, methyl or hydroxy.
Preferably, m+n is 2 to 600, m is 0 to 599, and n is 2 to 600. More preferably, m is 0 to 360 and n is 20 to 40.
Preferably, the hydroxyl content of the side chain silicon hydroxyl modified linear polydimethylsiloxane is 2-10%.
The invention also provides a mixture containing the side chain silicon hydroxyl modified linear polydimethylsiloxane, which consists of the side chain silicon hydroxyl modified linear polydimethylsiloxane and the 1, 4-dioxane, wherein the two components are in any proportion. The side chain silicon hydroxyl modified linear polydimethylsiloxane existing in the form of the mixture is more stable and is not easy to crosslink.
The preferred storage temperature of the above mixture is 0-50 ℃.
The invention also provides a preparation method of the side chain silicon hydroxyl modified linear polydimethylsiloxane, which comprises the following steps:
(1) Mixing linear polydimethylsiloxane with a side chain of hydrogen group, water, an organic solvent and a metal catalyst at the temperature of 0-50 ℃ and reacting for 0.1-3 hours to obtain a reaction solution;
(2) And filtering the reaction solution, and removing water to obtain the side chain silicon hydroxyl modified linear polydimethylsiloxane product.
The reaction equation is:
preferably, the side chain-containing silicon hydroxyl modified linear polydimethylsiloxane product is stored in 1, 4-dioxane.
Preferably, the hydrogen content (the mass fraction of hydrogen element in Si-H to the polymer I) in the linear polydimethylsiloxane with the side chain of hydrogen group in the step (1) is 0.1-1.6%. The structural formula of the linear polydimethylsiloxane with the side chain of hydrogen group is as follows:
wherein R is 3 、R 4 The radical being a neutral radical, R 3 、R 4 The same or different; m+n is 2 to 1500, m is 0 to 1499, and n is 2 to 1500.
Preferably, R 3 、R 4 The group is a hydrocarbon group, a hydroxyl group or a hydrogen group; more preferably, R 3 、R 4 The groups can be vinyl, methyl or hydrogen;
preferably, m+n is 2 to 600, m is 0 to 599, and n is 2 to 600. More preferably, m is 0 to 360 and n is 20 to 40.
Preferably, the metal catalyst in the step (1) is a palladium carbon catalyst. The mass content of palladium in the palladium-carbon catalyst is 2-30%, and more preferably 10%.
Preferably, the addition amount (calculated by metal elements) of the catalyst in the step (1) is 0.01-10% of the total system mass of the reaction, preferably 0.01-1%; more preferably 0.02 to 0.1%.
Preferably, the organic solvent in step (1) is 1, 4-dioxane. Tetrahydrofuran as a solvent is easy to cause unstable products, and the methyl tertiary butyl ether has poor compatibility with water, so that the reaction is not easy to carry out. Therefore, the application selects the 1, 4-dioxane with more industrialized basis, and the product can be stably stored for a long time.
Preferably, the amount of the organic solvent used in the step (1) is 10 to 90% by mass, preferably 20 to 80% by mass, more preferably 30 to 70% by mass of the total reaction system. The total reaction system comprises water, a solvent and linear polydimethylsiloxane with hydrogen groups on side chains.
Preferably, the temperature of the reaction in the step (1) is 5-30 ℃; the reaction time is 0.5-3 hours.
Preferably, the water added in the step (1) is 1.5-3.0 times of the theoretical demand. The theoretical demand of water is the amount of the substance of the silicon-hydrogen bond in the linear polydimethylsiloxane with the side chain of hydrogen radical.
Preferably, the hydrogen content (the mass fraction of hydrogen element in Si-H to the polymer I) in the linear polydimethylsiloxane with the side chain of hydrogen group in the step (1) is less than 0.5%, and the organic solvent in the side chain silicon hydroxyl modified linear polydimethylsiloxane product obtained in the step (2) is removed to obtain a solvent-free product. The solvent may be removed by distillation under reduced pressure.
Preferably, after the reaction is completed, the catalyst is removed by filtration. The water removal is carried out by treating the filtrate with a neutral water-absorbing salt, preferably sodium sulfate or magnesium sulfate.
The beneficial effects of the invention are that
Because Si-OH has higher reactivity, condensation is extremely easy to occur under weak acid or weak alkaline conditions, and the traditional method for preparing hydroxyl modified polysiloxane is characterized in that the prepared polysiloxane is a random polymer and cannot obtain a linear polymer due to the fact that a catalyst is acid or alkali. In the invention, linear polydimethylsiloxane with side chain as hydrogen radical is used under neutral condition to prepare the linear polydimethylsiloxane with side chain silicon hydroxyl group modified.
When the hydrogen content of the hydrogen-containing silicone oil is lower than 0.5%, the invention utilizes that the silicon hydroxyl is less distributed on polysiloxane chains and the silicon hydroxyl cannot be contacted due to obvious steric hindrance effect generated by long chains when preparing the hydroxyl modified polydimethylsiloxane product, so that condensation can not occur. When a product with higher hydroxyl content is prepared, the product is diluted by using a specific organic solvent, so that the stable existence of the silicon hydroxyl is ensured, and the side chain silicon hydroxyl modified linear polydimethylsiloxane with stable existence is obtained. In addition, the present invention uses the immobilized catalyst to react on the surface, and the steric hindrance of the catalyst itself also inhibits the condensation of the silicon hydroxyl groups. The presence of specific organic solvents will further increase the stability of the product with a lower hydroxyl content.
The silicon hydroxyl in the prepared side chain silicon hydroxyl modified linear polydimethylsiloxane can react with silicon alkoxy, and meanwhile, the product obtained by the method has a certain similarity with a hydroxyl silicone oil (the end group is hydroxyl) structure, but has more hydroxyl groups, so that the product can replace the hydroxyl silicone oil to be used as an additive of silicone rubber, and has good application prospects in daily chemicals, plant finishing, emulsifying agents and the like.
Drawings
FIG. 1 is an infrared spectrum of the product obtained in example 4;
FIG. 2 shows the product obtained in example 4 1 HNMR spectra.
Detailed Description
The present invention will be further illustrated with reference to the following examples, to which the scope of the invention is not limited. Linear polydimethylsiloxane having hydrogen groups as side chains in each example is a common commercial product available from the silicone materials Inc. of east Yue, shandong. The hydrogen content is measured by the gas flow method in chemical industry standard HG/T4804-2015. The hydroxyl group content of the obtained product is determined by coulometric titration, reference "determination of hydroxyl group content in hydroxy silicone oil", dai Wenfeng et al "organosilicon Material and use", 1995, pages 12-14. In the reaction process, the reaction process can be characterized according to Fourier infrared spectrum, and Si-H is 2200cm -1 Absorption peak at the location disappeared, patternThe bright reaction has ended completely.
Example 1
The structural formula of the polymer I (linear polydimethylsiloxane with hydrogen side chains) is as follows:
40.5g of water (1.5 times the theoretical demand), 150g of 1, 4-dioxane (51.6% of the total system mass of the reaction) and 0.5810g of palladium-carbon catalyst (the loading is 10% by weight, the addition amount of the catalyst (calculated as metal element) is 0.02% of the total system mass of the reaction) were added to the flask, stirring was started, the temperature was kept at 30℃and 100g of polymer I (hydrogen content 1.502%) was added dropwise to the flask, and the reaction was continued for 30 minutes after the completion of the dropwise addition. Through infrared detection, si-H completely reacts. Filtering by using filter paper to obtain colorless transparent liquid, gradually adding anhydrous sodium sulfate into the filtrate until the sodium sulfate is not recrystallized, filtering, and removing solids to obtain a 1, 4-dioxane solution of the side chain silicon hydroxyl modified linear polydimethylsiloxane. In the solution, the mass fraction of the silicon hydroxyl modified linear polydimethylsiloxane is 45%, and the content of hydroxyl in the silicon hydroxyl modified linear polydimethylsiloxane is measured to be 9.32%. The hydroxyl content of the product is 9.32% after being placed at 25 ℃ for 3 months, which indicates that the system has no cross-linking substance, and the product can exist stably.
Example 2
The structural formula of the polymer I is shown as follows:
100g of polymer I (hydrogen content 0.1369%), 7.39g of water (3 times the theoretical demand), 60g of 1, 4-dioxane (35.8% of the mass of the reaction system) were added to the flask, stirring was started, the temperature was kept to 10℃and then 1.67g of palladium-carbon catalyst (loading 10wt.%, catalyst addition amount was 0.1% of the mass of the reaction system in terms of metal element) was added to the flask, and the reaction was carried out at a constant temperature for 2.5 hours. Infrared detection, complete reaction of Si-H, and filtering with filter paper to obtain colorless transparent liquidA body. Removing solvent and residual water at 70 deg.C under-0.09 Mpa to obtain colorless transparent product with viscosity of 5012mm 2 And/s, the hydroxyl content of which was measured to be 2.26%. The product is preserved for 3 months at 50 ℃, no cross-linking phenomenon occurs, and the hydroxyl content is stable.
Example 3
The structural formula of the polymer I is shown as follows:
100g of polymer I (hydrogen content: 0.5%), 27.33g of water (3 times the theoretical demand), 297g of 1, 4-dioxane (70% of the mass of the reaction system) were added to the flask, stirring was turned on, the temperature was kept constant to 5 ℃, and then 2.12g of palladium-carbon catalyst (loading amount: 10wt.%, catalyst addition amount: 0.05% of the mass of the reaction system in terms of metal element) was added to the flask, and the reaction was carried out at constant temperature for 3 hours. And (3) detecting infrared, namely completely reacting Si-H, filtering by using filter paper to obtain colorless transparent liquid, gradually adding anhydrous sodium sulfate into the filtrate until the sodium sulfate is not recrystallized, filtering, and removing solids to obtain the 1, 4-dioxane solution of the side chain silicon hydroxyl modified linear polydimethylsiloxane. The hydroxyl content was measured to be 2.08%. The solid content (polysiloxane content) of the product was 26.68% and the hydroxyl number of the product was unchanged when the product was left at 25℃for 3 months. The solvent and the rest water are removed under the temperature of-0.09 Mpa and 70 ℃, the product is obviously crosslinked, the viscosity of the product is 54892mPa.s, and the hydroxyl value of the system is changed to 1.38 percent.
Example 4
The structural formula of the polymer I is shown as follows:
10.92g of water (2.0 times the theoretical demand), 1.05g of palladium-carbon catalyst (load 10 wt.%), the addition of the catalyst being 0.05% of the total mass of the reaction system in terms of metal elements, and 100g of 1, 4-dioxane (47.4% of the total mass of the reaction system) were added to the flask, stirring was started, and the temperature was kept constant to100g of Polymer I (hydrogen content 0.3033%) was added dropwise to the flask at 10℃and the reaction was continued at 10℃for 1.5 hours after the completion of the addition. The complete reaction of Si-H was detected by infrared and filtered using filter paper to give a colorless transparent liquid. Removing solvent and residual water at-0.09 Mpa and 70deg.C to obtain colorless transparent product with a product viscosity of 252mm 2 And/s, the hydroxyl content of which was determined to be 4.90%.
The product is placed at 25 ℃ for 3 months, no cross-linking substance is generated in the system, the content of the tested hydroxyl is 4.89%, and no obvious change exists, so that the product can exist stably.
From the infrared spectrum of the product obtained in example 4, it can be seen that Si-H (2200 cm -1 Near) completely disappears, at 3600-3200 cm -1 A comparatively broad absorption peak of Si-OH occurs. The product obtained from example 4 1 The chemical shift of Si-H (7.46 ppm) was disappeared in HNMR spectra, and a more remarkable chemical shift of Si-OH was observed in the vicinity of 2.28ppm, wherein Si-CH was present in the vicinity of 0.2ppm 3 Chemical shift of (c). The hydroxyl content of the product obtained in example 4 is not greatly different from the theoretical hydroxyl content, and from the detection results, si-H completely reacts to form Si-OH, and Si-OH is not condensed, so that the success of synthesizing the side chain hydroxyl modified linear polydimethylsiloxane is fully proved.
Claims (9)
1. The preparation method of the side chain silicon hydroxyl modified linear polydimethylsiloxane is characterized by comprising the following steps of:
(1) Mixing linear polydimethylsiloxane with a side chain of hydrogen group, water, an organic solvent and a metal catalyst at the temperature of 0-50 ℃ and reacting for 0.1-3 hours to obtain a reaction solution; the organic solvent is 1, 4-dioxane, and the metal catalyst is palladium-carbon catalyst;
(2) Filtering the reaction solution to remove water to obtain a side chain silicon hydroxyl modified linear polydimethylsiloxane product, wherein the side chain silicon hydroxyl modified linear polydimethylsiloxane product has the following structural formula:
wherein R is 1 、R 2 The groups are the same or different neutral groups; m+n is 2 to 1500, m is 0 to 1499, and n is 2 to 1500.
2. The method for preparing side chain silicon hydroxyl modified linear polydimethylsiloxane according to claim 1, wherein R 1 、R 2 Is a hydrocarbon group or a hydroxyl group; m+n is 2 to 600, m is 0 to 599, and n is 2 to 600.
3. The method for preparing side-chain silicon hydroxyl modified linear polydimethylsiloxane according to claim 2, wherein the hydrocarbon group is vinyl group or methyl group; m is 0 to 360, and n is 20 to 40.
4. The method for preparing side chain silicon hydroxyl modified linear polydimethylsiloxane according to claim 1, wherein the hydroxyl content of the side chain silicon hydroxyl modified linear polydimethylsiloxane is 2-10%.
5. The method for preparing side chain silicon hydroxyl modified linear polydimethylsiloxane according to claim 1, characterized in that the side chain silicon hydroxyl modified linear polydimethylsiloxane product is stored in 1, 4-dioxane.
6. The method for preparing side chain silicon hydroxyl group modified linear polydimethylsiloxane according to claim 1, characterized in that step (1) satisfies one of the following conditions:
the hydrogen content in the linear polydimethylsiloxane with the side chain being hydrogen is 0.1-1.6%;
(ii) the addition amount of the catalyst is 0.01-10% of the total mass of the reaction system calculated by metal element;
(iii) the use amount of the organic solvent is 10-90% of the total reaction system mass;
(iv) the temperature of the reaction is 5-30 ℃; the reaction time is 0.5-3 hours;
and (v) the addition amount of the water is 1.5-3.0 times of the theoretical demand amount.
7. The method for preparing side-chain silicon hydroxyl group modified linear polydimethylsiloxane according to claim 6, characterized in that step (1) satisfies one of the following conditions:
the mass content of palladium in the palladium-carbon catalyst is 2-30%;
(ii) the addition amount of the catalyst is 0.01-1% of the total mass of the reaction system calculated by metal element;
(iii) the use amount of the organic solvent is 20-80% of the total reaction system mass.
8. The method for preparing side-chain silicon hydroxyl-modified linear polydimethylsiloxane according to claim 7, characterized in that step (1) satisfies one of the following conditions:
the mass content of palladium in the palladium-carbon catalyst is 10%;
(ii) the addition amount of the catalyst is 0.02-0.1% of the total mass of the reaction system calculated by metal element;
(iii) the amount of the organic solvent is 30-70% of the total reaction system mass.
9. The method for producing side chain silicon hydroxyl modified linear polydimethylsiloxane according to claim 1, characterized in that the hydrogen content in the linear polydimethylsiloxane having a hydrogen-based side chain in step (1) is less than 0.5%, and the organic solvent in the side chain silicon hydroxyl modified linear polydimethylsiloxane product obtained in step (2) is removed to obtain a solvent-free product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310087813.8A CN115785450B (en) | 2023-02-09 | 2023-02-09 | Side chain silicon hydroxyl modified linear polydimethylsiloxane and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310087813.8A CN115785450B (en) | 2023-02-09 | 2023-02-09 | Side chain silicon hydroxyl modified linear polydimethylsiloxane and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115785450A CN115785450A (en) | 2023-03-14 |
| CN115785450B true CN115785450B (en) | 2023-05-12 |
Family
ID=85430651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310087813.8A Active CN115785450B (en) | 2023-02-09 | 2023-02-09 | Side chain silicon hydroxyl modified linear polydimethylsiloxane and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115785450B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07166063A (en) * | 1994-07-29 | 1995-06-27 | Shin Etsu Chem Co Ltd | Curable composition |
| JP3925604B2 (en) * | 2000-09-29 | 2007-06-06 | 信越化学工業株式会社 | Method for producing (meth) acryloxy group-containing organopolysiloxane |
| CN107365416B (en) * | 2017-08-30 | 2020-04-24 | 山东大学 | Method for preparing side chain modified polysiloxane |
| CN112979957A (en) * | 2021-01-28 | 2021-06-18 | 深圳市安品有机硅材料有限公司 | Method for synthesizing hydroxyl polysiloxane |
-
2023
- 2023-02-09 CN CN202310087813.8A patent/CN115785450B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN115785450A (en) | 2023-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2732357C (en) | Process for the preparation of amine-amide-functional siloxanes | |
| CN111440321B (en) | Multifunctional alkoxy-terminated polysiloxane polymer and preparation method thereof | |
| CA2499186C (en) | Fast moisture curing and uv-moisture dual curing compositions | |
| US20220056209A1 (en) | Method for preparing reactive sealant resin | |
| CN110862797A (en) | Silane-terminated polyether sealant and preparation method thereof | |
| CN114574097B (en) | Bi-component normal-temperature curing epoxy modified MQ silicon resin coating | |
| CN114989764B (en) | Silane modified polyether sealant for interior decoration and preparation method and application thereof | |
| CN109293912B (en) | Polyether with controlled silicon content and preparation method and application thereof | |
| CN110256677B (en) | Epoxy modified trifluoropropyl silicone oil and preparation method thereof | |
| CN111718489A (en) | Polysiloxane copolymer and preparation method and application thereof | |
| CN115785450B (en) | Side chain silicon hydroxyl modified linear polydimethylsiloxane and preparation method thereof | |
| EP0598263B1 (en) | Organopolysiloxane modified polyesters and method for the preparation thereof | |
| CN111454662B (en) | Room-temperature-curable organic silicon resin conformal coating and preparation method thereof | |
| CN102884109A (en) | Reactive amine-functional silicone-polyether block copolymers | |
| CN114835901B (en) | Epoxy modified vinyl silicone rubber and preparation method and application thereof | |
| CN108047451B (en) | Polycaprolactone modified polysiloxane, preparation method and application | |
| CN110684199A (en) | Organic siloxane-polyoxypropylene segmented copolymer and preparation method thereof, and prepared bi-component LED (light-emitting diode) pouring sealant and preparation method thereof | |
| CN113248715B (en) | Organic silicon polymer, preparation method thereof and organic silicon sealant | |
| CN111234233B (en) | Phenyl silicone resin and preparation method thereof | |
| CN113631638B (en) | Silyl-modified organopolysiloxane having two terminal lactate groups and method for producing same | |
| CA2337286A1 (en) | Novel poly(siloxane-acrylate) elastomers with oxycarbonylethyleneimino-containing organic groups and method of making the same | |
| US9284413B2 (en) | Process to produce stable alkoxy terminated aminofunctional silicone fluids | |
| CN111378107B (en) | Preparation method of reactive sealant resin | |
| CN113087910A (en) | Organic silicon polymer, preparation method thereof and organic silicon sealant | |
| CN115141486B (en) | Preparation method of toughened high-temperature-resistant silicone resin and toughened high-temperature-resistant silicone resin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |