CN111393468A - Preparation method and application of water removing agent for organosilicon sealant - Google Patents

Preparation method and application of water removing agent for organosilicon sealant Download PDF

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Publication number
CN111393468A
CN111393468A CN202010290666.0A CN202010290666A CN111393468A CN 111393468 A CN111393468 A CN 111393468A CN 202010290666 A CN202010290666 A CN 202010290666A CN 111393468 A CN111393468 A CN 111393468A
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CN
China
Prior art keywords
preparation
water
organosilicon sealant
isothiocyanate
coupling agent
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Withdrawn
Application number
CN202010290666.0A
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Chinese (zh)
Inventor
曾庆铭
张迪
王凯
窦国梁
董志超
张建
王光祥
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Shandong Baolongda New Materials Co ltd
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Shandong Baolongda New Materials Co ltd
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Priority to CN202010290666.0A priority Critical patent/CN111393468A/en
Publication of CN111393468A publication Critical patent/CN111393468A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • 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
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Sealing Material Composition (AREA)

Abstract

The invention belongs to the technical field of organic silicon rubber preparation, and particularly relates to a preparation method and application of a water removing agent for an organic silicon sealant, which comprises the following steps: (1) adding aliphatic isothiocyanate and a mercaptosilane coupling agent into a reactor, and distilling under reduced pressure to remove water; (2) and (3) after reduced pressure distillation, cooling under a vacuum condition, adding a catalyst, heating for reaction, and hermetically storing a product after reaction to obtain a finished product. The aliphatic isothiocyanate and the mercaptosilane coupling agent are used as raw materials, the water removing agent for the organic silicon sealant is prepared by utilizing low-temperature reaction, the raw materials are low in price, the preparation process is simple, and the technical problems of complex process, high cost and the like are solved; the desorption product of the invention is adsorption water, which is environment-friendly, has low cost, is suitable for large-scale industrial production and has wide application prospect; the water removing agent prepared by the invention has stable structure, can prolong the storage life of the dealcoholized silicon sealant to be more than 12 months and can prolong the service performance.

Description

Preparation method and application of water removing agent for organosilicon sealant
Technical Field
The invention belongs to the technical field of organic silicon rubber preparation, and particularly relates to a preparation method and application of a water removing agent for an organic silicon sealant.
Background
The molecule main chain of the organosilicon sealant is formed by alternately and orderly arranging silicon oxygen atoms, and has excellent thermal stability, cold resistance, weather aging resistance and the like. The silicone sealant can be cured at room temperature without heating and pressurizing, is convenient to use, and is widely applied to the fields of buildings, aerospace, ships and the like. The single-component organic silicon sealant is crosslinked and cured by moisture in the atmosphere, starts to be cured from the surface of the sizing material, and finishes deep curing along with the diffusion of the moisture to the inside of the sizing material. The single-component organosilicon sealant can be classified into a deacetylated type, a dealcoholized type, a ketoxime type, an amine type and an amide type. The dealcoholized single-component organosilicon sealant only removes alcohol when being vulcanized, cannot cause corrosion of metal parts and environmental pollution, and is well received in the electronic industry and the building industry.
Dealcoholized single-component organosilicon sealant is generally prepared from a base polymer, a crosslinking agent, a catalyst, a filler, an additive and the like. The control of the moisture in the base stock in the production process is important for improving the quality of the sealant. However, the problem of the gelling phenomenon of the sealant and the reduction of the storage stability is caused by the inevitable moisture entry during the preparation process. Therefore, it is necessary to add a water scavenger to the sealant. Calcium chloride, molecular sieves and the like are commonly used inorganic water removal agents, but the strength and the bonding strength of the sealant are reduced. At present, only a few methods for preparing the water removing agent of the organosilicon sealant exist. The invention patent (CN 107903865A) discloses a water removal agent synthesized by diisononyl phthalate, polyether polyol and diisocyanate; the invention patents (CN104293231A) and (CN108624272A) disclose a method for synthesizing a water removal agent by taking an aminosilane coupling agent and diisocyanate as raw materials; the invention patents (CN102911401A) and (CN102898839A) disclose a water removal agent synthesized by alkoxy silane and alkyl alkenyl silazane. The dealcoholized organosilicon sealant hardly generates corrosion to all base materials, has good bonding performance to various base materials, is environment-friendly, and occupies larger and larger proportion in the organosilicon sealant. The research and development of the water removing agent have an important effect on improving the service performance of the dealcoholized silicon sealant. However, the currently reported method requires harsh experimental conditions, has a complex process route and high cost, and is difficult to realize industrialization.
Disclosure of Invention
The invention aims to provide a preparation method of a water removing agent for an organosilicon sealant, and solves the technical problems of harsh experimental conditions, complex process, high cost and difficult industrialization of the preparation of the water removing agent for the organosilicon sealant in the prior art.
The preparation method of the water removing agent for the organosilicon sealant comprises the following steps:
(1) adding aliphatic isothiocyanate and a mercaptosilane coupling agent into a reactor, and distilling under reduced pressure to remove water;
(2) and (3) after reduced pressure distillation, cooling under a vacuum condition, adding a catalyst, heating for reaction, and hermetically storing a product after reaction to obtain a finished product.
The aliphatic isothiocyanate is one or more of methyl isothiocyanate, ethyl isothiocyanate, tert-butyl isothiocyanate, allyl isothiocyanate and methyl isothiocyanatopropionate.
The mercapto silane coupling agent is one or more of mercaptopropyl trimethoxy silane, mercaptopropyl triethoxy silane, mercaptopropyl methyl dimethoxy silane, mercaptopropyl methyl diethoxy silane, mercaptomethyl methyl diethoxy silane and (mercapto) methyl siloxane-dimethyl siloxane copolymer.
The molar ratio of the aliphatic isothiocyanate to the mercaptosilane coupling agent is as follows: 1: (0.1-2), preferably 1: (0.3-1.8).
The process conditions of reduced pressure distillation dehydration are as follows: the temperature is 100-150 ℃, preferably 100-120 ℃, and the time is 30-150 minutes, preferably 45-130 minutes.
After distillation under reduced pressure, the mixture is cooled to 35 to 90 ℃ and preferably to 40 to 80 ℃.
The catalyst is one or more of dibutyltin dilaurate, stannous octoate, triethylamine and di-n-butylamine, and preferably dibutyltin dilaurate.
The amount of the catalyst to be used is 0.05 to 0.3%, preferably 0.1 to 0.2% of the total amount of the aliphatic isothiocyanate and the mercaptosilane coupling agent.
Adding catalyst, reacting for 60-180 min, preferably 50-90 deg.C, and reacting at 50-90 deg.C, preferably 60-80 deg.C.
The invention also aims to provide the application of the prepared water scavenger for the organosilicon sealant, which can be used as the water scavenger for preparing the dealcoholized organosilicon sealant, remove the water entering the sealant in the preparation process and prolong the storage life of the dealcoholized organosilicon sealant.
The aliphatic isothiocyanate and mercaptosilane coupling agent disclosed by the invention has active functional groups and can generate click reaction under the action of a catalyst. The sulfur element in the isothiocyanate plays a role in promoting the activation of cyanate ester, and is easy to generate hydrolysis reaction with moisture. And the existence of the mercapto silane coupling agent in the structure is helpful to improve the stability of the thiocyanate group, thereby achieving the aim of removing water and simultaneously enhancing the stability of the structure.
The invention relates to a method for preparing a high-temperature-resistant ceramic material. The aliphatic isothiocyanate is selected, so that the cost of the product can be reduced, and the aliphatic isothiocyanate has good compatibility with silicone rubber.
Compared with the prior art, the invention has the following beneficial effects.
(1) The aliphatic isothiocyanate and the mercaptosilane coupling agent are used as raw materials, the water removing agent for the organic silicon sealant is prepared by utilizing low-temperature reaction, the raw materials are low in price, the preparation process is simple, and the technical problems of complex process, high cost and the like are solved;
(2) the desorption product of the invention is adsorption water, which is environment-friendly, has low cost, is suitable for large-scale industrial production and has wide application prospect;
(3) the water removing agent prepared by the invention has stable structure, can prolong the storage life of the dealcoholized silicon sealant to be more than 12 months and can prolong the service performance.
Detailed Description
The present invention will be further described with reference to the following examples.
In the embodiment of the invention, 107 silicon rubber with the viscosity of 20000 mPas is used as a base material, methyltrimethoxysilane is used as a cross-linking agent, organotin is used as a catalyst, dimethyl silicone oil is used as a plasticizer, fumed silica is used as a reinforcing agent, and a silane coupling agent KH560 and the prepared water removal agent are added to synthesize the dealcoholized silicon rubber. But the practical application is not limited thereto.
Example 1
1mol of isothiocyanic acid ethyl ester and 0.8mol of mercaptopropyltriethoxysilane were added to a three-necked flask, and water was removed by distillation under reduced pressure at 120 ℃ for 90 minutes under stirring. And (3) cooling to 60 ℃ under a vacuum condition, dropwise adding dibutyltin dilaurate accounting for 0.1% of the total amount of the ethyl isothiocyanate and the mercaptopropyltriethoxysilane into the solution, and continuing to react for 120 minutes to obtain a water removing agent, and hermetically storing the water removing agent.
100g of 107 glue, 35g of plasticizer and 50g of reinforcing agent are fully mixed in a vacuum power mixer, heated to 110 ℃, vacuumized and dehydrated for 120 minutes to obtain the premix. And cooling to room temperature, adding 8g of cross-linking agent, 0.3g of KH560 and 1g of water removal agent, stirring for 30 minutes under a vacuum condition, adding 0.1g of catalyst, vacuumizing and stirring for 30 minutes to obtain the sealant. The surface drying time of the sealant is 18 minutes, and the storage period is 12 months.
Example 2
As described in example 1, except that methyl isothiocyanatopropionate was added. The surface drying time of the obtained sealant is 18 minutes, and the storage period is 12 months.
Example 3
Except mercaptopropylmethyldimethoxysilane was added as described in example 1. The surface drying time of the obtained sealant is 18 minutes, and the storage period is 12 months.
Example 4
The procedure is as in example 1, except that 1mol of (mercapto) methylsiloxane-dimethylsiloxane copolymer is added. The surface drying time of the obtained sealant is 20 minutes, and the storage period is 12 months.
Example 5
Except that 0.1mol of mercaptosilane coupling agent was added, as described in example 1. The surface drying time of the obtained sealant is 13 minutes, and the storage period is 12 months.
Example 6
Except that 2mol of mercaptosilane coupling agent was added, as described in example 1. The surface drying time of the obtained sealant is 15 minutes, and the storage period is 12 months.
Example 7
Except that 0.3% dibutyltin dilaurate was added dropwise as described in example 1. The surface drying time of the obtained sealant is 11 minutes, and the storage period is 12 months.
Example 8
As in example 1 except that 0.3% triethylamine was added. The surface drying time of the obtained sealant is 21 minutes, and the storage period is 12 months.
Example 9
As in example 1, except that 0.5g of water scavenger was used. The surface drying time of the obtained sealant is 20 minutes, and the storage period is 12 months.
Comparative example 1
100g of 107 glue, 35g of plasticizer and 50g of reinforcing agent are fully mixed in a vacuum power mixer, heated to 110 ℃, vacuumized and dehydrated for 120 minutes to obtain the premix. After cooling to room temperature, 8g of cross-linking agent and 1.3g of KH560 are added, the mixture is stirred for 30 minutes under the vacuum condition, then 0.1g of catalyst is added, and the mixture is stirred for 30 minutes under the vacuum condition to obtain the sealant. The surface drying time of the sealant is 26 minutes, and the storage period is 3 months.

Claims (10)

1. A preparation method of a water removing agent for organosilicon sealant is characterized by comprising the following steps: the method comprises the following steps:
(1) adding aliphatic isothiocyanate and a mercaptosilane coupling agent into a reactor, and distilling under reduced pressure to remove water;
(2) and (3) after reduced pressure distillation, cooling under a vacuum condition, adding a catalyst, heating for reaction, and hermetically storing a product after reaction to obtain a finished product.
2. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: the aliphatic isothiocyanate is one or more of methyl isothiocyanate, ethyl isothiocyanate, tert-butyl isothiocyanate, allyl isothiocyanate and methyl isothiocyanatopropionate.
3. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: the mercapto silane coupling agent is one or more of mercaptopropyl trimethoxy silane, mercaptopropyl triethoxy silane, mercaptopropyl methyl dimethoxy silane, mercaptopropyl methyl diethoxy silane, mercaptomethyl methyl diethoxy silane and (mercapto) methyl siloxane-dimethyl siloxane copolymer.
4. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: the molar ratio of the aliphatic isothiocyanate to the mercaptosilane coupling agent is as follows: 1: (0.1-2).
5. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: the process conditions of reduced pressure distillation dehydration are as follows: the temperature is 100 ℃ and 150 ℃, and the time is 30-150 minutes.
6. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: reduced pressure distillation and cooling to 35-90 ℃.
7. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: the catalyst is one or more of dibutyltin dilaurate, stannous octoate, triethylamine and di-n-butylamine.
8. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: the dosage of the catalyst is 0.05-0.3% of the total amount of the aliphatic isothiocyanate and the mercaptosilane coupling agent.
9. The preparation method of the water scavenger for the organosilicon sealant according to claim 1, wherein: adding catalyst, reacting for 60-180 min at 50-90 deg.c.
10. The use of a water scavenger for silicone sealants as claimed in any of claims 1 to 9, wherein: the water removing agent is applied to the preparation of dealcoholized organosilicon sealant.
CN202010290666.0A 2020-04-14 2020-04-14 Preparation method and application of water removing agent for organosilicon sealant Withdrawn CN111393468A (en)

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CN202010290666.0A CN111393468A (en) 2020-04-14 2020-04-14 Preparation method and application of water removing agent for organosilicon sealant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010290666.0A CN111393468A (en) 2020-04-14 2020-04-14 Preparation method and application of water removing agent for organosilicon sealant

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