CN113980476A - Anti-tarnish agent composite composition and application thereof - Google Patents
Anti-tarnish agent composite composition and application thereof Download PDFInfo
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- CN113980476A CN113980476A CN202111320176.1A CN202111320176A CN113980476A CN 113980476 A CN113980476 A CN 113980476A CN 202111320176 A CN202111320176 A CN 202111320176A CN 113980476 A CN113980476 A CN 113980476A
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5465—Silicon-containing compounds containing nitrogen containing at least one C=N bond
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Abstract
The invention discloses an anti-tarnish agent composite composition and application thereof, wherein the anti-tarnish agent composite composition comprises the following raw materials in percentage by mass: 20-30% of organic aminosilane, 15-25% of peroxide decomposing agent, 15-25% of amino silicone oil, 15-25% of hexamethyldisilazane and 5-10% of chitosan quaternary ammonium salt. The organic amino silane and the peroxide decomposer are cooperatively distributed, the system stability is jointly maintained, once the system with the optimal proportion of the organic amino silane and the peroxide decomposer is broken, the storage time of the ketoxime silane is reduced, the chitosan quaternary ammonium salt is a macromolecular polymer containing positive charges, quaternary ammonium ions in the chitosan quaternary ammonium salt can capture free radicals in the system, the product is further prevented from discoloring, the quality of the ketoxime silane is greatly improved through the cooperative proportioning effect among the organic amino silane, the peroxide decomposer, the amino silicone oil, the hexamethyldisilazane and the chitosan quaternary ammonium salt, and the storage time of the ketoxime silane is prolonged.
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and particularly relates to an anti-tarnish agent composite composition and application thereof.
Background
Ketoxime silane is often used as a vulcanizing agent and a cross-linking agent of room-temperature vulcanized silicone rubber, and also used as an accelerator for adhesion of plastics, nylon, ceramics, glass and the like with silicone rubber. Ketoximosilanes include the following compounds: methyl tributyrinoxime silane, vinyl tributyrinoxime silane, propyl tributyrinoxime silane, tetrabutoximino silane, phenyl tributyrinoxime silane, dimethyl dibutyloximino silane, methyl vinyl dibutyloximino silane, methyl tris (methyl isobutyl ketoximo) silane, vinyl tris (methyl isobutyl ketoximo) silane, tetrakis (methyl isobutyl ketoximo) silane, methyl vinyl bis (methyl isobutyl ketoximo) silane, methyl triacetoneximo silane, vinyl triacetoneximo silane, dimethyl diacetone ketoximo silane, methyl vinyl diacetone ketoximo silane, the ketoximo silanes containing a particular chemical structure of ketoximo groups that leads to the development of a dark color during storage, are specifically represented by methyl tributyrinoxime silane, propyl tributyrinoxime silane, tetrabutoximino silane, The color of compounds such as dimethyl-dibutyloximino silane is changed from 30-60-one after 6-8 months at the fastest speed in the normal-temperature storage process; the color of the compound such as vinyl tributyrinoxime silane, phenyl tributyrinoxime silane, methyl vinyl dibutyloximino silane, vinyl tri (methyl isobutyl ketoximino) silane and the like is changed from 30-60-one after 1-2 months at the fastest speed in the normal-temperature storage process; similar phenomena as above also occur with other ketoximosilanes.
The main reason for the discoloration of the ketoxime silane substances is caused by the special electron cloud structure of the ketoxime groups, and the vinyl tributyrinoxime silane and other substances not only have the electron cloud structure of the ketoxime groups, but also have the conjugated electron cloud effect of the vinyl groups, and the combined action of the two causes the vinyl tributyrinoxime silane to be relatively easy to discolor. The characteristic of easy discoloration causes the appearance quality of ketoxime silane to change along with the prolonging of time in the storage process, or causes the color, the appearance and the property of downstream products (room temperature vulcanized silicone rubber) to change in the storage process, so that the application of the ketoxime silane is limited.
At present, the application of an antioxidant in the aspect of color change prevention is reported in documents, for example, chinese patent document CN 10639394B reports a method for preventing a thiophene conductive polymerized monomer from color change, specifically, an anti-color-changing agent is added into the thiophene conductive polymerized monomer as an anti-color-changing stabilizer, wherein the added anti-color-changing agent can prevent the thiophene conductive polymerized monomer from generating polymerization and oxidation during storage and transportation to cause color change, and the anti-color-changing agent is prepared by compounding methyl hydroquinone and diphenylamine, and the weight ratio of the compounded components is 6: 4; or the anti-discoloration agent is prepared by compounding methyl hydroquinone and nitrobenzene, and the mass ratio of the compounding is 7.5: 2.5.
however, few documents have been reported on the anti-discoloration agent for ketoximosilanes, and therefore, it is necessary to develop an anti-discoloration composition which can prevent discoloration of ketoximosilanes when added thereto.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for preventing the ketoximo silane from discoloring. The problems that the conventional ketoxime silane is easy to change color, appearance and property after being stored for a long time, so that the application of the ketoxime silane is limited and the like are solved.
In order to solve the problems in the prior art, the invention is realized by the following technical scheme:
the anti-discoloration agent composite composition comprises the following raw materials in percentage by mass: 20-30% of organic aminosilane, 15-25% of peroxide decomposing agent, 15-25% of amino silicone oil, 15-25% of hexamethyldisilazane and 5-10% of chitosan quaternary ammonium salt.
Further, the anti-discoloration agent composite composition comprises the following raw materials in percentage by mass: 25% of organic amino silane, 24% of peroxide decomposing agent, 21% of amino silicone oil, 20% of hexamethyldisilazane and 10% of chitosan quaternary ammonium salt.
Further, the organic aminosilane is one of aminopropyltrimethoxysilane and aminopropyltriethoxysilane.
Further, the peroxide decomposer is one or more of phosphite ester, dimethyl dithiocarbamate and dithiophosphate.
The use of the anti-tarnish agent composite composition as described in any one of the above for preventing the discoloration of ketoximosilane, comprising the steps of:
s1, uniformly mixing organic aminosilane, a peroxide decomposer, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture;
s2, adding the mixture obtained in the step S1 into ketoxime silane, and uniformly stirring and mixing to obtain the ketoxime silane containing the anti-discoloration agent.
Further, in step S2, the addition amount of the mixture is 0.01-0.1% of the mass of the ketoximino silane.
Further, in the step S2, the temperature of adding the mixture into the ketoximino silane is 20-35 ℃.
Compared with the prior art, the invention has the following advantages:
in the invention, the organic amino silane, the peroxide decomposer, the amino silicone oil, the hexamethyldisilazane and the chitosan quaternary ammonium salt are uniformly mixed to obtain the anti-tarnish agent composite composition. Wherein, active hydrogen on amino in organic amino silane and amino silicone oil reacts with free radical, thus reducing oxidation speed of the product, and then antioxidant molecule which loses active hydrogen to form stable free radical is utilized to capture free radical to terminate oxidation reaction, so that the product is not discolored; the peroxide decomposer can convert the hydroperoxide ROOH into a product which has no free radical, no reactivity and thermal stability, and prevent the product from discoloring; the hexamethyldisilazane contains a silicon-nitrogen bond, so that free radicals in a system can be better captured, and the free radicals are prevented from reacting with a product, so that the product is discolored; the chitosan quaternary ammonium salt is a macromolecular polymer containing positive charges, has antibacterial performance on one hand, can prolong the shelf life of products, and more importantly, quaternary ammonium ions in the chitosan quaternary ammonium salt can capture free radicals in a system to further prevent the products from discoloring.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the description of the embodiments are briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
FIG. 1 is a flow chart of the method for preventing the discoloration of ketoximosilane according to the present invention.
Detailed Description
The technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments, and all other embodiments obtained by those skilled in the art without any inventive work are within the scope of the present invention.
Other conventional reagents and equipment used in the present invention are commercially available unless otherwise specified.
Example 1
The application of the anti-color-changing agent composite composition in preventing the color change of ketoximo silane comprises the following steps:
s1, uniformly mixing aminopropyltrimethoxysilane, phosphite ester, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture, wherein the mass percentage of each raw material in the mixture is as follows: 20% of aminopropyl trimethoxy silane, 25% of phosphite ester, 25% of amino silicone oil, 25% of hexamethyldisilazane and 5% of chitosan quaternary ammonium salt;
s2, adding the mixture obtained in the step S1 into ketoximo silane, wherein the addition amount of the mixture is 0.05% of the mass of the ketoximo silane, the temperature of adding the mixture into the ketoximo silane is 20-35 ℃, and stirring and mixing uniformly to obtain the ketoximo silane containing the anti-color-changing agent.
Example 2
The application of the anti-color-changing agent composite composition in preventing the color change of ketoximo silane comprises the following steps:
s1, uniformly mixing aminopropyltriethoxysilane, dimethyl dithiocarbamate, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture, wherein the mixture comprises the following raw materials in percentage by mass: 25% of aminopropyltriethoxysilane, 24% of dimethyl dithiocarbamate, 21% of amino silicone oil, 20% of hexamethyldisilazane and 10% of chitosan quaternary ammonium salt;
s2, adding the mixture obtained in the step S1 into ketoximo silane, wherein the addition amount of the mixture is 0.05% of the mass of the ketoximo silane, the temperature of adding the mixture into the ketoximo silane is 20-35 ℃, and stirring and mixing uniformly to obtain the ketoximo silane containing the anti-color-changing agent.
Example 3
The application of the anti-color-changing agent composite composition in preventing the color change of ketoximo silane comprises the following steps:
s1, uniformly mixing aminopropyltrimethoxysilane, phosphorodithioate, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture, wherein the mass percentages of the raw materials in the mixture are as follows: 30% of aminopropyl trimethoxy silane, 20% of phosphorodithioate, 20% of amino silicone oil, 20% of hexamethyldisilazane and 10% of chitosan quaternary ammonium salt;
s2, adding the mixture obtained in the step S1 into ketoximo silane, wherein the addition amount of the mixture is 0.05% of the mass of the ketoximo silane, the temperature of adding the mixture into the ketoximo silane is 20-35 ℃, and stirring and mixing uniformly to obtain the ketoximo silane containing the anti-color-changing agent.
Example 4
The application of the anti-color-changing agent composite composition in preventing the color change of ketoximo silane comprises the following steps:
s1, uniformly mixing aminopropyltriethoxysilane, phosphite ester, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture, wherein the mixture comprises the following raw materials in percentage by mass: 30% of aminopropyltriethoxysilane, 15% of phosphite ester, 25% of amino silicone oil, 25% of hexamethyldisilazane and 5% of chitosan quaternary ammonium salt;
s2, adding the mixture obtained in the step S1 into ketoximo silane, wherein the addition amount of the mixture is 0.05% of the mass of the ketoximo silane, the temperature of adding the mixture into the ketoximo silane is 20-35 ℃, and stirring and mixing uniformly to obtain the ketoximo silane containing the anti-color-changing agent.
Example 5
The application of the anti-color-changing agent composite composition in preventing the color change of ketoximo silane comprises the following steps:
s1, uniformly mixing aminopropyltrimethoxysilane, dimethyl dithiocarbamate, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture, wherein the mass percentages of the raw materials in the mixture are as follows: 30% of aminopropyl trimethoxy silane, 25% of dimethyl dithiocarbamate, 15% of amino silicone oil, 25% of hexamethyldisilazane and 5% of chitosan quaternary ammonium salt;
s2, adding the mixture obtained in the step S1 into ketoximo silane, wherein the addition amount of the mixture is 0.05% of the mass of the ketoximo silane, the temperature of adding the mixture into the ketoximo silane is 20-35 ℃, and stirring and mixing uniformly to obtain the ketoximo silane containing the anti-color-changing agent.
Example 6
The application of the anti-color-changing agent composite composition in preventing the color change of ketoximo silane comprises the following steps:
s1, uniformly mixing aminopropyltriethoxysilane, dimethyl dithiocarbamate, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture, wherein the mixture comprises the following raw materials in percentage by mass: 30% of aminopropyltriethoxysilane, 25% of dimethyl dithiocarbamate, 25% of amino silicone oil, 15% of hexamethyldisilazane and 5% of chitosan quaternary ammonium salt;
s2, adding the mixture obtained in the step S1 into ketoximo silane, wherein the addition amount of the mixture is 0.05% of the mass of the ketoximo silane, the temperature of adding the mixture into the ketoximo silane is 20-35 ℃, and stirring and mixing uniformly to obtain the ketoximo silane containing the anti-color-changing agent.
Comparative example 1
The method for preventing the ketoximo silane from discoloring is basically the same as that in example 2, except that the mass percentages of the raw materials in the mixture are different as follows: 15% of aminopropyltriethoxysilane, 34% of dimethyl dithiocarbamate, 21% of amino silicone oil, 20% of hexamethyldisilazane and 10% of chitosan quaternary ammonium salt.
Comparative example 2
The method for preventing the ketoximo silane from discoloring is basically the same as that in example 2, except that the mass percentages of the raw materials in the mixture are different as follows: 40% of aminopropyltriethoxysilane, 9% of dimethyl dithiocarbamate, 21% of amino silicone oil, 20% of hexamethyldisilazane and 10% of chitosan quaternary ammonium salt.
Comparative example 3
The method for preventing discoloration of ketoximosilane was substantially the same as in example 2, except that aminopropyltriethoxysilane was not added to the mixture.
Comparative example 4
The method for preventing discoloration of ketoximosilanes is essentially the same as in example 2, except that the dimethyl dithiocarbamate is not added to the mixture.
Comparative example 5
The method for preventing discoloration of ketoximosilanes is essentially the same as in example 2, except that no amino silicone oil is added to the mixture.
Comparative example 6
The method for preventing discoloration of ketoximosilane was substantially the same as in example 2, except that hexamethyldisilazane was not added to the mixture.
Comparative example 7
The method for preventing discoloration of ketoximosilanes is essentially the same as in example 2, except that no quaternary ammonium salt of chitosan is added to the mixture.
Example 7
The storage stability of the ketoximino silanes in examples 1-6 and comparative examples 1-6 was tested according to the method specified in the national standard "general method for measuring chromaticity of chemical reagents-GB/T605-2006"), and the ketoximino silanes without any reagent were used as blank controls, and the specific method was as follows: the ketoxime silane is placed in a constant temperature environment of 60 ℃ under the sealing condition, the time from less than 30 blacks to 60 blacks is measured, and the results are shown in the following table 1:
TABLE 1 results of the ketoximosilane storage stability test
As can be seen from the results in the table, the ketoximosilanes of examples 1-6 and comparative examples 1-6 were added to one or more of the starting materials in the mixture as compared to the blank, and as a result, the ketoximosilanes were found to increase from less than 30 blacks to more than 60 blacks significantly more than the blank, indicating that the addition of one or more of the starting materials to the mixture of the present invention to the ketoximosilane significantly extended the storage time of the ketoximosilane;
further analyzing the data in examples 1-6 and comparative examples 1-2, it can be seen that the content of aminopropyltriethoxysilane and dimethyldithiocarbamate also significantly affects the storage time of ketoximosilane, and when the content of aminopropyltriethoxysilane is low and the content of dimethyldithiocarbamate is high (comparative example 1), the content of aminopropyltriethoxysilane is high and the content of dimethyldithiocarbamate is low (comparative example 2), the storage time of ketoximosilane is somewhat reduced because the active hydrogen in aminopropyltriethoxysilane reacts with free radicals, thereby reducing the oxidation rate of the product, whereas dimethyldithiocarbamate can convert hydroperoxide ROOH into a free radical-free, non-reactive and thermally stable product, and both work synergistically to maintain the system stable once the optimum ratio system is broken, the storage time of the ketoximosilane is reduced; analysis of the data in comparative examples 3-6 shows that the lack of any component can reduce the storage time of ketoximosilane, and the results show that the quality of ketoximosilane is greatly improved and the storage time of ketoximosilane is prolonged by the synergistic proportioning effect among the organic aminosilane, the peroxide decomposer, the amino silicone oil, the hexamethyldisilazane and the chitosan quaternary ammonium salt.
Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art will understand that: any person skilled in the art can modify or easily conceive the technical solutions described in the foregoing embodiments or equivalent substitutes for some technical features within the technical scope of the present disclosure; such modifications, changes or substitutions do not depart from the spirit and scope of the embodiments of the present invention, and they should be construed as being included therein.
Claims (7)
1. The anti-discoloration agent composite composition is characterized by comprising the following raw materials in percentage by mass: 20-30% of organic aminosilane, 15-25% of peroxide decomposing agent, 15-25% of amino silicone oil, 15-25% of hexamethyldisilazane and 5-10% of chitosan quaternary ammonium salt.
2. The anti-tarnish agent composite composition according to claim 1, wherein the anti-tarnish agent composite composition comprises the following raw materials in percentage by mass: 25% of organic amino silane, 24% of peroxide decomposing agent, 21% of amino silicone oil, 20% of hexamethyldisilazane and 10% of chitosan quaternary ammonium salt.
3. The anti-tarnish agent composite composition according to claim 1 wherein said organoaminosilane is one of aminopropyltrimethoxysilane and aminopropyltriethoxysilane.
4. The anti-tarnish agent-containing composite composition according to claim 1, wherein said peroxide decomposer is one or more of phosphite, dimethyldithiocarbamate and dithiophosphate.
5. Use of the anti-tarnish agent composite composition according to any one of claims 1 to 4 for preventing discoloration of ketoximosilane, comprising the steps of:
s1, uniformly mixing organic aminosilane, a peroxide decomposer, amino silicone oil, hexamethyldisilazane and chitosan quaternary ammonium salt to obtain a mixture;
s2, adding the mixture obtained in the step S1 into ketoxime silane, and uniformly stirring and mixing to obtain the ketoxime silane containing the anti-discoloration agent.
6. The method for preventing discoloration of ketoximosilane according to claim 1, wherein in step S2, said mixture is added in an amount of 0.01 to 0.1% by mass based on the mass of said ketoximosilane.
7. The method for preventing discoloration of ketoximosilanes according to claim 1, wherein in step S2, the temperature at which said mixture is added to ketoximosilane is 20 to 35 ℃.
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