CN115403609B - Preparation method of tris [3- (trimethoxysilyl) propyl ] isocyanurate - Google Patents

Preparation method of tris [3- (trimethoxysilyl) propyl ] isocyanurate Download PDF

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CN115403609B
CN115403609B CN202210496369.0A CN202210496369A CN115403609B CN 115403609 B CN115403609 B CN 115403609B CN 202210496369 A CN202210496369 A CN 202210496369A CN 115403609 B CN115403609 B CN 115403609B
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isocyanurate
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trimethoxysilyl
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CN115403609A (en
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张旭建
黄兵
赵凯
张�荣
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Risun Polymer International Co ltd
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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

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Abstract

The invention relates to the technical field of silane coupling agents, and discloses tris [3- (trimethoxy silane) propyl ] isocyanurate, which is synthesized by taking 3-isocyanato propyl trimethoxy silane as a precursor.

Description

Preparation method of tris [3- (trimethoxysilyl) propyl ] isocyanurate
Technical Field
The invention relates to the technical field of silane coupling agents, in particular to tris [3- (trimethoxysilyl) propyl ] isocyanurate and a preparation method thereof.
Background
The silane coupling agent contains silicon functional groups and carbon functional groups in molecules, is an excellent chemical modifier and treating agent for inorganic, organic and composite materials, and is widely applied to the fields of coating, construction, automobiles, electronics, aviation and the like. The silane hydrolysis oligomer is an oligomer which is obtained by one or more than two silane coupling agents through a certain hydrolysis condensation process and has higher viscosity and higher functionality, silane chain units 2-10 have the characteristics of high crosslinking, high adhesion, high boiling point, low volatilization, low VOC, low dosage and the like, and the silane oligomer is formed by polymerizing three isocyanate silanes, and the trimer has a six-membered ring structure, so that the structure is more stable, the requirements of the small-molecule silane coupling agent in the fields of coating, sealant, adhesive, metal powder and the like are gradually increased, the performances of the composite material such as temperature resistance, weather resistance, solvent resistance, adhesion and the like can be remarkably improved, and the silane hydrolysis oligomer is one of the key directions of the application and development of the silane coupling agent.
The silane coupling agent has wide application in the flame-retardant field, such as the document of silane coupling agent modified tea saponin intumescent flame retardant and paint application, reports that the silane coupling agent KH-550 is used for modifying the tea saponin composite intumescent flame retardant and is applied to flame-retardant paint, and the flame retardance of the paint is obviously improved; the intumescent flame retardant integrates a carbon source, a phosphorus source and a nitrogen source, such as an ammonium polyphosphate intumescent flame retardant, a starch-based intumescent flame retardant and the like, has good char formation and excellent flame retardance, and as disclosed in patent CN112063019B, a starch derivative is used as a carbon source, is compositely crosslinked with the starch derivative through a high-temperature dry-heat reaction to form a compact coating layer on the surface of the ammonium polyphosphate, and the ammonium polyphosphate is modified by utilizing the high char formation effect of the starch and the crosslinking effect of phosphate rich in phosphorus.
Disclosure of Invention
(one) solving the technical problems
Aiming at the defects of the prior art, the invention provides tris [3- (trimethoxysilyl) propyl ] isocyanurate and a preparation method thereof, and the tris [3- (trimethoxysilyl) propyl ] isocyanurate is applied to an intumescent flame retardant.
(II) technical scheme
In order to achieve the above purpose, the present invention provides the following technical solutions: tris [3- (trimethoxysilyl) propyl ] isocyanurate and application thereof.
Preferably, the tris [3- (trimethoxysilyl) propyl isocyanurate]Esters of formula C 21 H 45 N 3 O 12 Si 3 The structural formula is shown as formula (I):
preferably, the preparation method of the tris [3- (trimethoxysilyl) propyl ] isocyanurate comprises the following steps:
s1: 3-isocyanatopropyl trimethoxy silane is added into a reaction bottle, then the pH value of the reaction system is regulated, dibutyl tin dilaurate is added under the nitrogen atmosphere, and the reaction is heated and stirred.
S2: cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
Preferably, disodium hydrogen phosphate is added into the S1 to adjust the pH value of the reaction system to 7-10.
Preferably, the reaction in S1 is stirred at 125-145 ℃ for 2-8h.
Preferably, the weight ratio of the 3-isocyanatopropyl trimethoxysilane to the dibutyl tin dilaurate in the S1 is 100:0.15-0.3.
Preferably, the dimethyl dichlorosilane, the diethyl bis (2-hydroxyethyl) phosphate and the triethylamine are added into a reaction solvent in the weight ratio of 100:280-360:15-40 under ice bath, the mixture is heated to 40-75 ℃ after being uniformly stirred, the mixture is reacted for 6-18 hours, the mixture is cooled after the reaction, methanol is added for precipitation, and the mixture is filtered, distilled water and acetone are used for washing, so that the hydroxyl-terminated dimethyl silane-phosphate polymer is obtained.
S3: adding gelatinized starch into ethanol water solution, adding hydroxyl-terminated dimethyl silane-phosphate polymer and tris [3- (trimethoxysilyl) propyl ] isocyanurate, heating and stirring to react, cooling after the reaction, filtering, washing with distilled water and acetone, and obtaining the silicon-containing starch-based intumescent flame retardant.
Preferably, the reaction solvent is any one of N, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran and 1, 4-dioxane.
Preferably, the weight ratio of the gelatinized starch, the hydroxyl-terminated dimethylsilane-phosphate polymer and the tris [3- (trimethoxysilyl) propyl ] isocyanurate in S3 is 100:15-65:8-30.
Preferably, the reaction in S3 is carried out at 60-90 ℃ with stirring for 5-15h.
(III) beneficial technical effects
Compared with the prior art, the invention has the following beneficial technical effects:
the tris [3- (trimethoxysilyl) propyl ] isocyanurate takes 3-isocyanatopropyl trimethoxysilane as a precursor, and a novel silane coupling agent, namely the tris [3- (trimethoxysilyl) propyl ] isocyanurate, is synthesized, and the preparation method is simple, convenient to operate, mild in reaction and suitable for industrial production.
Dimethyl dichlorosilane and diethyl bis (2-hydroxyethyl) phosphate are used as polymerization monomers, the reaction proportion is controlled to prepare hydroxyl-terminated dimethyl silane-phosphate polymer, tris [3- (trimethoxy silane) propyl ] isocyanurate is used as a crosslinking modifier, trimethoxy silicon contained in the polymer is hydrolyzed to generate active silicon hydroxyl, and the active silicon hydroxyl can be dehydrated and condensed with the hydroxyl of starch and the hydroxyl-terminated dimethyl silane-phosphate polymer, so that the hydroxyl-terminated dimethyl silane-phosphate polymer, the hydroxyl-terminated dimethyl silane-phosphate polymer and the tris (trimethoxy silane) phosphate polymer are crosslinked to obtain the silicon-containing starch-based intumescent flame retardant.
The starch is used as a carbon source, the phosphate is used as a phosphorus source, the isocyanuric acid triazine ring is used as a nitrogen source to form an intumescent flame-retardant system, a large amount of nitrogen-containing incombustible gas and phosphoric acid derivatives are generated during combustion, a continuous and stable intumescent carbon layer can be formed, the flame retardant contains rich silicon flame-retardant elements, micro-nano silicon dioxide is generated in situ in the intumescent carbon layer during combustion, the carbon-supported layer can be played, the stability of the carbon-barrier layer is enhanced, and the effects of smoke suppression, molten drop prevention and oxygen blocking are achieved.
Drawings
FIG. 1 is a reaction scheme for preparing tris [3- (trimethoxysilyl) propyl ] isocyanurate.
FIG. 2 is a FT-IR chart of tris [3- (trimethoxysilyl) propyl ] isocyanurate.
FIG. 3 is a diagram of the reaction mechanism for preparing a siliceous starch-based intumescent flame retardant.
Detailed Description
To achieve the above object, the present invention provides the following embodiments and examples: tris [3- (trimethoxysilyl) propyl ] isocyanurate for intumescent flame retardants:
(1) Adding 3-isocyanatopropyl trimethoxy silane into a reaction bottle, then adding disodium hydrogen phosphate to adjust the pH of a reaction system to 7-10, adding dibutyl tin dilaurate under the nitrogen atmosphere, controlling the weight ratio of the 3-isocyanatopropyl trimethoxy silane to the dibutyl tin dilaurate to be 100:0.15-0.3, and stirring at 125-145 ℃ for 2-8h.
(2) Cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
(3) Adding dimethyl dichlorosilane, diethyl bis (2-hydroxyethyl) phosphate and triethylamine in a weight ratio of 100:280-360:15-40 into any one reaction solvent of N, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran and 1, 4-dioxane under ice bath, uniformly stirring, heating to 40-75 ℃, reacting for 6-18h, cooling and adding methanol for precipitation, filtering, washing with distilled water and acetone, and obtaining the hydroxyl-terminated dimethyl silane-phosphate polymer.
(4) Adding gelatinized starch into ethanol water solution, adding hydroxyl-terminated dimethyl silane-phosphate polymer and tris [3- (trimethoxysilyl) propyl ] isocyanurate, controlling the weight ratio of the gelatinized starch to the hydroxyl-terminated dimethyl silane-phosphate polymer to the tris [3- (trimethoxysilyl) propyl ] isocyanurate to be 100:15-65:8-30, heating to 60-90 ℃ and stirring for reaction for 5-15h, cooling after reaction, filtering, washing with distilled water and acetone, and obtaining the silicon-containing starch-based intumescent flame retardant.
Example 1
(1) 20g of 3-isocyanatopropyl trimethoxysilane was added to the reaction flask, then disodium hydrogen phosphate was added to adjust the pH of the reaction system to 9, 0.035g of dibutyltin dilaurate was added under nitrogen atmosphere, and the reaction was stirred at 125℃for 8 hours.
(2) Cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
(3) To 100mL of N, N-dimethylformamide was added 5g of dimethyldichlorosilane, 15g of diethyl bis (2-hydroxyethyl) phosphate and 0.75g of triethylamine under ice bath, and after stirring uniformly, the mixture was heated to 75℃and reacted for 18 hours, cooled and precipitated by adding methanol, filtered, and washed with distilled water and acetone to obtain a hydroxyl-terminated dimethylsilane-phosphate polymer.
(4) 10g of gelatinized starch is added into 150mL of ethanol water solution, then 0.26g of hydroxyl-terminated dimethyl silane-phosphate polymer and 1.5g of tris [3- (trimethoxysilyl) propyl ] isocyanurate are added, the mixture is heated to 90 ℃ and stirred for reaction for 5h, and after the reaction, the mixture is cooled, filtered, distilled water and acetone are washed, so that the silicon-containing starch-based intumescent flame retardant is obtained.
Example 2
(1) 100g of 3-isocyanatopropyl trimethoxysilane was added to the reaction flask, then disodium hydrogen phosphate was added to adjust the pH of the reaction system to 10, 0.15g of dibutyltin dilaurate was added under nitrogen atmosphere, and the reaction was stirred at 125℃for 8 hours.
(2) Cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
(3) 5g of dimethyldichlorosilane, 16g of diethyl bis (2-hydroxyethyl) phosphate and 0.75g of triethylamine are added into 150mL of tetrahydrofuran in an ice bath, the mixture is heated to 40 ℃ after being stirred uniformly, the mixture is reacted for 18 hours, cooled and added with methanol for precipitation, filtered, distilled water and acetone are used for washing, and the hydroxyl-terminated dimethylsilane-phosphate polymer is obtained.
(4) 10g of gelatinized starch is added into 300mL of ethanol water solution, then 0.65g of hydroxyl-terminated dimethyl silane-phosphate polymer and 3g of tris [3- (trimethoxysilyl) propyl ] isocyanurate are added, the mixture is heated to 65 ℃ and stirred for reaction for 15h, and after the reaction, the mixture is cooled, filtered, distilled water and acetone are washed, so that the silicon-containing starch-based intumescent flame retardant is obtained.
Example 3
(1) 20g of 3-isocyanatopropyl trimethoxysilane was added to the reaction flask, then disodium hydrogen phosphate was added to adjust the pH of the reaction system to 7, 0.042g of dibutyltin dilaurate was added under nitrogen atmosphere, and the reaction was stirred at 145℃for 3 hours.
(2) Cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
(3) To 150mL of 1, 4-dioxane was added 5g of dimethyldichlorosilane and 17.2g of diethyl bis (2-hydroxyethyl) phosphate, 1.8g of triethylamine under ice bath, and after stirring uniformly, the mixture was heated to 45℃and reacted for 12 hours, cooled and precipitated by adding methanol, filtered, and washed with distilled water and acetone to obtain a hydroxyl-terminated dimethylsilane-phosphate polymer.
(4) 10g of gelatinized starch is added into 150mL of ethanol water solution, then 0.52g of hydroxyl-terminated dimethyl silane-phosphate polymer and 3.5g of tris [3- (trimethoxysilyl) propyl ] isocyanurate are added, the mixture is heated to 80 ℃ and stirred for reaction for 8 hours, and after the reaction, the mixture is cooled, filtered, distilled water and acetone are washed, so that the silicon-containing starch-based intumescent flame retardant is obtained.
Example 4
(1) 300g of 3-isocyanatopropyl trimethoxysilane was added to the reaction flask, then disodium hydrogen phosphate was added to adjust the pH of the reaction system to 8.5, 0.5g of dibutyltin dilaurate was added under nitrogen atmosphere, and the reaction was stirred at 135℃for 3 hours.
(2) Cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
(3) To 100mL of N, N-dimethylformamide was added 5g of dimethyldichlorosilane, 15g of diethyl bis (2-hydroxyethyl) phosphate and 1.1g of triethylamine under ice bath, and after stirring uniformly, the mixture was heated to 75℃and reacted for 6 hours, cooled and precipitated by adding methanol, filtered, and washed with distilled water and acetone to obtain a hydroxyl-terminated dimethylsilane-phosphate polymer.
(4) 10g of gelatinized starch is added into 300mL of ethanol water solution, then 0.6g of hydroxyl-terminated dimethyl silane-phosphate polymer and 3g of tris [3- (trimethoxysilyl) propyl ] isocyanurate are added, the mixture is heated to 80 ℃ and stirred for reaction for 12h, and after the reaction, the mixture is cooled, filtered, distilled water and acetone are washed, so that the silicon-containing starch-based intumescent flame retardant is obtained.
Example 5
(1) 300g of 3-isocyanatopropyl trimethoxysilane was added to the reaction flask, then disodium hydrogen phosphate was added to adjust the pH of the reaction system to 8, 0.6g of dibutyltin dilaurate was added under nitrogen atmosphere, and the reaction was stirred at 140℃for 3 hours.
(2) Cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
(3) To 100mL of N, N-dimethylacetamide were added 5g of dimethyldichlorosilane, 15.8g of diethyl bis (2-hydroxyethyl) phosphate and 0.85g of triethylamine under ice bath, and after stirring uniformly, the mixture was heated to 75℃for 6 hours, cooled after the reaction and precipitated by adding methanol, filtered, and washed with distilled water and acetone to obtain a hydroxyl-terminated dimethylsilane-phosphate polymer.
(4) 10g of gelatinized starch is added into 200mL of ethanol water solution, then 0.38g of hydroxyl-terminated dimethyl silane-phosphate polymer and 2.2g of tris [3- (trimethoxysilyl) propyl ] isocyanurate are added, the mixture is heated to 70 ℃ and stirred for reaction for 12h, and after the reaction, the mixture is cooled, filtered, distilled water and acetone are washed, so that the silicon-containing starch-based intumescent flame retardant is obtained.
And placing the siliceous starch-based intumescent flame retardant in a TGA thermogravimetric analyzer, introducing nitrogen, controlling the heating rate to be 20 ℃/min, and performing thermal performance analysis at the maximum test temperature of 800 ℃.
The initial decomposition temperature of the silicon-containing starch-based intumescent flame retardant reaches 288.5-319.0 ℃, and the carbon residue reaches 56.4-73.5%.

Claims (9)

1. Use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardants, characterized in that: adding dimethyl dichlorosilane, diethyl bis (2-hydroxyethyl) phosphate and triethylamine in a weight ratio of 100:280-360:15-40 into a reaction solvent in an ice bath, uniformly stirring, heating to 40-75 ℃, reacting for 6-18h, cooling after the reaction, adding methanol for precipitation, filtering, washing with distilled water and acetone, and obtaining a hydroxyl-terminated dimethyl silane-phosphate polymer;
s3: adding gelatinized starch into ethanol water solution, adding hydroxyl-terminated dimethyl silane-phosphate polymer and tris [3- (trimethoxysilyl) propyl ] isocyanurate, heating and stirring to react, cooling after the reaction, filtering, washing with distilled water and acetone, and obtaining the silicon-containing starch-based intumescent flame retardant.
2. Use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant according to claim 1, characterized in that: the reaction solvent is any one of N, N-dimethylformamide, N-dimethylacetamide, tetrahydrofuran and 1, 4-dioxane.
3. Use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant according to claim 1, characterized in that: the weight ratio of the gelatinized starch, the hydroxyl-terminated dimethylsilane-phosphate polymer and the tris [3- (trimethoxysilyl) propyl ] isocyanurate in the S3 is 100:15-65:8-30.
4. Use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant according to claim 1, characterized in that: the reaction in the step S3 is stirred at the temperature of 60-90 ℃ for 5-15h.
5. A tris [3- (trimethoxysilyl) propyl isocyanurate as claimed in claim 1]The use of an ester in an intumescent flame retardant, characterized in that: the tris [3- (trimethoxysilyl) propyl isocyanurate]Esters of formula C 21 H 45 N 3 O 12 Si 3 The structural formula isFormula (I):
6. the use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant as claimed in claim 5, characterized in that: the preparation method of the tris [3- (trimethoxysilyl) propyl ] isocyanurate comprises the following steps:
s1: adding 3-isocyanatopropyl trimethoxy silane into a reaction bottle, then adjusting the pH value of a reaction system, adding dibutyl tin dilaurate under the nitrogen atmosphere, heating and stirring for reaction;
s2: cooling after the reaction, adding a polyacrylamide adsorbent and a diatomite filter aid, stirring uniformly, and then filtering under reduced pressure to obtain tris [3- (trimethoxysilyl) propyl ] isocyanurate.
7. The use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant as claimed in claim 5, characterized in that: and adding disodium hydrogen phosphate into the S1 to adjust the pH value of the reaction system to 7-10.
8. The use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant as claimed in claim 5, characterized in that: the reaction in the step S1 is stirred at 125-145 ℃ for 2-8h.
9. The use of tris [3- (trimethoxysilyl) propyl ] isocyanurate in intumescent flame retardant as claimed in claim 5, characterized in that: the weight ratio of the 3-isocyanatopropyl trimethoxysilane to the dibutyl tin dilaurate in the S1 is 100:0.15-0.3.
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