A kind of organosilicon benzoxazine resin prepolymer based on eugenol and its preparation method and application

A technology of silicon benzoxazine and organosilicon compound, which is applied in the field of organosilicon benzoxazine resin prepolymer and its preparation, and achieves the effects of simple operation, simple preparation and good corrosion resistance

Active Publication Date: 2019-06-18
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are no literature and patent reports on the preparation of eugenol-based organosilicon benzoxazine resin prepolymers by eugenol through hydrosilylation and polycondensation reactions in the prior art

Method used

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  • A kind of organosilicon benzoxazine resin prepolymer based on eugenol and its preparation method and application
  • A kind of organosilicon benzoxazine resin prepolymer based on eugenol and its preparation method and application
  • A kind of organosilicon benzoxazine resin prepolymer based on eugenol and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Dissolve 0.5mol eugenol, 0.2mol 1,1,3,3-tetramethyldisiloxane, and 0.01mol Karstedt catalyst in a mixed solution of 500mL dioxane and toluene at 70°C The reaction was carried out under reduced pressure for 32 hours, the mixed solvent was removed by rotary evaporation under reduced pressure, washed with water and dried to obtain bis-eugenol-1,1,3,3-tetramethyldisiloxane, the structure of which was shown in formula (1-1), Yield was 95.5%, H NMR spectrum 1 H-NMR such as figure 1 As shown, each peak on the figure is in one-to-one correspondence with the hydrogen atoms on the structure of the biseugenol-1,1,3,3-tetramethyldisiloxane compound.

[0050]

[0051] (2) Dissolve 0.1mol of the dieugenol-1,1,3,3-tetramethyldisiloxane compound prepared above in 180mL of toluene solution, add 0.11mol of ethylenediamine and 0.6mol of paraformaldehyde at 0°C After reacting for 66 hours, the mixed solvent was distilled off under reduced pressure, and dried to obtain bis-eugenol-...

Embodiment 2

[0055] (1) Dissolve 0.5mol eugenol, 0.15mol 1,1,5,5-tetramethyl-3,3-diphenyltrisiloxane, 0.02mol Speier catalyst in 500mL dioxane and toluene In the mixed solution, react at 30°C for 22 hours, remove the mixed solvent by rotary evaporation under reduced pressure, wash with water and dry to obtain biseugenol-1,1,5,5-tetramethyl-3,3-diphenyltris Siloxane, its structure is shown in formula (1-3), and productive rate is 97.1%, and hydrogen nuclear magnetic resonance spectrum 1 H-NMR such as image 3 As shown, there is a one-to-one correspondence between each peak on the figure and the hydrogen atoms on the structure of biseugenol-1,1,5,5-tetramethyl-3,3-diphenyltrisiloxane compound.

[0056]

[0057] (2) After dissolving 0.1mol of the dieugenol-1,1,5,5-tetramethyl-3,3-diphenyltrisiloxane compound prepared above in a mixed solution of 210mL dioxane and toluene Add 0.11mol ethylenediamine and 0.57mol paraformaldehyde, react at 15°C for 18 hours, distill off the mixed solvent un...

Embodiment 3

[0061] (1) Dissolve 0.5mol eugenol, 0.17mol 1,1,3,3-tetraisopropyldisiloxane, 0.01mol Speier catalyst in a mixed solution of 500mL dioxane and toluene, at 40°C After reacting for 31 hours, the mixed solvent was removed by rotary evaporation under reduced pressure, washed with water and dried to obtain bis-eugenol-1,1,3,3-tetraisopropyldisiloxane compound with a yield of 89%.

[0062] (2) Dissolve 0.1mol of the dieugenol-1,1,3,3-tetraisopropyldisiloxane compound prepared above in 250mL of dioxane solution and add 0.1mol of propylenediamine and 0.53mol of poly Formaldehyde, reacted at 30°C for 26 hours, distilled off the mixed solvent under reduced pressure, and dried to obtain bis-eugenol-1,1,3,3-tetraisopropyldisiloxane-propylenediamine silicone benzoxazine prepolymer , whose structure is shown in formula (1-5), and the yield is 98%.

[0063]

[0064] The biseugenol-1,1,3,3-tetraisopropyldisiloxane-propylenediamine silicone benzoxazine prepolymer was UV-cured with a 500W b...

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Abstract

The invention provides an organosilicon benzoxazine resin prepolymer based on eugenol. A preparation method of the prepolymer comprises the following steps: (1) eugenol and a multiple-hydrogen-terminated organosilicone monomer are subjected to an hydrosilation reaction under a catalyst effect, and therefore a eugenol organosilicon compound is obtained; and (2) the eugenol organosilicon compound, a diamine and paraformaldehyde are mixed together, a polymerization reaction is performed under heating conditions, and therefore the organosilicon benzoxazine resin prepolymer based on the eugenol is obtained. The preparation method of the prepolymer is simple, convenient in operation, good in controllability, easy to implement, and suitable for large-scale industrialized production. A polymer prepared from the organosilicon benzoxazine resin prepolymer based on the eugenol has good corrosion resistance, mechanical properties and thermal properties, and has possibility of replacing a current petroleum-based product, and the usage range is wide.

Description

technical field [0001] The invention belongs to bio-based thermosetting resins, in particular to a eugenol-based organosilicon benzoxazine resin prepolymer and its preparation method and application. Background technique [0002] Over the past century, due to the vigorous development of the petrochemical industry, the application of petrochemical products has become increasingly widespread. Various products and their derivatives obtained from petroleum have brought great convenience to people's life and production, and promoted the development of society and the progress of human civilization, but at the same time, various environmental problems cannot be underestimated. . At the same time, petroleum resources are an unsustainable and non-renewable resource. With the increasing depletion of its reserves, the cost of polymer materials derived from petroleum will inevitably increase. Recently, under the multiple pressures of protecting the environment, reducing production co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G14/06C09J161/34
CPCC08G14/06C09J161/34
Inventor 代金月刘小青马松琪腾娜沈潇斌江艳华朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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