Cardanol-aromatic diamine type benzoxazine flexibilizer as well as preparation method and purposes thereof

An aromatic diamine type, benzoxazine technology, used in the field of modification and application, synthesis of thermosetting resins, can solve the problem of short gel time, decreased mechanical strength and heat resistance of cured products, short gelation time, etc. problem, to achieve the effect of inhibiting the formation of by-products of aldolamine condensation, inhibiting the condensation reaction between methylol groups, and improving the yield and product purity

Inactive Publication Date: 2013-04-03
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this patent does not characterize the structure and content of benzoxazine in the synthetic product, so the applicability is poor
Chinese patent 201010178513.3 titled "Benzoxazine resin based on renewable resources and its composition and preparation method" reported that the benzoxazine resin was synthesized by using cardanol as regenerated phenols and decanediamine aliphatic amine, and carried out Performance test, due to the reduction of the rigid structure in the molecular structure, the mechanical strength and heat resistance of the cured product are reduced
Chinese patent 201010152874.0 titled "Manufacturing method of diamine-type benzoxazine resin with high storage stability" uses transition metal complexes as catalysts, different diamines, cardanol and formaldehyde as raw materials to synthesize good solubility and storage A benzoxazine resin solution with high stability, but the benzoxazine ring closure rate in the resin is low, it contains more oligomers and by-products, the gelation time is short, and the processing temperature range is narrow
[0005] Based on the above analysis, the monocyclic cardanol-aniline benzoxazine synthesized by cardanol with long fatty side chain can produce obvious toughening and plasticizing effects, but due to the limitation of the single ring structure, the cured product The heat resistance and mechanical strength of the synthetic bicyclic cardanol benzoxazine intermediate is an aliphatic diamine type benzoxazine or an aromatic diamine type benzoxazine resin solution containing various by-products , unable to obtain high-performance, high-purity benzoxazine monomers, there are problems of short gel time, poor processing adaptability, and low performance

Method used

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  • Cardanol-aromatic diamine type benzoxazine flexibilizer as well as preparation method and purposes thereof
  • Cardanol-aromatic diamine type benzoxazine flexibilizer as well as preparation method and purposes thereof
  • Cardanol-aromatic diamine type benzoxazine flexibilizer as well as preparation method and purposes thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Add 66.5g (0.82mol) of 37% formaldehyde aqueous solution into a reaction vessel with a stirrer, a thermometer and a reflux condenser at 40°C, start stirring, add sodium hydroxide lye, and adjust the pH value to 7~ 8. Add 120g (0.4mol) of cardanol and 96g of toluene into the reactor and stir evenly. Then add 39.6g (0.2mol) diaminodiphenylmethane (DDM) and 20g ethanol into the reactor, react at 40°C for 30min, raise the temperature to 80°C for 4h, and obtain light yellow cardanol-diaminodiphenylmethane type Crude benzoxazine product solution.

[0053] The above crude product solution of benzoxazine was washed 4 times with an excessive amount of deionized water, dried by adding anhydrous sodium sulfate for 6 hours, filtered and allowed to stand for 24 hours to precipitate, filtered and dried to obtain light yellow powdered cardanol-aromatic diamine type benzene Oxazine toughening agent product, yield 95%.

[0054] The melting point of the toughening agent powder measure...

Embodiment 2

[0056] Add 27 (0.9mol) of paraformaldehyde and 75g of water into a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, add ammonia water, adjust the pH value to 8-9, and stir at 50°C. After the paraformaldehyde was completely dissolved, 120g (0.4mol) of cardanol and 155g of dioxane were added into the reactor. Add 39.6g (0.2mol) diaminodiphenylmethane (DDM) and 15g methanol into the reactor, raise the temperature to 90°C and react for 4 hours to obtain a light yellow cardanol-diaminodiphenylmethane type benzoxazine crude product solution .

[0057] The above crude product solution of benzoxazine was washed twice with deionized water, added anhydrous sodium sulfate to dry for 12 hours, filtered and then stood still for 12 hours to precipitate, and filtered and dried to obtain light yellow powdered cardanol-aromatic diamine type benzoxazine The product of the oxazine toughening agent has a yield of 91% and a melting point of 95°C.

Embodiment 3

[0059] Add 68.6g (0.8mol) of 35% formaldehyde aqueous solution into a reaction vessel with a stirrer, a thermometer and a reflux condenser at 40°C, start stirring, add sodium hydroxide lye, and adjust the pH value to 7-8 . 120 g (0.4 mol) of cardanol and 120 g of toluene were added to the reactor. Add 40g (0.2mol) of diaminodiphenyl ether (DDE) and 20g of ethanol into the reactor, react at 40°C for 30min, raise the temperature to 80°C for 4h, and obtain light yellow cardanol-diaminodiphenyl ether type benzo Oxazine crude product solution.

[0060] The crude product solution of benzoxazine was washed twice with deionized water, dried over anhydrous sodium sulfate for 6 hours, and the solvent was removed in vacuo at 80°C to obtain a red liquid, and then a mixed solvent of 60 g of toluene and 34 g of acetone was added to obtain a reddish-brown transparent solution. After standing for 24 hours, the product of cardanol-aromatic diamine type benzoxazine toughening agent was obtain...

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Abstract

The invention discloses a cardanol-aromatic diamine type benzoxazine flexibilizer as well as a preparation method and purposes thereof. Cardanol, aromatic diamine and formaldehyde are used as raw materials, and are reacted under an alkali condition by adopting a solution synthesis method to obtain the cardanol-aromatic diamine type benzoxazine flexibilizer with high yield and high purity; in the structure, flexible aliphatic side chains of the cardanol can remarkably improve the toughness of condensates, can reduce the melt viscosity of resin systems, and can modify the forming processability; and rigid benzene ring structures of the aromatic diamine can retain high heat resistance and mechanical strength of the condensates. The benzoxazine flexibilizer is used for preparing high-performance structural materials, electric insulation materials or electronic packaging materials through lamination, mould pressing and RTM (Release to Manufacture) techniques after being mixed with epoxy resin, phenolic resin, cyanate ester resin, bismaleimide resin and other benzoxazine resin.

Description

technical field [0001] The invention relates to a cardanol-aromatic diamine type benzoxazine toughening agent, a preparation method and application thereof, and belongs to the field of synthesis, modification and application of thermosetting resins. Background technique [0002] In the synthesis of benzoxazines with flexible structures, the introduction of cardanol into benzoxazine structures has attracted extensive attention at home and abroad. Cardanol is obtained from cashew nut shell liquid (CNSL), a green biological resource, after decarboxylation treatment, and the meta-position is replaced by a long alkyl chain containing unsaturated double bonds. The long alkyl chain has excellent flexibility, and at the same time, the phenolic hydroxyl group can participate in various synthetic reactions, expanding the application field. Calo et al. synthesized a benzoxazine with cardanol and ammonia and prepared composite materials with flax. I. K. Varma et al. synthesized a benzo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/357C08K5/378C07D265/16
Inventor 顾宜张程夕冉起超朱蓉琪罗晓霞凌红
Owner SICHUAN UNIV
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