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Benzoxazine intermediate containing N-allyl and composition and preparation thereof

A technology of benzoxazine and intermediates, applied in the direction of organic chemistry and the like, can solve the problems of difficult to obtain, high ring-opening temperature, difficult ring-opening polymerization, etc., and achieves improved glass transition, improved heat resistance, and improved cross-linking. The effect of density

Inactive Publication Date: 2004-02-04
BEIJING UNIV OF CHEM TECH
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  • Abstract
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Problems solved by technology

[0005] Gu Yi of Sichuan University and others reported the use of ortho-diallyl bisphenol A as the phenol O-diallyl bisphenol A-based benzoxazine was prepared from aniline and formaldehyde. Since the oxazine ring has no ortho-position hydrogen atoms, it is difficult to carry out ring-opening polymerization, which leads to a high ring-opening temperature, but no report has been made. Cured glass transition temperature (Tg)
[0011] The above-mentioned prior art about o-diallyl bisphenol A base benzoxazine, benzoxazine intermediates containing acetylene end groups, cyanonitrile functional groups, and terminal propyne groups shows that the preparation of benzoxazines containing polymerizable functional groups Benzoxazine can increase the cross-linking density of the cured product, thereby improving the thermal performance of polybenzoxazine resin; synthesizing polybenzoxazine / clay nanocomposites, making inorganic materials dispersed in the resin matrix at the nanometer scale can also be Improve the thermal properties of polybenzoxazine resins; but the raw materials such as m-ethynyl aniline, p-formonitrile aniline, p-propynyloxy aniline used in these prior art are expensive and difficult to obtain, which greatly limits their application

Method used

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  • Benzoxazine intermediate containing N-allyl and composition and preparation thereof

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Embodiment 2

[0045] Then it is cured. The curing temperature and time are: 2 hours at 110°C, 2 hours at 180°C, 2 hours at 200°C, 2 hours at 220°C and 2 hours at 240°C to obtain the curing After thermal analysis, its glass transition temperature (Tg) reached 284°C (determined by DMA method). Example 2 Preparation of 2,2-bis(3,4-dihydro-3-allyl-1,3-benzoxazine) propane, that is, bisphenol A type N-allylbenzoxazine, by melting method (The structural formula is as follows, referred to as ABPA)

[0046] Add (15ml, 0.2mol) allylamine to bisphenol A (22.83g, 0.1mol) at room temperature, stir at low temperature (2℃) until the system is a transparent and homogeneous mixture; add in batches (12.00g, 0.4mol) ) Paraformaldehyde, continue to stir for 10 min (according to the molar ratio of phenolic hydroxyl, amine and aldehyde functional groups, it is 1:1:2). The temperature was gradually increased to reflux, and the reaction was stopped after 2.5 hours of reaction. Cool to obtain a milky white solid; the...

Embodiment 3

Embodiment 4 Synthetic preparation 2，2-(3，4- 2 -3--1，3-)AN-(，ABPA) approach and Embodiment 2，A、、1∶2.4∶4.8(、、1∶1.2∶2.4)，2，2-(3，4- 2 -3--1，3-)2，2-(3，4- 2 -3--1，3-)，98％；H-NMR，98％。 Embodiment 5

[0048]The method is the same as in Example 2, except that the molar ratio of bisphenol, allylamine A, and paraformaldehyde is 1:2.2:4.4 (according to the molar ratio of phenolic hydroxyl group, amine group, and aldehyde group, it is 1:1.1: 2.2), 2,2-bis(3,4-dihydro-3-allyl-1,3-benzoxazine) propane is prepared as light yellow crystals, namely 2,2-bis(3,4-di Hydroxy-3-allyl-1,3-benzoxazine) propane, the yield is 99%; through H-NMR measurement, the ring formation rate is 100%. Example 4 Preparation of 2,2-bis(3,4-dihydro-3-allyl-1,3-benzoxazine)propane, namely bisphenol A type N-allylbenzoxine, by a melt synthesis method The method of oxazine (see below for structural formula, ABPA for short) is the same as in Example 2, except that the molar ratio of bisphenol A, allylamine, and paraformaldehyde is 1:2.4:4.8 (according to phenolic hydroxyl group, amino group, and aldehyde group). The molar ratio is 1:1.2:2.4), and 2,2-bis(3,4-dihydro-3-allyl-1,3-benzoxazine) propane is obtained as l...

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Abstract

A benzoxazine intermediate containing N-allyl is prepared from allyltriamine, phenols and aldehydes. Its composition is prepared from said benzoxazine intermediate, thermosetting resin and / or filler through mixing or in-situ polymerizing. They have excellent high temp resistance, chemical performance, flame-retarding behaviour and machinability.

Description

Technical field [0001] The present invention relates to a kind of N-allyl-containing benzoxazine intermediates and compositions and preparation methods thereof. More specifically, the present invention relates to N-containing N-containing primary amines, phenols and aldehydes. -Allyl benzoxazine intermediates, and compositions prepared by mixing or in-situ polymerization using such benzoxazine intermediates and other thermosetting resins and / or fillers. Background technique [0002] Polybenzoxazine resin is a benzoxazine intermediate obtained through the ring-forming reaction of primary amines, phenols and aldehydes on the basis of the traditional method of preparing phenolic resins. Under heating (a catalyst can also be used) , Benzoxazine ring-opening polymerization produces ring-opening phenolic resin, which is a new type of thermosetting resin with nitrogen-containing and similar phenolic resin network structure. [0003] H. Schreiber reported the ring-opening polymerization ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/36C08K5/357C08L61/06C08L63/00C08L67/06
Inventor 余鼎声徐日炜丁雪佳张炳伟
Owner BEIJING UNIV OF CHEM TECH
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