Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Main-chain benzoxazine oligomer compositions, and method for the preparation thereof

A benzoxazine and oligomer technology, applied in the field of main chain benzoxazine compositions, can solve the problems of product insolubility, low molecular weight, wide polydispersity and the like

Inactive Publication Date: 2013-05-08
MOMENTIVE SPECIALTY CHEM RES BELGIUM +1
View PDF1 Cites 24 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the synthesis of main-chain benzoxazine polymers via Mannich base polycondensation also has disadvantages, such as product insolubility due to molecular rigidity, resulting in low molecular weight and wide polydispersity.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Main-chain benzoxazine oligomer compositions, and method for the preparation thereof
  • Main-chain benzoxazine oligomer compositions, and method for the preparation thereof
  • Main-chain benzoxazine oligomer compositions, and method for the preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of a mixture of bisphenol-F benzoxazine monomers

[0055] In a 250 ml round bottom flask, bisphenol F isomer (80 mmol, 16.02 g) and aniline (160 mmol, 14.90 g) were dissolved in 75 ml of toluene. Paraformaldehyde (320 mmol, 9.60 g) was added to the solution, and then the mixture was heated at 90°C in a preheated oil bath. After the reaction, pass 1 H NMR found that the best conversion to the cyclic benzoxazine structure was achieved after about 5 hours. The solution was cooled and precipitated in hexane to obtain a yellow powder. Finally, the powder was placed in a vacuum oven at 40°C for 72 hours to dry (yield: 32 g, 81%).

Embodiment 2

[0056] Example 2: Preparation of a mixture of main chain benzoxazine oligomers

[0057] A mixture of bisphenol F isomer (100 mmol, 20.02 g), aniline (100 mmol, 9.13 g), DDM (50 mmol.9.90 g) and paraformaldehyde (400 mmol, 12 g) was added with 100 mL as a solvent Of toluene in a 250 ml round bottom flask. The milky mixture was gradually heated and kept stirring at 90°C for 5 hours. After about 15 minutes, the formation of a triaza gel was observed. After 3 hours, the insoluble white gel disappeared, forming a transparent yellow solution. Under the same conditions, the reaction mixture was stirred for another 3 hours. Then it was cooled to room temperature, and then poured into hexane to obtain a yellow powder. The powder was re-dissolved in tetrahydrofuran and reprecipitated in methanol to produce a light yellow powder (yield: 36 g, 71%).

[0058] figure 1 Show the benzoxazine monomers and main chain oligomers prepared in Examples 1 and 2 1 H-NMR spectrum. Usually, due to the ...

Embodiment 3

[0064] Example 3: Preparation of benzoxazine blend for viscosity measurement

[0065] Blends of monomers and oligomers were prepared in chloroform with monomer to oligomer ratios of 10%, 30%, and 50%, and then placed in a vacuum oven at 40°C for 72 hours to remove the solvent. by 1 H-NMR inspects dried samples to evaluate the drying of the solvent used, and only those samples showing negligible solvent content are used for viscosity testing.

[0066] Figure 4 Shows the dynamic viscosity of benzoxazine (including pure oligomers, monomers and oligomer blends). Low-viscosity benzoxazine monomers can be used as reactive diluents. In the mixture of benzoxazine monomers and oligomers, both benzoxazines can be polymerized through a ring-opening reaction to produce cross-linked products. In addition, by mixing the benzoxazine monomer and the benzoxazine oligomer, the viscosity of the mixture can be adjusted and controlled by changing the ratio of the two benzoxazines in the mixture. Fo...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
thicknessaaaaaaaaaa
glass transition temperatureaaaaaaaaaa
polydispersity indexaaaaaaaaaa
Login to View More

Abstract

Disclosed are benzoxazine compositions where oxazine rings are part of the polymer main-chain. The benzoxazine oligomers are prepared by the reaction of a bisphenol and an aldehyde, such as formaldehyde or paraformaldehyde, with one or more diamines or polyamines, and optionally with one or more monofunctional amines or monofunctional phenols. Also disclosed are benzoxazine monomers prepared from a bisphenol, an aldehyde, such as formaldehyde or paraformaldehyde, and a monofunctional amine, which benzoxazine monomers may be optionally used as reactive diluents. Further disclosed are benzoxazine monomers are prepared from a diamine, and aldehyde, such as formaldehyde or paraformaldehyde, and a monofunctional phenol, which benzoxazine monomers may also be optionally used as reactive diluents.

Description

[0001] Related application data [0002] This application claims the benefits of U.S. Provisional Application 61 / 315,709 filed on March 19, 2010, the entire content of which is incorporated herein by reference. Invention field [0003] The present invention relates to main chain benzoxazine compositions and their preparation from bisphenols, aldehydes and diamines or polyamines. Background technique [0004] Due to its excellent mechanical and thermal properties, as well as good processing capabilities for material processing and composite manufacturing, polybenzoxazine (PBZ) has attracted people's attention. The polymerization of benzoxazine can be achieved by cationic ring opening of the oxazine ring with or without the use of added initiators or catalysts. Another unique feature is that polybenzoxazine has greater molecular design flexibility than other polymers. They do not release reaction by-products during the polymerization reaction, and the synthesis or polymerization of ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C08G14/06
CPCC08L79/04C07D265/16C08G73/06C08G14/06C08G73/22C08L61/20
Inventor H·石田T·阿吉阿吉
Owner MOMENTIVE SPECIALTY CHEM RES BELGIUM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com