Ammonium Salt Catalyzed Polymerization of Benzoxazines

A kind of technology of benzoxazine and ammonium salt, applied in the field of preparing polybenzoxazine

Active Publication Date: 2021-06-04
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the resulting polybenzoxazine-epoxy hybrids still retain many of the limitations of epoxy resins, necessitating giving up many of their desirable properties (such as the toughness of epoxy resins).

Method used

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  • Ammonium Salt Catalyzed Polymerization of Benzoxazines
  • Ammonium Salt Catalyzed Polymerization of Benzoxazines
  • Ammonium Salt Catalyzed Polymerization of Benzoxazines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0166] All materials were used as received from chemical suppliers without further purification.

[0167] Table 1: Indexed Materials - Abbreviations

[0168]

[0169]

[0170] testing method

[0171] Differential Scanning Calorimetry (DSC Analysis)

[0172] Samples were prepared by melting the appropriate amount of benzoxazine and mixing the required amount of amine salt. Unless otherwise specified, mixtures were 10 molar equivalents of monofunctional benzoxazine (Ph-a) to 1 molar equivalent of amine salt. For the bifunctional BisA-a benzoxazine, the mixture is 5 molecular equivalents of monomer to 1 equivalent of amine salt, so that the total molar equivalent of benzoxazine functionality to amine salt remains at 10:1.

[0173] The thermal properties of the composition during curing were determined by placing a 4-8 mg aliquot of the composition in an aluminum pan of a Differential Scanning Calorimeter (DSC) and heating at a rate of 10 °C / min from 0°C, 20°C, or ...

preparation example 1-

[0178] Preparation example 1-synthesis of N-benzylmethylamine hydrochloride (BMAC)

[0179] In a glass vial with a magnetic stir bar, N-benzylmethylamine (1.21 g, 0.0100 mol) was dissolved in ethanol (10.0 mL). Concentrated hydrochloric acid (0.60 mL, 0.0105 mol) was added dropwise while stirring the solution vigorously. The reaction was placed in a -10°C freezer overnight. The white precipitate formed was isolated by vacuum filtration and washed with cold ethanol. Recovered mass: 0.98 g (61.8% yield). use 1 H and 13 C NMR confirmed the chemical structure.

preparation example 2-N

[0180] Preparation example 2-N-benzylmethylamine trifluoroacetate (BMATFA)

[0181] In a glass vial with a magnetic stir bar, mix N-benzylmethylamine (1.21 g, 0.0100 moles) and anhydrous trifluoroacetic acid (1.14 g, 0.0100 moles) while stirring vigorously. There was a moderate exotherm upon acid addition and the resulting clear liquid was pale orange. Recovered mass: 2.35 g (quantitative).

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Abstract

The present invention describes a process for the preparation of polybenzoxazines using an alkylammonium salt of an acid having a pKa of 9 or greater in acetonitrile as a catalyst.

Description

technical field [0001] The present invention describes a process for the preparation of polybenzoxazines using an ammonium catalyst. Background technique [0002] Benzoxazines and compositions comprising benzoxazines are known (see for example US 5,543,516 and 6,207,786 to Ishida et al; The development of a new type of electronic packaging material based on the ternary system of phenolic resin", "Polymer", 41, page 7941-7949 (2000) ("Development of New Class of Electronic Packaging Materials Based on TernarySystems of Benzoxazine, Epoxy, and Phenolic Resins", Polymer, 41, 7941-49 (2000)); and H. Kimura et al., "Novel thermosetting resins from bisphenol A-based benzoxazines and bisoxazolines", Journal of Polymer Technology Applications ", 72, pp. 1551-1558 (1999) ("New Thermosetting Resin from Bisphenol A-based Benzoxazine and Bisoxazoline", J. App. Polym Sci., 72, 1551-58 (1999)). [0003] US 7,517,925 (Dershem et al.) describes benzoxazine compounds and thermosetting resi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/02C08G73/06C08G14/06
CPCC08G14/06C08G73/0233C08G73/06C08J5/18C08J2379/04C08J2479/04C08L63/00C08L79/04
Inventor G·P·索伦森I·格罗迪舍
Owner 3M INNOVATIVE PROPERTIES CO
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