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Imide-linked maleimide and polymaleimide compounds

A technology of maleimide and bismaleimide, applied in the field of thermosetting compounds and compositions

Active Publication Date: 2006-06-07
DESIGNER MOLECULES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such thermosetting compositions are also well known to be brittle

Method used

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  • Imide-linked maleimide and polymaleimide compounds
  • Imide-linked maleimide and polymaleimide compounds
  • Imide-linked maleimide and polymaleimide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Place 250 ml of toluene in a 500 ml round bottom flask with a Teflon coated stir bar. 35 g (0.35 mol) of triethylamine was added to the flask, followed by slow addition of 35 g (0.36 mol) of anhydrous methanesulfonic acid to form a salt. The mixture was stirred for approximately 10 minutes, then 57 g (0.11 mole) of Versamine 552 (dipolymerized diamine, Cognis Corporation) was added. Pyromellitic dianhydride (10.9 g, 0.05 mole) was slowly added to the stirring mixture. A Dean-Stark cold trap and condenser were attached to the flask, and the mixture was heated to reflux for 2 hours to form the amine-terminated imide. The theoretical amount of water produced by this condensation is collected during this time. The reaction mixture was cooled to room temperature, and 12.8 g (0.13 moles) of maleic anhydride was added to the flask, followed by 5 g of anhydrous methanesulfonic acid. The mixture was refluxed for an additional 12 hours to obtain the premeasured moisture. Afte...

Embodiment 2

[0082] A salt was formed by mixing 38 g (0.38 mol) of triethylamine with 38 g (0.39 mol) of anhydrous methanesulfonic acid in 250 ml of toluene in a similar manner to that described in the previous example. Add 59g (0.11 moles) of Versamine 552 to the flask, then slowly add 16.1g (0.05 moles) of 3,3',4,4'-benzophenone tetracarboxylic dianhydride. About 2 hours of reflux are required to allow azeotropic removal of water to form the amine-terminated imide. The mixture was cooled to room temperature, then 12.5 g (0.13 mol) maleic anhydride and 5 g methanesulfonic acid were added. The mixture was refluxed for an additional 12 hours to form bismaleimide. Following the procedure described in the preceding examples, the product was worked up step by step. After complete removal of the solvent, a dark amber resin was collected (65 g, 82% yield).

Embodiment 3

[0083] The salt was formed by mixing 10 g (0.10 mol) of triethylamine with 11 g (0.11 mol) of methanesulfonic acid in 200 ml of toluene. Add 32 g (0.06 mol) Versamine 552 to the mixture, then slowly add 13.5 g (0.03 mol) 1,1,3,3-tetramethyl-1,3-bis(norbornyldicarboxylic anhydride) disiloxane . After azeotropic distillation of the water, the amine-terminated imide was formed, which required about 1 hour of reflux. The mixture was cooled, then 10 g (0.10 mol) maleic anhydride and 3 g methanesulfonic acid were added. The mixture was refluxed for an additional 18 hours to collect the required amount of water in the Dean-Stark cold trap. The stepwise work-up of the product was carried out as described in the previous examples. The final material (35 g, 73% yield) was a dark amber resin after removal of the solvent.

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Abstract

The present invention is based on the discovery that a significant improvement in the properties of thermoset maleimides can be achieved by embedding diimide-extended mono-, bis- or polymaleimide compounds. These imide-extended maleimide compounds are readily prepared. Condensation of a suitable anhydride with a suitable diamine produces an amino-terminated compound, which is then condensed with excess maleic anhydride to produce the imide-extended maleimide compound (3).

Description

[0001] Related application materials [0001] This application claims priority based on Application Serial No. 60 / 468037, filed May 5, 2003, the entire contents of which are incorporated herein by reference. field of invention [0002] The present invention relates to thermosetting adhesive compositions (thermosetting adhesive compositions), their preparation methods and applications. In particular, the present invention relates to thermosetting compounds and compositions containing imide-extended mono-, bis- and polymaleimide compounds. Background of the invention [0003] Adhesive compositions, especially conductive adhesives, are used in the manufacture and assembly of semiconductor packages and microelectronic devices for a variety of purposes. Prominent uses include bonding electronic components, such as integrated circuit chips, to lead frames or other substrates, and bonding circuit assemblies or components to printed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/28C07D207/44C07D207/452C08F2/46C08F222/40C08G73/00C08G73/12C08L77/06C08L79/08C09J179/08
CPCC07D207/452C08G73/12C08G73/125C08L79/085C09J179/085C08G73/06C07D207/448
Inventor F·G·米索里S·M·德尔舍恩
Owner DESIGNER MOLECULES
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