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Epoxy-capped polythioethers

a polythioether and epoxy-capped technology, applied in the field of epoxy-capped polythioethers and curable compositions, can solve the problem of extremely toxic epichlorohydrin

Inactive Publication Date: 2005-01-13
PRC DE SOTO INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes a new type of epoxy compound that can be used in aviation and aerospace applications. These compounds have a unique structure that makes them more suitable for use in these fields. The text also describes methods for making these compounds and curable compositions that can be used for various applications. Overall, this invention provides a new and improved epoxy compound that can be used in a variety of settings.

Problems solved by technology

Epichlorohydrin is extremely toxic and the synthesis of epoxy-terminated polysulfides using epichlorohydrin generates corrosive hydrolysable chlorine (“HYC”) as an undesirable byproduct.
Further, the compounds formed using epichlorohydrin incorporate un-reacted epichlorohydrin that must be removed by thorough washing.

Method used

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  • Epoxy-capped polythioethers

Examples

Experimental program
Comparison scheme
Effect test

example 1

253.4 g (1.39 mole) of dimercaptodioxaoctane (DMDO) was added to a 1 liter 4-neck flask under a nitrogen atmosphere. While stirring, the contents of the flask was heated to 50° C., and 146.6 g (0.93 mole) of diethylene glycol divinyl ether (DEG-DVE) was added over 1 hr. The temperature of the reaction mixture was increased to 70° C. and 0.05 g of free-radical initiator Vazo®67 (2,2′-azobis(2-methylbutyronitrile), Du Pont) was added. The temperature of the reaction mixture was maintained at 70° C. for an additional hour. Completion of the reaction of DEG-DVE with DMDO was indicated by a mercaptan equivalent value of 420. Allyl glycidyl ether (AGE) (110.87 g, 0.97 mole, 2% stoichiometric excess) was added at 70° C. over 1 hr and the reaction mixture was heated at 70° C. for an additional hour. Ten portions of Vazo®67 (0.165 g each) were then added at 3 hr intervals at 70° C. Following addition of Vazo®67 the reaction mixture was heated at 70° C. for 5 hr. The reaction mixture was the...

example 2

62.17 g (moles) of DMDO was added to a 250 ml 3-neck flask under a nitrogen atmosphere. While stirring, DMDO was heated to 60° C. and 44.88 g (mole) of DEG-DVE was added to the reaction mixture over a period of 50 minutes while the temperature of the reaction was maintained at 60° C.-70° C. The reaction mixture was heated at 70° C. for an additional 4 hr. Two portions of Vazo®67 (0.036 g each) were added to the reaction mixture at 1.5 hr intervals and heated at 70° C. for 1.5 hr. The mercaptan equivalent value of the reaction mixture was 890. An additional portion of Vazo®67 (0.036 g) was added and the reaction mixture heated for another 1.5 hr. A mercaptan equivalent value of 893 indicated completion of the reaction of DEG-DVE with DMDO. AGE (13.21 g, 0.116 mole, 2% stoichiometric excess) was added at 70° in one portion and the reaction mixture was heated for 2 hr. Eight portions of Vazo®67 (0.035 g each) were added at 3 hr intervals at 70° C. and heating was continued for another...

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Abstract

Epoxy-capped polythioethers and curable compositions of epoxy-capped polythioethers are disclosed.

Description

FIELD OF THE INVENTION This invention generally relates to epoxy-capped polythioethers and curable compositions of epoxy-capped polythioethers. BACKGROUND OF INVENTION It is desirable that sealants, coatings, and adhesives used in aviation and aerospace applications exhibit flexibility, fuel resistance, and high-temperature resistance. In general, these properties may be accomplished by incorporating polythioether linkages into the backbone of polymer resins. Flexible, fuel resistant epoxy-terminated polysulfides have been developed which exhibit good fuel resistance. These compounds are typically formed using epichlorohydrin as a reactant. Epichlorohydrin is extremely toxic and the synthesis of epoxy-terminated polysulfides using epichlorohydrin generates corrosive hydrolysable chlorine (“HYC”) as an undesirable byproduct. Further, the compounds formed using epichlorohydrin incorporate un-reacted epichlorohydrin that must be removed by thorough washing. Such epoxy-terminated pol...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D303/22C08G59/02C08G59/20C08G59/30C08G75/04C08G75/045C08L63/00
CPCC07D303/22C08L63/00C08G59/302C08G59/02C08G59/20C08G59/30
Inventor SAWANT, SURESHRAO, CHANDRA BHUSHAN
Owner PRC DE SOTO INT INC
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