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

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
  • Epoxy-capped polythioethers
  • 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): C07D303/22C08G59/02C08G59/20C08G59/30C08L63/00
CPCC07D303/22C08L63/00C08G59/302C08G59/02C08G59/20C08G59/30
Inventor SAWANT, SURESHRAO, CHANDRA BHUSHAN
Owner PRC DE SOTO INT INC
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