CASPER, Wyo. (AP) — A bankruptcy judge says Westmoreland Coal Co. can eliminate health care for retirees and its union contract to sell a southwestern Wyoming mine to a Virginia businessman.

Friday's ruling will likely mean retired miners who worked at the Kemmerer mine will lose their company health benefits. However, the judge delayed entering a final order until Tuesday to give the United Mine Workers of America and the Colorado-based company time to negotiate a deal.

Westmoreland, one of the nation's oldest coal operators, filed for bankruptcy in October.

The man trying to buy the mine, Tom Clarke, says the changes in employee benefits are "painful" but necessary.

The vice president of the union in Kemmerer, Mike Dalpiaz, says the contract must remain strong or miners will refuse to work.