Shares of commercial printer Quebecor World hit a new low Friday as investors continued to bail out of the beleaguered company. 

Quebecor World stock tumbled 22 per cent in TSX trading, off 87 cents to close at $3.03. It traded as low as $2.94.

Quebecor World three-month chart

The shares have a 52-week high of $17.25 and reached $35 in early 2003.

The sell-off has been picking up speed since last week, when the printer reported a steep $315.1-million quarterly loss and announced the sale of its European operations.

On Tuesday, the company announced a refinancing that included a $250-million issue of new stock, and $500 million US of debt to shore up its balance sheet. The debt offering was made up of $400 million US in new senior unsecured notes and $100 million US of new senior unsecured convertible debentures.

The Moody's Investors Service credit rating agency downgraded $1.6 billion US of the company's existing senior unsecured notes by one notch to Caa1. That's well into junk bond territory.

Rating agencies noted some positives from the refinancing plan, but said the company still faces major difficulties. DBRS called the refinancing "an important step in addressing Quebecor World's recent liquidity constraints and should help to approve the longer-term financial health of the company."

Standard & Poor's credit analyst Lori Harris agreed that the refinancing would "improve the company's financial flexibility and liquidity position."

But the agency believes that Quebecor World's difficulties from price pressures, lower volumes and operating inefficiencies won't be ending any time soon.

"Standard & Poor's believes management will remain challenged in its efforts to turn around the business because of very difficult printing industry fundamentals," it said.

Both Standard & Poor's and DBRS have kept the negative trend outlook on the printer's long-term debt.

Quebecor World is a unit of Quebecor Inc.