In his judgement, Stephen Baister, chief bankruptcy registrar of the High Court, criticised the conduct of the pair in raising and then attempting to cover up false invoices at Friary Press.

"At worst Mr Crozier’s and Mr Dolan’s conduct was dishonest either from the start or at the very least, by their admission, from the time they chose to embark on the cover-up," he said. "At best, their conduct evidences incompetence to a marked degree."

In a joint statement, Dolan and Crozier stressed that "the factoring company did not lose a single penny in consequence of the alleged false invoices [as] they were adequately covered by other receivables".

The judge also slammed Dolan and Crozier’s conduct in selling off three Heidelberg presses and a Wohlenberg binding and gathering machine for a combined consideration of £910,977 without paying anything to the chargeholder, HSBC.

There was an attempt to cover up the sale of the assets by continuing to pay instalments due to HSBC, thereby disguising the fact the assets had been sold. When the companies failed, HSBC suffered a loss on the assets estimated at £545,378.

Baister said: "The way in which Mr Dolan and Mr Crozier behaved shows a lack of commercial probity, alternatively a cavalier attitude towards the company’s financing arrangements with HSBC that amounts to incompetence."

Finally, the pair were charged with receiving preferential payments from MPI and its subsidiaries totalling £227,557 at a time when "the companies concerned were insolvent" with "a significant portion paid shortly before [their] administration".

The judge accepted that these payments were "perfectly proper remuneration" but added: "PAYE and NIC were left outstanding, and Goodman Baylis was having to pay creditors using post-dated cheques.

"Those creditors were entitled to be paid just as Mr Crozier and Mr Dolan were. Unlike Mr Crozier and Mr Dolan they did not hold the purse strings and so were not paid."

Dolan told PrintWeek that he and Crozier were "extremely disappointed" with the initial court decision and that they would "await Counsel’s opinion with regard to the merits of appealing this decision".