Seán Quinn leaves the Four Courts in Dublin in March 2012. (Pic: Julien Behal/PA)

Bankrupt tycoon Seán Quinn, his son and nephew could face jail after being found in contempt of court for putting part of an international property portfolio beyond the reach of the former Anglo-Irish Bank.

A court ruled the former billionaire, son Seán Jnr and nephew Peter Darragh consciously defied and misled the courts as they shifted family assets as far afield as Ukraine, Russia and Belize.

The lawsuit was brought by the State-owned bank over claims the three breached a High Court order, made in Dublin in April last year, and moved businesses into shelf companies to avoid repaying debts.

The Quinns owe Anglo €2.8bn.

Mrs Justice Elizabeth Dunne said instead of trying to pay an undisputed sum of €455m, the Quinn family took every step possible to make it life difficult for Anglo.

“They have engaged in a complex, complicated and, no doubt, costly series of steps designed to put the assets of the IPG (international property group) beyond the reach of Anglo, in a blatant, dishonest and deceitful manner,” she said in a damning judgment.

“They have consciously misled courts here and elsewhere.

“They have sought to deprive Anglo of the assets which would go some way to discharging an admitted indebtedness.

“The behaviour of the respondents outlined in evidence before me is as far as removed from the concept of honour and respectability as it is possible to be.”

Outside the court, Mr Quinn – who was once Ireland’s richest man – said the judgment was “interesting, very interesting”, and added “I am not dishonest” before he left in a waiting car.

The contempt lawsuit was the latest court battle the Fermanagh-born businessman has lost after he secured bankruptcy in Northern Ireland only for it to be overturned and a Dublin court then to declare him bankrupt.

It is also one of a series of cases across several jurisdictions as the zombie bank, rebranded last year to the Irish Bank Resolution Corporation, tries to recover a €500m international property portfolio to cover debts run up by Mr Quinn in secret and ill-fated share deals in Anglo.

The judge warned that potential punishment for contempt would include a punitive sanction – which could be jail.

She will decide on Friday what sanctions to impose on the three, whose evidence she described as uncredible, unbelievable and evasive.

“It would be very difficult to persuade me there should not be a punitive element,” she said as she told the Quinns’ layers that aspect of the sanction would be influenced by the level of co-operation they give in relation to any coercive order made.

In fierce criticism of the Quinns, the judge said the bank had faced considerable obstacles and was opposed at every step as it chased assets.

She said she was not impressed with the manner in which the three gave evidence, describing Peter Darragh Quinn as evasive, less than forthright, obstructive, unco-operative and, at times, untruthful.

She said evidence about his overseas trips, including to Kiev and Dubai, was not credible.

“Seán Quinn senior was also a witness who was evasive and unco-operative,” she told the packed courtroom.

“On a number of occasions during the hearing, rather than answer questions put to him, he embarked on lengthy criticisms of Anglo.

“First of all, it is clear that I do not accept his evidence that steps were taken to put assets beyond the reach of Anglo by the signing of the various assignments and other documents referred to in April 2011.

“Secondly, I find it impossible to accept the evidence of Sean Quinn senior to the effect that he had no hand, act or part in the matter after April 2011 following the appointment of the share receiver. His evidence to that effect is not credible in my view.”

Mrs Justice Dunne said she also came to the conclusion Sean junior was not telling the truth, declaring his evidence over a trip to Kiev last August as “simply unbelievable”.

She said he was there to oversee a US$500,000 transfer from Quinn Properties Ukrainian (QPU) to Ms Larisa Yanez Puga, general director of Univermag, a Quinn-owned company in the eastern European state.

The bank’s pursuit of assets held by the Quinns has led to a paper trail and court cases in Ireland, Northern Ireland, Russia, the Ukraine, Cyprus, Sweden and Belize.

The contempt case was told that, in the Cypriot court battle, misleading affidavits were sworn by the Quinn family.

The judge said that, during his evidence, Mr Quinn senior spoke of the Quinn Group and its importance as an employer of 7,000 people.

“One can appreciate the ability that led to the creation of such a business empire,” she added.

“Seán Quinn senior also spoke of the honourable, respectable way in which the businesses comprised in the Quinn Group were run.

“I wish I could say the same about the manner in which the respondents have dealt with the adverse circumstances in which they now find themselves having regard to the collapse of the Quinn business empire.”

Mike Aynsley, Irish Bank Resolution Corporation chief executive, said: “The proven planned, covert and illicit actions taken by the Quinns and connected parties have resulted in millions of euros being lost or put at risk.

“IBRC will continue to seek to remedy this and recover as much of the remaining assets as possible on behalf of the Irish taxpayer.”