Seán Quinn, his son, Seán Quinn Jr and nephew, Peter Darragh Quinn, have all been found guilty of contempt of court.
This is in relation to putting assets of the Quinns' International Property Group out of the reach of the former Anglo Irish Bank.
The bank claimed the three men had continued to take steps to implement a plan to move assets in Russia and the Ukraine out of the reach of the Irish Bank Resolution Corporation.
This was after the High Court had granted injunctions last year preventing them from doing so.
Ms Justice Elizabeth Dunne said she was not impressed with the manner in which the three men gave evidence.
She said Peter Quinn was evasive, obstructive, unco-operative and at times untruthful. She said she came to the conclusion that he would have said and done anything to aid the plan he conceived to put assets beyond the reach of Anglo.
The Judge said Seán Quinn Senior was also evasive and unco-operative. She said that on a number of occasions during the hearing, rather than answer questions put to him, he embarked on lengthy criticisms of Anglo.
She said she found it impossible to accept his evidence that he had no hand act or part in the matter after April 2011 following the appointment of a share receiver. She said his evidence to that effect was not credible.
She also she was satisfied that he gave Peter Quinn his imprimatur to implement the plan, and that he took whatever steps were required of him by signing documents as required when necessary.
She said she was satisfied beyond any doubt that he was fully supportive of it and actively involved in doing what was required to implement the plan as and when necessary.
The court also heard that the Judge found that Seán Quinn Junior was not telling the truth in giving his evidence to the court.
Ms Justice Elizabeth Dunne said Seán Quinn Senior spoke of the honourable respectable way in which the businesses in the Quinn Group were run and she wished she could say the same about the manner in which they had dealt with the adverse circumstances in which they now found themselves, having regard to the collapse of the Quinn business empire.
She said there was a dispute between Anglo and the Quinns about Anglo's ability to recover a sum of around €2.8 billion. But she said it had never been in dispute that a sum of around €455m was due to Anglo.
Instead of trying to repay the admitted debt due, the Quinn family - and in particular the three men in the contempt proceedings - had taken every step possible to make it as difficult as can be to recover any amount due.
Judge says Quinns engage in complex series of steps
The Judge said they had engaged in a complex, complicated and no doubt costly series of steps designed to put the international assets beyond the reach of Anglo in a blatant, dishonest and deceitful manner. They had consciously misled courts here and elsewhere, she added.
She said the behaviour of the respondents outlined in evidence before her, was as far removed from the concept of honour and respectability as it is possible to be.
She will hear arguments on Friday about what steps should be taken next.
The Judge said the bank had at all times made it clear that there was a punitive and a coercive element to these proceedings. She said she would have thought that the coercive element should be to the fore, given the aims of the bank and what this was all about.
She told lawyers for the Quinns that the punitive element would be influenced by the level of co operation from the Quinns in relation to any coercive order that might be made. But she said having regard to all the circumstances, it would be difficult to persuade her that there should not be a punitive element as well as a coercive.
The bank is to let the Quinns know by 8pm tomorrow night, what it intends to ask the court to do.
The possible penalties for contempt of court include imprisonment and fines.
Asked outside court what his reaction to the judgement was, Seán Quinn Senior said it was "interesting, very interesting." He said he was not dishonest.
In a statement, IBRC said it noted today's ruling by Ms Justice Dunne. The bank said that it had invested considerable time and money in seeking to protect and ultimately to recover value from these property assets which are worth about €500m and which are connected to the Quinn Family.
''It has been frustratingly obstructed from doing so in multiple jurisdictions by parties intent on putting those assets beyond the reach of the Bank and the Irish State,'' the statement added.
"Bringing this contempt motion was a valid and necessary step for IBRC to take,' the bank's chief executive Mike Aynsley said.