Seán Quinn, his son and nephew have been given three weeks to comply with orders forcing them to reverse steps they took to put property assets out of the reach of the former Anglo Irish.
Ms Justice Elizabeth Dunne made a series of orders aimed at forcing the Quinns to rectify the breaches of previous High Court injunctions.
On Tuesday, the judge found the three men guilty of contempt of court.
She found they had taken steps to put international property assets beyond the reach of the bank in a blatant, dishonest and deceitful manner.
She said she was disappointed that there had been no acknowledgement of the great wrong that had been done by the men. She said the word "flagrant" had been used to describe the contempt and added that she would not disagree with that.
The judge ordered the three men to disclose all their assets here and worldwide. She also ordered a receiver to be appointed to their assets apart from family homes and joint accounts.
They must resign from the board of directors or any executive or managerial position within the Quinn International Property Group or any company to which shares in IPG companies have been transferred.
The judge also made a number of other orders requiring the men to give instructions to stop or withdraw any legal proceedings involving the transferring of assets out of the group and reverse steps taken to do so.
The judge ordered the men to comply by July 20, when the matter will be back before the High Court again.
Ms Justice Dunne said she was anxious that this was dealt with as a matter of urgency and to make sure everything that should be done was done as quickly as it could be to rectify the breaches of high court orders she had found.
She refused to put any stay on her orders in the event of an appeal by the Quinns to the Supreme Court.
Earlier, she said she had no doubt that the first function of the court was to consider the matter of coercion and she would only consider punitive measures after seeing the extent of the cooperation from the Quinns in relation to the coercive measures.
The bank said there had been no apology from the Quinns and no acknowledgement of the scale of the contempt.
The bankrupt businessman made no comment as he left the court.