After a 2018 fire at his Hamptons estate, Ronald O. Perelman argued that among the paintings damaged by the blaze were five particularly valuable works from his collection, including a Cy Twombly that he later said had “lost its oomph.”

Insurers of the property balked at paying for those works, saying they had survived unharmed. Holding companies affiliated with Mr. Perelman sued for hundreds of millions of dollars.

On Friday, a judge in New York who had presided over a bench trial rejected Mr. Perelman’s view, saying he saw nothing to prevent “the artworks from being enjoyed as they were before.”

“I find that there was no visible damage to the five paintings,” Justice Joel M. Cohen of State Supreme Court in Manhattan said, adding: “Nothing traceable to the fire.”

While finding for the insurers, Justice Cohen added that they had not proven their contention that Mr. Perelman had intentionally misled them.

A lawyers for the holding companies had no comment on whether they might appeal.

Justice Cohen’s decision resolved, at least for the moment, a lengthy battle that began after the fire in an attic at Mr. Perelman’s 72-acre estate known as The Creeks. The litigation has drawn attention, in part because it explored questions of how to define and calculate damage, including some that may not be visible to the naked eye. It also included allegations by insurers that the case was “a portrait of a contrived claim” generated by a man in dire need of money.

There is no dispute that several works at the estate were damaged in the fire, some severely. Holding company lawyers contend that even if the five at issue — two by Andy Warhol, two by Ed Ruscha and the Twombly — were not scorched by flames or soaked by hoses, they were harmed when “dangerous levels of humidity, soot and smoke” penetrated protective frames that encased them.

In a 2021 examination under oath, Mr. Perelman sought to describe the impact on the Twombly, an untitled paint and wax crayon work from 1971 with five rows of oval-shaped lines filling a canvas. It had hung above a fireplace in the dining room of the main residence.

“It didn’t have its spark,” he said. “It didn’t have its distinctive definition in the lines, in the swirls. It just lost — it just lost its oomph.”

Lawyers for the insurers rejected those arguments. They asserted instead that Mr. Perelman, a billionaire businessman who gained control of the cosmetics giant Revlon in a hostile takeover in 1985, was pursuing a frivolous claim. In court papers, they stated flatly that “this case has always been about cashing in, not actual damage.”

Mr. Perelman is known for both his generosity and for his court battles. He has donated $75 million to an arts complex at the former World Trade Center site and briefly served as chairman of Carnegie Hall, a position from which he stepped down after butting heads with the artistic director. His legal opponents have included ex-wives, the mega-dealer Larry Gagosian and Morgan Stanley, among others.

The insurance case was as complex as any of them. Before Justice Cohen’s decision, the docket had included nearly 2,000 entries and the litigation featured testimony from competing experts about thermodynamics and the possibility of molecular-level changes to paint.

Each side accused the other of bad faith. A plaintiff’s lawyer said that insurers had acknowledged loss of or damage to 30 artworks that had been in the Creeks the night of the fire — including 11 that had been on the ground floor of the home, just like the five at issue in the lawsuit. The insurers had not wanted to admit those works had been damaged as well, the lawyer suggested, because they were insured for the highest amounts: a total of $410 million.

“Until policyholders sought payment on these five artworks, the insurers had agreed that every artwork on the first floor for which policyholders sought coverage was at least partly damaged,” the lawyer, C. Bryan Wilson, told Justice Cohen during an opening statement this summer. “We didn’t change our tune. The insurers did.”

A lawyer representing the Federal Insurance Company replied that the appraised market value for the five paintings was only about $100 million and suggested that Mr. Perelman sought payment for them because he was facing a cash crunch brought on by a decline in the value of Revlon stock. As a result of that, the lawyer said, Mr. Perelman had sold some 70 other works to raise nearly $1 billion to satisfy loans.

That lawyer, Jonathan Rosenberg, accused Mr. Perelman of flip-flopping on whether or not the Twombly had been harmed, first offering it for sale after an expert concluded it had emerged from the fire unscathed, then making an insurance claim when it did not sell. According to Mr. Rosenberg, Mr. Perelman also tried to conceal the fact that two Brice Marden paintings he sold had been in the Creeks residence during the fire, one of them in the same room as the Twombly and the Warhols.

“When he is looking to sell the Mardens and artwork that was at the Creeks, those artworks are in very good and stable condition,” Mr. Rosenberg told Justice Cohen during his opening statement. “But when he is responding to the insurer’s investigation, he says all Creeks art went through a horrific fire and was damaged.”

The holding companies’ lawyers wrote in a post-trial brief that their client had not intentionally misled insurers, saying: “To the extent Mr. Perelman gave inaccurate testimony, the far more credible explanation is that he simply did not recall the minutiae of every transaction.”

A lawyer for those companies also explained that their client’s insurance arrangements reflected the importance Mr. Perelman, a seasoned collector, placed on maintaining a blue-chip collection. Coverage amounts for the five paintings were not meant to reflect market value, the lawyer said, but a higher number that would allow them to be replaced quickly with other works. And, the lawyer added, the policyholders gave him the ability to surrender to insurers even partly damaged works for their full scheduled value.

During the trial expert witnesses testified for the holding companies about the vulnerabilities of paintings and the distinction between soot and char. One said that the types of plexiglass frames that protected the five paintings were not airtight. Another testified that during the fire those frames would have filled with outside air. A third described how humidity degrades paint, creating structural changes that may not be immediately visible but that would eventually lead to discernible damage.

Lawyers for the insurers countered that their opponents had failed to prove soot, char or humidity damage. They called an explanation by one plaintiff’s expert of how humid outside air would have penetrated into protective frames “unscientific and unreliable” and said discussion of potential effects that may emerge in the future fell short of the “the required showing of perceptible, material, and negative change.”

Mr. Perelman’s direct testimony came near the end of the trial and was brief. He said that after the Creeks fire he noticed the five paintings were different —— “The colors were not as vibrant, the contrast was not as deep” —— but left it to experts to figure out whether the works had been harmed.

He said he had not lied or tried to deceive the insurers while testifying under oath before the trial and that he had not authorized anyone to offer for sale any of the five paintings named in the lawsuit.

But a lawyer representing AIG Property Casualty Company, Charles Michael, cross-examined Mr. Perelman about apparent efforts to sell works from the estate after the fire. He cited an email from 2020 that said Kenneth Griffin, the founder of the investment firm Citadel, would be coming to the Creeks with Mr. Gagosian to look at the Twombly and also a Marden painting, “Letter About Rocks #2,” which is not one of the five paintings that were the subject of the lawsuit.

The email, sent by Mr. Perelman’s assistant, added: “ROP is aware.”

Mr. Perelman told the court that Mr. Gagosian was told that the Twombly was not for sale.

Mr. Griffin ended up purchasing the Marden, which had hung near the Twombly in the dining room, for $30 million.

While under cross-examination, Mr. Perelman expanded on his views on the damage to the Twombly, saying at one point it had also “lost its sense of lyricism.”

A moment later, he reflected further on the work.

“You take the Twombly,” he told the court. “I mean, to some people it just looks like fifth grade scribbles. To me it looks like a symphony orchestra.”