Fluorinated polyisocyanates

• US 5,605,956 A
• Filed: 10/16/1995
• Issued: 02/25/1997
• Est. Priority Date: 10/16/1995
• Status: Expired due to Term

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Graham, William F., Thomas, Richard R., Darmon, Michael J., Anton, Douglas R.
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): NILAND, PATRICK DENNIS
• Application Number:
  US08/543,773
• Time in Patent Office: 498 Days
• Field of Search: 528/70, 568/842, 524/590, 524/539, 525/123, 525/455
• US Class Current: 524/590
• CPC Class Codes: C08G 65/007 containing fluorine

Abstract

A fluorinated polyisocyanate which comprises an organic polyisocyanate reacted with a fluorinated monofunctional alcohol represented by the formula ##STR1## where R_f is a fluoroalkyl containing group having at least 4 carbon atoms, X is a divalent radical, R³ is H or an alkyl group having 1-4 carbon atoms, n is 0-1 and m is 0-30, provided that when n is 0 then m must be equal to or greater than 1 and when m is 0, n is 1, wherein about 0.1-33 mole percent of active isocyanate groups are reacted with the fluorinated monofunctional alcohol; the fluorinated polyisocynate can be used with acrylic polymers, polyesters, alkyd resins, polyols and the like to form coating compositions, sealants, adhesives and the like.

Claims

1. A fluorinated polyisocyanate which comprises an organic polyisocyanate reacted with a fluorinated monofunctional alcohol represented by the formula ##STR8## where R_f is a fluoroalkyl containing group having at least 4 carbon atoms, X is a divalent radical, R³ is H or an alkyl group having 1-4 carbon atoms, n is 1 and m is 1-30, wherein about 0.1-10 mole percent of active isocyanate groups are reacted with the fluorinated monofunctional alcohol.

2. The fluorinated polyisocyanate of claim 1 in which R_f is a straight chain or branched chain perfluoroalkyl group having 4-20 carbon atoms.

3. The fluorinated polyisocyanate of claim 2 in which X is --O--, --CH₂ CH₂ O--, --CH₂ O--, --SO₂ N(R⁴)CH₂ CH₂ O--, --CH₂ -- where R⁴ is an alkyl group having 1-4 carbon atoms, R₃ is H or methyl.

4. The fluorinated polyisocyanate of claim 1 in which the organic polyisocyanate is an aromatic diisocyanate, aliphatic diisocyanate, cycloaliphatic diisocyanate, aromatic triisocyanate, aliphatic triisocyanate, cycloaliphatic triisocyanate or an oligomer of a diisocyanate.

5. A process for forming the fluorinated polyisocyanate of claim 1, which comprises reacting a fluorinated monofunctional alcohol represented by the formula ##STR9## where R_f is a fluoroalkyl group containing at least 4 carbon atoms, X is a divalent radical, R³ is H or an alkyl group having 1-4 carbon atoms, n is 1 and m is, 1-30 with an organic polyisocyanate in the presence of a catalyst and reacting about 0.1-10 mole percent of active isocyanate groups with the fluorinated monofunctional alcohol.

6. A composition comprising the fluorinated polyisocyanate of claim 1 and a film forming polymeric binder.

7. The composition of claim 6 in which the binder is an acrylic polymer, a polyester, an alkyd resin, a polyol or mixture of any of the above.

8. The composition of claim 6 in which the composition contains a solvent for the fluorinated polyisocyanate and polymeric binder.