Perfluoropolyether amide-linked phosphonates, phosphates, and derivatives thereof
Assignee3M Innovative Properties Company
InventorsRichard M. Flynn, Mark J. Pellerite
Life of this patent
Estimating the term…
Abstract
Perfluoropolyether amide-linked phosphonates and derivatives thereof are provided. Compositions containing perfluoropolyether amide-linked phosphonates or derivatives thereof, perfluoropolyether amide-linked phosphates or derivatives thereof, or combinations thereof are also provided. Additionally, articles, methods of making articles, and methods of reducing contaminant adhesion to a substrate are described.
Claims23
A composition comprising organic solvent and a compound dissolved or dispersed the organic solvent, the compound according to Formula I:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, cycloalkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 is a divalent group selected from an alkylene, arylene, or combinations thereof optionally containing a divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein alkylene optionally contains at least one ether group, and wherein R2 is unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof.
A composition comprising a hydrofluoroether and a compound according to Formula I, Formula II, or combinations thereof:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, cycloalkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 comprises a divalent group selected from an alkylene, arylene, heteroalkylene, or combinations thereof and an optional divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein R2 is unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof;
- wherein the hydrofluoroether is represented by formula
- Rf1O—Rh]a,
- wherein
- a is an integer of 1 to 3;
- Rf1 is a monovalent, divalent, or trivalent radical of a perfluoroalkane, perfluoroether, or perfluoropolyether;
- and
- Rh is an alkyl or heteroalkyl.
A composition comprising a fluorinated silane, and a compound according to Formula I, Formula II, or combinations thereof dissolved or dispersed in an organic solvent:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, cycloalkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 comprises a divalent group selected from an alkylene, arylene, or combinations thereof optionally containing a divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein alkylene optionally contains at least on ether group, and wherein R2 is unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof.
A non-aqueous composition comprising a compound dissolved or dispersed in organic solvent, said compound being of Formula I:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 is a divalent group selected from an alkylene, arylene, or combinations thereof optionally containing a divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein alkylene optionally contains at least one ether group, and wherein R2 unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof.
A method of reducing contaminant adhesion to a substrate, said method comprising applying a coating composition to a surface of the substrate, said coating composition comprising organic solvent and a compound dissolved or dispersed in the organic solvent, the compound according to Formula I, Formula II, or combinations thereof:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 comprises a divalent group selected from an alkylene, arylene, heteroalkylene, or combinations thereof and an optional divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein R2 is unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof.
A method of making an article, said method comprising applying a coating composition to a surface of the article, said coating composition comprising organic solvent and a dissolved or dispersed in the organic solvent, the compound according to Formula I:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 comprises a divalent group selected from an alkylene, arylene, heteroalkylene, or combinations thereof and an optional divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein R2 is unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof.
A method of making an article, said method comprising applying a coating composition to a surface of the substrate, said coating composition comprising a first component and a second component dissolved or dispersed in organic solvent:
- a) the first component selected from a hydrofluoroether, fluorinated silane, or combinations thereof:
- and
- b) the second component selected from a compound according to Formula I, Formula II, or a combination of compounds according to Formulas I and II:
- wherein
- Rf is a monovalent or divalent perfluoropolyether group;
- y is equal to 1 or 2;
- each X is independently hydrogen, alkyl, alkali metal, ammonium, ammonium substituted with an alkyl or cycloalkyl, or a five to seven membered heterocyclic group having a positively charged nitrogen atom;
- R1 is hydrogen or alkyl;
- and
- R2 is a divalent group selected from an alkylene, arylene, or combinations thereof optionally containing a divalent group selected from carbonyl, carbonyloxy, carbonylimino, sulfonamido, or combinations thereof, wherein alkylene optionally contains at least one ether group, and wherein R2 is unsubstituted or substituted with an alkyl, aryl, halo, or combinations thereof;
- wherein the hydrofluoroether is represented by formula
- Rf1O—Rh]a,
- wherein
- a is an integer of 1 to 3;
- Rf1 is a monovalent, divalent, or trivalent radical of a perfluoroalkane, perfluoroether, or perfluoropolyether;
- and
- Rh is an alkyl or heteroalkyl.
Dependencies are inferred from the claim text.