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US 2012/0259088 A1Published application
Copolymers with perfluoropolyether segment and multiple aminooxalylamino groups
Assignee3M Innovative Properties Company
InventorsSuresh S. Iyer, Miguel A. Guerra, Richard G. Hansen, David S. Hays, Ramesh C. Kumar, George G.I. Moore, Yu Yang
Life of this patent
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Abstract
Copolymers containing at least one perfluoropolyether segment and multiple aminooxalylamino groups are described. Methods of making the copolymers are also described. The copolymers can be prepared by reacting an oxalylamino-containing compound and an amine compound having at least two primary amino groups, at least two secondary amino groups, or at least one primary amino group plus at least one secondary amino group.
Claims13
A copolymer comprising a product of a reaction mixture comprising:
- a) a fluorinated oxalylamino-containing compound comprising at least one perfluoropolyether segment and at least two monovalent oxalylamino-containing groups of Formula (Ia)
- wherein the fluorinated oxalylamino-containing compound is of Formula (V), Formula (Va), or Formula (VI), or Formula (VIa)
- wherein
- each R1 is independently an alkyl, haloalkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl, or imino of formula —N═CR4R5;
- each R2 is independently hydrogen, alkyl, aralkyl, or aryl;
- R4 is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl;
- R5 is alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl;
- Rf is a perfluoropolyether group;
- each Y1 is independently (a) a heteroalkylene having at least two carbon atoms, (b) alkylene having at least two carbon atoms, (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each independently a heteroalkylene having at least two carbon atoms or alkylene having at least two carbon atoms, or (d) a combination thereof;
- and
- n is an integer greater than or equal to at least 2;
- each Y2 is independently a single bond, heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- and
- each Y3 is independently a heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- q is an integer equal to at least 1;
- and
- b) a first amine compound of Formula (II)
- wherein
- Q2 is (a) an alkane radical, (b) a heteroalkane radical, (c) an arene radical, (d) a carbonylamino group linking a first group to a second group, where each first group and second group is independently an alkane radical, a heteroalkylene radical, an arene radical, or a combination thereof, (e) part of a heterocyclic group that includes R7 and a nitrogen to which R7 is attached, or (f) a combination thereof;
- each R7 is independently hydrogen, alkyl, aralkyl, aryl, or part of a heterocyclic group that includes Q2 and the nitrogen to which R7 is attached;
- and
- n is an integer equal to at least 2.
19 more elements
2-5. (canceled)
A copolymer comprising a product of a reaction mixture comprising:
- a) a second oxalylamino-containing compound of Formula (III)
- wherein
- each R1 is independently an alkyl, haloalkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl, or imino of formula —N═CR4R5;
- each R7 is independently hydrogen, alkyl, aralkyl, aryl, or part of a heterocyclic group that includes Q and a nitrogen to which R7 is attached;
- R4 is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl;
- R5 is an alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl;
- Q is (a) a heteroalkylene, (b) alkylene, (c) arylene, (d) a carbonylamino group linking a first group to a second group, where each first group and second group is independently a heteroalkylene, alkylene, arylene, or a combination thereof, (e) part of a heterocyclic group that includes R7 and the nitrogen to which R7 is attached, or (f) a combination thereof;
- and
- p is an integer equal to at least 1;
- and
- b) a fluorinated amine having a perfluoropolyether segment and having at least two primary amino groups, two secondary amino groups, or a mixture thereof
- wherein the fluorinated amine is of Formula (VII) or (VIII)
- wherein
- Rf is a perfluoropolyether group;
- and
- each Y1 is independently (a) a heteroalkylene having at least two carbon atoms, (b) alkylene having at least two carbon atoms, (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene having at least two carbon atoms or alkylene having at least two carbon atoms, or (d) a combination thereof
- each R2 is independently hydrogen, alkyl, aralkyl, or aryl;
- n is an integer equal to at least 1;
- each Y2 is independently a single bond, heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- and
- each Y3 is independently a heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof.
18 more elements
9-10. (canceled)
A copolymer comprising at least one group of Formula (IV)
- wherein
- Q1 comprises a perfluoropolyether segment, wherein Q1 is of Formula (X) or (XI)
- each Y1 is independently (a) a heteroalkylene having at least two carbon atoms, (b) alkylene having at least two carbon atoms, or (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene having at least two carbon atoms or alkylene having at least two carbon atoms, or (d) a combination thereof
- each Y2 is independently a single bond, heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- and
- each Y3 is independently a heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- and
- Rf is a perfluoropolyether group;
- Q is (a) a heteroalkylene, (b) alkylene, (c) arylene, (d) a carbonylamino group linking a first group to a second group, where each first group and second group is independently a heteroalkylene, alkylene, arylene, or a combination thereof, (e) part of a heterocyclic group that includes R7 and the nitrogen to which R7 is attached, or (f) a combination thereof;
- and
- each R2 is independently hydrogen, alkyl, aralkyl, or aryl;
- each R7 is independently hydrogen, alkyl, aralkyl, aryl, or a part of a heterocyclic group that includes Q and the nitrogen to which R7 is attached;
- each variable q, p, and m is independently an integer equal to at least 1;
- and
- each asterisk denotes a site of attachment to another group in the copolymer.
12 more elements
13-14. (canceled)
A copolymer comprising a product of a reaction mixture comprising:
- a) an oxalate compound of Formula (IX)
- wherein
- each R1 is independently an alkyl, haloalkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl, or imino of formula —N═CR4R5;
- R4 is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl;
- and
- R5 is an alkyl, aralkyl, substituted aralkyl, aryl, or substituted aryl;
- b) a fluorinated amine having a perfluoropolyether segment and having at least two primary amino groups, two secondary amino groups, or a mixture thereof, wherein the fluorinated amine is of Formula (VII) or (VIII)
- wherein
- Rf is a perfluoropolyether group;
- and
- each Y1 is independently (a) a heteroalkylene having at least two carbon atoms, (b) alkylene having at least two carbon atoms, (c) a carbonylamino group linking a first group to a second group, wherein the first group and the second group are each a heteroalkylene having at least two carbon atoms or alkylene having at least two carbon atoms, or (d) a combination thereof;
- each R2 is independently hydrogen, alkyl, aralkyl, or aryl;
- n is an integer equal to at least 1;
- each Y2 is independently a single bond, heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- and
- each Y3 is independently a heteroalkylene having at least two carbon atoms, alkylene having at least two carbon atoms, or combination thereof;
- and
- c) a first amine compound of Formula (II)
- wherein
- Q2 is (a) an alkane radical, (b) a heteroalkane radical, (c) an arene radical, (d) a carbonylamino group linking a first group to a second group, where each first group and second group is independently an alkane radical, a heteroalkylene radical, an arene radical, or a combination thereof, (e) part of a heterocyclic group that includes R7 and a nitrogen to which R7 is attached, or (f) a combination thereof;
- each group R7 is independently hydrogen, alkyl, aralkyl, aryl, or part of a heterocyclic group that includes Q2 and the nitrogen to which R7 is attached;
- and
- n is an integer equal to at least 2.
20 more elements
Dependencies are inferred from the claim text.