Granted Patent B2

US 12,522,685 · App. 17/756,323 · Granted Jan 13, 2026

Inventors: George W. Griesgraber (Eagan, MN); Federica Sgolastra (Woodbury, MN); Semra Colak Atan (Saint Louis Park, MN)

Assignee: Solventum Intellectual Properties Company

C08F293/00C09D153/00

Abstract

Claims (56)

1 . A composition comprising:

a triblock copolymer comprising:

one A block comprising multiple monomeric units derived from a first monomer comprising a (meth)acryloyl group and a phosphorus-containing group; and

two B blocks with each B block comprising multiple monomeric units derived from a second monomer selected from at least one of:

C n F (2n+1) (CH 2 ) z OC(═O)CR 5 ═CH 2 (Formula (II)), wherein n is an integer selected from 1 to 6, z is an integer selected from 1 to 20, and R 5 is H or CH 3 ; or

C p F (2p+1) SO 2 (NR 6 )(CH 2 ) q OC(═O)CR 7 ═CH 2 (Formula (III)), wherein p is an integer selected from 1 to 6, q is an integer selected from 2 to 20, R 6 is H or C1-C8 alkyl group, and R 7 is H or CH 3 ;

wherein the triblock copolymer comprises 1 to 30 weight percent A block and 70 to 99 weight percent B block based on a total weight of the block copolymer; and

one or more organic solvents, wherein the block copolymer is dissolved or dispersed in the organic solvents.

2 . The composition of claim 1 , wherein the first monomer is of Formula (I)

CH 2 =CR 1 —(CO)—X 1 —R 2 -[-Q 1 -R 3 —] m —Y   (I)

wherein

R 1 is hydrogen or methyl;

X 1 is oxy or —NR 4 —;

R 2 is an alkylene or heteroalkylene;

R 3 is an alkylene;

Q 1 is —(CO)X 2 —, —NR 4 —(CO)—X 2 —;

X 2 is oxy or —NR 4 —;

R 4 is hydrogen or alkyl;

m is 0 or 1; and

Y is a phosphorus-containing group.

3 . The composition of claim 2 , wherein Y is —P(O)(OH) 2 .

4 . The composition of claim 3 , wherein the first monomer is of Formula (I-A), wherein m=0:

CH 2 =CR 1 —(CO)—X 1 —R 2 -Y   (I-A).

5 . The composition of claim 4 , wherein the first monomer is CH 2 ═CH—(CO)—O—CH 2 CH 2 —P(O)(OH) 2 .

6 . A composition, comprising:

a triblock copolymer comprising:

one A block comprising multiple monomeric units derived from a first monomer of formula (I-B):

CH 2 =CR 1 —(CO)—X 1 —R 2 -Q 1 -R 3 —Y   (I-B)

wherein Y═PO(OH) 2 ; and

two B blocks with each B block comprising multiple monomeric units derived from a second monomer selected from at least one of:

C n F (2n+1) (CH 2 ) z OC(═O)CR 5 ═CH 2 (Formula (II)), wherein n is an integer selected from 1 to 6, z is an integer selected from 1 to 20, and R 5 is H or CH 3 ; or

C p F (2p+1) SO 2 (NR 6 )(CH 2 ) q OC(═O)CR 7 ═CH 2 (Formula (III)), wherein p is an integer selected from 1 to 6, q is an integer selected from 2 to 20, R6 is H or C1-C8 alkyl group, and R7 is H or CH 3 ; and

one or more organic solvents, wherein the block copolymer is dissolved or dispersed in the organic solvents.

7 . The composition of claim 6 , wherein the first monomer is CH 2 ═CH—(CO)—NH—C(CH 3 ) 2 —(CO)—NH—CH 2 CH 2 —P(O)(OH) 2 or CH 2 =CR 1 —(CO)—O—CH 2 CH 2 —NH—(CO)—NH—CH 2 CH 2 —P(O)(OH) 2 .

8 . The composition of claim 1 , wherein the second monomer is of Formula (II), wherein n is an integer selected from 1 to 6, z is an integer selected from 1 to 6, and R 5 is H or CH 3 .

9 . The composition of claim 1 , wherein the second monomer is of Formula (III), wherein p is an integer selected from 1 to 6, q is an integer selected from 2 to 4, R 6 is H or C1-C3 alkyl group, and R 7 is H or CH 3 .

10 . The composition of claim 1 , wherein the second monomer is selected from:

CF 3 CF 2 CF 2 CH 2 —O—C(═O)C(CH 3 )═CH 2 ; and

CF 3 CF 2 CF 2 CF 2 —S(═O)2N(CH 3 )CH 2 CH 2 —O—C(═O)C(CH 3 )═CH 2 .

11 . The composition of claim 1 , wherein the block copolymer is of Formula (VIII):

wherein:

R 10 is an alkyl, alkoxy, or group of formula —N(R 12 ) 2 ;

R 11 is an alkoxy or a group of formula —N(R 13 ) 2 ;

each R 1-3 is an alkyl;

each A is a first polymeric block that is a polymerized product of a first polymerizable composition comprising first monomers of Formula (I):

CH 2 ═CR 1 —(CO)—X 1 —R 2 -[-Q 1 -R 3 —] m —Y  (I); and

each B is a second polymeric block that is a polymerized product of a second polymerizable composition comprising monomers of Formulas (II) and/or (III).

12 . An article comprising:

a) a metal-containing substrate; and

b) a coating layer positioned adjacent to the substrate, wherein the coating layer comprises a block copolymer of claim 1 .

13 . A composition comprising:

a triblock copolymer comprising:

one A block comprising multiple monomeric units derived from a first monomer comprising a (meth)acryloyl group and a phosphorus-containing group; and

two B blocks with each B block comprising multiple monomeric units derived from a second monomer of Formula (III),

C p F (2p+1) SO 2 (NR 6 )(CH 2 ) q OC(═O)CR 7 ═CH 2   (Formula (III)),

wherein p is an integer selected from 1 to 6, q is an integer selected from 2 to 4, R 6 is H or CI-C3 alkyl group, and R 7 is H or CH 3 .

Assignments (2)

Continuity (1)

References Cited (24)