Non-fluorinated and partially fluorinated polymers

Patent metadata

Field	Value
Publication number	US-10047245-B2
Application number	US-201514862293-A
Country	US
Kind code	B2
Filing date	Sep 23, 2015
Priority date	Sep 26, 2014
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

A polymer composition with (A) a first poly(meth)acrylate polymer or urethane polymer; and (B) a second poly(meth)acrylate polymer or urethane polymer which has a residue X incorporated therein, where X is the residue of a cyclic or acyclic sugar alcohol which is substituted with at least one —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ; or mixtures thereof; where the cyclic or acyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond; and each R 2 is independently —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or mixtures thereof.

First claim

What is claimed is:

1. A polymer composition comprising
A) a first polymer selected from a poly(meth)acrylate polymer or a urethane polymer; and
B) a second polymer selected from a urethane polymer comprising linkages of Formula I:
-Q-NHC(O)—X  (I)

or a poly(meth)acrylate polymer comprising repeat units of Formula (II):

wherein
the second polymer comprises 20 to 100 mol % of structures of Formula (I) or Formula (II);
Q is the residue of an isocyanate, diisocyanate, or polyisocyanate;
X is the residue of a cyclic or acyclic sugar alcohol which is substituted with at least two —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ; or mixtures thereof;
where the cyclic or acyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein
each n is independently 0 to 20;
each m is independently 0 to 20;
m+n is greater than 0;
each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond; and
R 3 is selected from H or a C 1 to C 4 alkyl group;
A is a linear or branched C 1 to C 10 alkylene group;
x is an integer from 1 to 200; and
y is 0 or 1.

2. The polymer composition of claim 1 , where X is at least 50% bio-based derived.

3. The polymer composition of claim 1 , where X is selected from Formulas (IIIa), (IIIb), or (IIIc):

wherein each R is independently a direct bond to C(O) of Formula I or Formula II; H; —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ;

or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;
each n is independently 0 to 20;
each m is independently 0 to 20;
m+n is greater than 0;
r is 1 to 3;
a is 0 or 1;
p is independently 0 to 2;
provided that a is 0 when r is 3;
each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond;
each R 2 is independently —H, or a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond;
or a mixtures thereof,
provided when X is Formula (IIIa), then at least one R is a direct bond to C(O) of Formula I or Formula II; and at least two R is a —R 1 ; —C(O)R 1 ;

or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;
each R 4 is independently a direct bond to C(O) of Formula I or Formula II, —H, a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or combinations thereof; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ,

or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ;
provided when X is Formula (IIb), then at least one R or R 4 is a direct bond to C(O) of Formula I or Formula II; and at least two R or R 4 is a linear or branched alkyl group optionally comprising at least 1 unsaturated bond, or combinations thereof;

or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ; and
each R 19 is a direct bond to C(O) of Formula I or Formula II, —H, —C(O)R 1 , or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ,
provided when X is Formula (IIc), then at least one R 19 or R is a direct bond to C(O) of Formula I or Formula II; and at least two R 19 or R is —C(O)R 1 ,

or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

4. The polymer composition of claim 3 wherein X is selected from Formula (IIIa) to be Formula (IIIa′):

wherein R is further limited to independently a direct bond to C(O) of Formula I or Formula II, —H, —R 1 , or —C(O)R 1 .

5. The polymer composition of claim 3 wherein X is selected from Formula (IIIa) to be Formula (IIIa′):

wherein R is further limited to independently a direct bond to C(O) of Formula I or Formula II, —H; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or

—(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .

6. The polymer composition of claim 1 , wherein the second polymer (B) is a poly(meth)acrylate polymer.

7. The polymer composition of claim 6 , having a core-shell structure selected from a poly(meth)acrylate polymer (B) core and poly(meth)acrylate polymer (A) shell, a poly(meth)acrylate polymer (B) core and urethane polymer (A) shell, or a urethane (A) core and poly(meth)acrylate polymer (B) shell.

8. The polymer composition of claim 1 , wherein the second polymer (B) is a urethane polymer.

9. The polymer composition of claim 8 , having a core-shell structure selected from a urethane polymer (B) core and poly(meth)acrylate polymer (A) shell or a poly(meth)acrylate polymer (A) core and urethane polymer (B) shell.

10. The polymer composition of claim 1 , wherein the first polymer (A) is chemically bonded to the second polymer (B).

11. The polymer composition of claim 1 , where one or more of the first or second polymers contains fluoroalkyl functional groups.

12. The polymer composition of claim 8 , wherein the second polymer further comprises at least one linkage selected from Formulas (IVa), (IVb), (IVc), or mixtures thereof:
R 6 -D  (IVa),

R 15 —(OCH 2 CH(OR 16 )CH 2 ) z —OR 17   (IVb),

—NH—C(O)—NH—X  (IVc)

wherein D is selected from —N(R 12 )—C(O)—NH—, —OC(O)NH—, —C(O)NH—, —SC(O)NH—, —O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —C(O)NH—, or —[C(O)]—O—(CH 2 CH 2 O) s (CH(CH 3 )CH 2 O) t —C(O)NH—;
X is defined as above;
R 6 is selected from a —C 1 to C 30 linear or branched alkyl optionally comprising at least one unsaturated group, a C 1 to C 20 linear or branched fluoroalkyl optionally interrupted by O, CH 2 , CH 2 CH 2 , or SO 2 NH, a hydroxy- or urethane-functional C 1 to C 30 linear or branched alkyl, a hydroxy- or urethane-functional linear or branched C 1 to C 30 polyether, a hydroxy- or urethane-functional linear or branched polyester having a polyester polymer backbone, a hydroxy- or urethane-functional linear or branched organosiloxane, an amine- or urea-functional linear or branched organosiloxane, a thiol- or thiocarbonate functional C 1 to C 30 linear or branched alkyl, an amine- or urea-functional C 1 to C 30 linear or branched alkyl,

wherein
R 7 , R 8 , and R 9 are each independently, —H, —C 1 to C 6 alkyl, or combinations thereof;
R 19 is a divalent alkyl group of 1 to 20 carbons;
R 12 is —H or a monovalent C 1 to C 6 alkyl group;
R 15 , R 16 , and R 17 are each independently a —H; —C(O)NH—, —R 18 ; —C(O)R 18 provided that at least one R 15 , R 16 , or R 17 is a —C(O)NH—;
R 18 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond;
z is 1 to 15;
Y is Cl;
s is an integer of 0 to 50;
t is an integer of 0 to 50; and
s+t is greater than 0.

13. The polymer composition of claim 6 , wherein the second polymer further comprises at least one repeat unit from an ethylenically unsaturated monomer selected from linear or branched alkyl (meth)acrylates, amino and diamino (meth)acrylates, linear or branched fluoroalkyl (meth)acrylates optionally interrupted by O, CH 2 , CH 2 CH 2 , or SO 2 NH, a

Assignees

• Chemours Co Fc Llc
• Chemours Co Fc Llc

Inventors

• Sworen John Christopher
• Brown Gerald Oronde
• Haidzinskaya Tatsiana

Classifications

• C08G18/792 Primary

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• D06M15/564

  Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them · CPC title

• C08G18/7831

  containing biuret groups · CPC title

• C08G18/3221

  hydroxylated esters of carboxylic acids other than higher fatty acids · CPC title

• C09D175/04 Primary

  Polyurethanes · CPC title