IP Library Granted Patent US 9,702,081
Granted Patent B2
US 9,702,081 · App. 14/852,842 · Granted Jul 11, 2017

Polyurethanes derived from non-fluorinated or partially fluorinated polymers

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Quick Facts
Patent No.
US 9,702,081
App. No.
14/852,842
Granted
Jul 11, 2017
Kind
B2
Abstract

Polymers are described having repeat units of Formula (I): wherein R 3 is H or alkyl group; x and t are positive integers; Q is C(O)O, C(O)NH, or direct bond; D is alkylene, arylene, or (CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m ; E is O, S, NR 5 , or direct bond; R 5 is H or alkyl; G is the residue of a polyisocyanate; V is a urethane, urea, or thiourea that bonds to other parts of the polymer compound or to a monovalent blocking group; s is 1 to 5; Y is O or a substituted or unsubstituted arylene group; A is an alkylene group; w, v, and y are 0 or 1; X is the residue of a cyclic or acyclic sugar alcohol which is substituted with —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; n and m are independently 0 to 20; R 1 is independently an alkyl group; and R 2 is independently —H or alkyl group.

Claims (49)

1. A polymer compound comprising the repeat units of Formula (I):

wherein

R 3 is selected from H or a C 1 to C 4 alkyl group;

x and t are integers from 1 to 200;

Q is C(O)O, C(O)NH, or a direct bond;

D is a C 1 to C 6 linear or branched alkylene, an arylene group, or (CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m ,

E is O, S, NR 5 , or a direct bond;

provided that E is a direct bond when D is (CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m ;

R 5 is H or a monovalent C 1 to C 6 alkyl;

G is the residue of a diisocyanate or polyisocyanate;

V is a group selected from urethane, urea, or thiourea that bonds to other parts of the polymer compound or to a monovalent blocking group;

s is 1 to 5;

Y is selected from O, a substituted arylene group, or an unsubstituted arylene group;

A is a linear or branched C 1 to C 10 alkylene group;

w is 0 or 1;

v is 0 or 1;

y is 0 or 1;

provided that w+y is at least 1; if w is 0 then Y is a substituted or unsubstituted arylene group; and if Y is O then v is 1;

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.

2. The polymer compound of claim 1 wherein X is at least 50% bio-based derived.

3. The polymer compound of claim 1 wherein X is 100% bio-based derived.

4. The polymer compound of claim 1 wherein X is selected from Formulas (IIa), (IIb), or (IIc):

wherein each R is independently a direct bond to C═O of Formula I, —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 ;

n and m are defined as above;

m+n is greater than 0;

r is 1 to 3;

a is 0 or 1;

p is independently chosen from 0 to 2;

provided that a is 0 when r is 3;

each R 1 and R 2 are defined as above;

provided when X is Formula (IIa), then one R is a direct bond to C═O of Formula 1; and at least one R is a —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 R 4 is independently a direct bond to C═O of Formula I; —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 one R or R 4 is a direct bond to C═O of Formula 1; and at least one R or R 4 is a linear or branched alkyl group 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 ; and

each R 19 is a direct bond to C═O of Formula I, —H, —C(O)R 1 , or —CH 2 C[CH 2 OR] 3 ,

provided when X is Formula (IIc), then one R 19 or R is a direct bond to C═O of Formula I; and at least one R 19 or R is —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 .

5. The polymer compound of claim 4 wherein X is selected from Formula (IIa) to be Formula (IIa′):

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

6. The polymer compound of claim 4 wherein X is selected from Formula (IIa) to be Formula (IIa′):

wherein R is further limited to independently a direct bond to C═O, —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 .

7. The polymer compound of claim 4 wherein X is selected from formula (IIb).

8. The polymer compound of claim 4 wherein X is selected from formula (IIc).

9. The polymer composition of claim 1 wherein G is selected from Formulas (IIIa), (IIIb), (IIIc), (IIId), or (IIIe):

10. The polymer composition of claim 1 , where at least one V is bonded to at least one blocking group selected from a C 1 to C 30 linear or branched alkyl optionally comprising at least one unsaturated group, a linear or branched C 1 to C 30 polyether, a residue X as defined above, or a C 1 to C 20 linear or branched fluoroalkyl optionally interrupted by O, CH 2 , CH 2 CH 2 , or SO 2 NH.

Assignments (2)
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2015
From: SWOREN, JOHN CHRISTOPHER; BROWN, GERALD ORONDE; HAIDZINSKAYA, TATSIANA; KOHLER, EWA
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 037002/0922 →