Non-fluorinated monomers and polymers for surface effect compositions

Patent metadata

Field	Value
Publication number	US-9915025-B2
Application number	US-201514847161-A
Country	US
Kind code	B2
Filing date	Sep 8, 2015
Priority date	Sep 26, 2014
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

The present invention relates to monomers and polymers of Formula (I):

where R 3 is selected from H or a C 1 to C 4 alkyl group; Y is selected from O or a substituted or 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; 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 ; each n is independently 0 to 20; each m is independently 0 to 20; each R 1 is independently a linear or branched alkyl group having 9 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 compound of Formula (I):

where
R 3 is selected from H or a C 1 to C 4 alkyl group;
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 1 or 2; 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;
provided that if y is 1, then 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 9 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 compound of claim 1 wherein X is at least 50% bio-based derived.

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

4. The 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 (I); 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 (I); 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 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 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 compound of claim 4 wherein X is selected from formula (IIb).

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

9. A composition comprising a mixture of compounds of claim 1 .

10. A method of preparing a compound comprising reacting (a) a compound selected from Formula (III)

with (b) at least one 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;
provided that if y is 1, then 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 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;
R 3 is selected from H or a C 1 to C 4 alkyl group;
w is 0 or 1;
v is 0 or 1;
y is 0 or 1;
Z is selected from a halide, —OC(O)CR 3 ═CH 2 , —OH, or —NH 2 when y is 0 and Z is —NCO when y is 1;
provided that w+y is 1 or 2; if w is 0 then Y is a substituted or unsubstituted arylene group; and if Y is O then v is 1;
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 9 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.

11. The method of claim 10 , where the at least one cyclic or acyclic sugar alcohol which is substituted is selected from formula (IVa), (IVb), or (IVc):

wherein each R 5 is independently —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 a compound of Formula (IVa) is used, then at least one R 5 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 6 is independently —H, a linear or branched alkyl group having 10 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 a compound of Formula (IVb) is used, then at least one R 5 or R 6 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 7 is —H, —C(O)R 1 , or —CH 2 C[CH 2 OR 5 ] 3 ,
provided when a compound of Formula (IVc) is used, then at least one R 7 or R 5 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

Assignees

• Chemours Co Fc Llc

Inventors

• Sworen John Christopher
• Brown Gerald Oronde
• Haidzinskaya Tatsiana

Classifications

• D21H19/20

  comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• D21H19/58

  Polymers or oligomers of diolefins, aromatic vinyl monomers or unsaturated acids or derivatives thereof · CPC title

• D06M15/263 Primary

  of unsaturated carboxylic acids; Salts or esters thereof · CPC title

• D06M15/233

  aromatic, e.g. styrene · CPC title

• D06M15/3562

  containing nitrogen · CPC title