Isocyanate derived organosilanes

Patent metadata

Field	Value
Publication number	US-10011617-B2
Application number	US-201514847199-A
Country	US
Kind code	B2
Filing date	Sep 8, 2015
Priority date	Sep 26, 2014
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

The invention relates to isocyanate derived organosilanes and the use thereof. The isocyanate derived organosilanes can be reacted with inorganic substrates, such as oxide particles, to result in a surface modified inorganic substrate.

First claim

What is claimed is:

1. An organosilane represented by Formula (I)

wherein:
x is an integer from 1 to 12;
L is independently chosen from H, C 1 -C 2 alkyl, or OR, where R is H or C 1 -C 4 alkyl; and
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 ;
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 (IIa′), then 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 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 at least one R 19 or R is —C(O)R 1 , or —CH 2 C[CH 2 OR] 3 .

2. The organosilane of claim 1 wherein the moieties X of formula (IIa′), (IIb′), and (IIc′) are at least 50% bio-based derived.

3. The organosilane of claim 1 wherein the moieties X of formula (IIa′), (IIb′), and (IIc′) are 100% bio-based derived.

4. The organosilane of claim 1 wherein X is selected from formula (IIa′) wherein the values of R which are not directly bonded to C═O are selected from —H; —R 1 ; or —C(O)R 1 .

5. The organosilane of claim 1 wherein X is selected from formula (IIa′) wherein the values of R which are not directly bonded to C═O are selected from —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 organosilane of claim 1 wherein X is selected from formula (IIb′).

7. The organosilane of claim 1 wherein X is selected from formula (IIc′).

8. Surface modified inorganic oxide particles comprising an oxide of M, at least one of said particles having a surface covalently bonded to at least one organosilane group represented by Formula (IV):

wherein:
x is an integer from 1 to 12;
L 1 represents an oxygen covalently bonded to an M; each L 2 independently selected from the group consisting of H, a C 1 -C 2 alkyl, and OH; d and c are integers such that: d≥1, c≥0, d+c=3;
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 ;
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 (IIa′), then 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 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 at least one R 19 or R is —C(O)R 1 , or —CH 2 C[CH 2 OR] 3 .

9. The surface modified inorganic oxide particles of claim 8 , wherein M is Ti.

10. The organosilane of claim 1 wherein formula (IIa) is further defined as formula (IIaa′):

wherein R is independently a direct bond to C═O of Formula (I), —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 .

11. The organosilane of claim 1 wherein formula (IIa) is further defined as formula (IIaa′)

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

12. The surface modified inorganic oxide particles of claim 8 , further comprising an at least partial surface coating.

13. The organosilane of claim 1 , wherein the organosilane is blended with at least one fluorosilane.

14. The organosilane of claim 1 , wherein L is CH 3 .

15. An organosilane represented by Formula (I)

wherein:
x is an integer from 1 to 12;
L is independently chosen from a H, C 1 -C 2 alkyl, or OR, where R is H or C 1 -C 4 alkyl; and
X is at least one residue of an ester of a cyclic or acyclic sugar alcohol which is substituted with at least one —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 glucose, glyceraldehyde, erythrose, arabinose, ribose, arabinose, allose, altrose, mannose, xylose, lyxose, gulose, glactose, talose, fructose, ribulose, mannoheptulose, sedohelptulose, threose, erythritol, threitol, glucopyranose, mannopyranose, talopyranose, allopyranose, altropyranose, idopyranose, gulopyranose, glucitol, mannitol, erythritol, sorbitol, arabitol, xylitol, ribitol, galactitol, fucitol, iditol, inositol, pentaerythritol, dipentaerythritol, volemitol, gluconic acid, glyceric acid, xylonic acid, galactaric acid

Assignees

• Chemours Co Fc Llc
• Chemours Co Fc Llc

Inventors

• Sworen John Christopher
• Brown Gerald Oronde
• Haidzinskaya Tatsiana
• Kohler Ewa

Classifications

• C09C1/309

  Combinations of treatments provided for in groups C09C1/3009 - C09C1/3081 · CPC title

• C09C1/407

  Aluminium oxides or hydroxides · CPC title

• C09C1/043

  Zinc oxide · CPC title

• C09C1/3081

  Treatment with organo-silicon compounds · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title