Silanol compositions and methods of use

Patent metadata

Field	Value
Publication number	US-12312495-B2
Application number	US-201917284521-A
Country	US
Kind code	B2
Filing date	Oct 8, 2019
Priority date	Oct 18, 2018
Publication date	May 27, 2025
Grant date	May 27, 2025

Abstract

Described herein are compositions including a silanol compound that is suitably synthesized, stored, and coated from an aqueous solution. Once coated and cured on a suitable surface, the aqueous silanol compositions result in cleanable and abrasion resistant surfaces, such as dry-erase surfaces that release permanent marker by rubbing with a dry cloth or towel. Also disclosed herein are methods of making the silanol compounds, methods of making cleanable substrates, and cleanable substrates suitably formed using the disclosed methods.

First claim

What is claimed is:

1. A silanol compound having the structure
Y p —X—Z q

wherein
Y is [(R 1 O) i R 2 j Si], each R 1 is hydrogen, each R 2 is independently an alkyl group having 1 to 6 carbons, i is an integer between 1 and 3, j is an integer between 0 and 2, and i+j=3;
Z is [N(R 3 )(R 4 )—(CH 2 ) m —C(G 1 a )-G 2 b ] wherein each G 1 is independently selected from H and OH and each G 2 is independently selected from SO 3 , OSO 3 , CO 2 , or a protonated or salt form thereof, a is 0 to 2, b is 1-2, and a+b=3, R 3 is hydrogen or an alkyl, aryl, or alkaryl group having 1 to 18 carbons, R 4 is an electron pair that is uncoordinated or is coordinated to a hydrogen atom, and m is an integer between 2 and 10;
p and q are independently integers having a value of 1 to 1000, further wherein the ratio of p:q is between 2:1 and 1:10;
each of p moieties Y is the same or different, and each of q moieties Z is the same or different; and
X is a linking group comprising covalent bonds linking one or more moieties Y to one or more moieties Z;
or a structure corresponding to one of the following structures 17, 18, or 19 or a protonated form thereof or a salt thereof:

2. The silanol compound of claim 1 wherein one or more R 4 is an electron pair that is coordinated to a hydrogen atom.

3. The silanol compound of claim 1 wherein one or more m is 2 or 3.

4. The silanol compound of claim 1 , wherein at least one G 1 is H.

5. The silanol compound of claim 1 , wherein a is 2.

6. The silanol compound of claim 1 , wherein at least one G 2 is SO 3 or a protonated or salt form thereof.

7. The silanol compound of claim 1 , wherein X is hydrocarbyl.

8. The silanol compound of claim 1 , wherein at least one G 1 is OH.

9. The silanol compound of claim 8 , wherein exactly one G 1 is OH.

10. The silanol compound of claim 1 , wherein a is 1.

11. The silanol compound of claim 1 , wherein b is 2.

12. The silanol compound of claim 1 , wherein X is hydrocarbyl.

13. The silanol compound of claim 1 , wherein X is hydrocarbyl interrupted by one O atom.

14. The silanol compound of claim 1 , wherein X comprises the moiety —OCH 2 CH(OH)—CH 2 —, and wherein the CH 2 radical is covalently bonded to a nitrogen atom of Z.

15. The silanol compound of claim 1 wherein p=q=1.

16. A silanol compound, which is any of compound 1 through compound 21:

17. A composition comprising water and a silanol compound according to claim 1 .

18. The composition of claim 17 wherein the silanol compound further comprises a lithium counterion.

Assignees

• 3M Innovative Properties Company

Inventors

• Ma Jun
• Jing Naiyong
• David Moses M

Classifications

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C08G77/54

  Nitrogen-containing linkages · CPC title

• C07F9/3873

  containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S) · CPC title

• C07F9/3817

  Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se) · CPC title

• C07F7/0836

  Compounds with one or more Si-OH or Si-O-metal linkage · CPC title