Poly fluorine-containing siloxane coatings

Patent metadata

Field	Value
Publication number	US-10150889-B2
Application number	US-201414916844-A
Country	US
Kind code	B2
Filing date	Sep 8, 2014
Priority date	Sep 16, 2013
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

Poly fluorine-containing siloxane coatings having improved hydrophobic and oleophobic properties and solutions for creating such coatings are provided. In some embodiments, the coating includes a polymer having a plurality of Si—O—Si linkages; and at least two fluorine-containing moieties, each attached to at least one of the Si—O—Si linkages. Each fluorine-containing moiety independently includes a linking portion attached to a silicon of one of the Si—O—Si linkages, wherein the linking portion is of a formula selected from the group consisting of: —[CH2]a— where a is an integer from 1 to 10 and —[CH2]bCONH[CH2]c— where b and c are independently an integer from 0 to 10. Each fluorine-containing moiety also independently includes a fluorinated portion attached to the linking portion, wherein the fluorinated portion is selected from a fluorinated-alkyl group having 1-10 carbon atoms and a perfluoro-ether containing organic group.

First claim

The invention claimed is:

1. A composition for forming a poly fluorine-containing siloxane coating comprising:
a polymer of Formula (I):

wherein:

R is a hydrogen atom, an alkyl or aryl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl or aryl group having 1 to 10 carbon atoms;
Rf is a linear or branched perfluoro-alkyl group represented by the formula F—C g F 2g )—, where g is an integer from 1 to 10;
W 1 , W 2 are each independently a perfluoroether-containing organic group;
Q 1 , Q 2 , Q 3 , Q 4 are each independently an organic linking group linking a Si element to a fluorinated group, wherein Q 1 , Q 2 , Q 3 , Q 4 are independently represented by an isolated repeated formula selected from the group consisting of: —CH 2 —, —OCONH—, —COO—, —CONH—, —CH 2 O—, —CH(CH 3 )—, —(CH 3 ) 2 —, and —(Si(CH 3 ) 2 O) h —Si(CH 3 ) 2 —, wherein h is independently an integer from 0 to 10 for each of Q 1 , Q 2 , Q 3 , Q 4 ; and wherein each R is independently selected from the group consisting of H, CH 3 , and CHF 2 ; and
a, c, d, e are each independently an integer from 0 to 1000, b is an integer from 1 to 1000; the sum of the integers a, b, and c being greater than or equal to 2;
at least one organic solvent;
colloidal silica; and
optionally at least one additive.

2. The composition of claim 1 , wherein W 1 , W 2 are independently represented by the Formula (II):

wherein C j F 2j and C k F 2k are independently a linear or branched perfluoro-alkyl group;
j is an integer from 1 to 10;
k is an integer from 1 to 10; and
m, n, o, p, q, r, s are each independently an integer from 0 to 100.

3. The composition of claim 1 , wherein c is an integer from 1 to 1000 and W 1 , W 2 are selected from the groups represented by Formula (III) and Formula (IV):

wherein x, y, z are each independently an integer from 1 to 100 and W 1 and W 2 are not represented by the same Formula (III) and Formula (IV).

4. The composition of claim 1 , wherein the organic solvent includes at least one non-fluorine-containing solvent selected from group consisting of: isopropyl alcohol, ethanol, methanol, acetone, tetrahydrofuran, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, and dipropylene glycol monomethyl ether.

5. The composition of claim 1 , wherein the organic solvent includes at least one fluorine-containing solvent selected from the group consisting of: ethyl nonafluorobutyl ether, methyl nonafluorobutyl ether, 1,1,1,3,3-pentafluorobutane, tetrafluoro-1-propanol, octafluoropentanol, trifluoroacetic acid, decafluoropentane, and ethoxynonafluorobutane.

6. The composition of claim 1 , comprising at least one additive selected from the group consisting of: water, a crosslinker, a catalyst, nanosize particles, a surfactant, and a lubricant.

7. The composition of claim 6 , wherein the crosslinker is selected from the group consisting of polyphosphazene, glycoluril, melamine, benzoguanamine, urea, and combinations thereof; wherein the catalyst is selected from the group consisting of acid catalysts, alkaline catalysts, metal-organic catalysts, tetraalkylammonium salt catalyst, and combinations thereof wherein the lubricant is selected from perfluroropolyether, silicon and combinations thereof and wherein the nanosize particles are selected from the group consisting of nanosize organic particles, nanosize inorganic particles, and combinations thereof.

8. The composition of claim 7 , wherein the nanosize organic particles are selected from the group consisting of polyethylene (PE) nanoparticles, polychlorotrifluoroethylene (PCTFE) nanoparticles, polytetrafluoroethylene (PTFE), nanoparticles, and combinations, thereof and wherein the nanosize inorganic particles are selected from the group consisting of silica, alumina, titania, zirconia, colloidal silica, silicon nitride, boron nitride, and combinations thereof.

9. The composition of claim 1 , further including at least one perfluoropolyether lubricant.

10. A composition for forming a poly fluorine-containing siloxane coating comprising:
a polymer of Formula (I):

wherein:

R is a hydrogen atom, an alkyl or aryl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl or aryl group having 1 to 10 carbon atoms;
Rf is a linear or branched perfluoro-alkyl group represented by the formula F—(C g F 2g )—, where g is an integer from 1 to 10;
W 1 , W 2 are each independently a perfluoroether-containing organic group;
Q 1 , Q 2 , Q 3 , Q 4 are each independently an organic linking group linking a Si element to a fluorinated group; and
a, d, e are each independently an integer from 0 to 1000, b, c are each independently an integer from 1 to 1000;
at least one organic solvent; and
optionally at least one additive.

11. The composition of claim 10 , wherein Q 1 , Q 2 , Q 3 , Q 4 are independently represented by an isolated repeated formula selected from the group consisting of:
—CH 2 —,
—OCONH—, —COO—, —CONH—, 13 CH 2 O—, —CH(CH 3 )—, —C(CH 3 ) 2 —, and —(Si(CH 3 ) 2 O) h —Si(CH 3 ) 2 —, wherein h is independently an integer from 0 to 10 for each of Q 1 , Q 2 , Q 3 , Q 4 ; and wherein each R is independently selected from the group consisting of H, CH 3 , and CHF 2 .

12. The composition of claim 10 , wherein W 1 , W 2 are independently represented by the Formula (II):

wherein C j F 2j and C k F 2k are independently a linear or branched perfluoro-alkyl group;
j is an integer from 1 to 10;
k is an integer from 1 to 10; and
m, n, o, p, q, r, s are each independently an integer from 0 to 100.

13. The composition of claim 10 , wherein W 1 , W 2 are independently selected from the groups represented by Formula (III) and Formula (IV):

wherein x, y, z are each independently an integer from 1 to 100.

14. The composition of claim 10 , wherein the organic solvent includes at least one non-fluorine-containing solvent selected from group consisting of: isopropyl alcohol, ethanol, methanol, acetone, tetrahydrofuran, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, and dipropylene glycol monomethyl ether.

15. The composition of claim 10 , wherein the organic solvent includes at least one fluorine-containing solvent selected from the group consisting of: ethyl nonafluorobutyl ether, methyl nonafluorobutyl ether, 1,1,1,3,3-pentafluorobutane, tetrafluoro-1-propanol, octafluoropentanol, trifluoroacetic acid, decafluoropentane, and ethoxynonafluorobutane.

16. The composition of claim 10 , comprising at least one additive selected from the group consisting of: water, a crosslinker, a catalyst, nanosize particles, a surfactant, and a lubricant.

17. The composition of claim 16 , wherein the crosslinker is selected from the g

Assignees

• Honeywell Int Inc

Inventors

• Liu Ya Qun
• Zhang Bright
• Duan Huifeng
• Jiang Wanchao
• Jiang Yunzi
• Ding Zhe
• Chen David K
• Shen Yanming
• Wang Wei Jun

Classifications

• C08K2003/2227

  of aluminium · CPC title

• C08G77/24

  halogen-containing groups · CPC title

• C08K2003/2241

  Titanium dioxide · CPC title

• C09D183/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08K2003/2244

  of zirconium · CPC title