Substrate coating compositions and methods

Patent metadata

Field	Value
Publication number	US-2024343925-A1
Application number	US-202418656477-A
Country	US
Kind code	A1
Filing date	May 6, 2024
Priority date	Jul 17, 2013
Publication date	Oct 17, 2024
Grant date	—

Abstract

A coating composition comprising: (a) at least one coating agent comprising a perfluoropolyether-modified alkyloxysilane polymer; and (b) a carrier composition comprising monochloro, trifluoropropene, wherein the carrier is present in an amount effective to at least partially solvate or at least partially emulsify the coating agent. Such compositions may optionally contain one or more other co-carriers or additives. Also disclosed are methods of coating substrates, in particular substrates having a hard surface such as ceramics or glass, to render them water, oil and/or dirt repellent.

First claim

What is claimed is:

1 . A coating composition for forming a water repellant coating on a substrate comprising:
(a) at least one coating agent comprising at least one perfluoropolyether-modified alkyloxysilane polymer; and (b) a carrier comprising at least about 70% by weight of trans-1-chloro-3,3,3-trifluoropropene (trans-HCFO-1233zd) and being effective to at least partially solvate or at least partially emulsify the coating agent.

2 . The composition of claim 1 , wherein said perfluoropolyether-modified alkyloxy silane comprises a compound of formula I, formula II, or formula III:
R 1 f —Si(R) a (X) 3−a   (I)
Si(R) a (X) 3−a —R 2 f —Si(R) a (X) 3−a   (II)
R 1 f —Si(R) z (X) 2−a —O—Si(R 1 f )(R) a (X) 1−a —O—Si(R) a (X) 2−a —R 1 f   (III)

wherein
R is a monovalent alkyl or aryl radical;
X is a hydrolyzable radical;
a is an integer of 0 to 2;
R 1 f is F—(CF 2 ) l —R f —(CH 2 ) m Y(CH 2 ) n —; and
R 2 f is —(CH 2 ) n Y(CH 2 ) m —R f —(CH 2 ) m Y(CH 2 ) n —;
wherein
l is an integer from 1 to 6;
m is 1 or 2;
n is an integer from 2 to 20;
Y is O or a bivalent organic group; and
R f is a perfluoropolyether group comprising perfluorinated repeating units selected from the group consisting of —(OC 3 F 6 ) x —, —(OC 2 F 4 ) y —, —(OCF 2 ) z , or combination thereof, wherein x, y, and z are each independently an integer from 1 to 200.

3 . The composition of claim 1 further comprising a co-carrier selected from the group consisting of fluorocarbon co-carriers and non-fluorous co-carriers.

4 . The composition of claim 3 comprising a fluorocarbon co-carrier selected from the group consisting of perfluorocarbons, hydrofluorocarbons, fluorochlorocarbons, fluoroethers, fluoroketones, and combinations of two or more of these.

5 . The composition of claim 3 comprising a non-fluorous co-carrier selected from the group alcohols, ketones, esters, ethers, hydrocarbons, and combinations of two or more of these.

6 . The composition of claim 3 comprising a co-carrier selected from the group consisting of 1,1,1,3,3-pentafluorobutane, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorobutyl ether, perfluoroisobutyl ether, 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, methanol, ethanol, acetone, ethyl acetate, hexane, heptane, toluene, xylene, methylcyclohexane, chloroform, cyclohexane, 2,2-dichloropropane, methylene chloride, d-limonene, isoprene, styrene liquid, diisobutyl ketone, diisopropylketone, methyl isobutyl ketone, methyl isopropyl ketone, methyl cyclohexanone, cyclohexanone, isobutyl acetate, isopropyl acetate, butyl acetate, propyl acetate, ethyl acetate, diethyl ether, dimethyl ether, diethylene glycol, 2-ethylhexanol, and combinations of two or more of these.

7 . A sprayable composition comprising the composition of claim 1 .

8 . The sprayable composition of claim 7 , wherein said carrier consists essentially of trans-1-chloro-3,3,3-trifluoropropene (trans-HCFO-1233zd).

9 . The sprayable composition of claim 7 , wherein said perfluoropolyether-modified alkyloxysilane comprises a compound of formula I, formula II, or formula III:
R 1 f —Si(R) a (X) 3−a   (I)
Si(R) a (X) 3−a —R 2 f —Si(R) a (X) 3−a   (II)
R 1 f —Si(R) z (X) 2−a —O—Si(R 1 f )(R) a (X) 1−a —O—Si(R) a (X) 2−a —R 1 f   (III)

wherein
R is a monovalent alkyl or aryl radical;
X is a hydrolyzable radical;
a is an integer of 0 to 2;
R 1 f is F—(CF 2 ) l —R f —(CH 2 ) m Y(CH 2 ) n —; and
R 2 f is —(CH 2 ) n Y(CH 2 ) m —R f —(CH 2 ) m Y(CH 2 ) n —;
wherein
l is an integer from 1 to 6;
m is 1 or 2;
n is an integer from 2 to 20;
Y is O or a bivalent organic group; and
R f is a perfluoropolyether group comprising perfluorinated repeating units selected from the group consisting of —(OC 3 F 6 ) x —, —(OC 2 F 4 ) y —, —(OCF 2 ) z —, or combination thereof, wherein x, y, and z are each independently an integer from 1 to 200.

10 . A method for applying a coating agent to the surface of a substrate to form a water repellant coating on the substrate comprising:
(a) providing a composition comprising (i) at least one coating agent, and (ii) a carrier in an amount effective to at least partially solvate or at least partially emulsify the coating agent, said coating agent comprising at least one perfluoropolyether-modified alkyloxysilane, and said carrier comprising at least about 70% by weight of trans-1-chloro-3,3,3-trifluoropropene (trans-HCFO-1233zd); (b) applying the composition to the surface of a substrate; and (c) removing the carrier from the coating agent to form a coating having a water repellency as measured by a water contact angle of greater than about 105°.

11 . The method of claim 10 , wherein said carrier comprises at least about 90% by weight of trans-1-chloro-3,3,3-trifluoropropene (transHCFO-1233zd).

12 . The method of claim 11 , wherein said carrier consists essentially of trans-1-chloro-3,3,3-trifluoropropene (trans-HCFO-1233zd).

13 . The method of claim 10 , wherein said perfluoropolyether-modified alkyloxysilane comprises a compound of formula I, formula II, or formula III:
R 1 f —Si(R) a (X) 3−a   (I)
Si(R) a (X) 3−a —R 2 f —Si(R) a (X) 3−a   (II)
R 1 f —Si(R) z (X) 2−a —O—Si(R 1 f )(R) a (X) 1−a —O—Si(R) a (X) 2−a —R 1 f   (III)

wherein
R is a monovalent alkyl or aryl radical;
X is a hydrolyzable radical;
a is an integer of 0 to 2;
R 1 f is F—(CF 2 ) l —R f —(CH 2 ) m Y(CH 2 ) n —; and
R 2 f is —(CH 2 ) n Y(CH 2 ) m —R f —(CH 2 ) m Y(CH 2 ) n —;
wherein
l is an integer from 1 to 6;
m is 1 or 2;
n is an integer from 2 to 20;
Y is O or a bivalent organic group; and
R f is a perfluoropolyether group comprising perfluorinated repeating units selected from the group consisting of —(OC 3 F 6 ) x —, —(OC 2 F 4 ) y —, —(OCF 2 ) z , or combination thereof, wherein x, y, and z are each independently an integer from 1 to 200.

14 . The method of claim 10 , wherein the carrier is removed by evaporation.

15 . The method of claim 10 , wherein the applying step is selected from the group consisting of spray coating, dip coating, spin coating, pouring, brush coating, and immersing.

16 . The method of claim 10 , wherein the applying step is selected from the group consisting of spray coating, dip coating, spin coating and immersing.

17 . The method of claim 1 , wherein said carrier comprises at least about 90% by weight of trans-chloro-3,3,3-trifluoropropene (transHCFO-1233zd).

Assignees

• Honeywell Int Inc

Inventors

• Liu Jun
• Hu Johnny
• Shen Yanming
• Liu Ya Qun
• Hulse Ryan

Classifications

• C09D171/00

  Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06); Coating compositions based on derivatives of such polymers · CPC title

• C09D5/1662

  Synthetic film-forming substance · CPC title

• C09D5/1687

  Use of special additives · CPC title

• C08G65/336

  containing silicon · CPC title

• C09D171/02

  Polyalkylene oxides · CPC title