Ice release coatings

• US 10,221,333 B2
• Filed: 09/30/2014
• Issued: 03/05/2019
• Est. Priority Date: 09/30/2013
• Status: Active Grant

• Current Assignee: Virginia Commonwealth University
• Original Assignee: Virginia Commonwealth University
• Inventors: Wynne, Kenneth J., Zhang, Wei
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US15/025,888
• Publication Number:
  US 20160215167A1
• Time in Patent Office: 1,617 Days
• Field of Search: 428447, 4284231, 428 28
• CPC Class Codes: C08G 18/246 containing also tin-carbon bonds
• CPC Class Codes: C08G 18/3893 containing silicon
• CPC Class Codes: C08G 18/40 High-molecular-weight compounds C08G18/2805 takes precedence
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/4854 Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
• CPC Class Codes: C08G 18/6204 Polymers of olefins unsaturated polymers of conjugated dienes C08G18/69
• CPC Class Codes: C08G 18/69 Polymers of conjugated dienes hydrogenated polymers of conjugated dienes C08G18/6208
• CPC Class Codes: C08G 18/718 containing silicon
• CPC Class Codes: C08G 18/837 by silicon containing compounds
• CPC Class Codes: C08G 65/336 containing silicon
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/54 Nitrogen-containing linkages C08G77/485 takes precedence
• CPC Class Codes: C08K 5/5465 containing at least one C=N bond
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• CPC Class Codes: C09D 171/02 Polyalkylene oxides
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 175/08 : from polyethers
• CPC Class Codes: C09D 183/14 : in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence
• CPC Class Codes: C09K 3/18 : for application to surfaces to minimize adherence of ice, mist or water thereto rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30; Thawing or antifreeze materials for application to surfaces used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00

Abstract

A compound is provided, having the formula (I), wherein R_s is a soft block polymer; wherein each T is independently a urethane or urea linkage; see formulae (A) and (B); wherein each R_D is independently —CH₃, —CH₂CH₃, —CH₂CH₂CH₃, or —CH₂CH₂CH₂CH₃; wherein each R′_D is independently —CH₃, —CH₂CH₃, —CH₂CH₂CH₃, —CH₂CH₂CH₂CH₃, or —OR_D; and wherein each p is independently 1, 2, or 3. Compositions containing the compound, and methods of making and using the compound are provided.

Claims

1. A composition, comprising a mixture of:

1) a composition, comprising a reaction product of;

(A) one or more compounds having the following formula (I);

(B) one or more alkoxysilane, alkoxysiloxane, or combination thereof as mesosurface builder;

(C) optionally, one or more polydialkylsiloxane diol as first nanosurface modifier;

(D) optionally, one or more fluorinated alkoxysilane as second nanosurface modifier;

(E) optionally, one or more of a catalyst, water, or combination thereof;

(F) optionally, one or more solvent; and

(G) optionally, one or more thermoplastic polyurethane; and

2) one or more thermoplastic polyurethane;

wherein formula (I) is;

2. The composition of claim 1, wherein the mixture comprises:

20-80 wt % of the composition of

     1); and

80-20 wt % of the thermoplastic polyurethane

     2).

3. The composition of claim 1, wherein the mixture is optically transparent.

4. A surface coating, comprising the composition of claim 1.

5. An article, having a surface in contact with the composition of claim 1.

6. The composition of claim 1, wherein the soft block polymer R_S is a linear homopolymer or copolymer.

7. The composition of claim 1, wherein each R′

_D is independently —

CH₃, —

OCH₃, or —

OCH₂CH₃.

8. The composition of claim 1, wherein (A) comprises two or more different compounds of having formula (I), wherein a first soft block polymer R_S in one compound having formula (I) has a molecular weight, M_w, of 200-1,000 Da, and a second soft block polymer R_S in a different compound having formula (I) has a molecular weight, M_w, of 1,500-3,000 Da.

9. The composition of claim 1, wherein mesosurface builder (B) is one or more of poly(diethoxysiloxane) (PDEOS), poly(dimethoxysiloxane) (PDMOS), 1,2-bis(triethoxysilyl)ethane (BTESE), 1,4-bis(triethoxysilyl)benzene 1,2-bis(triethoxysilyl)ethylene, bis(triethoxysilyl)methane, 1,8-bis(triethoxysilyl)octane, 1,10-bis(trimethoxysilyl)decane, 1,6-bis(trimethoxysilyl)-2,5-dimethylhexane, 1,2-bis(trimethoxysilyl)ethane, bis(trimethoxysilylethyl)benzene, 1,6-bis(trimethoxysilyl)hexane, 1,4-bis(trimethoxysilylmethyl)benzene, 1,8-bis(trimethoxysilyl)octane, or combination thereof.

10. The composition of claim 1, wherein the first nanosurface modifier (C) is polydimethylsiloxane diol, polydiethylsiloxane diol, or combination thereof.

11. The composition of claim 1, wherein the second nanosurface modifier (D) is poly[methyl(3,3,3-trifluoropropyl)siloxane] diol, pentafluorophenyltrimethoxysilane, 3-(heptafluoroisopropoxy)propyltrimethoxysilane, nonafluorohexyltriethoxysilane, nonafluorohexyltrimethoxysilane, pentafluorophenylpropyltrimethoxysilane, pentafluorophenyltriethoxysilane, bis(pentafluorophenyl)dimethoxysilane, (tridecafluoro-1,1,2,2-tetrahydrooctyl)triethoxysilane, (tridecafluoro-1,1,2,2-tetrahydrooctyl)trimethoxysilane, p-trifluoromethyltetrafluorophenyltriethoxysilane, (3,3,3-trifluoropropyl)methyldimethoxysilane, (3,3,3-trifluoropropyl)trimethoxysilane, or combination thereof.

12. The composition of claim 1, wherein (C) is present in an amount of about 0.004-20 wt % based on the weight of the composition.

13. The composition of claim 1, wherein (D) is present in an amount of about 0.004-20 wt % based on the weight of the composition.

14. A surface coating, comprising the composition of claim 1.

15. An article, having a surface in contact with the composition of claim 1.

16. The article of claim 15, which is a mat, tile, polyurethane, vinyl strip, or a combination thereof.