IP Library Granted Patent US 8,092,736
Granted Patent B2
US 8,092,736 · App. 12/276,448 · Granted Jan 10, 2012

Fluorotelomer/silane compositions

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Quick Facts
Patent No.
US 8,092,736
App. No.
12/276,448
Granted
Jan 10, 2012
Kind
B2
Abstract

A composition and its use as a mold release composition are disclosed. The composition comprises a fluorotelomer, which comprises repeat units derived from a fluoroalkene, and optionally a comonomer, and has an endgroup derived from an alcohol, an alcohol derivative, or a combination thereof, and said fluorotelomer has or comprises a structure depicted as H(CX 2 ) p B q D r or a mixture of structures depicted as H(CX 2 ) p B q and H(CX 2 ) p D r , wherein each X is independently H or F, provided at least one X is F, p is a number from about 16 to about 1500, B represents a unit derived from a hydrofluorocarbon, q is a number from 0.02 to 0.4, D represents an endgroup derived from said alcohol, alcohol derivative, or combination thereof, and r is a number 0.2 to 1.0. The composition comprises a silane having the formula R 1 n —Si—(Z) 4-n wherein Z is OR 2 , Cl, or H, wherein R 1 is selected from the group consisting of hydrogen, a hydrocarbon radical having 1-34 carbon atoms, and combinations of two or more thereof, R 2 is selected from the group consisting hydrogen, a hydrocarbon radical having 1-4 carbon atoms, and combinations of two or more thereof, provided that R 1 and R 2 both cannot be hydrogen, and n is a number from 1 to 3. The composition may further comprise a solvent and/or a catalyst.

Claims (17)

1. A release agent composition comprising (a) a fluorotelomer, (b) a silane, and (c) a solvent, wherein said fluorotelomer comprises repeat units derived from a fluoroalkene, and optionally a comonomer, and has an endgroup derived from an alcohol, an alcohol derivative, or a combination thereof, and said fluorotelomer has or comprises a structure depicted as H(CX 2 ) p B q D r or a mixture of structures depicted as H(CX 2 ) p B q and H(CX 2 ) p D r , wherein each X is independently H or F, provided at least one X is F, p is a number from about 16 to about 1500, B represents a unit derived from a hydrofluorocarbon, q is a number from 0.02 to 0.4, D represents an endgroup derived from said alcohol, alcohol derivative, or combination thereof, and r is a number 0.2 to 1.0; and wherein said silane has the formula R 1 n —Si—(Z) 4-n wherein Z is OR 2 , Cl, or H, wherein R 1 is selected from the group consisting of hydrogen, a hydrocarbon radical having 1-34 carbon atoms, and combinations of two or more thereof, R 2 is selected from the group consisting hydrogen, a hydrocarbon radical having 1-4 carbon atoms, and combinations of two or more thereof, provided that R 1 and R 2 both cannot be hydrogen, and n is a number from 1 to 3.

2. The composition of claim 1 wherein the fluoroalkene has 2 to about 10 carbon atoms.

3. The composition of claim 2 wherein the fluoroalkene is selected from the group consisting of 1,1-difluoroethylene, 1,2-difluoroethylene, tetrafluoroethylene (TFE), 3,3,3-trifluoropropene, and hexafluoropropylene (HFP).

4. The composition of claim 3 wherein the fluoroalkene is tetrafluoroethylene.

5. The composition of claim 1 wherein the alcohol or alcohol derivative has from 4 to about 12 carbon atoms.

6. The composition of claim 1 wherein the alcohol or alcohol derivative is selected from the group consisting of 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, 1-hexanol, 2-hexanol, 1-heptanol, 2-heptanol, sec-butyl acetate, cyclohexanol, 1-methoxy-2-propanol, 1-methoxy-3-butanol, 1-methoxy-2-pentanol, 1-methoxy-2-propanol acetate ester, 2-methyl-2-butanol, and combinations of two or more thereof.

7. The composition of claim 1 wherein R 1 is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, vinyl, allyl, phenyl, and combination of two or more thereof.

8. The composition of claim 1 wherein R 2 is selected from the group consisting of methyl, ethyl, propyl, butyl, iso-propyl, iso-butyl, or a combination of two or more thereof.

9. The composition of claim 1 wherein the silane is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, vinyltrimethoxysilane, octyltrimethoxysilane, dimethyldichlorosilane, methyldichlorosilane, methyltrichlorosilane, phenyltricholorosilane, trichlorosilane, trimethylchlorosilane, silicone tetrachloride, vinyltrichlorosilane, and combinations of two or more thereof.

10. The composition of claim 1 wherein the solvent is selected from the group consisting of n-heptane, octane, nonane, isoparaffinic fluid, isopropanol, butanol, pentanol, or a combination of two or more thereof.

11. The composition of claim 10 further comprising a catalyst.

12. The composition of claim 11 wherein the catalyst is selected from the group consisting of zirconium acetate, zirconium propionate, zirconium butyrate, zirconium hexanoate, zirconium 2-ethylhexanoate, zirconium octoate, tetraethyl zirconate, tetrapropyl zirconate, tetraisopropyl zirconate, tetrabutyl zirconate, titanium acetate, titanium propionate, titanium butyrate, titanium hexanoate, titanium 2-ethylhexanoate, titanium octoate, tetraethyl titanate, tetrapropyl titanate, tetraisopropyl titanate, tetrabutyl titanate, titanium bis-ammonium lactate, bis-acetylacetonate titanate, bis-ethyl acetoacetate titanate, bis-triethanolamine titanate, and a combination of two or more thereof.

13. The composition of claim 12 wherein the composition comprises 1 to 10%, by weight of fluorotelomer, based on the total weight of the composition.

14. The composition of claim 13 wherein the composition comprises about 0.1 to about 10% by weight of silane, based on the total weight of the composition.

15. The composition of claim 14 , wherein the composition comprises about 70 to 98%, by weight, of the total composition.

16. The composition of claim 15 , wherein the composition comprises about 0.01 to about 1.0% by weight of catalyst, based on the total weight of the composition.

17. The composition of claim 16 wherein the fluoroalkene is tetrafluoroethylene, B is derived from a hydrofluorocarbon selected from the group consisting of 2,3-dihydrodecafluoropentane, perfluorobutyl methyl ether, perfluorobutyl ethyl ether, 2,4-dihydrooctafluorobutane, 1,1,2,3,3,3-hexafluoropropyl methy ether, 2-trifluoromethyl-2,3-dihydrononafluoropentane, 1,1,1,3,3-pentafluorobutane, and combinations thereof; the endgroup of the fluorotelomer is derived from an alcohol selected from the group consisting of 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, and a combination thereof, the silane is selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, vinyltrimethoxysilane, octyltrimethoxysilane, dimethyldichlorosilane, methyldichlorosilane, methyltrichlorosilane, phenyltricholorosilane, trichlorosilane, trimethylchlorosilane, silicone tetrachloride, vinyltrichlorosilane, and combinations of two or more thereof; the solvent is selected from the group consisting of n-heptane, octane, nonane, isoparaffinic fluid, isopropanol, butanol, pentanol, and a combination of two or more thereof; and the catalyst is selected from the group consisting of tetraethyl titanate, tetrapropyl titanate, tetraisopropyl titanate, tetrabutyl titanate, and a combination of two or more thereof.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2009
From: MOFFETT, ROBERT HARVEY
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 022159/0304 →