Fluorochemical benzotriazoles

Details Fluorochemical benzotriazoles Fluorochemical benzotriazoles

2000-09-20

2002-04-23

Thibodeau, Paul (Department: 1773)

Stock material or miscellaneous articles

Web or sheet containing structurally defined element or...

Physical dimension specified

C428S411100, C428S457000, C548S257000, C548S260000, C548S261000

Reexamination Certificate

active

06376065

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to fluorochemical benzotriazole compounds and uses thereof.
BACKGROUND OF THE INVENTION
Heretofore, there have been many ways to enhance the separation or release of one material from a surface of another material or substrate. For example, organic materials such as oils and waxes and silicones have been used as release agents to provide release characteristics to surfaces. One of the disadvantages of these release agents is that they usually need to be frequently re-applied to the surface so as to provide adequate release properties. Polymeric release coatings such as those made from polytetrafluoroethylenes have addressed some of the shortcomings of oils, waxes, silicones and other temporary coatings and are often more durable. Typically however, polymeric release coatings require a thicker coating than the non-durable treatments, they can be subject to thickness variations, and can present application difficulties.
SUMMARY OF THE INVENTION
The invention provides fluorochemical benzotriazoles that chemically bond to metal and metalloid surfaces and provide, for example, release and/or corrosion inhibiting characteristics to those surfaces. The compounds of the invention are characterized as having a head group which bonds to a metallic or metalloid surface and a tail portion which is suitably different in polarity and/or functionality from a material to be released. The compounds of the invention when applied to a metallic or metalloid surface form durable, self-assembled films that are monolayers or substantially monolayers. Fluorochemical benzotriazoles of the invention include those having the formula:
wherein R
f
is C
n
F
2n+1
—(CH
2
)
m
, wherein n is an integer from 1 to 22 and m is 0, or an integer from 1 to 3; X is —CO
2
—, —SO
3
—, —CONH—, —O—, —S—, a covalent bond, —SO
2
NR—, or —NR—, wherein R is H or C
1
to C
5
alkylene; Y is —CH
2
— wherein z is 0 or 1; and R
1
is H, lower alkyl or R
f
—X—Y
z
— with the provisos that when X is —S—, or —O—, m is 0, and z is 0, n is ≧7 and when X is a covalent bond, m or z is at least 1. Preferably n+m is equal to an integer from 8 to 20.
This invention further provides compositions comprising one or more of the fluorochemical benzotriazoles.
This invention also provides a method of treating a metallic or a metalloid surface with a compound of the invention comprising the step of contacting a composition comprising a fluorochemical benzotriazole of the invention to the metallic or metalloid surface. An ultra-thin film can be formed on a surface by contacting the surface with a fluorochemical benzotriazole in liquid or vapor form.
This invention also provides fluorochemical benzotriazole compositions for use as release agents comprising one or more compounds having the formula:
wherein R
f
is C
n
F
2n+1
—(CH
2
)
m
—, wherein n is 1 to 22, m is 0 or an integer from 1 to 3; X is —CO
2
—, —SO
3
—, —S—, —O—, —CONH—, a covalent bond, —SO
2
NR—, or —NR—, wherein R is H or C
1
to C
5
alkylene, and q is 0 or 1; Y is C
1
-C
4
alkylene, and z is 0 or 1; and R
1
is H, lower alkyl, or R
f
—X—Y
z
.
Some of the advantages of the compounds of the invention include: application of the compounds of the invention to a surface is relatively fast and simple which minimizes cost and environmental impact; dense films or layers can be formed using very small amounts of the compound; compounds of the invention self-assemble into protective layers; and the protective layers can be very durable depending upon the surface type and compound used.


REFERENCES:
patent: 3082088 (1963-03-01), Heilmann et al.
patent: 4187186 (1980-02-01), Braid
patent: 4788292 (1988-11-01), Clark et al.
patent: 5504214 (1996-04-01), Marhold et al.

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