Fluroaliphatic dimer acid derivatives and use thereof

Details Fluroaliphatic dimer acid derivatives and use thereof Fluroaliphatic dimer acid derivatives and use thereof

1999-09-08

2001-01-09

Nakarani, D. S. (Department: 1773)

Fabric (woven, knitted, or nonwoven textile or cloth, etc.)

Coated or impregnated woven, knit, or nonwoven fabric which...

Coating or impregnation specified as water repellent

C106S002000, C252S008570, C252S008620, C427S393400, C428S151000, C428S537500, C428S540000, C442S079000, C442S088000, C442S092000

Reexamination Certificate

active

06171983

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to fluorochemical compositions comprising fluoroaliphatic dimer acid derivatives, their preparation, their use as water and oil repellents in treating substrates, such as leather, textiles and paper, and to the resulting treated substrates.
BACKGROUND OF THE INVENTION
It is common to treat the surfaces of leather, textiles, and other substrates to impart added desirable properties thereto, such as oil and water repellency and resistance to dry or oily soil. A number of fluorochemical compositions have been proposed for such treatment and several are commercially used for that purpose, such as those sold under the tradename “Scotchgard.” Various patents and publications disclose a variety of such compositions for various uses, e.g. U.S. Pat. Nos. 3,462,296 (Raynolds et al.), 3,484,281 (Guenthner et al.), 3,816,167 (Schultz et al.), 3,944,527 (McCown), 4,024,178 (Landucci), 4,190,545 (Marshall et al.), 4,215,205 (Landucci) and 4,426,476 (Chang), Japanese published patent application (Kokai) No. 81-49081, and Banks, R. E., Ed., “Organofluorine Chemicals and their Industrial Applications,” pages 226-230 (Ellis Harwood, Ltd., West Sussex, England, 1979). Also various patents disclose carpet treating compositions containing, inter alia, various fluorochemicals, e.g. U.S. Pat. Nos. 3,923,715 (Dettre et al.), 4,043,964 (Sherman et al.), 4,107,055 (Sukornick et al.), 4,264,484 (Patel), Re 30,337 (Loudas), 4,388,372 (Champaneria) and 4,325,857 (Champaneria). Also various patents and publications disclose the use of fluorochemical compositions on leather, e.g., U.S. Pat. Nos. 4,920,190 (Lina et al.), 4,782,175, (Wehowsky et al.), 4,778,915 (Lina et al), 4,539,006 (Langford), 3,923,715 (Dettre et al.), 4,709,074 (Bathelt et al.) and L. Schlösser “Eigenschaften fluororganischer Verbindungen und ihre Anwendung auf dem Ledergebiet,” DAS LEDER, 41 Jahrgang August 1990, pages 149-153.
U.S. Pat. No. 3,923,715 (Dettre et al.) describes an aqueous dispersion containing at least 5 weight percent of a perfluoroalkyl ester made from a fluorinated alcohol and a mono- or polycarboxylic acid which contains 3 to 30 carbon atoms. The dispersion is applied to textile fibers in order to insure dry soil resistance and non-flame propagating characteristics.
U.S. Pat. No. 4,426,476 (Chang et al.) relates to a textile treatment composition containing water-insoluble fluoroaliphatic radical and aliphatic chlorine-containing ester and water-insoluble fluoroaliphatic radical-containing polymer. The ester is prepared by reacting a fluoroaliphatic chlorine-containing alcohol with a mono or polycarboxylic acid. The mono or polycarboxylic acids include acids up to 18 carbon atoms e.g. decanoic acid, tridecanedioic acid, linoleic acid.
U.S. Pat. No. 4,539,006 (Langford) relates to a composition useful for treating leather, textiles and cellulosic materials to impart water- and oil-repellency thereto. The composition contains a fluorochemical compound having a fluoroaliphatic moiety, an aliphatic moiety and an organic group which connects the fluoroaliphatic moiety and the aliphatic moiety. The composition can be prepared by, inter alia, reacting a fluoroaliphatic alcohol with a fatty acid. Useful acids contain 5 to 36 carbon atoms. Representative examples of fatty acids are linseed fatty acid, linolenic acid, oleostearic acid, ricinoleic acid, oleic acid, linoleic acid, sorbic acid, and dimer acids. The fatty acids have at least one to three unsaturated sites, and more if available. In Example 11 of this patent, the dimer acids are reacted with a perfluoroaliphatic alcohol in a ratio of 0.5 equivalent dimer acid to 0.25 equivalent alcohol [thus, the acid is not fully esterified].
Although the above-mentioned fluorochemical compositions are useful to various degrees in treating various substrates such as textile, carpet, leather, and paper, and many are commercial products, some are ineffective under normal use conditions that impart abrasive wear to the treated substrate, some provide insufficient oil or water repellency on the treated substrates, and some require high (and therefore economically undesirable) application treatment rates to obtain sufficient oil or water repellency on the treated substrates. Some fluorochemical compositions have an adverse effect on the appearance and feel or “hand” of the treated substrates.
SUMMARY OF THE INVENTION
The present invention provides, in one aspect, a fluorochemical composition comprising a mixture of normally solid, fluorochemical compounds and/or polymers each compound having at least two fluoroaliphatic groups and a large (at least 30-carbon) hydrocarbon or aliphatic moiety and the polymers having at least one fluoroaliphatic group and a plurality of the large hydrocarbon moiety. Each said fluoroaliphatic group is connected, linked, or bonded to such a hydrocarbon moiety by an organic moiety. A preferred fluorochemical composition comprises a mixture of fluoroaliphatic esters of dimer acids.
Unless otherwise indicated herein, the term “dimer acids” is used herein in its common usage to mean polymerized fatty acids products of relatively high molecular weight made up of mixtures comprising various ratios of a variety of large or relatively high molecular weight substituted cyclohexenecarboxylic acids, predominately the 36-carbon dibasic acid (dimer acid) and the 54-carbon tribasic acid (trimer acid)—see Leonard, Edward C., “The Dimer Acids,” Humko Sheffield Chemical, Memphis, Tn., 1975, p. 1,4,5, and Kirk-Othmer, “Encyclopedia of Chemical Technology, John Wiley & Sons, Third Ed., Vol. 7, 1979, p. 768-770.
The fluorochemical composition of this invention has a low acid value or number (which can be measured by the method of AOCSTe 1A-64), e.g., less than about 10 or 20 and even essentially zero. Thus, in the case of the preferred fluorochemical composition comprising a mixture of fluoroaliphatic diesters and/or triesters of diner acids, such acids are essentially fully esterified and the resulting esters are thus carboxyl-free and neutral or essentially neutral, in contrast to half-esters which would be acidic due to the presence of non-esterified carboxyl functionality.
In another aspect, this invention provides processes for preparing the fluorochemical compositions by reacting diner acids with fluoroaliphatic alcohol or derivatives thereof or by reacting dimer diamines with fluoroaliphatic carboxylic acid or fluoroaliphatic alcohol derivatives. In some of these preparations, a third reactant is included, namely, polyisocyanate, polyamine, or polyol, the resulting reaction product comprising polymers having a plurality of the fluoroaliphatic groups and a plurality of the large hydrocarbon moieties. The preferred fluorochemical compositions can be prepared, for example, by fully esterifying dimer acids (such as those sold under the trademark “Pripol” which contain about 25 to 98 weight percent diner acid and the balance being trimer acid) with fluoroaliphatic alcohol (such as an N-alkyl perfluoroalkylsulfonamidoalkyl alcohol, sometimes named as an N-alkanol perfluoroalkanesulfonamide, e.g., C
8
F
17
SO
2
N(CH
3
)CH
2
CH
2
OH).
In another aspect of the invention, the fluorochemical compositions are used to impart a desirable combination of surface properties to various substrates, such as fibrous substrates, e.g, textiles, carpets, paper, and leather, and siliceous substrates, e.g., ceramic tile, concrete, stone, and masonry. Said surface properties include a high degree of oil and water repellency and retention of the oil and water repellency when the treated substrates are subjected to abrasion such as that encountered in the normal use of said substrates. These properties can be obtained by contacting the surfaces of the substrates with the fluorochemical composition at low application treatment rates, the fluorochemical compositions having minimal, if any, adverse effect on the appearance and feel or “hand” of the treated substrates. The fluorochemical compositions according to this invention can be applied as

Affiliated with

Also associated with

Rating

Fluroaliphatic dimer acid derivatives and use thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Fluroaliphatic dimer acid derivatives and use thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fluroaliphatic dimer acid derivatives and use thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2506284