Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic sulfur compound – wherein the sulfur is single bonded...
Reexamination Certificate
2001-06-29
2002-08-20
Howard, Jacqueline V. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Organic sulfur compound, wherein the sulfur is single bonded...
C508S403000, C508S410000, C508S418000
Reexamination Certificate
active
06436882
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to functional fluid compositions that contain selected compounds derived from alkylnaphthalenesulfonic acids. In particular, this invention relates to functional fluid compositions that contain selected salts and esters derived from mono-, di-, and/or poly-alkyl substituted naphthalenesulfonic acids. These sulfonic acid derivatives impart corrosion-inhibiting, rust-inhibiting, friction-modifying, oxidation-inhibiting, and antiwear properties to functional fluids.
2. Brief Description of Art
Various derivatives of alkylated benzenesulfonic and naphthalenesulfonic acid compositions have been used as corrosion inhibitors, rust inhibitors and wear control agents for a wide variety of functional fluids, including lubricants and hydraulic fluids. Such derivatives include neutral metal salts, basic metal salts, and amine salts derived from alkylated benzenesulfonic and naphthalenesulfonic acids.
These derivatives have been prepared by first alkylating benzene, naphthalene or alkylnaphthalene with a suitable alkylating agent in the presence of a catalyst. The most common alkylation method is the Friedel-Crafts method employing alkyl halides, alcohols or olefins. The Friedel-Crafts method for the alkylation of benzene and naphthalene with alkyl halides, alcohols, or olefins to produce the corresponding alkylated products has been extensively described in the literature and reviewed, e.g., by C. C. Price in “Organic Reactions”, Volume 3, Chapter 1, pages 1-82, John Wiley & Sons, Inc., 1946. The alkylation reaction, catalyzed by materials such as aluminum chloride, antimony pentachloride, ferric chloride, stannic chloride, zinc chloride, hydrogen fluoride, sulfuric acid, and phosphoric acid, must be carefully controlled to achieve the degree of alkylation required and to control the formation of poly-alkylation and rearrangement products (C. C. Price, supra). Rearrangement of the alkyl group can occur during the Friedel-Crafts alkylation reaction, so that one obtains a mixture of linear and branched alkyl-substituted aromatic compounds even when starting alkylating agents are linear. The position of substitution of the alkyl groups on the aromatic ring is dependent on the alkylating agent, reaction conditions, and type of catalyst utilized.
Another known method of alkylating benzene or naphthalene or alkylnaphthalenes to produce a composition substituted with linear alkyl groups is the two step synthesis that includes: (1) Friedel-Crafts acylation of benzene or naphthalene with an acyl halide, such as RCOCl (where R is a linear alkyl group), to form an acylated product, followed by (2) Clemmenson reduction or Wolff-Kirshner reduction of the carbonyl group. These reactions are well known in the literature and are discussed in textbooks, such as that by R. T. Morrison and R. N. Boyd entitled “Organic Chemistry,” Third Edition, Chapters 12, 19, and 30, Allyn and Bacon, Inc., 1973.
The preferred commercial method of making polyalkylnaphthalenes has been the alkylation of naphthalene with propylene or butylene trimers or tetramers in the presence of a catalyst. This reaction is described in detail in U.S. Pat. No. 2,764,548 (King and Thielcke). The resulting alkylnaphthalenes have highly branched polypropylene or polybutylene chains (C
9
, C
12
or C
16
in length).
U.S. Pat. Nos. 5,401,896 and 6,071,864 teach the alkylation of naphthalene and alkylnaphthalenes with alkylation agents in the presence of zeolites. These patents do not teach or suggest making of the sulfonic acids or their derivatives from the resulting alkylnaphthalenes.
In the case of known commercial functional fluids that contain alkylated naphthalenesulfonic acid derivatives, the alkyl chains are derived from propylene or butylene trimers or tetramers. While such existing functional fluids are suitable for a wide variety of applications, it has now been discovered that if each of the alkyl chains in these derivatives is essentially linear while being at least 10 carbon atoms (C
10
) in length, significant improvements in corrosion inhibition, demulsibility, and wet filterability may be achieved. Two tests that are commonly used to assess wet filterability are the Wet AFNOR Filtration Test and the Wet Pall Test. The wet tests differ from the dry tests in that the wet tests contain a recommended amount of water. Accordingly, the present invention is based on these discoveries.
BRIEF SUMMARY OF THE INVENTION
Therefore, one aspect of the present invention is directed to a functional fluid composition comprising a mixture of:
(a) at least one functional fluid base component; and
(b) an additive package comprising at least one derivative of a mono-, di-, or poly-alkylated naphthalenesulfonic acid selected from the group consisting of:
(i) neutral metal salts of said mono-, di-, and poly-alkylated naphthalenesulfonic acids;
(ii) basic metal salts of said mono-, di-, and poly-alkylated naphthalenesulfonic acids;
(iii) amine salts of said mono-, di-, and poly-alkylated naphthalenesulfonic acids; and
(iv) esters of said mono-, di-, and poly-alkylated naphthalenesulfonic acids;
wherein the mono-, di-, and poly-alkylated naphthalenesulfonic acids are represented by formula (I):
wherein R
1
, R
2
, R
3
and R
4
are individually selected from the group consisting of hydrogen or essentially linear hydrocarbyl groups having about 10 to about 14 carbon atoms; and wherein l, m, n and p are integers from 0 to 4 and the sum of l+m+n+p is at least 1; and wherein R
1
, R
2
, R
3
, or R
4
, is a hydrogen where either l, m, n or p is 0.
Another aspect of the present invention is directed to a hydraulic fluid which is dispersant-free and contains (a) at least one hydraulic fluid base component; and (b) an additive package as defined above.
A preferred aspect of the present invention is directed to a functional fluid composition comprising a mixture of:
(a) at least one functional fluid base component; and
(b) an additive package comprising at least one neutral or basic calcium salt of a mono-, di-, or poly-alkylated naphthalenesulfonic acid as defined above, preferably in an effective rust-inhibiting amount.
The incorporation of these particular alkylnaphthalenesulfonic acid derived compositions into the functional fluid formulations of the present invention provides several advantages over the commercially known functional fluids described above. Specifically, the functional fluids of the present invention have excellent rust- and corrosion-inhibiting properties and improved demulsibility, while maintaining the better hydrolytic stability, thermal stability, and antiwear performance of the functional fluids described above. In addition, these additives impart oxidation-inhibiting, friction-modifying, and antiwear properties to certain types of functional fluids. Specifically for hydraulic fluids, the present sulfonic acid derivatives have the advantages of providing a combination of good demulsibility, rust performance and the wet filterability performance, as assessed by the AFNOR and the Pall Tests. Passing this combination of tests is a common problem with the corresponding branched-chain type alkylarylsulfonic acid derivatives as well as with linear-chain type alkyl benzene sulfonic acid derivatives. Many suppliers of commercial hydraulic fluids add dispersants to hydraulic fluid formulations to overcome wet filtration problems. See U.S. Pat. No. 5,767,045, which provides an example of using this type of strategy. The present invention has the special advantage of not requiring the use of the additional dispersant to achieve good wet AFNOR performance for certain hydraulic fluid formulations.
DETAILED DESCRIPTION OF THE INVENTION
Throughout this specification and claims, all parts and percentages are by weight, temperatures are in degrees Celsius, and pressures are at or near atmospheric unless otherwise clearly indicated.
As used in this specification and in the appended claims, the terms “hydrocarbyl” and “hydrocarbylene” denote a group havin
Howard Jacqueline V.
King Industries, Inc.
Simons William A.
Wiggin & Dana
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