Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2000-11-03
2003-09-09
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S327400, C525S327700, C525S285000, C508S192000
Reexamination Certificate
active
06617396
ABSTRACT:
The present invention relates to an improved process for making a copolymer of a polybutene with an unsaturated acidic reagent.
BACKGROUND OF THE INVENTION
Copolymers prepared from polyisobutene and maleic anhydride are known. These copolymers are sometimes referred to as “polyPIBSA”. They can be prepared by copolymerizing a polybutene containing a high concentration of the methylvinylidene isomer (along with other polybutene isomers) with an unsaturated acidic reagent such as maleic anhydride using a free radical initiator. Apparently, only the methylvinylidene isomer reacts. If the polybutene contains, e.g., 70 mole percent methylvinylidene isomer, then only 70% conversion to copolymer can be achieved. This results in a less than optimum use of the polybutene starting material.
In order to improve the conversion of the polybutene starting material and improve raw material utilization, it has been found that if the polyPIBSA reaction mixture is further reacted with the unsaturated acidic reagent in the presence of a strong acid catalyst, such as a sulfonic acid catalyst, the unreacted polybutene can be converted to polyisobutenyl succinic anhydride. Up to 90-95% conversion of the starting polybutene can be achieved in this way. The resulting product is a mixture of polyPIBSA and acid-catalyzed thermal PIBSA.
The resulting mixture of polyPIBSA and acid-catalyzed thermal PIBSA can then be reacted with amines to form succinimides which can be post-treated with ethylene carbonate, boric acid and the like. These products are excellent ashless dispersants for lubricants with outstanding deposit inhibiting properties, and excellent soot thickening properties, and are also useful as fuel additives and as emulsifiers in explosive emulsions.
Water-in-oil explosive emulsions typically comprise a continuous organic phase (e.g., a carbonaceous fuel) and a discontinuous aqueous phase containing an oxygen supplying component (e.g., ammonium nitrate). Examples of such water-in-oil explosive emulsions are disclosed in U.S. Pat. Nos. 3,447,978; 3,765,964; 3,985,593; 4,008,110; 4,097,316; 4,104,092; 4,218,272; 4,259,977; 4,357,184; 4,371,408; 4,391,659; 4,404,050; 4,409,044; 4,448,619; 4,453,989; and 4,534,809, each of which is incorporated by reference herein.
U.S. Pat. No. 5,920,031, issued Jul. 6, 1999 to Jahnke, discloses water-in-oil emulsions that are useful as explosives. The emulsions comprise a discontinuous aqueous phase comprising at least one oxygen-supplying component, a continuous organic phase comprising at least one carbonaceous fuel, and a minor emulsifying amount of at least one emulsifier. The emulsifier is the product made by the reaction of component (A) with component (B), component (A) being at least one substituted succinic acylating agent, said substituted succinic acylating agent consisting of substituent groups and succinic groups wherein the substituent groups are derived from a polyalkene, said acylating agents being characterized by the presence within their structure of an average of at least 1.3 succinic groups for each equivalent weight of substituent groups, and component (B) being ammonia and/or at least one mono-amine.
SUMMARY OF THE INVENTION
The present invention provides a process for preparing a mixture of (1) a copolymer of a polyalkene and an unsaturated acidic reagent and (2) a polyalkenyl derivative of an unsaturated acidic reagent, said process comprising:
(a) copolymerizing (1) a polyalkene containing alkylvinylidene isomer and non-alkylvinylidene isomers and (2) an unsaturated acidic reagent under polymerization conditions in the presence of a free radical initiator; and
(b) reacting the product of step (a) with an unsaturated acidic reagent at elevated temperature in the presence of a strong acid.
Preferably, the polyalkene is a polybutene. More preferably, the polybutene is a polyisobutene, most preferably wherein at least 50% of said polyisobutene has methylvinylidene end groups. Preferably, the polyalkene has a Mn of from 500 to 2500.
Preferably, the unsaturated acidic reagent is maleic anhydride.
Preferably, the mole ratio of unsaturated acidic reagent to polyalkene is at least 1.0:1.
Preferably, the strong acid is an oil-soluble, strong organic acid, having a pK
a
of less than about 4. More preferably, it is a sulfonic acid, such as an alkyl benzene sulfonic acid, wherein the alkyl group has from 4 to 30 carbon atoms. Preferably, the sulfonic acid is present in an amount in the range of from 0.0025% to 1.0% based on the total weight of polyalkene.
The present invention further provides the product produced by a process comprising:
(a) copolymerizing (1) a polyalkene containing alkylvinylidene isomer and non-alkylvinylidene isomers and (2) an unsaturated acidic reagent under polymerization conditions in the presence of a free radical initiator; and
(b) reacting the product of step (a) with an unsaturated acidic reagent at elevated temperature in the presence of a strong acid.
Also provided by the present invention is a composition comprising a mixture of (1) a copolymer of a polyalkene and an unsaturated acidic reagent and (2) a polyalkenyl derivative of an unsaturated acidic reagent wherein the weight ratio of copolymer to polyalkenyl derivative is about 0.1-10. This mixture is referred to herein as a “polyPIBSA/acid-catalyzed thermal PIBSA mixture”.
Further provided by the present invention is a polysuccinimide prepared by reacting a polyPIBSA/acid-catalyzed thermal PIBSA mixture of the present invention with an amine, a polyamine having at least two basic nitrogens, or mixture thereof. The present invention also provides a concentrate comprising 10 to 90 weight percent of such a polysuccinimide and from 90 to 10 weight percent of an organic diluent. In addition, the present invention provides a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of such a polysuccinimide. Also provided by the present invention is a post-treated composition prepared by treating such a polysuccinimide under reactive conditions with a cyclic carbonate. Further provided by the present invention is a post-treated composition prepared by treating such a polysuccinimide under reactive conditions with a boron compound.
The present invention further provides a lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of the post-treated composition. Also provided by the present invention is a concentrate comprising 20 to 60 weight percent of the post-treated composition and from 80 to 40 weight percent of an organic diluent.
Also provided by the present invention is a fuel composition comprising a hydrocarbon boiling in the gasoline or diesel range and from about 10 to about 10,000 parts per million of post-treated composition of this invention. Further provided is a fuel concentrate comprising an inert, stable oleophilic solvent boiling in the range of 150-400° F. and at least 5 percent by weight of the post-treated composition of this invention.
Also provided by the present invention is a water-in-oil emulsion comprising a discontinuous aqueous phase comprising at least one oxygen-supplying component, a continuous organic phase comprising at least one carbonaceous fuel, and a minor emulsifying amount of at least one emulsifier comprising the product produced by a process comprising (a) copolymerizing (1) a polyalkene containing alkylvinylidene isomer and non-alkylvinylidene isomers and (2) an unsaturated acidic reagent under polymerization conditions in the presence of a free radical initiator, (b) reacting the product of step (a) with an unsaturated acidic reagent at elevated temperature in the presence of a strong acid, and (c) reacting the product of step (b) with ammonia or at least one amine.
DETAILED DESCRIPTION OF THE INVENTION
The process comprises the steps of copolymerizing a polyalkene and an unsaturated acidic reagent, followed by reacting any unreacted polyalkene with the unsaturated acidic reagent at elevated temperature in the presence of a st
Harrison James J.
Ruhe, Jr. William R.
Asinovsky Olga
Chevron Oronite Company LLC
Jones Josetta I.
Seidleck James J.
Sheridan Richard J.
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