Fuel and related compositions – Liquid fuels – Heterocyclic carbon compound containing a hetero ring having...
Reexamination Certificate
2000-01-24
2004-08-24
Toomer, Cephia D. (Department: 1714)
Fuel and related compositions
Liquid fuels
Heterocyclic carbon compound containing a hetero ring having...
C044S351000, C044S386000, C044S388000, C044S389000, C044S408000, C044S418000, C071S027000, C071S064080, C149S061000, C508S287000, C508S290000, C508S291000, C508S306000, C508S463000, C508S527000, C508S528000, C508S530000, C516S027000
Reexamination Certificate
active
06780209
ABSTRACT:
TECHNICAL FIELD
This invention relates to partially dehydrated reaction products derived from (A) a hydrocarbyl substituted succinic acid or anhydride, and (B) a polyol, polyamine, hydroxyamine or mixture of two or more thereof. The invention also relates to a process for making these partially dehydrated reaction products. The inventive reaction products are useful as emulsifiers in making emulsions, especially explosive emulsions and emulsion fertilizers.
BACKGROUND OF THE INVENTION
Explosive emulsions typically comprise a continuous organic phase and a discontinuous oxidizer phase containing water and an oxygen-supplying source such as ammonium nitrate, and an emulsifier. Examples of such explosive emulsions are disclosed, inter alia, in U.S. Pat. Nos. 4,708,753 and 5,920,031. In U.S. Pat. No. 4,708,753 the emulsifier is a salt derived from a hydrocarbyl-substituted carboxylic acid or anhydride, or ester or amide derivative of said acid or anhydride, the hydrocarbyl substituent having an average of from about 20 to about 500 carbon atoms, and an amine. In U.S. Pat. No. 5,920,031 the emulsifier is the product made by the reaction of component (A) with component (B). Component (A) is a 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. Component (B) is ammonia and/or a mono-amine.
U.S. Pat. No. 5,512,079 discloses an emulsion fertilizer comprising a discontinuous aqueous phase comprising at least one fertilizer component such as ammonium nitrate; a continuous oil phase; and an emulsifier. The emulsifier is the reaction product of a hydrocarbyl substituted succinic anhydride acylating agent and a tertiary alkanol amine.
A problem in the explosive emulsion and emulsion fertilizer arts relates to the fact that it is desirable to lower the viscosities of the emulsions in order to improve their pumping and handling characteristics. It is also desirable to make emulsions with relatively high aqueous phase to organic phase weight ratios. This is advantageous with explosive emulsions because it permits the delivery of more of the oxygen-supplying source with the same weight of emulsion. Similarly, this is advantageous with emulsion fertilizers because it permits the delivery of more of the fertilizer component with the same weight of emulsion. Unexpectedly, by use of the inventive reaction products as emulsifiers it is possible to formulate explosive emulsions and emulsion fertilizers having these characteristics. Going beyond explosive emulsions and emulsion fertilizers, the inventive reaction products are useful as emulsifiers in a wide variety of applications.
PCT publication WO96/25384 discloses monomeric, aligomeric and polymeric bisesters of alkyl- or alkenyldicarboxylic acid derivatives and polyalcohols, and their use as solubilizers, emulsifiers and/or detergents. The bisesters are described as being useful in formulating cosmetic compositions, detergents and cleaners, pharmaceutical compositions, foodstuffs and crop protection compositions. A process for preparing these bisesters is disclosed.
SUMMARY OF THE INVENTION
This invention relates to a composition comprising a partially dehydrated product made by:
(I) reacting (A) a hydrocarbyl substituted succinic acid or anhydride with (B) a polyol, a polyamine, a hydroxyamine, or a mixture of two or more thereof, to form a first intermediate product comprising: an ester, partial ester or mixture thereof when (B) is a polyol; an amide, imide, salt, amide/salt, partial amide or mixture of two or more thereof when (B) is a polyamine; or an ester, partial ester, amide, partial amide, amide/salt, imide, ester/salt, salt or a mixture of two or more thereof when (B) is a hydroxyamine, a mixture of a polyol and a polyamine, a mixture of a polyol and a hydroxyamine, a mixture of a polyamine and a hydroxyamine, or a mixture of a polyol, a polyamine and a hydroxyamine; the hydrocarbyl substitutent of said acid or anhydride having an average of about 8 to about 200 carbon atoms; and
(II) heating said first intermediate product at an effective temperature to form a second intermediate product with water of reaction being formed, and separating a portion of said water of reaction from said second intermediate product to form said partially dehydrated product, when (A) is said succinic anhydride the amount of water of reaction that is separated is from about 0.2 to about 0.9 moles of said water of reaction per equivalent of said succinic anhydride, when (A) is said succinic acid the amount of water of reaction that is separated is from about 1.2 to about 1.9 moles of said water of reaction per equivalent of said succinic acid, said partially dehydrated product having an acid number in the range of about 20 to about 100 mg of KOH/g.
This invention also relates to a process, comprising:
(I) reacting (A) a hydrocarbyl substituted succinic acid or anhydride with (B) a polyol, a polyamine, a hydroxyamine, or a mixture of two or more thereof, to form a first intermediate product comprising: an ester, partial ester or mixture thereof when (B) is a polyol; an amide, imide, salt, amide/salt, partial amide or mixture of two or more thereof when (B) is a polyamine; or an ester, partial ester, amide, partial amide, amide/salt, imide, ester/salt, salt or a mixture of two or more thereof when (B) is a hydroxyamine; a mixture of a polyol and a polyamine, a mixture of a polyol and a hydroxyamine, a mixture of a polyamine and a hydroxyamine, or a mixture of a polyol, a polyamine and a hydroxyamine; the hydrocarbyl substituent of said acid or anhydride having an average of about 8 to about 200 carbon atoms; and
(II) heating said first intermediate product at an effective temperature to form a second intermediate product with water of reaction being formed, and separating a portion of said water of reaction from said second intermediate product to form said partially dehydrated product, when (A) is said succinic anhydride the amount of water of reaction that is separated is from about 0.2 to about 0.9 equivalents of said water of reaction per equivalent of said succinic anhydride, when (A) is said succinic acid the amount of water of reaction that is separated is from about 1.2 to about 1.9 moles of said water of reaction per equivalent of said succinic acid, said partially dehydrated product having a total acid number in the range of about 20 to about 100 mg of KOH/g.
This invention also relates to emulsions, comprising: an organic phase; an aqueous phase; and an emulsifying amount of the foregoing partially dehydrated product.
As indicated above, the inventive partially dehydrated reaction products are useful as emulsifiers in formulating emulsions for a wide variety of applications. These include one or more of the following: lubricants or functional fluids; fuels; paints; coatings; inks; caulks or adhesives; fertilizers or agricultural chemicals; refinery or oil-field products; mining products; explosives; commodity chemical manufacturing processes; processes involving the use of emulsions containing 2-acrylamido-2-methyl-1-propane sulfonic acid monomer; and the like.
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Filippini Brian B.
Grisso Bryan A.
Hird Bryn
Lange Richard M.
Esposito Michael F.
Laferty Samuel B.
The Lubrizol Corporation
Toomer Cephia D.
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