Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2001-12-20
2003-05-27
Hampton-Hightower, P. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S097000, C528S099000, C528S104000, C528S109000, C528S111000, C528S121000, C528S124000, C523S130000, C523S131000, C166S270000, C166S275000, C166S295000
Reexamination Certificate
active
06569983
ABSTRACT:
TECHNICAL FIELD
This invention provides compounds, compositions and methods for the recovery of hydrocarbon fluids from a subterranean reservoir. More particularly, this invention concerns water-soluble branched polyhydroxyetheramines that modify the permeability of subterranean formations and increase the mobilization and/or recovery rate of hydrocarbon fluids present in the formations.
BACKGROUND OF THE INVENTION
The production of large amounts of water from oil and gas wells constitutes one of the major expenses in the overall recovery of hydrocarbons from a subterranean formation. Many producing oil wells produce a gross effluent having greater than 80% by volume water. Therefore, most of the pumping energy is expended by lifting water from the well. Then the production effluent must be subjected to expensive separation procedures in order to recover water-free hydrocarbons. The water constitutes a troublesome and an expensive disposal problem.
Therefore, it is highly desirable to decrease the amount of water produced from oil and gas wells. Another beneficial effect of decreasing the amount of produced water is realized by decreasing the flow of water in the well bore at a given pumping rate thereby lowering the liquid level over the pump in the well bore, thereby reducing the back pressure in the formation and improving pumping efficiency and net daily oil production.
SUMMARY OF THE INVENTION
We have discovered a family of novel branched polyhydroxyetheramine polymers that effectively reduce the amount of water recovered from subterranean, hydrocarbon-bearing formations, thereby increasing the production rate of hydrocarbons from the formation. The polymers of this invention are particularly effective at decreasing the water permeability with little effect on the oil permeability. Ester comb polymers decrease the water permeability but also significantly reduce the oil permeability. The polymers of this invention are also particularly effective for use in gas and oil wells that operate at temperatures higher than about 200° F. where polymers such as polyacrylamide (PAM), hydrolyzed polyacrylamide (HPAM) and ester-containing polymers are less effective due to hydrolysis of the ester or amide-functionality.
Accordingly, in its principal aspect, this invention is directed to a water-soluble branched polyhydroxyetheramine, wherein the branched polyhydroxyetheramine is prepared by reacting an amine having two reactive hydrogen atoms with a diepoxide to form a polyhydroxyetheramine and then reacting the polyhydroxyetheramine with an N-alkylating agent.
DETAILED DESCRIPTION OF THE INVENTION
“Acyl” means a group of formula R′C(O)—where R′ is C
1
-C
8
alkyl. C
1
-C
2
alkyl groups are preferred. Representative acyl groups include acetyl, propionyl, butyryl, and the like.
“Alkoxy” means a C
1
-C
8
alkyl group attached to the parent molecular moiety through an oxygen atom. Representative alkoxy groups include methoxy, ethoxy, propoxy, butoxy, and the like. Methoxy and ethoxy are preferred.
“Alkyl” means a monovalent group derived from a straight or branched chain saturated hydrocarbon by the removal of a single hydrogen atom. Representative alkyl groups include methyl, ethyl, n- and iso-propyl, n-, sec-, iso- and tert-butyl, and the like.
“Alkylamido” means a group of formula R′NHC(O)—where R′ is C
1
-C
8
alkyl. C
1
-C
2
alkyl groups are preferred.
“Alkylcarbonyl” means a C
2
-C
8
alkyl group where the alkyl chain is interrupted with a carbonyl (>C═O) group (i.e. an alkyl-C(O)-alkylene-group). Representative alkylcarbonyl groups include methylcarbonymethyl, ethylcarbonylmethyl, methylcarbonylethyl, (2-methylpropyl)carbonylmethyl, and the like.
“Alkylene” means a divalent group derived from a straight or branched chain saturated hydrocarbon by the removal of two hydrogen atoms, for example methylene, 1,2-ethylene, 1,1-ethylene, 1,3-propylene, 2,2-dimethylpropylene, and the like.
“Amine having two reactive hydrogen atoms” means an amine having two N—H groups, where the N—H groups are sufficiently reactive to react with the epoxide groups of a diepoxide as defined herein to form a polyhydroxyetheramine. The amine having two reactive hydrogen atoms may be a primary amine, or a compound containing two secondary amino groups, where the compound containing two secondary amino groups may be cyclic or acyclic. The amine having two reactive hydrogen atoms is optionally substituted with one or more with alkylamido, dialkylamino, hydroxy, hydroxyalkyl, alkoxy, halo, cyano, aryloxy, alkylcarbonyl or arylcarbonyl groups.
“Aryl” means substituted and unsubstituted aromatic carbocyclic radicals and substituted and unsubstituted heterocyclic having from 5 to about 14 ring atoms. Representative aryl include phenyl naphthyl, phenanthryl, anthracyl, pyridyl, furyl, pyrrolyl, quinolyl, thienyl, thiazolyl, pyrimidyl, indolyl, and the like. The aryl is optionally substituted with one or more alkylamido, hydroxy, alkoxy, halo, cyano, aryloxy, alkylcarbonyl or arylcarbonyl groups.
“Arylalkyl” means means an aryl group attached to the parent molecular moiety through a C
1
-C
8
alkylene group. C
1
-C
2
alkylene groups are preferred. Representative arylalkyl groups include phenylmethyl, phenylethyl, phenylpropyl, 1-naphthylmethyl, and the like.
“Arylcarbonyl” means an aryl group attached to the parent molecular moiety through a carbonyl group. Representative arylcarbonyl include benzoyl and substituted benzoyl.
“Aryloxy” means an aryl group attached to the parent molecular moiety through an oxygen atom. Representative aryloxy groups include phenoxy, pyridyloxy, and the like.
“Cycloalkylene” means a divalent group derived from a saturated carbocyclic hydrocarbon by the removal of two hydrogen atoms, for example cyclopentylene, cyclohexylene, and the like.
“Dialkylamino” means a group having the structure —NR′R″ wherein R′ and R″ are independently selected from C
1
-C
8
alkyl. C
1
-C
2
alkyl are preferred. Additionally, R′ and R″ taken together may optionally be —(CH
2
)
k
— where k is an integer of from 2 to 6. Examples of dialkylamino include, dimethylamino, diethylaminocarbonyl, methylethylamino, piperidino, and the like.
“Halo” and “halogen” mean chlorine, fluorine, bromine and iodine.
“Diepoxide” means a cyclic or acyclic compound containing two epoxide groups. Representative diepoxides include diglycidyl esters of diacids, diglycidyl ethers of diols, epoxidized olefins, and the like.
“Diglycidyl ester of a diacid” means a diepoxide of formula
where R
6
is C
2
-C
36
alkylene or C
5
-C
8
cycloalkylene, where the alkylene is optionally interrupted with a cylcloalkylene group, and where the alkylene or cycloalkylene is optionally substituted with one or more alkylamido, hydroxy, alkoxy, halo, cyano, aryloxy, alkylcarbonyl or arylcarbonyl groups. A preferred diglycidyl ester of a diacid is diglycidyl ether of dimer acid.
“Diglycidyl ether of a diol” means a compound of formula
where R
7
is C
2
-C
20
alkylene or C
2
-C
40
alkoxy, where the alkylene is optionally interrupted with a cycloalkylene group and the alkylene or alkoxy is optionally substituted with one or more alkylamido, hydroxy, alkoxy, halo, cyano, aryloxy, alkylcarbonyl or arylcarbonyl groups. Preferred diglycidyl ethers of a diol include bis(2,3-epoxypropyl)ether, diglycidyl ether of 1,4-butanediol, diglycidyl ether of neopentyl glycol, diglycidyl ether of ethylene glycol, glycerol diglycidyl ether, diglycidyl ether of polyethyleneglycols, diglycidyl ether of polypropylene glycols, diglycidyl ether of glycols from the reaction of ethylene oxide with propylene oxide, diglycidyl ether of cyclohexane dimethanol, and the like.
“Epoxidized olefin” means a compound of formula
where R
9
is C
2
-C
20
alkylene, where the alkylene is optionally interrupted with a cylcloalkylene group and optionally substituted with one or more alkylamido, hydroxy, alkoxy, halo, cyano, aryloxy, alkylcarbonyl or arylcarbonyl groups and R
8
and R
10
are H or R
8
and R
10
are connected
Chang Kin-Tai
Treybig Duane
Williams Dennis
Breininger Thomas M.
Hampton-Hightower P.
Martin Michael B.
Ondeo Nalco Energy Services, L.P.
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