Air Products and Chemicals, Inc.

Other

Henkel Research Corporation

Ta-Wang Lai

Robert K Pinschmidt, Jr

Bheema R Vijayendran

Robert Krantz Pinschmidt

Ta Yen Ching

William F Burgoyne, Jr

Christine A Costello

Lawrence K Wempe

Richard M Chan

Christine Ann Costello

Bheema Rao Vijayendran

Vinyl acetate and an N-vinyl formamide are copolymerized to yield poly(vinyl acetate)-co-poly(N-vinyl formamide) which is base hydrolyzed to poly(vinyl alcohol)-co-poly(N-vinyl formamide). Two phase hydrolysis of particles of poly(vinyl alcohol)-co-poly(N-vinyl formamide) as a slurry in methanol yields particles of poly(vinyl alcohol)-co-poly(vinylamine). provided is a copolymer of the following general formula ##STR1## where m is 0 to 15 mole %. n is 50 to 99 mole %.

Method for preparing poly(vinyl alcohol)-co-poly(vinylamine) via a

Vinyl acetate and an N-vinyl formamide are copolymerized to yield poly(vinyl acetate)-co-poly(N-vinyl formamide) which is base hydrolyzed to poly(vinyl alcohol)-co-poly(N-vinyl formamide). Two phase hydrolysis of particles of poly(vinyl alcohol)-co-poly(N-vinyl formamide) as a slurry in methanol yields particles of poly(vinyl alcohol)-co-poly(vinylamine). Provided is a copolymer of the following general formula ##STR1## where m is 0 to 15 mole %,

Two-phase process for preparing poly(vinyl alcohol)-co-poly(vinylamine)

Curing agents for epoxy resins composed of (a) the reaction product of a co-reactant comprising either an epichlorohydrin (co) polymer or a (co)polymer of a chlorovinyl acetate, chloroalkyl acrylate with an organic amino compound containing at least one active hydrogen and having a pK.sub.B value within the range of from about 7 to about 9, preferably imidazole and substituted imidazoles; (b) an N-fatty imidazole and (a); (c) an N-fatty imidazole and an elastomeric polymer are disclosed. The curing agents are essentially water insoluble and give rise to epoxy resins which may be cured at relatively low temperatures below about 100.degree. C. The epoxy resins are suitable for use as adhesives, coatings and in composite applications.

Epichlorohydrin or chlorine-containing vinyl or acrylate

A modified poly(vinyl alcohol) copolymer is provided containing copolymerized units of allylamine and/or diallylamine by copolymerizing a vinyl ester, such as vinyl acetate, and an N-allylamide and/or N,N-diallylamide, such as N-allylformamide and/or N,N-diallylformamide and hydrolyzing first the ester groups to hydroxy groups and then the amide groups to amine groups. The second hydrolysis is carried out on solvent-swollen particulate polymer slurried in an acidic or basic medium. The modified polymer can contain small amounts of unhydrolyzed ester and amide groups in addition to the hydroxy and amine functionality which characterizes the copolymer.

Vinyl alcohol copolymers containing allylamine functionality

Polyvinylaminals, optionally as the formed copolymer with polyvinylhemiaminals, and polyvinylacetals are useful as flocculants and epoxy resin and polyurethane crosslinking agents and are provided by reacting a poly(vinylamine) or a copolymer containing vinyl alcohol and vinylamine units with a monoaldehyde. The aldehyde, such as butyraldehyde, can be introduced in the polymer acetalization as a liquid or gas, generally in a proportion of about 0.02 to 0.5 mol per mol of alcohol and amine units in the polymer chain.

Amine functional polymers containing acetal groups

The production of oil or gas from a subterranean formation is enhanced by injecting into the formation, such as in acidized fracturing, an aqueous fluid containing as a viscosifier a crosslinked vinylamine polymer. Acidizing fluids are provided containing HCl and a viscosifying amount of a gel of the crosslinked polymer, preferably poly(vinylamine) crosslinked with a diisocyanate, a polyepoxide or epichlorohydrin.

Crosslinked vinylamine polymer in enhanced oil recovery

The inverse emulsion polymerization of a monomer of the formula ##STR1## wherein R and R.sup.1 represent hydrogen of a C.sub.1 -C.sub.4 alkyl group, using a surfactant system having a hydrophilic-lipophilic balance value from 4 to 9, an azo-type free radical initiator and certain hydrocarbon liquids to yield a water-in-oil emulsion of a homopolymer of at least 10.sup.6 average molecular weight, the emulsion having a viscosity less than 10 cps, at 15% solids, 60 rpm Brookfield and 20.degree. C. Also disclosed is the preparation of poly(vinylamines) of at least 10.sup.6 average molecular weight by acid or base hydrolysis of the homopolymer emulsion. Also disclosed are drilling mud compositions, cements for drilling holes, completion fluids, acidized fracturing fluids, and wet-end paper additives containing the poly(vinylamines) and demonstrating superior properties.

Manufacture of high molecular weight poly(vinylamines)

Poly(N-vinylformamide) is thermolytically reacted to yield poly(N-vinylamine).

Thermolysis of poly(N-vinylformamide) to poly(N-vinylamine)

The recovery of oil or gas from underground porous formations bearing such hydrocarbons is enhanced by using an injection fluid containing a viscosifying amount of a poly(vinylamine) formed in-situ by hydrolysis of a high molecular weight poly(N-vinylamide). The hydrolysis conditions are strongly acidic or highly alkaline and include the elevated temperature of the formation. The poly(N-vinylamide), such as poly(N-vinylformamide), can be made by inverse emulsion polymerization and the high solids emulsion mixed directly with the acidic or basic solutions to form the injection fluid.

Enhanced oil recovery with high molecular weight polyvinylamine formed

An amine functional copolymer of vinyl alcohol is provided by copolymerizing a vinylester with a morpholinoalkylvinylether or a morpholinoalkylallylether and then hydrolyzing the ester groups in the copolymer to hydroxy groups. The preferred copolymer is formed from vinyl acetate and morpholinoethylvinylether and 1 to 30 mol percent of the polymerized ethylene linkages in the polymer backbone contain pendant morpholinoethylether groups.

Modified poly(vinyl alcohol) containing morpholinoalkylether groups

Aqueous, clay-based drilling mud compositions are improved with respect to waterloss control by the addition of a hydrolyzed copolymer of acrylamide and an N-vinylamide. The copolymer, which is effective over a broad range of molecular weights, contains at least 5 mol percent of the N-vinylamide monomer moiety of which at least 5 mol percent is hydrolyzed to vinylamine units. Well drilling is improved by circulating through the bore hole a drilling mud containing this waterloss control additive.

Hydrolyzed co-polymers of N-vinylamide and acrylamide for use as

The inverse emulsion polymerization of a monomer of the formula ##STR1## wherein R and R.sup.1 represent hydrogen or a C.sub.1 -C.sub.4 alkyl group, using a surfactant system having a hydrophilic-lipophilic balance value from 4 to 9, an azo-type free radical initiator and certain hydrocarbon liquids to yield a water-in-oil emulsion of a homopolymer of at least 10.sup.6 average molecular weight, the emulsion having a viscosity less than 10 cps, at 15% solids, 60 rpm Brookfield and 20.degree. C. Also disclosed is the preparation of poly(vinylamines) of at least 10.sup.6 average molecular weight by acid or base hydrolysis of the homopolymer emulsion. Also disclosed are enhanced oil recovery compositions, drilling mud compositions, cements for drilling holes, completion fluids, acidized fracturing fluids, and wet-end paper additives containing the poly(vinylamines) and demonstrating superior properties.

Acidized fracturing fluids containing high molecular weight

The inverse emulsion polymerization of a monomer of the formula ##STR1## wherein R and R.sup.1 represent hydrogen or a C.sub.1 -C.sub.4 alkyl group, using a surfactant system having a hydrophilic-lipophilic balance value from 4 to 9, an azo-type free radical initiator and certain hydrocarbon liquids to yield a water-in-oil emulsion of a homopolymer of at least 10.sup.6 average molecular weight, the emulsion having a viscosity less than 10 cps, at 15% solids, 60 rpm Brookfield and 20.degree. C. Also disclosed is the preparation of poly(vinylamines) of at least 10.sup.6 average molecular weight by acid or base hydrolysis of the homopolymer emulsion. Also disclosed are completion fluids for oil field applications containing the poly(vinylamines) and demonstrating superior properties.

Completion fluids containing high molecular weight poly(vinylamines)

The inverse emulsion polymerization of a monomer of the formula ##STR1## wherein R and R.sup.1 represent hydrogen or a C.sub.1 -C.sub.4 a lkyl group, using a surfactant system having a hydrophilic-lipophilic balance value from 4 to 9, an azo-type free radical initiator and certain hydrocarbon liquids to yield a water-in-oil emulsion of a homopolymer of at least 10.sup.6 average molecular weight, the emulsion having a viscosity less than 10 cps, at 15% solids, 60 rpm Brookfield and 20.degree. C.

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Novato, CA, United States of America

Ta-Wang Lai