# US 4,383,054 A · Hydrophilic high polymers prepared from aqueous solutions or dispersions of polyoxypropylene polyamine N-N'-polymethylene sulfonates

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- Number: US 4,383,054 A
- Document ID: US4383054A
- Status: Granted
- Kind: A
- Application number: 06/268,038
- Filed: 1981-05-28
- Granted: 1983-05-10
- Earliest claimed: 1981-05-28
- Assignees: Texaco Inc.
- Inventors: Heinz Schulze; Harold G. Waddill
- Web page: https://patentgrep.com/patent/US4383054A

## CPC

- E21D 9/002: {Injection methods characterised by the chemical composition used}
- C08G 59/504: {containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen}
- C08G 65/3346: {having sulfur bound to carbon and oxygen}
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C09K 8/5755: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds}
- E21D: SHAFTS; TUNNELS; GALLERIES; LARGE UNDERGROUND CHAMBERS (soil-conditioning or soil-stabilising materials C09K17/00; drilling or cutting machines for mining or quarrying E21C; safety devices, transport, rescue, ventilation or drainage E21F)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A self curing aqueous solution/dispersion comprising about 50-70 wt. % water, about 25-35 wt. % of a novel N-polymethylene substituted polyoxypropylene polyamine and about 3-9 wt. % of a curable polymer-forming component such as an epoxy-resin is described. The solution is useful for injection into permeable earth formations such as unconsolidated sands to reduce their permeability and consolidate the formation. Novel N-substituted polyamines of the formula [NaO.sub.3 S--R.sub.1 ].sub.m A wherein R.sub.1 is a C.sub.2 to C.sub.6 polymethylene group and A is a polyoxyalkylene polyamine are employed in the solution to render the epoxy-resin component adequately soluble or dispersible in the aqueous solution and to act as the curing agent for the resin.

## Claims

### Claim 1

N-polymethylene sulfonate substituted polyoxyalkylene polyamines of the formula
[NaO.sub.3 S--R.sub.1 ].sub.m A
wherein R.sub.1 is a polymethylene group or a hydroxy substituted polymethylene group having from 2 to 6 carbon atoms, m is from 2 to 4 and A is a polyoxyalkylene polyamine.

### Claim 2 (depends on 1)

The compounds of claim 1 wherein the N-polymethylene sulfonate substituted polyoxyalkylene polyamine is a diamine of the formula ##STR5## wherein R is an alkylene group containing from 2 to 5 carbon atoms, R.sub.1 is a polymethylene group or a hydroxy substituted polymethylene group containing from 2 to 6 carbon atoms and n is from about 2.6 to about 33.1.

### Claim 3 (depends on 2)

The compounds of claim 2, wherein R.sub.1 is a trimethylene group or a 2-hydroxy trimethylene group.

### Claim 4 (depends on 3)

The compounds of claim 3, comprising polyoxypropylene diamine N,N'-bis(2-hydroxy trimethylene sodium sulfonate).

### Claim 5

An aqueous solution for injection into a subterranean formation to decrease the permeability of such formation, comprising:
an aqueous solution containing a N-polymethylene sulfonate substituted polyoxyalkylene polyamine of the formula
[NaO.sub.3 S--R.sub.1 ].sub.m A
wherein R.sub.1 is a polymethylene group or a hydroxy substituted polymethylene group having from 2 to 6 carbon atoms, m is from 2 to 4 and A is a polyoxyalkylene polyamine;
and an epoxy-resin; wherein
the aqueous solution contains from about 50 to about 70% by weight water, from about 25 to about 35% by weight N-polymethylene sulfonate substituted polyoxyalkylene polyamine, and from about 3 to about 9% by weight epoxy-resin.

### Claim 6 (depends on 1, 5)

The solution of claim 5, wherein the compounds of claim 1 wherein the N-polymethylene sulfonate substituted polyoxyalkylene polyamine is a diamine of the formula ##STR6## wherein R is an alkylene group containing from 2 to 5 carbon atoms, R.sub.1 is a polymethylene group or a hydroxy substituted polymethylene group containing from 2 to 6 carbon atoms and n is from 2.6 to about 33.1.

### Claim 7 (depends on 6)

The solution of claim 6, wherein R.sub.1 is a trimethylene group.

### Claim 8 (depends on 6)

The solution of claim 6, wherein the N-polymethylene sulfonate substituted polyoxyalkylene polyamine is polyoxypropylene diamine N,N'-bis-(2-hydroxy trimethylene sodium sulfonate).

### Claim 9 (depends on 5, 6, 7, 8)

The solution of claims 5, 6, 7 or 8 wherein the epoxy-resin is a glycidyl polyether of a dihydric phenol.

### Claim 10 (depends on 9)

The solution of claim 9, wherein the epoxy-resin is resin of bis-phenol A.

### Claim 11 (depends on 9)

The solution of claim 9, wherein the epoxy-resin has an epoxy equivalent weight of from about 175 to about 210.

### Claim 12 (depends on 11)

The solution of claim 11, wherein the N-polymethylene sulfonate substituted polyoxyalkylene polyamine is present in an amount which is between about 20 to about 120 percent of the stoichiometric amount required for reaction with the epoxy-resin.