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US4010131A Expired / Lapsed US ⏱️ 0.0 years remaining

Quaternary modified acrylamide polymers

Assignee: ChampionX LLC
•
Filing: 1975-04-18
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Granted: 1977-03-01
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Expires: 1995-04-18
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Abstract

Abstract A method for the preparation of quaternary modified acrylamide polymers is disclosed. Applicable to both solutions of acrylamide polymer and to water-in-oil emulsions of finely divided acrylamide polymer, the method involves reacting the acrylamide with a secondary amine formaldehyde adduct followed by quaternization with an alkylating agent and then, stabilization. The composition of these polymers is also disclosed.

Inventors

  • 👤 Kenneth G. Phillips
  • 👤 Edward G. Ballweber
  • 👤 Karen A. Nordquist
  • 👤 Robert A. Miller

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 13:01
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/02

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 213 words
A process for preparing a stable water soluble quaternary modified acrylamide polymer which comprises the steps of: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 1:2 to 2:1 so as to produce a 0.1 to 55% by weight aqueous solution of the formaldehyde adduct of a secondary amine; B. reacting said formaldehyde adduct of Step A with a 5-50% aqueous solution of an acrylamide polymer having an intrinsic viscosity of from 0.1 to 0.7 in a mole ratio of from 1:2 to 2:1 with mixing at ambient temperatures to produce a cationically modified acrylamide polymer; C. reacting the cationically modified acrylamide of Step B with an alkylating agent, containing 1-7 carbon atoms at alkaline pH and at temperatures between 0-100° C in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 1:1 to 2:1 to produce a stable water soluble quaternary modified acrylamide polymer; and then, D. adding to said water soluble quaternary modified acrylamide polymer a halogen free oxygen containing inorganic acid to a pH of 0-6 to produce a stable water soluble quaternary modified acrylamide polymer.
Claim 2
Dependent Claim 213 words
A process for preparing a stable water soluble quaternary modified acrylamide polymer which comprises the steps of: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 1:2 to 2:1 so as to produce a 0.1 to 55% by weight aqueous solution of the formaldehyde adduct of a secondary amine; B. reacting said formaldehyde adduct of Step A with a 5-50% aqueous solution of an acrylamide polymer having an intrinsic viscosity of from 0.1 to 0.7 in a mole ratio of from 1:2 to 2:1 with mixing at ambient temperatures to produce a cationically modified acrylamide polymer; C. reacting the cationically modified acrylamide of Step B with an alkylating agent, containing 1-7 carbon atoms at alkaline pH and at temperatures between 0-100° C in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 1:1 to 2:1 to produce a stable water soluble quaternary modified acrylamide polymer; and then, D. adding to said water soluble quaternary modified acrylamide polymer a halogen free oxygen containing inorganic acid to a pH of 0-6 to produce a stable water soluble quaternary modified acrylamide polymer.
Claim 3
Dependent Claim 15 words
The process of claim 1 wherein said halogen free oxygen containing acid is sulfurous acid.
Claim 4
Dependent Claim 268 words
A process for preparing a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises the following steps: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 2:1 to 1:2 so as to produce a 0.1 to 55% by weight aqueous solution of said formaldehyde adduct of a secondary amine; B. adding said formaldehyde adduct of Step A to a water-in-oil emulsion of a finely divided acrylamide polymer which contains: a. 10-50% polymer by weight; b. 30-95% of an aqueous phase comprising the polymer and water; c. 5-70% by weight of a hydrophobic liquid; d. 0.1-21.0% by weight of a water-in-oil emulsifying agent; said acrylamide polymer further characterized as having a particle size of from 2 millimicrons to 5 microns within the emulsion, in a mole ratio of said formaldehyde adduct to said polymer of from 1:10 to 10:1 at temperatures of from 32°-200° F with mixing over a time sufficient to produce a water-in-oil emulsion of a finely divided cationically modified acrylamide polymer; and then, C. reacting said water-in-oil emulsion of a finely divided acrylamide polymer of Step B with an alkylating agent containing 1-7 carbon atoms in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 2:1 to 1:0.1 at temperatures of from 20°-100° C for a time sufficient to quaternize said cationically modified acrylamide polymer to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer.
Claim 5
Dependent Claim 268 words
A process for preparing a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises the following steps: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 2:1 to 1:2 so as to produce a 0.1 to 55% by weight aqueous solution of said formaldehyde adduct of a secondary amine; B. adding said formaldehyde adduct of Step A to a water-in-oil emulsion of a finely divided acrylamide polymer which contains: a. 10-50% polymer by weight; b. 30-95% of an aqueous phase comprising the polymer and water; c. 5-70% by weight of a hydrophobic liquid; d. 0.1-21.0% by weight of a water-in-oil emulsifying agent; said acrylamide polymer further characterized as having a particle size of from 2 millimicrons to 5 microns within the emulsion, in a mole ratio of said formaldehyde adduct to said polymer of from 1:10 to 10:1 at temperatures of from 32°-200° F with mixing over a time sufficient to produce a water-in-oil emulsion of a finely divided cationically modified acrylamide polymer; and then, C. reacting said water-in-oil emulsion of a finely divided acrylamide polymer of Step B with an alkylating agent containing 1-7 carbon atoms in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 2:1 to 1:0.1 at temperatures of from 20°-100° C for a time sufficient to quaternize said cationically modified acrylamide polymer to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer.
Claim 6
Dependent Claim 15 words
The process of claim 3 wherein said secondary amine containing 2-8 carbon atoms is dimethylamine.
Claim 7
Dependent Claim 16 words
The process of claim 3 wherein said alkylating agent containing 1-7 carbon atoms is methyl chloride.
Claim 8
Dependent Claim 314 words
A process for preparing a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises the following steps: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 2:1 to 1:2 so as to produce a 0.1 to 55% by weight aqueous solution of said formaldehyde adduct of a secondary amine; B. adding said formaldehyde adduct of Step A to a water-in-oil emulsion of a finely divided acrylamide polymer which contains: a. 10-50% polymer by weight; b. 30-95% of an aqueous phase comprising the polymer and water; c. 5-70% by weight of a hydrophobic liquid; d. 0.1-21.0% by weight of a water-in-oil emulsifying agent; said acrylamide polymer further characterized as having a particle size of from 2 millimicrons to 5 microns within the emulsion, in a mole ratio of said formaldehyde adduct to said polymer of from 1:10 to 10:1 at temperatures of from 32°-200° F with mixing over a time sufficient to produce a water-in-oil emulsion of a finely divided cationically modified acrylamide polymer; C. reacting said water-in-oil emulsion of a finely divided acrylamide polymer of Step B with an alkylating agent containing 1-7 carbon atoms in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 2:1 to 1:0.1 at temperatures of from 20°-100° C for a time sufficient to quaternize said cationically modified acrylamide polymer to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer; and then, D. adding to said water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of Step C a halogen free oxygen containing inorganic acid to a pH of between 0-6 to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability.
Claim 9
Dependent Claim 314 words
A process for preparing a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises the following steps: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 2:1 to 1:2 so as to produce a 0.1 to 55% by weight aqueous solution of said formaldehyde adduct of a secondary amine; B. adding said formaldehyde adduct of Step A to a water-in-oil emulsion of a finely divided acrylamide polymer which contains: a. 10-50% polymer by weight; b. 30-95% of an aqueous phase comprising the polymer and water; c. 5-70% by weight of a hydrophobic liquid; d. 0.1-21.0% by weight of a water-in-oil emulsifying agent; said acrylamide polymer further characterized as having a particle size of from 2 millimicrons to 5 microns within the emulsion, in a mole ratio of said formaldehyde adduct to said polymer of from 1:10 to 10:1 at temperatures of from 32°-200° F with mixing over a time sufficient to produce a water-in-oil emulsion of a finely divided cationically modified acrylamide polymer; C. reacting said water-in-oil emulsion of a finely divided acrylamide polymer of Step B with an alkylating agent containing 1-7 carbon atoms in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 2:1 to 1:0.1 at temperatures of from 20°-100° C for a time sufficient to quaternize said cationically modified acrylamide polymer to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer; and then, D. adding to said water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of Step C a halogen free oxygen containing inorganic acid to a pH of between 0-6 to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability.
Claim 10
Dependent Claim 16 words
The process of claim 6 wherein said halogen free oxygen containing inorganic acid is sulfurous acid.
Claim 11
Dependent Claim 365 words
A process for preparing a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises the following steps: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 2:1 to 1:2 so as to produce a 0.1 to 55% by weight aqueous solution of said formaldehyde adduct of a secondary amine; B. adding said formaldehyde adduct of Step A to a water-in-oil emulsion of a finely divided acrylamide polymer which contains: a. 10-50% polymer by weight; b. 30-95% of an aqueous phase comprising the polymer and water; c. 5-70% by weight of a hydrophobic liquid; d. 0.1-21.0% by weight of a water-in-oil emulsifying agent; said acrylamide polymer further characterized as having a particle size of from 2 millimicrons to 5 microns within the emulsion, in a mole ratio of said formaldehyde adduct to said polymer of from 1:10 to 10:1 at temperatures of from 32°-200° F with mixing over a time sufficient to produce a water-in-oil emulsion of a finely divided cationically modified acrylamide polymer; C. reacting said water-in-oil emulsion of a finely divided acrylamide polymer of Step B with an alkylating agent containing 1-7 carbon atoms in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 2:1 to 1:0.1 at temperatures of from 20°-100° C for a time sufficient to quaternize said cationically modified acrylamide polymer to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer; D. adding to said water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of step C a halogen free, oxygen containing inorganic acid to a pH of between 0-6 to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability; and then, E. heating said water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability from Step D at temperatures of from 30°-90° C for a time sufficient to enable said quaternary modified acrylamide polymer to fully invert giving high cationic charge values when added to a dilute aqueous solution.
Claim 12
Dependent Claim 365 words
A process for preparing a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises the following steps: A. preparing a formaldehyde adduct of a secondary amine containing 2-8 carbon atoms by mixing together an aqueous formaldehyde solution and a secondary amine containing 2-8 carbon atoms in a mole ratio of from 2:1 to 1:2 so as to produce a 0.1 to 55% by weight aqueous solution of said formaldehyde adduct of a secondary amine; B. adding said formaldehyde adduct of Step A to a water-in-oil emulsion of a finely divided acrylamide polymer which contains: a. 10-50% polymer by weight; b. 30-95% of an aqueous phase comprising the polymer and water; c. 5-70% by weight of a hydrophobic liquid; d. 0.1-21.0% by weight of a water-in-oil emulsifying agent; said acrylamide polymer further characterized as having a particle size of from 2 millimicrons to 5 microns within the emulsion, in a mole ratio of said formaldehyde adduct to said polymer of from 1:10 to 10:1 at temperatures of from 32°-200° F with mixing over a time sufficient to produce a water-in-oil emulsion of a finely divided cationically modified acrylamide polymer; C. reacting said water-in-oil emulsion of a finely divided acrylamide polymer of Step B with an alkylating agent containing 1-7 carbon atoms in a mole ratio of alkylating agent to tertiary amine groups on said cationically modified acrylamide polymer of from 2:1 to 1:0.1 at temperatures of from 20°-100° C for a time sufficient to quaternize said cationically modified acrylamide polymer to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer; D. adding to said water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of step C a halogen free, oxygen containing inorganic acid to a pH of between 0-6 to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability; and then, E. heating said water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability from Step D at temperatures of from 30°-90° C for a time sufficient to enable said quaternary modified acrylamide polymer to fully invert giving high cationic charge values when added to a dilute aqueous solution.
Claim 13
Dependent Claim 191 words
A stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises: A. a water-in-oil emulsion of a finely divided acrylamide polymer which contains from 10 to 50% by weight acrylamide polymer, 25 to 85% by weight water, 5 to 40% by weight of a hydrophobic liquid, and from 0.1 to 5% by weight of a water-in-oil emulsifying agent; which has been reacted with, B. a quantity of an aqueous solution which contains from 0.1-55% by weight of an adduct made from formaldehyde, and a secondary amine, containing a 2-8 carbon atoms, said adduct being formed from reacting an aqueous formaldehyde solution with a secondary amine containing 2-8 carbon atoms in molar ratios of from 1:10 to 10:1, so that the molar ratio of said formaldehyde adduct to said acrylamide polymer is from 2:1 to 1:2; and then adding, C. an alkylating agent containing 1-7 carbon atoms at an alkaline pH at temperatures from 0°-100° C in a molar ratio of tertiary amine on said acrylamide polymer to alkylating agent of from 2:1 to 1:2 to produce a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer.
Claim 14
Dependent Claim 191 words
A stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer which comprises: A. a water-in-oil emulsion of a finely divided acrylamide polymer which contains from 10 to 50% by weight acrylamide polymer, 25 to 85% by weight water, 5 to 40% by weight of a hydrophobic liquid, and from 0.1 to 5% by weight of a water-in-oil emulsifying agent; which has been reacted with, B. a quantity of an aqueous solution which contains from 0.1-55% by weight of an adduct made from formaldehyde, and a secondary amine, containing a 2-8 carbon atoms, said adduct being formed from reacting an aqueous formaldehyde solution with a secondary amine containing 2-8 carbon atoms in molar ratios of from 1:10 to 10:1, so that the molar ratio of said formaldehyde adduct to said acrylamide polymer is from 2:1 to 1:2; and then adding, C. an alkylating agent containing 1-7 carbon atoms at an alkaline pH at temperatures from 0°-100° C in a molar ratio of tertiary amine on said acrylamide polymer to alkylating agent of from 2:1 to 1:2 to produce a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer.
Claim 15
Dependent Claim 225 words
A stable water-in-oil emulsion of a finely divided cationically modified acrylamide polymer which comprises: A. a water-in-oil emulsion of a finely divided acrylamide polymer which contains from 10 to 50% by weight acrylamide polymer, 25 to 85% by weight water, 5 to 40% by weight of a hydrophobic liquid, and from 0.1 to 5% by weight of a water-in-oil emulsifying agent; which has been reacted with, B. a quantity of an aqueous solution which contains from 0.1-55% by weight of an adduct made from formaldehyde and a secondary amine containing 2-8 carbon atoms, said adduct being formed from reacting an aqueous formaldehyde solution with a secondary amine containing 2-8 carbon atoms in molar ratios of from 1:10 to 10:1, so that the molar ratio of said formaldehyde adduct to said acrylamide polymer is from 2:1 to 1:2; and then adding, C. an alkylating agent containing 1-7 carbon atoms at an alkaline pH at temperatures of from 0-100° C in a mole ratio of tertiary amine on said acrylamide polymer to alkylating agent of from 2:1 to 1:2 to produce a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer; to which is then added, D. a halogen free, oxygen containing inorganic acid to a pH of 0-6 to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability.
Claim 16
Dependent Claim 225 words
A stable water-in-oil emulsion of a finely divided cationically modified acrylamide polymer which comprises: A. a water-in-oil emulsion of a finely divided acrylamide polymer which contains from 10 to 50% by weight acrylamide polymer, 25 to 85% by weight water, 5 to 40% by weight of a hydrophobic liquid, and from 0.1 to 5% by weight of a water-in-oil emulsifying agent; which has been reacted with, B. a quantity of an aqueous solution which contains from 0.1-55% by weight of an adduct made from formaldehyde and a secondary amine containing 2-8 carbon atoms, said adduct being formed from reacting an aqueous formaldehyde solution with a secondary amine containing 2-8 carbon atoms in molar ratios of from 1:10 to 10:1, so that the molar ratio of said formaldehyde adduct to said acrylamide polymer is from 2:1 to 1:2; and then adding, C. an alkylating agent containing 1-7 carbon atoms at an alkaline pH at temperatures of from 0-100° C in a mole ratio of tertiary amine on said acrylamide polymer to alkylating agent of from 2:1 to 1:2 to produce a stable water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer; to which is then added, D. a halogen free, oxygen containing inorganic acid to a pH of 0-6 to produce a water-in-oil emulsion of a finely divided quaternary modified acrylamide polymer of greater stability.

References Cited (Backward Citations)

US2328901A Cited
US2935493A Cited
US3284393A Cited
US3556932A Cited
US3539535A Cited
US3766156A Cited
US3624019A Cited
US3734873A Cited

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