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Process for obtaining and product acrylic monomers useful in the preparation of cationic flocculants

Assignee: Rhone Poulenc Industries SA
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Filing: 1977-04-11
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Granted: 1979-12-25
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Expires: 1997-04-11
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Abstract

Abstract Process for preparing acrylic monomers comprising reacting, in aqueos medium, amino alkyl esters of (meth) acrylic acid with a quaternizing agent wherein the aqueous solution obtained is washed with a water-insoluble solvent and the solvent thereafter removed. The quaternized monomers prepared are directly polymerizable to high molecular weight homopolymers or copolymers useful as cationic flocculants. This is a continuation of application Ser. No. 603,173 filed Aug. 8, 1975, now abandoned.

Inventors

  • 👤 Jean Neel
  • 👤 Robert Violland

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 10:06
CPC Classifications
C; C07; C07C; C07C233/00; C07C219/00; C07C219/02; C07C219/04; C07C219/08

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 311 words
A process for preparing a highly concentrated aqueous quaternary acrylic ester monomer solution which is directly polymerizable to form hard, transparent, water-soluble, high molecular weight cationic acrylic polymers and which comprises a major content of a salt of a monomeric compound of formula I ##STR2## wherein R represents hydrogen or methyl, A represents an alkylene group containing 1 to 3 carbon atoms, R 1 and R 2 are the same or different and each represents an alkyl group containing 1 to 4 carbon atoms, and R 3 represents a lower alkyl or benzyl group, said process comprising the steps of: (a) reacting an aqueous mixture containing about 50 to about 90% of a compound of formula II ##STR3## wherein R 1 , R 2 , R and A are as defined above, with a quaternizing agent of formula R 3 X, wherein R 3 is as defined above and X is halogen or the --CH 3 SO 4 group at a temperature of between about 10° and about 70° C. whereby a crude aqueous solution of a salt of a compound of formula I is obtained; (b) treating said crude aqueous solution with a water-insoluble solvent in order to obtain a mixture comprising a purified aqueous phase containing the salt of the compound of formula I and being substantially free of impurities of unreacted starting materials and of impurities which induce the formation of water-insoluble polymers, and an organic phase containing the water-insoluble solvent and said impurities; (c) separating the organic base of said mixture from the purified aqueous phase; and, (d) further purifying said purified aqueous phase and recovering therefrom a highly concentrated clear aqueous solution of the salt of the compound of formula I sufficiently free of said impurities and organic solvents said aqueous solution being directly polymerizable into a hard, transparent, water-soluble, high molecular weight cationic acrylic polymer.
Claim 2
Dependent Claim 311 words
A process for preparing a highly concentrated aqueous quaternary acrylic ester monomer solution which is directly polymerizable to form hard, transparent, water-soluble, high molecular weight cationic acrylic polymers and which comprises a major content of a salt of a monomeric compound of formula I ##STR2## wherein R represents hydrogen or methyl, A represents an alkylene group containing 1 to 3 carbon atoms, R 1 and R 2 are the same or different and each represents an alkyl group containing 1 to 4 carbon atoms, and R 3 represents a lower alkyl or benzyl group, said process comprising the steps of: (a) reacting an aqueous mixture containing about 50 to about 90% of a compound of formula II ##STR3## wherein R 1 , R 2 , R and A are as defined above, with a quaternizing agent of formula R 3 X, wherein R 3 is as defined above and X is halogen or the --CH 3 SO 4 group at a temperature of between about 10° and about 70° C. whereby a crude aqueous solution of a salt of a compound of formula I is obtained; (b) treating said crude aqueous solution with a water-insoluble solvent in order to obtain a mixture comprising a purified aqueous phase containing the salt of the compound of formula I and being substantially free of impurities of unreacted starting materials and of impurities which induce the formation of water-insoluble polymers, and an organic phase containing the water-insoluble solvent and said impurities; (c) separating the organic base of said mixture from the purified aqueous phase; and, (d) further purifying said purified aqueous phase and recovering therefrom a highly concentrated clear aqueous solution of the salt of the compound of formula I sufficiently free of said impurities and organic solvents said aqueous solution being directly polymerizable into a hard, transparent, water-soluble, high molecular weight cationic acrylic polymer.
Claim 3
Dependent Claim 12 words
The process as defined in claim 1, wherein R 3 is methyl.
Claim 4
Dependent Claim 20 words
The process as defined in claim 1, wherein A is ethylene and R 1 and R 2 are each methyl.
Claim 5
Dependent Claim 16 words
The process as defined in claim 1, wherein said compound of formula II comprises dimetylaminoethyl methacrylate.
Claim 6
Dependent Claim 18 words
The process as defined in claim 1, wherein the quaternizing agent R 3 X is an alkyl halide.
Claim 7
Dependent Claim 15 words
The process as defined in claim 2, wherein the quaternzing agent is a methyl halide.
Claim 8
Dependent Claim 18 words
The process as defined in claim 5, wherein step (a) comprises introducing said quaternization agent in gaseous form.
Claim 9
Dependent Claim 41 words
The process as defined in claim 1, wherein in step (a) the amount of said quaternization agent in said reaction comprises an excess of 10% by weight relative to the stoichiometric amounts of said agent and said compound of formula II.
Claim 10
Dependent Claim 22 words
The process as defined in claim 1, wherein in step (a) said temperature is between about 15° C. and about 30° C.
Claim 11
Dependent Claim 27 words
The process as defined in claim 1, wherein in step (a) the aqueous mixture contains between about 70% to about 80% of the compound of formula II.
Claim 12
Dependent Claim 28 words
The process as defined in claim 1, wherein step (b) comprises treating the crude aqueous solution with three parts of solvent per ten parts of said aqueous solution.
Claim 13
Dependent Claim 28 words
The process as defined in claim 1, wherein said water-insoluble organic solvent is selected from the group consisting of aliphatic hydrocarbons, aromatic hydrocarbons, ethers, esters and halogenated hydrocarbons.
Claim 14
Dependent Claim 16 words
The process as defined in claim 12, wherein the solvent is an aliphatic or aromatic hydrocarbon.
Claim 15
Dependent Claim 38 words
The process as defined in claim 13, wherein said water-insoluble solvent is selected from the group consisting of benzene, toluene, hexane, cyclohexane, petrolether, trichloroethylene, methylchloroform, xylene, heptane, diethylether, butyl ether, ethyl acetate, carbon tetrachloride, chloroform 1,2-dichloroethane, and monochlorobenzene.
Claim 16
Dependent Claim 14 words
The process as defined in claim 13, wherein the solvent is benzene or hexane.
Claim 17
Dependent Claim 19 words
The process as defined in claim 1, wherein the separating step (c) comprises decantation or centrifugation of said mixture.
Claim 18
Dependent Claim 31 words
The process as defined in claim 1, wherein step (d) comprises the step of evaporating a portion of the purified aqueous phase, whereby any traces of the organic solvent are removed.
Claim 19
Dependent Claim 27 words
The process as defined in claim 17, which comprises evaporating a portion sufficient to obtain a saturated solution of the salt of the compound of formula I.

References Cited (Backward Citations)

US2702774A Cited
US2677679A Cited
US2741568A Cited
US2810720A Cited
US2854472A Cited
US2945876A Cited
US3336358A Cited
US3366663A Cited
US3661880A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-12-24 1983-06-25 1983-12-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-12-24 1987-06-25 1987-12-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-12-24 1991-06-25 1991-12-25 $7700.00 Window Closed / Lapsed

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