CA2560287A1 - Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer - Google Patents
Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer Download PDFInfo
- Publication number
- CA2560287A1 CA2560287A1 CA002560287A CA2560287A CA2560287A1 CA 2560287 A1 CA2560287 A1 CA 2560287A1 CA 002560287 A CA002560287 A CA 002560287A CA 2560287 A CA2560287 A CA 2560287A CA 2560287 A1 CA2560287 A1 CA 2560287A1
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- vinyl
- acryloxy
- methacryloxy
- ammonium chloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
- Y10T442/69—Autogenously bonded nonwoven fabric
Abstract
A method of making an ion triggerable cationic polymer by solution copolymerizing one or more vinyl-functional cationic monomers, one or more water insoluble or hydrophobic vinyl monomers with alkyl side chains up to 4 carbons long, and, optionally, a minor amount of one ore more vinyl monomers with linear or branched alkyl groups longer than 4 carbons, alkyl hydroxy, polyoxyalkylene, or other functional groups. The solution polymerization is accomplished by free radical polymerization in a mixture of acetone and water.
Claims (24)
1. A method of solution polymerizing an ion-triggerable cationic polymer comprising the steps of:
A. preparing a mixed solvent solution of water and acetone;
B. heating the solvent solution;
C. mixing with said solvent solution 1) one or more vinyl-functional cationic monomers, 2) one or more hydrophobic vinyl monomers having alkyl side chains of 1 to 4 carbon atoms, 3) optionally about 0% to 30 mole % of one or more other vinyl monomers with linear or branched alkyl groups longer than 4 carbons, alkyl hydroxy, polyoxyalkylene, or other functional group, and 4) a free radical initiator, to form a reaction mixture;
D. heating the reaction mixture for a sufficient amount of time to polymerize the monomers and provide the ion-triggerable cationic polymer;
E. after polymerization, performing the following steps in any sequence, including simultaneously, adding water to said reaction mixture to provide an aqueous dispersion of said ion-triggerable cationic polymer, and F. removing substantially all of the acetone from said reaction mixture.
A. preparing a mixed solvent solution of water and acetone;
B. heating the solvent solution;
C. mixing with said solvent solution 1) one or more vinyl-functional cationic monomers, 2) one or more hydrophobic vinyl monomers having alkyl side chains of 1 to 4 carbon atoms, 3) optionally about 0% to 30 mole % of one or more other vinyl monomers with linear or branched alkyl groups longer than 4 carbons, alkyl hydroxy, polyoxyalkylene, or other functional group, and 4) a free radical initiator, to form a reaction mixture;
D. heating the reaction mixture for a sufficient amount of time to polymerize the monomers and provide the ion-triggerable cationic polymer;
E. after polymerization, performing the following steps in any sequence, including simultaneously, adding water to said reaction mixture to provide an aqueous dispersion of said ion-triggerable cationic polymer, and F. removing substantially all of the acetone from said reaction mixture.
2. The method of claim 1 further including the step of removing oxygen from said solvent solution prior to forming said reaction mixture.
3. The method of claim 1 wherein the solvent solution is comprised of about 50% to about 90% by weight acetone and about 10% to about 50% by weight water.
4. The method of claim 1 wherein the solvent solution is comprised of 75% by weight acetone and 25% by weight water.
5. The method of claim 1 wherein the step of heating the solvent solution comprises heating the solvent solution to reflux prior to adding the vinyl-functional cationic monomer, the hydrophobic vinyl monomer, and the free radical initiator thereto to form said reaction mixture.
6. The method of claim 1 wherein said one or more vinyl-functional cationic monomers is added as an aqueous solution to said solvent solution.
7. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(acryloxy)ethyl] dimethyl ammonium chloride, [2-(methacryloxy)ethyl] dimethyl ammonium chloride, [2-(acryloxy)ethyl] trimethyl ammonium chloride, [2-(methyacryloxy)ethyl] trimethyl ammonium chloride, (3-acrylamidopropyl) trimethyl ammonium chloride, N,N-diallyldimethyl ammonium chloride, [2-(acryloxy)ethyl] dimethylbenzyl ammonium chloride, and [2-(methacryloxy)ethyl] dimethylbenzyl ammonium chloride.
8. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from precursor monomers selected from vinylpyridine, dimethylaminoethyl acrylate and dimethylaminoethyl methacrylate followed by quaternization of the polymer.
9. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(acryloxy)ethyl] dimethyl ammonium chloride, [2-(acryloxy)ethyl] dimethyl ammonium bromide, [2-(acryloxy)ethyl] dimethyl ammonium iodide, and [2-(acryloxy)ethyl] dimethyl ammonium methyl sulfate.
10. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(methacryloxy)ethyl) dimethyl ammonium chloride, [2-(methacryloxy)ethyl) dimethyl ammonium bromide, [2-(methacryloxy)ethyl) dimethyl ammonium iodide, and [2-(methacryloxy)ethyl) dimethyl ammonium methyl sulfate.
11. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(acryloxy)ethyl] trimethyl ammonium chloride, [2-(acryloxy)ethyl] trimethyl ammonium bromide, [2-(acryloxy)ethyl] trimethyl ammonium iodide, and [2-(acryloxy)ethyl] trimethyl ammonium,methyl sulfate.
12. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(methacryloxy)ethyl] trimethyl ammonium chloride, [2-(methacryloxy)ethyl] trimethyl ammonium bromide, [2-(methacryloxy)ethyl]
trimethyl ammonium iodide, and [2-(methacryloxy)ethyl] trimethyl ammonium methyl sulfate.
trimethyl ammonium iodide, and [2-(methacryloxy)ethyl] trimethyl ammonium methyl sulfate.
13. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from (3-acrylamidopropyl) trimethyl ammonium chloride, (3-acrylamidopropyl) trimethyl ammonium bromide, (3-acrylamidopropyl) trimethyl ammonium iodide, and (3-acrylamidopropyl) trimethyl ammonium methyl sulfate.
14. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from N,N-diallyldimethyl ammonium chloride, N,N-diallyldimethyl ammonium bromide, N,N-diallyldimethyl ammonium iodide, and N,N-diallyldimethyl ammonium methyl sulfate.
15. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(acryloxy)ethyl] dimethylbenzyl ammonium chloride, [2-(acryloxy)ethyl] dimethylbenzyl ammonium bromide, [2-(acryloxy)ethyl]
dimethylbenzyl ammonium iodide, and [2-(acryloxy)ethyl] dimethylbenzyl ammonium methyl sulfate.
dimethylbenzyl ammonium iodide, and [2-(acryloxy)ethyl] dimethylbenzyl ammonium methyl sulfate.
I6. The method of claim 1 wherein the vinyl-functional cationic monomer is selected from [2-(methacryloxy)ethyl] dimethylbenzyl ammonium chloride, [2-(methacryloxy)ethyl] dimethylbenzyl ammonium bromide, [2-(methacryloxy)ethyl]
dimethylbenzyl ammonium iodide; and [2-(methacryloxy)ethyl] dimethylbenzyl ammonium methyl sulfate.
dimethylbenzyl ammonium iodide; and [2-(methacryloxy)ethyl] dimethylbenzyl ammonium methyl sulfate.
17. The method of claim 1 wherein the hydrophobic vinyl monomer is selected from branched or linear alkyl vinyl ethers, vinyl esters, acrylamides, and acrylates.
18. The method of claim 1 wherein the hydrophobic, vinyl monomer is methyl acrylate.
19. The method of claim 1 wherein the vinyl-functional cationic polymer is [2-(acryloxy)ethyl] trimethyl ammonium chloride.
20. The method of claim 1 wherein the hydrophobic vinyl monomer is selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate and butyl acrylate.
21. The method of claim 1 wherein the free radical initiator is an azo initiator selected from the group consisting of 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(N,N'-dimethyleneisobutylamidine).
22. The method of claim 1 wherein the free radical initiator is a peroxide initiator selected from the group consisting of di(n-propyl)peroxydicarbonate, di(sec-butyl)peroxydicarbonate, di(2-ethylhexyl)peroxydicarbonate, t-amyl peroxyneodecanoate, t-butyl peroxyneodecanoate, t-amyl peroxypivalate, and t-butyl peroxypivalate.
23. The method of claim 1 further including preparing the mixed solvent solution of step A using the acetone removed after polymerization from step E, and thereafter repeating steps B through F.
24. The method of claim 23 further including adding an amount of make-up acetone to the acetone from step E when preparing the mixed solvent solution.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/803,306 | 2004-03-18 | ||
| US10/803,306 US7592391B2 (en) | 2004-03-18 | 2004-03-18 | Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer |
| PCT/US2005/007660 WO2005090422A1 (en) | 2004-03-18 | 2005-03-09 | Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2560287A1 true CA2560287A1 (en) | 2005-09-29 |
| CA2560287C CA2560287C (en) | 2012-11-27 |
Family
ID=34962136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2560287 Active CA2560287C (en) | 2004-03-18 | 2005-03-09 | Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7592391B2 (en) |
| EP (1) | EP1756182B1 (en) |
| JP (1) | JP4988549B2 (en) |
| CN (1) | CN100556923C (en) |
| AT (1) | ATE423149T1 (en) |
| AU (1) | AU2005223753B2 (en) |
| BR (1) | BRPI0508920B1 (en) |
| CA (1) | CA2560287C (en) |
| DE (1) | DE602005012821D1 (en) |
| ES (1) | ES2321959T3 (en) |
| MX (1) | MXPA06010841A (en) |
| WO (1) | WO2005090422A1 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7619033B2 (en) * | 2004-03-18 | 2009-11-17 | Bostik, Inc. | Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer |
| US7357909B2 (en) * | 2006-06-28 | 2008-04-15 | Lyondell Chemical Technology, L.P. | Process for producing hydrogen peroxide |
| MY162376A (en) | 2009-08-05 | 2017-06-15 | Shell Int Research | Method for monitoring a well |
| PL2845949T3 (en) | 2009-08-05 | 2023-09-11 | International Paper Company | Process for applying composition containing a cationic trivalent metal and debonder and fluff pulp sheet made from same |
| ES2529104T3 (en) * | 2009-08-05 | 2015-02-16 | International Paper Company | Additive for dried sheets of spongy paper pulp |
| US8465624B2 (en) | 2010-07-20 | 2013-06-18 | International Paper Company | Composition containing a multivalent cationic metal and amine-containing anti-static agent and methods of making and using |
| US8871054B2 (en) | 2010-07-22 | 2014-10-28 | International Paper Company | Process for preparing fluff pulp sheet with cationic dye and debonder surfactant |
| US9394637B2 (en) | 2012-12-13 | 2016-07-19 | Jacob Holm & Sons Ag | Method for production of a hydroentangled airlaid web and products obtained therefrom |
| KR102192163B1 (en) * | 2017-09-12 | 2020-12-16 | 다케모토 유시 가부시키 가이샤 | Dispersion retention agent for hydraulic compositions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60220137A (en) * | 1984-04-18 | 1985-11-02 | Kao Corp | Aqueous dispersion |
| JP3162696B2 (en) * | 1989-09-06 | 2001-05-08 | ライオン株式会社 | Water-soluble, salt-sensitive polymer |
| JP3148307B2 (en) * | 1991-11-07 | 2001-03-19 | ライオン株式会社 | Salt-sensitive polymer |
| US5384189A (en) * | 1993-01-27 | 1995-01-24 | Lion Corporation | Water-decomposable non-woven fabric |
| US6423804B1 (en) * | 1998-12-31 | 2002-07-23 | Kimberly-Clark Worldwide, Inc. | Ion-sensitive hard water dispersible polymers and applications therefor |
| US6653406B1 (en) * | 2000-05-04 | 2003-11-25 | Kimberly Clark Worldwide, Inc. | Ion-sensitive, water-dispersible polymers, a method of making same and items using same |
| US20030027470A1 (en) * | 2001-03-22 | 2003-02-06 | Yihua Chang | Water-dispersible, cationic polymers, a method of making same and items using same |
| US20030032352A1 (en) * | 2001-03-22 | 2003-02-13 | Yihua Chang | Water-dispersible, cationic polymers, a method of making same and items using same |
| US6828014B2 (en) | 2001-03-22 | 2004-12-07 | Kimberly-Clark Worldwide, Inc. | Water-dispersible, cationic polymers, a method of making same and items using same |
| US20040058600A1 (en) * | 2002-09-20 | 2004-03-25 | Bunyard W. Clayton | Water-dispersible, cationic polymers, a method of making same and items using same |
| US7157389B2 (en) * | 2002-09-20 | 2007-01-02 | Kimberly-Clark Worldwide, Inc. | Ion triggerable, cationic polymers, a method of making same and items using same |
-
2004
- 2004-03-18 US US10/803,306 patent/US7592391B2/en active Active
-
2005
- 2005-03-09 DE DE200560012821 patent/DE602005012821D1/en active Active
- 2005-03-09 WO PCT/US2005/007660 patent/WO2005090422A1/en active Application Filing
- 2005-03-09 BR BRPI0508920A patent/BRPI0508920B1/en active IP Right Grant
- 2005-03-09 JP JP2007503957A patent/JP4988549B2/en active Active
- 2005-03-09 ES ES05725046T patent/ES2321959T3/en active Active
- 2005-03-09 MX MXPA06010841A patent/MXPA06010841A/en active IP Right Grant
- 2005-03-09 CN CNB200580015871XA patent/CN100556923C/en active Active
- 2005-03-09 AU AU2005223753A patent/AU2005223753B2/en active Active
- 2005-03-09 AT AT05725046T patent/ATE423149T1/en not_active IP Right Cessation
- 2005-03-09 EP EP20050725046 patent/EP1756182B1/en active Active
- 2005-03-09 CA CA 2560287 patent/CA2560287C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06010841A (en) | 2006-12-15 |
| CN1954001A (en) | 2007-04-25 |
| BRPI0508920A (en) | 2007-11-20 |
| JP4988549B2 (en) | 2012-08-01 |
| AU2005223753A1 (en) | 2005-09-29 |
| EP1756182B1 (en) | 2009-02-18 |
| ES2321959T3 (en) | 2009-06-15 |
| ATE423149T1 (en) | 2009-03-15 |
| DE602005012821D1 (en) | 2009-04-02 |
| WO2005090422A1 (en) | 2005-09-29 |
| CA2560287C (en) | 2012-11-27 |
| EP1756182A1 (en) | 2007-02-28 |
| AU2005223753B2 (en) | 2011-06-23 |
| BRPI0508920B1 (en) | 2015-10-20 |
| US7592391B2 (en) | 2009-09-22 |
| JP2007529601A (en) | 2007-10-25 |
| CN100556923C (en) | 2009-11-04 |
| US20050209396A1 (en) | 2005-09-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2560287A1 (en) | Process for preparing an aqueous dispersion of a quaternary ammonium salt containing vinyl copolymer | |
| JP2009509004A5 (en) | ||
| Save et al. | Controlled radical polymerization in aqueous dispersed media | |
| Jones et al. | Rapid synthesis of well-defined polyacrylamide by aqueous Cu (0)-mediated reversible-deactivation radical polymerization | |
| EP3599258B1 (en) | Method to produce colorless, high porosity, transparent polymer aerogels | |
| JP2005534799A (en) | Aqueous polymer dispersions, their production and use, in particular anticorrosive coatings | |
| CA2494805A1 (en) | High molecular weight cationic polymers obtained by post-polymerisation crosslinking reaction | |
| US20160347872A1 (en) | Living radical polymerization catalyst, and polymer production method using same | |
| WO2008003729A3 (en) | Process of free-radical polymerization in aqueous dispersion for the preparation of polymers | |
| CN103741469A (en) | Antibiotic finishing agent | |
| CN103833888A (en) | Preparation method of aqueous fluorine-modified phosphorus-containing acrylate emulsion | |
| JP2013544318A5 (en) | ||
| US20210253770A1 (en) | High melt index thermoplastic elastomer and preparation method therefor | |
| US9884933B2 (en) | Comb copolymer and process for the preparation thereof | |
| EP1881998A1 (en) | Dispersant for manufacturing vinyl chloride resin and method of manufacturing vinyl chloride resin using the same | |
| EP3296333B1 (en) | Alkenyl ether-vinyl ester copolymer | |
| US9410005B2 (en) | Polymer, preparation method thereof, composition and film comprising the same | |
| JPH11147914A (en) | Polyvinyl alcohol resin | |
| JP6676571B2 (en) | Reversible addition-fragmentation chain transfer polymerization method and acrylic block copolymer | |
| JP2016199647A (en) | Polymer gel and method for producing the same | |
| CN109503783B (en) | Terminal siloxane modified polyacrylate block copolymer and preparation method thereof | |
| EP2017292A4 (en) | Process for production of fluorine-containing polymers | |
| KR100674373B1 (en) | Dispersing agent for vinyl polymers suspension polymerization and manufacturing method thereof | |
| JP4978946B2 (en) | Ionic polymer for GPC standard | |
| DE60207250D1 (en) | PROCESS FOR PREPARING AQUEOUS POLYMER DISPERSIONS |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |