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WO1993025595A1 - Compositions polymeres cationiques - Google Patents

Compositions polymeres cationiques Download PDF

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Publication number
WO1993025595A1
WO1993025595A1 PCT/US1993/004823 US9304823W WO9325595A1 WO 1993025595 A1 WO1993025595 A1 WO 1993025595A1 US 9304823 W US9304823 W US 9304823W WO 9325595 A1 WO9325595 A1 WO 9325595A1
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WO
WIPO (PCT)
Prior art keywords
mole
polymer
acid
alkyl
acrylate
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.)
Ceased
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PCT/US1993/004823
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English (en)
Inventor
Jenn S. Shih
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ISP Investments LLC
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ISP Investments LLC
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Filing date
Publication date
Priority claimed from US07/906,163 external-priority patent/US5321110A/en
Application filed by ISP Investments LLC filed Critical ISP Investments LLC
Publication of WO1993025595A1 publication Critical patent/WO1993025595A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • 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
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • 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
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen

Definitions

  • the cationic polymer of the invention comprises 50-99 mole % of a strongly swellable, moderately crosslinked vinyl lactam, e.g. vinylpyrrolidone, and 1-50 mole % of a quaternized a ino alkyl acrylamide, e.g. quaternized dimethylaminopropyl methacrylamide, and including about 0.1-0.8% of a crosslinking agent.
  • Compositions of these cationic polymers effectively thicken both aqueous and non-aqueous solutions at a concentration of 1-10% by weight of the polymer while imparting cationic characteristics to the resulting product.
  • the cationic (quaternized) polymer product has the formula:
  • R is alkylene having from 3 to 8 carbon atoms optionally substituted with lower alkyl
  • R x and R 2 are each independently hydrogen or methyl
  • R 3 and R 4 are each alkylene having from 1 to 18 carbon atoms optionally substituted with alkyl
  • the sum of r and t is one or zero
  • R 5 and R 6 are each independently lower alkyl
  • Z is oxygen or nitrogen; if oxygen, R 2 is absent
  • M is a polymerizable carboxylic acid
  • n has a value of from 1 to 99 mole %
  • m has a value of from 1 to 99 mole %
  • p has a value of from 0 to 98 mole %
  • the sum of m + n + p is 100; preferably, n is 50 to 90 mole %;
  • m is 7 to 25 mole % and p 3 to 25 mole %
  • R 7 sX ⁇ is a quaternizing group, in which R 7 is lower al
  • the powdery quaternized polymers of the invention thus comprise:
  • a strongly swellable, moderately crosslinked vinyl lactam such as vinyl pyrrolidone (VP) or vinyl caprolactam (VC) ; with 0.1-0.8% of a crosslinking agent therein;
  • VP vinyl pyrrolidone
  • VC vinyl caprolactam
  • an amino alkyl acrylamide or acrylate such as dimethylaminopropyl methacrylamide (DMAPMA) or dimethylaminoethyl methacrylate (DMAEMA) ; and, optionally,
  • a polymerizable carboxylic acid such as acrylic acid (AA) or methacrylic acid (MMA) .
  • the powdery cationic polymers of the invention are made by precipitation polymerization in a non-aqueous solvent, particularly, a non-polar organic solvent cyclic or acyclic aliphatic hydrocarbon such as heptane or cyclohexane, an aromatic solvent such as benzene or toluene, an ether such as methyl tertiary butyl ether, or a ketone, such as acetone or methyl ethyl ketone. Both the polymer formation and quaternization steps are carried out in a heterogeneous medium in a non-polar solvent.
  • These powdery quaternized polymers find particular application as cationic thickening agents in cosmetic preparations, such as shampoo and hair conditioner products, and as controlled release or bioadhesive agents.
  • the powdery cationic polymers may be prepared by the steps of:
  • quaternization with a quaternizing agent such as an alkyl halide, a dialkyl sulfate, chloroacetic acid, p-propiolactone, or chloromethyl pyrrolidone
  • Suitable vinyl lactam monomers for use herein have the formula:
  • Representative vinyl lacta s include: N-vinyl pyrrolidone N-vinyl caprolactam N-vinyl piperidone 4-methyl-N-vinyl pyrrolidone 3,5-dimethyl-N-vinyl caprolactam N-vinyl-hexahydro-2-azepinone N-vinyl-octahydro-2-azocinone N-vinyl octahydro-2-azoninone and N-vinyl decahydro-2-aphone.
  • N-vinyl pyrrolidone N-vinyl caprolactam and the ring substituted alkyl derivatives of the N-vinyl caprolactam and N-vinyl pyrrolidone monomers are preferred.
  • N-vinyl-2-pyrrolidone is most preferred.
  • Suitable amino alkyl acrylamide monomers useful in preparing the terpolymers of the present invention include amino alkyl acrylamides and methacrylamides of the general formula:
  • R 1 # R 2 , R 3 , r, R 4 , t, R 5 and R 6 are as defined above .
  • amino alkyl acrylamides which are employed as monomers herein include : N- [ 3- (dimethylamino) propyl] methacrylamide (DMAPMA) N- [ 12- (dimethylamino) dodecyl] ethacrylamide N- [ 18- (dimethylamino) octadecyl] ethacrylamide N- [ 8- (dimethylamino) octyl] methacrylamide N-[7-(dimethylamino) heptyl]acrylamide
  • Amino alkyl acrylate monomers useful in preparing the terpolymers of the invention have the formula:
  • R ⁇ , R 3 , r, R 4 , t, R 5 and R 6 are as defined above.
  • Exemplary amino alkyl acrylates or methacrylates suitably employed in the production of the terpolymers of the present invention include: dimethylaminomethyl acrylate dimethylaminomethyl methacrylate diethylaminomethyl acrylate diethylaminomethyl methacrylate dimethylaminoethyl acrylate dimethylaminoethyl methacrylate (DMAEMA) dimethylaminobutyl acrylate dimethylaminobutyl methacrylate dimethylaminoamyl methacrylate diethylaminoamyl methacrylate dimethylaminohexyl acrylate diethylaminohexyl methacrylate dimethylaminooctyl acrylate dimethylaminooctyl methacrylate diethylaminooctyl methacrylate diethylaminooctyl methacrylate diethylaminooctyl methacrylate dimethylamino
  • Suitable polymerizable carboxylic acid monomers for use herein include: acrylic acid methacrylic acid maleic acid itaconic acid 3-phenyl-2-propenic acid crotonic acid and fumaric acid.
  • Suitable crosslinking agents for use in the invention include such multifunctional compounds as the divinyl ethers of an aliphatic diol, e.g. the divinyl ethers of 1,3-propanediol, 1,4-butanediol, 1,5- pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8- octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11- unidecanediol, and 1,12-dodecanediol; as well as the divinyl ethers of diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, heptaethylene glycol, octaethylene glycol, nonaethylene glycol, decaethylene glycol and further polyalkylene glycols up to a mole
  • crosslinking agents include 1,7- octadiene, 1,9-decadiene, 1,13-tetrade ⁇ adiene, divinylbenzene, N-N , -divinylimidazolidone, and methylene bisacrylamide; acrylates such as polyethylene glycol diacrylate, trimethylolpropane triacrylate, propylene glycol diacrylate; allyl ether derivatives of polyhydric alcohols such as pentaerythritol triallyl ether; or polyhdyric alcohols esterified once or twice with acrylic acid; triallylamine, tetraallylethylene diamine, diallyl phthalate, and the like.
  • Preferred crosslinking agents are the following: N,N'-divinylimidazolidone, pentaerythritol triallyl ether, triallyl-l,3,5-triazine- 2,4,6(lH,3H,5H)-trione and 2,4,6-triallyloxy-l,3,5- triazine.
  • the powdery quaternized polymers of the present invention are conveniently prepared by subjecting a solution of (a) the vinyl lactam, preferably vinyl pyrrolidone, (b) the amino alkyl acrylamide or acrylate monomer, optionally, (c) and the polymerizable carboxylic acid monomer, preferably acrylic acid, and (d) crosslinking agent to conditions conducive to polymerization through double bonds.
  • the reaction can be suitably initiated by the action of free radicals, polymerization proceeding exothermically once initiated.
  • Suitable free radical initiators conveniently employed and suitably utilized in accordance with the production of the copolymers of the present invention include organic and inorganic peroxide and perester compounds e.g., hydrogen peroxide, lauryl peroxide, decanoyl peroxide, di-tert-butyl peroxide, tert-butyl peroxypivalate, etc., aliphatic azo compounds, e.g., azobisisobutyronitrile, as well as other free radical initiators well known in the polymerization art.
  • organic and inorganic peroxide and perester compounds e.g., hydrogen peroxide, lauryl peroxide, decanoyl peroxide, di-tert-butyl peroxide, tert-butyl peroxypivalate, etc.
  • aliphatic azo compounds e.g., azobisisobutyronitrile
  • the polymerization reaction of the present invention takes place in the presence of a solvent.
  • precipitation polymerization is employed to provide the quaternized polymer in powder form.
  • Suitable solvents for this use are non-polar organic solvents, preferably cyclic or acyclic, such as aliphatic hydrocarbons, such as hexane, heptane and cyclohexane. Heptane and cyclohexane are preferred. Both the formation of the polymer and the quaternization of the powdery polymer to form a powdery quaternized polymer, are carried out heterogeneously.
  • the precipitation polymerization reaction is effected at a temperature between about 40°C. and about 130°C. under from about 14 to about 50 psia. for a period of from about 1 to about 20 hours.
  • a temperature between about 40°C. and about 130°C. under from about 14 to about 50 psia. for a period of from about 1 to about 20 hours.
  • the polymerization reaction is preferably carried out in the absence of free oxygen, conveniently under a blanket of an inert gas, such as nitrogen, argon or the like, and at atmospheric pressure.
  • the polymers of the invention can be made by precipitation polymerization within the complete compositional range of monomer components. Accordingly, the polymers can be formed from 1-99% by weight of each of the monomer components; preferably (a) 50 to 90%; (b) 10 to 50%; and (c) 0-15%.
  • the polymer is produced within a period of a few hours, e.g. less than about 10 hours.
  • the feeding rates of the VP and DMAPMA monomers suitably is about 0.1 ml/min/kg solvent to 1.0 ml/min/kg solvent, preferably 0.4-0.7 ml/min/kg solvent; and the polymeriaable carboxylic acid and crosslinking agent are added during the same period of time.
  • the present cationic polymeric products are particularly useful as viscosity builders for cosmetic creams and lotions as well as for such hair treatment compositions to provide body and retentative moisturizing.
  • the amount of polymeric product used can range between about 0.05 weight % and about 8 weight %, based on total formulation. Usually not more than 4% is required to achieve the above desirable affects.
  • the present powdery quaternized polymer or polymer mixture may be conveniently added to the cosmetic formulations as the powder itself, or as an aqueous or non-aqueous solution containing from about 1% to about 10% of polymer.
  • the strongly swellable, moderately crosslinked polymer powders of the invention in suitable aqueous or non-aqueous solution are characterized by its unique gel volume and viscosity, which properties enable the polymer to thicken aqueous and non-aqueous solutions effectively.
  • Gel volume is a measure of the swelling property of the crosslinked polymer and is defined as the equilibrium aqueous swelling volume of polymer per unit weight, and is expressed in the units of ml/g. Gel volume is determined by first adding 1 g. of the polymer to a suitable graduated cylinder filled with water. This mixture then is shaken and allowed to stand at room temperature for 3 days. The volume of the gel which is produced in water is measured and taken as the gel volume. Similarly, the gel volume concept can be applied to non-aqueous systems.
  • the viscosity of the polymer is defined by its Brookfield viscosity in cps, which is determined upon a 4% aqueous solution of the polymer at 25°C. by a standard analytical procedure using Model RTV and Spindle No. 4.
  • Figure 1 is a graphical representation of Brookfield viscosity and gel volume vs. at a concentration of 4% by weight crosslinker for an aqueous cationic polymer composition of a cationic polymer composition of 79 weight % of strongly swellable, moderately crosslinked vinylpyrrolidone (VP) crosslinked with triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TATT) , and 19 weight % of quaternized dimethylaminopropyl methacrylamide (DMAPMAA) , and 2 weight % acrylic acid, at a 4% by weight level-.
  • VP moderately crosslinked vinylpyrrolidone
  • TATT triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
  • DMAPMAA quaternized dimethylaminopropyl methacrylamide
  • Figure 2 is a graphical representation of Brookfield viscosity vs. aqueous concentration for the cationic polymer composition of Figure 1 at a 0.45% TATT level.
  • Figure 1 there is shown the Brookfield viscosity and gel volume parameters vs. % crosslinker for an aqueous solution of the cationic polymers of the invention.
  • the hydrated polymer exhibit a high gel volume and a high viscosity. With increasing crosslinking density in the polymer, the gel volume decreases and viscosity increases and then decreases, passing through a maximum.
  • an effective thickener product is provided by including crosslinker in the reaction mixture at a suitable concentration of about 0.1 to 0.8% by weight, based upon VP, preferably about 0.2 to 0.6%.
  • the crosslinked polymer product exhibits a gel volume of about 50 to 150 ml/g of polymer and a Brookfield viscosity of at least 10,000 cps.
  • the gel volume is about 70 to 90 ml/g of polymer and its Brookfield viscosity is at least 23,000 cps.
  • the optimal amount crosslinker present in the reaction mixture of 0.25% the polymer exhibits a gel volume of about 85 ml/g of polymer and a Brookfield viscosity of about 57,000 cps.
  • Figure 2 shows the effect of polymer conentration in aqueous solution upon Brookfield viscosity at a 0.45% crosslinker level.
  • the polymer concentration is 1-10% by weight of the solution preferably about 2-8%. The viscosity increases dramatically above 4%.
  • the residual VP monomer content of the polymers obtained herein is less than about 0.1% by weight.
  • the formation of a gel mass during polymerization may trap considerable amounts of VP monomer in the polymeric gel network.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention se rapporte à des compositions polymères cationiques comprenant un polymère cationique composé d'un lactame vinylique modérément réticulé et fortement gonflable, tel que vinylpyrrolidone, ainsi qu'un acrylate ou un acrylamido d'amidoalkyle rendu quaternaire, tel que du méthacrylate de diméthylaminoéthyle ou du méthacrylamide de diméthylaminopropyle rendu quaternaire, et comprenant éventuellement un acide carboxylique polymérisable tel que l'acide acrylique ou l'acide méthacrylique, qui contient de 0,1 à 0,8 % d'un agent de réticulation. Ces compositions polymères, présentes en une concentration de 1 à 10 % en poids dans un milieu aqueux ou non aqueux, produisent un épaississement efficace tout en conférant des caractéristiques cationiques à la solution obtenue.
PCT/US1993/004823 1992-06-17 1993-05-20 Compositions polymeres cationiques Ceased WO1993025595A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US89996592A 1992-06-17 1992-06-17
US899,965 1992-06-17
US07/906,163 US5321110A (en) 1992-06-29 1992-06-29 Cationic polymer compositions
US906,163 1992-06-29

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995034588A1 (fr) * 1994-06-10 1995-12-21 Geltex Pharmaceuticals, Inc. Polymeres reticules utilises pour eliminer les sels biliaires d'un patient
US5703188A (en) * 1993-06-02 1997-12-30 Geltex Pharmaceuticals, Inc. Process for removing bile salts from a patient and compositions therefor
EP1188571A1 (fr) * 2000-09-19 2002-03-20 Westvaco Corporation Procédé d'impression à jet d'encre
US6383612B1 (en) 1998-06-19 2002-05-07 3M Innovative Properties Company Ink-drying agents for inkjet receptor media
US6514599B1 (en) 1999-04-16 2003-02-04 3M Innovative Properties Company Inkjet receptor medium having a multi-staged ink migration inhibitor and method of making and using same
US6537650B1 (en) 1998-06-19 2003-03-25 3M Innovative Properties Company Inkjet receptor medium having ink migration inhibitor and method of making and using same
US6632510B1 (en) 1997-07-14 2003-10-14 3M Innovative Properties Company Microporous inkjet receptors containing both a pigment management system and a fluid management system
US6677007B1 (en) 1999-02-12 2004-01-13 3M Innovative Properties Company Image receptor medium and method of making and using same
US6682725B1 (en) 1997-07-24 2004-01-27 Basf Aktiengesellschaft High molecular weight mass cationic copolymers
US6703112B1 (en) 1998-06-19 2004-03-09 3M Innovative Properties Company Organometallic salts for inkjet receptor media
WO2006097514A1 (fr) * 2005-03-18 2006-09-21 Basf Aktiengesellschaft Polymeres cationiques utilises comme epaississants de compositions aqueuses et alcooliques
US7422735B1 (en) 1999-06-29 2008-09-09 Basf Aktiengesellschaft Use of crosslinked cationic polymers in skin cosmetic and dermatological preparations
WO2009010385A1 (fr) * 2007-07-17 2009-01-22 Basf Se Copolymères à charge cationique élevée, à base de monomères azotés quaternisés
US8247507B2 (en) 2006-09-21 2012-08-21 Basf Se Cationic polymers as thickeners for aqueous and alcoholic compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910862A (en) * 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
US3933766A (en) * 1972-11-11 1976-01-20 Basf Aktiengesellschaft Manufacture of insoluble and only sparingly swellable poly-N-vinylpyrrolidone-2 or copolymers of N-vinylpyrrolidone with other N-vinyllactams
US5153289A (en) * 1985-01-02 1992-10-06 Exxon Research And Engineering Company Betaine copolymers-viscosifiers for water and brine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910862A (en) * 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
US3933766A (en) * 1972-11-11 1976-01-20 Basf Aktiengesellschaft Manufacture of insoluble and only sparingly swellable poly-N-vinylpyrrolidone-2 or copolymers of N-vinylpyrrolidone with other N-vinyllactams
US5153289A (en) * 1985-01-02 1992-10-06 Exxon Research And Engineering Company Betaine copolymers-viscosifiers for water and brine

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5624963A (en) * 1993-06-02 1997-04-29 Geltex Pharmaceuticals, Inc. Process for removing bile salts from a patient and compositions therefor
US5703188A (en) * 1993-06-02 1997-12-30 Geltex Pharmaceuticals, Inc. Process for removing bile salts from a patient and compositions therefor
US5840766A (en) * 1993-06-02 1998-11-24 Geltex Pharmaceuticals, Inc. Process for removing bile salts from a patient and compositions therefor
US6060517A (en) * 1993-06-02 2000-05-09 Geltex Pharmaceuticals, Inc. Process for removing bile salts from a patient and compositions therefor
WO1995034588A1 (fr) * 1994-06-10 1995-12-21 Geltex Pharmaceuticals, Inc. Polymeres reticules utilises pour eliminer les sels biliaires d'un patient
US6632510B1 (en) 1997-07-14 2003-10-14 3M Innovative Properties Company Microporous inkjet receptors containing both a pigment management system and a fluid management system
CN1330287C (zh) * 1997-07-24 2007-08-08 Basf公司 高分子量阳离子共聚物
US6682725B1 (en) 1997-07-24 2004-01-27 Basf Aktiengesellschaft High molecular weight mass cationic copolymers
US6537650B1 (en) 1998-06-19 2003-03-25 3M Innovative Properties Company Inkjet receptor medium having ink migration inhibitor and method of making and using same
US6383612B1 (en) 1998-06-19 2002-05-07 3M Innovative Properties Company Ink-drying agents for inkjet receptor media
US6703112B1 (en) 1998-06-19 2004-03-09 3M Innovative Properties Company Organometallic salts for inkjet receptor media
US6677007B1 (en) 1999-02-12 2004-01-13 3M Innovative Properties Company Image receptor medium and method of making and using same
US6514599B1 (en) 1999-04-16 2003-02-04 3M Innovative Properties Company Inkjet receptor medium having a multi-staged ink migration inhibitor and method of making and using same
US7422735B1 (en) 1999-06-29 2008-09-09 Basf Aktiengesellschaft Use of crosslinked cationic polymers in skin cosmetic and dermatological preparations
EP1188571A1 (fr) * 2000-09-19 2002-03-20 Westvaco Corporation Procédé d'impression à jet d'encre
WO2006097514A1 (fr) * 2005-03-18 2006-09-21 Basf Aktiengesellschaft Polymeres cationiques utilises comme epaississants de compositions aqueuses et alcooliques
US8247507B2 (en) 2006-09-21 2012-08-21 Basf Se Cationic polymers as thickeners for aqueous and alcoholic compositions
WO2009010385A1 (fr) * 2007-07-17 2009-01-22 Basf Se Copolymères à charge cationique élevée, à base de monomères azotés quaternisés
US8623343B2 (en) 2007-07-17 2014-01-07 Basf Se Highly cationic copolymers based on quaternized nitrogen-containing monomers

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