WO1999016798A1 - Verfahren zur herstellung von anionisch modifizierten polymerisaten von alkyl-1-vinylimidazolen - Google Patents
Verfahren zur herstellung von anionisch modifizierten polymerisaten von alkyl-1-vinylimidazolen Download PDFInfo
- Publication number
- WO1999016798A1 WO1999016798A1 PCT/EP1998/005944 EP9805944W WO9916798A1 WO 1999016798 A1 WO1999016798 A1 WO 1999016798A1 EP 9805944 W EP9805944 W EP 9805944W WO 9916798 A1 WO9916798 A1 WO 9916798A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- vinylimidazole
- mixtures
- mol
- monomers
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3776—Heterocyclic compounds, e.g. lactam
-
- 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
- C08F26/00—Homopolymers and 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
- C08F26/06—Homopolymers and 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/378—(Co)polymerised monomers containing sulfur, e.g. sulfonate
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3784—(Co)polymerised monomers containing phosphorus
Definitions
- the invention relates to a process for the preparation of anionically modified polymers of alkyl -1-vinylimidazoles by radical polymerization of alkyl -1-vinylimidazoles with anionic monoethylenically unsaturated monomers and optionally other copolymerizable monomers in an aqueous solvent.
- WO-A-95/15345 describes polymers of alkyl-1-vinylimidazoles, processes for their preparation by polymerizing alkyl-1-vinylimidazoles, if appropriate in the presence of other monomers in water, at least one C 1 -C 4 -alcohol or their mixtures in the presence of polymerization regulators and the use of the polymers as a detergent additive are known.
- Alkyl - 1-vinylimidazoles can also be copolymerized with carboxylic acids such as acrylic acid or maleic acid to give clear aqueous solutions.
- Polymerization regulators which contain sulfur in bound form are used in amounts of up to 15, preferably 0.5 to 10% by weight, based on the monomers used in the polymerization. If higher amounts of regulators are used in the polymerization, the properties of the polymers are changed. In addition, by-products are formed during the polymerization, which can cause odor problems.
- the object of the invention is to provide a process for the preparation of alkyl -1-vinylimidazoles which is improved compared to the abovementioned processes.
- the object is achieved according to the invention with a process for the preparation of anionically modified polymers of alkyl-1-vinylimidazoles by radical polymerization of Alkyl-1-vinylimidazoles with anionic monoethylenically unsaturated monomers and optionally other copolymerizable monomers in an aqueous solvent if the copolymerization is carried out with the exclusion of polymerization regulators.
- monomer mixtures are polymerized in the process according to the invention.
- Suitable monomers of group (a) are all 1-vinylimidazoles substituted with at least one alkyl group. For example, they can be characterized using the following formula:
- R, R 1 , R 2 may be the same or different and for H
- Ci Ci to C 5 alkyl or C 5 to Cio-cycloalkyl, where at least one substituent R, R 1 or R 2 is one
- Ci Ci to C 25 alkyl group or C 5 to C ⁇ 0 cycloalkyl group.
- the substituents R 1 and R 2 are preferably H, CH 3 and C 2 H 5 .
- Monomers of group (a) are, for example, 2-methyl-1-vinylimidazole, 2-ethyl-1-vinylimidazole, 2-propyl-1-vinylimidazole, 2-butyl-1-vinylimidazole, 2, 4 -dimethyl-1-vinylimidazole, 2, 5 -dimethyl-1-vinylimidazole, 2-ethyl-4-methyl-1-vinylimidazole, 2-ethyl-5-methyl-1-vinylimidazole, 2, 4, 5 -trimethyl-1-vinylimidazole, 4, 5 - Diethyl -2-methyl-1-vinylimidazole, 4-methyl-1-vinyl-imidazole, 4-ethyl-1-vinylimidazole, 4, 5 -dimethyl-1-vinylimidazole, 5-methyl-1-vinylimidazole or 2, 4, 5-triethyl-1-vinylimidazole.
- Mixtures of the monomers mentioned can also be used in any ratio.
- 2-methyl-1-vinyl-imidazole, 2-ethyl-1-vinylimidazole, 2-ethyl-4-methyl-1-vinyl-imidazole or 4-methyl-1-vinylimidazole is used as the monomer of group (a) .
- 2-Methyl-1-vinylimidazole is very particularly preferred.
- the polymers contain the monomers of group (a), for example in amounts of from 5 to 99.5, preferably from 20 to 75 mol, copolymerized.
- the monomers of group (b) contain acid groups in free or neutralized form.
- Suitable monomers containing acid groups are, for example, all monomers containing carboxyl, sulfonic acid or phosphonic acid groups. Examples of such compounds are acrylic acid, methacrylic acid, ethacrylic acid,
- Those monomers which contain more than one acid group can also be used in the form of their anhydrides, but the corresponding carboxylic acid is formed from them immediately when they are introduced into the aqueous poly
- the monomers containing acid groups can be used in the polymerization either in the form of the free acid groups or in partially or completely neutralized form with bases.
- bases are, for example, alkali metal bases such as alkali metal hydroxides and alkali metal carbonates, for example sodium hydroxide solution, potassium hydroxide solutions, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, ammonia and organic amines such as ethanolamine, diethanolamine, triethanolamine, pyridine and piperazine, and also amidines or mixtures of the bases mentioned.
- Suitable amines are triisopropanolamine, 2-amino-2-methyl-propanol, alkanediol amines with 2 to 4 carbon atoms in the alkanediol radical, such as 2-amino-2-methyl-1, 3-propanediol or 2-amino-2-ethyl -1,3-propanediol, alkane polyolamines such as tetrahydroxypropylene ethylenediamine, alkylamines such as di (2-ethylhexyl) amine, triamylamine or dodecylamine and amino ethers such as morpholine.
- the bases can be added before, during or after the polymerization in order to neutralize the monomers containing acid groups. Superstoichiometric amounts of bases can also be used in the neutralization of the monomers.
- Monomers of group (c) are 1-vinylpyrrolidone, 1-vinylcaprolactam, 1-vinyltriazole, 1-vinylimidazole and 1-vinyloxazolidinone and mixtures of the compounds mentioned with one another. Of the monomers of group (c), 1-vinylpyrrolidone and / or 1-vinylimidazole are preferably used.
- the monomers of group (c), if they are used in the polymerization, are present in the monomer mixture in amounts of up to 89.5 mol%.
- the polymerization of the monomers (a) and (b) and optionally (c) can additionally be carried out, if appropriate, in the presence of monomers of group (d).
- monomers of group (d) These are monomers which contain at least 2 monoethylenically unsaturated double bonds in the molecule. Compounds of this type are usually used as crosslinking agents in polymerization reactions.
- Suitable crosslinkers of this type are, for example, diacrylates or dimethylacrylates of at least dihydric saturated alcohols, for example ethylene glycol diacrylate, ethylene glycol dimethyl acrylate, 1,2-propylene glycol diacrylate, 1,2-propylene glycol dimethacrylate, butanediol -1,4-diacrylate, 4-butanediol, 4-butanediol dimethacrylate, hexanediol diacrylate, hexanediol dimethacrylate, neopentylglycol diacrylate, neopentylglycol dimethacrylate, 3-methylpentanediol diacrylate and 3-methylpentanediol dimethacrylate.
- diacrylates or dimethylacrylates of at least dihydric saturated alcohols for example ethylene glycol diacrylate, ethylene glycol dimethyl acrylate, 1,2-propylene glycol diacrylate, 1,
- the acrylic acid and methacrylic acid esters of alcohols with more than 2 OH groups can also be used as crosslinking agents, for example trimethylol propane triacrylate or trimethylol propane trimethacrylate.
- Another class of crosslinking agents are diacrylates or dimethacrylates of polyethylene glycols or polypropylene glycols with molecular weights of 200 to 9000 each.
- Polyethylene glycols or polypropylene glycols which are used for the production of the diacrylates or dimethacrylates preferably have a molecular weight of 400 to 2000 in each case
- the homopolymers of ethylene oxide or propylene oxide can also be used in block copolymers of ethylene oxide and propylene oxide or copolymers of ethylene oxide and propylene oxide which contain the ethylene oxide and propylene oxide units in a statistically distributed manner.
- the oligomers of ethylene oxide or propylene oxide are also suitable for producing the crosslinkers, for example diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate and / or tetraethylene glycol dimethacrylate.
- crosslinking agents are vinyl esters of ethylenically unsaturated C 3 -C 6 -carboxylic acids, for example vinyl acrylate, vinyl methacrylate or vinyl itaconate.
- crosslinking agents are vinyl esters of saturated carboxylic acids containing at least 2 carboxyl groups and Di- and polyvinyl ethers of at least dihydric alcohols, eg divinyl adipate, butanediol divinyl ether and trimethylol propane trivinyl ether.
- Other crosslinkers are allyl esters of ethylenically unsaturated carboxylic acids, for example allyl acrylate and allyl methacrylate, allyl ethers of polyhydric alcohols, for example pentaerythritol triallyl ether, triallyl sucrose and pentallyl sucrose.
- crosslinking agents are methylene bis methacrylamide, divinyl ethylene urea, divinyl propylene urea, di vinyl benzene, divinyl glycol, tetraallylsilane and tetravinyl silane.
- the monomers of group (d) can optionally be present in the monomer mixtures in amounts of up to 10 mol% during the copolymerization. If the monomers of group (d) are copolymerized with the monomers of groups (a) and optionally (c), the amounts preferably used are 0.05 to 5 mol%, based on the monomer mixtures.
- Terpolymers prepared in a preferred manner are obtained by polymerizing monomer mixtures
- the copolymerization takes place in aqueous media, preferably in a purely aqueous solution.
- the copolymerization can optionally also be carried out in mixtures of water and bis
- C 4 alcohols such as methanol, ethanol, isopropanol and butanols are carried out, the proportion of alcohols in the mixture being at most 70% by weight.
- concentration of the polymers formed in the polymerization in the reaction mixture is usually 10 to 70, preferably 15 to
- Suitable initiators for the radical polymerization are particular ⁇ DERS suitable water-soluble azo compounds such as 2,2'-azobis [2 - (2 -imidazoline-2 -yDpropan], 2,2'-azobis [2-amidino- propane) and their acid addition salts , in particular their hydrochlorides, acetates or (hydrogen) sulfates, 4, 4 '-azobis / 4-cyano-valeric acid) and their alkali metal or ammonium salts or 2 - (carbamoylazo) isobutyronitrile.
- 2,2'-azobis [2 - (2 -imidazoline-2 -yDpropan] 2,2'-azobis [2-amidino- propane)
- their acid addition salts in particular their hydrochlorides, acetates or (hydrogen) sulfates, 4, 4 '-azobis / 4-cyano-valeric acid) and their alkali metal or ammonium salts or 2 - (carb
- azo group-containing polymerization initiators such as, for example, 2,2'-azobis (isobutyronitrile), 2,2'-azobis (2-methylbutyronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile) and 1, 1 '-azobis (1-cyclohexane carbonitrile) and water-soluble peroxides and hydroperoxides, such as, for example, hydrogen peroxide and peroxodisulfuric acid and their alkali metal and ammonium salts.
- 2,2'-azobis isobutyronitrile
- 2,2'-azobis (2-methylbutyronitrile) 2,2'-azobis (2,4-dimethylvaleronitrile)
- 1, 1 '-azobis (1-cyclohexane carbonitrile 1, 1 '-azobis (1-cyclohexane carbonitrile
- water-soluble peroxides and hydroperoxides such as, for example, hydrogen peroxide and peroxodisul
- Suitable hydroperoxides are, for example, t-butyl hydroperoxide, t-amyl hydroperoxide, cumene hydroperoxide and pinane hydroperoxide, each in combination with, for example, a salt of hydroxymethanesulfinic acid, an iron endl) salt or ascorbic acid.
- Suitable persalts are, in particular, alkali metal peroxydisulfates.
- too Perester such as tert. Butyl perpivalate or tert. -Butyl-per-2 - ethylhexanoate can be used as an initiator.
- the amount of initiator used for the polymerization is preferably in the range from 0.02 to 15% by weight, in particular 0.05 to 10% by weight and very particularly preferably 0.1 to 3% by weight, based on the total amount of monomer.
- the initiator is preferably supplied in dissolved, diluted or emulsified form.
- solvent optionally in the presence of suitable emulsifiers for the initiators may include water and / or organic solvents such as C T.
- - 2-alcohols are used to C-alcohols, alkylene, oligo- and polyalkylene glycols, and alkoxylation products of Ci to C .
- the initiators can also be used in the presence of emulsifiers in the solvents mentioned.
- the initiators can be metered in together with the monomers in the feed process (in this case the metering time of the initiator can exceed the metering time of the monomers).
- the initiator can also be presented in whole or in part.
- the monomers are polymerized in aqueous solution with the exclusion of polymerization regulators.
- polymerization regulators are understood to mean those substances which, during the polymerization, drastically reduce the degree of polymerization even in low concentrations (e.g. below 10% by weight, based on the monomers).
- the most effective polymerization regulators contain sulfur in bound form, e.g. Mercaptocarboxylic acids or thio alcohols.
- the pH values of the aqueous solutions are, for example, 2 or above, preferably pH values> 5. Polymerization is particularly preferably carried out at pH values> 6.
- Known buffers can optionally be used to keep a certain pH value constant .
- the pH can also be adjusted and / or maintained by adding acids such as hydrochloric acid or sulfuric acid or bases such as ammonia or sodium hydroxide during the polymerization.
- the polymerization can be carried out under normal pressure, under reduced pressure and at elevated pressures.
- the temperatures are, for example, 50 to 150, preferably 60 to 140 ° C. At temperatures above the boiling point of water, it is of course necessary to carry out the polymerization in a closed apparatus under pressure.
- the monomers to be polymerized can be introduced, for example, in a batch process. However, a procedure is particularly preferred in which one starts after the polymerization has started the monomers are introduced continuously or batchwise into the polymerization apparatus or the polymerization is carried out continuously in a stirred tank cascade or in a tube or else in combinations of a stirred tank and tube.
- the monomers can be metered into the polymerization zone either as a mixture in a single feed or else separately from one another in at least 2 feeds.
- for example 5 to 95% by weight of the monomers can be initially taken and the remaining monomers can be fed in as the polymerization progresses.
- post-polymerization can be carried out after the actual polymerization.
- the post-polymerization can be carried out at the temperature at which the main polymerization also took place or the reaction mixture is heated to a temperature which is, for example, 5 to 30 ° C. above the temperature in the main polymerization.
- the same initiator as for the main polymerization can be used for the post-polymerization, or an initiator mixture can also be used.
- Residual monomers can also be removed, for example, with the aid of a physical aftertreatment of the aqueous polymer solution.
- a suitable method of this kind is e.g.
- the polymers are preferably used in the form of the aqueous solutions, but can also be isolated from the aqueous solutions, for example by precipitation or by removing the water.
- the process according to the invention gives copolymers with molar masses above 60,000, preferably above 70,000 to, for example, up to 1,000,000 (determined by gel permeation chromatography).
- the molar masses of the copolymers are preferably in the range from 70,000 to 700,000.
- the copolymers are used, for example, as an additive to detergents to inhibit dye transfer during the washing process.
- they are contained in the detergent formulations, for example in amounts of 0.2 to 10, preferably 0.5 to 5% by weight. example 1
- the K value of the copolymer was 54.8 (determined in 5% by weight aqueous NaCl solution at 25 ° C. and a polymer concentration of 1% by weight). The K values were determined in 5% by H. Fikentscher, Cellulose-Chemie, Vol. 13, 58-64 and 71-76 (1983). - Aqueous NaCl solution at 25 ° C. As a gas chromatographic analysis showed, the copolymer contained 120 ppm 1-vinyl -2-methylimidazole, ⁇ 50 ppm N-vinyl pyrrolidone and 200 ppm acrylic acid as a residual monomer.
- copolymers described in the following table were prepared in accordance with the instructions given in the example.
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Abstract
Description
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Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98952596A EP1023341A1 (de) | 1997-10-01 | 1998-09-18 | Verfahren zur herstellung von anionisch modifizierten polymerisaten von alkyl-1-vinylimidazolen |
JP2000513880A JP2001518534A (ja) | 1997-10-01 | 1998-09-18 | アルキル−1−ビニルイミダゾールのアニオン変性ポリマーの製造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19743432.0 | 1997-10-01 | ||
DE1997143432 DE19743432A1 (de) | 1997-10-01 | 1997-10-01 | Verfahren zur Herstellung von anionisch modifizierten Polymerisaten von Alkyl-1-vinylimidazolen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999016798A1 true WO1999016798A1 (de) | 1999-04-08 |
Family
ID=7844310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/005944 WO1999016798A1 (de) | 1997-10-01 | 1998-09-18 | Verfahren zur herstellung von anionisch modifizierten polymerisaten von alkyl-1-vinylimidazolen |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1023341A1 (de) |
JP (1) | JP2001518534A (de) |
DE (1) | DE19743432A1 (de) |
WO (1) | WO1999016798A1 (de) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0438713A2 (de) * | 1990-01-16 | 1991-07-31 | BASF Aktiengesellschaft | Verfahren zur Entfernung von Schwermetallionen aus Wein und weinähnlichen Getränken |
DE4316023A1 (de) * | 1993-05-13 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von niedrigmolekularen Polymerisaten des 1-Vinylimidazols |
WO1995015345A1 (de) * | 1993-12-02 | 1995-06-08 | Basf Aktiengesellschaft | Polymerisate von alkyl-1-vinylimidazolen |
-
1997
- 1997-10-01 DE DE1997143432 patent/DE19743432A1/de not_active Withdrawn
-
1998
- 1998-09-18 WO PCT/EP1998/005944 patent/WO1999016798A1/de not_active Application Discontinuation
- 1998-09-18 JP JP2000513880A patent/JP2001518534A/ja not_active Withdrawn
- 1998-09-18 EP EP98952596A patent/EP1023341A1/de not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0438713A2 (de) * | 1990-01-16 | 1991-07-31 | BASF Aktiengesellschaft | Verfahren zur Entfernung von Schwermetallionen aus Wein und weinähnlichen Getränken |
DE4316023A1 (de) * | 1993-05-13 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von niedrigmolekularen Polymerisaten des 1-Vinylimidazols |
WO1995015345A1 (de) * | 1993-12-02 | 1995-06-08 | Basf Aktiengesellschaft | Polymerisate von alkyl-1-vinylimidazolen |
Also Published As
Publication number | Publication date |
---|---|
JP2001518534A (ja) | 2001-10-16 |
EP1023341A1 (de) | 2000-08-02 |
DE19743432A1 (de) | 1999-04-08 |
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