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WO1996004332A1 - Procede de fabrication de polymeres renfermant, en chaine laterale, des groupes acide hydroxamique, ether d'acide hydroxamique et/ou hydrazide, et leur utilisation - Google Patents

Procede de fabrication de polymeres renfermant, en chaine laterale, des groupes acide hydroxamique, ether d'acide hydroxamique et/ou hydrazide, et leur utilisation Download PDF

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Publication number
WO1996004332A1
WO1996004332A1 PCT/EP1995/002891 EP9502891W WO9604332A1 WO 1996004332 A1 WO1996004332 A1 WO 1996004332A1 EP 9502891 W EP9502891 W EP 9502891W WO 9604332 A1 WO9604332 A1 WO 9604332A1
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WO
WIPO (PCT)
Prior art keywords
polymers
hydroxamic acid
groups
side chain
acid
Prior art date
Application number
PCT/EP1995/002891
Other languages
German (de)
English (en)
Inventor
Thomas Greindl
Elisabeth Kappes
Alfred Oftring
Alexander Kud
Richard Baur
Matthias Kroner
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO1996004332A1 publication Critical patent/WO1996004332A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/48—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1092—Polysuccinimides
    • 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
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3719—Polyamides or polyimides
    • 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

Definitions

  • the invention relates to a process for the preparation of polymers which contain hydroxamic acid, hydroxamic acid ether and / or hydrazide groups in the side chain, by polymer-analogous reaction with hydroxylamine, hydroxylamine-O-alkyl ethers and / or hydrazine and the use of the polymers as Additive to detergents and cleaning agents, as a complexing agent, dispersant and as a scale inhibitor.
  • modified polyaspartic acids which can be obtained by polycondensation of aspartic acid with fatty acids, polybasic carboxylic acids, alcohols, amines or, for example, with hydroxylamine or with hydrazine.
  • the modified polyaspartic acids are used as additives to low-phosphate and phosphate-free detergents and cleaning agents, as water treatment agents and as deposit inhibitors in the evaporation of sugar juice.
  • hydroxylamine and hydrazine have a chain-terminating effect, so that the degrees of polycondensation of the modified polyaspartic acids obtainable in this way are limited.
  • the object of the present invention is to provide a process for the preparation of polymers which contain hydroxamic acids in the side chain and which are biodegradable if possible.
  • the object is achieved according to the invention with a process for the preparation of polymers which contain hydroxamic acid, hydroxamic acid ether and / or hydrazide groups in the side chain, if one
  • the polymers containing hydroxamic acid, hydroxamic acid ether and / or hydrazide groups obtainable in this way are used as additives for detergents and cleaning agents, as complexing agents for alkaline earth and heavy metal ions, as dispersants for pigments and as scale inhibitors.
  • the polymers that are suitable as component (a) should preferably be biodegradable.
  • Such polymers are, for example, polyester carboxylates, they contain repeating ester groups in the main polymer chain and carboxyl or carboxylate groups in the side chain.
  • Such polyester carboxylates are produced, for example, by polycondensing dihydric or polyhydric alcohols with a carboxylic acid having at least three carboxyl groups or an ester of such a carboxylic acid.
  • polyester carboxylates are poly (malic acid), poly (malic acid) methyl ester, poly (malic acid) ethyl ester, poly tartaric acid dimethyl ester, polycitric acid and polyester, which according to the teaching of EP-A-0 484 606 by condensation of tartaric acid, tartaric anhydride alone or by condensation and mixtures of tartaric anhydride or tartaric acid anhydride or are available in a molar ratio of 1: 0.1 to 1: 4. In the production of these polyesters, the condensation can optionally be carried out additionally in the presence of up to 60 mol% of malic acid. Also suitable as polymers (a) are the polyester carboxylates known from WO-A-93/13192, which by condensation of
  • Butane-l, 2,3,4-tetracarboxylic acid which can be replaced by up to 70 mol% with mono- or dibasic hydroxycarboxylic acids or up to 49 mol% with other two- to four-basic aliphatic carboxylic acids (2 ) polyhydroxy compounds from the group of the mono-, oligo- and polysaccharides of the reduced mono- or oligosaccharides and their amino derivatives, the oxidized mono-, oligo- or polysaccharides, alkyl polyglycosides, polyvinyl alcohols, oligoglycerols with more than two glycerol units or their mixtures and optionally
  • polystyrene resin Another suitable group of polymers (a) are polyacetal carboxylates. Such compounds are known for example from EP-B-0 001 004. They are made by polymerizing
  • Glyoxylic acid esters prepared in the presence of initiators. They contain repeating acetal groups in the main chain and ester groups of C 4 -C 4 -alcohols, alkanolamine groups, free carboxyl groups or carboxylate groups which can be obtained by neutralization with alkali metal bases or ammonium bases. These polyacetal carboxylates are biodegradable. Further suitable polyacetals are known, for example, from WO-A-92/15629. They are prepared, for example, by polymerizing methyl ⁇ -formylpropionate and, if appropriate, hydrolysing the ester groups of the polyacetal carboxylates. Of the polyester carboxylates, polyglyoxylic acid or methyl polyglyoxylate is preferably used as polymer (a).
  • polymers (a) are polyamide carboxylates. These polymers contain repeating carbonamide groups in the main chain and free carboxyl groups in the side chain, carboxyl groups neutralized with alkali metal bases or ammonium bases or they are esterified with C 1 -C 4 -alcohols.
  • polyamide carboxylates are polyglutonic acid, polyglutamic acid benzyl ester, polyglutamic acid methyl ester, polyglutamic acid ethyl ester, polyaspartic acid, polyaspartic acid methyl ester and polyaspartic acid ethyl ester.
  • the pendant carboxyl groups can also be in the form of the amides, imides, nitriles or as anhydride groups or can be replaced by halogen.
  • Polysuccinimide is also suitable as polymer (a). It can be prepared, for example, by solid-phase polycondensation of powdered aspartic acid at 200 to 250 ° C or by polymerizing aspartic acid in the presence of phosphoric acid or phosphorous acid at 140 to 250 ° C. Poly succinimide is also formed by polycondensation of adducts from maleic acid, maleic anhydride, fumaric acid or malic acid with ammonia or ammonium salts at 120 to 300 ° C.
  • the molecular weight of the polymers mentioned under (a) (weight average) is, for example, 500 to 200,000, preferably 500 to 20,000.
  • the compound of component (b) is hydroxylamine or the above-mentioned hydroxyl derivative. Because of the ease of handling, hydroxylamine is preferably used in the form of the salts, for example as hydrochloride or as hydroxylammonium sulfate or as a solution in an organic solvent such as methanol or ethanol. Also suitable as compounds of component (b) are hydroxylamine O-alkyl ethers having 1 to 18 carbon atoms in the alkyl group. From this group of compounds, the hydroxylamine methyl ether and hydroxylaminethyl ether are preferably used. Also suitable as compounds of group (b) are N-monoalkylhydroxylamines having 1 to 18 carbon atoms in the alkyl group. The hydroxylamine alkyl ethers and the N-monoalkyl-substituted hydroxylamines can also be used in the form of the salts, for example as chloride, phosphate or sulfate.
  • the group (c) compound which can be used is hydrazine which, like the compounds of group (b) - can be used in the form of the salts, e.g. Hydrazine sulfate or hydrine hydrochloride.
  • the reaction of the polymers (a) with the compounds (b) and / or (c) takes place, for example, in an aqueous medium or in alcohols at pH values of at least 7.
  • Suitable alcohols are soluble in water, such as methanol, ethanol, isopropanol, n- Butanol, ethylene glycol, propylene glycol and glycerin.
  • Suitable solvents are also polyalkylene glycols such as polyethylene glycol, polypropylene glycol, polytetrahydrofuran and alkoxylated Ci to Ci ⁇ alcohols, which can contain, for example, 1 to 100 ethylene oxide units per mole of alcohol.
  • the lying connection be understood as water as the sole solvent as well as in a mixture with a water-soluble alcohol, polyalkylene glycol and / or an alkoxylated alcohol.
  • 0.001 to 1, preferably 0.1 to 1.0 mol of the compounds (b) and / or (c) are used per mole of the functional groups in the side chain of the polymers (a).
  • the reaction of the polymers (a) with the compounds (b) and / or (c) is preferably carried out at pH values from 7.5 to 12 and mostly in the pH range from 8.0 to 11.0.
  • the pH of the reaction mixture is adjusted by adding bases to the reaction mixture and is advantageously checked during the reaction period. All alkali metal bases can be used as bases for adjusting the pH, preferably sodium hydroxide solution and potassium hydroxide solution, alkaline earth metal bases such as calcium hydroxide or barium hydroxide, and ammonia and amines. Sodium hydroxide solution or potassium hydroxide solution is preferably used as the base.
  • the reaction times depend on the pH of the reaction medium and the temperature.
  • the temperatures at which the reaction is carried out are usually 0 to 100 ° C, but can also be outside this range.
  • the reaction is preferably carried out at temperatures of 20 to 90 ° C.
  • the response times are e.g. between one minute and 60 hours, usually 30 minutes to 50 hours.
  • components (b) and / or (c) can, for example, be introduced in an aqueous medium or in an alcohol and the polymers (a) added in portions, continuously or all at once.
  • the procedure can also be such that the polymers (a) are initially introduced into a solution, the solids content of these solutions being, for example, 5 to 80% by weight, and for this the components (b) and / or (c) depending on Reactivity added in portions, continuously or all at once and allowed to react.
  • the method can be carried out continuously or batchwise.
  • the polymers (a) used are preferably polyester carboxylates, polyglyoxylic esters, polyglyoxylic acid, alkali or ammonium salts of polyglyoxylic acid, polysuccinimides, polyaspartic acid and the sodium or ammonium salts of polyaspartic acid and / or polyamide carboxylates.
  • polyaspartic acids containing hydroxamic acid groups are prepared by: (a) polysuccinimide, polyaspartic acid and / or water-soluble alkali metal, ammonium or alkaline earth metal salts of polyaspartic acid with
  • the aspartic acid in the polysuccinimides can be linked in an ⁇ - or ⁇ -like manner.
  • the proportions of both forms can be different.
  • the proportion of both forms in the polysuccinimide can be, for example, 10 to 90 mol%.
  • Polyaspartic acid, polyglutamic acid, polyglyoxylic acid, poly malic acid, poly tartaric acid or polycitric acid containing hydroxamic acid groups are biodegradable.
  • the polymers containing hydroxamic acid, hydroxamic acid ether and / or hydrazide groups obtainable by the process according to the invention are used, for example, as an additive to phosphate-reduced or phosphate-free washing and cleaning agents.
  • Phosphate-reduced detergents and cleaning agents are to be understood as meaning those formulations which contain less than 25% by weight of phosphate, calculated as trisodium polyphosphate.
  • the compounds to be used according to the invention are used in amounts of 0.1 to 30, preferably 1.0 to 10% by weight in detergents and cleaning agents. They act as a bleach activator if the detergents and cleaning agents contain a perborate, for example.
  • the high incrustation-inhibiting effect of polyaspartic acids containing hydroxamic acid groups is particularly remarkable.
  • the polymers obtainable by the process according to the invention which contain hydroxamic acid, hydroxamic acid ether and / or hydrazide groups in the side chain have, for example, molecular weights from 150 to 200,000, preferably from 300 to 50,000 (weight average).
  • the products produced according to the invention are also suitable as complexing agents for alkaline earth and heavy metal ions and as dispersants for pigments. Dispersants are used, for example, in amounts of 0.01 to 2% by weight, based on the pigments. Another area of application of the polymers prepared according to the invention is as a scale inhibitor.
  • Scaleinhihibtoren are usually used in amounts of 1 to 100 ppm, based on the aqueous system.
  • the polymers described are of particular importance for seawater desalination in the latter application. They can also be used as deposit inhibitors for the evaporation of sugar juices.
  • the K values of the polymers were determined according to H. Fikentscher, Cellulose-Chemie, Vol. 13, 58 to 64 and 71 to 74 (1932) in one percent solution in dimethylformamide (unless another solvent is specified) at a temperature of 25 ° C. certainly.
  • the molecular weight Mw was determined on the sodium form of the polymers with the aid of gel permeation chromatography, polyacrylic acids calibrated using the light scattering method being used as calibration substances. The percentages in the examples mean percent by weight.
  • the molecular weight of the polymer in the salt form is 1,600.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Detergent Compositions (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Procédé de fabrication de polymères renfermant, en chaîne latérale, des groupes acide hydroxamique, éther d'acide hydroxamique et/ou hydrazide, caractérisé en ce qu'on fait réagir, en milieu aqueux ou dans des alcools, à pH au moins égal à 7, (a) des polymères renfermant, dans la chaîne principale polymère, des groupes ester, amide, imide et/ou acétal et, comme chaîne latérale, des groupes carboxyle, ester, imide et/ou anhydride, et/ou un halogène, ou un polysuccinimide, avec (b) de l'hydroxylamine, des alkyléthers d'hydroxylamine de 1 à 18 atomes de carbone dans le groupe alkyle, des N-monoalkylhydroxylamines de 1 à 18 atomes de carbone dans le groupe alkyle et/ou dans des sels des composés précités et/ou (c) de l'hydrazine et/ou des sels de l'hydrazine, et utilisation des polymères modifiés ainsi obtenus, comme adjuvants d'agents de lavage et de détergents, comme complexants pour des ions de métaux alcalino-terreux et de métaux lourds, comme agents dispersants pour des pigments et comme agents d'anti-incrustation.
PCT/EP1995/002891 1994-08-04 1995-07-21 Procede de fabrication de polymeres renfermant, en chaine laterale, des groupes acide hydroxamique, ether d'acide hydroxamique et/ou hydrazide, et leur utilisation WO1996004332A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4427630.3 1994-08-04
DE4427630A DE4427630A1 (de) 1994-08-04 1994-08-04 Verfahren zur Herstellung von Polymeren, die in der Seitenkette Hydroxamsäure-, Hydroxamsäureether- und/oder Hydrazidgruppen enthalten und ihre Verwendung

Publications (1)

Publication Number Publication Date
WO1996004332A1 true WO1996004332A1 (fr) 1996-02-15

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PCT/EP1995/002891 WO1996004332A1 (fr) 1994-08-04 1995-07-21 Procede de fabrication de polymeres renfermant, en chaine laterale, des groupes acide hydroxamique, ether d'acide hydroxamique et/ou hydrazide, et leur utilisation

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DE (1) DE4427630A1 (fr)
WO (1) WO1996004332A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8720694B2 (en) 2008-07-25 2014-05-13 Cytec Technology Corp. Flotation reagents and flotation processes utilizing same

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5929198A (en) * 1996-07-16 1999-07-27 Nalco Chemical Company Biodegradable poly (amino acid)s, derivatized amino acid polymers and methods for making same
US5750070A (en) * 1996-07-19 1998-05-12 Nalco Chemical Company Use of biodegradable polymers in preventing corrosion and scale build-up
DE69825563T2 (de) * 1997-12-18 2005-08-04 Nippon Shokubai Co. Ltd. Amidgruppe enthaltendes Polyacetal und sein Herstellungsverfahren und Verwendung
CA2592095C (fr) 2004-12-24 2013-07-30 Basf Aktiengesellschaft Surfactifs non ioniques pour extraction des metaux
DE102009019852A1 (de) * 2009-05-06 2010-11-11 Schebo Biotech Ag Polymere mit neuen Strukturelementen, Verfahren zu ihrer Herstellung und ihre Verwendung
KR101505334B1 (ko) 2010-08-03 2015-03-23 바스프 에스이 연마제용 캐리어 유체
DE102011082377A1 (de) * 2011-09-08 2013-03-14 Henkel Ag & Co. Kgaa Wasch- und Reinigungsmittel mit verbesserter Leistung
KR20140110107A (ko) 2012-02-01 2014-09-16 바스프 에스이 웨이퍼 제조를 위한 냉각 및/또는 윤활 유체

Citations (3)

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Publication number Priority date Publication date Assignee Title
US4874539A (en) * 1987-08-06 1989-10-17 American Cyanamid Company Carboxy hydroxamic acid polymers and their use as detergent additives
EP0384911A2 (fr) * 1989-02-21 1990-08-29 Monsanto Company Compositions stabilisées contenant des composés peroxygénés
EP0454126A1 (fr) * 1990-04-26 1991-10-30 Rohm And Haas Company Acides aminés polymères en tant qu'adjuvants pour formulations détergentes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4874539A (en) * 1987-08-06 1989-10-17 American Cyanamid Company Carboxy hydroxamic acid polymers and their use as detergent additives
EP0384911A2 (fr) * 1989-02-21 1990-08-29 Monsanto Company Compositions stabilisées contenant des composés peroxygénés
EP0454126A1 (fr) * 1990-04-26 1991-10-30 Rohm And Haas Company Acides aminés polymères en tant qu'adjuvants pour formulations détergentes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8720694B2 (en) 2008-07-25 2014-05-13 Cytec Technology Corp. Flotation reagents and flotation processes utilizing same
US10130956B2 (en) 2008-07-25 2018-11-20 Cytec Technology Corp. Flotation reagents and flotation processes utilizing same
US11007538B2 (en) 2008-07-25 2021-05-18 Cytec Technology Corp. Flotation reagents and flotation processes utilizing same

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