WO2002090406A1 - Esters partiels d'ethers d'allylpolyalkylenglycoliques, leur utilisation comme emulsifiants et monomeres hydrophiles dans la polymerisation d'emulsion - Google Patents

Esters partiels d'ethers d'allylpolyalkylenglycoliques, leur utilisation comme emulsifiants et monomeres hydrophiles dans la polymerisation d'emulsion Download PDF

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Publication number
WO2002090406A1
WO2002090406A1 PCT/EP2002/004439 EP0204439W WO02090406A1 WO 2002090406 A1 WO2002090406 A1 WO 2002090406A1 EP 0204439 W EP0204439 W EP 0204439W WO 02090406 A1 WO02090406 A1 WO 02090406A1
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WO
WIPO (PCT)
Prior art keywords
sodium
acid
polyethylene glycol
potassium
glycol ether
Prior art date
Application number
PCT/EP2002/004439
Other languages
German (de)
English (en)
Inventor
Hendrik Ahrens
Uwe Falk
Martin Glos
Original Assignee
Clariant Gmbh
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 Clariant Gmbh filed Critical Clariant Gmbh
Publication of WO2002090406A1 publication Critical patent/WO2002090406A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
    • 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
    • C08F216/00—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—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 an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1416—Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/327—Polymers modified by chemical after-treatment with inorganic compounds containing phosphorus
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
    • C08G65/3353—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus

Definitions

  • the present invention relates to partial esters of allyl polyalkylene glycol ether with polyvalent acids, and their use as emulsifiers and hydrophilic monomers in emulsion polymerizations.
  • the emulsifiers used for the emulsion polymerization according to the prior art are mostly anionic and nonionic emulsifiers.
  • Common anionic emulsifiers are sodium, potassium and ammonium salts of fatty acids, sodium alkylbenzenesulfonates, sodium alkylsulfonates, sodium olefin sulfonates, sodium polynaphthalene sulfonates, sodium dialkyldiphenylether disulfonates, sodium, potassium and ammonium alkyl sulfates, sodium, potassium and ammonium alkyl sulfates, glycol ether sulfates, sodium, potassium and ammonium mono- and dialkyl sulfosuccinates and monoalkylpolyoxethyl sulfosuccinates, as well as alkyl polyethylene glycol ether phosphoric acid mono-, di- and triesters and their mixtures and alkylphenol polyethylene glycol ether phosphoric acid mono-, di- and triester and their mixtures, as well as their sodium, potassium and ammonium salts.
  • Alkylphenol polyethylene glycol ether, alkyl polyethylene glycol ether, fatty acid polyethylene glycol ether, ethylene / propylene glycol block polymers and sorbitan ester polyethylene glycol ether are usually used as nonionic emulsifiers.
  • Emulsion polymerizations are made using anionic and Nonionic emulsifiers are generally carried out using the total batch or in the feed process, in which only a small part of the monomers to be polymerized is placed in the polymerization vessel and the larger part (50 to 100% by weight) is added as the polymerization progresses.
  • the anionic or nonionic emulsifiers are optionally used in the feed or in the reactor receiver during the emulsion polymerization, or are added subsequently to the polymer dispersion prepared for stabilization.
  • the emulsifiers used according to the prior art are bound to the surface of the polymer particles via physical forces.
  • the object of the present invention was therefore to find new emulsifiers for emulsion polymerization. These emulsifiers are said to copolymerize with the monomers used and thus to be chemically bound in the polymer particles.
  • the invention therefore relates to partial esters of alcohols of the formula (1)
  • Oxygen atoms still have at least one phosphorus or sulfur atom, wherein
  • R is a methyl or ethyl radical
  • n is a number from 1 to 100
  • m is a number from 0 to 500.
  • the alcohols of the formula 1 are those alkoxylates whose alkoxy groups are arranged in blocks.
  • n is a number from 2 to 50, in particular 3 to 30.
  • m denotes a number from 2 to 100, in particular 3 to 50.
  • R represents a methyl group
  • inorganic acids which are suitable for forming the partial esters according to the invention are sulfuric acid and phosphoric acid. If phosphoric acid is used, the partial esters according to the invention can be either monoesters or diesters of phosphoric acid.
  • the organic or inorganic acids used to esterify the alcohols according to formula 1 are divalent or trivalent.
  • the organic acids are di-, tri- or polyvalent carboxylic acids, i.e. Compounds which contain 2, 3 or more carboxyl groups and which additionally have at least one functional group containing sulfur or phosphorus. Sulfur-containing functional groups, especially sulfonate groups, are particularly preferred.
  • the particularly preferred sulfonic acids / sulfonates can be aliphatic or aromatic compounds.
  • Preferred sulfonic acids / sulfonates contain 2 or 3 carboxyl groups and, including the carboxyl groups, 3 to 6 carbon atoms.
  • a particularly preferred sulfonic acid is sulfosuccinic acid.
  • Particularly preferred partial esters thus correspond to formulas (2) to (5)
  • R, m and n have the meaning given above, and M stands for an alkali metal ion, an ammonium ion or for H + .
  • the partial esters according to the invention can be prepared by reacting the alcohols of the formula 1 with suitable acids. However, care must be taken to ensure that the acids do not have an oxidizing effect, since otherwise the allylic double bond can be oxidized. For this reason, the preparation of partial sulfate esters is preferably carried out with amidosulfonic acid instead of with sulfuric acid. Phosphoric acid can be used for the preparation of partial phosphoric acid esters. Organic acids are preferably reacted in the form of their anhydrides with the alcohols of the formula 1. Functional groups are preferably inserted after the partial transfer has been produced non-functionalized acid. For example, the sulfosuccinic acid esters of formula 5 can be prepared by preparing the corresponding maleic acid esters and the subsequent sulfonation, for example using pyrosulfites.
  • Another object of the invention is the use of the partial esters according to the invention as polymerizable emulsifiers in emulsion polymerization.
  • the partial esters according to the invention are polymerized with further monomers from which a polymer dispersion is to be prepared.
  • Unsaturated monomers are suitable for the production of polymer dispersions.
  • Preferred olefinically unsaturated monomers are, for example
  • Aryl-substituted olefins such as styrene and stilbene, olefinically unsaturated carboxylic acid esters, such as methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, i-butyl acrylate, pentyl acrylate, hexyl acrylate,
  • the above-mentioned monomers are mixed with further comonomers, preferably olefins or halogenated olefins having 2 to 8 carbon atoms, e.g. Polymerized ethylene, propene, butenes, pentenes, 1, 3-butadiene, chloroprene, vinyl chloride, vinylidene chloride, vinylidene fluoride and tetrafluoroethylene.
  • further comonomers preferably olefins or halogenated olefins having 2 to 8 carbon atoms, e.g. Polymerized ethylene, propene, butenes, pentenes, 1, 3-butadiene, chloroprene, vinyl chloride, vinylidene chloride, vinylidene fluoride and tetrafluoroethylene.
  • the invention therefore furthermore relates to a process for the preparation of polymer dispersions by polymerizing the partial esters according to the invention with olefinically unsaturated monomers in the aqueous phase, and to the aqueous polymer dispersion which can be prepared in this way.
  • the water-immiscible monomers are generally finely divided in the aqueous phase in the form of micelles with the aid of the partial esters according to the invention and the radical polymerization reaction is initiated by initiators such as ammonium, sodium and potassium peroxodisulfate.
  • auxiliaries and additives for use with the partial esters according to the invention can be protective colloids such as carboxymethyl cellulose, hydroxyethyl cellulose, methyl hydroxypropyl cellulose, and partially and fully hydrolyzed polyvinyl alcohol.
  • the partial esters according to the invention are placed in the reaction vessel before the start of the polymerization reaction or added to the reaction vessel during the polymerization reaction.
  • the partial esters according to the invention are used in amounts of 0.1 to 50, preferably 0.2 to 10, in particular 0.4 to 4% by weight, based on the weight of the non-water-soluble or slightly water-soluble olefinically unsaturated used for the preparation of the polymer dispersion Monomers used as emulsifiers.
  • the partial esters according to the invention can be used both alone and in combination with other already known anionic and nonionic emulsifiers of the prior art, as described at the beginning.
  • the amount of the anionic and nonionic emulsifiers of the prior art is then preferably 0.001 to 5, in particular 0.01 to 1% and particularly preferably 0.02 to 0.4% by weight, based on the weight of the insoluble or slightly water-soluble olefinically unsaturated Monomers.
  • the polymer dispersions produced with the partial esters according to the invention show low coagulum formation during and after the polymerization and an improvement in the shear, temperature and storage stability, the freeze / thaw stability and the electrolyte stability compared to divalent and trivalent cations such as calcium, barium and aluminum. An improvement in the film properties of the polymer films produced from the polymer dispersions can also be observed.
  • Polymer dispersions form films with low water absorption, a low whitening on contact with water, a small contact wrap against water and good wet and dry rub fastness.
  • Example 4 500 g of an allyl polyoxyalkylene glycol were added under nitrogen with 97 g
  • Example 7 475 g of an allyl polyoxyalkylene glycol became 61 g under nitrogen
  • 210 g of an allyl polyoxyalkylene glycol were mixed at 70 ° C with 85 g of polyphosphoric acid and stirred at 70 ° C for 3 h. After a further 4 hours at 100 ° C., 20 g of water were added at 90 ° C. and the mixture was stirred for a further 2 hours. 310 g of product were obtained, which was a mixture of 79% by weight of phosphoric acid monoester and 4% by weight of phosphoric acid diester, the rest being water. The product did not contain a phosphoric triester.
  • the resulting polymer dispersion has a solids content of 52% and a coagulate of ⁇ 0.010% over a 100 ⁇ m sieve and ⁇ 0.015% over a 40 ⁇ m sieve.
  • a monomer emulsion consisting of 554 g of fully demineralized water, 33 g of the allyl polyalkylene glycol ether sulfate according to the invention, 6 g of sodium hydrogen carbonate, 360 g of styrene, 500 g of n-butyl acrylate, 240 g of methyl acrylate and 11 g of methacrylic acid and an initiator solution consisting of 5.55 g of ammonium peroxodisulfate and 142.5 ml of completely deionized water.
  • the resulting polymer dispersion had a solids content of 52% and a coagulum of ⁇ 0.030% over a 100 ⁇ m sieve and of ⁇ 0.030% over a 40 ⁇ m sieve.
  • Initiator solution started. Both components were metered in with constant stirring using an anchor stirrer and under a nitrogen atmosphere within a period of
  • the resulting polymer dispersion had a solids content of 65% and a coagulate of ⁇ 0.004% over a 100 ⁇ m sieve and of ⁇ 0.006% over a 40 ⁇ m sieve.
  • the resulting polymer dispersion had a solids content of 51% and a coagulate of ⁇ 0.20% over a 100 ⁇ m sieve and of ⁇ 0.30% over a 40 ⁇ m sieve.
  • the resulting polymer dispersion had a solids content of 65% and a coagulum of ⁇ 0.10% over a 100 ⁇ m sieve and of ⁇ 0.15% over a 40 ⁇ m sieve.

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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)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polyethers (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention concerne des esters partiels d'alcools de la formule (1) contenant deux acides anorganiques ou organiques bivalents ou polyvalents qui non seulement ont des atomes d'oxygène mais aussi au moins un atome de phosphore ou de soufre, sachant que R représente un reste méthyle ou éthyle, n vaut un nombre de 1 à 100 et m vaut un nombre de 0 à 500.
PCT/EP2002/004439 2001-05-04 2002-04-23 Esters partiels d'ethers d'allylpolyalkylenglycoliques, leur utilisation comme emulsifiants et monomeres hydrophiles dans la polymerisation d'emulsion WO2002090406A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10121707A DE10121707A1 (de) 2001-05-04 2001-05-04 Teilester von Allylpolyalkylenglycolethern und deren Verwendung als Emulgatoren und hydrophile Monomere in der Emulsionspolymerisation
DE10121707.2 2001-05-04

Publications (1)

Publication Number Publication Date
WO2002090406A1 true WO2002090406A1 (fr) 2002-11-14

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WO (1) WO2002090406A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1717259A1 (fr) * 2005-04-30 2006-11-02 Clariant Produkte (Deutschland) GmbH Macromonomères copolymérisables à base de polyalkylène glycol, leur préparation et leur utilisation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3735049A1 (de) * 1986-10-27 1988-07-28 Sandoz Ag Tenside
US4830764A (en) * 1986-10-27 1989-05-16 Sandoz Ltd. Polyoxyalkylene-containing phosphoric acid esters
US4931218A (en) * 1987-07-15 1990-06-05 Henkel Kommanditgesellschaft Auf Aktien Sulfated hydroxy mixed ethers, a process for their production, and their use
US4986851A (en) * 1986-08-09 1991-01-22 Hoechst Aktiengesellschaft Pigment dispersions, processes for their preparation and their use
WO2001096007A1 (fr) * 2000-06-15 2001-12-20 Coatex S.A. Utilisation de copolymeres faiblement anioniques comme agent dispersant et/ou d'aide au broyage de suspension aqueuse de matieres minerales

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4986851A (en) * 1986-08-09 1991-01-22 Hoechst Aktiengesellschaft Pigment dispersions, processes for their preparation and their use
DE3735049A1 (de) * 1986-10-27 1988-07-28 Sandoz Ag Tenside
US4830764A (en) * 1986-10-27 1989-05-16 Sandoz Ltd. Polyoxyalkylene-containing phosphoric acid esters
US4931218A (en) * 1987-07-15 1990-06-05 Henkel Kommanditgesellschaft Auf Aktien Sulfated hydroxy mixed ethers, a process for their production, and their use
WO2001096007A1 (fr) * 2000-06-15 2001-12-20 Coatex S.A. Utilisation de copolymeres faiblement anioniques comme agent dispersant et/ou d'aide au broyage de suspension aqueuse de matieres minerales

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DE10121707A1 (de) 2002-12-12

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