WO2003104299A1 - Verfahren zur herstellung von estern von polyalkoholen - Google Patents

Verfahren zur herstellung von estern von polyalkoholen Download PDF

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Publication number
WO2003104299A1
WO2003104299A1 PCT/EP2003/005940 EP0305940W WO03104299A1 WO 2003104299 A1 WO2003104299 A1 WO 2003104299A1 EP 0305940 W EP0305940 W EP 0305940W WO 03104299 A1 WO03104299 A1 WO 03104299A1
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Prior art keywords
acid
reaction mixture
polyalcohol
weight
independently
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PCT/EP2003/005940
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German (de)
English (en)
French (fr)
Inventor
Thomas Jaworek
Thomas Daniel
Lothar Wolf
Rainer Königer
Reinhold Schwalm
Gabriele Hartmann
Stefan Wickel
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BASF SE
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BASF SE
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Application filed by BASF SE filed Critical BASF SE
Priority to JP2004511365A priority Critical patent/JP2005533875A/ja
Priority to AU2003242636A priority patent/AU2003242636A1/en
Priority to BRPI0311500-3A priority patent/BR0311500B1/pt
Priority to US10/514,569 priority patent/US7250481B2/en
Priority to MXPA04012091A priority patent/MXPA04012091A/es
Priority to EP03757035A priority patent/EP1516010B1/de
Publication of WO2003104299A1 publication Critical patent/WO2003104299A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/60—Liquid-swellable gel-forming materials, e.g. super-absorbents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds

Definitions

  • a disadvantage of these compounds is that for the at least partial separation of starting materials and by-products - the crosslinkers used in the mentioned document have a content of acrylic acid of less than 0.1% by weight - complex cleaning operations are required.
  • a disadvantage of this process is that due to the low reaction temperature, the reaction times are up to 35 hours and the excess acid in the reaction mixture is removed by neutralization with subsequent phase separation.
  • the polyhydric alcohol A has at least two hydroxyl functions
  • Crosslinking in this document is understood as meaning, unless otherwise stated, radical crosslinking (gel crosslinking, internal crosslinking, cross-linking of linear or slightly crosslinked polymer). This crosslinking can take place via free-radical or cationic polymerization mechanisms or other, for example Michael addition, esterification or esterification mechanisms, preferably by free-radical polymerization.
  • Hydrogel-forming polymers which absorb aqueous liquids are preferably those having an absorption of distilled water of at least their own weight, preferably 10 times their own weight, and this absorption is preferably also achieved under a pressure of 0.7 psi.
  • the polyols can also carry additional functionalities such as ether functions (-0-), carboxyl functions (-C00H) or -CC 4 -alkyloxycarbonyl (ester groups), where -CC 4 -alkyl in this specification methyl, ethyl, iso-propyl , n-propyl, n-butyl, iso-butyl, sec-butyl or terfc-butyl.
  • R 1 , R 2 independently of one another are hydrogen, C 1 -C 10 -alkyl, preferably C 1 -C 4 -alkyl, C 1 -C 10 -hydroxyalkyl, preferably C 1 -C 4 -alkyl, carboxyl or C 1 -C 4 -alkyloxycarbonyl, preferably hydrogen, hydroxymethyl and C 1 -C 4 -alkyl and particularly preferably hydroxymethyl and C 1 -C 4 -alkyl.
  • sugar alcohols examples include sorbitol, mannitol, maltitol, isomalt, diglycerol, threitol, erythritol, adonite (ribitol), arabitol (lixit), xylitol and dulcitol (galactitol).
  • polyesterols are e.g. those into consideration, such as can be prepared by esterification of polycarboxylic acids, preferably dicarboxylic acids, with the abovementioned polyols.
  • Y is a straight-chain or branched, optionally substituted alkylene group having 2 to 20 carbon atoms or an optionally substituted cycloalkylene or arylene group having 6 to 12 carbon atoms or a single bond
  • the saponification i. the cleavage of the ester groups contained in the polyesterol, for example, at least 10% based on the ester groups in the starting compound, preferably at least 25%, more preferably at least 50%, very particularly preferably at least 75% and in particular at least 90% ,
  • reaction mixture is then acidified and esterified with the carboxylic acid B as described.
  • the underlying alcohol to be esterified has the formula Vlla,
  • R 8 , R 10 , x and y are as defined above.
  • the alkylene oxide chain may preferably be composed of ethylene oxide, propylene oxide and / or butylene oxide units. Such a chain may be composed of a species of an alkylene oxide or a mixture of alkylene oxides. When a mixture is used, the different alkylene oxide units may be random or block or blocks of individual species.
  • one radical R 10 per alkylene oxide unit is preferably hydrogen and the other is methyl or hydrogen, particularly preferably both radicals R 10 are hydrogen.
  • the preferred number of alkylene oxide units in each chain depends on the number of chains.
  • the esterifying agent is a straight-chain or branched ethylenically unsaturated carboxylic acid having 2 to 10 carbon atoms or its esters, preferably having 2 to 4 and more preferably having 2 to 3 carbon atoms ethylenically unsaturated carboxylic acid, most preferably acrylic acid, methacrylic acid or their esters, especially acrylic acid.
  • R 1 , R 2 have the meanings given above,
  • k, 1, m, q are each independently an integer from 1 to 10, preferably 1 to 5, particularly preferably 3 to
  • Equally preferred is one to 20 times, preferably one to ten times, more preferably two to ten times, very preferably two to five times, especially three to five times and especially three to four times alkoxylated, preferably ethoxylated, propoxylated or mixed-ethoxylated-propoxylated and particularly preferred ethoxylated glycerol (here exceptionally calculated in moles of alkoxy groups per mole of glycerol).
  • the indicated degrees of alkoxylation in each case relate to the average degree of alkoxylation.
  • the data for the number-average and weight-average molecular weight M n and M w relate here to gel permeation chromatographic measurements, polystyrene being used as standard and tetrahydrofuran as eluent. The method is described in the Analyst Taschenbuch Vol. 4, pages 433 to 442, Berlin 1984.
  • R 1, R 2, Y have the abovementioned meanings, k, 1, m, q, r, s independently of one another are each an integer from 1 to 30, preferably 1 to 20, particularly preferably 1 to 10 and in particular 1 to 5 and
  • hydroquinone monomethyl ether particularly preferred are hydroquinone monomethyl ether, hydroquinone, and alkylphenols, optionally in combination with Tripehnyl- phosphite and / or hypophosphorous acid.
  • Suitable circulation evaporators are known to the person skilled in the art and are described, for example, in R. Billet, Verdampfertechnik, HTB-Verlag, bibliographisches Institut Mannheim, 1965, 53.
  • Examples of circulation evaporators are shell-and-tube heat exchangers, plate heat exchangers, etc. Of course, several heat exchangers may be present in the circulation.
  • They are generally used in an amount of from 0.1 to 5% by weight, based on the esterification mixture, preferably from 0.5 to 5, more preferably from 1 to 4 and very particularly preferably from 2 to 4% by weight.
  • the amount of solvent used is 10 to 200% by weight, preferably 20 to 100% by weight, particularly preferably 30 to 100% by weight, based on the sum of polyhydric alcohol and carboxylic acid B.
  • the organic phase when used as reflux, can be used to control the temperature in the esterification.
  • the usable carboxylic acid B is not limited in its composition and in the case of crude (meth) acrylic acid, for example, the following components:
  • the pure (meth) acrylic acid used is generally stabilized with 100-300 ppm of hydroquinone monomethyl ether or other storage stabilizers in amounts which allow comparable stabilization.
  • an inert gas preferably an oxygen-containing gas, more preferably air or a mixture of air and nitrogen (lean air) may be circulated through or over the reaction mixture, for example in amounts of 0.1-1, preferably 0.2-0.8 and more preferably 0.3-0.7 m3 / m3h, based on the volume of the reaction mixture.
  • the course of the esterification a) can be followed by monitoring the amount of water discharged and / or the decrease in the concentration of carboxylic acid in the reactor.
  • the reaction can be terminated, for example, as soon as 90% of the theoretically expected amount of water has been discharged through the solvent, preferably at least 95% and particularly preferably at least 98%.
  • Removal of the reaction water can be omitted, for example, if the carboxylic acid B is used in a high stoichiometric excess, for example of at least 1.5: 1, preferably at least 2.5: 1 and very particularly preferably at least 5: 1. In this case, a substantial part of the resulting water remains close in the reaction mixture.
  • the proportion of water is removed from the reaction mixture, which is determined by the volatility at the applied temperature and, moreover, no measures for the separation of the resulting reaction water are carried out.
  • at least 10% by weight of the resulting water of reaction remain in the reaction mixture, preferably at least 20% by weight, more preferably at least 30% by weight, most preferably at least 40% and especially at least 50% by weight.
  • the reactor mixture can be cooled in the usual manner to a temperature of 10 to 30 ° C and optionally by adding solvent which is the same as the optionally for the azeotropic removal of water.
  • the reaction can be stopped with a suitable diluent G and brought to a concentration of, for example, 10 to 90% by weight, preferably 20 to 80%, more preferably 20 to 60%, very preferably 30 to 50% and especially diluted about 40%, for example, to reduce the viscosity.
  • a suitable diluent G preferably 10 to 90% by weight, preferably 20 to 80%, more preferably 20 to 60%, very preferably 30 to 50% and especially diluted about 40%, for example, to reduce the viscosity.
  • the diluent G is selected from the group consisting of water, a mixture of water with one or more indefinitely soluble organic solvents, or a mixture of water with one or more simple or higher functionality alcohols, e.g. Methanol and glycerin.
  • the alcohols preferably carry 1, 2 or 3 hydroxy groups and have preferably between 1 and 10, in particular up to 4, carbon atoms. Preference is given to primary and secondary alcohols.
  • Preferred alcohols are methanol, ethanol, isopropanol, ethylene glycol, 1, 2-propanediol or 1, 3-propanediol. 35 d) If necessary, the reaction mixture may be discolored, for example by treatment with activated charcoal or metal oxides, e.g. Alumina, silica, magnesia, zirconia, boria or mixtures thereof, in amounts of, for example, 0.1-
  • the reaction mixture may further be subjected to a pre-wash e) and / or a neutralization f) and / or a post-wash g), preferably only a neutralization f).
  • neutralization f) and prewash e) can also be reversed in the order.
  • carboxylic acid B for example (meth) acrylic acid and / or catalyst C can be at least partially recovered by acidification and extraction with a solvent and used again.
  • the reaction mixture is in a washing machine with a washing liquid, for example water or a 5 to 30% by weight, preferably 5 to 20, particularly preferably 5 to 15% by weight sodium chloride, potassium chloride , Ammonium chloride, sodium sulfate or ammonium sulfate solution, preferably water or saline.
  • a washing liquid for example water or a 5 to 30% by weight, preferably 5 to 20, particularly preferably 5 to 15% by weight sodium chloride, potassium chloride , Ammonium chloride, sodium sulfate or ammonium sulfate solution, preferably water or saline.
  • the quantitative ratio of reaction mixture: washing liquid is generally 1: 0.1-1, preferably 1: 0.2-0.8, particularly preferably 1: 0.3-0.7.
  • Prewash e is preferably used when metal salts, preferably copper or copper salts, are used as inhibitors (with).
  • the addition of the base takes place in such a way that the temperature in the apparatus does not rise above 60 ° C, preferably between 20 and 35 ° C and the pH is 4-13.
  • the dissipation of the heat of neutralization is preferably carried out by cooling the container with the aid of internal cooling coils or by double-wall cooling.
  • a solvent is contained in the reaction mixture, this can be substantially removed by distillation. Preference is given to optionally containing solvent after weighing. see and / or neutralization removed from the reaction mixture, if desired, but this can also be done before washing or neutralization.
  • Storage stabilizer preferably hydroquinone monomethyl ether added that after removal of the solvent 100-500, preferably 200-500 and more preferably 200-400 ppm thereof in the final ester (residue) are included.
  • an inert gas preferably an oxygen-containing gas, more preferably air or a mixture of air and nitrogen (lean air) can be introduced into the distillation apparatus, for example 0.1-1, preferably 0.2-0.8 and particularly preferably 0, 3 - 0.7 m3 / m3h, based on the volume of the reaction mixture.
  • the residual solvent content in the residue is after the
  • trays bubble-cap trays, sieve trays, valve trays, Thormann trays and / or dual-flow trays are preferred; of the trays are those with rings, coils, calipers, Raschig, Intos or Pall rings, Barrel or Intalox saddles, Top-Pak etc. or braids, preferred.
  • the carboxylic acid B contained in the reaction mixture is preferably not more than 75% by weight, more preferably not more than 50% by weight, very preferably not more than 25% by weight, in particular not more than 10% by weight and especially not more separated from the reaction mixture as 5% by weight, based on the carboxylic acid B present in the reaction mixture after the end of the reaction.
  • step b) can be dispensed with, so that only the proportion of water of reaction and carboxylic acid B is removed from the reaction mixture, which is determined by the volatility at the applied temperature. This can preferably be prevented by substantially complete condensation.
  • the reaction mixture thus obtained preferably has an acid number gem.
  • the reaction mixture can be diluted in step c), in which case it is preferably reacted within 6 hours, more preferably within 3 hours to the hydrogel. Preferably, it can be neutralized in a step f).
  • Ester F in the substance mixture 0.1 to 40% by weight, particularly preferably 0.5 to 20, very particularly preferably 1 to 10, in particular 2 to 5 and especially 2 to 4% by weight, - carboxylic acid B 0.5 99.9% by weight, particularly preferably 0.5-50% by weight, very particularly preferably 1-25, in particular 2-15 and especially 3 to 5% by weight,
  • Polymerization inhibitor D 0-5% by weight, more preferably 0.01
  • reaction mixture from the esterification including their work-up steps, if they are passed through, for example, the reaction mixture of f), or, if omitted f), from b), or, if omitted on b), the reaction mixture from a
  • N may be added with additional monoethylenically unsaturated compounds N which carry no acid groups but are copolymerizable with the hydrophilic monomers M may then be polymerized to produce water-absorbing hydrogels in the presence of at least one radical initiator K and optionally at least one grafting base L.
  • R 3 is hydrogen, methyl or ethyl
  • R 6 is hydrogen, amino or hydroxy- (C ⁇ -C) -alkyl
  • organic peroxides such as benzoyl peroxide, tert. Butyl hydroperoxide, methyl ethyl ketone peroxide, cumene hydroperoxide, azo compounds such as azobisisobutyronitrile and inorganic peroxy compounds such as (NH) 2 S 2 0s. KS 2 0s or H0 2 .
  • the present invention furthermore relates to crosslinked hydrogels which comprise at least one hydrophilic monomer M in a polymerized form and are crosslinked with an ester F of a polyhydric alcohol A with at least one ethylenically unsaturated carboxylic acid B.
  • the ester can be used according to the invention or in a prior art known manner are prepared, preferably in the inventive manner.
  • esters F are those of the formula VII, as defined above, in which y is independently of one another
  • the present invention further relates to the use of the above-mentioned hydrogel-forming polymers in sanitary articles comprising
  • (S) optionally a tissue layer located directly above and below the core (R) and (T) optionally a receiving layer located between (P) and (R).
  • hydrogel-forming polymer according to the invention 25, 32, 33, 34, 35, 36, 37, 38, 39 to 100% by weight of hydrogel-forming polymer according to the invention, more preferably 40, 41, 42, 43, 44, 45, 46, 47, 48 , 49 to 100% by weight of hydrogel-forming polymer according to the invention, in the more preferred range 50, 51, 52, 53, 54, 55, 56, 57, 58, 59 to 100% by weight of inventive
  • the liquid-impermeable layer (Q) is usually made of a film of polyethylene or polypropylene.
  • diapers The construction and the form of diapers is well known and is described, for example, in WO 95/26 209 p. 66, line 34 to p. 69, line 11, DE 196 04 601 A1, EP-A-0 316 518 and EP-A-A. 0 202 127 described.
  • diapers and other hygiene articles are also described in WO 00/65084, in particular on pages 6-15, WO 00/65348,
  • WO 95/24173 Absorbent Article for Controlling Odor, WO 91/11977: Body Fluid Odor Control, EP 389023: Absorbent Sanitary Articles, WO 94/25077: Odor Control Material, WO 97/01317: Absorbent Hygienic Article, WO 99/18905, EP 834297, US 5,762,644, US 5,895,381, WO 98/57609, WO
  • hydrogel-forming polymers according to the invention are outstandingly suitable as absorbents for water and aqueous liquids, so that they can be used advantageously as a water-retaining agent in agricultural horticulture, as a filtration aid and especially as an absorbent component in hygiene articles such as diapers, tampons or sanitary napkins.
  • Fiber materials of the absorbent composition are Fiber materials of the absorbent composition
  • thermoplastic polyvinyl lyolefinmaschinen such as polyethylene fibers (PULPEX®), polypropylene fibers and polyethylene-polypropylene bicomponent fibers, esterfasern poly-, such as polyethylene terephthalate (DACRON ® or K0 DEL®), copolyesters, polyvinyl acetate, polyethylvinyl acetate, polyvinyl chloride, polyvinylidene chloride , Polyacrylics, polyamides, copolyamides, polystyrene and copolymers of the abovementioned polymers, as well as two-component fibers of polyethylene terephthalate-polyethylene-isophthalate copolymer, polyethylvinyl acetate / polypropylene, polyethylene / polyester, polypropylene / polyester, copolyester / polyester, polyamide fibers (nylon) , Polyurethane fibers, polystyrene
  • thermoplastic fibers are preferably used in combination with thermoplastic fibers.
  • thermoplastic fibers During the heat treatment, the latter partly migrate into the matrix of the existing fiber material and thus form connecting points and renewed stiffening elements on cooling.
  • thermoplastic fibers means an extension of the pore dimensions present after heat treatment. In this way it is possible, by continuously adding thermoplastic fibers during the formation of the absorption layer, to continuously increase the proportion of thermoplastic fibers to the cover sheet, resulting in a likewise continuous increase in pore sizes.
  • Thermoplastic fibers can be formed from a variety of thermoplastic polymers having a melting point of less than 190 ° C, preferably between 75 ° C and 175 ° C. At these temperatures, no damage to the cellulose fibers is to be expected.
  • the fibers in the absorbent composition of the present invention may be hydrophilic, hydrophobic or a combination of both.
  • a fiber is said to be hydrophilic when the contact angle between the liquid and the fiber (or its surface) is smaller than 90 2 , or if the liquid tends to spit spontaneously on the same surface. Both processes are usually coexistent.
  • a fiber is said to be hydrophobic if a contact angle of greater than 90 ° is formed and no spreading is observed. Preference is given to using hydrophilic fiber material.
  • Suitable hydrophilic fibers for use in the absorbent composition according to the invention are, for example
  • Suitable hydrophilic fibers can also be obtained by hydrophilizing hydrophobic fibers, such as, for example, treating thermoplastic fibers obtained from polyolefins (such as polyethylene or polypropylene, polyamides, polystyrenes, polyurethanes, etc.) with surfactants or silica. For reasons of cost and availability, however, cellulose fibers are preferred.
  • the highly swellable hydrogel particles are embedded in the described fiber material. This can be done in many ways by z. B. with the hydrogel material and the fibers together builds up an absorption layer in the form of a matrix, or by incorporation harnesslCher hydrogels in layers of fiber mixture, where they are finally fixed, either by adhesive or lamination of the layers.
  • Mixture of synthetic fiber and cellulose fiber, wherein the mixing ratio of (100 to 0) synthetic fiber: (0 to 100) cellulose fiber can vary.
  • the cellulose fibers used can additionally be chemically stiffened to increase the dimensional stability of the hygiene article.
  • Chemically crosslinked cellulose fibers are known and known in
  • Examples of methods of obtaining an absorbent composition consisting of, for example, a support material to which one or both sides highly swellable hydrogels are fixed are known and included in, but not limited to, the invention.
  • the duration of the heat treatment depends on the type of synthetic fiber, its quantity and the speed of production of the hygiene article. In general, the duration of the heat treatment is between 0.5 second and 3 minutes, preferably 1 second to 1 minute.
  • the absorbent composition is generally provided, for example, with a liquid permeable cover layer and a liquid impermeable backsheet.
  • leg cuffs and adhesive tapes are applied, thus completing the hygiene article.
  • the materials and types of the permeable topsheet and impermeable backsheet, as well as the leg seals and tapes are well known to those skilled in the art and not particularly limited. Examples of this can be found in WO 95/26 209.
  • the advantage of the present invention resides in the fact that the esters F which can be used as crosslinkers do not have to be purified after their preparation, especially that the carboxylic acid B, for example acrylic acid, does not have to be separated off, since this usually constitutes a monomer for preparing the hydrogels.
  • Example 8 (about 5 times per glycerol molecule ethoxylated glycerol triacrylate)
  • Example 9 (about 9 times per glycerol molecule ethoxylated glycerol triacrylate)
  • Example 11 (about 13 times per molecule of ethoxylated dipentaerythritol)
  • Example 12 (about 4 times per molecule of ethoxylated sorbitol acrylate)
  • Example 13 (about 6 times per molecule of ethoxylated sorbitol acrylate)
  • Example 15 (about 10 times per molecule of ethoxylated sorbitol 15 acrylate)
  • the product is cleaned via K300 filter.
  • the acid number was 78 mg KOH / g.
  • the viscosity of the dark colored product was 406 mPas.
  • the measuring cell for determining the AUL 0.7 psi represents a Plexiglas cylinder with an inner diameter of 60 mm and a height of 50 mm, which has on the underside a glued stainless steel sieve bottom with a mesh size of 36 ⁇ .
  • the measuring cell also includes a plastic plate with a diameter of 59 mm and a weight, which can be placed together with the plastic plate in the measuring cell. The weight of the plastic plate and the weight together amount to 1345g.
  • the weight of the empty Plexiglas cylinder and the plastic plate is determined and recorded as Where.
  • crosslinkers the types indicated in Table 1 were added in the amounts indicated there, in each case based on acrylic acid used. Thereafter, 0.28% by weight of sodium persulfate and 0.0056% by weight of ascorbic acid, based in each case on the acrylic acid monomer used, were added as the polymerization initiator.
  • the reaction started, and the temperature of the kneader shell was readjusted so that the heat of reaction was not dissipated through the jacket. This leads to an almost adiabatic heating of the reaction mixture, in which case the polymerization takes place with stirring. At the end of the reaction, the temperature is maintained for about an hour. Afterwards, a fine crumbly gel could be emptied.
  • the gel was dried for 3 h at 160 C in a convection oven, ground with a laboratory roller mill, and sieved at 100-850 microns. This is the normal base polymer of Table 1.
  • the dry normal base polymer powder was with a solution of 0.06 wt.% Ethylenglykoldiglycidylether (Nagase, Japan), 3.43 wt.% Water and 1.47 wt.% Propanediol-1, 2 -in each case based on the polymer under Stirring homogeneously sprayed.
  • the wet powder was then tempered in the oven at 150 C for 60 min. It was then sieved again at 850 microns to remove agglomerates.
  • the properties of this postcrosslinked polymer were determined and are listed in Table 1.

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Polyesters Or Polycarbonates (AREA)
PCT/EP2003/005940 2002-06-11 2003-06-06 Verfahren zur herstellung von estern von polyalkoholen Ceased WO2003104299A1 (de)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2004511365A JP2005533875A (ja) 2002-06-11 2003-06-06 多価アルコールのエステルの製造法
AU2003242636A AU2003242636A1 (en) 2002-06-11 2003-06-06 Method for the production of esters of polyalcohols
BRPI0311500-3A BR0311500B1 (pt) 2002-06-11 2003-06-06 processos para preparar um Éster f, e um hidrogel reticulado, polÍmero, hidrogel reticulado, uso de um polÍmero, composiÇço de matÉria, e, uso de uma mistura.
US10/514,569 US7250481B2 (en) 2002-06-11 2003-06-06 Method for the production of esters of polyalcohols
MXPA04012091A MXPA04012091A (es) 2002-06-11 2003-06-06 Preparacion de esteres de polialcoholes.
EP03757035A EP1516010B1 (de) 2002-06-11 2003-06-06 Verfahren zur herstellung eines vernetzten hydrogels

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10225943.7 2002-06-11
DE10225943A DE10225943A1 (de) 2002-06-11 2002-06-11 Verfahren zur Herstellung von Estern von Polyalkoholen

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CN (1) CN1659212A (https=)
AU (1) AU2003242636A1 (https=)
BR (1) BR0311500B1 (https=)
DE (1) DE10225943A1 (https=)
MX (1) MXPA04012091A (https=)
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Cited By (211)

* Cited by examiner, † Cited by third party
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