WO2000023651A1 - Dispersions aqueuses d'agents d'encollage ajustees de maniere a etre anioniques ou cationiques pour l'encollage de papier - Google Patents

Dispersions aqueuses d'agents d'encollage ajustees de maniere a etre anioniques ou cationiques pour l'encollage de papier Download PDF

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WO2000023651A1
WO2000023651A1 PCT/EP1999/007363 EP9907363W WO0023651A1 WO 2000023651 A1 WO2000023651 A1 WO 2000023651A1 EP 9907363 W EP9907363 W EP 9907363W WO 0023651 A1 WO0023651 A1 WO 0023651A1
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Prior art keywords
sizing agent
acid
aqueous
anionic
formaldehyde
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PCT/EP1999/007363
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German (de)
English (en)
Inventor
Nicole Ofenloch
Udo Wendel
Axel Kistenmacher
Johann Bonn
Rudolf Schuhmacher
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Basf Aktiengesellschaft
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Priority claimed from DE19847824A external-priority patent/DE19847824A1/de
Priority claimed from DE19847825A external-priority patent/DE19847825A1/de
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU63335/99A priority Critical patent/AU6333599A/en
Publication of WO2000023651A1 publication Critical patent/WO2000023651A1/fr

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • D06M15/233—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated aromatic, e.g. styrene
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof
    • D06M15/33—Esters containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/347—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3566—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing sulfur
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/16—Sizing or water-repelling agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/14—Carboxylic acids; Derivatives thereof
    • D21H17/15—Polycarboxylic acids, e.g. maleic acid
    • D21H17/16—Addition products thereof with hydrocarbons
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/17—Ketenes, e.g. ketene dimers
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
    • D21H17/42—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups anionic
    • D21H17/43—Carboxyl groups or derivatives thereof
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/47—Condensation polymers of aldehydes or ketones

Definitions

  • the invention relates to aqueous, anionically sized sizing agent dispersions which can be obtained by dispersing a sizing agent based on alkyldiketenes, alkenylsuccinic anhydrides and / or resin sizes in the presence of an anionic dispersant in water for the sizing of paper.
  • sizing agents contain, for example, alkyldiketenes in the form of a dispersion which is stabilized with the aid of cationic starch.
  • the solids content of such dispersions is, for example, on the order of between 6 and 20% by weight, based on alkyl diketene.
  • aqueous alkyldiketene dispersions which contain up to 30% by weight of alkyldiketene in dispersed form.
  • Other essential components of these alkyldiketene dispersions are cationic starch, preferably cationic waxy maize starch, aluminum sulfate, carboxylic acids with 1 to 10 carbon atoms, and sulfonates such as the sodium salt of lignosulfonic acid or condensation products of formaldehyde and naphthalenesulfonic acid, cf. US-A-4861376 and EP-B-0369328.
  • Aqueous dispersions of a reactive sizing agent based on alkyldiketenes are known from EP-A-0418015.
  • the size dispersions can then also be prepared by dispersing alkyldiketenes in water in the presence of anionic dispersants as the sole stabilizer for the dispersion.
  • anionic dispersants as the sole stabilizer for the dispersion.
  • Sodium lignin sulfonate and naphthalenesulfonic acid are used, for example, as anionic dispersants.
  • the content of dispersed alkyldiketene in the sizing mixture is 5 to 20, preferably 10 to 15,% by weight.
  • Stabilized aqueous alkyldiketene dispersions are known from EP-B-0 437 764 which, in addition to an alkyldiketene, contain a protective colloid and an ester of a long-chain carboxylic acid and a long-chain alcohol. Cationic starches are preferred as the protective colloid. Sorbitan esters, soaps, synthetic detergents and thickeners such as polymers of acrylamide, vinyl pyrrolidone and N-vinyl-2-methylimidazoline can also be used. Stable, highly concentrated aqueous dispersions of water repellents are known from US-A-5403392.
  • the content of water repellents such as alkyldiketenes, can be up to 50% by weight, based on the dispersion.
  • the dispersions contain, for example, saponins as stabilizers.
  • the known highly concentrated diketene dispersions are still in need of improvement.
  • the invention has for its object to provide new aqueous size dispersions which have a higher storage stability and a higher concentration than the known dispersions.
  • aqueous, anionically sized sizing agent dispersions which can be obtained by dispersing a sizing agent based on alkyldiketenes, alkenyl succinic anhydrides and / or resin sizes in the presence of an anionic dispersant in water, for sizing paper, if they at least one condensation product as the anionic dispersant
  • the anionic dispersants in question are preferably used in an amount of 0.1 to 5.0% by weight, based on the sizing agent.
  • alkyl diketenes can be used as sizing agents for producing the dispersions.
  • the long-chain alkyldiketenes commonly used as sizing agents are prepared, for example, from the corresponding saturated or unsaturated carboxylic acid chlorides by splitting off hydrogen chloride with tertiary amines.
  • the alkyldiketenes preferably contain 12 to 22 carbon atoms in the alkyl group.
  • Suitable alkyldiketenes are, for example, tetradecyldiketene, palmityldiketene, oleyldiketene, stearyldiketene and behenyldiketene.
  • Diketenes with different alkyl groups are also suitable, for example stearylpalmityldiketene, behenylstearyldiketene, behenyloleyldiketene or palmitylbehenyldiketene.
  • Stearyldiketene, palmityldiketene, behenyldiketene or mixtures of stearyldiketene and palmityldiketene or mixture of behenyldiketene or stearyldiketene are preferably used.
  • Alkenylsuccinic anhydrides contain, for example, a C ⁇ - to C - ⁇ -01efinrest, preferably a residue of C ⁇ - to Cis- ⁇ -olefins in the alkenyl group.
  • Resin glue includes naturally occurring products and modified resin glue, which can be obtained, for example, by reacting resin glue with maleic anhydride.
  • the alkyldiketenes and / or resin glues which are suitable as sizing agents are in a solid state at room temperature. To produce size dispersions, these sizes are usually heated to a temperature above their melting point and emulsified in molten form in water under the action of shear forces.
  • the liquid alkenyl succinic anhydride can be emulsified at room temperature. For this one uses e.g. Homogenizers.
  • at least one anionic dispersant from the group of condensation products is used according to the invention
  • the anionic dispersants can be in the form of the free acids, the alkali metal, alkaline earth metal and / or the ammonium salts.
  • the ammonium salts can be derived from ammonia as well as from primary, secondary and tertiary amines, for example the ammonium salts of dimethylamine, trimethylamine, hexylamine, cyclohexylamine, dicyclohexylamine, ethanolamine, diethanolamine and triethanolamine are suitable.
  • the condensation products described above are known and commercially available. They are prepared by condensing the above-mentioned components, wherein, in place of the free acids • the corresponding alkali metal, alkaline earth metal or ammonium salts can be used.
  • Acids such as sulfuric acid, p-toluenesulfonic acid and phosphoric acid are suitable as catalysts in the condensation.
  • Naphthalenesulfonic acid or its alkali metal salts are preferably condensed with formaldehyde in a molar ratio of 1: 0.1 to 1: 2 and usually in a molar ratio of 1: 0.5 to 1: 1.
  • the molar ratio for the production of condensates from phenol, phenolsulfonic acid and formaldehyde is also in the range given above, with any mixtures of phenol and phenolsulfonic acid being used instead of naphthalenesulfonic acid in the condensation with formaldehyde.
  • phenolsulfonic acid instead of phenolsulfonic acid, one can also use the alkali metal and ammonium salts of phenolsulfonic acid.
  • the condensation of the starting materials indicated above * can optionally also be carried out in the presence of urea.
  • urea based on naphthalenesulfonic acid or on the mixture of phenol and phenolsulfonic acid, 0.1 to 5 moles of urea are used per mole of naphthalenesulfonic acid or per mole of the mixture of phenol and phenolsulfonic acid.
  • the condensation products have, for example, molar masses in the range from 800 to 100,000, preferably 1,000 to 30,000 and in particular 4,000 to 25,000.
  • the anionic dispersants used are preferably salts which are obtained, for example, by neutralizing the condensation products with lithium hydroxide, sodium hydroxide, Potassium hydroxide or ammonia.
  • the pH of the salts is, for example, in the range from 7 to 10.
  • Amphiphilic copolymers are also suitable as anionic dispersants
  • hydrophilic monomers with an anionic group such as monoethylenically unsaturated carboxylic acids, monoethylenically unsaturated sulfonic acids, monoethylenically unsaturated phosphonic acids or mixtures thereof.
  • (a) are, for example, olefins with 2 to 150 C atoms, styrene, ⁇ -methylstyrene, ethylstyrene, 4-methylstyrene, acrylonitrile, methacrylonitrile, esters of monoethylenically unsaturated C 3 to C 5 carboxylic acids and monohydric alcohols, amides
  • Acrylic acid or methacrylic acid with -C ⁇ to C 2 alkylamines vinyl esters of saturated monocarboxylic acids with 2 to 24 C- Atoms, diesters of maleic acid or fumaric acid with monohydric C 1 -C 2 alcohols, vinyl ethers of alcohols with 3 to 24 C atoms or mixtures of the compounds mentioned.
  • amphiphilic copolymers contain, as hydrophilic monomers (b), for example C 3 -C 1 -C 1 -monoethylenically unsaturated carboxylic acids or their anhydrides, 2-acrylamido-2-methylpropanesulfonic acid, vinylsulfonic acid, styrenesulfonic acid, vinylphosphonic acid, salts of the stated monomers or mixtures thereof as hydrophilic monomers with a anionic group
  • Aqueous size dispersions which are amphiphilic copolymers as anionic dispersants are particularly preferred
  • Suitable hydrophobic monomers are, for example, linear, branched or cyclic olefins having 2 to 150 carbon atoms, such as, for example, ethene, propene, butene-1, isobutene, pentene-1, 3-methylbutene-1, 2-methylbutene-1, cyclopentene , Hexen-1, 2-methyl-pentene-1, 3-methyl-pentene-1, 4-methyl-pentene, 2-ethylbutene-1, cyclohexene, methylcyclopentene, hepten-1, methylcyclohexene, octene-1, 2,, 4 -trimethylpentene- 1, 2, 4, 4 -trimethylpentene-2,
  • Examples of these are: technically easily accessible olefin mixtures, Cs cuts (containing pentene derivatives and cyclopentene), technical diisobutene (containing, inter alia, 2, 4, 4-trimethylpentene-1 and 2, 4, 4-trimethylpentene-2), processed Diisobutene with proportions of> 70% by weight at 2, 4, 4-trimethylpentene-1 or with> 80% by weight of 2,4,4-trimethylpentene-1, C 8 - ⁇ o- ⁇ _ 01efine, C ⁇ 0 - ⁇ 2 - ⁇ -olefins, C 12 - i - ⁇ -01efine, C ⁇ 4 - ⁇ 8 - ⁇ -01efine, C ⁇ 8 - 22 - ⁇ -01efine, C 20 - 24 - ⁇ -olefins, C 24 - 28 - ⁇ -olefins and C 3 n- ⁇ -01efine.
  • hydrophobic monomers are aromatic olefins such as styrene, ⁇ -methylstyrene, 4-methylstyrene, indole. This group of monomers is preferably used with other hydrophobic monomers and is present in the polymer to less than 50% by weight of the total of the hydrophobic monomers polymerized in the polymer.
  • hydrophobic monomers are esters of acrylic acid and methacrylic acid with monohydric alcohols or alcohol mixtures with 1 ⁇ to 14 carbon atoms, such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, i-butyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, esters of acrylic acid and methacrylic acid with alkoxylated alcohols on alcohols with 3 to 24 carbon atoms or alkoxylated alcohol mixtures based on alcohols with 3 to 24 carbon atoms, such as for example butyl diglycol (meth) acrylate, lauryl tripropylene glycol (meth) acrylate,
  • hydrophobic monomers are amides of acrylic acid and methacrylic acid with C 3 -C 4 -alkylamines, vinyl esters of saturated carboxylic acids with 2 to 24 carbon atoms, such as vinyl acetate, vinyl propionate or vinyl butyrate, and diesters of maleic acid or fumaric acid with alcohols with monohydric 1 up to 24 carbon atoms such as dimethyl maleate or diethyl fumarate.
  • hydrophobic monomers are vinyl ethers of alcohols having 3 to 24 carbon atoms, such as propyl vinyl ether, butyl vinyl ether or lauryl vinyl ether.
  • hydrophilic monomers are C 3 -C 10 -monoethylenically unsaturated carboxylic acids or their anhydrides, for example acrylic acid, methacrylic acid, acrylic anhydride, methacrylic anhydride, maleic acid, maleic anhydride, fumaric acid, crotonic acid, itaconic acid, itaconic anhydride, citraconic acid, mesaconic acid, mesaconic acid, mesaconic acid , 1, 2, 3, 6-tetrahydrophthalic anhydride, 2-acrylamido-2-methyl propane sulfonic acid, vinyl sulfonic acid, styrene sulfonic acid and salts of the monomers mentioned.
  • the hydrophilic monomers are soluble in water or dissolve in a form partially or completely neutralized with bases.
  • water-soluble monomers are to be understood to mean all hydrophilic monomers which have a Have water solubility at 20 ° C of more than 20 g / 1.
  • Alkali metal bases, alkaline earth metal bases and ammonia or amines are used, for example, to prepare the salts of the hydrophilic monomers.
  • Preferred salts of the hydrophilic monomers are the sodium and potassium salts and the ammonium salts, which can be obtained by neutralizing the acid groups of the monomers with ammonia.
  • hydrophilic monomers are, for example, half-esters of maleic acid and alcohols having 1 to 25 carbon atoms or alkoxylation products of such alcohols and half-amides of maleic acid.
  • Preferred anionic dispersants are copolymers of maleic anhydride with C 4 - to -C 2 -01efins, particularly preferably Cs-olefins such as octene-1 and diisobutene. Diisobutene is very particularly preferred.
  • the molar ratio between maleic anhydride and olefin is, for example, in the range from 0.9: 1 to 3: 1, preferably from 0.95: 1 to 1.5: 1.
  • These copolymers are preferably in hydrolyzed form as an aqueous solution or
  • Dispersions used, wherein the anhydride group is open and the carboxyl groups are preferably partially or completely neutralized.
  • the following bases are used for neutralization: alkali metal bases, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, alkaline earth metal salts such as calcium hydroxide, calcium carbonate, magnesium hydroxide, ammonia, primary, secondary or tertiary amines such as triethylamine, triethanolamine, diethanolamine, ethanolamine, morpholine, etc.
  • alkali metal bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate
  • alkaline earth metal salts such as calcium hydroxide, calcium carbonate, magnesium hydroxide, ammonia, primary, secondary or tertiary amines such as triethylamine, triethanolamine, diethanolamine, ethanolamine, morpholine, etc.
  • the preferred copolymers of maleic anhydride with C 4 -01 -01efins are
  • the copolymers are prepared by known processes of free-radical polymerization, such as, for example, solution polymerization, emulsion polymerization, dispersion polymerization, precipitation polymerization, melt polymerization.
  • Suitable solvents or diluents are the customary compounds, such as water, alcohols, ketones, esters, aliphatics, aromatics or mixtures such as water / isopropanol mixtures.
  • One or more of the monomers can also be used as the solvent or diluent, or the use of a solvent or diluent can be dispensed with entirely.
  • the polymerizations can be carried out either as a Batc reaction or with one or more feeds.
  • the inflow times and the quantities per unit time of individual components can be varied. Characteristics such as copolymer composition, average molecular weight or the molecular weight distribution can be controlled in a characteristic manner.
  • the polymerization can be carried out in the presence of so-called regulator compounds, by means of which the average molecular weight can be reduced.
  • regulators that can be used are: 2-mercaptoethanol, 2-mercaptopropanol, mercatoacetic acid, tert. Butyl mercaptan, n-octyl mercaptan, n-decyl mercaptan and tert. -Dodecyl mercaptan. Ci to C 4 aldehydes and formic acid can also be used for this.
  • the polymerization can optionally be carried out in the presence of another group of monomers (c) which are hydrophilic and are nonionic or hydrophilic and cationic, e.g. Acrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylimidazole, N-vinylmethylimidazole, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, methylpolyethylene glycol (meth) acrylate, dirnethylaminopropylmethacrylamide, dirnethylaminoethylacryla, methyl vinyl ether, N-vinyl Allyl alcohol alkoxylates, vinyl imidazolium methosulfate.
  • monomers (c) which are hydrophilic and are nonionic or hydrophilic and cationic, e.g. Acrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, N
  • the cationic monomers are only polymerized in such an amount that the resulting copolymer has a net anionic charge.
  • the monomers of group (c) are present in the copolymer in copolymerized form in an amount of from 0 to 25% by weight.
  • the polymerization can optionally be carried out in the presence of crosslinking agents (monomers (d)).
  • crosslinking agents are, for example: divinylbenzene, perntaerythritol triallyl ether, esters of glycols such as glycol diacrylate, polyethylene glycol diacrylates.
  • the monomers (d) can be added during the polymerization in amounts of up to 5% by weight.
  • emulsifiers for example: sodium lauryl sulfate, alkoxylated fatty alcohols or oxo alcohols, block copolymers of ethyleneoxy and propyleneoxy units, alkoxylated fatty acids, ethoxylated fatty acid amides, fatty acid alkanolamides, fatty acid ammonium salts, fatty alcohol phosphates, alkyl glucosides, alkyl phenol alkoxylates or sulphonic acid mononyl alcoholsulfonates or sulfonic acid monoesters N-acylamino acids or mixtures or polyvinyl alcohol, degraded starch, modified Starches, carboxy ethyl cellulose, hydroxyethyl
  • the radical initiators used are the compounds known in practice, which are selected, inter alia, on the basis of the intended polymerization temperature and the solvent or diluent used or the solubility behavior of the solvent-free system. For example, up to 10, preferably 0.2 to 5% by weight of these compounds, based on the monomers used in the copolymerization, are required.
  • Suitable polymerization initiators are, for example, peroxide compounds such as tert. Butyl perpivalate, tert. Butyl perneodecanoate, tert. Butyl perethyl hexanoate, tert. -Butyl perisobuyrate, di- * tert. -Butyl peroxide, di-tert.
  • -Amyl peroxide diacetyl peroxydicarbonate or dicyclohexyl peroxydicarbonate as well as azo compounds such as 2, 2 '-azobisisobutyronitrile.
  • the initiators can be used alone or as a mixture with one another.
  • Particularly preferred anionic dispersants are hydrolyzed copolymers of isobutene and maleic anhydride or their water-soluble salts.
  • hydrolyzed means that copolymers of isobutene and maleic anhydride are first prepared, which are hydrolyzed after the polymerization. Two carboxyl groups are obtained from an anhydride group in the copolymer.
  • Other preferred anionic dispersants are hydrolyzed copolymers of diisobutene and maleic acid or their water-soluble salts and copolymers of styrene and acrylic acid, hydrolyzed copolymers of styrene and maleic acid or the water-soluble salts of these copolymers.
  • amphiphilic copolymers in the form of the free acid are not sufficiently water-soluble, they are used in the form of water-soluble salts, for example the corresponding alkali metal, alkaline earth metal and ammonium salts are used.
  • the molar mass M w of the amphiphilic copolymers is, for example, 800 to 250,000, mostly 1,000 to 100,000 and is preferably in the range from 3,000 to 20,000, in particular from 1,500 to 10,000.
  • the acid numbers of the amphiphilic copolymers are, for example, 50 to 500, preferably 150 to 300 mg KOH / g polymer.
  • Preferred amphiphilic copolymers contain e.g.
  • Copolymers are particularly preferably used
  • the copolymers may optionally contain, as further monomers (c) units of maleic acid semi-esters in copolymerized form.
  • Such copolymers are obtainable, for example, by copolymerizing styrene, diisobutene or isobutene or mixtures thereof with maleic anhydride in the absence of water and reacting the copolymers with alcohols after the polymerization, with 5 to 50 mols per mole of anhydride groups in the copolymer. % of a monohydric alcohol. Suitable alcohols are, for example, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol and tert.
  • the anhydride groups of the copolymers can also be reacted with polyhydric alcohols such as glycol or glycerin. Here, however, the reaction is only carried out to such an extent that only one OH group of the polyhydric alcohol reacts with the anhydride group. If the anhydride groups of the copolymers are not completely reacted with alcohols, the anhydride groups not reacted with alcohols are opened by adding water.
  • amphiphilic copolymers are used, for example, in amounts of 0.05 to 20, preferably 0.5 to 10% by weight, based on the sizing agent, as an anionic dispersant for the production of the sizing agent dispersions.
  • the amphiphilic copolymers are preferably used in amounts of 0.1 to 2, in particular 0.6 to 1,% by weight, based on the sizing agent to be dispersed.
  • amphiphilic copoly- Merisates as dispersants are aqueous sizing dispersions which are formaldehyde-free and stable in storage.
  • aqueous, anionic sizing agent dispersions for example, an aqueous solution of at least one condensation product or at least one amphiphilic copolymer can be introduced and the sizing agent dispersed therein at temperatures of, for example, 20 to 100, preferably 40 to 90 ° C.
  • the sizing agent is preferably added in the form of a melt and dispersed with vigorous stirring or shearing. The resulting dispersion is cooled in each case.
  • aqueous, anionically sized sizing agent dispersions which contain 6 to 65% by weight of an alkyldiketene or 0.1 to 65% by weight of an alkenylsuccinic acid anhydride in dispersed form as a sizing agent.
  • sizing agent dispersions contain 25 to 60% by weight of an alkyldiketene as a sizing agent and 0.1 to 5.0% by weight of an amphiphilic copolymer
  • Such highly concentrated sizing agent dispersions have a relatively low viscosity, e.g. in the range of 20 to
  • the pH is, for example, from 2 to 8 and is preferably in the range from 3 to 4.
  • the invention also relates to a process for the preparation of aqueous, cationically sized sizing agent dispersions, in which first alkyldiketenes and / or alkenyl succinic anhydrides are present in the presence of at least one anionic dispersant from the group of the condensation products
  • dispersions thus obtainable are then diluted with water and transferred by adding at least one cationic additive to a cationically sized sizing agent dispersion.
  • the cationic additives which can be used are, for example, the cationic starches, cationic polymers and / or cationic condensates such as dicyandiamide-formaldehyde condensates which are customarily used for the preparation of alkyldiketene dispersions.
  • the cationic additives are used in such an amount that a net cationic sizing agent dispersion is obtained.
  • suitable additives are, for example, copolymers of acrylamide and basic monomers such as dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, dimethylaminopropyl acrylate and dimethylaminopropyl methacrylate.
  • the basic comonomers are in shape the free bases, as a salt with organic or inorganic acids or in quaternized form in the preparation of the copolymers.
  • Further cationic additives are polymers containing vinylamine units, such as polyvinylamine, or polymers containing vinylamine units which are obtainable from full or partial hydrolysis from poly-N-vinylformamide.
  • Other suitable cationic additives are polymers containing N-vinylimidazole units and Mannich-modified polyacrylamides, Hofmann degradation products of polyacrylamides, copolymers of diethyl dialkylammonium chloride and epichlorohydrin-modified polyamide polyamine resins, polyaluminum chloride and alum.
  • aqueous, anionically sized sizing agent dispersions or the cationically adjusted sizing agent dispersions obtainable therefrom after addition of cationic additives by reloading are used as mass and surface sizing agents in the production of paper, cardboard and cardboard and for the hydrophobization of cellulose fibers.
  • Highly concentrated aqueous size dispersions are usually diluted by adding water before use, so that the size can be metered better.
  • the sizing agents can be used in papermaking together with customary drainage and retention agents, flocculants, strengthening agents for paper and fixing agents. Those available with the anionic sizing agent dispersions
  • Sizing effects correspond to the degree of sizing which, for example, with the usual aqueous, cationically adjusted alkyldiketene dispersions has an alkyldiketene concentration of e.g. 6% by weight is reached.
  • the molecular weights M w were determined with the aid of gel permeation chromatography (GPC) in an aqueous medium with polyethylene oxide as the standard or by GPC in tetrahydrofuran as the mobile phase with polystyrene as the standard.
  • GPC gel permeation chromatography
  • the degree of sizing of the papers was determined with the aid of the ink floating time in accordance with DIN 53126 and with the aid of the Cobb value.
  • the approximately 50% aqueous sizing agent dispersion had an average particle size of 0.7 ⁇ m and a viscosity at a temperature of 20 ° C. of 30 mPas.
  • the viscosity of the diketene dispersion remained constant during 4 weeks of storage at room temperature.
  • the viscosity of the alkyl diketene dispersion thus obtained was 20 mPas at 20 ° C.
  • the average particle size of the dispersed sizing agent was 0.6 ⁇ m.
  • the viscosity of the alkyldiketene dispersion remained constant during 4 weeks of storage at room temperature.
  • composition 1 the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same as the same
  • EP-A-0418015 produced a 20% aqueous dispersion of an alkyl kentene dimer from palmitic acid and stearic acid in a molar ratio of 1: 2 by emulsifying the diketene mixture in an aqueous solution heated to 90 ° C., which 4.5% sodium lignin sulfonate and 1 , 25% contained naphthalenesulfonic acid.
  • the emulsion was homogenized in a homogenizer at a pressure of 150 bar and cooled to room temperature.
  • the viscosity of the 20% aqueous alkyldiketene dispersion thus obtained was 50 mPas at a temperature of 20 ° C.
  • the alkyldiketene dispersion was stored for 4 weeks at room temperature. There was no increase in viscosity. Comparative Example 2
  • Comparative Example 1 was repeated with the exception that a 35% alkyldiketene dispersion was prepared. When the dispersion cooled to room temperature, it became solid, so that a viscosity at 20 ° C. could not be determined. It was also not possible to test the sizing effect because the solid product obtained could no longer be diluted homogeneously.
  • Paper sheets with a basis weight of 80 g / m 2 were produced on a Rapid-Köthen sheet former.
  • the amounts of alkyl ketene dimer, based on dry fibrous material, given in Table 1, were added to the paper stock.
  • the leaves were stored for 48 hours at 23 ° C. and a relative air humidity of 50%. Then the Cobb value and the ink floating time up to 50% breakthrough in minutes were determined. The results obtained are shown in the table.
  • Stoffmodeil 1 consisted of 70% birch sulfate, 30% pine sulfate (separate grinding on 35 ° Schopper-Riegler), 20% chalk, 0.04% of a commercially available high-molecular polyacrylamide as retention agent and 0.6% of a cold-soluble cationic starch.
  • Substance model 2 contained calcium carbonate precipitated instead of chalk. Table 1
  • AKD alkyl diketene
  • the amount of water given in Table 2 and any other constituents that are given in Table 2 are mixed and heated to a temperature of 80 ° C. As soon as this temperature is reached, the amount of stearyldiketene given in Table 2 is added in the form of a melt and the mixture is homogenized with an Ultra -Turrax (stages 8 to 10, dispersion time 3 min.). The dispersion obtained was in each case within 15 min. cooled to room temperature with stirring. 2 parts of propionic acid are added during the cooling process.
  • amphiphilic copolymer in the form of an aqueous solution of the sodium salt of a copolymer of diisobutene and maleic anhydride (molar ratio 1: 1), molar mass M w 12,000 with a solids content of 25% by weight, was used as the dispersant.
  • Dispersant A Mixture of 2 parts naphthalene sulfonic acid-formaldehyde condensate and 1 part
  • aqueous size dispersions prepared according to Examples 10 to 16 and Comparative Examples 5 to 9 were tested for foam formation and storage stability. Foam formation was assessed visually during the dispersing process.
  • the ink float was determined in minutes up to a 50% breakdown in accordance with DIN 53126.
  • the ink floating time given in Table 4 was averaged for the top and screen sides for a sized paper made from wood-free sulfate pulp with chalk as a filler depending on the amount of sizing agent (% based on pulp).
  • the size dispersions were each stored for 24 hours before they were used for the size. The results are shown in Table 4. Table 4:
  • Table 6 shows the ink floating time in minutes (averaged for the top and screen side) on sized paper made from wood-containing sulfate cellulose as a function of the amount of sizing agent in%, based on the pulp.
  • the sizing agents were stored for 24 hours before the sizing was carried out.

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Abstract

L'invention concerne des dispersions aqueuses d'agents d'encollage ajustées de manière à être anioniques qui s'obtiennent par mise en dispersion d'un agent d'encollage à base de dicétènes d'alkyle, d'anhydride d'acide alcénylsuccinique et/de colles de résine, dans l'eau en présence d'un agent de dispersion anionique. Ces dispersions contiennent comme agent de dispersion anionique au moins un produit de condensation sélectionné dans le groupe comprenant (a) l'acide naphtalène-sulfonique et le formaldéhyde, (b) le phénol, l'acide phénolsulfonique et le formaldéhyde, (c) l'acide naphtalène-sulfonique, le formaldéhyde et l'urée, (d) le phénol, l'acide phénolsulfonique, le formaldéhyde et l'urée et/ou (e) au moins un copolymère amphiphile constitué (i) de monomères monoéthyléniquement insaturés, hydrophobes, et (ii) de monomères hydrophiles comportant un groupe anionique, dans des proportions comprises entre 0,05 et 10 % en poids, par rapport à l'agent d'encollage. L'invention concerne également la production de dispersions d'agents d'encollage ajustées de manière à être cationiques, à partir des dispersions anioniques mentionnées, par addition d'une proportion suffisante d'additifs cationiques. L'invention concerne en outre l'utilisation de ces dispersions anioniques et cationiques comme agent d'encollage pour le papier et le carton, ainsi que pour rendre des fibres de cellulose hydrophobes.
PCT/EP1999/007363 1998-10-16 1999-10-05 Dispersions aqueuses d'agents d'encollage ajustees de maniere a etre anioniques ou cationiques pour l'encollage de papier WO2000023651A1 (fr)

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DE19847824A DE19847824A1 (de) 1998-10-16 1998-10-16 Wäßrige Leimungsmittel-Dispersionen für die Leimung von Papier
DE19847825.9 1998-10-16
DE19847824.0 1998-10-16
DE19847825A DE19847825A1 (de) 1998-10-16 1998-10-16 Wäßrige, anionisch eingestellte Leimungsmittel-Dispersionen für die Leimung von Papier

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002012623A1 (fr) 2000-08-07 2002-02-14 Akzo Nobel N.V. Procede de collage de papier
WO2004022848A1 (fr) * 2002-08-14 2004-03-18 Basf Aktiengesellschaft Procede pour le collage de papier, carton-pate et carton
US6818100B2 (en) 2000-08-07 2004-11-16 Akzo Nobel N.V. Process for sizing paper
US7294190B2 (en) 2003-10-23 2007-11-13 Basf Aktiengesellschaft Mixtures of solids, consisting of a reactive sizing agent and starch, method for producing said mixtures and use thereof
WO2008100492A2 (fr) * 2007-02-12 2008-08-21 Hercules Incorporated Solution de collage a colophane dispersee stabilisee par alcanolamine et preparation associee
US7709052B2 (en) 2002-10-18 2010-05-04 Basf Aktiengesellschaft Aqueous polymer dispersions containing alkyldiketenes, methods for the production thereof, and their use

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DE2426038A1 (de) * 1970-09-08 1975-12-18 Hercules Inc Verfahren zur herstellung einer praktisch stabilen, waessrigen dispersion eines materials auf kolophoniumgrundlage.
DE2701760A1 (de) * 1977-01-18 1978-07-20 Bayer Ag Verfahren zur herstellung von papierleimungsmitteln
DE2951507A1 (de) * 1978-12-22 1980-07-03 Hercules Inc Papierleimstoffe
EP0056876A1 (fr) * 1980-12-31 1982-08-04 Hercules Incorporated Dispersions stables de colophane fortifiée
EP0208667A1 (fr) * 1985-07-10 1987-01-14 Eka Nobel Aktiebolag Dispersions aqueuses, procédé pour les préparer et usage des dispersions comme agents d'encollage
EP0418015A1 (fr) * 1989-09-11 1991-03-20 Eka Nobel Landskrona AB Compositions d'encollages actives
GB2268941A (en) * 1992-07-24 1994-01-26 Roe Lee Paper Chemicals Compan Rosin sizes
WO1998033979A1 (fr) * 1997-02-05 1998-08-06 Akzo Nobel N.V. Procede de collage de papier
WO1998033980A1 (fr) * 1997-02-05 1998-08-06 Akzo Nobel N.V. Dispersions aqueuses de materiau hydrophobe
WO1999037857A1 (fr) * 1998-01-26 1999-07-29 Krems Chemie Aktiengesellschaft Dispersions aqueuses stables destinees au collage du papier

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2426038A1 (de) * 1970-09-08 1975-12-18 Hercules Inc Verfahren zur herstellung einer praktisch stabilen, waessrigen dispersion eines materials auf kolophoniumgrundlage.
DE2701760A1 (de) * 1977-01-18 1978-07-20 Bayer Ag Verfahren zur herstellung von papierleimungsmitteln
DE2951507A1 (de) * 1978-12-22 1980-07-03 Hercules Inc Papierleimstoffe
EP0056876A1 (fr) * 1980-12-31 1982-08-04 Hercules Incorporated Dispersions stables de colophane fortifiée
EP0208667A1 (fr) * 1985-07-10 1987-01-14 Eka Nobel Aktiebolag Dispersions aqueuses, procédé pour les préparer et usage des dispersions comme agents d'encollage
EP0418015A1 (fr) * 1989-09-11 1991-03-20 Eka Nobel Landskrona AB Compositions d'encollages actives
GB2268941A (en) * 1992-07-24 1994-01-26 Roe Lee Paper Chemicals Compan Rosin sizes
WO1998033979A1 (fr) * 1997-02-05 1998-08-06 Akzo Nobel N.V. Procede de collage de papier
WO1998033980A1 (fr) * 1997-02-05 1998-08-06 Akzo Nobel N.V. Dispersions aqueuses de materiau hydrophobe
WO1999037857A1 (fr) * 1998-01-26 1999-07-29 Krems Chemie Aktiengesellschaft Dispersions aqueuses stables destinees au collage du papier

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002012623A1 (fr) 2000-08-07 2002-02-14 Akzo Nobel N.V. Procede de collage de papier
US6818100B2 (en) 2000-08-07 2004-11-16 Akzo Nobel N.V. Process for sizing paper
US6846384B2 (en) 2000-08-07 2005-01-25 Akzo Nobel N.V. Process for sizing paper
US7318881B2 (en) 2000-08-07 2008-01-15 Akzo Nobel N.V. Process for sizing paper
WO2004022848A1 (fr) * 2002-08-14 2004-03-18 Basf Aktiengesellschaft Procede pour le collage de papier, carton-pate et carton
US7709052B2 (en) 2002-10-18 2010-05-04 Basf Aktiengesellschaft Aqueous polymer dispersions containing alkyldiketenes, methods for the production thereof, and their use
US7294190B2 (en) 2003-10-23 2007-11-13 Basf Aktiengesellschaft Mixtures of solids, consisting of a reactive sizing agent and starch, method for producing said mixtures and use thereof
WO2008100492A2 (fr) * 2007-02-12 2008-08-21 Hercules Incorporated Solution de collage a colophane dispersee stabilisee par alcanolamine et preparation associee
WO2008100492A3 (fr) * 2007-02-12 2009-01-08 Hercules Inc Solution de collage a colophane dispersee stabilisee par alcanolamine et preparation associee
US7854800B2 (en) 2007-02-12 2010-12-21 Hercules Incorporated Alkanolamine-stabilized dispersed rosin sizing agents and their preparation

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