WO1991013926A1 - Composes contenant des chaines de polyether et des groupes quaternaires d'ammonium - Google Patents

Composes contenant des chaines de polyether et des groupes quaternaires d'ammonium Download PDF

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Publication number
WO1991013926A1
WO1991013926A1 PCT/EP1991/000376 EP9100376W WO9113926A1 WO 1991013926 A1 WO1991013926 A1 WO 1991013926A1 EP 9100376 W EP9100376 W EP 9100376W WO 9113926 A1 WO9113926 A1 WO 9113926A1
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WO
WIPO (PCT)
Prior art keywords
units
water
integer
compounds
quaternary ammonium
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Application number
PCT/EP1991/000376
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German (de)
English (en)
Inventor
Ralf Bohlander
Günter Uphues
Uwe Ploog
Maria Liphard
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1991013926A1 publication Critical patent/WO1991013926A1/fr

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Classifications

    • 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
    • D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
    • D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1405—Polycondensates modified by chemical after-treatment with inorganic compounds
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C5/00—Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
    • D21C5/02—Working-up waste paper
    • D21C5/025—De-inking
    • D21C5/027—Chemicals therefor
    • 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
    • D21H17/53—Polyethers; Polyesters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/64—Paper recycling

Definitions

  • the invention relates to water-soluble or water-dispersible compounds containing polyether chains and quaternary ammonium groups, a process for their preparation and the use of these compounds in waste paper processing.
  • waste paper For the production of, for example, newspaper printing and hygiene papers, waste paper is used in large quantities today. The quality of these types of paper is determined by their brightness and color. In order to be able to produce high-quality paper types, the printing inks must be removed from the printed waste paper. This is usually done using the deinking process, which essentially takes place in two steps:
  • the second process step can be carried out by washing or flotation (Ullmann's Enzyclopadie der Technischen Chemie, 4th edition, volume 17, pages 570-571 (1979)).
  • flotation in which the different wettability of printing inks and paper fibers is exploited, air is pressed or sucked through the pulp suspensions. Small air bubbles combine with the ink particles and form a foam on the surface of the water, which is removed with fabric hangers.
  • the deinking of waste paper is usually carried out at alkaline pH values in the presence of alkali hydroxides, alkali silicates, oxidative bleaches and surface-active substances at temperatures between 30 and 50 ° C.
  • Soaps and / or fatty alcohol polyglycol ethers are predominantly used as surface-active substances which bring about the detachment and separation of the printing ink particles (Ullmann's Enzyclopadie der Technischen Chemie, 4th edition, volume 17, pages 571-572 (1979)).
  • the German patent application DE-OS 33 22 330 and the German patent DE-PS 33 47 906 describe the use of alkylamine polyethers for removing printing ink. Furthermore, from JP 84/137587, referenced in Che. Abstr.
  • water-thinnable printing inks have decisive advantages over conventional solvent-based printing inks, there are still warnings about the introduction of processes using water-thinning printing inks (flexographic printing inks), since water-thinnable printing inks made from waste paper contain the usual surfactants from the deinking fleet - if at all - can only be removed completely inadequately (Das Textil 42 (10 A), V84-V88 (1988)). The consequence of this is that to date the waste paper that is being produced in ever larger quantities and that has been printed with water-thinnable printing inks has not been reused and is therefore not available as waste paper raw material for newsprint and hygiene paper.
  • the object on which the invention is based was to provide connections for deinking waste paper, with which it is possible to remove, in particular, satisfactory amounts of water-dilutable printing inks from waste paper.
  • the invention accordingly relates to water-soluble or water-dispersible compounds containing polyether chains and quaternary ammonium groups, obtainable by reacting halohydrin and / or epoxy compounds containing quaternary ammonium groups and
  • AO 1 to 100 alkylene oxide units which are composed of 0 to 100 C2H4 ⁇ units, 0 to 50 C3H5 ⁇ units and 0 to 30 C ⁇ gO units, shark chlorine and / or Bromine atoms
  • p is an integer between 0 and 3 and q 0 or 1, with the proviso that the sum p + q is not equal to 0 and z is an integer from 1 to 10,
  • ammonia aliphatic di- and / or polyamines and / or amino sugars.
  • Another subject matter of the invention is a process for the preparation of water-soluble or water-dispersible compounds containing polyether chains and quaternary ammonium groups, which is characterized in that halohydrin and / or epoxy compounds containing quaternary ammonium groups and Compounds of the general formula I
  • AO 1 to 100 alkylene oxide units which are composed of 0 to 100 C2H4 ⁇ units, 0 to 50 C3H ⁇ units and 0 to 30 CHgO units, shark chlorine and / or bromine atoms
  • p is an integer between 0 and 3 and q is 0 or 1, with the proviso that the sum p + q is not equal to 0, and z is an integer from 1 to 10,
  • the compounds described in DE-PS 38 03 213 have significantly lower molar masses and only have terminal quaternary ammonium groups and at least one oxirane group.
  • polyether chains and compounds containing quaternary ammonium groups can be obtained by reacting halohydrin and / or epoxy compounds containing quaternary ammonium groups and compounds of the general formula I with ammonia,
  • the alkali metal hydroxides used are, for example, sodium hydroxide and / or potassium hydroxide, preferably sodium hydroxide, and the reactions can be carried out with or without a solvent the reactions are carried out in aqueous, alcoholic or aqueous-alcoholic solutions.
  • the reactions are terminated by adding inorganic and / or organic acids, for example sulfuric acid, acetic acid and / or lactic acid.
  • aliphatic di- and / or polyamines can first be modified with halohydrin and / or epoxy compounds containing quaternary ammonium groups, 0.1 to 1 mol of these quaternary ammonium groups containing halohydrin and / or epoxy compounds per mole A be used. Modification means that some of the primary and secondary amine groups contained in the di- and / or polyamines are converted into the corresponding secondary and tertiary amine groups. The modified di- and / or polyamines are then reacted with compounds of the general formula I, optionally with the addition of NH compounds.
  • halohydrin and / or epoxy compounds containing quaternary ammonium groups are reacted together with compounds of the general formula I and NH compounds.
  • halohydrin and / or epoxy compounds containing quaternary ammonium groups are used in such amounts used that 1 to 30 mol% of the nitrogen atoms can be modified.
  • quaternary ammonium halogen-containing and / or epoxy compounds can be added after the reaction of the compounds of general formula I with NH compounds.
  • Halogen-hydrine and / or epoxy compounds containing quaternary ammonium groups are used in amounts such that 0.1 to 10 mol% of the amine nitrogen atoms originally present can be modified.
  • Suitable quaternary ammonium groups containing halohydrin and / or epoxy compounds are 2,3-epoxypropyltrimethylammonium chloride and / or 3-chloro-2-hydroxypropyltriethylammonium chloride. These compounds are commercially available products and are offered, for example, by Degussa under the name "QUAB”.
  • Compounds of the general formula I can be prepared from alcohols having 1 to 10 OH groups which are alkoxylated by known industrial processes with ethylene oxide, propylene oxide and / or butylene oxide ("Chemical Technology", Volume 7, pages 131-132, Carl-Hanser -Verlag, Kunststoff - Vienna 1986)).
  • the alkoxylated alcohols if desired in a mixture with the corresponding nonalkoxylated alcohols, are prepared with epihalohydrins, preferably with epichlorohydrin, preferably in the presence of catalysts, for example boron trifluoride diacetic acid and / or tin tetrachloride, at temperatures between 50 and 150 ° C. ⁇ preferably implemented between 60 and 95 ° C.
  • Epihalohydrins are used in amounts of 0.3 to 4 mol, based on an OH group.
  • Suitable alcohols with 1 to 10 OH groups are, for example, linear, branched-chain and / or cyclic, primary and / or secondary, monohydric alkyl alcohols with 1 to 22 carbon atoms, such as methanol, ethanol, butanol, isopropanol, cyclohexanol, 2-ethylhexanol and / or lauryl alcohol, dihydric alcohols of the general formula H0- (CH2) 2-12 ⁇ 0H ⁇ Bisphenol A, glycerol, di-, tri- and / or tetraglycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol and / or mannitol. Alcohols with 2 to 4 OH groups are preferred.
  • Suitable NH compounds are ammonia, C22 alkylamines, for example dodecylamine, 2-ethylhexylamine, coconut amine and / or tallow amine, aliphatic linear branched-chain and / or cyclic, optionally alkoxylated di- and / or polyamines with optionally amide groups in the aliphatic radicals , for example ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, dipropylenetriamine, dihexaethylenetriamine, 1,2-dihydroxyethyldiaminoethane, piperazine, polyethyleneamine with average molecular weights between 200 and 10,000, bis- [3,3-aminopropyl] methylamine, N, N-dimethylaminopropylamine, N-stearylpropylenediamine and / or N-acylamidoamine, which can be prepared by aminolysis of natural fats and / or oils or
  • Alkoxylated, preferably ethoxylated, di- and / or polyamines must have at least one N-H group.
  • Ci-22 "alkylamines and / or aliphatic di- and / or polyamines are preferably used.
  • the compounds of the invention which are accessible by reacting compounds of the general formula I and quaternary ammonium groups-containing halohydrin and / or epoxy compounds with NH compounds are aqueous solutions or with Gels which form aqueous solutions and contain the compounds according to the invention in amounts of 10 to 80% by weight, preferably 40 to 60% by weight.
  • the compounds according to the invention are suitable for removing water-dilutable and / or solvent-containing printing inks from printed waste paper and / or paper cycle water. Accordingly, the present invention relates to the use of water-soluble or water-dispersible compounds containing polyether chains and quaternary ammonium groups, obtainable by reacting halohydrin and / or epoxy compounds containing quaternary ammonium groups and
  • R is a z-valent alkoxy radical
  • AO 1 to 100 alkylene oxide units which are composed of 0 to 100 C2H4 ⁇ units, 0 to 50 C3H5 ⁇ units and 0 to 30 C4Hg0 units, shark chlorine and / or bromine atoms
  • the compounds according to the invention are added to paper stock suspensions, preferably in amounts of 0.02 to 2% by weight, particularly preferably from 0.1 to 0.5% by weight, in each case based on air-dry paper stock.
  • Air-dry paper stock means that an equilibrium state of internal moisture has occurred in the paper stock. This state of equilibrium depends on the temperature and the relative humidity of the air.
  • the deinking result the distance that is of printing inks from printed wastepaper, be increased when compounds of the invention in combination with spielmud C ⁇ o- 2 "F ett yarn ⁇ ⁇ w"> e 01inor R 4010, 01inor R 4020, and / or 01inor R DG40 (manufacturer of all Henkel KGaA products), ethoxylated alkyl alcohols with 6 to 22 carbon atoms, ethoxylated alkylphenols, polymers such as polyacrylamides and / or polydimethylaminoethyl methacrylates and / or copolymers, described, for example, in DE 3839479, in amounts of 0 , 01 to 1 wt .-%, based on air-dry paper stock, and / or with in situ precipitated layer compounds of the general composition
  • M (II) stands for divalent metal cations
  • M (III) for trivalent metal cations
  • a z ⁇ for anions of mono- and / or polybasic acids
  • the indices x a number between 0.01 and 0.5 and n is a number between 0 and 20, described in DE 39 09 568, are used.
  • the molar ratio of divalent metal cations to trivalent metal cations in layer compounds precipitated in situ is preferably between 20: 1 and 1: 1. Based on air-dry paper stock, trivalent metal cations can be used in amounts between 0.3 and 2% by weight.
  • water-thinnable and / or solvent-containing printing inks in particular water-thinning printing inks
  • solvent-containing printing inks for example newspaper rotary inks, letterpress printing inks, off-set printing inks, illustration gravure printing inks, flexographic printing inks, laser printing inks and / or packaging gravure inks from printed waste paper, for example newspapers, magazines, computer papers, magazines, brochures, forms, telephone books and / or catalogs.
  • the waste papers deinked by the process according to the invention are distinguished by very high degrees of whiteness.
  • Printed waste papers are, for example, between 1 and 5% by weight in a cloth dissolver in aqueous solution, typically 0 to 1.5% by weight hydrogen peroxide (100%), 0 to 2.5% by weight 99% .-% NaOH and 0 to 4.0 wt .-% soda water glass with a solids content of 35 wt .-% (37 to 40 ⁇ Be) - all wt .-% refer to air-dry paper - contains Crushed temperatures between 20 and 60 ° C. The pulp suspensions are then stirred into water or water is added, so that 0.6 to 1.6% by weight pulp suspensions are obtained.
  • printing inks are removed both from the waste paper and from the circulating water.
  • the compounds according to the invention can also be used for the separate cleaning of paper circulation waters. In these cases, after the addition of 2 to 100 mg of compounds according to the invention per liter of circulating water, the ink particles are removed, for example by filtration or flotation.
  • AI 330 g (1 mol) of QUAB 181 (a 60% strength by weight aqueous solution of 3-chloro-2-hydroxypropyltrimethylammonium chloride) were added to 131 g (1 mol) of dipropylenetriamine at 60 to 70 ° C. in the course of 2 hours. given and then stirred at this temperature for one hour.
  • reaction was then ended by adding 10 g of 98% strength by weight acetic acid and 30 g of water. A clear, 50% by weight solution with a viscosity (measured at 20 ° C. according to Höppler) of 6,500 mPas was obtained.
  • R457 R457 R457 DEM (%) T (%) compounds according to the invention used (US) (BS) (DS) according to the example

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Inorganic Chemistry (AREA)
  • Paper (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

L'invention concerne des composés solubles ou dispersibles dans l'eau qui contiennent des chaînes de polyéther et des groupes quaternaires d'ammonium, leur procédé de production et leur utilisation dans le recyclage de vieux papiers.
PCT/EP1991/000376 1990-03-09 1991-03-01 Composes contenant des chaines de polyether et des groupes quaternaires d'ammonium WO1991013926A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19904007597 DE4007597A1 (de) 1990-03-09 1990-03-09 Wasserloesliche oder wasserdispergierbare, polyetherketten und quaternaere ammoniumgruppen enthaltende verbindungen
DEP4007597.4 1990-03-09

Publications (1)

Publication Number Publication Date
WO1991013926A1 true WO1991013926A1 (fr) 1991-09-19

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AU (1) AU7333891A (fr)
DE (1) DE4007597A1 (fr)
WO (1) WO1991013926A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10320631A1 (de) 2003-05-08 2004-12-09 Wacker-Chemie Gmbh Polyalkoxyreste aufweisende Organosiliciumverbindungen
US7169257B2 (en) 2003-11-12 2007-01-30 Kemira Chemicals, Inc. Method of deinking waste paper using a reduced alkali system

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2733973A1 (de) * 1977-07-28 1979-02-15 Basf Ag Wasserloesliche, vernetzte stickstoffhaltige kondensationsprodukte
DE2610277B2 (de) * 1975-03-11 1979-12-13 Kemanord Ab, Nacka Verfahren zur Entfernung von Druckfarben von Papier und zur Reinigung des dabei entstehenden Abwassers
US4281199A (en) * 1978-06-03 1981-07-28 Basf Wyandotte Corporation Polyalkylene polyamine ether derivatives of polyoxyalkylene compounds
US4605707A (en) * 1985-02-25 1986-08-12 Allied Corporation Quaternary polyalkylene imine containing 2-hydroxypropyltrimethyl ammonium salt pendent side chain groups

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2610277B2 (de) * 1975-03-11 1979-12-13 Kemanord Ab, Nacka Verfahren zur Entfernung von Druckfarben von Papier und zur Reinigung des dabei entstehenden Abwassers
DE2733973A1 (de) * 1977-07-28 1979-02-15 Basf Ag Wasserloesliche, vernetzte stickstoffhaltige kondensationsprodukte
US4281199A (en) * 1978-06-03 1981-07-28 Basf Wyandotte Corporation Polyalkylene polyamine ether derivatives of polyoxyalkylene compounds
US4605707A (en) * 1985-02-25 1986-08-12 Allied Corporation Quaternary polyalkylene imine containing 2-hydroxypropyltrimethyl ammonium salt pendent side chain groups

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DE4007597A1 (de) 1991-09-12
AU7333891A (en) 1991-10-10

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