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WO1991013924A1 - Composes solubles ou dispersibles dans l'eau contenant des chaines de polyether et des groupes quaternaires d'ammonium - Google Patents

Composes solubles ou dispersibles dans l'eau contenant des chaines de polyether et des groupes quaternaires d'ammonium Download PDF

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Publication number
WO1991013924A1
WO1991013924A1 PCT/EP1991/000375 EP9100375W WO9113924A1 WO 1991013924 A1 WO1991013924 A1 WO 1991013924A1 EP 9100375 W EP9100375 W EP 9100375W WO 9113924 A1 WO9113924 A1 WO 9113924A1
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WO
WIPO (PCT)
Prior art keywords
units
water
integer
compounds
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1991/000375
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German (de)
English (en)
Inventor
Ralf Bohlander
Günter Uphues
Uwe Ploog
Maria Liphard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1991013924A1 publication Critical patent/WO1991013924A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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 which contain polyether chains and quaternary ammonium groups, a process for their preparation and the use of these compounds for removing printing inks from printed waste paper and / or paper cycle water.
  • Waste paper is now used in large quantities for the production of, for example, newspaper printing and hygiene paper.
  • the quality of these types of paper is determined by their brightness and color.
  • the printing inks have to be removed from the printed waste paper. This is usually done using deinking processes, which essentially take place in two steps:
  • the second process step can be carried out by washing or flotation (Ull ann'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 used, air is pressed or sucked through the paper stock 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)).
  • alkylamine polyethers to remove printing ink is described in German Offenlegungsschrift DE-0S 33 22 330 and in German Patent DE-PS 33 47 906. Furthermore, from JP 84/137587, referenced in Chem.
  • 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 underlying the invention was to provide connections for deinking waste paper with which it is possible, in particular water-dilutable printing inks. to be removed in satisfactory amounts from waste paper.
  • the invention accordingly relates to water-soluble or water-dispersible compounds containing polyether chains and quaternary ammonium groups, obtainable by reacting compounds of the general formula I.
  • R a z-valent alkoxy radical
  • A0 1 to 100 alkylene oxide units which are composed of 0 to 100 C2H4 ⁇ units, 0 to 50 C3HöO units and 0 to 30 C ⁇ gO 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,
  • Another object 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 compounds of the general formula I R-
  • R is a z-valent alkoxy radical
  • AO 1 to 100 alkylene oxide units which are composed of 0 to 100 _2H4 ⁇ units, 0 to 50 C3Hö0 units and 0 to 30 C4HgO 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
  • aqueous or aqueous-alcoholic solutions to a Viskosi ⁇ ty at 20 ° C from 200 to 15,000 mPas is reacted, after anor ⁇ ganic and / or organic acids in amounts such that the pH of the solutions is between 4 and 7 and then reacted with ethylene oxide and / or propylene oxide at temperatures between 70 and 120 ° C and pressures between 10 4 and 10 5 Pa.
  • 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.
  • Compounds containing polyether chains and quaternary ammonium groups can be obtained by known processes from compounds of the general formula I by these in aqueous or aqueous-alcoholic solutions containing alkali metal hydroxides with ammonia, C22 -22-alkylamines, aliphatic di- and / or polyamines and / or amino sugars (NH compounds) are reacted at temperatures between 40 and 140 ° C (DE 22 46 434).
  • Ethanol and / or isopropanol are preferably used as alcohols in aqueous-alcoholic solutions.
  • the alcohols can be present in any mixing ratio with water.
  • the weight ratio of water to alcohol is between 10: 90 and 90: 10.
  • the solutions contain 20 to 80 wt .-%, preferably 40 to 60 wt .-%, compounds of general formula I and NH- Verbindu ⁇ gen.
  • inorganic and / or organic acids for example hydrochloric acid, sulfuric acid, acetic acid and / or lactic acid, up to a pH of the solutions between 4 and 7, preferably between 5 and 6.
  • reaction solutions in a known manner at temperatures between 70 and 120 ° C, preferably between 80 and 95 ° C, and pressures between 10 4 and 10 ⁇ Pa, preferably between 10 ⁇ and 3 x 10 ⁇ Pa, with ethylene oxide and / or propylene oxide implemented (DE 35 26 600, DE 36 18 944).
  • the alkylene oxides are used, based on amine nitrogen atoms, in amounts of 0.1 to 2 equivalents, preferably 0.3 to 1.2 equivalents.
  • the compounds of general formula I to be used as starting materials 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, page 131 - 132, Carl-Hanser-Verlag, Kunststoff - Vienna 1986)).
  • the alkoxylated alcohols if desired in a mixture with the corresponding non-alkoxylated alcohols, are mixed 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 between 60 and 95 ° C. implemented.
  • 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 and / or cyclic, primary and / or secondary, monohydric alkyl alcohols with 1 to 22 C atoms, such as methanol, ethanol, butanol, isopropanol, cyclohexanol, 2-ethylhexanol and / or lauryl alcohol, dihydric alcohols of the general formula H0- (CH2) 2-12 ⁇ ° H, bisphenol A, glycerol, di-, tri- and / or tetraglycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol and / or mannitol. Alcohols with 2 to 4 OH groups are preferred.
  • Ammonia, C22-ATkylamines for example dodecylamine, 2-ethylhexylamine, coconut amine and / or are suitable as NH compounds Talga in, linear, branched-chain and / or cyclic optionally partially alkoxylated, aliphatic di- and / or polyamines with optionally id groups in the aliphatic radicals, for example ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, dipropylenetriamine, dihexaethylenetriamine, 1,2 - Dihydroxyethyldiaminoethane, piperazine, polyethylenei ine with average molecular weights between 200 and 10,000, bis- [3,3-aminopropyl] methylamine, N, N-dimethylaminopropylamine, N-stearylpropylenediamine and / or N-acylamidoamine, producible by aminolysis of natural Fats and / or
  • Alkoxylated, preferably ethoxylated, di- and / or polyamines must have at least one NH group.
  • C 1 -C 22 -alkylamines and / or aliphatic di- and / or polyamines are preferably used as NH compounds.
  • the compounds according to the invention which are accessible by reacting compounds of the general formula I with NH compounds and then alkylene oxides are aqueous solutions or gels which form aqueous solutions with water and which contain the compounds according to the invention in amounts of 10 to 80% by weight, preferably 20 to 60% % By weight.
  • printing inks and in particular water-dilutable printing inks, can be removed particularly well from both printed waste paper and from paper circulation water.
  • the invention further relates to the use of these water-soluble or water-dispersible polyether chains and quaternary ammonium groups Connections for removing printing inks from printed old papers and / or paper circulation waters.
  • the compounds of this invention are paper stock suspensions material preferably in amounts of from 0.02 to 2 wt .-%, particularly preferably from 0.1 to 0.5 wt .-%, based on air-drymaschine ⁇ added.
  • 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 that is to say the removal of printing inks from printed waste paper
  • the compounds according to the invention are used in combination with, for example, cio ⁇ tartic acids, such as 01inor ⁇ 4010, 01inor ⁇ 4020 and / or 01inor R DG40 (Manufacturer of all products Henkel KGaA), 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 38 39479, in quantities of 0.01 to 1 % By weight, based on air-dry paper stock, and / or with layer compounds of the general composition precipitated in situ
  • M (II) stands for divalent metal cations
  • M (III) for trivalent metal cations
  • 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 preferably water-thinning printing inks
  • solvent-containing printing inks for example newspaper rotary inks, letterpress inks, off-set printing inks, gravure printing inks, flexographic printing inks, laser printing inks and / or remove packaging gravure inks from printed waste paper, for example newspapers, magazines, computer papers, magazines, brochures, forms, telephone books and / or catalogs.
  • the waste paper deinked using compounds 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, which typically contains 0 to 1.5% by weight hydrogen peroxide (100%), 0 to 2.5% by weight. 99% by weight NaOH and 0 to 4.0% by weight soda water glass with a solids content of 35% by weight (37 to 40 ° Be) - all% by weight information relates to air-dry paper stock , crushed at 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.
  • fatty acids for example fatty acids, ethoxylated alkyl alcohols and / or alkylphenols, polymers, copolymers and / or layer compounds precipitated in situ
  • these can be used before or during the size reduction of the paper stock or together with the compounds according to the invention be added to the pulp suspensions.
  • the compounds according to the invention When using the compounds according to the invention, 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 purification of paper circulation waters. In these cases, the addition of 2 to 100 mg of compounds according to the invention per liter of circulating water removes the printing ink particles, for example by filtration or flotation.

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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)
  • Inorganic Chemistry (AREA)
  • Toxicology (AREA)
  • Paper (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 pour éliminer les encres d'impression de vieux papiers imprimés et/ou d'eaux en circulation dans l'industrie de fabrication du papier.
PCT/EP1991/000375 1990-03-09 1991-03-01 Composes solubles ou dispersibles dans l'eau contenant des chaines de polyether et des groupes quaternaires d'ammonium Ceased WO1991013924A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4007598.2 1990-03-09
DE19904007598 DE4007598A1 (de) 1990-03-09 1990-03-09 Wasserloesliche oder wasserdispergierbare verbindungen, enthaltend polyetherketten und quaternaere ammoniumgruppen

Publications (1)

Publication Number Publication Date
WO1991013924A1 true WO1991013924A1 (fr) 1991-09-19

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PCT/EP1991/000375 Ceased WO1991013924A1 (fr) 1990-03-09 1991-03-01 Composes solubles ou dispersibles dans l'eau contenant des chaines de polyether et des groupes quaternaires d'ammonium

Country Status (3)

Country Link
AU (1) AU7311091A (fr)
DE (1) DE4007598A1 (fr)
WO (1) WO1991013924A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6284410B1 (en) 1997-08-01 2001-09-04 Duracell Inc. Zinc electrode particle form
US7247407B2 (en) 1997-08-01 2007-07-24 The Gillette Company Electrode having modal distribution of zinc-based particles

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19631150B4 (de) * 1996-08-01 2007-04-19 Süd-Chemie AG Verfahren zur Ablösung von Druckfarben (Deinking) von cellulosehaltigen Druckträgern
US7169257B2 (en) 2003-11-12 2007-01-30 Kemira Chemicals, Inc. Method of deinking waste paper using a reduced alkali system

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4281199A (en) * 1978-06-03 1981-07-28 Basf Wyandotte Corporation Polyalkylene polyamine ether derivatives of polyoxyalkylene compounds
EP0326890A2 (fr) * 1988-02-04 1989-08-09 Th. Goldschmidt AG Polyoxyalcoylène éther ayant des groupes d'ammonium quaternaires

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4281199A (en) * 1978-06-03 1981-07-28 Basf Wyandotte Corporation Polyalkylene polyamine ether derivatives of polyoxyalkylene compounds
EP0326890A2 (fr) * 1988-02-04 1989-08-09 Th. Goldschmidt AG Polyoxyalcoylène éther ayant des groupes d'ammonium quaternaires

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6284410B1 (en) 1997-08-01 2001-09-04 Duracell Inc. Zinc electrode particle form
US7247407B2 (en) 1997-08-01 2007-07-24 The Gillette Company Electrode having modal distribution of zinc-based particles
US7579113B2 (en) 1997-08-01 2009-08-25 The Gillette Company Electrode having modal distribution of zinc-based particles

Also Published As

Publication number Publication date
DE4007598A1 (de) 1991-09-12
AU7311091A (en) 1991-10-10

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