GB1020811A - Alkylene imine copolymerization products and process of making same - Google Patents

Alkylene imine copolymerization products and process of making same

Info

Publication number
GB1020811A
GB1020811A GB2523762A GB2523762A GB1020811A GB 1020811 A GB1020811 A GB 1020811A GB 2523762 A GB2523762 A GB 2523762A GB 2523762 A GB2523762 A GB 2523762A GB 1020811 A GB1020811 A GB 1020811A
Authority
GB
United Kingdom
Prior art keywords
imine
epichlorhydrin
ethylene imine
acid
per cent
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.)
Expired
Application number
GB2523762A
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.)
Chemirad Corp
Original Assignee
Chemirad Corp
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 Chemirad Corp filed Critical Chemirad Corp
Publication of GB1020811A publication Critical patent/GB1020811A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular 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
    • C08G73/02Polyamines
    • C08G73/0206Polyalkylene(poly)amines
    • C08G73/0213Preparatory process
    • C08G73/022Preparatory process from polyamines and epihalohydrins
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/02Polycondensates containing more than one epoxy group per molecule
    • C08G59/10Polycondensates containing more than one epoxy group per molecule of polyamines with epihalohydrins or precursors thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/40Macromolecules 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
    • C08G59/4007Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014Nitrogen containing compounds
    • C08G59/4042Imines; Imides
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds

Landscapes

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

Abstract

Alkylene imines are copolymerized with 0.05-10 mole per cent of alkyl halohydrins, or epihalohydrins, or polyepoxides, or compounds convertible into these under the reaction conditions. These compounds must have more than one halohydrin or epoxy group present or formed during the reaction, and at least one halogen atom which will react with the alkylene imine, or an acid may be provided for the latter purpose. Suitable compounds include, among others listed, epichlorhydrin, 1,2-halo-3-hydroxy propane, 2,3; 4,5 - diepoxy - 1,6 - dichlorohexane - 1,2 - epoxy - 3 - hydroxy - 4 - chloro - butane, and 2 - hydroxy - 1,3 - propane disulphuric acid ester, and the diepoxides butadiene diepoxide, vinyl cyclohexene diepoxide and N,N1-bis-(2,3-epoxy-propyl)-urea, in conjunction with an acid. The initial solution of the reactants should contain not more than 45% by weight of the imine. Any solvent for the monomers which is insert towards them is suitable, though water is preferred. The products are cationic, many-branched, polyamines giving stable water solutions not degenerating on storing. Spontaneous polymerization does not occur below about 40 DEG C., so that the imine and comonomer may be mixed in the reaction vessel, or immediately before entering it, then heated to polymerization temperature in a "batch reaction," or may be run, as a "continuous batch," into a mixture already at polymerization temperature, which the heat of polymerization helps to maintain. Examples describe the reactions of ethylene imine with 0.7 to 1.4 mole per cent of epichlorhydrin, and compares the products with acid-catalyzed polyimines of the prior art. Also described are reactions of 2-methyl ethylene imine, N-methyl ethylene imine, 2-ethyl ethylene imine, and N-n-butylethylene imine with epichlorhydrin in water, methanol, or isobutanol, or mixtures of methanol, isobutanol or benzene with water, and the reactions of ethylene imine with vinyl cyclohexene diepoxide and limonene diepoxide in hydrochloric acid.ALSO:Paper may be treated with a resin obtained by copolymerizing an alkyline imine with .05-10 mol per cent of an alkyl halohydrin or epihalohydrin (see Division C3). Addition of the resin improves the freeness and drainage, and the flocculation and filler retention of paper pulp slurries, and the wet strength and drying properties of sheet paper, and improves the adhesion of plastic films and of inks thereto. In an Example paper hand sheets are prepared containing .1 or .5 weight per cent of various ethylene imine-epichlorhydrin cocondensates.
GB2523762A 1962-02-01 1962-07-02 Alkylene imine copolymerization products and process of making same Expired GB1020811A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17048962A 1962-02-01 1962-02-01

Publications (1)

Publication Number Publication Date
GB1020811A true GB1020811A (en) 1966-02-23

Family

ID=22620051

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2523762A Expired GB1020811A (en) 1962-02-01 1962-07-02 Alkylene imine copolymerization products and process of making same

Country Status (2)

Country Link
DE (1) DE1495246B2 (en)
GB (1) GB1020811A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3520774A (en) * 1967-09-28 1970-07-14 Dow Chemical Co Epichlorodydrin-polyethyleneimine wet strength additive for paper
DE3237663A1 (en) * 1982-10-07 1984-04-12 Gosudarstvennyj institut prikladnoj chimii, Leningrad Process for the preparation of branched polyethylenimine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3520774A (en) * 1967-09-28 1970-07-14 Dow Chemical Co Epichlorodydrin-polyethyleneimine wet strength additive for paper
DE3237663A1 (en) * 1982-10-07 1984-04-12 Gosudarstvennyj institut prikladnoj chimii, Leningrad Process for the preparation of branched polyethylenimine
US4467115A (en) * 1982-10-07 1984-08-21 Institut Neftekhimicheskogo Sinteza Imeni A.V. Toncheva Akademii Nauk Sssr Method for preparing branched polyethylenimine

Also Published As

Publication number Publication date
DE1495246B2 (en) 1974-02-07
DE1495246A1 (en) 1970-10-08

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