GB775721A - Resins derived from dihaloalkanes and polyalkylene polyamines - Google Patents

Resins derived from dihaloalkanes and polyalkylene polyamines

Info

Publication number
GB775721A
GB775721A GB14197/55A GB1419755A GB775721A GB 775721 A GB775721 A GB 775721A GB 14197/55 A GB14197/55 A GB 14197/55A GB 1419755 A GB1419755 A GB 1419755A GB 775721 A GB775721 A GB 775721A
Authority
GB
United Kingdom
Prior art keywords
mol
resin
water
diamine
dihaloalkanes
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
GB14197/55A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB775721A publication Critical patent/GB775721A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C08G73/0206—Polyalkylene(poly)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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/46—Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds
    • 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
    • D21H17/07—Nitrogen-containing compounds
    • 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
    • D21H17/375—Poly(meth)acrylamide
    • 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
    • D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
    • D21H17/45—Nitrogen-containing groups
    • D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised
    • 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
    • D21H17/56—Polyamines; Polyimines; Polyester-imides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paper (AREA)

Abstract

A resin having a viscosity in aqueous solution of A to Z6 (Gardner-Holdt) at 33 per cent resin solids is made by reacting 0.5-1.2 mol. of a dihaloakane containing 2 or 3 chain carbon atoms between the halogen atoms and of formula X-CnH2n-X where X is chlorine, bromine or iodine and n is 2, 3, or 4, with 1 mol. of a polyalkylene polyamine of formula <FORM:0775721/IV(a)/1> where Y is hydrogen, an alkyl radical containing from 1-4 carbon atoms or CmH2mNH2, m is at least 2 (preferably 2-4) and p is 0-4; the sum of m and n being at least 5. Reaction is effected at 25 DEG C., reflux in presence of water or a water-soluble alcohol, if desired in presence of an acid-acceptor (e.g. triethanolamine, triethylamine or N-methylmorpholine) until there are no organically bound halogen atoms present. The product is suitable for improving the wet-strength of paper, (see Group VIII). Specified polyalkylene polyamines are 1,2-ethylene diamine, trimethylenediamine, 1,2-propylene diamine, 1,3-butylene diamine, 1,4-butylene diamine, diethylenetriamine, triethylenetetramine, tetraethylene pentamine, N-methyl - N,N - bis - (3 - aminopropyl) amine, N - butyl - N,N - bis - (3 - aminopropyl) amine, 3,31 - iminobis - propylamine, 3,31,311 - nitrilo-trispropylamine, 1,5 - pentanediamine and 1,6-hexanediamine. Specified dihaloalkanes are 1,2-dihaloethanes and 1,3-dihalopropanes. A salt of the resin (e.g. with hydrochloric, hydrobromic, hydriodic, sulphuric or formic acid) may be condensed with 0.9-1.5 mol. of alkali metal cyanate or thiocyanate per mol. of nitrogen and 1-3 mol. of formaldehyde per mol. of cyanate or thiocyanate. The resin thus formed is water-soluble and may be employed in aqueous solution for the sizing of glass fibres or for improving the wet-strength of paper, or it may be spray-dried and used for moulding.
GB14197/55A 1954-06-10 1955-05-17 Resins derived from dihaloalkanes and polyalkylene polyamines Expired GB775721A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US435918A US2801169A (en) 1954-06-10 1954-06-10 Method of sizing paper with the condensation product of a long chain alkylamine withmethylenebisacrylamide

Publications (1)

Publication Number Publication Date
GB775721A true GB775721A (en) 1957-05-29

Family

ID=23730361

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14197/55A Expired GB775721A (en) 1954-06-10 1955-05-17 Resins derived from dihaloalkanes and polyalkylene polyamines

Country Status (2)

Country Link
US (1) US2801169A (en)
GB (1) GB775721A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003499A1 (en) 1978-01-20 1979-08-22 Bayer Ag Process for the manufacture of water-soluble condensation products, their use in papermaking and process-aids containing these condensation products

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945775A (en) * 1955-04-18 1960-07-19 Dow Chemical Co Sizing of paper with acrylamide polymers
US3019156A (en) * 1957-04-29 1962-01-30 American Cyanamid Co Wet strength paper containing polyamide
US2890978A (en) * 1957-10-02 1959-06-16 American Cyanamid Co Paper of high dry strength and low wet strength
US2948652A (en) * 1958-06-09 1960-08-09 American Cyanamid Co Wet strength paper containing linear polyamide resin
US3077430A (en) * 1959-09-25 1963-02-12 American Cyanamid Co Paper containing acrylamide copolymer
US3386880A (en) * 1965-03-22 1968-06-04 Ontario Research Foundation Process of forming paper containing polyethyleneimine cross-linked with methylene-bis-acrylamide and paper thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2338602A (en) * 1939-12-04 1944-01-04 Reconstruction Finance Corp Fabrication of wet-strengthened papers
BE486256A (en) * 1947-12-26
US2576502A (en) * 1949-04-01 1951-11-27 Sun Chemical Corp Polymers of reaction products of alkyl amines and methylene-bismethacrylamide
US2580568A (en) * 1950-05-16 1952-01-01 Ecusta Paper Corp Cigarette paper
US2694629A (en) * 1951-04-18 1954-11-16 American Cyanamid Co Production of sized alkaline paper

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003499A1 (en) 1978-01-20 1979-08-22 Bayer Ag Process for the manufacture of water-soluble condensation products, their use in papermaking and process-aids containing these condensation products
US4254255A (en) 1978-01-20 1981-03-03 Bayer Aktiengesellschaft Aqueous reaction of polyamine with alkylene dihalide in presence of emulsifier

Also Published As

Publication number Publication date
US2801169A (en) 1957-07-30

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