GB1332668A - Poly n,n-ethylene ureas their conversion to thermoset resinous compositions and their use in the treatment of substrates containing wool - Google Patents

Poly n,n-ethylene ureas their conversion to thermoset resinous compositions and their use in the treatment of substrates containing wool

Info

Publication number
GB1332668A
GB1332668A GB4845970A GB4845970A GB1332668A GB 1332668 A GB1332668 A GB 1332668A GB 4845970 A GB4845970 A GB 4845970A GB 4845970 A GB4845970 A GB 4845970A GB 1332668 A GB1332668 A GB 1332668A
Authority
GB
United Kingdom
Prior art keywords
vinyl
poly
groups
esters
ethylene
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
GB4845970A
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.)
Ashland LLC
Original Assignee
Ashland Oil Inc
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 Ashland Oil Inc filed Critical Ashland Oil Inc
Publication of GB1332668A publication Critical patent/GB1332668A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/285—Nitrogen containing compounds
    • C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
    • C08G18/287—Imine 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/701—Compounds forming isocyanates or isothiocyanates in situ
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
    • C09D125/02—Homopolymers or copolymers of hydrocarbons
    • C09D125/04—Homopolymers or copolymers of styrene
    • C09D125/08—Copolymers of styrene
    • C09D125/14—Copolymers of styrene with unsaturated esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J125/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/02—Homopolymers or copolymers of hydrocarbons
    • C09J125/04—Homopolymers or copolymers of styrene
    • C09J125/08—Copolymers of styrene
    • C09J125/14—Copolymers of styrene with unsaturated esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/28—Non-macromolecular organic substances

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

1332668 Poly-N,N-ethylene ureas ASHLAND OIL Inc 12 Oct 1970 [10 Oct 1969] 48459/70 Heading C3P [Also in Division D1] Addition copolymers having a plurality of randomly distributed N,N-ethylene ureido groups attached directly through a N atom of such group to carbon atoms in the polymer backbone are prepared by (1) copolymerizing a tertiary amine acrylimide, which is optionally α-substituted, with a vinyl or vinylidene comonomer having no active hydrogen atoms, (2) thermally converting the pendent aminimide groups of the copolymer to isocyanate groups, and (3) reacting the pendent isocyanate groups with an ethylenimine of the formula in which R<SP>2</SP> to R<SP>5</SP> are the same or different and represent H, alkyl or aryl. The acrylimide monomer used in step (1) is preferably of the formula in which R is H, halogen or methyl, and R<SP>1</SP> is methyl or C 1 -C 6 hydroxyalkyl. Suitable comonomers include vinyl and vinylidene halides, (meth)acrylonitrile, unsymmetrical dialkyl-substituted ethylenes, α-olefins, vinyl ethers, vinyl esters, e.g. vinyl acetate, aromatic vinyl compounds, e.g. styrene, vinyl heterocyclic compounds, acrylamide and its derivatives, alkyl acrylates, haloacrylates and methacrylates, vinyl ketones, esters of unsaturated polycarboxylic acids, esters of unsaturated fatty acids and dimers and trimers thereof, vinyl silanes and fluorine-containing vinyl or acrylic esters. Copolymerization of the monomers may be effected in bulk, in aqueous medium or, preferably, in solution. The poly-N,N-ethylene ureas can be converted to thermoset products by heating in the presence of a catalyst (e.g. a Lewis acid, BF 3 or PF 5 ) preferably the polymers are reacted with cross-linking agents having at least two active hydrogen atoms, e.g. as present in -OH, -NH 2 , -COON or -SH groups. The cross-linking agent is preferably a polymeric compound having active hydrogencontaining groups, e.g. styrene/allyl alcohol copolymer, polyamide-amine or acrylic ester/ acrylic acid copolymer. The poly-N,N-ethylene ureas are also useful in treating wool to impart shrinkproof properties thereto.
GB4845970A 1969-10-10 1970-10-12 Poly n,n-ethylene ureas their conversion to thermoset resinous compositions and their use in the treatment of substrates containing wool Expired GB1332668A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US86549469A 1969-10-10 1969-10-10
US86549369A 1969-10-10 1969-10-10

Publications (1)

Publication Number Publication Date
GB1332668A true GB1332668A (en) 1973-10-03

Family

ID=27127904

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4845970A Expired GB1332668A (en) 1969-10-10 1970-10-12 Poly n,n-ethylene ureas their conversion to thermoset resinous compositions and their use in the treatment of substrates containing wool

Country Status (7)

Country Link
JP (2) JPS4832780B1 (en)
BE (1) BE757183A (en)
CA (1) CA945293A (en)
DE (1) DE2049703A1 (en)
FR (1) FR2065304A5 (en)
GB (1) GB1332668A (en)
NL (1) NL7014870A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021152453A1 (en) * 2020-01-27 2021-08-05 Italkem Srl Macromolecular compounds and use thereof in compositions

Also Published As

Publication number Publication date
DE2049703A1 (en) 1971-04-22
JPS4832780B1 (en) 1973-10-09
CA945293A (en) 1974-04-09
NL7014870A (en) 1971-04-14
BE757183A (en) 1971-03-16
JPS4922880B1 (en) 1974-06-12
FR2065304A5 (en) 1971-07-23

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Legal Events

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PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees