GB1086091A - A process for the production of urethane isocyanates - Google Patents

A process for the production of urethane isocyanates

Info

Publication number
GB1086091A
GB1086091A GB4153164A GB4153164A GB1086091A GB 1086091 A GB1086091 A GB 1086091A GB 4153164 A GB4153164 A GB 4153164A GB 4153164 A GB4153164 A GB 4153164A GB 1086091 A GB1086091 A GB 1086091A
Authority
GB
United Kingdom
Prior art keywords
groups
diisocyanate
diisocyanates
trimerized
catalysts
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
GB4153164A
Inventor
Dietrich Liebsch
Wilhelm Altner
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB1086091A publication Critical patent/GB1086091A/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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/77Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78Nitrogen
    • C08G18/79Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/02Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/022Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step

Landscapes

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

Abstract

Urethane isocyanates in admixture with trimerized monomeric diisocyanates are obtained by reacting one or more hydroxyl compounds which contain at least two hydroxyl groups capable of reacting with NCO groups, with one or more organic diisocyanates, in an excess of NCO groups over OH groups, and then trimerizing the remaining monomeric diisocyanate at a temperature below 150 DEG C. by adding a catalyst capable of polymerizing isocyanate groups and ending the latter reaction by adding a blocking agent for isocyanate polymerization when trimerization is complete. In examples toluylene diisocyanate and hexamethylene-1,6-diisocyanate are reacted with 1,1,1-trimethylolpropane, butane-1,3-diol and polypropylene glycols, and the products containing free diisocyanates are trimerized by adding tri-n-butylphosphine, pentamethyldiethylene triamine, sodium acetate and the lead salt of 2-ethylhexanoic acid as catalysts; the trimerization reactions are terminated by adding benzoyl chloride, p-toluene sulphonic acid methyl ester, ethyl acetate saturated with hydrogen chloride, and sulphuric acid dimethyl ester. Other starting materials, catalysts and blocking agents are mentioned.ALSO:Urethane isocyanates in admixture with trimerized monomeric diisocyanates are obtained by reacting one or more hydroxyl compounds which contain at least two hydroxyl groups capable of reacting with NCO groups, with one or more organic diisocyanates, in an excess of NCO groups over OH groups, and then trimerizing the remaining monomeric diisocyanate at a temperature below 150 DEG C. by adding a catalyst capable of polymerizing isocyanate groups and ending the latter reaction by adding a blocking agent for isocyanate polymerization when trimerization is complete. In examples toluylene diisocyanate and hexamethylene - 1,6 - diisocyanate are reacted with 1,1,1 - trimethylolpropane, butane - 1,3 - diol and polypropylene glycols, and the products containing free diisocyanates are trimerized by adding tri-n-butylphosphine, pentamethyl di-ethylene triamine, sodium acetate and the lead salt of 2-ethylhexanoic acid as catalysts; the trimerization reactions are terminated by adding benzoyl chloride, p-toluene sulphonic acid methyl ester, ethyl acetate saturated with hydrogen chloride, and sulphuric acid dimethyl ester. Other starting materials, catalysts and blocking agents are mentioned.
GB4153164A 1963-10-17 1964-10-12 A process for the production of urethane isocyanates Expired GB1086091A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0041013 1963-10-17

Publications (1)

Publication Number Publication Date
GB1086091A true GB1086091A (en) 1967-10-04

Family

ID=7098475

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4153164A Expired GB1086091A (en) 1963-10-17 1964-10-12 A process for the production of urethane isocyanates

Country Status (1)

Country Link
GB (1) GB1086091A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076945A (en) * 1971-10-05 1978-02-28 The General Tire & Rubber Company Method for making urethane-terminated polycarbodiimides and products thereof
US5331079A (en) * 1991-12-31 1994-07-19 E.R.T. Environmental Research Technology K.S.P.W. Inc. Liquid sorbent
US5817732A (en) * 1993-02-12 1998-10-06 Asahi Kasei Kogyo Kabushiki Kaisha Blocked polyisocyanate and coating composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4076945A (en) * 1971-10-05 1978-02-28 The General Tire & Rubber Company Method for making urethane-terminated polycarbodiimides and products thereof
US5331079A (en) * 1991-12-31 1994-07-19 E.R.T. Environmental Research Technology K.S.P.W. Inc. Liquid sorbent
US5817732A (en) * 1993-02-12 1998-10-06 Asahi Kasei Kogyo Kabushiki Kaisha Blocked polyisocyanate and coating composition

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