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GB994890A - New organic polyisocyanates and their manufacture - Google Patents

New organic polyisocyanates and their manufacture

Info

Publication number
GB994890A
GB994890A GB4523161A GB4523161A GB994890A GB 994890 A GB994890 A GB 994890A GB 4523161 A GB4523161 A GB 4523161A GB 4523161 A GB4523161 A GB 4523161A GB 994890 A GB994890 A GB 994890A
Authority
GB
United Kingdom
Prior art keywords
diisocyanate
reaction
excess
urethane
group
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
GB4523161A
Inventor
Vincent Kerrigan
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB4523161A priority Critical patent/GB994890A/en
Publication of GB994890A publication Critical patent/GB994890A/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
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7843—Nitrogen containing -N-C=0 groups containing urethane groups
    • 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
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203

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

The invention comprises allophanate polyisocyanates which are obtainable by reacting an excess of organic diisocyanate with a urethane isocyanate of formula R1(OOCNHRNCO)n where R1 is a monovalent or polyvalent organic radical, the residue of a mono or polyhydroxylic compound after reaction of the hydroxyl group with an isocyanate group, n is an integer from 1 to 6 and represents the functionality of the hydroxyl compound and R is a divalent organic radical, the excess of organic diisocyanate being an excess over that required for the reaction of one molecule of diisocyanat for each urethane group. Examples of monoe hydric alcoholds from which R1 may bedrived include methanol, ethanol, isopropanol and phenol.ALSO:Allophanate polyisocyanates are produced by reacting an excess of organic diisocyanate with a urethane isocyanate of formula R1(OOCNHRNCO)n, wherein R1 is a monovalent or polyvalent organic radical, the residue of a mono- or poly-hydroxylic compound after reaction of the hydroxyl group with an isocyanate group, n is an integer from 1 to 6 and represents the functionality of the hydroxyl compound and R is a divalent substituted or unsubstituted organic radical, the excess of organic diisocyanate being an excess over that required for the reaction of one molecule of diisocyanate for each urethane group. The divalent radical R may be alkyl, cycloalkyl, aryl or aralkyl and may be substituted e.g. by halogen, nitro or other radicals non-reactive to the isocyanate group. The radical R1 may preferably be derived from alcohols containing 2 to 6 hydroxyl groups, e.g. ethylene glycol, diethylene glycol, trimethylol propane, glycerol, butylene glycols and oxypropylation products of diethylene glycol, trimethylolpropane and sorbitol. Any organic diisocyanate may be used, preferred diisocyanates are: hexamethylene-, tolylylene-, methylcohexyl-, and xylylene diisocyanates in an excess of from 10 to 300% over that required for the reaction of one molecule of diisocyanate with each urethane group. A catalyst may be added, e.g. metal carboxylate, metal chelate, or tertiary amine. Many catalysts are listed. Without a catalyst the reaction is carried out at 100 DEG to 160 DEG C. and with a catalyst at 0 DEG to 50 DEG C. A solvent, e.g. ethyl acetate or butyl acetate may be used. The reaction product may be used as polyisocyanate in the production of polyurethanes which may be homogeneous or cellular, rigid or flexible. In examples the reactants were: (1) hexamethylene diisocyanate and diethylene glycol; (3) tolylene diisocyanate and trimethylol propane; (4) hexamethylene diisocyanate and oxypropylated sorbitol catalysed by pyrrolizidine; in (7) the product of Example (6) was reacted with an adduct of propylene oxide and triethanolamine to produce a polyurethane foam.ALSO:An allophanate polyisocyanate produced by reacting hexamethylene diisocyanate with oxypropylated sorbitol under conditions such that allophanate groups are formed by reaction of isocyanate and urethane groups in Example 5 (see Division C3) is subsequently dissolved (in Example 8) in ethylene glycol monoethyl ether acetate and dibutyltin dilaurate added and the solution painted on to clean tinned iron plates.
GB4523161A 1961-12-18 1961-12-18 New organic polyisocyanates and their manufacture Expired GB994890A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4523161A GB994890A (en) 1961-12-18 1961-12-18 New organic polyisocyanates and their manufacture

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4523161A GB994890A (en) 1961-12-18 1961-12-18 New organic polyisocyanates and their manufacture

Publications (1)

Publication Number Publication Date
GB994890A true GB994890A (en) 1965-06-10

Family

ID=10436401

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4523161A Expired GB994890A (en) 1961-12-18 1961-12-18 New organic polyisocyanates and their manufacture

Country Status (1)

Country Link
GB (1) GB994890A (en)

Cited By (136)

* Cited by examiner, † Cited by third party
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