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GB1109246A - Method of making polyurethane and said product - Google Patents

Method of making polyurethane and said product

Info

Publication number
GB1109246A
GB1109246A GB2314466A GB2314466A GB1109246A GB 1109246 A GB1109246 A GB 1109246A GB 2314466 A GB2314466 A GB 2314466A GB 2314466 A GB2314466 A GB 2314466A GB 1109246 A GB1109246 A GB 1109246A
Authority
GB
United Kingdom
Prior art keywords
diamine
mixture
polyol
bis
polyisocyanate
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
GB2314466A
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.)
Goodyear Tire and Rubber Co
Original Assignee
Goodyear Tire and Rubber 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 Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co
Publication of GB1109246A publication Critical patent/GB1109246A/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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/771—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur oxygen
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group

Landscapes

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

Abstract

A spreadable mixture which gives a polyurethane having improved resistance to discoloration comprises: (1) a reactive hydrogen containing material having a M.W. 500-6000 selected from polyester polyols, polyether polyols, polyether-polyester polyol, polyester-amide, castor oil, polycarbonate polyol, polydiene polyol and hydrogenated polydiene polyol; (2) an organic polyisocyanate in which all the NCO groups are attached to non-benzenoid carbon atoms; (3) a non-aromatic primary diamine; and (4) sufficient solvent to render the mixture spreadable. The polyisocyanate and the diamine are so selected that when reacted in boiling methylene chloride at 0.2 to 0.5 molar concentration, turbidity occurs in less than 30 seconds. (1) and (2) may be allowed to react to form a prepolymer before adding the diamine (3). The solvent (4) may be acetone or methyl ethyl ketone which may be heated with the diamine before adding to (1) and (2). From 1.3 to 3.0 moles of polyisocyanate may be used for each mol. of reactive hydrogen containing material; from 0.7 to 1.0 moles of diamine may be used for each mole of free isocyanate. The mixture may also contain from 5 to 100 parts by wt. per 100 parts of reaction mixture of a pigment. The mixtures may be used in the preparation of film and other shaped objects, e.g. filaments. The products of the examples were tested in a weatherometer in accordance with ASTM-E42-57 and ASTMD-1499-59T. Examples of suitable isocyanates are: 4,41 - diisocyanatodicyclohexyl methane, m-xylylene diisocyanate, hexamethylene diisocyanate and methylene bis-4,41-cyclohexyl isocyanate. Suitable diamines include: 1,4-cyclohexane-bis-(methylamine), trans-cyclobutane-1,2 - bis - (methylamine) and 1,6 - hexylene diamine.
GB2314466A 1965-06-25 1966-05-24 Method of making polyurethane and said product Expired GB1109246A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US46711565A 1965-06-25 1965-06-25

Publications (1)

Publication Number Publication Date
GB1109246A true GB1109246A (en) 1968-04-10

Family

ID=23854425

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2314466A Expired GB1109246A (en) 1965-06-25 1966-05-24 Method of making polyurethane and said product

Country Status (5)

Country Link
BE (1) BE682582A (en)
DE (1) DE1694277A1 (en)
GB (1) GB1109246A (en)
NL (1) NL6608841A (en)
SE (1) SE319007B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1955725A1 (en) * 1968-11-05 1970-05-06 Asahi Chemical Ind Elastomeric block polyurethane
JPS605414A (en) * 1983-06-21 1985-01-12 Dainippon Ink & Chem Inc Magnetic recording medium

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2632956C2 (en) * 1976-07-22 1987-02-12 Bayer Ag, 5090 Leverkusen Tetraalkylated biscyclohexylamine derivatives
ATE51405T1 (en) * 1984-01-11 1990-04-15 American Cyanamid Co A COATING COMPOUND CONTAINING A KETIMINE.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1955725A1 (en) * 1968-11-05 1970-05-06 Asahi Chemical Ind Elastomeric block polyurethane
JPS605414A (en) * 1983-06-21 1985-01-12 Dainippon Ink & Chem Inc Magnetic recording medium
JPH0531208B2 (en) * 1983-06-21 1993-05-12 Dainippon Ink & Chemicals

Also Published As

Publication number Publication date
BE682582A (en) 1966-11-14
SE319007B (en) 1969-12-22
NL6608841A (en) 1966-12-27
DE1694277A1 (en) 1970-09-24

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