GB1351881A - Reaction product of o-o flexibilized phenolic resin with a poly isocyanate - Google Patents

Reaction product of o-o flexibilized phenolic resin with a poly isocyanate

Info

Publication number
GB1351881A
GB1351881A GB376172A GB376172A GB1351881A GB 1351881 A GB1351881 A GB 1351881A GB 376172 A GB376172 A GB 376172A GB 376172 A GB376172 A GB 376172A GB 1351881 A GB1351881 A GB 1351881A
Authority
GB
United Kingdom
Prior art keywords
reaction product
reactant
groups
phenol
excess
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
GB376172A
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 GB1351881A publication Critical patent/GB1351881A/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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/542—Polycondensates of aldehydes with phenols
    • 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
    • C08G18/089—Reaction retarding agents
    • 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
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4027—Mixtures of compounds of group C08G18/54 with other macromolecular 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28—Chemically modified polycondensates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

1351881 Polyurethanes ASHLAND OIL Inc 26 Jan 1972 [26 Jan 1971] 3761/72 Heading C3R A resinous composition curable to a thermoset condition upon contact with or exposure to an amine compound comprises a polyisocyanate and the reaction product of (1) a resinous condensate of a phenol and an aldehyde and (2) a compound containing two or more functional groups in which the functional groups are epoxide, hydroxyl or carboxylic acid groups, the said reaction product of (1) and (2) having free phenolic hydroxyl groups. Reactant (1) is preferably a condensate of phenol or an alkylsubstituted phenol with formaldehyde. Reactant (2) containing hydroxy groups is preferably a polyalkylene glycol or a polyol adduct thereof, a polyol initiated polycaprolactone, a polyester derived from polyhydric alcohols and polybasic acids and alkyd resins derived therefrom by modification with monocarboxylic acids, aminoplasts based on melamine and formaldehyde, hydroxy acrylates and methacrylates, hydroxy urethanes formed by reacting polyols in excess with polyisocyanates or polyisocyanate prepolymers, and natural oils such as tung, fish and linseed oils. Reactant (2) containing epoxide groups is preferably an epoxidized fatty ester of a monohydric or polyhydric alcohol or an epoxidized fatty alcohol, fatty nitrile, fatty amide or fatty amine. Reactant (2) containing carboxylic groups is preferably an acid-terminated polyester. The polyisocyanate reactant is preferably hexamethylene, 4,4<SP>1</SP>-dicyclohexylmethane, diphenylmethane, 2,4 - toluene or 2,6 - toluene diisocyanate or a prepolymer formed by reacting an excess of such polyisocyanates with a polyol, polyalkylene polyol or a polycaprolactone. The pot life of the blend of polyisocyanate and reaction product of (1) and (2) is improved by the presence of HCl, H 3 PO 4 , trichloroacetic and benzene sulphonic acids and phthaloyl chloride. Suitable amine hardeners are trimethylamine, triethylamine, dimethyl ethanolamine, ethyldimethylamine and methyldiethylamine, and if desired these may be blended suitably with the reaction product of (1) and (2). In examples a phenol paraformaldehyde condensation product formed in the presence of lead neodecanoate and consisting substantially of a mixture of ortho, ortho<SP>1</SP>-dimethylol phenol and 2,2<SP>1</SP>-dihydroxy- 3,3<SP>1</SP>-dimethylolbenzylic ether is reacted with polyesters based on adipic acid and either excess trimethylol propane or excess butane diol, the latter being subsequently reacted with a polyisooyanate and the product used to provide a film on a glass panel which was hard and tackfree after exposure to triethylamine.
GB376172A 1971-01-26 1972-01-26 Reaction product of o-o flexibilized phenolic resin with a poly isocyanate Expired GB1351881A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10992771A 1971-01-26 1971-01-26

Publications (1)

Publication Number Publication Date
GB1351881A true GB1351881A (en) 1974-05-01

Family

ID=22330321

Family Applications (1)

Application Number Title Priority Date Filing Date
GB376172A Expired GB1351881A (en) 1971-01-26 1972-01-26 Reaction product of o-o flexibilized phenolic resin with a poly isocyanate

Country Status (4)

Country Link
FR (1) FR2123445B1 (en)
GB (1) GB1351881A (en)
IT (1) IT946758B (en)
NL (1) NL7201013A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343924A (en) 1981-09-14 1982-08-10 Ashland Oil, Inc. Stabilized phenolic resins for use in vapor permeation curing
US4343839A (en) 1980-12-15 1982-08-10 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4365039A (en) 1980-12-15 1982-12-21 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4366193A (en) 1981-04-10 1982-12-28 Ashland Oil, Inc. Catechol-based vapor permeation curable coating compositions
US4368222A (en) 1981-06-05 1983-01-11 Ashland Oil, Inc. Vapor permeation curable coatings for surface-porous substrates
US4374167A (en) 1980-12-15 1983-02-15 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4374181A (en) 1981-09-14 1983-02-15 Ashland Oil, Inc. Vapor permeation curable coatings for reaction injection molded parts
US4396647A (en) 1982-02-22 1983-08-02 Ashland Oil, Inc. Vapor permeation curable coating compositions containing 2,3',4-trihydroxydiphenyl
US4634644A (en) * 1983-12-20 1987-01-06 Ciba-Geigy Corporation Process for the production images using sequentially gaseous polymerizing agents and photocuring
US4680346A (en) * 1985-12-13 1987-07-14 Ppg Industries, Inc. Flexible primer composition and method of providing a substrate with a flexible multilayer coating
US4803245A (en) * 1987-03-17 1989-02-07 Ashland Oil, Inc. Flexibilized phenol/mercapto resins and their synthesis

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3237000A1 (en) * 1982-10-06 1984-04-12 Hüttenes-Albertus Chemische Werke GmbH, 4000 Düsseldorf UNDER POLYURETHANIZATION, COLD-HARDENING MOLD BINDERS, THEIR PRODUCTION AND THEIR USE
US4540724A (en) * 1984-01-30 1985-09-10 Ashland Oil Inc. Phenolic resin-polyisocyanate binder systems containing a phosphorus halide and use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1345262A (en) * 1961-12-08 1963-12-06 Hooker Chemical Corp Polyurethane compositions containing derivatives of phenol-aldehyde resins

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343839A (en) 1980-12-15 1982-08-10 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4365039A (en) 1980-12-15 1982-12-21 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4374167A (en) 1980-12-15 1983-02-15 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4366193A (en) 1981-04-10 1982-12-28 Ashland Oil, Inc. Catechol-based vapor permeation curable coating compositions
US4368222A (en) 1981-06-05 1983-01-11 Ashland Oil, Inc. Vapor permeation curable coatings for surface-porous substrates
US4343924A (en) 1981-09-14 1982-08-10 Ashland Oil, Inc. Stabilized phenolic resins for use in vapor permeation curing
US4374181A (en) 1981-09-14 1983-02-15 Ashland Oil, Inc. Vapor permeation curable coatings for reaction injection molded parts
US4396647A (en) 1982-02-22 1983-08-02 Ashland Oil, Inc. Vapor permeation curable coating compositions containing 2,3',4-trihydroxydiphenyl
US4634644A (en) * 1983-12-20 1987-01-06 Ciba-Geigy Corporation Process for the production images using sequentially gaseous polymerizing agents and photocuring
US4680346A (en) * 1985-12-13 1987-07-14 Ppg Industries, Inc. Flexible primer composition and method of providing a substrate with a flexible multilayer coating
US4803245A (en) * 1987-03-17 1989-02-07 Ashland Oil, Inc. Flexibilized phenol/mercapto resins and their synthesis

Also Published As

Publication number Publication date
IT946758B (en) 1973-05-21
DE2203595B2 (en) 1975-07-24
DE2203595A1 (en) 1972-08-03
FR2123445B1 (en) 1976-07-23
NL7201013A (en) 1972-07-28
FR2123445A1 (en) 1972-09-08

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years