GB959286A - Improvements in or relating to bis-phenols - Google Patents

Improvements in or relating to bis-phenols

Info

Publication number
GB959286A
GB959286A GB30879/60A GB3087960A GB959286A GB 959286 A GB959286 A GB 959286A GB 30879/60 A GB30879/60 A GB 30879/60A GB 3087960 A GB3087960 A GB 3087960A GB 959286 A GB959286 A GB 959286A
Authority
GB
United Kingdom
Prior art keywords
bis
ketone
phenols
hydroxyphenyl
carbon atoms
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
GB30879/60A
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.)
Armour and Co
Original Assignee
Armour and 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 Armour and Co filed Critical Armour and Co
Publication of GB959286A publication Critical patent/GB959286A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol

Abstract

The invention comprises bis-phenols of formula: <FORM:0959286/C2/1> wherein R and R1 are alkyl groups containing differing numbers of carbon atoms, R and R1 together containing from 11 to 23 carbon atoms. They are used in the preparation of epoxy resins (see Division C3). The bis-phenols are prepared by condensing 2 moles of phenol with 1 mole of an unsymmetrical ketone such as 2-tridecanone, 2- or 3-pentadecanone, 2-heptadecanone, 2-tricosanone, 3-tetradecanone, 3-nonadecanone and 4-eicosanone. In an example a mixture of phenol, methyl undecyl ketone and beta-mercaptopropionic acid is heated to dissolve the ketone, cooled to 30 DEG C. and hydrogen chloride is bubbled into the mixture which solidifies at the end of the reaction. The product (2, 2-bis(4-hydroxyphenyl)-tridecane) is washed with water and petroleum ether and dried by azeotropic distillation. 2, 2-Bis(4-hydroxyphenyl)-nonadecane and 3, 3-bis(4-hydroxyphenyl)-tetradecane are similarly prepared.ALSO:Epoxy resins having improved adhesive strength at cryogenic temperatures are prepared from bis-phenols of formula: <FORM:0959286/C3/1> wherein R and R1 are alkyl groups having differing numbers of carbon atoms and R and R1 together contain 11-23 carbon atoms (see Division C2). In an Example epichlorhydrin and aqueous caustic soda solution were added to molten 2,2-bis (4-hydroxyphenyl)-nonadecane, the mixture refluxed, cooled, neutralised with hydrochloric acid and washed with water. Volatiles were removed by vacuum distillation to give a viscous amber liquid as product. In a further example triethylenetetramine was added to the epoxy resin and the mixture of resin and curing agent applied to steel strips which were overlapped by one-half inch and cured by heating. The strips were cooled in liquid nitrogen to -190 DEG C. and the shear strength of the cured resin tested and compared with the resins prepared from the bis-phenols derived by condensing 2 moles of phenol with 1 mole of acetone, methyl amyl ketone, methyl heptyl ketone, methyl nonyl ketone or dinonyl ketone.
GB30879/60A 1959-09-08 1960-09-07 Improvements in or relating to bis-phenols Expired GB959286A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US83839559A 1959-09-08 1959-09-08

Publications (1)

Publication Number Publication Date
GB959286A true GB959286A (en) 1964-05-27

Family

ID=25277005

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30879/60A Expired GB959286A (en) 1959-09-08 1960-09-07 Improvements in or relating to bis-phenols

Country Status (1)

Country Link
GB (1) GB959286A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0043612A1 (en) * 1980-07-08 1982-01-13 Shell Internationale Researchmaatschappij B.V. Polyglycidyl ethers of diphenylol alkanes, preparation and use in curable compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0043612A1 (en) * 1980-07-08 1982-01-13 Shell Internationale Researchmaatschappij B.V. Polyglycidyl ethers of diphenylol alkanes, preparation and use in curable compositions

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