GB1502577A - Polyhydroxy phenols and method for preparing the same - Google Patents

Polyhydroxy phenols and method for preparing the same

Info

Publication number
GB1502577A
GB1502577A GB4050276A GB4050276A GB1502577A GB 1502577 A GB1502577 A GB 1502577A GB 4050276 A GB4050276 A GB 4050276A GB 4050276 A GB4050276 A GB 4050276A GB 1502577 A GB1502577 A GB 1502577A
Authority
GB
United Kingdom
Prior art keywords
derivative
acid
diphenol
stage
phenol
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
GB4050276A
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.)
Societa Italiana Resine SpA SIR
Original Assignee
Societa Italiana Resine SpA SIR
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 Societa Italiana Resine SpA SIR filed Critical Societa Italiana Resine SpA SIR
Publication of GB1502577A publication Critical patent/GB1502577A/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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/08—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols from phenol-aldehyde condensates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

1502577 Polyhydroxyphenols and method for preparing the same SOC ITALIANA RESINE SIR SpA 29 Sept 1976 [30 Oct 1975] 40502/76 Heading C2C The invention relates to the compounds of formula wherein R is a C 1-4 hydrocarbon, and R 1 is and R 2 is hydrogen or equal to R 1 . These compounds may be obtained by a process comprising the steps of: (a) reacting formaldehyde and a diphenol of formula where R is a hydrocarbon radical containing from 1 to 4 carbon atoms, in a formaldehyde/ diphenol molar ratio of at least 1 : 1, preferably 1 : 1 to 4 : 1, in an aqueous medium and at a temperature of at least 40‹ C., preferably 40‹ to 80‹ C., in the presence of an inorganic base, e.g. NaOH and KOH, thereby to form a methylol derivative of said diphenol; (b) adding an acid to the reaction products of (a) in an amount at least equivalent to that of said inorganic base, and an organic solvent (e.g. toluene, xylene and cumene) capable of dissolving said methylol derivative, immiscible or only slightly miscible with water and forming with the latter an azeotropic mixture, and separating the aqueous phase and the organic phase thus obtained, this stage of the process being carried out at 30- 40‹ C.; (c) contacting said organic phase with phenol in an amount of at least one molecule for each methylol group of said derivative present in said organic phase, in the presence of an acid catalyst, which may be an organic acid preferably having a dissociation constant of above 1 Î 10<SP>-5</SP>, and at a temperature of at least 100‹ C., preferably 100‹ to 160‹ C., and maintaining the resulting mixture at boiling point until substantially complete reaction of said derivative with phenol, while distilling the forming water as an azeotrope with said organic solvent; and (d) recovering the polyhydroxy phenol from the reaction products of (c). It is preferred that the water content of reaction medium in stage (a) is from 25 to 40% by wt. The amount of acid which is added in stage (b) should preferably be such that the pH of the reaction medium is maintained between 6 to 5.
GB4050276A 1975-10-30 1976-09-29 Polyhydroxy phenols and method for preparing the same Expired GB1502577A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT2880875A IT1043742B (en) 1975-10-30 1975-10-30 PROCEDURE FOR THE PREPARATION OF POLYOXYDRYLIC PHENOLS AND POLYOXYDRYLIC PHENOLS SO PRODUCED

Publications (1)

Publication Number Publication Date
GB1502577A true GB1502577A (en) 1978-03-01

Family

ID=11224219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4050276A Expired GB1502577A (en) 1975-10-30 1976-09-29 Polyhydroxy phenols and method for preparing the same

Country Status (7)

Country Link
JP (1) JPS5257152A (en)
CA (1) CA1078873A (en)
DE (1) DE2648062A1 (en)
FR (1) FR2329630A1 (en)
GB (1) GB1502577A (en)
IT (1) IT1043742B (en)
NL (1) NL7611847A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4015440C1 (en) * 1990-05-15 1991-11-07 Ruetgerswerke Ag, 6000 Frankfurt, De

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1308699A (en) * 1970-06-26 1973-02-21 Moss Research Ltd William H Thermosetting resins and electrically insulating fibrous materials containing the same
JPS4992184A (en) * 1972-10-17 1974-09-03

Also Published As

Publication number Publication date
NL7611847A (en) 1977-05-03
FR2329630B1 (en) 1980-11-07
DE2648062A1 (en) 1977-05-05
FR2329630A1 (en) 1977-05-27
CA1078873A (en) 1980-06-03
IT1043742B (en) 1980-02-29
JPS5257152A (en) 1977-05-11

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Legal Events

Date Code Title Description
PS Patent sealed
746 Register noted 'licences of right' (sect. 46/1977)
PCNP Patent ceased through non-payment of renewal fee