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US4499255A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of epoxy resins

Assignee: Dow Chemical Co
•
Filing: 1983-08-16
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Granted: 1985-02-12
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Expires: 2003-08-16
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Abstract

Abstract Epoxy resins are prepared by reacting an excess of an epihalohydrin with a phenolic hydroxyl-containing compound in the presence of the incremental addition of a basic catalyst while removing water by codistilling with a solvent and epihalohydrin.

Inventors

  • 👤 Chun S. Wang
  • 👤 Ha Q. Pham
  • 👤 James L. Bertram

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 04:53
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/02; C08G59/10; C08G59/04; C08G59/06; C08G59/063

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 211 words
In a method for preparing glycidyl derivatives of compounds having at least one aromatic hydroxyl group or aromatic amine group per molecule by reacting at least one compound having at least one aromatic hydroxyl group or aromatic amine group per molecule with an excess of at least one epihalohydrin in the presence of an alkali metal hydroxide and subsequently recovering the glycidyl derivative product; the improvement which comprises (1) conducting the reaction in the presence of an organic solvent which codistills with water and said epihalohydrin at a boiling point below the boiling point of the lowest boiling compound among the components in the reaction mixture; (2) conducting the reaction under a reduced pressure sufficient to provide a distillate with a boiling point of from about 45° C. to about 80° C.; (3) employing said alkali metal hydroxide as an aqueous solution and adding said aqueous alkali metal hydroxide in a continuous or intermittent manner over a period of from about 0.5 to about 10 hours; (4) continuously removing water by means of codistillation at a rate such that the water content in the reaction mixture is less than about 6 percent by weight; (5) separating the water from the codistillate and returning the solvent and epihalohydrin to the reaction mixture.
Claim 2
Dependent Claim 211 words
In a method for preparing glycidyl derivatives of compounds having at least one aromatic hydroxyl group or aromatic amine group per molecule by reacting at least one compound having at least one aromatic hydroxyl group or aromatic amine group per molecule with an excess of at least one epihalohydrin in the presence of an alkali metal hydroxide and subsequently recovering the glycidyl derivative product; the improvement which comprises (1) conducting the reaction in the presence of an organic solvent which codistills with water and said epihalohydrin at a boiling point below the boiling point of the lowest boiling compound among the components in the reaction mixture; (2) conducting the reaction under a reduced pressure sufficient to provide a distillate with a boiling point of from about 45° C. to about 80° C.; (3) employing said alkali metal hydroxide as an aqueous solution and adding said aqueous alkali metal hydroxide in a continuous or intermittent manner over a period of from about 0.5 to about 10 hours; (4) continuously removing water by means of codistillation at a rate such that the water content in the reaction mixture is less than about 6 percent by weight; (5) separating the water from the codistillate and returning the solvent and epihalohydrin to the reaction mixture.
Claim 3
Dependent Claim 99 words
A process of claim 1 wherein (a) said epihalohydrin is epichlorohydrin, (b) said compound having at least one aromatic hydroxyl group or aromatic amine group is a compound having at least one aromatic hydroxyl group, (c) said alkali metal hydroxide is sodium hydroxide, (d) the temperature is from about 55° to about 70° C., (e) the aqueous alkali metal hydroxide is added over a period of from about 1 to about 5 hours and (f) water is removed at a rate such that the water content in the reaction mixture is from about 1.5% to about 4% by weight.
Claim 4
Dependent Claim 25 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is a bisphenol or a phenol-formaldehyde novolac resin.
Claim 5
Dependent Claim 22 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is a cresol-formaldehyde novolac resin.
Claim 6
Dependent Claim 27 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is a tri(hydroxyphenyl)methane or mixture thereof with its higher homologs.
Claim 7
Dependent Claim 27 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is 4,4'-dihydroxybiphenyl or hydrocarbon or halogen ring substituted derivative thereof.
Claim 8
Dependent Claim 27 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is 4,4'-methylenedianiline or hydrocarbon or halogen ring substituted derivative thereof.
Claim 9
Dependent Claim 22 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is a polycyclopentadiene polyphenol resin.
Claim 10
Dependent Claim 22 words
A process of claim 2 wherein said compound having at least one aromatic hydroxyl group per molecule is a polycyclopentadiene polyresorcinol resin.
Claim 11
Dependent Claim 22 words
A process of claims 1, 2, 3, 4, 5, 6, 7 8 or 9 wherein said organic solvent is a secondary alcohol.
Claim 12
Dependent Claim 16 words
A process of claim 10 wherein said organic solvent is cyclohexanol, 1-methoxy-2-hydroxy propane or mixture thereof.
Claim 13
Dependent Claim 12 words
A process of claim 11 wherein said organic solvent is 1-methoxy-2-hydroxy propane.

References Cited (Backward Citations)

US2801227A Cited
US2824855A Cited
US2848435A Cited
US3121727A Cited
US3417050A Cited
US3980679A Cited
US4390680A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-02-12 1988-08-13 1989-02-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-02-12 1992-08-13 1993-02-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-02-12 1996-08-13 1997-02-12 $7700.00 Window Closed / Lapsed

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