Patent US4255556A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4255556A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of poly(ester carbonate) by interfacial method

Assignee: Honeywell International Inc
•
Filing: 1979-04-12
•
Granted: 1981-03-10
•
Expires: 1999-04-12
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Poly(ester carbonate) polymers are prepared by reaction of bifunctional phenolates in an aqueous phase with phosgene and with the acyl halide of a bifunctional carboxylic acid halide such as terephthaloyl chloride in an organic solvent such as dichloromethane. At least a portion of the phosgene is reacted with the phenolate before or during reaction of the acid chloride with the phenolate to avoid the formation of polyester blocks which have limited solubility in the organic solvent. After reaction is complete, or at any stage wherein oligomers are formed, the aqueous phase can be cleanly removed and easily separated from the organic phase, and the organic phase readily washed free of by-products. The final polymer product is recovered from the washed organic phase and is colorless, substantially amorphous and melt processable, and has a high glass transition temperature.

Inventors

  • 👤 Leon Segal
  • 👤 Bruce T. DeBona

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 06:12
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/64

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 275 words
An interfacial process of producing a substantially amorphous, melt processible poly(ester carbonate) which comprises: (1) mixing with an aqueous bisphenolate solution having a pH of at least about 8, (a) phosgene and (b) an organic solution of an acid halide which solution is immiscible with the aqueous bisphenolate solution, at a temperature and for a sufficient time and under sufficient agitation to react said phosgene and said acid halide with said bisphenolate to form an amorphous polymer, said aqueous bisphenolate being an alkali metal or alkaline earth metal salt of at least one bisphenol of the formula ##STR4## where R is alkylene of 1-4 carbons, --O--, --S--, --SO 2 --, --CO-- or a single bond, and R' is independently at each occurrence, H, Cl, Br, F, alkyl, phenyl or halogenated alkyl; said acid halide being at least one compound of the formula ##STR5## with X being Cl or Br, the acid halides being meta or para or 2,6 or 2,7 and R" being independently at each occurrence, H, Cl, Br, F, alkyl, phenyl or halogenated alkyl; the overall molar ratio of phosgene to acid halide being between about 0.2:1 and about 20:1; the molar ratio of bisphenolate to acid halide plus phosgene being between about 1:1 and about 1.0:1.2; and at least about 20% of phosgene as a mole percentage of the acid halide being mixed with the aqueous bisphenolate no later than the mixing of the acid halide with the bisphenolate; (2) separating the aqueous phase and the organic phase; (3) washing the organic phase with aqueous liquid; and (4) recovering the substantially amorphous, melt processable poly(ester carbonate) polymer from the washed organic phase.
Claim 2
Dependent Claim 275 words
An interfacial process of producing a substantially amorphous, melt processible poly(ester carbonate) which comprises: (1) mixing with an aqueous bisphenolate solution having a pH of at least about 8, (a) phosgene and (b) an organic solution of an acid halide which solution is immiscible with the aqueous bisphenolate solution, at a temperature and for a sufficient time and under sufficient agitation to react said phosgene and said acid halide with said bisphenolate to form an amorphous polymer, said aqueous bisphenolate being an alkali metal or alkaline earth metal salt of at least one bisphenol of the formula ##STR4## where R is alkylene of 1-4 carbons, --O--, --S--, --SO 2 --, --CO-- or a single bond, and R' is independently at each occurrence, H, Cl, Br, F, alkyl, phenyl or halogenated alkyl; said acid halide being at least one compound of the formula ##STR5## with X being Cl or Br, the acid halides being meta or para or 2,6 or 2,7 and R" being independently at each occurrence, H, Cl, Br, F, alkyl, phenyl or halogenated alkyl; the overall molar ratio of phosgene to acid halide being between about 0.2:1 and about 20:1; the molar ratio of bisphenolate to acid halide plus phosgene being between about 1:1 and about 1.0:1.2; and at least about 20% of phosgene as a mole percentage of the acid halide being mixed with the aqueous bisphenolate no later than the mixing of the acid halide with the bisphenolate; (2) separating the aqueous phase and the organic phase; (3) washing the organic phase with aqueous liquid; and (4) recovering the substantially amorphous, melt processable poly(ester carbonate) polymer from the washed organic phase.
Claim 3
Dependent Claim 36 words
The interfacial process of claim 1 wherein the bisphenolate is an alkali metal salt of a bisphenol of the first above formula where R' is H in all occurrences and R is alkylene of 1-4 carbons.
Claim 4
Dependent Claim 16 words
The interfacial process of claim 1 wherein the bisphenolate is the sodium salt of 2,2-bis(4-hydroxyphenyl) propane.
Claim 5
Dependent Claim 24 words
The interfacial process of claim 1 wherein said acid halide is selected from the group consisting of terephthalolyl chloride, isophthaloyl chloride and mixtures thereof.
Claim 6
Dependent Claim 13 words
The interfacial process of claim 4 wherein said acid halide is terephthaloyl chloride.
Claim 7
Dependent Claim 27 words
The interfacial process of claim 1 wherein said acid halide is selected from the group consisting of 1,4- and 1,3-cyclohexanedicarboxylic acid bromides and chlorides and mixtures thereof.
Claim 8
Dependent Claim 27 words
The interfacial process of claim 1 wherein said acid halide is selected from the group consisting of 2,6- and 2,7-napthalenedicarboxylic acid chloride and bromide and mixtures thereof.
Claim 9
Dependent Claim 39 words
The interfacial process of claim 1 wherein at least about 50% of phosgene as a molar percentage of the acid halide is mixed with the aqueous bisphenolate no later than the mixing of the acid halide with the bisphenolate.
Claim 10
Dependent Claim 34 words
The interfacial process of claim 1, 3 or 5 wherein all of said phosgene is dissolved with said acid halide in an organic solvent prior to mixing the organic phase with said aqueous bisphenolate.
Claim 11
Dependent Claim 22 words
The interfacial process of claim 9 wherein the molar ratio of phosgene to acid halide is between about 0.7:1 and about 1.2:1.
Claim 12
Dependent Claim 22 words
The interfacial process of claim 1 wherein the molar ratio of phosgene to acid halide is between about 0.7:1 and about 1.2:1.
Claim 13
Dependent Claim 28 words
The method of claim 1 wherein the agitation is sufficient to cause the reaction mixture to become opaque in appearance without separate phases clearly discernible by visual observation.
Claim 14
Dependent Claim 25 words
The method of claim 1 wherein the agitation is sufficient to achieve clean phase separation by merely allowing the reaction mixture to stand after reaction.

References Cited (Backward Citations)

US3028365A Cited
US3028364A Cited
US3030331A Cited
US3169121A Cited
US3646102A Cited
US3989672A Cited
US4156069A Cited
US4137218A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-03-09 1984-09-08 1985-03-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-03-09 1988-09-08 1989-03-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-03-09 1992-09-08 1993-03-10 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag