Interfacial polycarbonate polymerization process and product

• US 5,965,688 A
• Filed: 12/12/1997
• Issued: 10/12/1999
• Est. Priority Date: 12/12/1997
• Status: Expired due to Fees

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Davies, Jackie D.
• Primary Examiner(s): BOYKIN, TERRESSA M
• Application Number:
  US08/989,259
• Time in Patent Office: 669 Days
• Field of Search: 528/196
• US Class Current: 528/196
• CPC Class Codes: C08G 64/1608 saturated
• CPC Class Codes: C08G 64/28 and phenols

Abstract

A process for preparing an aromatic carbonate polymer by an interfacial polymerization reaction by first forming an aliphatic chloroformate and then reacting the bischloroformate with a dihydroxy phenol such as bisphenol-A. The resulting polymer consists of alternating units of the reaction residue of the dihydroxy phenol and the aliphatic chloroformate.

Claims

1. A carbonate copolymer consisting essentially of the residue of the polymerization reaction of one or more aromatic dihydroxy compound and an aliphatic haloformate, said carbonate copolymer having the formula:

##STR5## wherein R₁, R₂, R₃, and R₄ are independently selected from the group consisting of alkyl, aryl, and alkylaryl hydrocarbons of 1 to 20 carbon atoms, R is selected from the group consisting of alkyl, aryl, and alkylaryl hydrocarbons of 1 to 20 carbon atoms, disubstituted oxygen, sulfone, and spirobiindane, n is an integer of 5-200, and wherein the ratio of aromatic species to aliphatic species is 1;

0.5 to 1;

1.5.

2. The carbonate polymer of claim 1 wherein R is selected from the group consisting of alkyl groups having from 1-8 carbon atoms, isopropylidene, 1-phenylethyl, spirobiindane and mixtures thereof;

and R₁, R₂, R₃, and R₄ are each independently hydrocarbons of 3-10 carbon atoms.

3. The carbonate polymer of claim 1 wherein R is elected from the group consisting of alkyl groups having from 1-8 carbon atoms, isopropylidene, 1-phenylethyl, spirobiindane and mixtures thereof.

4. The carbonate polymer of claim 1 wherein R₁, R₂, R₃, and R₄ are each independently hydrocarbons of 3-10 carbon atoms.

5. The carbonate polymer of claim 1 wherein the ratio of aromatic species to aliphatic species in the copolymer is about 1:

1.

6. The carbonate polymer of claim 5 wherein R is selected from the group consisting of alkyl groups having from 1-8 carbon atoms, isopropylidene, 1-phenylethyl, spirobiindane and mixtures thereof, R₁, R₂, R₃, and R₄ are each independently hydrocarbons of 3-10 carbon atoms, and wherein the ratio of aromatic species to aliphatic species in the copolymer is about 1:

1.

7. The carbonate polymer of claim 6 wherein R₁, R₂, R₃, and R₄ are each methyl groups.

9. The process of claim 1, wherein the ratio of aromatic species to aliphatic species in the copolymer is about 1:

1.

10. The process of claim 9 wherein the carbonate precursor is phosgene.

11. The process of claim 9 wherein the aromatic dihydroxy compound is selected from the group consisting of an aromatic dihydroxy phenol, an hydroxybenzene, a dihydroxy phenyl, a dihydroxynaphthalene, a bis(hydroxyphenyl)sulfone, a bis(dihydroxyphenyl)ether, and combinations thereof.

12. The process of claim 10 wherein the aliphatic diol is a tetraalkylcyclobutanediol.

13. The process of claim 10 wherein the aromatic dihydroxy compound is selected from the group consisting of a dihydric phenol linked by a hydrocarbon having from 1-8 carbons, bisphenol A, spirobiindane dihydroxyphenol, or acetophenone dihydroxyphenol.

14. The process of claim 9 wherein the aliphatic diol is selected from the group consisting of cycloaliphatic diols, tetraalkylcyclobutanediols wherein the alkyl groups have from 1-8 carbons, and 2,2,4,4,-tetramethyl-1,3-cyclobutanediol.

15. The process of claim 9 wherein the aromatic dihydroxy phenol is 2,2-bis(4dihydroxyphenyl)propane spirobiindane dihydroxyphenol, or acetophenone dihydroxyphenol, and the aliphatic haloformate is 2,2,4,4-tetramethyl-1,3-cyclobutanediol bischloroformate.

16. The process of claim 9 wherein the pH is in the range from 10-14.

8. A process for preparing a carbonate copolymer by an interfacial polymerization reaction comprising:

reacting an aliphatic diol with a halogen containing carbonate precursor to form an aliphatic haloformate;

reacting the aliphatic haloformate with an aromatic dihydroxy compound in an interfacial polymerization reaction in the presence of an amine at a pH of 8-14 to form a carbonate copolymer consisting essentially of the residue of the aliphatic haloformate and the aromatic dihydroxy compound wherein the ratio of aromatic species to aliphatic species in the copolymer is 1;

0.5 to 1;

1.5.