Polymer resulting from the cure of a preformed chromene-containing mixture

• US 5,155,196 A
• Filed: 06/01/1990
• Issued: 10/13/1992
• Est. Priority Date: 06/01/1987
• Status: Expired due to Fees

• Current Assignee: The Dow Chemical Company (Dow, Inc.)
• Original Assignee: The Dow Chemical Company (Dow, Inc.)
• Inventors: Inbasekaran, Muthiah, Godschalx, James P., Scheck, Daniel M., Dirlikov, Stoil, Kolb, Gerald C.
• Primary Examiner(s): Henderson, Christopher
• Application Number:
  US07/532,297
• Time in Patent Office: 865 Days
• Field of Search: 526/285, 526/267, 526/268, 526/286, 526/289, 526/247
• US Class Current: 526/268
• CPC Class Codes: C07C 317/00 Sulfones; Sulfoxides
• CPC Class Codes: C07C 41/16 by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
• CPC Class Codes: C07C 43/215 having unsaturation outside the six-membered aromatic rings
• CPC Class Codes: C07C 43/225 containing halogen
• CPC Class Codes: C07C 45/71 being hydroxy groups
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 311/58 other than with oxygen or sulphur atoms in position 2 or 4

Abstract

This invention relates to a solvent process for the conversion of aromatic propargyl ethers into chromenes. The process can be catalyzed with copper or zinc salts. The preferred salt is cuprous chloride. The most preferred solvent is a dichlorobenzene. The invention also relates to chromene products formed using the process and to the polymerization of that chromene product and its polymerized product, the latter product having substantially improved flexural modulus and flexural strength properties. The polymerized product is also moisture insensitive.

Claims

1. A polymer resulting from the cure of a preformed chromene-containing mixture of monomers of the formula:

##STR25## wherein X is absent, --S--, --O--, --C(CH₃)₂ --, --C(CF₃)₂ --, ##STR26## --SO₂ --, or --CO--, m is 2 and m'"'"' is 0, 1, or 2, wherein the average value of "m'"'"'" within said mixture is greater than about 0.2, and polymerization occurs through at least one chromene radical.

2. The polymer of claim 1, having a flexural modulus of about 630 ksi.

3. The polymer of claim 1, having a flexural strength of about 14 ksi.

4. The polymer of claim 1, wherein said polymer is substantially insoluble.

5. The polymer of claim 1, wherein said polymer is substantially infusible.

6. The polymer according to claim 1, wherein X is --C(CH₃)₂ -- and m is 2.

7. The polymer of claim 1, wherein said polymer is substantially void-free.