Bis-propargyl thermosets

• US 5,475,133 A
• Filed: 11/28/1994
• Issued: 12/12/1995
• Est. Priority Date: 11/28/1994
• Status: Expired due to Fees

• Current Assignee: Los Alamos National Security LLC (Government of the United States of America)
• Original Assignee: Regents of the University of California (University of California)
• Inventors: Langlois, David A., Douglas, Elliot P., Benicewicz, Brian C.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US08/346,108
• Time in Patent Office: 379 Days
• Field of Search: 526/285, 560/61
• US Class Current: 560/61
• CPC Class Codes: C07C 69/92 with etherified hydroxyl groups
• CPC Class Codes: C08F 38/00 Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds

Abstract

The present invention provides (1) curable bispropargyl-containing monomers represented by the formula: B¹ --A¹_m --R--A²_n --B² wherein R is a radical selected from the group consisting of 1,4-phenylene, 4,4'"'"'-biphenyl, 2,6-naphthalene, --C₆ H₄ --CR² ═CR² --C₆ H₄ -- wherein R² is H or CH₃, and the same where said groups contain one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, A¹ and A² are selected from the group consisting of --C₆ H₄ --C(O)--O-- and --C₆ H₄ --O--C(O)--, m and n are 0 or 1, m+n is 0, 1 or 2, and B¹ and B² are --OCH₂ --C.tbd.C--H, (2) thermoset compositions comprised of cured segments derived from monomers represented by the formula: B¹ --A¹_m --R--A²_n --B² as described above, and (3) curable blends of at least two of the monomers.

Claims

1. A curable bispropargyl-containing monomer represented by the formula:

B¹ --A¹_m --R--A²_n --B² wherein R is a radical selected from the group consisting of 1,4-phenylene, 4,4'"'"'-biphenyl, 2,6-naphthalene, --C₆ H₄ --CR² ═

CR² --C₆ H₄ -- wherein R² is H or CH₃, and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, A¹ and A² are selected from the group consisting of --C₆ H₄ --C(O)--O-- and --C₆ H₄ --O--C(O)--, m and n are 0 or 1, m+n is 0, 1 or 2 and B¹ and B² are --OCH₂ --C.tbd.C--H.

2. The curable bispropargyl-containing monomer of claim 1 wherein R is 1,4-phenylene and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, and m and n are 1.

3. The curable bispropargyl-containing monomer of claim 1 wherein R is 4,4'"'"'-biphenyl, and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, and m and n are 1.

4. The curable bispropargyl-containing monomer of claim 1 wherein R is 2,6-naphthalene and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, and m and n are 1.

5. The curable bispropargyl-containing monomer of claim 1 wherein R is --C₆ H₄ --CR² ═

CR² --C₆ H₄ -- wherein R² is H or CH₃, and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, and m and n are 0 or 1.

6. The curable bispropargyl-containing monomer of claim 1 wherein R is 1,4-phenylene and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, m is 0 and n is 1.

7. The curable bispropargyl-containing monomer of claim 1 wherein R is --C₆ H₄ --CR² ═

CR² --C₆ H₄ -- wherein R² is H or CH₃, and the same where said radical contains one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, m and n are 0.