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Diarylacetylenes, enamines and acetylenic polymers and their production

Assignee: Individual
•
Filing: 1993-05-04
•
Granted: 1994-12-20
•
Expires: 2013-05-04
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Abstract

Abstract Diarylacetylenes and diarylenamines are synthesized from a Schiff's base and an N-arylmethylheterocycle; these compounds are useful as intermediates for a variety of polymers; in particular an efficient process is provided for producing diaryl acetylenes useful in the efficient production of acetylene group-containing polymers which can be cross-linked to produce high strength polymers free of structural defects such as conventionally arise as a result of liberation of volatiles during the cross-linking.

Inventors

  • 👤 Allan S. Hay
  • 👤 Martino Paventi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-10 01:06
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07C; C07C1/00; C07C1/32; C07C1/321; C07C1/323; C07C2/00; C07C2/86; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C43/225; C07C43/257; C07C43/285; C07C43/30; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D249/00; C07D249/16; C07D249/18; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C08; C08G; C08G63/00; C08G63/02; C08G63/12; C08G63/52; C08G63/54; C08G63/547; C08G64/00; C08G64/04; C08G64/045; C08G65/00; C08G65/34; C08G65/38; C08G65/40; C08G65/4006; C08G75/00; C08G75/20; C08G75/23; C08G2650/00; C08G2650/28; C08G2650/38; C08G2650/44

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 299 words
A process for producing an acetylenic group-containing polymer or copolymer of formula (VII): ##STR27## wherein Z 1 is fluorine, hydroxyl or mercaptyl, Z 2 is hydrogen or fluorine Z 3 is --O--, --S--, --CH 2 --, --CO--, --CO--Ar 6 --CO-- or --Ar 7 --, in which Ar 6 and Ar 7 are selected from divalent aromatic linkages, Y 1 and Y 2 are each selected from --O-- or --S--, provided that when Z 3 is --O-- or --S--, Y 1 and Y 2 are both single bonds, Ar 4 and Ar 5 are each independently selected from arylene or hetarylene, unsubstituted or substituted one or more times by radicals selected from F; Cl,; Br; alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 18 carbon atoms; aralkenyl of 8 to 18 carbon atoms; alkoxy of 1 to 6 carbon atoms; thioalkoxy of 1 to 6 carbon atoms; aryloxy of 6 to 12 carbon atoms or thioaryloxy of 6 to 12 carbon atoms; X is --Ar 4 --C.tbd.C--Ar 5 or a copolymer unit, n is an integer of 2 to 200, x is an integer of 0 to 199 and n is >x, comprising: polymerizing a diarylacetylene of formula (VI): X.sub.1 --Ar.sub.4 --C.tbd.C--Ar.sub.5 --X.sub.2 (VI) in which X 1 and X 2 are independently selected from F or OH and Ar 4 and Ar 5 are as defined above, or copolymerizing said diarylacetylene of formula (VI) with a comonomer selected from dihydroxy aromatics or dihaloaromatics in which the halogen atoms are activated for displacement, or in the presence of a reactant which provides a divalent linkage for the acetylenic monomer units, selected from --CH 2 --, --O--, --S--, --CO-- or said copolymer unit X.
Claim 2
Dependent Claim 299 words
A process for producing an acetylenic group-containing polymer or copolymer of formula (VII): ##STR27## wherein Z 1 is fluorine, hydroxyl or mercaptyl, Z 2 is hydrogen or fluorine Z 3 is --O--, --S--, --CH 2 --, --CO--, --CO--Ar 6 --CO-- or --Ar 7 --, in which Ar 6 and Ar 7 are selected from divalent aromatic linkages, Y 1 and Y 2 are each selected from --O-- or --S--, provided that when Z 3 is --O-- or --S--, Y 1 and Y 2 are both single bonds, Ar 4 and Ar 5 are each independently selected from arylene or hetarylene, unsubstituted or substituted one or more times by radicals selected from F; Cl,; Br; alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 18 carbon atoms; aralkenyl of 8 to 18 carbon atoms; alkoxy of 1 to 6 carbon atoms; thioalkoxy of 1 to 6 carbon atoms; aryloxy of 6 to 12 carbon atoms or thioaryloxy of 6 to 12 carbon atoms; X is --Ar 4 --C.tbd.C--Ar 5 or a copolymer unit, n is an integer of 2 to 200, x is an integer of 0 to 199 and n is >x, comprising: polymerizing a diarylacetylene of formula (VI): X.sub.1 --Ar.sub.4 --C.tbd.C--Ar.sub.5 --X.sub.2 (VI) in which X 1 and X 2 are independently selected from F or OH and Ar 4 and Ar 5 are as defined above, or copolymerizing said diarylacetylene of formula (VI) with a comonomer selected from dihydroxy aromatics or dihaloaromatics in which the halogen atoms are activated for displacement, or in the presence of a reactant which provides a divalent linkage for the acetylenic monomer units, selected from --CH 2 --, --O--, --S--, --CO-- or said copolymer unit X.
Claim 3
Dependent Claim 85 words
A process according to claim 1 in which x is an integer 0; Ar 4 and Ar 5 are each independently selected from said unsubstituted or substituted arylene; Y 1 and Y 2 are both --O--; and Z 3 is said radical --Ar 7 -- in which --Ar 7 -- is a radical of formula: ##STR28## in which R is hydrogen, lower alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms, which comprises polymerizing said diarylacetylene of formula (VI).
Claim 4
Dependent Claim 115 words
A process according to claim 1 in which x is an integer greater than 0; Ar 4 and Ar 5 are each independently selected from said unsubstituted or substituted arylene; Y 1 and Y 2 are both --O--; Z is said radical --Ar 7 -- in which --Ar 7 -- is a radical of formula: ##STR29## in which R is hydrogen, lower alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms, and X is a radical of formula: ##STR30## which comprises copolymerizing said diarylacetylene of formula (VI) with a comonomer of formula: ##STR31## in which Y 1 and Y 2 are independently selected from hydroxy fluorine, chlorine or bromine.
Claim 5
Dependent Claim 227 words
An acetylenic group-containing polymer or copolymer of formula (VII): ##STR32## wherein Z 1 is fluorine, hydroxyl or mercaptyl, Z 2 is hydrogen or fluorine, Z 3 is --O--, --S--, --CH 2 --, --CO--, --CO--Ar 6 --CO-- or --Ar 7 --, in which Ar 6 and Ar 7 are selected from divalent aromatic linkages, Y 1 and Y 2 are each selected from --O-- or --S--, provided that when Z 3 is --O-- or --S--, Y 1 and Y 2 are both single bonds, Ar 4 and Ar 5 are each independently selected from arylene or hetarylene, unsubstituted or substituted one or more times by radicals selected from F; Cl,; Br; alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 18 carbon atoms; aralkenyl of 8 to 18 carbon atoms; alkoxy of 1 to 6 carbon atoms; thioalkoxy of 1 to 6 carbon atoms; aryloxy of 6 to 12 carbon atoms or thioaryloxy of 6 to 12 carbon atoms; X is Ar 4 --C.tbd.C--Ar 5 or a copolymer unit, n is an integer of 2 to 200, x is an integer of 0 to 199 and n is >x, provided that when the polymer or copolymer has acetylenic units --Ar 4 --C.tbd.C--Ar 5 at both terminal positions, n is at least 3.
Claim 6
Dependent Claim 227 words
An acetylenic group-containing polymer or copolymer of formula (VII): ##STR32## wherein Z 1 is fluorine, hydroxyl or mercaptyl, Z 2 is hydrogen or fluorine, Z 3 is --O--, --S--, --CH 2 --, --CO--, --CO--Ar 6 --CO-- or --Ar 7 --, in which Ar 6 and Ar 7 are selected from divalent aromatic linkages, Y 1 and Y 2 are each selected from --O-- or --S--, provided that when Z 3 is --O-- or --S--, Y 1 and Y 2 are both single bonds, Ar 4 and Ar 5 are each independently selected from arylene or hetarylene, unsubstituted or substituted one or more times by radicals selected from F; Cl,; Br; alkyl of 1 to 6 carbon atoms; alkenyl of 2 to 6 carbon atoms; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 18 carbon atoms; aralkenyl of 8 to 18 carbon atoms; alkoxy of 1 to 6 carbon atoms; thioalkoxy of 1 to 6 carbon atoms; aryloxy of 6 to 12 carbon atoms or thioaryloxy of 6 to 12 carbon atoms; X is Ar 4 --C.tbd.C--Ar 5 or a copolymer unit, n is an integer of 2 to 200, x is an integer of 0 to 199 and n is >x, provided that when the polymer or copolymer has acetylenic units --Ar 4 --C.tbd.C--Ar 5 at both terminal positions, n is at least 3.
Claim 7
Dependent Claim 79 words
An acetylenic group-containing polymer according to claim 4 in which x is an integer 0; Ar 4 and Ar 5 are each independently selected from said unsubstituted or substituted arylene; Y 1 and Y 2 are both --O--; and Z 3 is said radical --Ar 7 -- in which --Ar 7 -- is a radical of formula: ##STR33## in which R is hydrogen, lower alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms.
Claim 8
Dependent Claim 87 words
An acetylenic group-containing copolymer according to claim 4 in which x is an integer greater than 0; Ar 4 and Ar 5 are each independently selected from said unsubstituted or substituted arylene; Y 1 and Y 2 are both --O--; Z is said radical --Ar 7 -- in which --Ar 7 -- is a radical of formula: ##STR34## in which R is hydrogen, lower alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms, and X is a radical of formula: ##STR35##

References Cited (Backward Citations)

US4251417A Cited
US4268654A Cited
US4436886A Cited
US4417039A Cited
US4587312A Cited
US4567240A Cited
US4513131A Cited
US5248748A Cited
US4730032A Cited
US5262515A Cited
US5189127A Cited
US5189129A Cited
US5239031A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-12-19 1998-06-20 1998-12-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-12-19 2002-06-20 2002-12-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-12-19 2006-06-20 2006-12-20 $7700.00 Window Closed / Lapsed

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