Thermosetting polyquinolines

Claim 2

A polymer comprising quinoline repeat units and end groups comprising an acetylene functionality.

Claim 3

The polymer according to claim 1 wherein the end group is selected from the group consisting of: --C.tbd.CR, --Ar--C.tbd.CR, --CH 2 C.tbd.CR, --Ar--OCH 2 C.tbd.CR, and --OCH 2 C.tbd.CR, wherein R is H, alkyl, aryl or heteroaryl, and Ar is arylene or heteroarylene, where Ar may be optionally substituted with alkyl, aryl, alkoxy, aryloxy, chloro, fluoro, fluoroalkyl, fluoroaryl, and nitro, and R may be optionally substituted with alkoxy, aryloxy, chloro, fluoro, fluoroalkyl, fluoroaryl, and nitro.

Claim 4

The polymer according to claim 1 comprising end groups selected from the group consisting of --OCH 2 C.tbd.CH, --OCH 2 C.tbd.CCH 3 , --C.tbd.CH, --C.tbd.CC 6 H 5 , --C.tbd.C--C 6 H 4 O 6 CH 5 , --C.tbd.CCH 3 .

Claim 5

The polymer according to claim 1 comprising end groups selected from the group consisting of --C 6 H 4 --C.tbd.CH; ##STR33## --C 6 H 4 --OCH 2 C.tbd.CH, --C 6 H 4 --OCH 2 C.tbd.CCH 3 ; and --C 6 H 4 --OCH 2 C.tbd.CC 6 H 5 .

Claim 6

The polymer according to claim 2 wherein Ar is selected from the group consisting of 1,4-phenylene, 1,3-phenylene, 2-methyl-1,4-phenylene, 1,4-naphthylene, 4,4'biphenylene, 2,4-pyridinediyl, 2,4-quinolinediyl, 2,6-quinolinediyl, 4-phenyl,-2,6-quinolinediyl, and 3,6-quinolinediyl.

Claim 7

The polymer according to claim 1 wherein the quinoline repeat units have the structure: ##STR34## wherein Y is a divalent moiety selected from the group consisting of --O-- and --O--W--O, wherein W is a divalent group selected from the group consisting of: --Ar'--(where Ar' means arylene), --Het--(where Het means heteroarylene), --Ar'--O--Ar'--, --Ar'--C(O)--Ar'--, --Ar'--S--Ar'--, --Ar'--S(O)--Ar'--, --Ar'--S(O) 2 --Ar'--, and --Ar'--Q--Ar'--,; and wherein Q is a divalent group containing a quaternary carbon as shown below: Q= ##STR35## U, U'=--CH 3 , --CF 3 , Ar, or bridging where if U and U' are bridging, they may be alkyl, aryl, alkaryl, ether, ester, amide, alkyl ketone, aryl ketone, and may be partially or fully substituted with fluorine.

Claim 8

The polymer according to claim 6 wherein the quinoline repeat units have the structure: ##STR36##

Claim 9

The polymer according to claim 6 wherein the quinoline repeat units have the structure: ##STR37##

Claim 10

The polymer according to claim 1 wherein the quinoline repeat units have the structure: ##STR38##

Claim 11

A polymer having the formula: E"--(PQ).sub.n --E" where PQ is a polyquinoline polymer repeat unit, n is 1 to 100,000, E" is an end group selected from --C.tbd.CR, --Ar--C.tbd.CR, --CH 2 C.tbd.CR, --Ar--OCH 2 C.tbd.CR, and --OCH 2 C.tbd.CR, R is H, alkyl, aryl or heteroaryl, Ar is arylene or heteroarylene, where Ar may be optionally substituted with alkyl, aryl, alkoxy, aryloxy, chloro, fluoro, fluoroalkyl, fluoroaryl, and nitro, and R may be optionally substituted with alkoxy, aryloxy, chloro, fluoro, fluoroalkyl, fluoroaryl, and nitro.

Claim 12

A polymer having the formula: E"--(PQ).sub.n --E" where PQ is a polyquinoline polymer repeat unit, n is 1 to 100,000, E" is an end group selected from --C.tbd.CR, --Ar--C.tbd.CR, --CH 2 C.tbd.CR, --Ar--OCH 2 C.tbd.CR, and --OCH 2 C.tbd.CR, R is H, alkyl, aryl or heteroaryl, Ar is arylene or heteroarylene, where Ar may be optionally substituted with alkyl, aryl, alkoxy, aryloxy, chloro, fluoro, fluoroalkyl, fluoroaryl, and nitro, and R may be optionally substituted with alkoxy, aryloxy, chloro, fluoro, fluoroalkyl, fluoroaryl, and nitro.

Claim 13

The polymer according to claim 10 comprising end groups selected from the group consisting of --OCH 2 C.tbd.CH, --OCH 2 C.tbd.CCH 3 , --C.tbd.CH, --C.tbd.CC 6 H 5 , --C.tbd.C--C 6 H 4 O 6 CH 5 , --C.tbd.CCH 3 .

Claim 14

The polymer according to claim 10 comprising end groups selected from the group consisting of --C 6 H 4 --C.tbd.CH; ##STR39## --C 6 H 4 --OCH 2 C.tbd.CH; --C 6 H 4 --OCH 2 C.tbd.CCH 3 ; and --C 6 H 4 --OCH 2 C.tbd.CC 6 H 5 .

Claim 15

The polymer according to claim 10 wherein Ar is selected from the group consisting of 1,4-phenylene, 1,3-phenylene, 2-methyl-1,4-phenylene, 1,4-naphthylene, 4,4'biphenylene, 2,4-pyridinediyl, 2,4-quinolinediyl, 2,6-quinolinediyl, 4-phenyl,-2,6-quinolinediyl, and 3,6-quinolinediyl.

Claim 16

The polymer according to claim 10 wherein the quinoline repeat units have the structure: ##STR40##

Claim 17

The polymer according to claim 10 wherein the quinoline repeat units have the structure: ##STR41##

Claim 18

Cross-linked polyquinoline polymer compositions formed by heating a polymer of claim 10 above its T ex .

Claim 19

A method for forming thermoset polyquinoline polymers compositions comprising heating a polymer of claim 10 above its T ex .

Claim 20

The method according to claim 17 wherein the polymer is heated until at least half of the end groups have reacted.

Claim 21

The method according to claim 17 wherein the polymer is heated for a curing time determined by heating small (0.1 to 1 gram) samples of the polymer for various times and determining the exotherm area by differential scanning calorimetry, the curing time being the time necessary to reduce the exotherm area to 10% of the value for a sample that has not been heated.

Claim 22

The method according to claim 17 wherein the polymer is heated for a curing time determined by heating small (0.1 to 1 gram) samples of the polymer for various times and determining the exotherm area by differential scanning calorimetry, the curing time being the time necessary to reduce the exotherm area to 25% of the value for a sample that has not been heated.

Claim 23

The method according to claim 17 wherein the polymer is heated until it is insoluble in N-methylpyrrolidinone.

Claim 24

The method according to claim 17 wherein the polymer is heated under the application of pressure.

Claim 25

The method according to claim 22 wherein the polymer is heated under pressure in an autoclave.

Claim 26

The method according to claim 22 wherein the polymer is heated under pressure in a mold.

Claim 27

A method of forming solvent resistant films comprising coating a substrate with polymer compositions of claim 1 followed by heating the coated substrate above the T ex of said polymer composition.

Claim 28

The method of claim 25 wherein said polymer composition is spin coated onto a substrate from a solution of said polymer composition.

Claim 29

The method of claim 26 wherein the solution contains from 1% to 60% by weight solids.

Claim 30

The method of claim 26 wherein the solution contains from 10% to 30% by weight solids.

Claim 31

The method of claim 25 wherein the substrate is selected from the group consisting of aluminum, aluminum nitride, copper, diamond, quartz, silica, silicon, gallium arsenide, silicon carbide, gold, solder, and titanium; and where said substrate may have been previously coated with one or more layers of said polymer composition.

Claim 32

The method of claim 25 wherein said polymer composition is coated by spray coating a solution of said polymer composition.

Claim 33

The method of claim 25 wherein the substrate is a silicon wafer comprising preformed integrated circuits.

Claim 36

The method of claim 32 wherein the hydroxy endcapped polymer formed in step (a) is isolated as a pure or semi-pure solid before performing step (b).

Claim 37

The method of claim 32 wherein the bis-(fluorquinoline) is 6,6'-bis 2-(4-fluorophenyl)-4-phenylquinoline!.