IP Library Granted Patent US 7,737,236
Granted Patent B2
US 7,737,236 · App. 11/077,199 · Granted Jun 15, 2010

Polymers based on fluoranthene and their use

Assignee: BASF Aktiengesellschaft
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Quick Facts
Patent No.
US 7,737,236
App. No.
11/077,199
Granted
Jun 15, 2010
Kind
B2
Abstract

Polymers comprising repeating units of the formula I where the variables are defined as follows: a is an integer from 0 to 3, R 1 , R 2 , R 3 are identical or different and are selected independently from among hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl containing one or more Si, N, P, O or S atoms, C 6 -C 30 -aryl, preferably C 6 -C 14 -aryl, C 4 -C 14 -heteroaryl, —N(C 6 -C 14 -aryl) 2 , and Y 1 , where Y 1 may be identical or different and are selected from among —CH═CH 2 , trans- or cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, O—CH═CH 2 and glycidyl, where Y 2 is selected from among —CH═CH 2 , trans- or cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 and glycidyl, and one or more groups Y 1 or Y 2 may be crosslinked to one another.

Claims (53)

1. A monomer of the formula III

wherein the variables are defined as follows:

a is an integer from 0 to 3,

R 1 , R 2 , R 3 are identical or different and are selected independently from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl containing one or more Si, N, P, O or S atoms, C 6 -C 30 -aryl, C 4 -C 14 -heteroaryl containing at least one S or N atom, —N(C 6 -C 14 -aryl) 2 , and Y 1 ,

wherein Y 1 may be identical or different and are selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 , glycidyl,

wherein Y 2 is selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 and glycidyl, and one or more groups Y 1 or Y 2 may be crosslinked to one another,

R 6 are identical or different and are each, depending on one another, hydrogen or C 1 -C 20 -alkyl,

X 1 is selected from the group consisting of halogen, and esterified sulfonate, and

wherein n is an integer from 2 to 10.

2. A monomer of the formula III a

wherein the variables are defined as follows:

a is an integer from 0 to 3,

R 1 , R 2 , R 3 are identical or different and are selected independently from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl containing one or more Si, N, P, O or S atoms, C 6 -C 30 -aryl, C 4 -C 14 -heteroaryl containing at least one S or N atom, —N(C 6 -C 14 -aryl) 2 , and Y 1 ,

wherein Y 1 may be identical or different and are selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 , glycidyl,

wherein Y 2 is selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 and glycidyl, and one or more groups Y 1 or Y 2 may be crosslinked to one another,

R 6 are identical or different and are each, depending on one another, hydrogen or C 1 -C 20 -alkyl,

X 1 is selected from the group consisting of halogen, and esterified sulfonate, and

wherein n is an integer from 2 to 10.

3. The monomer according to claim 1 , wherein a is 0 and R 1 and R 2 are hydrogen.

4. A process for preparing monomers of the formula III, comprising:

metalating compounds of the formula IV,

wherein X 3 and X 4 are identical or different and are selected from the group consisting of halogen and sulfonate,

using at least two or at least four equivalents of a strong organometallic base, to obtain a product, and

subsequently reacting the product with one or two equivalents of a boron compound of the formula V

wherein X 5 is selected from the group consisting of C 1 -C 6 -alkoxy, to obtain said compound of formula III

a is an integer from 0 to 3,

R 1 , R 2 , R 3 are identical or different and are selected independently from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl containing one or more Si, N, P, O or S atoms, C 6 -C 30 -aryl, C 4 -C 14 -heteroaryl containing at least one S or N atom, —N(C 6 -C 14 -aryl) 2 , and Y 1 ,

wherein Y 1 may be identical or different and are selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 , glycidyl,

wherein Y 2 is selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 and glycidyl, and one or more groups Y 1 or Y 2 may be crosslinked to one another,

R 6 are identical or different and are each, depending on one another, hydrogen or C 1 -C 20 -alkyl,

X 1 is selected from the group consisting of halogen, and esterified sulfonate, wherein R 6 is as defined above, and

wherein n is an integer from 2 to 10.

5. A process as claimed in claim 4 , wherein the compound of formula III is represented by formula IIIa and the compound of formula IV is represented by formula IV a,

wherein the compound of formula IV a is as follows:

wherein X 3 and X 4 are identical or different and are selected from the group consisting of halogen and sulfonate,

wherein the compound of formula III a is as follows

wherein the variables in formula IIIa and formula IVa are defined as follows:

a is an integer item 0 to 3,

R 1 , R 2 , R 3 are identical or different and are selected independently from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyl containing one or more Si, N, P, O or S atoms, C 6 -C 30 -aryl, C 4 -C 14 -heteroaryl containing at least one S or N atom, —N(C 4 -C 14 -aryl) 2 , and Y 1 ,

wherein Y 1 may be identical or different and are selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 ,acryloyl, methacryloyl, methylstyryl,

—O—CH═CH 2 , glycidyl,

wherein Y 2 is selected from the group consisting of —CH═CH 2 , trans-CH═CH—C 6 H 5 , cis-CH═CH—C 6 H 5 , acryloyl, methacryloyl, methylstyryl, —O—CH═CH 2 , and glycidyl, and one or more groups Y 1 or Y 2 may be crosslinked to one another,

R 6 are identical or different and are each, depending on one another, hydrogen or C 1 -C 20 -alkyl,

X 1 is selected from the group consisting of halogen, and esterified sulfonate and

wherein n is an integer from 2 to 10.

6. The process according to claim 4 , wherein X 5 in formula V is isopropoxy.

7. The process according to claim 4 , wherein X 3 and X 4 are each triflate.

8. The process according to claim 4 , wherein said base is a methyl alkyl.

9. The process according to claim 4 , wherein said metalation proceeds for 1 to 10 hours.

10. The process according to claim 4 , wherein a reaction temperature during metalation is −90° to −20° C.

11. The process according to claim 4 , wherein a reaction temperature during reaction with said boron compound is −100° to +150° C.

12. The process according to claim 4 , wherein said reaction with said boron compound is carried out in the absence of oxygen and moisture.

13. The process according to claim 4 , wherein said reaction with said boron compound proceeds for 10 minutes to 2 days.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/901,736 PREVIOUSLY RECORDED AT REEL: 039460 FRAME: 0615. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 8, 2017
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 042740/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2016
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 039460/0615 →
Priority Claims (1)
DE 102 11 648 · Mar 15, 2002 · national
Continuity (2)
Division 1037778800 · Mar 4, 2003
Related Publication 20050159582A1 · Jul 21, 2005