IP Library Granted Patent US 6,844,416
Granted Patent B2
US 6,844,416 · App. 10/428,969 · Granted Jan 18, 2005

Polycarbonates

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Quick Facts
Patent No.
US 6,844,416
App. No.
10/428,969
Granted
Jan 18, 2005
Kind
B2
Abstract

A polycarbonate comprised of a repeating unit represented by Formula (I) with R 1 , R 2 , R 3 and R 4 being, for example, alkyl; Ar being, for example, aryl; and m representing the number of groups.

Claims (38)

1. A polycarbonate comprised of a repeating unit represented by Formula (I)

wherein R 1 is selected from the group consisting of hydrogen, alkyl containing from about 1 to about 12 carbon atoms, halogenated alkyl containing from about 1 to about 25 carbon atoms, optionally as alkyl containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, silicon, and phosphorus; aryl optionally containing from about 6 to about 15 carbon atoms or substituted aryl optionally containing from about 6 to about 15 carbon atoms; R 2 represents a divalent linkage optionally selected from the group consisting of alkylene of from 1 to about 15 carbon atoms, alkylene of from 1 to about 15 carbon atoms containing one or more heteroatoms of halogen, nitrogen, oxygen, sulfur, silicon, and phosphorus, arylalkylene of optionally from 1 to about 15 carbon atoms, and arylene optionally of from 1 to about 15 carbon atoms; Ar 1 and Ar 2 each independently represent aromatic groups optionally containing from about 6 to about 30 carbon atoms; n represents the number of segments of from 1 to about 10; R 3 represents an alkyl group optionally containing from about 1 to about 10 carbon atoms, an aryl group containing from about 6 to about 15 carbon atoms; R 4 represents an alkyl group optionally containing from about 1 to about 5 carbon atoms; and m is 0, 1 or 2.

2. A polycarbonate in accordance with claim 1 wherein said alkyl for R 1 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, and hexyl.

3. A polycarbonate in accordance with claim 1 wherein said halogenated alkyl for R 1 is selected from the group consisting of fluoroalkyl, perfluoroalkyl, and chloroalkyl.

4. A polycarbonate in accordance with claim 1 wherein R 2 is a divalent linkage of alkylene selected from the group consisting of dimethylene, trimethylene, and tetramethylene.

5. A polycarbonate in accordance with claim 1 wherein Ar 1 and Ar 2 are arylene groups independently selected from the group consisting of

and wherein said arylene optionally contains a substituent selected from the group consisting of hydrogen, halogen, alkyl of from 1 to about 15 carbons, halogenated alkyl of 1 to about 15 carbons, alkyl containing one or more heteroatoms of nitrogen, oxygen, sulfur, silicon, and phosphorus.

6. A polycarbonate in accordance with claim 1 wherein R 3 is selected from the group consisting of methyl, ethyl, propyl, butyl, and phenyl.

7. A polycarbonate in accordance with claim 1 wherein R 4 is selected from the group consisting of methyl, ethyl, propyl, and isopropyl.

8. A polycarbonate comprised of a repeating unit represented by Formula (I)

wherein R 1 is selected from the group consisting of hydrogen, alkyl containing from about 1 to about 15 carbon atoms, halogenated alkyl containing from about 1 to about 15 carbon atoms, alkyl containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, silicon, and phosphorus; aryl containing from about 6 to about 15 carbon atoms or substituted aryl containing from about 6 to about 15 carbon atoms; R 2 represents a divalent linkage selected from the group consisting of alkylene of from 1 to about 15 carbon atoms, alkylene of from 1 to about 15 carbon atoms containing one or more heteroatoms of halogen, nitrogen, oxygen, sulfur, silicon, and phosphorus, arylalkylene of from 1 to about 15 carbon atoms, and arylene of from 1 to about 15 carbon atoms; Ar 1 and Ar 2 each independently represent aromatic groups containing from about 6 to about 30 carbon atoms; n represents the number of segments of from 1 to about 10; R 3 represents an alkyl group containing from about 1 to about 10 carbon atoms, an aryl group containing from about 6 to about 15 carbon atoms; R 4 represents an alkyl group containing from about 1 to about 5 carbon atoms, and m is 0, 1 or 2; and one or more repeating units represented by Formula (II)

wherein A is a divalent hydrocarbon linkage of from about 2 to about 30 carbons, or optionally a divalent hydrocarbon linkage of from about 2 to about 30 carbon atoms further containing a heteroatom of oxygen, nitrogen, sulfur, silicon, and phosphorus.

9. A polycarbonate composition in accordance with claim 8 wherein A is selected from the group consisting of

10. A polycarbonate as represented by Formula (III)

wherein R 1 is selected from the group consisting of hydrogen, alkyl of from about 1 to about 15 carbon atoms, a halogenated alkyl of from about 1 to about 15 carbon atoms, an alkyl of from about 1 to about 15 carbon atoms further containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, silicon, and phosphorus, an aryl or substituted aryl of from about 6 to about 30 carbon atoms; R 2 represents a divalent linkage, which is selected from the group consisting of an alkylene of from about 1 to about 15 carbon atoms; n is an integer selected from 1 to about 10; R 3 represents an alkyl group containing from about 1 to about 10 carbon atoms, an aryl group containing from about 6 to about 15 carbon atoms; R 4 represents an alkyl group containing from about 1 to about 5 carbon atoms, m is 0, 1 or 2; Ar 3 and Ar 4 each independently represent aromatic groups of from about 6 to about 30 carbon atoms; R 5 and R 6 are independently selected from the group consisting of hydrogen, alkyl of from about 1 to about 15 carbon atoms, aryl or substituted aryl of from about 6 to about 30 carbon atoms; wherein R 5 and R 6 may form a combined ring structure containing from about 5 to about 20 carbon atoms; and wherein x and y are the mole fractions of the repeating units such that x+y is equal to 1.

11. A polycarbonate in accordance with claim 10 wherein said alkyl for R 1 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, and hexyl.

12. A polycarbonate in accordance with claim 10 wherein said halogenated alkyl for R 1 is selected from the group consisting of fluoroalkyl, perfluoroalkyl, and chloroalkyl.

13. A polycarbonate in accordance with claim 10 wherein R 2 is selected from the group consisting of dimethylene, trimethylene, and tetramethylene.

14. A polycarbonate in accordance with claim 10 wherein Ar 3 and Ar 4 are arylene groups independently selected from the group consisting of the following formula

and wherein said arylene optionally contains a substituent selected from the group consisting of hydrogen, halogen, alkyl of from 1 to about 15 carbon atoms, halogenated alkyl of 1 to about 15 carbon atoms, and alkyl containing one or more heteroatoms of nitrogen, oxygen, sulfur, silicon, or phosphorus.

15. A polycarbonate in accordance with claim 10 wherein R 3 is selected from the group consisting of methyl, ethyl, propyl, butyl and phenyl.

16. A polycarbonate in accordance with claim 10 wherein R 4 is alkyl selected from the group consisting of methyl, ethyl, propyl, and isopropyl.

17. A polycarbonate in accordance with claim 10 wherein R 5 and R 6 are alkyl independently selected from the group consisting of methyl, ethyl, propyl, trifluoromethyl, and 3,3,3-trifluoropropyl.

18. A polycarbonate in accordance with claim 10 wherein R 5 and R 6 form a combined ring structure of from about 5 to about 10 members.

19. A polycarbonate in accordance with claim 10 wherein R 1 is methyl; R 2 is trimethylene; R 4 is methyl; n is 3, and m is 0.

20. A polycarbonate in accordance with claim 10 wherein said polycarbonate possesses a weight average molecular weight of from about 2,000 to about 500,000.

21. A polycarbonate in accordance with claim 10 wherein said polycarbonate is comprised of

wherein x and y are the mole fractions of the repeating units such that x+y is equal to 1, and wherein said polycarbonate possesses a molecular weight of from about 2,000 to about 500,000.

22. A polycarbonate in accordance with claim 10 wherein said polycarbonate is crosslinked by hydrolysis and condensation of the pendent silane group with itself or with other silane coupling agents.

23. A polycarbonate in accordance with claim 22 wherein said crosslinked product is of the following formulas

wherein R 1 is selected from the group consisting of hydrogen, alkyl of from about 1 to about 12 carbon atoms, a halogenated alkyl of from about 1 to about 15 carbon atoms, an alkyl of from about 1 to about 12 carbon atoms further containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, silicon, and phosphorus, aryl of from about 6 to about 30 carbon atoms; R 2 represents a divalent linkage, which is selected from the group consisting of an alkylene of from about 1 to about 15 carbon atoms, Ar 3 and Ar 4 each independently represent aromatic groups of from about 6 to about 30 carbon atoms; R 5 and R 6 are independently selected from the group consisting of hydrogen, alkyl of from about 1 to about 12 carbon atoms, aryl of from about 6 to about 30 carbon atoms; n is from 1 to about 5; wherein x and y are the mole fractions of the repeating units such that x+y is equal to 1.

24. A polycarbonate in accordance with claim 23 wherein said crosslinked product is of the following formula

25. A polycarbonate in accordance with claim 22 wherein said silane coupling agent is tetraalkyl orthosilicate, trialkoxysilane, dialkoxysilane, or a silane containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and phosphorus.

26. A polycarbonate in accordance with claim 22 wherein said silane coupling agent is tetraethyl orthosilicate, tetrapropyl orthosilicate, methyltrimethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, 3-aminopropyltrimethoxysilane, N-[3-(trimethoxysilyl)propyl]-ethylenediamine, or 3-glycidoxypropyltrimethoxysilane.

27. A process for the preparation of the polycarbonates of Formula III which process comprises the reaction of a hydroxyl polycarbonate and an isocyanatoalkoxysilane, which reaction is at a temperature of from about 50° C. to about 200° C.

28. A process in accordance with claim 27 wherein said isocyanatoalkoxysilane is 3-(triethoxysilyl)propyl isocyanate, 3-(trimethoxysilyl)propyl isocyanate, 3-(triisopropoxysilyl)propyl isocyanate, or 3-(diethoxymethylsilyl)propyl isocyanate.

29. A polycarbonate comprised of a repeating unit represented by Formula (I)

wherein R 1 is selected from the group consisting of hydrogen, alkyl, halogenated alkyl, and aryl; R 2 represents a divalent linkage; Ar 1 and Ar 2 each independently represent aromatic groups; n represents the number of segments or units; R 3 represents an alkyl group, or an aryl group; R 4 represents an alkyl group; and m is 0, 1 or 2.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Sep 7, 2022
From: JPMORGAN CHASE BANK, N.A. AS SUCCESSOR-IN-INTEREST ADMINISTRATIVE AGENT AND COLLATERAL AGENT TO JPMORGAN CHASE BANK
To: XEROX CORPORATION
Reel/Frame 066728/0193 →
RELEASE OF SECURITY INTEREST Recorded Aug 31, 2022
From: JPMORGAN CHASE BANK, N.A. AS SUCCESSOR-IN-INTEREST ADMINISTRATIVE AGENT AND COLLATERAL AGENT TO BANK ONE, N.A.
To: XEROX CORPORATION
Reel/Frame 061360/0628 →
SECURITY AGREEMENT Recorded Jun 30, 2005
From: XEROX CORPORATION
To: JP MORGAN CHASE BANK
Reel/Frame 016761/0158 →
SECURITY AGREEMENT Recorded Oct 31, 2003
From: XEROX CORPORATION
To: JPMORGAN CHASE BANK, AS COLLATERAL AGENT
Reel/Frame 015134/0476 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2003
From: QI, YU; HU, NAN-XING; GOODBRAND, H. BRUCE; SMITH, PAUL F.; ALLEN, C. GEOFFREY
To: XEROX CORPORATION
Reel/Frame 014045/0879 →