IP Library Granted Patent US 7,915,332
Granted Patent B2
US 7,915,332 · App. 11/766,227 · Granted Mar 29, 2011

Compositions and methods for polymer composites

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Quick Facts
Patent No.
US 7,915,332
App. No.
11/766,227
Granted
Mar 29, 2011
Kind
B2
Abstract

This invention relates to organic salt compositions useful in the preparation of organoclay compositions, polymer-organoclay composite compositions, and methods for the preparation of polymer nanocomposites. In one embodiment, the present invention provides an organoclay composition comprising alternating inorganic silicate layers and organic layers, said organic layers comprising a quaternary phosphonium cation having structure X wherein Ar 1 , Ar 2 , and Ar 3 are independently C 2 -C 50 aromatic radicals; Ar 4 is a bond or a C 2 -C 50 aromatic radical; “a” is a number from 1 to about 200; “c” is a number from 0 to 3; R 1 is independently at each occurrence a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, or a C 2 -C 20 aromatic radical; and R 2 is a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, a C 2 -C 50 aromatic radical, or a polymer chain.

Claims (31)

1. An organoclay composition comprising alternating inorganic silicate layers and organic layers, said organic layers comprising a quaternary phosphonium cation having structure X

wherein Ar 1 , Ar 2 , and Ar 3 are independently C 3 -C 50 aromatic radicals; Ar 4 is a bond or a C 3 -C 50 aromatic radical; “a” is a number from 1 to about 200; “c” is a number from 0 to 3; R 1 is independently at each occurrence a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, or a C 3 -C 50 aromatic radical; and R 2 is a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, a C 3 -C 50 aromatic radical, or a polymer chain.

2. The organoclay composition according to claim 1 , wherein Ar 4 is a bond.

3. The organoclay composition according to claim 1 , wherein R 2 is a polyetherimide polymer chain.

4. The organoclay composition according to claim 1 , wherein R 2 is a polyether ketone polymer chain.

5. The organoclay composition according to claim 1 , wherein R 2 is a polymer chain having a number average molecular weight M n in a range from about 1000 to about 50,000 grams per mole.

6. The organoclay composition according to claim 1 , wherein R 2 is a polymer chain having a number average molecular weight M n in a range from about 1000 to about 20,000 grams per mole.

7. The organoclay composition according to claim 1 , wherein R 2 is a polymer chain having a number average molecular weight M n in a range from about 1000 to about 5,000 grams per mole.

8. The organoclay composition according to claim 1 , wherein R 2 is a polyetherimide polymer chain having a number average molecular weight M n in a range from about 1000 to about 50,000 grams per mole.

9. The organoclay composition according to claim 1 , wherein R 2 is a polyetherimide polymer chain having a number average molecular weight M n in a range from about 1000 to about 20,000 grams per mole.

10. The organoclay composition according to claim 1 , wherein said quaternary phosphonium cation has structure XI

11. The organoclay composition according to claim 1 , wherein said quaternary phosphonium cation has structure XII

12. The organoclay composition according to claim 1 , wherein the inorganic silicate layers are derived from an inorganic clay selected from the group consisting of kaolinite, dickite, nacrite, halloysite, antigorite, chrysotile, pyrophyllite, montmorillonite, beidellite, nontronite, saponite, sauconite, stevensite, hectorite, tetrasilylic mica, sodium taeniolite, muscovite, margarite, talc, vermiculite, phlogopite, xanthophyllite, chlorite, and combinations thereof.

13. The organoclay composition according to claim 1 , wherein the inorganic silicate layers are derived from an inorganic clay comprising a synthetic clay.

14. The organoclay composition according to claim 1 , wherein the inorganic silicate layers are derived from montmorillonite.

15. The organoclay composition according to claim 1 , wherein the organoclay composition is characterized by an interlayer distance of from about 5 to about 100 Angstroms.

16. A method for the preparation of an organoclay composition comprising a quaternary phosphonium cation having structure X

wherein Ar 1 , Ar 2 , and Ar 3 are independently C 3 -C 50 aromatic radicals; Ar 4 is a bond or a C 3 -C 50 aromatic radical; “a” is a number from 1 to about 200; “c” is a number from 0 to 3; R 1 is independently at each occurrence a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, or a C 3 -C 50 aromatic radical; and R 2 is a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, a C 3 -C 50 aromatic radical, or a polymer chain;

said method comprising:

(a) contacting in a first reaction mixture an organophosphonium salt having structure I

wherein Ar 1 , Ar 2 , and Ar 3 are independently C 3 -C 50 aromatic radicals; Ar 4 is a bond or a C 3 -C 50 aromatic radical; “a” is a number from 1 to about 200; “c” is a number from 0 to 3; R 1 is independently at each occurrence a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, or a C 3 -C 50 aromatic radical; R 2 is a halogen atom, a C 1 -C 20 aliphatic radical, a C 5 -C 20 cycloaliphatic radical, a C 3 -C 50 aromatic radical, or a polymer chain; and X − is a charge balancing counterion;

with a layered silicate in the presence of a solvent; and isolating the product organoclay composition

(b) isolating the product organoclay composition.

17. The method according to claim 16 , wherein said contacting is carried out in a solvent comprising at least one organic solvent.

18. The method according to claim 16 , wherein said contacting is carried out in a solvent comprising water.

19. The method according to claim 16 , wherein said layered silicate comprises an inorganic clay selected from the group consisting of kaolinite, dickite, nacrite, halloysite, antigorite, chrysotile, pyrophyllite, montmorillonite, beidellite, nontronite, saponite, sauconite, stevensite, hectorite, tetrasilylic mica, sodium taeniolite, muscovite, margarite, talc, vermiculite, phlogopite, xanthophyllite, chlorite, and combinations thereof.

20. The method according to claim 16 , wherein the inorganic silicate layers are derived from an inorganic clay comprising a synthetic clay.

21. The method according to claim 16 , wherein said layered silicate comprises montmorillonite clay.

22. An organoclay composition comprising alternating inorganic silicate layers and organic layers, said organic layers comprising a polymeric quaternary phosphonium cation, wherein said polymeric quaternary phosphonium cation comprises structure XIII

wherein m is a number in a range from about 10 to about 1000; and Ar 5 is a C 2 -C 50 aromatic radical, or a polymer chain.

23. The organoclay composition according to claim 22 , wherein Ar 5 is an aromatic radical having structure XIV

Assignments (5)
CHANGE OF NAME Recorded Jun 6, 2016
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 038883/0816 →
RELEASE OF SECURITY INTEREST Recorded Mar 17, 2014
From: CITIBANK, N.A.
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 032459/0798 →
SECURITY AGREEMENT Recorded Aug 18, 2008
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021423/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2008
From: GENERAL ELECTRIC COMPANY
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 020985/0551 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 28, 2007
From: CHAN, KWOK PONG; CROLL, JOSHUA MCCLELLAN; GANESAN, BALAKRISHNAN; HARRIGAN, MARCUS J.; KHOURI, FARID FOUAD; KISHAN, GURRAM; MATHUR, RITESH; SUFFIELD, RACHEL MARIE; WANG, WENHUI; WHITE, JAMES MITCHELL
To: GENERAL ELECTRIC COMPANY
Reel/Frame 019753/0185 →