Nonionic telechelic polymers incorporating polyhedral oligosilsesquioxane (POSS) and uses thereof

• US 20040024098A1
• Filed: 07/16/2003
• Published: 02/05/2004
• Est. Priority Date: 07/30/2002
• Status: Active Grant

• Current Assignee: University of Connecticut (State of Connecticut)
• Original Assignee: University of Connecticut (State of Connecticut)
• Inventors: Kim, Byoung-Suhk, Mather, Patrick T., Liu, Changdeng, Ge, Qing
• Granted Patent: US 7,067,606 B2
• Time in Patent Office: Days
• US Class Current: 524/268
• CPC Class Codes: C08G 18/3893 containing silicon
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/718 containing silicon
• CPC Class Codes: C08G 65/336 containing silicon
• CPC Class Codes: C08L 2205/05 containing polymer components which can react with one another
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers

Abstract

Amphiphilic telechelics incorporating polyhedraloligosilsesquioxane (POSS) synthesized by direct urethane linkage between the diol end groups of polyethylene glycol (PEG) homopolymers and the monoisocyanate group of POSS macromers. The hydrophobicity of the amphiphilic telechelics can be varied by using PEG homopolymers of increasing MW, providing for control over molecular architecture by hydrophilic/hydrophobic balance. Methods for synthesizing the amphiphilic telechelics and their use as surfactants, thickening agents, additives to plastic such as PMMA′(Plexiglass), epoxyadhesives for improving their properties are also disclosed.

Claims

1. An amphiphilic telechelic incorporating POSS having the following structure

2. An amphiphilic telechelic incorporating POSS according to claim 1 wherein R is cyclohexyl.

3. An amphiphilic telechelic incorporating POSS according to claim 1 wherein n is 1 to 23,000.

4. An amphiphilic telechelic incorporating POSS according to claim 1 having a POSS content from about 19.0 to about 70.0 wt %.

5. An amphiphilic telechelic incorporating POSS according to claim 1 having molecular weight of about 3300 to 13,000 g/mol.

8. A method according to claim 5 wherein said polyethylene glycol has a molecular weight of about 62-1,000,000 g/mol.

17. A nonionic surfactant characterized by enhanced thickening behavior comprising an amphiphilic telechelic according to claim 1.

18. A toughening additive for polymers selected from the group consisting of epoxy, polymethylmethacrylate, polyvinylacetate, polyethylmethacrylate, sulfonated styrene and polysulfone comprising an amphiphilic telechelic according to claim 1.

19. A solid polymer electrolyte, consisting of an amphiphilic telechelic according to claim 1 or a blend of such amphiphilic telechelic with unmodified PEGs, with high ionic conductivity for battery applications.

6. A method for forming amphiphilic telechelics incorporating POSS which comprises reacting polyethylene glycol homopolymer and POSS macromer wherein the monoisocyanate groups of two of said POSS macromers are directly linked between the diol end groups of said polyethylene glycol homopolymer.

7. A method according to claim 6 wherein said reaction is carried out in the presence of dibutyl tin dilaurate as catalyst.

9. A method according to claim 6 wherein said polyethylene glycol has a molecular weight of about 100 to 10,000 g/mol.

10. A method according to claim 6 wherein said POSS macromer has the formula

11. A method according to claim 6 wherein said POSS macromer is isocyanatodimethylsilylcyclohexyl-POSS.

12. A method according to claim 6 wherein said polyethylene glycol has a molecular weight of about 62-1,000,000 g/mol and said POSS macromer is isocyanatodimethylsilylcyclohexyl-POSS.

13. A method according to claim 6 wherein the ratio of polyethylene glycol to POSS macromer used in the reaction is about 1:

1.8-2.20.

14. A method according to claim 6 which comprises introducing the POSS macromer into the reaction in an amount to provide about 19.0 to about 70.0 wt % of POSS macromer in the amphiphilic telechelic produced.

15. An amphiphilic telechelic made by the method of claim 6.

16. An amphiphilic telechelic made by the method of claim 11.

20. A method of preparing a shape memory polymer which comprises reacting a polyol, a diosocyanate, and a chain extender selected from the group consisting of TMP cyclopentyldiol-POSS, TMP cyclohexyldiol-POSS, TMP isobutydiol-POSS, transcyclohexanediolcyclohexane-POSS and transcyclohexanediolisobutyl-POSS.

21. A shape memory polymer produced by the method of claim 20.