Dissoluble PDMS-modified p(HEMA-MAA) amphiphilic copolymer and method for fabricating the same

Patent metadata

Field	Value
Publication number	US-8937133-B2
Application number	US-201414255737-A
Country	US
Kind code	B2
Filing date	Apr 17, 2014
Priority date	Sep 25, 2012
Publication date	Jan 20, 2015
Grant date	Jan 20, 2015

Abstract

The present invention discloses a dissoluble PDMS-modified p(HEMA-MAA) amphiphilic copolymer and the method of fabricating the same. The amphiphilic copolymer of the present invention is fabricated via chemically bonding HEMA, MAA, and poly(dimethylsiloxane), bis(3-aminopropyl) terminated (PDMS) in aqueous solution. The PDMS-modified p(HEMA-MAA) amphiphilic copolymer can be dissolved completely in polar solvents, particularly alcohol solvents, to facilitate subsequent processing. The amphiphilic copolymer features adjustable hydrophobic-hydrophilic properties and exhibits excellent biocompatibility. Thus, it can be utilized in a number of advanced applications, including anti-fouling and drug delivery.

First claim

What is claimed is:

1. A dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer, comprising compounds respectively expressed by Structural Formula I and Structural Formula II:

and wherein m is an arbitrary integer of 1˜10, n is an arbitrary integer of 1˜40, x is an arbitrary integer of 1˜10, y is an arbitrary integer of 1˜10, and o is an arbitrary integer of 1˜10.

2. The dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer according to claim 1 , which is dissoluble in polar solvents.

3. The dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer according to claim 2 , wherein said polar solvents include ethanol, propanol, isopropyl alcohol, polyethylene glycol, polypropylene glycol, methyl sulfoxide, and mixtures thereof.

4. The dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer according to claim 1 , which self-assembles in an aqueous solution to form spherical nanoparticles having a diameter of 30-40 nm.

5. The dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer according to claim 1 , which has a molecular weight of 3500-30000.

6. The dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer according to claim 1 , which is fabricated into a transparent film or a nanoparticle, wherein said transparent film or said nanoparticle is used to transport drugs.

7. A method for fabricating a dissoluble poly(dimethylsiloxane)-modified poly(2-hydroxyethyl methacrylate-methacrylic acid) amphiphilic copolymer, comprising steps:
dissolving 2-hydroxyethyl methacrylate (HEMA) and methacrylic acid (MAA) in deionized water to form a first solution, adding a photo initiator to said first solution to form a second solution, agitating said second solution uniformly, and illuminating said second solution with ultraviolet ray to polymerized compounds in said second solution to form a third solution, which is a white-colored solution containing a copolymer;
adding an activating reagent and an alcohol solvent to said third solution containing said copolymer to form a fourth solution, and agitating said fourth solution uniformly to form a mixture solution;
slowly dripping a dimethylsiloxane (DMS) solution to said mixture solution to form a fifth solution, adding a catalyst to said fifth solution to form a sixth solution, and agitating said sixth solution uniformly to form a solution of a poly(dimethylsiloxane)(PDMS)-modified poly(HEMA-MAA) amphiphilic copolymer.

8. The method according to claim 7 , wherein said HEMA and said MAA are mixed by a weight ratio of from 100:10 to 100:100.

9. The method according to claim 8 , wherein said HEMA plus said MAA and said deionized water are mixed by a weight ratio of from 1:100 to 10:100.

10. The method according to claim 7 further comprising a step of dialyzing said solution of said PDMS-modified p(HEMA-MAA) amphiphilic copolymer to form powdered PDMS-modified p(HEMA-MAA) amphiphilic copolymer.

11. The method according to claim 10 , wherein said powdered PDMS-modified p(HEMA-MAA) amphiphilic copolymer is dissoluble in polar solvents.

12. The method according to claim 11 , wherein said polar solvents include ethanol, propanol, isopropyl alcohol, polyethylene glycol, polypropylene glycol, methyl sulfoxide, and mixtures thereof.

13. The method according to claim 10 , wherein isopropyl alcohol, propanol or ethanol is used as a dialysate in said step of dialyzing said solution of said PDMS-modified p(HEMA-MAA) amphiphilic copolymer.

14. The method according to claim 10 , wherein said powdered amphiphilic copolymer dissolves in an aqueous solution and self-assembles into spherical nanoparticles having a diameter of 30-40 nm in an aqueous solution.

15. The method according to claim 7 , wherein said DMS solution is a mixture of DMS and an alcohol solvent.

16. The method according to claim 15 , wherein said copolymer is covalently bonded with said DMS by a ratio of from 100:1 to 100:40.

17. The method according to claim 15 , wherein said alcohol solvent is ethanol, propanol, isopropyl alcohol, polyethylene glycol, polypropylene glycol, or a mixture thereof.

18. The method according to claim 7 , wherein said photo initiator is 2-hydroxy-2-methyl propiophenone (Darocur 1173).

19. The method according to claim 7 , wherein said alcohol solvent is selected from a group consisting of ethanol, propanol, isopropyl alcohol, polyethylene glycol, polypropylene glycol, and mixtures thereof.

20. The method according to claim 7 , wherein said activating reagent is N-hydroxysuccinimide (NHS).

21. The method according to claim 7 , wherein said catalyst is 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC).

Assignees

• Univ Nat Chiao Tung

Inventors

• Liu Dean-Mo
• Huang Yun-Chun
• Hsu Chung-Yu

Classifications

• C08F265/00

  Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 · CPC title

• C08F8/00

  Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C) · CPC title

• C08F220/28 Primary

  containing no aromatic rings in the alcohol moiety · CPC title

• C08F8/42 Primary

  Introducing metal atoms or metal-containing groups · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title