Functionalized thermoplastic polyurethane, method for producing same, method for producing highly functional medical composite material using same, and medical device including same

Patent metadata

Field	Value
Publication number	US-2023257507-A1
Application number	US-202118014199-A
Country	US
Kind code	A1
Filing date	Jul 8, 2021
Priority date	Jul 8, 2020
Publication date	Aug 17, 2023
Grant date	—

Abstract

The present invention pertains to: a functionalized thermoplastic polyurethane containing a novel chain extender having functionality capable of chemically bonding to a prepolymer polymerized by reacting a polyol (P) with a diisocyanate (R); a functional composite material containing one or more monomers or polymers selected from the group consisting of an anionic functional group, an amphoteric functional group, a perfluorinated compound, a hydrogel, and a silicone polymer; a method for producing same; and an article including same.

First claim

1 . A functionalized thermoplastic polyurethane, represented by Chemical formula 1 below:

in the formula,
Fn is selected from the group consisting of a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted thiol group having 2 to 10 carbon atoms, a substituted or unsubstituted alkylazide group having 2 to 10 carbon atoms, a substituted or unsubstituted arylazide group having 7 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 2 to 10 carbon atoms, a substituted or unsubstituted isocyanate group having 2 to 10 carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 20 carbon atoms, a substituted or unsubstituted alcohol group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 2 to 10 carbon atoms, and a substituted or unsubstituted alkylhalogen group having 2 to 20 carbon atoms; and
L is one kind selected from the group consisting of O, C, S, N, P, Si, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted ethylene oxide group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms and a substituted or unsubstituted siloxane group having 5 to 20 carbon atoms; and
E is one kind selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted ethylene oxide group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and a substituted or unsubstituted siloxane group having 5 to 20 carbon atoms; and
P is a polyol; and
R is a diisocyanate; and
x is an integer of 2 to 50; and
y is an integer of 2 to 100,
wherein the molecular weight of the polyol (P) is 400 g/mol˜10,000 g/mol.

2 . The functionalized thermoplastic polyurethane according to claim 1 , wherein a chain extender of Chemical formula 2 below is introduced:

in the formula, E, Fn and L are as defined in Chemical formula 1.

3 . (canceled)

4 . The functionalized thermoplastic polyurethane according to claim 1 , wherein the polyol (P) is one or more kinds of polyols selected from the group consisting of polyether, polycarbonate, polyester and silicone.

5 . The functionalized thermoplastic polyurethane according to claim 4 , wherein the polyether polyol is one or more kinds selected from the group consisting of polyethyleneglycol (PEG), polypropyleneglycol (PPG) and polytetramethyleneglycol (PTMG), and the polycarbonate polyol is one or more kinds selected from the group consisting of poly(1,6-hexamethylene carbonate)diol (PHMCD), poly(decamethylene carbonate)diol (PDMCD), oligocarbonate diol and polyhexamethylene-pentamethylene carbonate diol (PHMPMCD), and the polyester polyol is one or more kinds selected from the group consisting of polylactide (PLA), polycaprolactone (PCL) and polyethyleneglycol adipate (PEGA), and the silicone polyol is one or more kinds selected from the group consisting of polydimethyl siloxane (PDMS), polyaryl siloxane and polyalkyl siloxane and combinations thereof.

6 . The functionalized thermoplastic polyurethane according to claim 1 , wherein the mean molecular weight of each polyol (P) is 400 g/mol to 10,000 g/mol.

7 . The functionalized thermoplastic polyurethane according to claim 1 , wherein the diisocyanate (R) is one or more kinds selected from the group consisting of 4,4′-dicyclohexylmethane diisocyanate (HMDI), isophorone diisocyanate (IPDI), 1,4-cyclohexylmethane diisocyanate (CHDI), 4,4′-diphenylmethane diisocyanate (MDI), 2,4- or 2,6-toluene diisocyanate (TDI), carbodiimide-modified MDI, polymeric MDI, and hexamethylene diisocyanate.

8 . The functionalized thermoplastic polyurethane according to claim 1 , wherein the functionalized thermoplastic polyurethane copolymer is represented by a structure selected from the group consisting of Chemical formulas 3 to 14 below:

in the Chemical formulas 3 to 14,
x and y are as defined in Chemical formula 1 above, and
n is an integer of 10 to 250.

9 . A chain extender represented by Chemical formula 2 below:

in the formula,
Fn is selected from the group consisting of a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted thiol group having 2 to 10 carbon atoms, a substituted or unsubstituted alkylazide group having 2 to 10 carbon atoms, a substituted or unsubstituted arylazide group having 7 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 2 to 10 carbon atoms, a substituted or unsubstituted isocyanate group having 2 to 10 carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 20 carbon atoms, a substituted or unsubstituted alcohol group having 2 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 2 to 10 carbon atoms and a substituted or unsubstituted alkylhalogen group having 2 to 20 carbon atoms;
L is one kind selected from the group consisting of O, C, S, N, P, Si, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted ethylene oxide group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and a substituted or unsubstituted siloxane group having 5 to 20 carbon atoms; and
E is one kind selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted ethylene oxide group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 7 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and a substituted or unsubstituted siloxane group having 5 to 20 carbon atoms.

10 . The chain extender according to claim 9 ,
wherein the chain extender represented by Chemical formula 2 above is selected from the group consisting of Chemical formulas 15 to 18 below.

11 . A functional composite, comprising a functional thermo

Assignees

• I Sens Inc

Inventors

• Shin Hyunseo
• Yang Bona
• Kang Young Jea
• Kang Geunhee

Classifications

• C08L2203/02

  for biomedical use · CPC title

• C08L2203/20

  use in electrical or conductive gadgets · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G18/4833

  Polyethers containing oxyethylene units · CPC title

• C08G18/44

  Polycarbonates · CPC title