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Random copolymer of oxazoline

Foreign code F110003658
File No. A252-32WO
Posted date Jun 30, 2011
Country EPO
Application number 06797486
Gazette No. 1930361
Gazette No. 1930361
Date of filing Aug 30, 2006
Gazette Date Jun 11, 2008
Gazette Date Apr 16, 2014
International application number JP2006317587
International publication number WO2007026932
Date of international filing Aug 30, 2006
Date of international publication Mar 8, 2007
Priority data
  • 2006JP317587 (Aug 30, 2006) WO
  • P2005-253977 (Sep 1, 2005) JP
Title Random copolymer of oxazoline
Abstract The invention provides approximately monodispersible random copolymers obtained from monomeric mixtures of 2-ethyl-2-oxazoline with 2-isopropyl-2-oxazoline, production method thereof and 2-isopropyl-2-oxazoline homopolymer obtained by using special initiator.
Such polymers exhibit temperature-responsiveness in an aqueous solution within a broad temperature range, and are useful materials in the technical fields of surface chemistry and biomaterials.(see diagramm)
Scope of claims [claim1]
1. A random copolymer represented by the following formula (A): (see diagramm) in the formula, In stands for a residue of a cationic polymerization initiator, NP stands for a residue of a nucleophilic agent, and m and n are integers of 5 - 10,000 independently of each other, m + n being an integer of 10 - 20,000 and m:n being, in terms of a molar ratio, 1:99 - 99:1, wherein the cloud point of a 1 wt. % aqueous solution of the copolymer is controlled to a value within a range of 37 deg.C - 67 deg.C, and the degree of dispersion (Mw/Mn) is not more than 1.15.
[claim2]
2. The random copolymer according to Claim 1, in which m + n is an integer of 10 - 200, and m:n in terms of a molar ratio is 10:90 - 90:10.
[claim3]
3. The random copolymer according to Claim 1, in which the residue of the cationic polymerization initiator is a substituted or unsubstituted straight chain or branched C 1-20 alkyl, and the residue of the nucleophilic agent is selected from the group consisting of -OH, -SH, -NH 2, -CN, -COOH, -OCOC(CH 3) = CH 2, -OCOCH = CH 2 and -OCH 2CH = CH 2.
[claim4]
4. The random copolymer according to Claim 3, in which the substituent on the substituted straight chain or branched C 1-20 alkyl is represented by the formula: (see diagramm) or the formula:

R **3C ≡ C-,

wherein R **1 and R **2 either stand for C 1-10 alkoxy, aryloxy or aryl-C 1-3 alkyloxy, independently of each other, or R **1 and R **2 together stand for optionally C 1-5 alkyl-substituted ethylenedioxy (-O-CH(R')-CH 2-O-, R' being hydrogen or C 1-5 alkyl) or oxy (=0) group, and
R **3 stands for hydrogen or C 1-5 alkyl.
[claim5]
5. A production method of a random copolymer represented by the formula (A): (see diagramm) in the formula, In stands for a residue of a cationic polymerization initiator, NP stands for a residue of a nucleophilic agent, and m and n are integers of 5 - 10,000 independently of each other, m + n being an integer of 10 - 20,000 and m:n being, in terms of a molar ratio, 1:99 - 99:1, wherein the cloud point of a 1 wt.% aqueous solution of the copolymer is controlled to a value within a range of 37 deg.C - 67 deg.C, and the degree of dispersion (Mw/Mn) is not more than 1.15,
which comprises a step of ring-opening polymerizing a monomeric mixture of 2-ethyl-2-oxazoline with 2-isopropyl-2-oxazoline at a molar ratio of 1:99 - 99:1 in an inert solvent at 35 deg.C - 45 deg.C in the presence of a cationic polymerization initiator, a step of reacting the resultant random copolymer with a nucleophilic agent, and, where necessary, a step of isolating the formed polymer.
[claim6]
6. The production method according to Claim 5, in which the cationic polymerization initiator is a substituted or unsubstituted, straight chain or branched C 1-20 alkyl tosylate.
[claim7]
7. The production method according to Claim 6, in which the substituent on the substituted straight chain or branched C 1-20 alkyl is represented by the formula: (see diagramm) or the formula:

R **3C ≡ C-,

wherein R **1 and R **2 either stand for C 1-10 alkoxy, aryloxy or aryl-C 1-3 alkyloxy, independently of each other, or R **1 and R **2 together stand for optionally C 1-5 alkyl-substituted ethylenedioxy (-O-CH(R')-CH 2-O-, R' being hydrogen or C 1-5 alkyl) or oxy (=0) group, and
R **3 stands for hydrogen or C 1-5 alkyl.
  • Applicant
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
  • Inventor
  • KATAOKA KAZUNORI
  • YAMASAKI YUICHI
  • PARK JOON-SIK
IPC(International Patent Classification)
Reference ( R and D project ) CREST Creation of Bio-Devices and Bio-Systems with Chemical and Biological Molecules for Medical Use AREA
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