US2012016101A1PendingUtilityA1

Polylactide resin and preparation method thereof

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Assignee: YOON SUNG-CHEOLPriority: Feb 9, 2009Filed: Feb 9, 2010Published: Jan 19, 2012
Est. expiryFeb 9, 2029(~2.6 yrs left)· nominal 20-yr term from priority
Inventors:Sung-Cheol YoonIn Su LeeSeong-Woo KimSeung Young Park
B01J 2531/42B01J 2531/0219B01J 31/122B01J 31/1805C08G 63/85Y02P20/52B01J 2531/26C08G 63/823
47
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Claims

Abstract

The present invention is directed to an organometallic complex and a catalyst composition capable of producing polylactide resins with improved properties at a higher conversion rate, a method of producing the organometallic complex, polylactide resins having enhanced hydrolysis resistance and heat resistance together with superior mechanical properties, a preparation process therefor, and polylactide resin compositions including the same.

Claims

exact text as granted — not AI-modified
1 . An organometallic complex of Chemical Formula 1: 
       
         
           
           
               
               
           
         
         wherein n is an integer of 0 to 15, p is an integer of 0 to 2, a is 0 or 1, M is Sn or Zn, R 1  and R 3  are the same as or different from each other, and each of them is hydrogen, a substituted or unsubstituted C3 to C10 alkyl, a substituted or unsubstituted C3 to C10 cycloalkyl, or a substituted or unsubstituted C6 to C10 aryl, R 2  is a substituted or unsubstituted C3 to C10 alkylene, a substituted or unsubstituted C3 to C10 cycloalkylene, or a substituted or unsubstituted C6 to C10 arylene, and each of X and Y is independently an alkoxy group or a carboxyl group. 
       
     
     
         2 . The organometallic complex according to  claim 1 , wherein each of R 1  and R 3  is a monovalent phenyl group substituted with a C1 to C10 alkyl group, or a C3 to C10 alkyl group or cycloalkyl group, R 2  is a divalent phenylene group substituted with a C1 to C10 alkyl group, or a C3 to C10 alkylene group or cycloalkylene group. 
     
     
         3 . The organometallic complex according to  claim 1 , wherein the MX p Y 2-p  is tin(II) 2-ethylhexanoate (Sn(Oct) 2 ). 
     
     
         4 . A method of producing a organometallic complex of  claim 1 , which comprises a step of subjecting a compound of Chemical Formula 2 and a compound of Chemical Formula 3 to a reaction: 
       
         
           
           
               
               
           
         
         wherein n is an integer of 0 to 15, p is an integer of 0 to 2, M is Sn or Zn, R 1  and R 3  are the same as or different from each other, and each of them is hydrogen, a substituted or unsubstituted C3 to C10 alkyl, a substituted or unsubstituted C3 to C10 cycloalkyl, or a substituted or unsubstituted C6 to C10 aryl, R 2  is a substituted or unsubstituted C3 to C10 alkylene, a substituted or unsubstituted C3 to C10 cycloalkylene, or a substituted or unsubstituted C6 to C10 arylene, and each of X and Y is independently an alkoxy group or a carboxyl group. 
       
     
     
         5 . A catalyst composition comprising a compound of Chemical Formula 2 and a compound of Chemical Formula 3: 
       
         
           
           
               
               
           
         
         wherein n is an integer of 0 to 15, p is an integer of 0 to 2, M is Sn or Zn, R 1  and R 3  are the same as or different from each other, and each of them is hydrogen, a substituted or unsubstituted C3 to C10 alkyl, a substituted or unsubstituted C3 to C10 cycloalkyl, or a substituted or unsubstituted C6 to C10 aryl, R 2  is a substituted or unsubstituted C3 to C10 alkylene, a substituted or unsubstituted C3 to C10 cycloalkylene, or a substituted or unsubstituted C6 to C10 arylene, and each of X and Y is independently an alkoxy group or a carboxyl group. 
       
     
     
         6 . The catalyst composition according to  claim 5 , wherein each of R 1  and R 3  is a monovalent phenyl group substituted with a C1 to C10 alkyl group, or a C3 to C10 alkyl group or cycloalkyl group, and R 2  is a divalent phenylene group substituted with a C1 to C10 alkyl group, or a C3 to C10 alkylene group or cycloalkylene group. 
     
     
         7 . The catalyst composition according to  claim 5 , wherein the compound of Chemical Formula 3 is tin(II) 2-ethylhexanoate (Sn(Oct) 2 ). 
     
     
         8 . A polylactide resin which has an acidity of 10 meq/kg or less and a weight average molecular weight of 100,000 to 1,000,000. 
     
     
         9 . The polylactide resin according to  claim 8 , which has acidity of 3 to 10 meq/kg and a weight average molecular weight of 200,000 to 1,000,000. 
     
     
         10 . The polylactide resin according to  claim 8 , which comprises a catalyst residue including an organometallic complex of Chemical Formula 1 or a compound of Chemical Formula 2 and a compound of Chemical Formula 3: 
       
         
           
           
               
               
           
         
         wherein n is an integer of 0 to 15, p is an integer of 0 to 2, a is 0 or 1, M is Sn or Zn, R 1  and R 3  are the same as or different from each other, and each of them is hydrogen, a substituted or unsubstituted C3 to C10 alkyl, a substituted or unsubstituted C3 to C10 cycloalkyl, or a substituted or unsubstituted C6 to C10 aryl, R 2  is a substituted or unsubstituted C3 to C10 alkylene, a substituted or unsubstituted C3 to C10 cycloalkylene, or a substituted or unsubstituted C6 to C10 arylene, and each of X and Y is independently an alkoxy group or a carboxyl group. 
       
     
     
         11 . The polylactide resin according to  claim 10 , wherein the amount of the catalyst residue is no more than 15 ppm. 
     
     
         12 . The polylactide resin according to  claim 8 , which shows a weight loss of less than 20 wt % when heated from room temperature to 300° C. during thermal gravimetric analysis (TGA). 
     
     
         13 . A process for preparing a polylactide resin, which comprises a step of subjecting lactide monomers to ring opening polymerization in the presence of an organometallic complex of  claim 1 . 
     
     
         14 . A process for preparing a polylactide resin, which comprises a step of subjecting lactide monomers to ring opening polymerization in the presence of a catalyst composition of  claim 5 . 
     
     
         15 . The process for preparing a polylactide resin according to  claim 13  or  claim 14 , wherein the MX p Y 2-p  is tin(II) 2-ethylhexanoate (Sn(Oct) 2 ). 
     
     
         16 . The process for preparing a polylactide resin according to  claim 13  or  claim 14 , wherein R 1  is a monovalent phenyl group substituted with a C1 to C10 alkyl group or a C3 to C10 alkyl group or cycloalkyl group, and R 2  is a divalent phenylene group substituted with a C1 to C10 alkyl group, or a C3 to C10 alkylene group or cycloalkylene group. 
     
     
         17 . The process for preparing a polylactide resin according to  claim 13 , wherein the organometallic complex is prepared by a method comprising a step of subjecting a compound of Chemical Formula 2 and a compound of Chemical Formula 3 to a reaction: 
       
         
           
           
               
               
           
         
         wherein n is an integer of 0 to 15, p is an integer of 0 to 2, M is Sn or Zn, R 1  and R 3  are the same as or different from each other, and each of them is hydrogen, a substituted or unsubstituted C3 to C10 alkyl, a substituted or unsubstituted C3 to C10 cycloalkyl, or a substituted or unsubstituted C6 to C10 aryl, R 2  is a substituted or unsubstituted C3 to C10 alkylene, a substituted or unsubstituted C3 to C10 cycloalkylene, or a substituted or unsubstituted C6 to C10 arylene, and each of X and Y is independently an alkoxy group or a carboxyl group. 
       
     
     
         18 . The process for preparing a polylactide resin according to  claim 13 , wherein the organometallic complex is added at a ratio of 0.001 to 0.1 moles with respect to 100 moles of the lactide monomers. 
     
     
         19 . The process for preparing a polylactide resin according to  claim 14 , wherein the compounds of Chemical Formula 2 and Chemical Formula 3 are added at a ratio of 0.001 to 0.1 moles with respect to 100 moles of the lactide monomers, respectively. 
     
     
         20 . The process for preparing a polylactide resin according to  claim 13  or  claim 14 , wherein the ring opening polymerization is carried out in the presence of an initiator comprising a compound with a hydroxy group. 
     
     
         21 . The process for preparing a polylactide resin according to claim  20 , wherein the compound with a hydroxy group has 8 or more carbon atoms. 
     
     
         22 . The process for preparing a polylactide resin according to  claim 20 , wherein the initiator is added at a ratio of 0.001 to 1 mole with respect to 100 moles of the lactide monomers. 
     
     
         23 . The process for preparing a polylactide resin according to  claim 13  or  claim 14 , wherein the ring opening polymerization is carried out in a manner of a bulk polymerization. 
     
     
         24 . The process for preparing a polylactide resin according to  claim 13  or  claim 14 , wherein the ring opening polymerization is carried out at a temperature of 120 to 200° C. for 0.5 to 8 hours. 
     
     
         25 . A polylactide resin composition comprising a polylactide resin of  claim 8 .

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