Method for producing polyester, and fluorine-containing dicarboxylic acid ester compound
View Patent ↗The present invention relates to a method for producing a polyester, containing conducting a transesterification reaction of at least one compound selected from compounds represented by the following formulae (1) to (3) with a diol compound in the presence of a catalyst: wherein Ar is a divalent aromatic hydrocarbon group or the like; R 1 is CX 1 Y 1 R 4 ; R 2 is a hydrogen atom or CX 2 Y 2 R 5 ; R 3 is a hydrogen atom or CX 3 Y 3 R 6 ; R 7 is a perfluoroalkylene group having 1 to 5 carbon atoms; X 1 to X 3 are a hydrogen atom, a fluorine atom or R f ; Y 1 to Y 3 are a fluorine atom or R f ; R 4 to R 6 are a fluorine atom, R f , OR f or the like; and R f is a fluoroalkyl group having 1 to 4 carbon atoms.
1. A method for producing a polyester, comprising conducting a transesterification reaction of at least one compound selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (2) and a compound represented by the following formula (3) with a diol compound in the presence of a catalyst:
wherein Ar is a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group,
R 1 is a group represented by CX 1 Y 1 R 4 , and two R 1 s may be the same or different from each other,
R 2 is a hydrogen atom or a group represented by CX 2 Y 2 R 5 , and two R 2 s may be the same or different from each other,
R 3 is a hydrogen atom or a group represented by CX 3 Y 3 R 6 , and two R 3 s may be the same or different from each other,
X 1 to X 3 are each independently a hydrogen atom, a fluorine atom or R f ,
Y 1 to Y 3 are each independently a fluorine atom or R f ,
R 4 to R 6 are each independently a fluorine atom, R f , OR f or an alkyl group having 1 to 6 carbon atoms, and
R f is independently a fluoroalkyl group (which may contain an etheric oxygen) having 1 to 4 carbon atoms;
wherein Ar is a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group,
R 1 is a group represented by CX 1 Y 1 R 4 ,
R 2 is a hydrogen atom or a group represented by CX 2 Y 2 R 5 ,
R 3 is a hydrogen atom or a group represented by CX 3 Y 3 R 6 ,
R 7 is a perfluoroalkylene group (which may contain an etheric oxygen) having 1 to 5 carbon atoms,
X 1 to X 3 are each independently a hydrogen atom, a fluorine atom or R f ,
Y 1 to Y 3 are each independently a fluorine atom or R f ,
R 4 to R 6 are each independently a fluorine atom, R f , OR f or an alkyl group having 1 to 6 carbon atoms, and
R f is independently a fluoroalkyl group (which may contain an etheric oxygen) having 1 to 4 carbon atoms; and
wherein Ar is a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, and
R 7 is a perfluoroalkylene group (which may contain an etheric oxygen) having 1 to 5 carbon atoms, and two R 7 s may be the same or different from each other.
2. The method for producing a polyester according to claim 1 , wherein the compound represented by the above formula (1) to (3) is obtained by a reaction using as a starting material at least one fluorine-containing alcohol selected from the group consisting of a compound represented by the following formula (5) and a compound represented by the following formula (6):
wherein R 1 is a group represented by CX 1 Y 1 R 4 ,
R 2 is a hydrogen atom or a group represented by CX 2 Y 2 R 5 ,
R 3 is a hydrogen atom or a group represented by CX 3 Y 3 R 6 ,
R 7 is a perfluoroalkylene group (which may contain an etheric oxygen) having 1 to 5 carbon atoms,
X 1 to X 3 are each independently a hydrogen atom, a fluorine atom or R f ,
Y 1 to Y 3 are each independently a fluorine atom or R f ,
R 4 to R 6 are each independently a fluorine atom, R f , OR f or an alkyl group having 1 to 6 carbon atoms, and
R f is independently a fluoroalkyl group (which may contain an etheric oxygen) having 1 to 4 carbon atoms.
3. The method for producing a polyester according to claim 2 , wherein the fluorine-containing alcohol has 2 to 10 carbon atoms.
4. The method for producing a polyester according to claim 2 , wherein R 2 in formula (5) is a group represented by CX 2 Y 2 R 5 .
5. The method for producing a polyester according to claim 2 , wherein the fluorine-containing alcohol has a pKa of less than 15.
6. The method for producing a polyester according to claim 2 , wherein the fluorine-containing alcohol has a pKa of less than 13.
7. The method for producing a polyester according to claim 2 , wherein the fluorine-containing alcohol is at least one selected from the group consisting of 2,2,2-trifluoroethanol, 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,3-pentafluoro-1-propanol, 1,1,1,3,3,3-hexafluoro-2-propanol, 2-fluoro-1-propanol, 2,2,3,4,4,4-hexafluoro-1-butanol, 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, 2,2,3,3,4,4,5,5-octafluorocyclopentanol, perfluoro(t-butyl) alcohol, and 2,2,3,3,4,4,5,5,6,6-decafluorocyclohexanol.
8. The method for producing a polyester according to claim 1 , wherein the diol compound is an aromatic diol compound.
9. The method for producing a polyester according to claim 1 , wherein the diol compound is bisphenol A.
10. The method for producing a polyester according to claim 1 , wherein the catalyst is an alkali metal salt or an alkali earth metal salt.
11. Bis(2,2,3,3-tetrafluoropropyl)isophthalate represented by the following formula (1-1):