Process for the production of a polyester having a reduced crystallization temperature

Patent metadata

Field	Value
Publication number	US-2025051514-A1
Application number	US-202218717544-A
Country	US
Kind code	A1
Filing date	Dec 6, 2022
Priority date	Dec 10, 2021
Publication date	Feb 13, 2025
Grant date	—

Abstract

The present invention relates to a process for the production of a polyester, comprising:a) a stage of esterification of a mixture comprising a monomer A of formula 1 and a monomer B of formula 2 or a monomer A of formula 1, a monomer B of formula 2 and isophthalic acid,in which R1 is chosen from the group consisting of:—(CH2)n—, with n an integer of between 2 and 4,—(CH2—CHR2)—, with R2 chosen from linear or branched alkyl groups comprising between 1 and 6 carbon atoms (C1-C6) and a phenyl group, thenb) a stage of polycondensation.

First claim

1 . A process for the production of a polyester, comprising:
a) a stage of esterification of a mixture comprising a monomer A of formula 1 and a monomer B of formula 2 or a monomer A of formula 1, a monomer B of formula 2 and isophthalic acid, in order to obtain an oligomeric intermediate,

in which R 1 is chosen from the group consisting of:
—(CH 2 ) n —, with n an integer of between 2 and 4,
—(CH 2 —CHR 2 )—, with R 2 chosen from linear or branched alkyl groups comprising between 1 and 6 carbon atoms (C 1 -C 6 ) and a phenyl group, and

b) a stage of polycondensation of the oligomeric intermediate.

2 . The process according to claim 1 , in which the mixture of stage a) comprises the monomer A and the monomer B or the monomer A, the monomer B and isophthalic acid in a molar ratio (meta/[meta+para]) of the meta units, with respect to the combined aromatic units present in the mixture, of between 0.1 mol % and 10.0 mol %.

3 . The process according to claim 1 , in which R 1 is an ethylene group.

4 . The process according to claim 1 , in which the mixture of stage a) comprises a monomer C of formula 3:

in which:
R 3 is chosen from the group consisting of:
the R 1 group,
a —(CH 2 ) n —(O—(CH 2 ) n ) m — group, with m and n integers, m being of between 1 and 4, preferably equal to 1 or 2, and n being of between 2 and 4, preferably equal to 2,
a —(CH 2 —CH(CH 3 ) 2 —CH 2 )— group, and
a —CH 2 —C 6 H 10 —CH 2 — group,

R 4 is chosen from the group consisting of:
a —(CH 2 ) n —(O—(CH 2 ) n ) m — group, with m and n integers, m being of between 1 and 4, preferably equal to 1 or 2, and n being of between 2 and 4, preferably equal to 2,
a —(CH 2 —CH(CH 3 ) 2 —CH 2 )— group, and
a —CH 2 —C 6 H 10 —CH 2 — group.

5 . The process according to claim 4 , in which the mixture of stage a) comprises the monomer C present in a molar ratio of the monomer C, with respect to the combined monomers A and C present in the mixture of stage a), of between 0.05 mol % and 10.00 mol %.

6 . The process according to claim 1 , in which the mixture of stage a) comprises a dicarboxylic acid other than isophthalic acid, such as terephthalic acid, or one of its dialkyl diesters, such as its dimethyl diester, for example dimethyl terephthalate, and/or at least one diol, preferably chosen from ethylene glycol, diethylene glycol, butylene glycol, cyclohexanedimethanol, neopentyl glycol or their mixtures, the preferred diol being ethylene glycol.

7 . The process according to claim 1 , in which stage a) is carried out at a temperature of between 15° and 350° C.

8 . The process according to claim 1 , in which stage a) is carried out at a pressure between 0.05 and 1.0 MPa.

9 . The process according to claim 1 , in which stage b) comprises one or more polycondensation sub-stage(s), for example at least one sub-stage of liquid-phase or melt-phase polycondensation, optionally followed by at least one sub-stage of solid-phase polycondensation.

10 . The process according to claim 1 , in which stage b) implements at least one polymerization section, operated in the liquid or melt phase, at a temperature greater than the temperature at which stage a) is carried out, preferably at a temperature of between 19° and 400° C., preferentially between 22° and 350° C., in a preferred way between 265 and 300° C., and preferably at a pressure between 0.01 and 100.00 kPa, preferably between 0.05 and 10.00 kPa.

11 . The process according to claim 1 , in which stage b) is carried out in the presence of a polymerization catalyst, preferably based on antimony, titanium, germanium, aluminum, zinc acetate, calcium acetate and/or manganese acetate.

12 . The process according to claim 1 , in which the mixture of stage a) comprises the monomer A and the monomer B or the monomer A, the monomer B and isophthalic acid in a molar ratio (meta/[meta+para]) of the meta units, with respect to the combined aromatic units present in the mixture, of between 0.25 mol % and 7.0 mol %.

13 . Process according to claim 1 , in which the mixture of stage a) comprises the monomer A and the monomer B or the monomer A, the monomer B and isophthalic acid in a molar ratio (meta/[meta+para]) of the meta units, with respect to the combined aromatic units present in the mixture, of between 0.5 mol % and 5.0 mol %.

14 . The process according to claim 4 , in which the mixture of stage a) comprises the monomer C present in a molar ratio of the monomer C, with respect to the combined monomers A and C present in the mixture of stage a), of between 0.10 mol % and 10.00 mol %.

15 . The process according to claim 4 , in which the mixture of stage a) comprises the monomer C present in a molar ratio of the monomer C, with respect to the combined monomers A and C present in the mixture of stage a), of between 0.25 mol % and 7.00 mol %.

16 . The process according to claim 4 , in which the mixture of stage a) comprises the monomer C present in a molar ratio of the monomer C, with respect to the combined monomers A and C present in the mixture of stage a), of between 0.50 mol % and 5.00 mol %.

17 . The process according to claim 1 , in which stage a) is carried out at a temperature of between 20° and 300° C.

18 . The process according to claim 1 , in which stage a) is carried out at a temperature of between 25° and 285° C.

19 . The process according to claim 1 , in which stage a) is carried out at a pressure between 0.1 and 0.5 MPa.

Assignees

• Ifp Energies Now
• Jeplan Inc

Inventors

• Blancke Guillaume
• Chiche David
• Favre Frederic
• Leinekugel Le Cocq Damien
• Mekki-Berrada Adrien

Classifications

• C08G63/85

  Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• C08G63/6856

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G63/183

  Terephthalic acids · CPC title

• C08G63/672 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C08G63/181

  Acids containing aromatic rings · CPC title