Process for condensing at least one epoxide on at least one cyclic anhydride in the presence of a catalyst consisting of at least one titanium nitrogenous complex
| Title: | Process for condensing at least one epoxide on at least one cyclic anhydride in the presence of a catalyst consisting of at least one titanium nitrogenous complex |
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| Patent Number: | 5,030,711 |
| Publication Date: | July 09, 1991 |
| Appl. No: | 07/492,005 |
| Application Filed: | March 12, 1990 |
| Abstract: | The invention relates to a process for condensing at least one epoxide on at least one cyclic anhydride of a dicarboxylic acid in the presence of a catalyst consisting of at least one titanium nitrogenous complex of the formula (I) Ti(OR.sup.1).sub.m (OR.sup.2 ).sub.n (OR.sup.2 ).sub.p Lg in which R.sup.1, R.sup.2 and R.sup.3 each independently represents one hydrocarbon group, L represents the remainder of a nitrogenous compound, the sum of m+n+p+q is 4, q is an integer from 1 to 4 and m, n and p are independently each 0 or 1. The process allows for obtaining a perfectly alternating polyester. |
| Inventors: | Bagrel, Valerie (Fontenay-aux-Roses, FRX); Garapon, Jacques (Lyon, FRX); Touet, Remi (Saint Egreve, FRX); Huet, Catherine (Chalon Sur Saone, FRX); Damin, Bernard (Oullins, FRX) |
| Assignees: | Institut Francais du Petrole (Rueil Malmaison, FRX), L'Air Liquide Societe Anonyme pour l'Etude et l'Exploitation des Procedes Georges Claude (Paris, FRX), ELF France (Courbevoie, FRX) |
| Claim: | We claim |
| Claim: | 1. A process for condensing at least one epoxide on at least one cyclic anhydride of a dicarboxylic acid in the presence of a catalyst consisting essentially of at least one titanium nitrogenous complex of the following general formula: [equation included] |
| Claim: | in which |
| Claim: | m, n and p represent each, independantly from one another, a number equal to 0 or 1, q represents an integer from 1 to 4 and in all cases the sum m+n+p+q is 4; |
| Claim: | R.sup.1, R.sup.2 and R.sup.3 represent each, independantly from one another, a hydrocarbon group with 1 to 30 atoms of carbon, substituted or not by at least one hetero-atom or by at least one hetero-atomic group |
| Claim: | the L group or groups represent each, independantly from one another, the remainder of a nitrogenous compound. |
| Claim: | 2. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which R.sup.1, R.sup.2 and R.sup.3 represent each, independently from one another, an alkyl or alkenyl group, linear or branched. |
| Claim: | 3. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which R.sup.1, R.sup.2 and R.sup.3, identical, represent each a linear or branched alkyl group. |
| Claim: | 4. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which the L group or groups represent each, independantly from one another, the remainder of a compound selected from the group consisting of the nitrogenous compounds corresponding to one of the general formulas (II) and (III): ##STR5## in which: --X represents a hydroxyl group or a nitrogenous group of the formula --NHR.sup.10 in which R.sup.10 represents an atom of hydrogen or a hydrocarbon group with 1 to 30 atoms of carbon, substituted or not by at least one hetero-atom or by at least one hetero-atomic group; |
| Claim: | R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 represent each, independantly from one another, an atom of hydrogen or a hydrocarbon group with 1 to 30 atoms of carbon, substituted or not by at least one hetero-atom or by at least one hetero-atomic group, and at least two of these R.sup.4 to R.sup.9 groups can form together with the atoms to which they are bound a saturated or unsaturated aliphatic ring, a benzene ring or a saturated or unsaturated heterocycle; |
| Claim: | t represents an integer from 1 to 3; |
| Claim: | v represents 0 or 1; |
| Claim: | each R.sup.11 group independantly represents an atom of hydrogen, an atom of halogen, a hydrocarbon group with 1 to 30 atoms of carbon, substituted or not by at least one hetero-atom or by at least one hetero-atomic group, and two R.sup.11 groups (when t represents 2 to 3) can form together with the atoms of carbon to which they are bound a hydrocarbon, saturated, unsaturated, aromatic ring or a heterocycle; |
| Claim: | when v=1, --Y represents an atom of carbon, a hydrocarbon group with 1 to 30 atoms of carbon, substituted or not by at least one hetero-atom or by at least one hetero-atomic group, and R.sup.12 can also form together with the atom to which it is bound and with one of the atoms of the R.sup.13 group defined hereafter a hydrocarbon, saturated, unsaturated, a benzene ring or a heterocycle and R.sup.13 represents a divalent hydrocarbon group with 1 to 12 atoms of carbon, substituted or not by at least one hetero-atom or by at least one hetero-atomic group; |
| Claim: | when v=0, --Y represents a hetero-atom, R.sup.13 represents a divalent hydrocarbon group with 1 to 12 atoms of carbon, substituted or not by at least one hetero-atomic group. |
| Claim: | 5. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which each L group or groups represent, independantly from one another, the remainder of a compound of the general formula (II), in which X represents the hydroxyl or the amino group, selected from the following compounds: mono-ethanolamine, di-ethanolamine, tri-ethanolamine, amino-1 propanol-2, di-isopropanolamine, tri-isopropanol-amine, amino-1 butanol-2, di-sec-butanolamine, tri-sec-butanolamine, dimethylamino-2 ethanol, di-ethylethanol-amine, methylamino-2 ethanol, butylethanolamine, dibutyl-ethanolamine, isopropylethanolamine, di-isopropyl-ethanolamine, methyldiethanolamine, ethyldiethanolamine, dimethylamino-1 propanol-2, amino-2 methyl-2 propanol-1, dimethylamino-2 methyl-2 propanol-1 and trimethyl-ethylenediamine. |
| Claim: | 6. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which the L group or groups represent each, independantly from one another, the remainder of a compound of general formula (III) selected from the following compounds: hydroxy-8 quinoline, hydroxy-7 indole, hydroxy-5 or -8 quinoxaline, hydroxy-8 quinazoline, hydroxy-8 cinnoline, hydroxy-4 or -5 acridine, hydroxy-1, -4, -6 or -9 phenazine and the derivatives of these compounds substituted by at least one R.sup.11 group such as defined above in claim 4. |
| Claim: | 7. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which m=n=1, p=0, q=2 and R.sup.1 and R.sup.2, identical, represent each a lower alkyl group, linear or branched, with 1 to 4 atoms of carbon. |
| Claim: | 8. A process according to claim 1 wherein said titanium nitrogenous complex corresponds to the general formula (I) in which m=n=p=q=1, and R.sup.1, R.sup.2 and R.sup.3, identical, represent each a lower alkyl group, linear or branched, with 1 to 4 atoms of carbon. |
| Claim: | 9. A process according to claim 1 for condensing at least one epoxide on at least one cyclic anhydride of a saturated or unsaturated vicinal dicarboxylic acid. |
| Claim: | 10. A process according to claim 1 wherein the cyclic anhydride is selected from the group consisting of maleic anhydride, citraconic anhydride, the halogenomaleic anhydrides, succinic anhydride, the alkenylsuccinic or poly-alkenylsuccinic anhydrides, phthalic anhydride, the phthalic anhydrides substituted by at least one atom of halogen and/or at least one alkyl group, trimellitic anhydride, cyclohexanedicarboxylic-1,2 anhydride, the cyclohexanedicarboxylic-1,2 anhydrides substituted by at least one atom of halogen and/or at least one alkyl group, nadic anhydride, the nadic anhydrides substituted by at least one atom of halogen and/or at least one alkyl group, glutaric anhydride, the glutaric anhydrides substituted by at least one atom of halogen and/or at least one alkyl group, glutaconic anhydride and the glutaconic anhydrides substituted by at least one atom of halogen and/or at least one alkyl group. |
| Claim: | 11. A process according to claim 1 for condensing on at least one cyclic anhydride of a dicarboxylic acid at least one epoxide corresponding to the following general formula: ##STR6## in which R.sup.1 and R.sup.3, identical or different, represent each an atom of hydrogen or a lower alkyl group with 1 to 4 atoms of carbon, R.sup.2 and R.sup.4, identical or different, represent each an atom of hydrogen, a hydrocarbon group, substituted or not by at least one atom of halogen, with 1 to 30 atoms of carbon, a group of formula R.sup.5 -O-R.sup.6 - in which R.sup.5 represents a hydrocarbon group, substituted or not by at least one atom of halogen, with 1 to 30 atoms of carbon and R.sup.6 represents a divalent hydrocarbon group with 1 to 30 atoms of carbon, while R.sup.2 can also represent a group of formula ##STR7## or a group of formula ##STR8## in which R.sup.5 and R.sup.6 have the definition given above, R.sup.2 and R.sup.4 can also form together with the atoms of carbon to which they are bound a saturated or unsaturated ring with 4 to 30 atoms of carbon. |
| Claim: | 12. A process according to claim 4, wherein said titanium nitrogenous complex corresponds to the general formula (I) in which R.sup.1, R.sup.2 and R.sup.3 represent each, independently from one another, an alkyl or alkenyl group, linear or branched. |
| Claim: | 13. A process according to claim 4, wherein said titanium nitrogenous complex corresponds to the general form (I) in which R.sup.1, R.sup.2 and R.sup.3, identical, represent each a linear or branched alkyl group. |
| Claim: | 14. A process according to claim 5, wherein said titanium nitrogenous complex corresponds to the general formula (I) in which R.sup.1, R.sup.2 and R.sup.3 represent each, independently from one another, an alkyl or alkenyl group, linear or branched. |
| Claim: | 15. A process according to claim 5, wherein said titanium nitrogenous complex corresponds to the general form (I) in which R.sup.1, R.sup.2 and R.sup.3, identical, represent each a linear or branched alkyl group. |
| Claim: | 16. A process according to claim 6, wherein said titanium nitrogenous complex corresponds to the general formula (I) in which R.sup.1, R.sup.2 and R.sup.3 represent each, independently from one another, an alkyl or alkenyl group, linear or branched. |
| Claim: | 17. A process according to claim 6, wherein said titanium nitrogenous complex corresponds to the general form (I) in which R.sup.1, R.sup.2 and R.sup.3, identical, represent each a linear or branched alkyl group. |
| Claim: | 18. A process according to claim 6, wherein said titanium nitrogenous complex corresponds to the general formula (I) in which m=n=1, p=0, q=2 and R.sup.1 and R.sup.2, identical, represent each a lower alkyl group, linear or branched, with 1 to 4 atoms of carbon. |
| Claim: | 19. A process according to claim 6, wherein said titanium nitrogenous complex corresponds to the general formula (I) in which m=n=p=q=1, and R.sup.1, R.sup.2 and R.sup.3, identical, represent each a lower alkyl group, linear or branched, with 1 to 4 atoms of carbon. |
| Current U.S. Class: | 528/361; 528/92; 528/365; 528/366 |
| Current International Class: | C08G 6342 |
| Patent References Cited: | 2742448 April 1956 Beacham et al. 2809184 October 1957 Langer 3320193 May 1967 Beck et al. 4117361 September 1978 Smith et al. 4973613 November 1990 Paar |
| Primary Examiner: | Nielsen, Earl |
| Attorney, Agent or Firm: | Millen, White & Zelano |
| Accession Number: | edspgr.05030711 |
| Database: | USPTO Patent Grants |
| Language: | English |
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