Method for production of polyesters having free acid function within chain

FIELD: polymers.

SUBSTANCE: invention relates to method for production of polyesters having several free acid functions in the middle of chain and based on cyclic esters such as lactides and glycosides. Disclosed is production of abovementioned polyesters by ring opening polymerization in presence of chain initiator, namely tartaric acid benzyl diester, having optionally substituted phenyl radical; and removing of protective group from carboxylic functions of chain initiator.

EFFECT: improved method for polyester production.

4 cl, 12 ex, 3 tbl

 

Biodegradable polymers have become increasingly popular and are used in a variety of areas and, in particular, in the production of agricultural products and pharmaceuticals. In the pharmaceutical field application of polymers has become common for surgical applications (rassasyvanie joints and brackets) and for the creation of formulations with prolonged release.

The most common of these polymers is obtained polymerization with ring opening of cyclic esters of hydroxy acids, such as glycolide, lactides or L-lactides. These polymerization is carried out with a specified cyclic esters using, typically, the initiation of a hydroxyl group (lactic or glycolic hydroxycitrate) and catalysis such diverse compounds as salts of tin (ethylhexanoate or octoate) (WO 91/16368), metal-based compounds (isopropyl aluminum, derivatives of tin, zinc, etc.) (Macromol. Chem. Phys. C 35, 379 (1995); S. Penczek et al., Macromol. Chem. Phys., 198, 1973 (1997); Xin-De Feng & Yan Jia, Macromol. Symp., 118, 625 (1997); M. Ovitt et al., J. Am. Chem. Soc., 1999, 121, 4072).

The use of such polymers has gained great importance to "lock" the active ingredients and the regulation of sustained release in the body. This mechanism can be used especially for drug substances is high activity and in this series, the peptides comprise a family of choice.

The combination of the peptide to the polymer can be carried out using either mechanical phenomena, such as, for example, coacervation, or using a mechanism of formation of ionic bonds, especially helpful if the peptide contains an amino group, capable of forming salts.

The increase of acid functional groups in the same polymer chain is advantageous to increase the capacity of communication. In fact, the polymer or copolymer with lacheny or glycolide base and derived from alcohol does not contain acid functions in the chain, in order to obtain a polymer with an acid group, requires the presence of acid functions on the polymerization initiator. Therefore, with the aim of increasing the number of carboxylic groups on the same chain as the chain initiators can be used (poly)hydroxy(poly)acid, such as tartaric acid, malic acid and citric acid (US 6111033).

However, the application of the hydroxy acid as an initiator of polymerization sometimes has the disadvantage concerning the reproducibility of the obtained polymer: in fact, compared with the mechanism of polymerization, which is carried out starting from the alcohol function (initiated or generated by opening cycle), this often leads to the phenomenon of interesterification between the obtained polyester chain and the acid is a function of the initiator.

Thus, it is not obvious that the polymer is initiated, for example, tartaric acid, remain free of acid functionality in the middle (approximately) of the polymer chain, as in the interesterification these functions are replaced, and the free acid groups at the end of the chain are considered unsuitable. Moreover, in the case of tartaric acid in the polymerization conditions can cause the degradation of acid: when heated in an acidic environment occurs dehydration of tartaric acid with the formation of water and ketosterol acid, which, in turn, decarboxylated with the formation of pyruvic acid. The resulting water can be opened cyclic ester, resulting in a "nuisance" initiator.

Therefore, the present invention provides a method which makes it possible to obtain polymers with the free acid functions in the chain (i.e. the free acid functions along the chain and approximately in the middle of the chain).

Therefore, the subject of this invention is a method of obtaining polyesters containing several free acid functions, located in the middle of the chain by polymerization with ring opening in the presence of initiator circuit: benzyl diapir tartaric acid, phenyl radical which is optionally someseni is.

In this reaction the medium acidic function (poly)hydroxy(poly)acid secure and stable. The phenyl radical may be substituted by one or more identical or different substituents selected from nitro, alkoxygroup. The protective group is preferably chosen so that it useplease neutral hydrolysis.

A separate object of this invention is the method as defined above, characterized in that the polyester is obtained on the basis of one of the following compounds: L-lactic acid, D-lactic acid, DL-lactic acid, ε-caprolactone, p-dioxanone, ε-Caproic acid, alkylenediamine, cycloalkylation, alkylresorcinols, β-hydroxybutyrate, substituted or unsubstituted trimethylhexanoate, 1,5-dioxan-2-it, 1,4-dioxan-2-it, glycolide, glycolic acid, L-lactide, D-lactide, DL-lactide, mizolastine; and all optically active isomers, racemates or copolymers of the latter.

A particular object of the present invention is also a method, as defined above, characterized in that the polyester is obtained on the basis of one of the following compounds: L-lactic acid, D-lactic acid, DL-lactic acid, ε-caprolactone, p-dioxanone, ε-Caproic acid, substituted or unsubstituted trimethylhexanoate, glycol is Yes, glycolic acid, L-lactide, D-lactide, DL-lactide, meso-lactide; and all optically active isomers, racemates or copolymers of the latter. Preferably complex polyester is obtained on the basis of one of the following compounds: L-lactic acid, D-lactic acid, DL-lactic acid, glycolide, glycolic acid, L-lactide, D-lactide, DL-lactide, mizolastine; and all optically active isomers, racemates or copolymers of the latter.

Therefore, the method of obtaining, in accordance with this invention includes the following stages:

- getting complicated polyester polymerization with ring opening in the presence of initiator circuit: benzyl complex fluids tartaric acid; a method of polymerization with ring opening implement in accordance with the methods known to the person skilled in the art (J. Am. Chem. Soc., 2000, 122, 1552; Polymer International, 45 (1998) 60).

- remove the protection with carboxyl functions: it is obvious that the acid functional group of the (poly)hydroxy(poly)acid protecting groups can be removed by the mechanism, making it possible to save other ester functional groups in the polymer chain intact. Thus, after removing the protective groups can be obtained a polymer having free acid functional groups within the chain.

The reaction of removing the protective groups before the hat is one of the standard ways of removing the protective groups, well-known specialist in this field. In the case of benzyl complex of diapir tartaric acid, removing the protective group can be carried out in accordance with well known methods dibenzylamine, such as catalytic hydrogenation, carried out with hydrogen, or by way of transfer of hydrogen, preserving the integrity of the polymer.

If necessary, the thus obtained complex polyester can be purified according to standard purification methods known to the expert in this field.

According to a very preferred subject of the invention is the method described above, characterized in that the initiator of the chain is benzyl complex fluids tartaric acid.

Unless otherwise noted, all technical and scientific terms used in this application have the same meaning, which is usually understood by a person skilled in the field that belongs to this invention. Similarly, all publications, patent applications and all other references mentioned in this application are included as references.

To illustrate the above techniques are presented the following examples, which in no case should not be construed as limiting the scope of the invention.

EXPERIMENTAL PART

Getting copolymer 73/27 L-lactide with what licoeldom

Stage 1: Polymerization

Before loading into the reactor, purged with nitrogen, an inert atmosphere is weighed mLg L-lactide, mGg glycolide and benzoyltartaric (DBT) and then homogenized using the turbula (approximately 5 minutes). Add 1.3 ml of catalyst polymerization: ethylhexanoate Sn (II) (0,2 M in toluene) and the reactor vacuum (P<3 mbar) for 30 min at 50°C. the mixture is Then maintained at a temperature of approximately 100°C for 30 minutes, then the temperature was raised to In (°). Mixing at 25 rpm carried out during the period (hours). The obtained polymer PLGT(benzyl) is cleaned by placing in a vacuum (P<3 mbar) at 130°C for 30 minutes, and then granularit at a temperature of approximately 100°C.

The results are presented below in Table 1.

Stage 2: Removal of the protective group

135 mg of the polymer obtained in stage 1, are dissolved in 700 ml of acetone under stirring on a magnetic stirrer at ambient temperature for about one hour. The resulting solution was placed in a hydrogenerator, then add the catalyst for hydrogenation (17 g 10% Pd/C (relative humidity 50%)). The reactor vacuum at ambient temperature, then the vacuum is interrupted by nitrogen. Conduct three cycles of compression/decompression of hydrogen (P=8 bar). The mixture stand, stirring at 50°Since when is eating regulate pressure at 8 bar for 3 hours. To determine the residual level of protective groups hold control using NMR. When the residual level is below 0.1%, the suspension is filtered through a layer of filtration agent (tkernel, cellulose and so on).

Step 3: Clean

The obtained complex polyester purified by treatment with a solvent.

The results obtained are presented in Table. 2.

DBT 1,60% i.e. of 6.90 g
Table 1
ExampleDownload (g)(1)The initiator % (mol)(2)In (°)C (h)
1400tartaric acid and 1.00%, i.e. of 4.45 g2002
2175DBT 2,00% i.e. 8,632002
3175DBT to 3.00% i.e 12,90 g2002
4175DBT of 1.75% i.e 7.50 g2002
5400DBT 1,40% i.e. 13,80 g2000,75
6400DBT 1,40% i.e. 13,80 g2003
7175DBT 1,40% i.e. 6,00 g1603
81751403
9175DBT 1,45% i.e. 6.25 g1253,25
101000DBT 1,45% i.e. 35,6 g1253,25
111000DBT 2,3% i.e. 56,9 g1253,5
121000DBT 2,8% i.e. to 69.6 g1253,5
(1)to download 175 g: mL=135,6 g and mG=39,4 g; for a load of 400 g: mL=310 g and mG=90 g; to load 1000 g: mL=775 g and mG=225,

(2)the percentage in relation to the monomers

Table 2
ExampleMwTartaric acid (molar %)(3)Ester of tartaric acid (molar %)(4)
138700<0,10,15
2165000,60,15
3120000,850,34
4155000,30,05
5205000,50,10
616000 0,10,05

7230000,850,10
8158000,610,07
9213000,670,00
10251000,700,00
11168001,100,00
12133331,400,00
(3)the content of free tartaric acid

(4)the content of tartaric acid in which at least one functional group preterition.

Using as an initiator benzyl complex fluids tartaric acid (DBT), the authors observed an acceleration of the phenomenon of polymerization: polymerization process initiated by the tartaric acid, the reaction actually starts after a certain period of heating, which can last up to 30 minutes at temperatures above 160-180°and during this period may occur above the phenomenon of degradation. When using benzyl complex diapir tartaric acid reaction begins immediately at a temperature below or equal to 125°C and virtually zavershaetsa within 210 minutes.

This phenomenon definitely is an advantage in order to avoid thermal degradation will likely occur during continued heating. It should be noted that prolonged heating at high temperatures (160-180° (C) causes the phenomenon of interesterification, including the initiator, such as DBT, as shown in Table 3 for download 1000

Table 3
ExampleThe initiator % (mol)In (aboutC)C (h)MwTartaric acidEster of tartaric acid
101,45% i.e. 35,6 g1253,255251000,700,00
10a1,45% i.e. 35,6 g2001260000,570,10
10b1,45% i.e. 35,6 g2002228000,420,14
10c1,45% i.e. 35,6 g2003216000,310,13
11 2,3% i.e. 56,9 g1253,5168001,100,00
11a2,3% i.e. 56,9 g160118300//
11b2,3% i.e. 56,9 g1801180000,90,12
11c2,3% i.e. 56,9 g2001185000,670,18

1. The method of obtaining polyesters containing several features of the free acid at the location of the acids in the middle of the chain, based on one of the following compounds: L-lactic acid, D-lactic acid, DL-lactic acid, glycolide, glycolic acid, L-lactide, D-lactide, DL-lactide, mesolectal and all optically active isomers, racemates or copolymers of the latter, by polymerization with ring opening in the presence of initiator, chain - benzyl complex diapir tartaric acid, phenyl radical which is optionally substituted, and removal of the protective group of carboxyl functions of the initiator of the chain.

2. The method according to claim 1, characterized in that the complex polyester based on one of the following compounds: L-lactic acid, D-lactic acid, glycolide, L-lactide, D-lactide, mesolectal and all optically active isomer is, the racemates or copolymers of the latter.

3. The method according to claim 1, characterized in that the complex polyester based on one of the following compounds: DL-lactic acid, glycolic acid, DL-lactide and all optically active isomers, racemates or copolymers of the latter.

4. The method according to one of the preceding paragraphs, characterized in that the initiator circuit is benzyl complex fluids tartaric acid.



 

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FIELD: chemical industry; methods of production of polyester.

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4 cl, 12 ex, 3 tbl

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FIELD: chemical industry; methods of production of polyester.

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22 cl, 1 tbl, 24 ex

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SUBSTANCE: invention relates to method for production of polyesters having several free acid functions in the middle of chain and based on cyclic esters such as lactides and glycosides. Disclosed is production of abovementioned polyesters by ring opening polymerization in presence of chain initiator, namely tartaric acid benzyl diester, having optionally substituted phenyl radical; and removing of protective group from carboxylic functions of chain initiator.

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4 cl, 12 ex, 3 tbl

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