Process for the preparation of a polyesteramide

Details Process for the preparation of a polyesteramide Process for the preparation of a polyesteramide

2001-01-30

2002-06-25

Boykin, Terressa (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From carboxylic acid or derivative thereof

Reexamination Certificate

active

06410681

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to the process for preparation of a polyesteramide. More specifically the process relates to the preparation of a polyesteramide by contacting carbon monoxide, an aromatic dihalide and a suitable aminohydroxy compound in presence of a catalyst and a base.
BACKGROUND OF THE INVENTION
Polyesteramides are characterized by presence of amide as well as ester functionality in the polymer backbone and therefore are hybrid structures of polyamides and polyesters. These polymers have attracted strong industrial interest because of their excellent heat resistant properties. Various methods have been described in the prior art for the preparation of polyesteramides. These methods generally involve polycondesation reactions of di-acid or a suitable derivative thereof with an aminohydroxy compound.
U.S. Pat. No. 4855397 discloses the preparation of polyesteramide with lower gas permeability by reacting an amino alcohol and a dicarboxylic acid at elevated temperature. U.S. Pat. No. 4,237,251 discloses a two step process for the preparation of polyesteramides in which the first step is condensation of an aromatic monoalkyl dicarboxylates with an aromatic diisocynate to produce aromatic dialkyl diamidedicarboxylate, which in the second step is condensed with a polyhydroxy compound. U.S. Pat. No. 5,185,424 provides a method for polyesteramide preparation by condensation of aminophenol and hydroquinone derivative with aromatic dicarboxylic acids. U.S. Pat. No. 4,839,441 discloses the condensation of dicarboxylate-capped polyamide with a diol to prepare polyesteramide.
Conventional processes for the preparation of polyesteramides suffer from many drawbacks. Firstly, these require the presence of carboxylic group or a suitable derivative thereof in at least one of the monomers and therefore such process is limited to small number of available carboxylic acids. Secondly, conventional processes require use of carboxylic acids or derivatives thereof like acid chloride etc. which are often sensitive to moisture and difficult to handle. Furthermore, the activity of such dicarboxylic acids or their derivatives towards polycondensation has to be high enough to produce sufficiently high molecular weight polymer for any suitable application.
Because of the commercial interest in polyesteramides, increasing academic as well as industrial attention has been paid towards research in developing new methods for their preparation. In view of the advantages and features of the present invention, the process of this invention would be a significant advance in the current state of the art related to the synthesis of polyesteramides.
OBJECTS OF THE INVENTION
The main object of the invention is to provide a catalytic route for the preparation of polyesteramides free of the drawbacks discussed above.
It is another object of the invention to provide a process for the preparation of a polyesteramide that is easy and efficient.
SUMMARY OF THE INVENTION
Accordingly the present invention provides a process for the preparation of an alternating polyesteramide said process comprising reacting an aromatic dihalide of the general formula (I) X1—Ar—X2 wherein Ar is an aromatic or heteroaromatic residue, X1 and X2 are halogens with an aminohydroxy compound of the general formula (II) H
2
N—R—OH wherein R is an alkyl, cycloalkyl, aromatic or heteroaromatic residue; in the presence of carbon monoxide, a catalyst, base and solvent to obtain the desired product.
In one embodiment of the invention, the polyhalide compound is an aromatic compound having at least two halide radicals.
In another embodiment of the invention, each of X1 and X2 are independently selected from the group consisting of I and Br.
In a further embodiment of the invention, suitable aromatic compounds include hydrocarbon aromatics such as benzene, biphenyl, anthracene, naphthalene and the like, nitrogen containing aromatics such as pyridine, bipyridine, phenanthroline and the like; sulfur containing aromatics such as benzothiophene, thiophene and the like and oxygen containing aromatics such as dibenzofuran and the like.
In yet another embodiment of the invention, the halide radical may be present on the same ring or on different rings which may be separated by a variety of bridging units like hydrocarbon, aromatics, heteroatoms and the like as exemplified by aryl sulfone, diaryl ethers, diaryl carbonyls, diaryl sulfides, dialkylbenzenes, dialkoxy benzenes and the like.
In another embodiment of the invention, the process is carried out in the presence of a solvent.
In a further embodiment of the invention, the preferred solvents include chlorobenzene, N-methylpyrollidone, DMAc (N,N-Dimethylacetamide), DMF (N,N-Dimethyl formamide), Dimethylesulfoxide, Toluene and Acetonitrile.
In another embodiment of the invention, the aminohydroxy compounds include both aromatic and aliphatic compounds.
In another embodiment of the invention, the compound of formula I is represented by any of the general formulae given below:
In a further embodiment of the invention, the aminohydroxy compound contains at least one amino and at least one hydroxyl function.
In a further embodiment of the invention, the amine function may be primary or secondary in nature.
In one embodiment of the invention, the catalyst is selected from the group consisting of palladium, nickel, and platinum based catalysts or a mixture thereof.
In a further embodiment of the invention, the catalyst is selected from the group consisting of palladium bromide, iodide, chloride, perchlorate, organic acids salts such as acetate, trifluoroacetate; organic sulfonic acid salts such as p-toluenesulfonate, methanesulfonate or organometallic compounds like palladium acetylacetonate and the like.
In another embodiment of the invention, the catalyst is selected from the group consisting of PdCl
2
, PdBr
2
, Pd(OAc)
2
, Ni(OAc)
2
, NiCl
2
, Pd(acac), Pd(dba)
2etc
.
In another embodiment of the invention, the process of this invention is preferably carried out in presence of a ligand characterized by presence of at least one heteroatom selected from the group containing Nitrogen, Phosphorous, Sulfur and Arsenic or a combination thereof.
In a further embodiment of the invention, the ligand can be monodentate or multidentate, mono and bidentate being preferred.
In a further embodiment of the invention, the monodentate ligands include trialkyl, triaryl or alkylaryl phosphines such as Triphenylphosphine, tri-t-butylphosphine, tri-o-toluylphosphine, tricyclohexylphosphine, diethylphenylphosphine and the like, Nitrogen containing ligands such as Pyridine, quinoline, isoquinoline and the like; Arsenic containing ligands like triphenylarsine, triethylarsine and the like.
In a further embodiment of the invention, the bidentate ligands include 1,2 (diphenylphosphino) ethane, 1,3(diphenylphosphino)propane; 1,4diphenylphosphino)butane and alike, 2,2′bis(biphenylphosphino)-1,1′binaphthyl (BINAP), 2,2Bipyridine, 1,10Phenanthroline and the like.
In another embodiment of the invention, the ligand to metal mole ratio can be in the range of 0,1 to 100, 1-10 being preferred
In another embodiment of the invention, the CO pressure used may be in the range of 0.001 to 300 atm. and preferably in the range of 0.1 to 100 atms. CO used can be diluted by other gases like nitrogen, helium, argon or used alone.
In another embodiment of the invention, the base acting as a neutralizer for the hydrogen halide generated during the course of the reaction is selected from the group consisting of a strong hindered base such as 1,8-Diazabicyclo[5.4.0] undec-7-ene (DBU); 1,5-Diazabicyclo[2.2.0] non-5-ene (DBN); 1,4-Diazabicyclo[2.22] octane (DABCO) etc. or a tertiary amine represented by a general formula NR
3
, wherein each R is independently selected from a group consisting alkyl, aryl, cycloalkyl systems such as TEA, tri-t-butylamine and the like, inorganic bases like NaOH, K
2
CO
3
etc. and supported bases like polyvinylpyridine, polyvinylpyrrolidone.
In another e

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