Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Nitrogen-containing reactant
Patent
1998-06-18
2000-03-14
Truong, Duc
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Nitrogen-containing reactant
528422, 528367, 528368, 528369, C08G 7300, C08G 7306
Patent
active
060374446
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to selective chemical reactions and to branched molecules, including dendritic polymers, and to polymers tipped with functional groups. By selective chemical reactions we mean reactions of a compound or polymer containing two different functional groups with a reagent which reacts only or predominantly with one of the said functional groups, leaving the other functional group free to take part in a subsequent chemical reaction.
Dendritic polymers, otherwise known as dendrimers, comprise a multivalent core surrounded by layers of branched structural units. The successive layers around the core are called generations and in each generation the degree of branching of the structural units multiplies. The dendritic polymers thus have a substantially spherical molecular structure with a very large number of terminal groups at the surface of the molecule; the terminal groups may be functional groups so that the dendritic polymer may have very high functionality compared to its molecular size.
BACKGROUND ART
Dendritic polymers, particularly polyamidoamines and amidoalcohols, polyethers, polythioethers, polyethyleneimines and polyamides are described in Encyclopaedia of Polymer Science and Engineering, index volume, 1990, John Wiley & Sons, New York in an article by D. A. Tomalia et al. at pages 46-92. Dendritic polyesters are described in WO-A-93/18075. U.S. Pat. No. 5,229,490 describes dendritic polyamides having antigens bound thereto.
The spherical nature of dendrimers leads to high molecular weight molecules which do not suffer from entanglement, unlike conventional linear chain polymers. Dissolution in solvents is therefore fast and viscosities are low, leading to the possibility of "high solids" formulations, for example of coatings, sealants or adhesives, with favourable physical properties. The crosslinking of dendrimers leads to the formation of highly branched networks even after very few reactions have occurred, and the subsequent increase in molecular weight is dramatic, leading initially to linear-like entangled networks and then to highly crosslinked materials.
There is a need for dendrimers based on a wider range of chemical linkages and for alternative methods of preparation of dendrimers.
Functionally tipped polymers are known; for example hydroxyl and amino tipped polyethers, amino tipped polyamides and carboxyl tipped diene polymers are available commercially. There is a need for polymers tipped with a plurality of functional groups at each end and for convenient reactions for changing the terminal functionality of a polymer.
A paper by F. M. Houlihan et. al. in Macromolecules 1986, 19, pp 13-19, describes the synthesis of linear tertiary polycarbonates by reacting a ditertiary alcohol with carbonyl diimidazole and reacting the product with a diprimary alcohol.
DISCLOSURE OF THE INVENTION
According to one aspect of the invention, a process for the preparation of a compound or polymer having at least one functional group selected from hydroxyl, thiol, amino and carboxylic acid groups is characterised in that a compound or polymer (A) containing a group of the formula: ##STR2## where Q represents O or S and X represents --O--, --S--, --NH-- or a direct bond, the group being linked to the remainder of the compound or polymer through a carbon atom, is reacted with a compound (B) containing at least two functional groups selected from hydroxyl, thiol, amino and carboxylic acid groups, one of which functional groups (II) reacts with the group of formula (I) and one of which functional groups (III) is substantially unreactive with the group of formula (I), so that the compound (B) becomes bonded to (A) through the reaction of groups (I) and (II) forming a compound or polymer containing unreacted functional groups (III).
In a related process according to the invention for the preparation of a substituted amide, a compound containing an aliphatic carboxylic acid group and at least one substituent selected from alcohol and thiol groups is reacted with c
REFERENCES:
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Chem Abstract: 123:144777 "Rigid rod polyimides with n-alkoxymethyl side chains" "Park et al."
A. Kumar et al., "A Novel One-pot Synthesis of Hyperbranched Polyurethanes" J. Chem. Soc., Chem. Commun., 1993; pp. 1453-1454.
CA 123:83995 and J. Shao et al., "Unprotected Peptides as Building Blocks for the Synthesis of Peptide Dendrimers with Oxima, Hydrazone, and Thiazolidine Linkages" J. Am. Chem. Soc., vol. 117, No. 14, 1995; pp. 3893-3899.
CA 117:112473 and A.D. Meltzer et al., "Chain Dynamics in Poly(amido amine) Dendrimers. A Study of C NMR Relaxation Parameters" Macromolecules, vol. 25, No. 18, 1992; pp. 4541-4548.
D.A. Tomalia et al., "Dendritic Polymers" Encyclopaedia of Polymer Science and Engineering, Index Volume, 1190, John Wiley & Sons, New York; pp. 46-92.
F.M. Houlihan et al., "Thermally Depolmerizable Polycarbonates. 2. Synthesis of Novel Linear Tertiary Copolycarbonates by Phase-Transfer Catalysis" Macromolecules, vol. 19, No. 1, 1986; pp. 13-19.
Davis Nicola Jane
Rannard Steven Paul
Courtaulds Coatings (Holdings) Limited
Truong Duc
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