Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1994-05-19
1995-05-02
Kight, III, John
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
528176, 528193, 528194, C08G 6302
Patent
active
054120624
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention relates to novel polymers and their use in a variety of binder systems and, in particular, to the use of a novel thermally depolymerisable polyoxalate or polymalonate polymer as a binder for powdered glass, ceramic or metallic materials, and as a rheological control agent in paste formulations.
Thermally depolymerisable polycarbonates have been described by F. M. Houlihan, F. Bouchard, J. M. J. Frechet and G. G. Wilson in Macromolecules 1986, 19, 13-19. The materials which are described are polycarbonates containing a tertiary group next to the main chain oxygen which were prepared by using a solid-liquid phase-transfer-catalyzed polycondensation of the bis(carbonylimidazolide) of 2,5-dimethyl-2,5-hexanediol with various other diols in the presence of powdered potassium carbonate. These polycarbonates decompose cleanly upon heating to about 220.degree. C. with liberation of volatile materials, leaving no solid residue.
In EP-0463796A we have described compositions in which at least one powdered material is admixed with at least one thermally depolymerisable polycarbonate containing the repeating units ##STR1## where R.sup.5 and R.sup.6 are the same or different and each independently represents a hydrocarbon group containing from 4 to 30 carbon atoms, the said group having a tertiary carbon atom, an allylic, propargylic or benzylic group attached directly to at least one oxygen atom.
SUMMARY OF THE INVENTION
We have now surprisingly found that certain novel thermally depolymerisable polyoxalates and polymalonates can be used as binders for a variety of powdered materials, and as rheological control agents in paste formulations. Furthermore, these materials depolymerise on heating to liberate volatile molecules. This process does not require the presence of oxygen and can be processed in an inert atmosphere such as nitrogen.
In one aspect the present invention provides a polymer or copolymer containing repeating groups of the formula ##STR2## where R.sup.1 and R.sup.2 are each independently a hydrocarbon group containing from 3 to 30 carbon atoms which has a tertiary carbon atom attached to at least one of the bridging oxygen atoms,
R.sup.3, R.sup.3' R.sup.4, R.sup.4' are each independently a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aryl group, a heterocyclic group or an acyl group containing from 1 to 12 carbon atoms, and
n and n' are 0 or 1.
When n and n' are 0 the polymers are polyoxalates and when n and n' are 1 the polymers are polymalonates. When n and n' are 1 preferably R.sup.3, R.sup.3' and R.sup.4, R.sup.4' are both hydrogen atoms, or one of R.sup.3, R.sup.3' and R.sup.4, R.sup.4' is a hydrogen atom and the other is an acyl group containing from 1 to 12 carbon atoms, and most preferably, when n and n' are 1, R.sup.3, R.sup.3' and R.sup.4, R.sup.4' are hydrogen atoms.
The present invention also includes within its scope polymers in which one of n and n' is 0 and the other of n and n' is 1, i.e. copolymers of oxalate/malonate.
The present invention furthermore includes a copolymer which comprises groups of the formula ##STR3## where R.sup.1, R.sup.2, R.sup.3, R.sup.3', R.sup.4, R.sup.4' n and n' are each as defined above and groups of the formula ##STR4## where R.sup.5 and R.sup.6 each independently represents a hydrocarbon group containing from 4 to 30 carbon atoms, the said group having a tertiary carbon atom, an allylic, propargylic or benzylic group attached directly to at least one oxygen atom, i.e. copolymers of oxalate/carbonate or malonate/carbonate.
The novel polymers of the present invention may be produced by the condensation reaction between a diol, or a mixture of diols and an oxalyl and/or malonyl moiety, such as an acid chloride, acid or ester.
The diols which may be used in the preparation of the novel polymers of the invention have the general formula:
The novel polymers of the present invention owe their thermal lability to the structure of the diols which are used in their preparation, as a result
REFERENCES:
patent: 3043808 (1962-07-01), Hagemeyer
patent: 3169121 (1965-02-01), Goldberg
patent: 4343912 (1982-08-01), Lim
patent: 4446271 (1984-05-01), Heater
patent: 5114983 (1992-05-01), Stahlke et al.
patent: 5126380 (1992-06-01), Stahlke et al.
Mackie Andrew C.
Power Gerald A.
Wagland Alison M.
Cookson Group PLC
Kight III John
Mosley Terressa M.
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