Furan polyols

Details Furan polyols Furan polyols

1988-08-22

1990-11-27

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549472, 549486, 549488, 549491, C07D30742, C07D30752, C07D30754

Patent

active

049737155

DESCRIPTION:

BRIEF SUMMARY
The present invention essentially relates to novel furan polyols, to the use thereof as polyols in the formation of polyurethanes, to polyurethanes thus obtained, and to a process for preparing same.
The flame-retardant properties of the furan cycle owing to the self-extinguishing property of the charring which is formed when compounds containing a furan cycle are burnt, are already known, cf. U.S. Pat. Nos. 4,029,611, 3,865,757 and 4, 318,999.
In particular, in U.S. Pat. No. 4,318,999, the furan compound is constituted by 2,5-bis-(hydroxymethyl)furan in combination with a halogenated polyol to constitute the polyol component made to react with an isocyanate, for the manufacture of rigid polyurethanes with improved flame resistance. Comparisons are made with furfurylalcohol or with polyhydroxyfuran as the sole polyol ingredient (tests B and C, Table 1, columns 5 and 6).
Similarly, FR-A-No. 2 536 750 describes novel furan compounds with terminal hydroxy groups, capable of forming active components of rigid compositions of urethane and of isocyanurate with reduced inflammability. The use of 2,5-bis-(hydroxymethyl) furan (BHMF) is described, of which the chain extension is obtained by propoxylation (page 4, lines 6-12, Examples 1, 2). The use is preferred of homopolymers of BHMF (page 4, line 13 to page 9, line 30; Example 3, BHMFP Table III, Example 5, Example 6, claims).
However, it has appeared that the BHMF presents a low reactivity, which considerably limits the use thereof.
Likewise, it has appeared that the mechanical properties of these polyurethanes were still unsatisfactory, particularly their dimensional stability in damp heat as well as an insufficient behavior in temperature.
It is therefore an object of the present invention to solve the new technical problem consisting in providing a solution furnishing novel polyols of the furan type capable of significantly improving the behaviour of polyurethanes in temperature, their dimensional stability in damp heat.
The present invention makes it possible to solve this new technical problem for the first time in satisfactory manner.
According to the present invention, novel furan polyols are thus produced, characterized in that they are the product of reaction of: monoamine or polyamine, said polyol or said amine possibly containing at least one furan cycle, and mixtures thereof: cycle constituted by an organic epoxide, with the proviso that this organic epoxide is a furannic oxiran when this strain does not contain a furan cycle; with the exclusion of 2,5-bis-(hydroxymethyl)furan as sole strain, when the chain extension agent does not contain a furan cycle.
According to a particular feature, this amine is a primary or a secondary (mono- or poly-)amine.
According to another feature, this amine can contain one or several hydroxy functions (groups). When this amine contains at least a hydroxy function, preferably at least two hydroxy functions, said hydroxylated amine can be a tertiary amine. This hydroxylated amine is simultaneously a polyalcohol of the invention which is aminated.
According to a preferred embodiment, the polyalcohol mentioned above responds to the following chemical formula (I): ##STR1## in which R.sup.1, R.sup.2, R.sup.3 may be identical or different and represent H, a lower alkyl group with C.sub.1 -C.sub.5, preferably C.sub.1 -C.sub.3, an aliphatic group with alcohol function with C.sub.1 -C.sub.4, an aliphatic group with acid function with C.sub.1 -C.sub.4 or ester with a lower alkyl ester radical with C.sub.1 -C.sub.5, preferably C.sub.1 -C.sub.3, an aliphatic group with ketone function with C.sub.1 -C.sub.4, an aliphatic group with aldehyde function with C.sub.1 -C.sub.4 ; n=0 to 10, with the proviso, that, when n=0, at least one of the R.sup.1, R.sup.2, R.sup.3 is a group with alcohol function, R.sup.1 not being able to be --CH.sub.2 OH if the chain extension agent does not contain a furan cycle; preferably n=1 to 10, and, further preferably n=1 to 3.
The aliphatic groups hereinabove are preferably straight-chain but may be branch

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