Compositions – Compositions containing a single chemical reactant or plural... – Organic reactant
Patent
1995-01-09
1996-04-30
McKane, Joseph K.
Compositions
Compositions containing a single chemical reactant or plural...
Organic reactant
25218223, 25218224, 25218225, 252350, 521166, 528 73, 548558, C07D20704
Patent
active
055122043
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/NL 93/00070 filed Mar. 26, 1993.
The invention relates to imino-azacyclopentanepolyols. Polyols of this type are novel. Polyols based on azacyclic compounds are known and are used, inter alia, as crosslinking agents or chain extenders in polymers to be produced by means of a polycondensation reaction, such as polyurethane, RIM nylon and thermosetting resins. In this context, the nitrogen-containing polyols offer the advantage of flame retardancy.
The imino-azacyclopentanepolyol according to the invention has the general formula ##STR2## wherein R.sup.1 =H, alkyl or R.sup.4, whereby R.sup.4 is OH, hydroxyalkyl, hydroxyaryl or hydroxyaralkyl and hydroxyaryl or hydroxyaralkyl.
Mixtures of imino-azacyclopentanepolyols according to the above formula also fall under the invention. For use as a crosslinking agent, R.sup.1 is preferably R.sup.4.
In another preferred embodiment of the invention, R.sup.1 is H, C.sub.1 -C.sub.6 alkyl or phenyl.
Preferably, R.sup.2, R.sup.3 and/or R.sup.4 are chosen such that they have a hydrocarbon chain with a number of carbon atoms in the chain of between 1 and 12 and more preferably between 2 and 6. Long chains can increase the inflammability.
Preferred hydroxyalkyl groups are hydroxyalkyl groups derived from linear alkanes, because steric hindrance can easily occur in the case of branched hydrocarbons and the formation of a triol consequently becomes difficult. Specifically, the .alpha. atom, and in particular the .alpha. and .beta. atoms, with respect to the nitrogen atom are unsubstituted.
Examples of suitable hydroxyalkyl chains are 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxy-n-butyl, 3-hydroxy-n-butyl, 4-hydroxy-n-butyl, 3-hydroxy-n-pentyl, 5-hydroxy-n-pentyl, 6-hydroxy-n-hexyl, 6-hydroxy-2-ethyl-hexyl and .omega.-hydroxy-dodecyl. 2-Hydroxyethyl, 3-hydroxy-propyl or 4-hydroxy-n-butyl is preferably used. Examples of hydroxyaryl and hydroxyaralkyl chains are p-hydroxy-phenyl, p-hydroxy-benzyl, p-hydroxyethylbenzyl, p-hydroxy-methylbenzyl, 5-hydroxy-3-phenylpentyl and 3-hydroxy-3-phenyl-hexyl.
Polyol derivatives (i.e. hydroxy functional oligomers or polymers) obtained with the polyols according to Formula (1) as a starting product also constitute part of the invention. Such a polyol comprises a polyether, a polyester or a vinyl polymer or combinations thereof.
Polyol derivatives of this type can be obtained using methods known per se. For example, the polyetherpolyols can be obtained by catalytic polycondensation of an alkylene oxide or a mixture of alkylene oxides in the presence of the polyol according to Formula (1).
Polyester-polyols can be prepared, for example, by reaction of the polyol according to Formula (1) with lactones, a polycarboxylic acid or the corresponding anhydride, acid chloride or ester. The polyesters can be saturated or (ethylenically) unsaturated.
One method of preparation for vinylpolymer-containing polyols is, for example, the in situ free radical polymerisation of an ethylenically unsaturated monomer or a mixture of monomers in the polyol according to Formula (1). Suitable monomers are, for example, vinyl-aromatic monomers, such as, for example, styrene, and acrylic monomers, such as, for example, acrylonitrile, methyl methacrylate, butyl acrylate and acrylic acid.
An extensive list of suitable polyethers, polyesters and vinyl polymers is to be found, inter alia, in U.S. Pat. No. 4,826,884 and the references cited therein.
Polymers in which the polyols according to Formula (1) or the polyols obtained from the polyols according to Formula (1) are incorporated and in which a polyether, a polyester or a vinyl polymer or combinations thereof are also incorporated constitute a further part of the invention.
Polymers of this type are preferably polymers which are obtained by means of a polycondensation reaction and comprise, inter alia, the thermoplastic polyesters, polyamides, in particular polyamides which can be obtained by means of anionic polymerisation of lactams, for example RIM nylons, and thermosettin
REFERENCES:
patent: 2569428 (1950-07-01), Rowland
patent: 3309380 (1967-03-01), Greene
patent: 4704411 (1987-11-01), Gansow et al.
patent: 4826884 (1989-05-01), Grace et al.
Chemical Abstracts, 74:140613e (1971), Amino . . . derivatives. Armand et al. p. 498.
Chemical Abstracts, 66:8018h (1967), Reactivity . . . dioxime. Buscarous et al., p. 773.
Chemical Abstracts, 67: 43591u (1967), 1,2-Cyclobutanedicarboximidines and -dicarboximinoimides. Greene, p. 4088.
CA 77: 96640x Specific reaction of succinimidodioximes. Buscarons et al., p. 604, 1972.
CA 120: 77271t Process for . . . bis(2-oxazolines). Weerts et al., p. 879, 1994.
CA 120: 246619v N-substituted . . . reactions. Kierkels et al., p. 55, 1994 .
Aarts Veronika M. L. J.
Kierkels Renier H. M.
Stanssens Dirk A. W.
DSM N.V.
McKane Joseph K.
LandOfFree
Imino-azacyclopentanepolyol does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Imino-azacyclopentanepolyol, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Imino-azacyclopentanepolyol will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-626015