Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1995-12-05
1998-04-28
Cooney, Jr., John M.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
528318, 549475, 549480, C08G 6908, C07D30702
Patent
active
057445745
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to isomaleimides and polyisomaleimides, a method of preparation thereof, and polymers (i.e., polymaleamides) obtained therefrom. Polymaleamides of the invention find use as adhesives, sealants, molding compounds, protective coatings, binders for abrasives, potting compounds, and crosslinking agents for hybrid materials systems. Isomaleimides and polyisomaleimides of the invention find use as surface-active agents.
BACKGROUND OF THE INVENTION
Ambient-curable polymeric materials having useful properties are in constant demand in the chemical industry. For many years, polyurethanes have filled this need, and their pervasiveness in commerce is testimony to their versatility and utility. However, polyurethanes are prepared from polyisocyanates, materials that have become increasingly regulated.
Isomaleimides and bis(isomaleimides) are known. They are generally obtained from the reaction of amines with maleic anhydride to form a maleamic acid, followed by cyclic dehydration of the maleamic acid to form an isomaleimide. While the formation of maleamic acids is relatively straightforward, the subsequent cyclic dehydration procedures disclosed in these references sometimes require expensive reagents and/or conditions that do not always provide high yields of pure isomaleimides. In particular, it is known that acids, bases, and heat catalyze the isomerization of isomaleimides to maleimides, and that thermodynamically-favored maleimide is often isolated in preference to the kinetically-favored isomaleimide.
Known low molecular weight, non-polymeric bis(isomaleimides) are all crystalline solids. Therefore, when used in reactions subsequent to their isolation, these solid materials must be taken up in a solvent whose cleanup and disposal may be difficult, expensive, and/or hazardous.
Polymers derived from non-polymeric bis(isomaleimides) are known. They have been obtained by the reaction of suitable bis(isomaleimides) with primary or secondary diamines to produce polymaleamides or with dihydric phenols to produce poly (half-ester half-maleamides). All of the diamine polymerization reactions described were carried out in an organic solvent or diluent.
SUMMARY OF THE INVENTION
Briefly, this invention provides a novel method for the preparation of isomaleimides and polyisomaleimides comprising the steps, in sequence: acid halide, sufficiently low to suppress the formation of a maleimide, and
"Polyisomaleimide" means a molecule having two or more isomaleimide functionalities.
A maleamic acid or a polymaleamic acid, reactants in this method, can be prepared, as is known in the art, by reacting a compound comprising one or more primary amine groups with maleic anhydride. It is understood that because the primary amine can be polymeric or nonpolymeric, the terms "polyamine," "polymaleamic acid," and "polyisomaleimide" also encompass "polymeric polyamine," "polymeric polymaleamic acid," and "polymeric polyisomaleimide," respectively.
In yet another aspect, the invention provides novel polyisomaleimides of the general formula (1): ##STR1## wherein R represents a polyvalent organic group derived from a polymeric primary polyamine by replacement of both hydrogen atoms from each amino group for each isomaleimide group formed, and selected from the group consisting of hydrogen, C.sub.1 to C.sub.20 linear, branched or cyclic aliphatic groups, C.sub.6 to C.sub.20 aromatic groups (e.g., phenyl, naphthyl, benzyl), fluorine, chlorine, bromine, and iodine, or R.sup.1 and R.sup.2 may be joined together to form a cyclic ring that may be aromatic or alicyclic; at least 2, preferably from 2 to about 50,000, more preferably from 2 to 5000, most preferably from 2 to 100, and even more preferably from 2 to 10.
In a preferred embodiment, R represents a divalent organic group derived from a compound having two primary amine groups, R.sup.1 and R.sup.2 are hydrogen, and n is 2.
Preferably, polymeric polyisomaleimides of the invention are liquids at ambient temperatures (i.e., approximately 20.de
REFERENCES:
patent: 2980701 (1961-04-01), Sauers et al.
patent: 2995577 (1961-08-01), Sauers et al.
patent: 2998429 (1961-08-01), Sauers et al.
patent: 3035065 (1962-05-01), Sauers et al.
patent: 3041376 (1962-06-01), Sauers et al.
patent: 3144435 (1964-08-01), Sauers et al.
patent: 3232763 (1966-02-01), Burness et al.
patent: 3631005 (1971-12-01), Fan
patent: 4179444 (1979-12-01), Roth
patent: 4581461 (1986-04-01), Rossi et al.
patent: 4732963 (1988-03-01), Wank et al.
patent: 4782133 (1988-11-01), deKoning et al.
patent: 5079338 (1992-01-01), Schenach et al.
patent: 5082920 (1992-01-01), Harper
Imai, et al., J. Poly. Sci., Poly. Chem., 13, 1691-1698 (1975).
Cotter et al., J. Org. Chem., 26(1) 10-15 (1961).
Nagarathinam et al., Polymer Bulletin 16, 147-151 (1986).
Nagarathinam et al.., J. Macromol. Sci.-Chem., A25(12), pp. 1675-1682 (1988).
Nagarathinam, et al., British Polymer Journal 22 (1990) 351-356.
Chisholm, et al., Polymer, 1992, vol. 33, No. 4.
Fan, Macromolecule, vol. 9, No. 1, Jan-Feb 1976.
Jacovic et al., Polymer Engineering & Science, August 1985, vol. 25, 12.
Ueda, et al., Journal of Polymer Science, Polymer Chem. Edition, vol. 13, 2735-2740 (1975).
Rajeswari, et al., Indian Journal of Chemistry, vol. 28A, Nov. 1989, pp. 965-968.
Nagarathinam, et al., Polymer Journal, vol. 18, No. 11, pp. 865-869 (1986).
Pyriadi et al., Arab Gulf J. Scient. Res. Math Phys. Sci., A5(3), pp. 341-348 (1987).
Anderson Gregory J.
Ezzell Stephen A.
Hansen Richard G.
Cooney Jr. John M.
Minnesota Mining and Manufacturing Company
Sherman Lorraine R.
LandOfFree
Isomaleimides and polymers derived therefrom does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Isomaleimides and polymers derived therefrom, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Isomaleimides and polymers derived therefrom will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1532823