Nitrogenous multiacrylic monomers, their preparation and their a

Details Nitrogenous multiacrylic monomers, their preparation and their a Nitrogenous multiacrylic monomers, their preparation and their a

1994-01-18

1996-09-10

Bleutge, John C.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

525540, 525912, 525922, 528 93, 528103, C08F28300, C08F28310

Patent

active

055547036

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

The present invention relates to new nitrogeneous multiacrylic monomers, a process for their preparation and their application to the synthesis of new polymers.
Through the patent publication WO 86/06716 are already known monomers having the formula: ##STR1## wherein R.sub.1 is an acrylic or methacrylic group corresponding to the formula ##STR2## R.sub.3 being selected from a hydrogen atom and a methyl group, R.sub.2 is a hydrogen atom, a saturated aliphatic group comprising up to 10 carbon atoms or a group identical to R.sub.1 ; and non-substituted aliphatic or aromatic ring.
These monomers lead, by radical polymerisation or copolymerisation, to polymers having thermal properties significantly better than those obtained from conventional acrylic monomers. However the applicant discovered that these polymers have the disadvantage of an important brittleness probably due to their too high crosslinking density. On the other hand, the synthesis of the monomers (A) involves a glycidyl acrylate or methacrylate whose reactivity with a diamine having the formula H.sub.2 N--R--NH.sub.2 is insufficient under the conditions described in this document.


SUMMARY OF THE INVENTION

An objective of the present invention therefore consists in designing polymers which, while keeping the good thermal properties of the polymers described in the patent publication WO 86/06716, further show good mechanical properties, in particular the absence of brittleness, and which may be obtained from epoxides having a high reactivity towards diamines having the formula H.sub.2 N--R--NH.sub.2.
Surprisingly this objective has been achieved by providing new nitrogeneous multiacrylic monomers which constitute a first object of the present invention. This family of new monomers may be represented by the formula (I) hereinafter: ##STR3## wherein: n is an integer at least equal to 0, are selected, independently from each other, from a hydrogen atom and acrylic or methacrylic groups having the formula ##STR4## R.sub.10 being selected from a hydrogen atom and a methyl group, X being selected from the sulfur and oxygen atoms and R' being a hydrocarbon group of 2 to 20 carbon atoms comprising a hydroxyl group within the backbone or at the end of the chain, selected from linear or branched alkyl groups, monocyclic or polycyclic cycloalkyl or heterocycloalkyl groups and alkylaryl groups, --O--CH.sub.2 -- wherein R.sub.11 is a bivalent group selected from alkylene groups having from 2 to 12 carbon atoms and those comprising at least a substituted or non-substituted aliphatic or aromatic ring, and non-substituted aliphatic or aromatic ring, R.sub.8 and R.sub.9 are acrylic or methacrylic groups, and R.sub.3, R.sub.5, R.sub.6, R.sub.7 R.sub.8 and R.sub.9 are acrylic or methacrylic groups.
Group R and group R.sub.11, when the latter is not an alkylene group, may contain two joined aliphatic or aromatic rings and may be in the form of R.sub.12 --R.sub.13 --R.sub.12 where R.sub.12 represents a cyclic or aromatic group preferably comprising from 5 to 10 carbon atoms substituted or unsubstituted by aliphatic groups or by heteroatoms, such as for example: ##STR5## where R.sub.14 represents a hydrogen or halogen atom or a methyl, ethyl or isopropyl group, and where R.sub.13 represents a group which may be either a single atom (such as oxygen) or a group of atoms comprising carbon, hydrogen, oxygen and/or sulfur atoms, capable of linking the R.sub.12 cycles by means of alkylene groups such as methylene or ethylene, or by means of ether or sulfone linkages.
Group R and group R.sub.11, when the latter is not an alkylene group, may contain a single substituted or unsubstituted aliphatic or aromatic ring, such as for example: ##STR6##
A second object of the present invention consists of a process for preparing monomers of the formula (I), comprising the reaction of at least a diamine having the formula H.sub.2 N--R--NH.sub.2 (wherein R is as hereinabove defined) with at least a polyepoxidic resin and with at least a (meth)acrylic epoxid

REFERENCES:
patent: 4704437 (1987-11-01), Kiessling
patent: 5153277 (1992-10-01), Awaji et al.
patent: 5235008 (1993-08-01), Hefner et al.
Encyclopedia of Science and Technology, vol. 6, 1986 pp. 348-352.

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