Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1990-12-03
1993-04-06
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
558157, C07F 909
Patent
active
052005453
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new thiuram disulphides containing phosphate and phosphonate functional groups, to a process for the manufacture of these disulphides and to their use in the radical polymerization of vinyl monomers resulting in .alpha., .omega.-difunctional vinyl oligomers and polymers.
The invention also relates to these .alpha.,.omega.-difunctional vinyl oligomers and polymers which, containing the phosphate and phosphonate functional groups originating from these thiuram disulphides, can be used as fireproofing polymers. Furthermore, these vinyl oligomers and polymers can also be used as additives in the manufacture of fireproofing polymers, and can also be used to manufacture block polymers by condensation with other functional oligomers or polymers, these block polymers also constituting fireproofing polymers.
Functional vinyl polymers, which are sought after because they can form part of the composition of polymers with specific properties, for example with fireproofing properties in the case of the invention, were hitherto generally prepared by the anionic route, using the reaction of active anions with suitable electrophiles. However, polymerization of this type is difficult to apply on an industrial scale. This is why, in recent years, radical polymerization techniques have been proposed, employing monofunctional and, in some cases, difunctional free-radical producing agents, such as the azo systems and the Redox systems. However, the functional groups in these systems are limited to the hydroxyl and carboxyl functional groups.
Nonfunctional tetraalkylthiuram disulphides have already been described by Takayuki Otsu et al in Makromol Chem. Rapid Commun. 127--132 (1982), as agents performing the triple function of initiator, chain transfer agent and termination agent in the radical polymerization of vinyl monomers, such agents being denoted in this paper by the abreviation "iniferter". Functional thiuram disulphides are proposed in European Patent Application EP-A-0,237,792 as iniferters. The functional groups envisaged do not include the phosphate or phosphonate functional groups (P functional groups).
The Applicant Company has now found that, when iniferters containing phosphate or phosphonate functional groups are employed, it is possible to obtain polymers with ends carrying P functional groups, which have a fire resistance superior to that of polymers carrying P functional groups along the chain.
The subject matter of the present invention is therefore a chemical compound denoted by the formula (I): ##STR3## in which: each of R.sub.1 and R.sub.2, independently of each other, denotes: alkyl group, optionally interrupted by --0-- or ##STR4## a C.sub.3 -C.sub.12, in particular C.sub.5 -C.sub.7, cycloalkyl group; an aryl group, for example a phenyl or naphthyl group; ##STR5## and R.sub.4 denotes a phosphate or phosphonate functional group; of the definition of R.sub.1 and R.sub.2 ; it being possible for each of the groups R.sub.1, R.sub.2 and R.sub.3 to carry at least one functional group chosen from
the phosphate or phosphonate functional groups; on the condition that at least one of the radicals R and R.sub.2 consists of or carries at least one phosphate or phosphonate functional group, it being possible for this functional group to be carried by the radical R.sub.3 or R.sub.5.
There may be mentioned, in particular: C.sub.1 -C.sub.6 alkyl group, at least one out of these two groups carrying the phosphate or phosphonate functional group; ##STR6## in which: each of R.sub.6 and R.sub.7, which are identical or different, denotes an alkyl, alkoxy, aryl, aryloxy or ##STR7## group, R.sub.8 being chosen from the groups forming part of the definition of R.sub.1 and R.sub.2, it being possible for each of the groups R.sub.6, R.sub.7 and R.sub.8 to be sustituted by at least one halogen atom; Y.sub.1 denotes a single bond or --0-- or else ##STR8## R.sub.9 being chosen from the groups forming part of the definition of R.sub.1 and R.sub.2 ; and
The compounds of formula (I) which have just been
REFERENCES:
patent: 2784223 (1957-03-01), Scalera et al.
Orlov et al., Chemical Abstracts, vol. 83, No. 6, p. 3, No. 43805x, (1975).
Otsu et al., Makromol. Chem., Rapid Commun. 3, pp. 127-132 (1982).
Clouet Gilbert
Nair C. P. Reghunadhan
Elf Atochem S.A.
Reamer James H.
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