Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Patent
1995-08-09
1997-03-11
Hoke, Veronica P.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
524102, 524131, 524132, 546 22, 546 24, 558167, 558168, 558169, C08K 55373, C08K 55333, C07F 906, C07C22900
Patent
active
056102100
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the use of aminovinylphosphonic esters of the general formula I ##STR3## where
R.sup.1 is cyano, a radical of the formula --CO--OR.sup.6 or a group of the formula ##STR4##
R.sup.2, R.sup.3 and R.sup.6 are C.sub.1 -C.sub.20 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, C.sub.7 -C.sub.18 -aralkyl, phenyl or tolyl,
R.sup.4 is phenyl which may be substituted by one to three C.sub.1 -C.sub.12 -alkyl groups, C.sub.1 -C.sub.12 -alkoxy groups, halogen atoms, cyano groups, hydroxyl groups, phenyl groups or groups of the formula --CO--OR.sup.6, --CO--R.sup.6, --CO--NHR.sup.6, --O--CO--R.sup.6 or --NH--CO--R.sup.6, or is a five-membered or six-membered unsaturated or saturated heterocyclic ring having up to three heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, which may additionally be benzofused and may be substituted by one to three C.sub.1 -C.sub.12 -alkyl groups, C.sub.1 -C.sub.12 -alkoxy groups, halogen atoms, cyano groups, hydroxyl groups, phenyl groups, phenoxy groups or C.sub.1 --C.sub.12 -alkoxycarbonyl groups, or is a group of the formula ##STR5##
R.sup.5 is hydrogen or C.sub.1 -C.sub.12 -alkyl,
R.sup.7 is hydrogen, C.sub.1 -C.sub.6 -alkyl, formyl, C.sub.2 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.5 - or C.sub.6 -cycloalkoxy, cyanomethyl, 2-hydroxyethyl, benzyl or a radical of the formula --CR.sup.8 .dbd.CH--CO--OR.sup.6,
R.sup.8 is hydrogen, C.sub.1 -C.sub.6 -alkyl or a radical of the formula --CO--OR.sup.6, and
X is oxygen or NH,
Since some of the compounds I are novel substances, the present invention also relates to these novel substances.
The present invention furthermore relates to organic material stabilized to the action of light, oxygen and heat by means of the compounds I, in particular stabilized plastics and coatings.
It is known that organic material, in particular plastics and coatings, is very rapidly destroyed, particularly by the action of light. This destruction usually manifests itself in yellowing, discoloration, cracking or embrittlement of the material. The intention is therefore to use light stabilizers and stabilizers to achieve satisfactory protection from the destruction of organic material by light, oxygen and heat.
Thus, U.S. Pat. No. 3,079,366 (1) describes, inter alia, alkyl 3-(arylamino)-2-cyanoacrylates and alkyl 3-(arylamino)-2-(alkoxycarbonyl)acrylates as light stabilizers for plastics.
Some of the compounds I are known from the literature. Thus, German Laid-Open Application DOS 1,911,768 (2) relates to, inter alia, phosphonic esters having .alpha.-(alkoxycarbonyl)-.beta.-(C.sub.6 - or C.sub.7 -arylamino)vinyl groups; these compounds are recommended as reagents for aldehyde synthesis, in particular for formyl olefination. Phosphorus and Sulfur, 31 (1987), 231-243 (3), discloses the compound diethyl .alpha.-cyano-.beta.-(phenylamino)vinylphosphonate. However, neither (2) nor (3) refers to the use as a light stabilizer or stabilizer.
The excessively low compatibility of the plastics, the excessively short duration of the protective effect, the natural color of the substances, the tendency to volatility and thermal decomposition of the stabilizers during incorporation at elevated temperatures are frequently unsatisfactory in the case of the stated prior art compounds.
It is an object of the present invention to provide light stabilizers or stabilizers which more effectively protect organic material.
We have found that this object is achieved by the aminovinylphosphonic esters I defined at the outset.
Examples of suitable straight-chain or branched alkyl radicals for R.sup.2, R.sup.3 and R.sup.5 to R.sup.8 and as substituents on the phenyl nucleus and on heterocyclic rings and as the alcohol radical in alkoxycarbonyl groups, which are referred to as C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.12 -alkyl and C.sub.1 -C.sub.20 -alkyl radicals, are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl, isoamyl, sec-amyl, tert-amyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-non
REFERENCES:
patent: 3079366 (1963-02-01), Boyle et al.
patent: 3462439 (1969-08-01), Popoff et al.
patent: 3885912 (1975-05-01), Golborn et al.
patent: 4388252 (1983-06-01), Duersch et al.
patent: 5260286 (1993-11-01), Lawson et al.
Phosphorus and Sulfur, 1987, vol. 31, pp. 231-243.
Aumueller Alexander
Holderbaum Martin
Trauth Hubert
BASF - Aktiengesellschaft
Hoke Veronica P.
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