Synergistic stabilizer mixture based on...

Details Synergistic stabilizer mixture based on... Synergistic stabilizer mixture based on...

1998-08-13

2001-01-16

Niland, Patrick D. (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S095000, C524S096000, C524S097000, C524S100000, C524S102000, C524S103000, C524S425000, C524S440000, C252S401000, C252S403000, C540S466000, C540S543000, C540S598000, C544S096000, C544S209000, C544S212000, C544S113000, C544S219000, C546S014000, C546S018000, C546S019000, C546S020000

Reexamination Certificate

active

06174940

ABSTRACT:

BACKGROUND OF THE INVENTION
It is known that organic materials are damaged by light, radiation, heat or oxygen. There are already numerous documents which describe compounds for stabilizing organic material against the effects of light and heat. Some of these documents relate to compounds based on 2,2,6,6-tetraalkylpiperidine. These stabilizers must be present in sufficient concentration especially at the exposed areas of the organic material in order to provide effective protection. The low molecular mass representatives from the class of substance of the 2,2,6,6-tetraalkylpiperidines have the advantage of migrating rapidly to the areas particularly exposed to the damaging influences, where they exert their protective influence. Nevertheless, they have the disadvantage that they possess excessive volatility and, in addition, are readily extractable from the organic material. The higher molecular mass representatives of this class of substance, although not so readily extractable, are much slower to migrate. In the art this problem is often solved by employing a mixture of low molecular mass (rapidly migrating) and high molecular mass (slowly migrating) stabilizers.
A considerable number of stabilizer mixtures based on sterically hindered amines have been presented which possess the abovementioned disadvantages to a lesser degree if at all. By way of example there may be mentioned mixtures as described, for example, in U.S. Pat. No. 4,692,486, U.S. Pat. No. 4,863,981, U.S. Pat. No. 4,957,953, WO-A-92/12201, WO-A-94/22946, EP-A449685, EP-A-623 092, GB-A-2 267 499, DE-A-1 9613 982 and in Research Disclosure No. 34549 (Jan. 1993). However, there is a constant demand for new, more effective stabilizer mixtures which give organic material improved photoprotective or service properties.
It has surprisingly now been found that the compound I in a mixture with the compound II and, if desired, with the compound III stabilizes organic material extremely well against the damaging effects of light, radiation, heat or oxygen.
SUMMARY OF THE INVENTION
The invention hence provides mixtures comprising the compound I in a proportion of 65-95, preferably from 75 to 94 and, in particular, from 85 to 94% by weight, the compound II in a proportion of from 5 to 35, preferably from 5 to 20 and, in particular, from 5 to 12% by weight and the compound III in a proportion of from 0 to 10, preferably from 1 to 5 and, in particular, from 1 to 3% by weight.
in which
n and m independently of one another are a number from 0 to 100, but n and m cannot both be 0,
R
1
is hydrogen, C
5
-C
7
-cycloalkyl, or a C
1
-C
12
-alkyl group,
R
2
and R
3
independently of one another are a hydrogen atom or a C
1
-C
18
-alkyl group or, together with the carbon atom connecting them, are a 5- to 1 3-membered ring or, together with the carbon atom connecting them, are a group of the formula (IV)
R
4
and R
5
independently of one another are either hydrogen or a C
1
-C
22
-alkyl group, an oxygen radical O*, —OH, —NO, —CH
2
CN, benzyl, allyl, a C
1
-C
30
-alkyloxy group, a C
5
-C
12
-cycloalkyloxy group, a C
6
-C
10
-aryloxy group in which additionally the aryl radical may also be substituted, a C
7
-C
20
-arylalkyloxy group in which additionally the aryl radical may also be substituted, a C
3
-C
10
-alkenyl group, a C
3
-C
6
-alkynyl group, a C
1
-C
10
-acyl group, halogen or unsubstituted or C
1
-C
4
-alkyl-substituted phenyl.
In order to avoid any confusion this mixture of the invention is referred to below as mixture M.
Also highly suitable are mixtures in which
n and m independently of one another are a number from 0 to 10, but n and m cannot both be 0,
R
1
is hydrogen, C
6
-cycloalkyl, or a C
1
-C
4
-alkyl group,
R
2
and R
3
independently of one another are a hydrogen atom or a C
1
-C
6
-alkyl group or, together with the carbon atom connecting them, are a 6- to 12-membered ring or, together with the carbon atom connecting them, are a group with formula (IV),
R
4
and R
5
independently of one another are either hydrogen or a C
1
-C
5
-alkyl group, an oxygen radical O*, —OH, —NO, —CH
2
CN, benzyl, allyl, a C
1
-C
10
-alkyloxy group, a C
5
-C
6
-cycloalkyloxy group, a C
6
-C
7
-aryloxy group in which additionally the aryl radical can also be substituted, a C
7
-C
10
-arylalkyloxy group in which additionally the aryl radical can also be substituted, a C
3
-C
6
-alkenyl group, a C
3
-C
6
-alkynyl group, a C
1
-C
4
-acyl group, halogen or unsubstituted or C
1
-C
2
-alkyl-substituted phenyl.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Particularly preferred mixtures are those in which
n and m independently of one another are a number from 0 to 5, but n and m cannot both be 0,
R
1
is methyl,
R
2
and R
3
, together with the carbon atom connecting them, are a 12-membered ring or, together with the carbon atom connecting them, are a group of the formula (IV),
R
4
and R
5
independently of one another are hydrogen, methyl, acetyl, octyloxy or cyclohexyloxy.
Likewise highly suitable are mixtures in which the substituents R
1
to R
4
in compound I to III have the same definition.
The preparation of compounds of the formula I where R
4
is hydrogen has already been described in German Patent Application No.197 19 944.5. The preparation of the compounds II is described sufficiently in EP-A-0 705 836 and EP-A-0 690 060. The preparation of the compound II where R
4
is H is sufficiently described in EP-A-57 885, Example 20. The preparation of the compound III where R
4
is H is sufficiently described in EP-A-57 885, Example 7.
The mixture M can be prepared simply by combining the compounds I, II and, if desired, Ill in the desired proportion. This procedure can take place, for example, in a powder mixer, in which the substances are mixed in dry form. Additionally or alternatively, the powder mixture can also be homogenized by melting under an inert gas. The mixing operation can also be performed with the aid of a solvent, which is removed from the mixture again by evaporation after the pulverulent components have been thoroughly mixed.
The mixture M of the invention is outstandingly suitable for stabilizing organic material against the action of light, oxygen and heat. It can be added to the organic material to be stabilized prior to, during or after polymerization, in solid form, as a melt, as a solution in solvents or else as a materbatch. The solutions may comprise the mixture M, for example, in 5-80% concentration; a materbatch is particularly appropriate if it comprises the mixture M in a concentration of from 1 to 80%, but preferably 5-30%, with the remainder of the masterbatch comprising a polymer compatible with the polymer to be stabilized. Both the solution and the masterbatch may additionally include other stabilizers or effect substances, examples being UV absorbers, antioxidants, pigments, acid scavengers or fillers. The mixture M is preferably employed such that its concentration in the polymer to be stabilized is from 0.001 to 5% by weight, preferably from 0.02 to 2% by weight, based on the organic material, and it is present either alone or in combination with further additives. The term organic material embraces, for example, precursors for plastics, coating materials, lacquers and oils, but especially the plastics, coating materials, lacquers and oils themselves.
The mixture M is particularly suitable for stabilizing films, fibers, tapes, multifilaments, fabrics, extruded, blow-molded, injection-molded and thermoformed articles, powder coating materials, printing inks, toner inks, photographic material, pigments, wood stains, leathers, architectural paints, protective coatings for steel structures, lubricating oils, machine oils, bitumen or asphalt and for stabilizing compounds which have a tendency to undergo spontaneous polymerization. The mixture M of the invention can also be employed, advantageously, in combinations with further stabilizers. The result of these novel combinations are mixtures having an improved profile of properties with respect to the individual components, such as synergy in the photopro

Affiliated with

Also associated with

Rating

Synergistic stabilizer mixture based on... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synergistic stabilizer mixture based on..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synergistic stabilizer mixture based on... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2533559