Compounds having a stabilizing effect, method for producing said compounds, composition containing said stabilizing compounds, and uses of the compounds
The invention relates to compounds of a new type which have a stabilizing effect and in particular provide stabilization with respect to oxidative thermal and/or actinic decomposition of or damage to organic materials. The compounds are represented by general formula I specified below. The invention further relates to a method for producing such compounds, to compositions containing said compound, to a method for stabilizing organic compounds by means of the stabilizing compounds, and to the use of the stabilizing compounds to stabilize organic materials.
1. A compound selected from the group consisting of
wherein Z is
and wherein the variables B, D, R, b, x, y, and z each has the following definition independently of one another:
B O or NH;
D a linear or branched aliphatic residue having 1 to 12 carbon atoms;
R a residue having at least one sterically hindered hydroxyphenyl residue;
b 0 or 1;
x 0 to 12;
y 1 to 4; and
z 2, 3, or 4,
wherein the at least one sterically hindered hydroxyphenyl residue has the formula:
wherein
E is the same or different on every occurrence and represents a linear aliphatic, branched aliphatic, or cycloaliphatic alkyl residue having 1 to 18 carbon atoms, an aromatic residue having 6 to 36 carbon atoms, or hydrogen;
a is 1 or 0; and
c is 0, 1, 2, 3, or 4.
2. The compound of claim 1 , wherein variables x and y have the following meaning respectively independently of one another:
x 0 or 1;
y 1 or 2.
3. The compound of claim 1 , wherein D is —CH 2− .
4. The compound of claim 1 , which is selected from the group consisting of the following compounds:
wherein the residue Y has the following meaning on every occurrence:
wherein in the above residues, the tBu residue can also be substituted in full or in part by a methyl group.
5. A method of preparing a compound of claim 1 , wherein a compound selected from the group consisting of the following compounds
wherein Z is:
wherein the variables B, b, x each has the following definition independently of one another:
B O or NH;
b 0 or 1;
x 0 to 12; and
z 2 3 or 4;
is reacted with a thiol of the following formula:
wherein the variables D, R, y each has the following definition independently of one another:
D a linear or branched aliphatic residue having 1 to 12 carbon atoms;
R a residue having at least one sterically hindered hydroxyphenyl residue; and
y 1 to 4; and
wherein the at least one sterically hindered hydroxyphenyl residue has the formula:
wherein
E is the same or different on every occurrence and represents a linearly aliphatic, branched aliphatic, or cycloaliphatic alkyl residue having 1 to 18 carbon atoms or an aromatic residue having 6 to 36 carbon atom or hydrogen;
a is 1 or 0; and
c is 0, 1, 2, 3, or 4.
6. The method of claim 5 , wherein the reaction of the compound with the thiol is carried out with an excess of the thiol with respect to the unsaturated function of the compound.
7. A composition comprising at least one organic component to be stabilized and at least one compound in accordance with claim 1 .
8. The composition of claim 7 , wherein the component to be stabilized is selected from the group consisting of plastics, oils, lubricants, and fats.
9. The composition of claim 7 , which comprises:
95.00 to 99.99 wt% of at least one component to be stabilized and
0.01 to 5.00 wt% of the at least one compound.
10. The composition of claim 7 , which additionally includes at least one additive selected from the group consisting of UV absorbers, light stabilizers, stabilizers, antioxidants, hydroxyl amines, benzofurans, metal deactivators, filler deactivators, antiozonants, nucleation agents, impact strength improvers, plasticizers, lubricants, rheology modifiers, thixotropic agents, chain extenders, processing aids, demolding aids, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anti-crosslinking agents, hydrophilization agents, hydrophobization agents, bonding agents, dispersion agents, degradation additives, defoaming aids, odor traps, marking agents, antifogging agents, fillers, and reinforcements.
11. The composition of claim 7 , which additionally includes at least one additive selected from the group consisting of phosphites, phosphonites, hydroxylamines, and nitrons.
12. A method of stabilizing an organic component to be stabilized, the method comprising mixing with, or working into, at least one compound of claim 1 with the organic component to be stabilized.
13. The method of claim 12 , wherein the organic component is stabilized with respect to oxidative, thermal, or actinic degradation or damage.