A synthesis of 5-hydroxycoumarans, 6-hydroxychromanes and their dodecylthiomethylsubstituted derivatives was accomplished based on methylphenols through the intermediate preparation of 2-allyl-4-alkoxyphenols. The sulfur-containing compounds synthesized were shown to be highly efficient as inhibitors of autooxidation of methyl oleate.

Synthesis and antioxidant activity of 5-hydroxycoumarans, 6-hydroxychromanes and sulfur-containing derivatives on their base

Various alkyl-substituted hydroxybenzyl dodecyl sulfides were synthesized, and a comparative study of their antiradical activity in the model reaction of initiated styrene oxidation and the overall inhibiting activity in the thermal autooxidation of white mineral oil was carried out.

Synthesis and investigation of antioxidant properties of alkylated hydroxybenzyl dodecyl sulfides

The instant invention relates to a composition comprising a) an organic material which is susceptible to oxidative, thermal or light-induced degra- dation, and b) at least one compound of the formula (I) wherein the general symbols are as defined in claim 1; especially wherein at least one of the radicals R2, R3 or R4 is is -CH2-CH(CH3)-S(O)p-R12, -CH2-CH2-CH2-S(O)p-R12, -CH2-CH(R11)-CH2-R12 or -CH2-CH=CH-R12, R11 is hydrogen or halogen, R12 is a monovalent perfluorinated alkyl or alkenyl, linear or branched organic radical having four to twenty fully fluorinated carbon atoms; or -CH2CH2(CF2)mCF3, m is 3 to 12, and p is 0, 1 or 2. The compounds of the formula I are useful as reducers of surface energy for organic mat- erials, for example synthetic polymer. Polymers with such a reduced surface energy possess an 'easy-to-clean', 'self-cleaning' 'antisoiling', 'soil-release' 'antigraffiti', 'oil resistance', 'solvent resistance', 'chemical resistance', 'self lubricating', 'scratch resistance', 'low moi- sture absorption', 'dirt pickup resistance', 'slip properties' and 'hydrophobic surface'; and anti-adhesion properties against proteins and against microorganism such as for example bacteria, fungi and algae.

Perfluoroalkyl substituted phenol derivatives as surface modifiers

The invention describes a process for reducing the surface energy of organic materials such as for example increasing the oil and water repellency and stain release of organic materials, which comprises treating the organic material with at least a compound of the formula I wherein the general symbols are as defined in claim 1; especially wherein at least one of the radicals R2, R3 or R4 is -CH(R11)-S(O)p-R12; R11 is hydrogen, C1-C8alkyl, unsubstituted or with C1-C4alkyl substituted phenyl; R12 is a monovalent perfluorinated alkyl or alkenyl, linear or branched organic radical having four to twenty fully fluorinated carbon atoms, and p is 0, 1 or 2.

S-perfluoroalkyl substituted hydroxybenzylthioethers and derivatives as surface modifiers

Catalytic Thioalkylation of Phenols Based on Mannich‐Type Phenol

Alkyl-hydroxybenzylthioethers are efficient storage and processing stabilizers for elastomers and adhesives. Especially alkyl-(2-hydroxybenzyl)thioethers represent an intramolecular combination of a primary and secondary antioxidant, i.e. a phenolic and a thioether moiety in an optimized spatial arrangement. The mechanism of their intramolecular synergism was investigated. The best overall stabilizers are 2,4-bis(alkylthiomethyl)-6-methylphenols, e.g. AOl, in contrast to 2,6-dialkyl-4-alkylthiomethylphenols(B), 4-alkyl-2,6-bis(alkylthiomethyl)phenols C.

Martin Szelagiewicz

Papers

Reactions of Sulfur Containing Phenolic Antioxidants for Elastomers