Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
  • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
  • C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/37—Thiols
  • C08K5/372—Sulfides, e.g. R-(S)x-R'
  • C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
  • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom

Definitions

• the invention concerns new carboxylic acid amides of the formula wherein M denotes a divalent bridge member of the series S, -S--A-S and S-CH CH (OCH CH S, A denotes an alkylene residue containing one to 18 carbon atoms, p denotes an integer from one to three, R denotes an alkyl group and R denotes alkyl or hydrogen.
• R1 The subject of the invention is the new carboxylic acid H0 OA Ha1 amides of formula R2 R1 R1 HO -NH-C OA- M AC OHN ()H L l wherein M denotes a divalent bridge member of the series with about one mol of a mercaptan of formula 8-, SAS- and SCl-l CH -(O-CH CH S, A denotes an alkylene residue containing 1 to 18 carbon (6) r j atoms, p denotes an integer from one to three, R, denotes an T alkyl group with one to eight carbon atoms and R denotes hydrogen or an alkyl group with one to eight ca b atoms in the form of its alkali salt, with R,, R A and M having the Here the total number of carbon atoms for all A members abovememioned Significance and Hal representing a halogen normally does not amount to
• M denotes a divalent bridge member S, S (8) I 1 (Cl-l S or SCl-l Cl-I --OCH CH -S-, q T T denotes an integer from one to six, n denotes an integer from I one to 12, R, denotes an alkyl group with one to eight carbon m the form of f j i R2 n and moms R2 denotes hydrogen or an alkyl group with one to 40 mg the abovementloned significance and Hal representing a eight carbon atoms and R denotes hydrogen or an alkyl halogen atom group containing one to four carbon atoms.
• M denotes a divalent bridge member -S or S (CH )
• S q denotes an integer from 1 to 6
• n denotes an in a solvent which is inert towards the reagents (for example 5 5 alcohols or hydrocarbons).
• R denotes an alkyl group with one to
• the alkali salts of the dithiols can be manufactured in the eight carbon atoms and R denotes hydrogen or an alkyl group presence of a solvent by using the alkali metal, or through the with one to eight carbon atoms (with the alkyl group for R, use of the stoichiometric amount of an alkali alcoholate.
• the and R in particular containing one to four carbon atoms), and compounds of formula (5) required as starting substances are furthermore compounds of formula obtained by the reaction, which is in itself known, of acid haa Ra 1-10 NH-o0-cmmm m 0Emu-004m OH wherein M, denotes a divalent bridge member S- or S lides, preferably acid chlorides, of formula (Cl-l S, q denotes an integer from one to six, m denotes an integer from one to four, and R denotes a branched alkyl Hal-A-CO-l-lal 10 group containing one to four carbon atoms.
• the compounds defined above can be manufactured analogously to procedures which are in themselves known.
• the compounds according to formula l) and analogously, those of the subordinate formulas can appropriately be obtained by reacting about two mols of a compound of formula R2 wherein A, Hal, R and R have the abovementioned significance. This reaction is carried out in the presence of a solvent which is inert towards the reagents, with the corresponding hydrogen halide acid being split off.
• the resulting hydrogen halide acid can be removed from the reaction mixture by sucking-off, or be bonded by adding a hydrogen halide acceptor, (for example a tertiary amine).
• acrylic and methacrylic acid derivatives for example acrylic acid alkyl esters, acrylamides and acrylonitrile; polyamides, for example from e-caprolactam or from adipic acid and a diamine; polyesters such as polyterephthalic acid glycol ester; natural and synthetic rubbers; lubricating oils; petrol; vegetashows the following data:
• the compounds defined above are of preferred importance as stabilizers against oxidative influences in the case of HO NH O O CH2C1 polymerization products of a-olefines, that is to say in the case 2 5 5 of homopolymers and copolymers of a-olefines such as 7 preferably ethylene or propylene, and also in the case of substrates which predominantly contain homopolymersv or copolymers of a-olefines.
• antioxidants small amounts of compounds of formula l that is to say about 0.01 to two percent relative to the amount of the substrate to be protected, in general suffice.
• the antioxidants can for example be incorporated into the materials to be protected directly, that is to say by themselves, or together with other additives such as plasticizers, pigments, light protection agents or optical brighteners, and/or with the aid of solvents.
• the antioxidative effect of the compounds of formula (1) also manifests itself in the light exposure test, in that these compounds are able to prevent or greatly to reduce oxidative processes induced by the action of light, for example the yellowing of polyethylene.
• EXAMPLE 1 1.6 g of crystalline 61 percent strength sodium sulphide are dissolved in 100 ml of methanol. 7.425 g of the compound of formula used as the starting material is manufactured as follows: 23.5 g
• the compounds of formula are obtained from the dried methylene chloride extracts.
• M denotes a divalent bridge member of the series
• SAS- and S-CH -CH (OCH -CH ),,S-, A denotes an alkylene containing one to 18 carbon atoms
• p denotes an integer from one to three
• R denotes an alkyl group with one to eight carbon atoms
• R denotes Peroxide number milliequivalents of peroxidic oxygen)/kg 3 5 hydrogen or an alkyl group with one to eight carbon atoms.
• a carboxylic acid amide according to claim 1 which corresponds to the formula Peroxide number Olive oil, without additive, freshly distilled 0 Olive oil, without additive, oxidized for 20 minutes 334 Olive oil with 0.2 of the compound l3 (partially dissolved) (Example I I28 Olive oil with 0.2 of the compound 26 (Example 2) 78 an integer from one to six, n denotes an integer from one to 12, R, denotes an alkyl group with one to eight carbon atoms, R denotes hydrogen or an alkyl group with l to eight carbon atoms and R denotes hydrogen or an alkyl group containing one to four carbon atoms; R and R cannot simultaneously be different from hydrogen.
• a carboxylic acid amide according to claim 1 which corresponds to the formula 3 Olive oil with 0.2 of 2,6di-tert.butylwherein M, denotes a divalent bridge member -S(CH 4-methylphenol l22 S, q denotes an integer from one to six, n denotes an integer Olive oil with 0.2 of methylene-bis-(3- methyl-4-hydroxy-S-terLbUtylbenZene 137 from one to 12, R, denotes an alkyl group with one to eight carbon atoms and R denotes hydrogen or an alkyl group with to eight carbon atoms.
• M denotes a divalent bridge member -S(CH 4-methylphenol l22 S
• q denotes an integer from one to six
• n denotes an integer Olive oil with 0.2 of methylene-bis-(3- methyl-4-hydroxy-S-terLbUtylbenZene 137 from one to 12
• R denotes an al
• a carboxylic acid amide according to claim 1 which cor- A mixture of 100 g of polyethylene powder (Microthene responds to the formula H0- NIICOC "Hz” Mi C l'iH2n "C OHN -OH I I L J l l R: R2 R1 R2 722, USl) and 0.2 g of one of the compounds mentioned in Table 6 is aged at 85 C for l6 hours in a circulating air oven.
• melt index is determined according to ASTM from one to four and R denotes a branched alkyl group con- Specification D-l238-62-T.
• the melt index equals the amount of polyethylene, in grams, which has flowed in 10 minutes through a standard die, and represents a measure of taining up to four carbon atoms.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Materials Engineering (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Anti-Oxidant Or Stabilizer Compositions (AREA)
• Fats And Perfumes (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4434515

Family Applications (1)

Country Status (9)

Cited By (8)

Families Citing this family (5)

• 1968
  • 1968-12-13 CH CH1866468A patent/CH506323A/de not_active IP Right Cessation
• 1969
  • 1969-12-03 IL IL33479A patent/IL33479A0/xx unknown
  • 1969-12-04 US US882302A patent/US3676494A/en not_active Expired - Lifetime
  • 1969-12-04 GB GB59389/69A patent/GB1241617A/en not_active Expired
  • 1969-12-05 DE DE19691961177 patent/DE1961177A1/de active Pending
  • 1969-12-10 FR FR6942765A patent/FR2026064A1/fr not_active Withdrawn
  • 1969-12-12 BE BE743093D patent/BE743093A/xx unknown
  • 1969-12-12 NL NL6918693A patent/NL6918693A/xx unknown
  • 1969-12-13 JP JP44099815A patent/JPS4934911B1/ja active Pending

Non-Patent Citations (1)

Also Published As

Similar Documents