GB977587A - Method of stabilization with a substituted triazine and compositions stabilized therey - Google Patents

Method of stabilization with a substituted triazine and compositions stabilized therey

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Publication number
GB977587A
GB977587A GB11563/61A GB1156361A GB977587A GB 977587 A GB977587 A GB 977587A GB 11563/61 A GB11563/61 A GB 11563/61A GB 1156361 A GB1156361 A GB 1156361A GB 977587 A GB977587 A GB 977587A
Authority
GB
United Kingdom
Prior art keywords
alkylhydroxyphenyl
linked
alkyl
represent
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB11563/61A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
JR Geigy AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB977587A publication Critical patent/GB977587A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/20—Use of additives, e.g. for stabilisation
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
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    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

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  • Polymers & Plastics (AREA)
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  • Analytical Chemistry (AREA)
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Abstract

Aliphatic aldehydes (e.g. heptaldehyde) or aliphatic ester lubricants (e.g. dihexyl azelate, di-(2-ethylhexyl) azelate, di-(3,5,5-trimethylhexyl) glutarate, di-(3,5,5-trimethylpentyl) glutarate, di-(2-ethylhexyl) pimelate; di-(2-ethylhexyl) adipate, diisoamyl adipate, trimethyl tricarballylate, pentaerythritol tetracaproate, dipropylene glycol dipelargonate and 1,5-pentanediol di-(2-ethylhexanoate)) are stabilized by incorporating therein (with or without other additives) a compound of the general formula <FORM:0977587/C1/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkylphenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonylalkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y, and Z being bound to the ring carbon atoms by way or <FORM:0977587/C1/2> alkyl) or <FORM:0977587/C1/3> benzyl, and wherein also if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S-, and Z is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom, and if X is alkylhydroxyphenyl linked by -NH-, then Y and Z may both represent chlorine atoms, whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by <FORM:0977587/C1/4> alkanoyl. Substituted triazines.-Most of the compounds of the general formula above, other than those containing an <FORM:0977587/C1/5> alkanoyl linkage, are obtainable as intermediates or final products in the processes set out in Specification 977,589. Similarly prepared, but outside the scope of Specification 977,589 are 6-(p-hydroxyanilino)-2, 4-bis-(phenylthio)-1, 3, 5-triazine, 6-(o-, m- and p-hydroxyanilino)-2,4-bis-(n-octylthio)-1,3,5-triazine, 6-(2-hydroxy-5-phenylanilino)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine, 6-(p-hydroxy-N-methylanilino)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine and 6-(p-hydroxyphenoxy)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine. The <FORM:0977587/C1/6> alkanoyl compounds are prepared by acylation of the corresponding -NH- compounds. When the final product is to contain also one or more -NH- linkages, the acylation is performed on a compound of the general formula <FORM:0977587/C1/7> (wherein R represents an alkylhydroxyphenylamino group), whereafter the two chlorine atoms are replaced by the other desired substituents.ALSO:Polypropylene and polyethylene, which are of high, medium or low density; polystyrene and copolymers of styrene with copolymerizable monomers, e.g. high impact polystyrene containing copolymers of butadiene and styrene, are stabilized by incorporating therein (with or without other additives) a compound of the general formula <FORM:0977587/C3/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkylphenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonyl alkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y and Z being bound to the ring carbon atoms by way of -S-, -O-, -NH-, <FORM:0977587/C3/2> (C1- 6 alkyl) or <FORM:0977587/C3/3> benzyl, and wherein also if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S- and X is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom, and if X is alkylhydroxyphenyl linked by -NH-, then Y and Z may both represent chlorine atoms, whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by <FORM:0977587/C3/4> alkanoyl. In an example, unstabilized polypropylene powder, low pressure polyethylene and high impact polystyrene are stabilized with 6-(4-hydroxy-3, 5-di-t-butylanilino)-2, 4-bis-(n-octylthio)-1, 3, 5-triazine Specification 977,589 is referred to.ALSO:Fats and oils of animal and vegetable origin including linseed oil, menhaden oil, cod liver oil, castor oil, olive oil, rapeseed oil, coconut oil, palm oil, sesame oil, peanut oil, cottonseed oil, fat, lard and beef tallow; hydrocarbons both saturated and unsaturated, for example, petrol, natural or synthetic, jet fuel, diesel loil, mineral oil and fuel oil; aliphatic ester lubricants (of various types, many of which are specified), and hydrocarbon waxes, are stabilized by incorporating (with or without other additives) a compound of the general formula <FORM:0977587/C4-C5/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkyl phenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonylalkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y and Z being bound to the ring carbon atoms by way of -S-, -O-, -NH-, <FORM:0977587/C4-C5/2> (C1-6 alkyl) or <FORM:0977587/C4-C5/3> benzyl and wherein also, if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S- and Z is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom and if X is alkylhydroxyphenyl linked by -NH-, then Y and Z may both represent chlorine atoms whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by N-alkanoyl. In examples, a white mineral oil, a Texas cracked petrol with no additives, lard, a high-temperature lubricant comprising diisoamyl adipate, and paraffin wax are stabilized by addition of 6-(4-hydroxy-3,5-di-t-butylanilino) - 2,4 - bis - (n - octylthio)-1,3,5-triazine. Specification 977,589 is referred to.ALSO:Butter is stabilized by incorporating therein (with or without other additives) a compound of the general formula <FORM:0977587/A1-A3/1> wherein X and Y each independently represent an alkyl, cycloalkyl, phenyl, alkylphenyl, alkylhydroxyphenyl, alkylhydroxybenzyl, cyanoalkyl, alkylmercaptoalkyl, alkoxycarbonylalkyl or alkoxycarbonylaryl group, Z represents a hydroxyphenyl, alkylhydroxyphenyl, phenylhydroxyphenyl or alkylhydroxybenzyl group, X, Y and Z being bound to the ring carbon atom, by way of -S-, -O-, -NH-, -N1-(C1-6 alkyl) or -N1- benzyl and wherein also, if Y is alkylhydroxyphenyl linked by -NH- or alkyl linked by -S- and Z is alkylhydroxyphenyl linked by -NH-, then X may also represent a chlorine atom and if X is alkylhydroxyphenyl linked by -NH- then Y and Z may both represent chlorine atoms whilst if both X and Y are alkyl groups linked in the stated manner, then Z may represent an alkylhydroxyphenyl group linked by -N1-alkanoyl. Specification 977,589 is referred to.
GB11563/61A 1960-04-12 1961-03-29 Method of stabilization with a substituted triazine and compositions stabilized therey Expired GB977587A (en)

Applications Claiming Priority (4)

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US2160460A 1960-04-12 1960-04-12
US4715960A 1960-08-03 1960-08-03
US8752161A 1961-02-21 1961-02-21
US8752061A 1961-02-21 1961-02-21

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GB11564/61A Expired GB922040A (en) 1960-04-12 1961-03-29 Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby
GB7447/63A Expired GB977588A (en) 1960-04-12 1961-03-29 Substituted triazines, their production and organic compositions stabilised therewith
GB11563/61A Expired GB977587A (en) 1960-04-12 1961-03-29 Method of stabilization with a substituted triazine and compositions stabilized therey
GB35885/62A Expired GB922750A (en) 1960-04-12 1961-03-29 Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby

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GB7447/63A Expired GB977588A (en) 1960-04-12 1961-03-29 Substituted triazines, their production and organic compositions stabilised therewith

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CH (4) CH433711A (en)
DE (2) DE1264051B (en)
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Cited By (4)

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Publication number Priority date Publication date Assignee Title
DE2319816A1 (en) * 1972-04-21 1973-10-31 Ciba Geigy Ag PIPERIDINE DERIVATIVES
US4104250A (en) * 1976-08-11 1978-08-01 Borg-Warner Corporation Flame-retardant polymers with 1,3,5-triazines having halo- and halo-aryl substitutents
EP1164182A1 (en) * 2000-06-15 2001-12-19 Fuji Photo Film Co., Ltd. Lubricant composition
EP1266950A1 (en) * 2001-06-11 2002-12-18 Fuji Photo Film Co., Ltd. Lubricant composition containing a triazine molecular complex compound

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US3462291A (en) * 1966-01-20 1969-08-19 Hercules Inc Stabilization of polypropylene
US3531483A (en) * 1968-10-25 1970-09-29 Goodrich Co B F Hydroxyphenylalkyleneyl isocyanurates
US3678047A (en) * 1970-04-27 1972-07-18 Goodrich Co B F Alkylhydroxyphenylcarboalkoxy-substituted isocyanurates
BE791173A (en) * 1971-11-10 1973-05-09 Degussa S-TRIAZINE DERIVATIVES CONTAINING NAPHTYLAMINO GROUPS AND THEIR USE
BE791368A (en) * 1971-11-16 1973-05-14 American Cyanamid Co DERIVATIVES OF TRIAZINE AND THEIR USE AS ANTIOXIDANTS
NL7511698A (en) * 1975-10-04 1977-04-06 Akzo Nv PROCESS FOR THE PREPARATION OF A NEW ANTI-OXYDANT.
JPH06103396B2 (en) * 1985-10-31 1994-12-14 三菱化成株式会社 Electrophotographic photoreceptor
US5047530A (en) * 1987-08-28 1991-09-10 Uniroyal Chemical Company, Inc. Arylenediamine substituted triazines
US4794134A (en) * 1987-08-28 1988-12-27 Uniroyal Chemical Company, Inc. Ozone resistant elastomeric articles
US4794135A (en) * 1987-08-28 1988-12-27 Uniroyal Chemical Company, Inc. Arylenediamine substituted triazines
US4839188A (en) * 1988-05-27 1989-06-13 Uniroyal Chemical Company, Inc. Stabilized fat compositions
US5120844A (en) * 1988-09-21 1992-06-09 Uniroyal Chemical Company, Inc. Substituted triazines
US4972010A (en) * 1988-09-21 1990-11-20 Uniroyal Chemical Company, Inc. Substituted triazines
US5208280A (en) * 1989-10-13 1993-05-04 Uniroyal Chemical Company, Inc. Elastomers and tire with N-alkyl-p-quinonediimino triazine stabilizers
US5118807A (en) * 1989-10-13 1992-06-02 Uniroyal Chemical Company, Inc. N-alkyl-p-quinonediimino triazine compounds
US5126385A (en) * 1990-03-20 1992-06-30 Uniroyal Chemical Company, Inc. Chloropyrimidines and chlorotriazines as rubber-to-metal adhesion promoters
US5264496A (en) * 1991-07-05 1993-11-23 General Electric Company Method for preparing reactive triazine-capped aromatic polymers, and intermediates for use therein
US5275745A (en) * 1993-02-22 1994-01-04 Exxon Research & Engineering Co. Lubricant composition containing alkoxylated amine salt of trithiocyanuric acid
US5290460A (en) * 1993-02-22 1994-03-01 Exxon Research & Engineering Co. Lubricant composition containing complexes of alkoxylated amine, trithiocyanuric acid, and adenine
CN109651280A (en) * 2019-02-01 2019-04-19 浙江扬帆新材料股份有限公司 A kind of synthetic method of antioxidant 565
CN115109466B (en) * 2022-07-28 2023-03-21 佛山市帆思科材料技术有限公司 Anti-aging water-based color ink-jet printing ink product and manufacturing method thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE583316A (en) *
NL223154A (en) * 1956-12-14

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2319816A1 (en) * 1972-04-21 1973-10-31 Ciba Geigy Ag PIPERIDINE DERIVATIVES
US4104250A (en) * 1976-08-11 1978-08-01 Borg-Warner Corporation Flame-retardant polymers with 1,3,5-triazines having halo- and halo-aryl substitutents
EP1164182A1 (en) * 2000-06-15 2001-12-19 Fuji Photo Film Co., Ltd. Lubricant composition
US6528460B2 (en) 2000-06-15 2003-03-04 Fuji Photo Film Co., Ltd. Lubricant composition
EP1266950A1 (en) * 2001-06-11 2002-12-18 Fuji Photo Film Co., Ltd. Lubricant composition containing a triazine molecular complex compound
US7018960B2 (en) 2001-06-11 2006-03-28 Fuji Photo Film Co., Ltd. Lubricant composition, method for using and preparing thereof and molecular complex compound used for the same

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NL263479A (en)
CH427791A (en) 1967-01-15
GB977589A (en)
NL263480A (en)
SE306424B (en) 1968-11-25
CH446327A (en) 1967-11-15
DE1470832C3 (en) 1975-11-06
GB922040A (en) 1963-03-27
BE602449A (en)
DE1470832A1 (en) 1969-06-04
DE1264051B (en) 1968-03-21
CH446328A (en) 1967-11-15
GB922750A (en) 1963-04-03
MY6500001A (en) 1965-12-31
MY6400133A (en) 1964-12-31
GB977588A (en) 1964-12-09
NL124028C (en)
CH433711A (en) 1967-04-15
DE1470832B2 (en) 1975-03-06

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