GB977588A - Substituted triazines, their production and organic compositions stabilised therewith - Google Patents

Substituted triazines, their production and organic compositions stabilised therewith

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Publication number
GB977588A
GB977588A GB7447/63A GB744763A GB977588A GB 977588 A GB977588 A GB 977588A GB 7447/63 A GB7447/63 A GB 7447/63A GB 744763 A GB744763 A GB 744763A GB 977588 A GB977588 A GB 977588A
Authority
GB
United Kingdom
Prior art keywords
oil
bis
triazine
octylthio
phenylene
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
GB7447/63A
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 GB977588A publication Critical patent/GB977588A/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
    • C07—ORGANIC CHEMISTRY
    • 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
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C08K5/378—Thiols containing heterocyclic rings
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    • 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
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    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

The invention relates to substituted triazines of general formula <FORM:0977588/C1/1> wherein R1, R2, R3, and R4 independently represent an alkyl group having from 1-18 carbon atoms. The compounds may be prepared by reacting two moles of the appropriate mercaptan RSH or an alkali metal salt (including NH4+) with one mole of a triazine having reactive groups attached to the carbon atoms e.g. halogen, particularly chlorine, and then reacting the product with an alkali-metal salt of hydroquinone e.g. the sodium salt. In an example 1, 4-phenylene-bis-[2-oxy-4, 6-bis-(n-octylthio)]-1, 3, 5-triazine is prepared by adding sodium hydroquinone to a solution of 2, 4-bis-(n-octylthio)-6-chloro-1, 3, 5-triazine in ethanol, and precipitating the product by the addition of water. The compounds of the invention are used to stabilize against oxidation by air or oxygen at ambient or elevated temperature various organic materials, including polyolefins, aliphatic aldehydes e.g. heptaldehyde and 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; di-isoamyl adipate; triamyl carballylate; penta aerythritol tetracaproate; dipropylene glycol dipelargonate and 1, 5-pentane diol-di-(2-ethyl hexanoate), and also the diesters of fatty acids having from 5 to 15 carbon atoms per acid molecule, by incorporating therein an amount preferably between 0.001% to 5% by weight. Specification 977,589 also is referred to.ALSO:A stabilizer for polymeric hydrocarbons comprises a substituted triazine of the formula <FORM:0977588/C3/1> which may be made according to the methods described in Division C2. The preferred compound is 1, 4-phenylene-bis-[2-oxy-4, 6-bis-(n-octylthio)] 1, 3, 5-triazine; and it may be used in quantities of 0.001 to 5% by weight. It may be added to polyethylene, polypropylene, polystyrene or a copolymer of butadiene with styrene. Specification 977,589 also is referred to.ALSO:A stabilizer for oils and fats comprises a substituted triazine of the formula <FORM:0977588/C4-C5/1> where R1-4 are each independently C1-18 alkyl radicals, which may be made according to the methods described in Division C2. The preferred compound is 1,4-phenylene-bis-[2-oxy-4,6-bis-(n-octylthio)]-1,3,5-triazine, and it may be used in quantities of 0.001 to 5% by weight. It may be added to linseed oil, menhaden oil, cod liver oil, castor oil, olive oil, rapeseed oil, coconut oil, palm oil, corn oil, sesame oil, peanut oil, cotton seed oil, lard, beef tallow, gasolines, natural and synthetic, jet fuel, diesel oil, mineral oil, fuel oil, drying oil, and various types of synthetic ester lubricating oils, several specific esters being mentioned. Specification 977,589 also is referred to.
GB7447/63A 1960-04-12 1961-03-29 Substituted triazines, their production and organic compositions stabilised therewith Expired GB977588A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
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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GB977588A true GB977588A (en) 1964-12-09

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GB977589D Active GB977589A (en) 1960-04-12
GB35885/62A Expired GB922750A (en) 1960-04-12 1961-03-29 Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby
GB11563/61A Expired GB977587A (en) 1960-04-12 1961-03-29 Method of stabilization with a substituted triazine and compositions stabilized therey
GB7447/63A Expired GB977588A (en) 1960-04-12 1961-03-29 Substituted triazines, their production and organic compositions stabilised therewith
GB11564/61A Expired GB922040A (en) 1960-04-12 1961-03-29 Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby

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GB977589D Active GB977589A (en) 1960-04-12
GB35885/62A Expired GB922750A (en) 1960-04-12 1961-03-29 Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby
GB11563/61A Expired GB977587A (en) 1960-04-12 1961-03-29 Method of stabilization with a substituted triazine and compositions stabilized therey

Family Applications After (1)

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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

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BE (1) BE602449A (en)
CH (4) CH446327A (en)
DE (2) DE1470832C3 (en)
GB (5) GB922750A (en)
MY (2) MY6400133A (en)
NL (4) NL124028C (en)
SE (1) SE306424B (en)

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US3462291A (en) * 1966-01-20 1969-08-19 Hercules Inc Stabilization of polypropylene

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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
GB1393551A (en) * 1972-04-21 1975-05-07 Ciba Geigy Ag Piperidine derivatives
NL7511698A (en) * 1975-10-04 1977-04-06 Akzo Nv PROCESS FOR THE PREPARATION OF A NEW ANTI-OXYDANT.
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
JPH06103396B2 (en) * 1985-10-31 1994-12-14 三菱化成株式会社 Electrophotographic photoreceptor
US4794134A (en) * 1987-08-28 1988-12-27 Uniroyal Chemical Company, Inc. Ozone resistant elastomeric articles
US5047530A (en) * 1987-08-28 1991-09-10 Uniroyal Chemical Company, Inc. Arylenediamine substituted triazines
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
US4972010A (en) * 1988-09-21 1990-11-20 Uniroyal Chemical Company, Inc. Substituted triazines
US5120844A (en) * 1988-09-21 1992-06-09 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
US5290460A (en) * 1993-02-22 1994-03-01 Exxon Research & Engineering Co. Lubricant composition containing complexes of alkoxylated amine, trithiocyanuric acid, and adenine
US5275745A (en) * 1993-02-22 1994-01-04 Exxon Research & Engineering Co. Lubricant composition containing alkoxylated amine salt of trithiocyanuric acid
JP4548761B2 (en) 2000-06-15 2010-09-22 富士フイルムホールディングス株式会社 Lubricant composition
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
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) *
NL105044C (en) * 1956-12-14

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462291A (en) * 1966-01-20 1969-08-19 Hercules Inc Stabilization of polypropylene

Also Published As

Publication number Publication date
DE1470832B2 (en) 1975-03-06
CH427791A (en) 1967-01-15
GB922040A (en) 1963-03-27
CH433711A (en) 1967-04-15
MY6400133A (en) 1964-12-31
NL263480A (en)
SE306424B (en) 1968-11-25
DE1470832C3 (en) 1975-11-06
CH446327A (en) 1967-11-15
BE602449A (en)
DE1264051B (en) 1968-03-21
NL126079C (en)
DE1470832A1 (en) 1969-06-04
GB977589A (en)
CH446328A (en) 1967-11-15
NL124028C (en)
GB977587A (en) 1964-12-09
NL263479A (en)
GB922750A (en) 1963-04-03
MY6500001A (en) 1965-12-31

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