SU413673A3 - METHOD OF OBTAINING THE DIAGNOBAS-SCHAVELEVOKYKOTLOTY12 - Google Patents

METHOD OF OBTAINING THE DIAGNOBAS-SCHAVELEVOKYKOTLOTY12

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Publication number
SU413673A3
SU413673A3 SU1653203A SU1653203A SU413673A3 SU 413673 A3 SU413673 A3 SU 413673A3 SU 1653203 A SU1653203 A SU 1653203A SU 1653203 A SU1653203 A SU 1653203A SU 413673 A3 SU413673 A3 SU 413673A3
Authority
SU
USSR - Soviet Union
Prior art keywords
formula
diagnobas
obtaining
compound
diamide
Prior art date
Application number
SU1653203A
Other languages
Russian (ru)
Original Assignee
Иностранцы Макс Динненбергер , Ханс Рудольф Биланд
Иностранна Циба Гейги
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 Иностранцы Макс Динненбергер , Ханс Рудольф Биланд, Иностранна Циба Гейги filed Critical Иностранцы Макс Динненбергер , Ханс Рудольф Биланд
Application granted granted Critical
Publication of SU413673A3 publication Critical patent/SU413673A3/en

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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
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • C09K15/22—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing an amide or imide moiety
    • 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
    • C08K5/20—Carboxylic acid amides
    • 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
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
    • C11B5/0057—Amides or imides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Description

Изобретение относитс  к области получени  новых нроизводных оксамидов, в частности, к способу получени  диамида быс-щавелевой кислоты, который может быть иснользован в качестве антиокислител  дл  полимерных материалов , например, поли-а-олефинов.The invention relates to the field of producing new oxamide derivatives, in particular, to a method for producing oxalic oxamide diamide, which can be used as an antioxidant for polymeric materials, for example poly-a-olefins.

Известен способ получени  диамида бисщавелевой кислоты путем обработки слол ного эфира н авелевой кислоты диамином.A known method for the preparation of bis-oxalic acid diamide by treating the ternary halide ester with a diamine.

Однако полученный по известному способу диамид б«с-н1,авелевой кислоты обладает заflCHsV , ,, ,However, obtained by a known method, diamide b "C-N1, maximic acid has flac CHsV ,, ,,

IV; ,:IV; ,:

HO-f V-NIl-C .ШrHO-f V-NIl-C .Shr

(СН-Оз (CH-Oz

где R - алкиленостаток с 5-18 атомами углерода .where R is alkylene with 5-18 carbon atoms.

Способ получени  соединени  формулы (1), основанный на известной реакции, состоит в том, что 2 моль соединени  формулыThe method of preparing the compound of formula (1), based on the known reaction, is that 2 mol of the compound of formula

НО 1НзС )зBUT 1NzS) s

подвергают взаимодействию с 1 моль соединени  формулы X-R-Xreacted with 1 mole of the compound of the formula X-R-X

щитным свонством против воздействи  ультрафиолетовых лучей, НС  вл  сь антиокислителем .protective against UV exposure, NS is an antioxidant.

При да.тьнейших исследовани х было найдено , что определенна  группа новых диампдов быс-пдавелевой кислоты обладает свойством антиокислител , которое отсутствует у соединеннй аналогичной структуры.In the course of our most recent studies, it was found that a certain group of new dipads with byd-surfactant acid has an antioxidant property, which is not present in the United States with a similar structure.

Новый диамид оис-щавелевой кислоты имеет общую формулуNew diamide of oxalic acid has the general formula

О ОOh oh

/ /

Н- С - С -HN -/ Н- С - С -HN - /

где X и X - различны where X and X are different

ооозначают -Nn, или -Н-СО-СО-Y,oo -Nn or -N-CO-CO-Y,

где Y- -С1, -ОН или алкоксигрунна с 1 - 12 атомами углерода,where Y- -C1, -OH or alkoxygrunn with 1 to 12 carbon atoms,

R - имеет указанное значение, с последующим выделеннем целевого продукта известным приемом.R - has the specified value, with the subsequent selection of the target product by a known technique.

Процесс провод т при О-250°С в среде инертного органического растворител , а в соответствующем случае в присутствии катализатора конденсации, например триэтаноламина , пиридина.The process is carried out at about 250 ° C in an inert organic solvent, and in the appropriate case in the presence of a condensation catalyst, for example, triethanolamine, pyridine.

Полученные но предложенному способу диамиды б/гс-щавелевой кислоты могут быть использованы дл  стабилизации органическихObtained but proposed method diamides b / gc-oxalic acid can be used to stabilize organic

материалов против разлол ени  их окислением . Пример 1. 6,4 г соединени  формулыanti-oxidation materials. Example 1. 6.4 g of compound of formula

(CHslsC(CHslsC

О оOh oh

V-NH-C-C-OCgHsV-NH-C-C-OCgHs

(сн,),г(sn,), g

(сНз)зС(сНз) ЗС

НО -/V-UH- с - с - NH- (СН г |б - NH- С - С ОНBUT - / V-UH-c-c-NH- (CH g | b-NH-C-C HE

(СНз)зС , С(СНз)з(SNZ) zS, S (SNZ) s

выдел ют в виде бесцветных кристаллов. Вы- Ю этанола точка плавлени  230-231°С. ход xl г.Аналогично получают следуюище соединеПосле трехкратной перекристаллизации из ии  формулы (I):isolated as colorless crystals. You ethanol melting point 230-231 ° C. move xl g. Similarly, the following compound is obtained: After three times recrystallization from AI of formula (I):

(полученного взаимодействием 1-амино-3,5-дитрег-бутил-4-оксибензола с хлоридом сложного моноэтилового эфира шавелевой кислоты в бензоле в присутствии пиримидина как акцептора НС1; точка плавлени  139-140°С), перемешивают в 60 см этанола с 1,2 г .1,6-диаминогексана в течение 3 час с обратным холодильником . Затем охлаждают до 10°С. Продукт фор.мулы(obtained by reacting 1-amino-3,5-ditreg-butyl-4-hydroxybenzene with shavelic acid monoethyl chloride in benzene in the presence of pyrimidine as an HC1 acceptor; melting point 139-140 ° C), stirred in 60 cm of ethanol with 1 , 2 g .1,6-diaminohexane for 3 hours under reflux. Then cooled to 10 ° C. Formula Product

SU1653203A 1970-04-29 1971-04-28 METHOD OF OBTAINING THE DIAGNOBAS-SCHAVELEVOKYKOTLOTY12 SU413673A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH646570A CH534539A (en) 1970-04-29 1970-04-29 Use of bis-oxalic acid diamides as antioxidants for organic materials

Publications (1)

Publication Number Publication Date
SU413673A3 true SU413673A3 (en) 1974-01-30

Family

ID=4310055

Family Applications (1)

Application Number Title Priority Date Filing Date
SU1653203A SU413673A3 (en) 1970-04-29 1971-04-28 METHOD OF OBTAINING THE DIAGNOBAS-SCHAVELEVOKYKOTLOTY12

Country Status (8)

Country Link
AT (1) AT309826B (en)
CA (1) CA924327A (en)
CH (1) CH534539A (en)
DE (1) DE2120954A1 (en)
FR (1) FR2090870A5 (en)
GB (1) GB1325944A (en)
NL (1) NL7105824A (en)
SU (1) SU413673A3 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104287A (en) * 1973-02-24 1978-08-01 Basf Aktiengesellschaft 4-M,M'-Di-t-butyl-p-hydroxyphenyl) butyl-2 compounds
EP0002616B1 (en) * 1977-12-21 1983-03-30 Uniroyal, Inc. Oxamide derivatives, their use in stabilizing organic materials and stabilized organic materials containing the said oxamide derivatives
US8680186B2 (en) 2011-07-29 2014-03-25 Rohm And Haas Company Semi-crystalline polyolefin composition, method of producing the same, and articles made therefrom

Also Published As

Publication number Publication date
DE2120954A1 (en) 1971-11-18
GB1325944A (en) 1973-08-08
FR2090870A5 (en) 1972-01-14
CA924327A (en) 1973-04-10
CH534539A (en) 1973-03-15
NL7105824A (en) 1971-11-02
AT309826B (en) 1973-09-10

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