Classifications

• • 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

Definitions

• the present invention relates to a method for stabilization of norbornenes, particularly alkenylnorbornenes and alkylidenenorbornenes.
• norbornenes are very useful as one of the termonomers in the production of elastomers with ethylene and propylene (hereinafter referred to as EPDM).
• EPDM ethylene and propylene
• They are sensitive to air, metal oxides and the like and are apt to form rubbery materials on storage, whose presence is unfavorable, when the monomers are used for the production of terpolymer elastomers.
• X and X are each alkylidene having 1 to 6 carbon atoms, cycloalkylidene having 3 to 6 carbon atoms, thio, sulfinyl or sulfonyl, R R R R R R R and R are each hydrogen, alkyl having 1 to 9 carbon atoms or cycloalkyl having 3 to 6 carbon atoms and R R10, R R R R and R are each hydrogen, alkyl having 1 to 9 carbon atoms or phenyl into a norbornene selected from the group consisting of alkenylnobornenes alkylidenenorbornenes.
• alkenylnorbornenes of the formula:
• R R R and R are each hydrogen or alkyl having 1 to 6 carbon atoms and alkylidenenorbornenes of the formula:
• R R and R are each hydrogen or alkyl having 1 to 6 carbon atoms.
• alkenylnorbornenes [A] are as follows:
• alkylidenenorbornenes [B] are as follows:
• the preferred ones are those wherein the substituents on the naphthalene ring represented by the symbols R to R are methyl, ethyl, propyl, isopropyl, butyl, sec.-btuyl, t-butyl, pentyl, isopentyl and/ or phenyl.
• the concentration of the stabilizer, i.e. the phenol [I], [II] or [III], to be incorporated into the norbornene may be usually from about 20 p.p.m. to about 3000 p.p.m. or more.
• the preferred concentration is from 20 ppm. to 500 p.p.m. by weight, since at such concentrations the stabilizer need not be removed prior to use of the norbornene.
• EXAMPLE 1 The desired quantity of stabilizer was added to freshly distilled 5-ethylidene-2-norbornene and charged in a glass ampoule. The ampoule without sealing was placed in an oil bath maintained at 54 C. After the elapse of a certain period of time, the ampoule was taken out from the oil bath and allowed to be cooled. S-Ethylidene-Z-norbornene was evaporated in vacuo, and the residual rubbery material was weighed. The results are shown in Table 1, compared with the results of the blank test Without the addition of any stabilizer.
• EXAMPLE 8 buy p
• the stabilization EXAMPLE 4 effect of the phenol as shown in Table 8 on 5-vinyl-2- norbornene was tested.
• the results are shown in Table 8,
• the stjablhzatloP 15 compared with that in case of using 2-naphthol and that effect of the phenol as shown in Table 4 on 5-isop1'opyl1- in case of the blank test dene-Z-norbornene was tested.
• the results are shown in TABLE 8 Table 4, compared with that in case of the blank test.
• a method for stabilization of norbornenes which comprises incorporating at least one phenol of either one of the formulae:
• alkenylnorbornenes are those of the formula:
• alkylidenenorbornenes are those of the formula:
• R R and R are each hydrogen or alkyl having 1 to 6 carbon atoms.
• 4,4-methylenebis (3 ,5 -di-t-butylphenol) 8 4,4'-methylenebis 3 -methyl-5-t-butylphenol 2,2'-methylenebisphenol, 2,2'-isopropylidenebisphenol, 2,2'-thiobisphenol, 2,2'-methylenebis(4-t-butylphenol), 2,2'-thiobis(4-t-octylpheno1), 2,2'-methylenebis (4-methyl-6-t-butylphenol 2,2-thiobis(4 t-butyl-6-methylphenol), 2,2-methylenebis (4,6-di-t-butylphenol) 2,2'-sulfonebis(4-t-butyl-6-methylphenol), and 2,2'-butylidenebis-( 4-t-butyl-6-methylphenol 7.
• phenol selected from the group consisting of l-naphthol, 2-methyl-1-naphthol, 3-methyl-1-naphthol, 4-methyl-l-naphthol, 5-methyl-1-naphthol, 7-methyl-1-naphthol, 4-methyl-3-phenyl-1-naphthol, 2-ethyl-1-naphthol, 4-ethyl-1-naphthol, 5-ethyl-4-methyl-l-naphthol, 7-ethyl-4-methyl-l-naphthol, 2,4-dimethyl-1-naphthol, 2,7-dimethyl-1-naphthol, 3,4-dimethyl-1-naphthol, 5,7-dimethyl-1-naphthol, 5,8-dimethyl-1-naphthol, 2,4-diethy1-1-naphthol
• R11 is wherein R R R and R are each hydrogen or alkyl having 1 to 6 carbon atoms.
• a composition of matter in accordance with claim 8, wherein the stabilizing amount of phenol in said composition is from 20 p.p.m. to 500 p.p.m.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Analytical Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Water Supply & Treatment (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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• 1972
  • 1972-01-27 JP JP47010383A patent/JPS5235666B2/ja not_active Expired
• 1973
  • 1973-01-23 NL NLAANVRAGE7300966,A patent/NL173392C/xx not_active IP Right Cessation
  • 1973-01-25 GB GB391073A patent/GB1403455A/en not_active Expired
  • 1973-01-25 GB GB44875A patent/GB1403456A/en not_active Expired
  • 1973-01-26 DE DE2303883A patent/DE2303883C3/de not_active Expired
  • 1973-01-26 FR FR7302885A patent/FR2169351B1/fr not_active Expired
  • 1973-01-26 US US00327125A patent/US3830860A/en not_active Expired - Lifetime
  • 1973-01-26 IT IT67163/73A patent/IT977687B/it active

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