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Monoester compound of 2,2-alkylidene bis(4,6-di-substituted phenol)

Assignee: Asahi Kasei Corp
•
Filing: 1981-11-04
•
Granted: 1982-12-21
•
Expires: 2001-11-04
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Abstract

Abstract A monoester compound of a 2,2'-alkylidene bis(4,6-di-substituted phenol) useful as an antioxidant in synthetic polymers having good resistant to oxides of nitrogen fumes, represented by the formula (I), ##STR1## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group; R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a C 2-4 alkenyl group, a phenyl group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di- C 1-4 alkyl-substituted hydroxyphenyl group, a styryl group, a benzyl group or a pyridyl group, and a method of preparing such a monoester compound.

Inventors

  • 👤 Akihiko Yosizato
  • 👤 Yoshinori Morifuji
  • 👤 Kunio Kondo
  • 👤 Masatsugu Yoshino

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 19:59
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/10; C08K5/101; C08K5/105; C08K5/107; C09; C09K; C09K15/00; C09K15/04; C09K15/06; C09K15/08

Claims Analysis

Total Claims: 50
Claim 1
Independent Claim 115 words
A compound of the formula, ##STR26## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group; R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a phenyl group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di-C 1-4 alkyl-substituted hydroxyphenyl group, a benzyl group or a pyridyl group.
Claim 2
Dependent Claim 115 words
A compound of the formula, ##STR26## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group; R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a phenyl group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di-C 1-4 alkyl-substituted hydroxyphenyl group, a benzyl group or a pyridyl group.
Claim 3
Dependent Claim 18 words
The compound of claim 1, wherein R 1 and R 2 each represents a C 1-4 alkyl group.
Claim 4
Dependent Claim 14 words
The compound of claim 2, wherein R 1 and R 2 are methyl groups.
Claim 5
Dependent Claim 19 words
The compound of claim 2, wherein one of R 3 and R 4 is a C 1-10 alkyl group.
Claim 6
Dependent Claim 20 words
The compound of claim 4, wherein one of R 3 and R 4 is a branched C 3-8 alkyl group.
Claim 7
Dependent Claim 17 words
The compound of claim 5, wherein one of R 3 and R 4 is an isopropyl group.
Claim 8
Dependent Claim 17 words
The compound of claim 5, wherein one of R 3 and R 4 is a 2,4,4-trimethylpentyl group.
Claim 9
Dependent Claim 12 words
The compound of claim 4, wherein R 5 is a phenyl group.
Claim 10
Dependent Claim 12 words
The compound of claim 4, wherein R 5 is a 3,5-di-tert-butyl-4-hydroxyphenyl group.
Claim 11
Dependent Claim 12 words
The Compound of claim 4, wherein R 5 is a tert-butyl group.
Claim 12
Dependent Claim 12 words
The compound of claim 4, wherein R 5 is a pyridyl group.
Claim 13
Dependent Claim 12 words
The compound of claim 4, wherein R 5 is a 4-methylphenyl group.
Claim 14
Dependent Claim 12 words
The compound of claim 4, wherein R 5 is a 4-methoxyphenyl group.
Claim 15
Dependent Claim 14 words
The compound of claim 2, wherein R 3 and R 4 are hydrogen atoms.
Claim 16
Dependent Claim 12 words
The compound of claim 14, wherein R 5 is a phenyl group.
Claim 17
Dependent Claim 12 words
The compound of claim 2, wherein R 1 is a tert-butyl group.
Claim 18
Dependent Claim 12 words
The compound of claim 16, wherein R 2 is a methyl group.
Claim 19
Dependent Claim 12 words
The compound of claim 16, wherein R 2 is an ethyl group.
Claim 20
Dependent Claim 12 words
The compound of claim 17, wherein R 5 is a phenyl group.
Claim 21
Dependent Claim 12 words
The compound of claim 17, wherein R 5 is a benzyl group.
Claim 22
Dependent Claim 12 words
The compound of claim 18, wherein R 5 is a phenyl group.
Claim 23
Dependent Claim 12 words
The compound of claim 18, wherein R 5 is a cyclohexyl group.
Claim 24
Dependent Claim 12 words
The compound of claim 2, wherein R 2 is a methyl group.
Claim 25
Dependent Claim 12 words
The compound of claim 23, wherein R 1 is a cyclohexyl group.
Claim 26
Dependent Claim 12 words
The compound of claim 23, wherein R 1 is a 1-methylcyclohexyl group.
Claim 27
Dependent Claim 12 words
The compound of claim 24, wherein R 5 is a phenyl group.
Claim 28
Dependent Claim 12 words
The compound of claim 25, wherein R 5 is a phenyl group.
Claim 29
Dependent Claim 12 words
The compound of claim 25, wherein R 5 is a 4-butoxyphenyl group.
Claim 30
Independent Claim 322 words
A method of preparing a compound which comprises reacting a 2,2'-alkylidene bis(4,6-di-substituted phenol) of the formula (II), ##STR27## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group, or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group, with an esterifying agent selected from the group consisting of the compounds of the formulae (III) and (IV), R.sub.5 COCl (III) and (R.sub.5 CO).sub.2 O (IV) wherein R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a phenol group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di-C 1-4 alkyl-substituted hydroxyphenyl group, a benzyl group or a pyridyl group, substantially at an equimolar amount in the presence of a reaction medium while maintaining the reaction temperature at from about 0° C. to about 30° C. until about 50% of the 2,2'-alkylidene bis(4,6-di-substituted phenol) is converted to the compound of the formula ##STR28## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group; R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a phenyl group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di-C 1-4 alkyl-substituted hydroxyphenyl group, a benzyl group or a pyridyl group and thereafter raising said reaction temperature to range from about 50° C. to about 100° C.
Claim 31
Independent Claim 322 words
A method of preparing a compound which comprises reacting a 2,2'-alkylidene bis(4,6-di-substituted phenol) of the formula (II), ##STR27## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group, or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group, with an esterifying agent selected from the group consisting of the compounds of the formulae (III) and (IV), R.sub.5 COCl (III) and (R.sub.5 CO).sub.2 O (IV) wherein R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a phenol group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di-C 1-4 alkyl-substituted hydroxyphenyl group, a benzyl group or a pyridyl group, substantially at an equimolar amount in the presence of a reaction medium while maintaining the reaction temperature at from about 0° C. to about 30° C. until about 50% of the 2,2'-alkylidene bis(4,6-di-substituted phenol) is converted to the compound of the formula ##STR28## wherein R 1 and R 2 , which may be the same or different, each represents a C 1-4 alkyl group, a C 5-6 cycloalkyl group or a methyl-substituted C 5-6 cycloalkyl group; and one of R 3 and R 4 represents a hydrogen atom and the other represents a hydrogen atom or a C 1-10 alkyl group or both of them represent a methyl group; R 5 represents a C 4-9 alkyl group, a C 3-7 cycloalkyl group, a phenyl group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, a mono- or di-C 1-4 alkyl-substituted hydroxyphenyl group, a benzyl group or a pyridyl group and thereafter raising said reaction temperature to range from about 50° C. to about 100° C.
Claim 32
Dependent Claim 25 words
The method of claim 29, wherein the mole ratio of the esterifying agent to the 2,2'-alkylidene bis(4,6-di-substituted phenol) ranges from about 1.0 to about 1.3.
Claim 33
Dependent Claim 23 words
The method of claim 30, wherein the mole ratio of the esterifying agent to the 2,2'-alkylidene bis(4,6-di-substituted phenol) ranges from 1.00 to 1.10.
Claim 34
Dependent Claim 18 words
The method of claim 29, wherein the reaction is carried out in the presence of a basic catalyst.
Claim 35
Dependent Claim 35 words
The method of claim 29, wherein the reaction temperature is maintained at about 20° C. until about 50% of the 2,2'-alkylidene bis(4,6-di-substituted phenol) is converted to the compound of the formula (I) of claim 1.
Claim 36
Dependent Claim 30 words
The method of claim 29, wherein the reaction temperature is raised to about 80° C. after 50% of the 2,2'-alkylidene bis(4,6-di-substituted phenol) is converted to the compound of claim 1.
Claim 37
Dependent Claim 33 words
A polyurethane synthetic resin composition comprising 100 parts by weight of polyurethane synthetic resin and about 0.001 to about 10 parts by weight of the compound of the Formula (I) of claim 1.
Claim 38
Dependent Claim 6 words
A compound of the formula ##STR29##
Claim 39
Dependent Claim 6 words
A compound of the formula ##STR29##
Claim 40
Dependent Claim 6 words
A compound of the formula ##STR30##
Claim 41
Dependent Claim 6 words
A compound of the formula ##STR30##
Claim 42
Dependent Claim 6 words
A compound of the formula ##STR31##
Claim 43
Dependent Claim 6 words
A compound of the formula ##STR31##
Claim 44
Dependent Claim 6 words
A compound of the formula ##STR32##
Claim 45
Dependent Claim 6 words
A compound of the formula ##STR32##
Claim 46
Dependent Claim 6 words
A compound of the formula ##STR33##
Claim 47
Dependent Claim 6 words
A compound of the formula ##STR33##
Claim 48
Dependent Claim 6 words
A compound of the formula ##STR34##
Claim 49
Dependent Claim 6 words
A compound of the formula ##STR34##
Claim 50
Dependent Claim 34 words
The compound of claim 1 wherein R 5 represents a phenyl group, a C 1-4 alkyl-substituted phenyl group, a C 1-4 alkoxy-substituted phenyl group, or a mono- or di- C 1-4 alkyl-substituted hydroxyphenyl group.

References Cited (Backward Citations)

US3265661A Cited
US3579561A Cited
US3428711A Cited
US3642669A Cited
US3795700A Cited
US4107137A Cited
US4168387A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-12-20 1986-06-21 1986-12-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-12-20 1990-06-21 1990-12-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-12-20 1994-06-21 1994-12-21 $7700.00 Window Closed / Lapsed

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