US4287085A
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(2'-Cyano-4'-alkylphenyl)-3-cyano-4-alkoxybenzoates and liquid crystal composition including same
Assignee: Suwa Seikosha KK
•
Filing: 1980-04-29
•
Granted: 1981-09-01
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Expires: 2000-04-29
Abstract
Abstract Ester compounds suitable for use in liquid crystal compositions are provided. The ester compounds are (2'-cyano-4'-alkylphenyl)-3-cyano-4-n-alkoxybenzoates represented by the general formula: ##STR1## wherein R and R' each is a straight-chain alkyl group having one to eight carbon atoms. The ester compounds alone do not exhibit a liquid crystal phase, but have a relatively low melting point. Addition of at least one such ester compound to a liquid crystal composition lowers the value of the dielectric anisotropy of the composition at frequencies higher than the critical frequency, and lowers it at frequencies lower than the critical frequency. Such compositions are particularly well suited for the two-frequency matrix-addressing drive in a display of complex characters or graphic displays. The ester compounds in accordance with the invention are prepared by condensing a 3-bromo-4-n-alkoxybenzoyl chloride having the general formula: ##STR2## and a 2-cyano-4-n-alkylphenol having the general formula: ##STR3## to prepare a (2'-cyano-4'-n-alkylphenol)-3-bromo-4-n-alkoxybenzoate having the general formula: ##STR4## wherein R and R' each is a straight-chain alkyl group having from one to eight carbon atoms, and reacting the benzoate (IV) with cuprous cyanide to yield the desired ester (I).
Inventors
- 👤 Katsumori Takei
- 👤 Sadao Kanbe
- 👤 Yoshio Shionozaki
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 18:59
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/52; C09K19/54; C07; C07C; C07C51/00; C07C51/347; C07C51/363; C07C65/00; C07C65/21
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
35 words
An ester compound represented by the general formula ##STR57## wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from one to eight carbon atoms for defining a (2'-cyano-4'-n-alkylphenyl)-3-cyano-4-n-alkoxybenzoate.
Claim 2
Dependent Claim
35 words
An ester compound represented by the general formula ##STR57## wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from one to eight carbon atoms for defining a (2'-cyano-4'-n-alkylphenyl)-3-cyano-4-n-alkoxybenzoate.
Claim 3
Dependent Claim
28 words
The ester compound of claim 1, wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from four to seven carbon atoms.
Claim 4
Dependent Claim
31 words
The ester compound of claim 1, wherein R is a straight-chain alkyl group having seven carbon atoms and R' is a straight-chain alkyl group having four carbon atoms for defining (2'-cyano-4'-n'butylphenyl)-3-cyano-4-n-heptyloxybenzoate.
Claim 5
Dependent Claim
22 words
The ester compound of claim 1, wherein each R and R' is a straight-chain alkyl group having four carbon atoms defining (2'-cyano-4'-n-butylphenyl)-3-cyano-4-n-butyloxybenzoate.
Claim 6
Dependent Claim
23 words
The ester compound of claim 1 wherein each R and R' is a straight-chain alkyl group having five carbon atoms for defining (2'-cyano-4'-n-pentylphenyl)-3-cyano-4-n-pentyloxybenzoate.
Claim 7
Dependent Claim
31 words
The ester compound of claim 1, wherein R is a straight-chain alkyl group having seven carbon atoms and R' is a straight-chain alkyl group having five carbon atoms for defining (2'-cyano-4'-n-pentylphenol-3-cyano-4-n-hexyloxybenzoate.
Claim 8
Dependent Claim
31 words
The ester compound of claim 1, wherein R is a straight-chain alkyl group having four carbon atoms and R' is a straight-chain alkyl group having five carbon atoms for defining (2'-cyano-4'-n-pentylphenyl)-3-cyano-4-n-butyloxybenzoate.
Claim 9
Dependent Claim
77 words
A liquid crystal composition comprising liquid crystal material including at least one frequency-dependent liquid crystal compound inducing a dielectric dispersion at lower frequency, admixed with at least one (2'-cyano-4'-alkylphenyl)-3-cyano-4-alkyloxbenzoate represented by the general formula: ##STR58## wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from one to eight carbon atoms for increasing the absolute value of the negative dielectric anisotropy of the liquid crystal compound in the high frequency range.
Claim 10
Dependent Claim
77 words
A liquid crystal composition comprising liquid crystal material including at least one frequency-dependent liquid crystal compound inducing a dielectric dispersion at lower frequency, admixed with at least one (2'-cyano-4'-alkylphenyl)-3-cyano-4-alkyloxbenzoate represented by the general formula: ##STR58## wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from one to eight carbon atoms for increasing the absolute value of the negative dielectric anisotropy of the liquid crystal compound in the high frequency range.
Claim 11
Dependent Claim
41 words
The liquid crystal composition of claim 8, wherein said liquid crystal material has a positive dielectric anisotropy in the low frequency range lower than the critical frequency and a negative dielectric anisotropy in the high frequency range above the critical frequency.
Claim 12
Dependent Claim
32 words
The liquid crystal composition of claim 9, wherein said at least one benzoate is present between the effective amount to about 40 weight percent, based on the total weight of the composition.
Claim 13
Dependent Claim
33 words
The liquid crystal composition of claim 9, wherein said at least one benzoate is present in from an effective amount to about 20 weight percent, based on the total weight of the composition.
Claim 14
Dependent Claim
88 words
A liquid crystal composition including at least one liquid crystal compound selected from the group consisting of: ______________________________________
##STR59##
##STR60##
##STR61##
##STR62##
##STR63##
##STR64##
##STR65##
##STR66##
##STR67##
##STR68##
##STR69##
##STR70##
##STR71##
##STR72##
______________________________________ and admixed with at least one (2'-cyano-4'-alkylphenyl)-3-cyano-4-alkyloxybenzoate represented by the general formula: ##STR73## wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from one to eight carbon atoms for increasing the absolute value of the negative dielectric anisotropy of the liquid crystal compound in the high frequency range.
Claim 15
Dependent Claim
88 words
A liquid crystal composition including at least one liquid crystal compound selected from the group consisting of: ______________________________________
##STR59##
##STR60##
##STR61##
##STR62##
##STR63##
##STR64##
##STR65##
##STR66##
##STR67##
##STR68##
##STR69##
##STR70##
##STR71##
##STR72##
______________________________________ and admixed with at least one (2'-cyano-4'-alkylphenyl)-3-cyano-4-alkyloxybenzoate represented by the general formula: ##STR73## wherein each R and R' is selected from the group consisting of straight-chain alkyl groups having from one to eight carbon atoms for increasing the absolute value of the negative dielectric anisotropy of the liquid crystal compound in the high frequency range.
Claim 16
Dependent Claim
31 words
The liquid crystal composition of claim 8, wherein said liquid crystal material includes at least one liquid crystal compound selected from the group consisting of biphenyl, azoxy compounds and Schiff bases.
Claim 17
Dependent Claim
31 words
A liquid crystal composition comprising: __________________________________________________________________________
Compound Weight %
__________________________________________________________________________
##STR74## 7.9
##STR75## 5.5
##STR76## 15.7
##STR77## 15.8
##STR78## 7.8
##STR79## 7.9
##STR80## 7.9
##STR81## 11.8
##STR82## 11.8
##STR83## 7.9
__________________________________________________________________________
Claim 18
Dependent Claim
31 words
A liquid crystal composition comprising: __________________________________________________________________________
Compound Weight %
__________________________________________________________________________
##STR74## 7.9
##STR75## 5.5
##STR76## 15.7
##STR77## 15.8
##STR78## 7.8
##STR79## 7.9
##STR80## 7.9
##STR81## 11.8
##STR82## 11.8
##STR83## 7.9
__________________________________________________________________________
Claim 19
Dependent Claim
31 words
A liquid crystal composition comprising: ______________________________________
Weight
Compound %
______________________________________
##STR84## 6.2
##STR85## 5.5
##STR86## 16.0
##STR87## 16.0
##STR88## 8.4
##STR89## 8.4
##STR90## 7.0
##STR91## 12.0
##STR92## 12.0
##STR93## 8.5
______________________________________
Claim 20
Dependent Claim
31 words
A liquid crystal composition comprising: ______________________________________
Weight
Compound %
______________________________________
##STR84## 6.2
##STR85## 5.5
##STR86## 16.0
##STR87## 16.0
##STR88## 8.4
##STR89## 8.4
##STR90## 7.0
##STR91## 12.0
##STR92## 12.0
##STR93## 8.5
______________________________________
References Cited (Backward Citations)
US3953491A
Cited
US4110243A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |