US4883609A
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Pyrimidine derivatives
Assignee: Seiko Epson Corp
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Filing: 1988-11-16
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Granted: 1989-11-28
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Expires: 2008-11-16
Abstract
Abstract Pyrimidine derivatives represented by the general formula: ##STR1## wherein R is a straight chain alkyl group having from 1 to 12 carbon atoms or an alkoxy group having from 1 to 12 carbon atoms. The pyrimidine derivatives are added to nematic liquid crystal compositions to reduce the threshold voltage of display devices by increasing the N→I transition temperature and the dielectric anisotropy.
Inventors
- 👤 Shuhei Yamada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 01:57
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
34 words
A pyrimidine derivative having general formula: ##STR7## wherein, R is one of a straight chain alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon
Claim 2
Dependent Claim
34 words
A pyrimidine derivative having general formula: ##STR7## wherein, R is one of a straight chain alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon
Claim 3
Dependent Claim
15 words
The pyrimidine derivative of claim 1, wherein R includes from 3 to 6 carbon atoms.
Claim 4
Dependent Claim
17 words
The pyrimidine derivative of claim 1, wherein R is butyl and the pyrimidine derivative is 2-(3',5'-difluoro-4'-cyanophenyl)-5-(4"-butylphenyl) pyrimidine.
Claim 5
Dependent Claim
65 words
A liquid crystal composition comprising at least one nematic liquid crystal compound and an effective amount of pyrimidine derivative having the general formula: ##STR8## in which R is one of a straight chain alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon atoms for reducing the threshold voltage without adversely increasing the N→I transition point.
Claim 6
Dependent Claim
65 words
A liquid crystal composition comprising at least one nematic liquid crystal compound and an effective amount of pyrimidine derivative having the general formula: ##STR8## in which R is one of a straight chain alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon atoms for reducing the threshold voltage without adversely increasing the N→I transition point.
Claim 7
Dependent Claim
29 words
The liquid crystal composition of claim 4, wherein the pyrimidine derivative is present in an amount between 5 and 30 percent by weight of the total liquid crystal composition.
Claim 8
Independent Claim
160 words
A method of forming a pyrimidine derivative having the formula: ##STR9## wherein R is one of an alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon atoms, comprising: reacting an R-phenylacetylchloride with phosphorous oxychloride in dimethyl formamide to yield a 1-dimethylamino-3-dimethylimino-2-(R-phenyl)-propene-(1)-perchlorate; reacting 2,6-difluoroaniline with bromine in chloroform to yield 4-bromo-2,6-difluoroaniline; reacting 4-bromo-2,6-difluoroaniline with copper (I) cyanide and N-methyl-2-pyrrolidone to yield 4-cyano-2,6-difluoroaniline; reacting 4-cyano-2,6-difluoroaniline with sodium nitride and sulfuric acid in acetic acid to yield the diazonium salt which is reacted with copper (I) bromide in hydrobromic acid to yield 4-bromo-3,5-difluorobenzamidine hydrochloride; reacting 4-bromo-3,5-difluorobenzamidine hydrochloride with hydrogen chloride gas in ethanol and benzene; removing all solvents by distillation and reacting the resulting crystal with dry ammonia gas in ethanol to yield 4-bromo-3,5-difluorobenzamidine hydrochloride; reacting 1-dimethylamino-3-dimethylammonio-2-(R-phenyl)-propene-(1)-perchlorate with 4-bromo-3,5-difluorobenzamidine hydrochloride with metallic sodium in methanol to yield 2-(3',5'-difluoro-4'-bromophenyl)-5-(4"R-phenyl) pyrimidine; and reacting 2-(3',5'-difluoro-4'-(bromophenyl)-5-(4"R-phenyl) pyrimidine with copper (I) cyanide in N-methyl-2-pyrrolidone to yield 2-(3',5'-difluoro-4'cyanophenyl)-5-(4"-R-phenyl) pyrimidine.
Claim 9
Independent Claim
160 words
A method of forming a pyrimidine derivative having the formula: ##STR9## wherein R is one of an alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon atoms, comprising: reacting an R-phenylacetylchloride with phosphorous oxychloride in dimethyl formamide to yield a 1-dimethylamino-3-dimethylimino-2-(R-phenyl)-propene-(1)-perchlorate; reacting 2,6-difluoroaniline with bromine in chloroform to yield 4-bromo-2,6-difluoroaniline; reacting 4-bromo-2,6-difluoroaniline with copper (I) cyanide and N-methyl-2-pyrrolidone to yield 4-cyano-2,6-difluoroaniline; reacting 4-cyano-2,6-difluoroaniline with sodium nitride and sulfuric acid in acetic acid to yield the diazonium salt which is reacted with copper (I) bromide in hydrobromic acid to yield 4-bromo-3,5-difluorobenzamidine hydrochloride; reacting 4-bromo-3,5-difluorobenzamidine hydrochloride with hydrogen chloride gas in ethanol and benzene; removing all solvents by distillation and reacting the resulting crystal with dry ammonia gas in ethanol to yield 4-bromo-3,5-difluorobenzamidine hydrochloride; reacting 1-dimethylamino-3-dimethylammonio-2-(R-phenyl)-propene-(1)-perchlorate with 4-bromo-3,5-difluorobenzamidine hydrochloride with metallic sodium in methanol to yield 2-(3',5'-difluoro-4'-bromophenyl)-5-(4"R-phenyl) pyrimidine; and reacting 2-(3',5'-difluoro-4'-(bromophenyl)-5-(4"R-phenyl) pyrimidine with copper (I) cyanide in N-methyl-2-pyrrolidone to yield 2-(3',5'-difluoro-4'cyanophenyl)-5-(4"-R-phenyl) pyrimidine.
Claim 10
Dependent Claim
9 words
The method of claim 6, wherein R is n-butyl.
Claim 11
Dependent Claim
66 words
A liquid crystal display cell including a nematic liquid crystal composition and an effective amount of pyrimidine derivative having the general formula: ##STR10## wherein, R is one of a straight chain alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon atoms for reducing the threshold voltage of the composition without adversely increasing the N→I transition temperature.
Claim 12
Dependent Claim
66 words
A liquid crystal display cell including a nematic liquid crystal composition and an effective amount of pyrimidine derivative having the general formula: ##STR10## wherein, R is one of a straight chain alkyl group having from 1 to 12 carbon atoms and an alkoxy group having from 1 to 12 carbon atoms for reducing the threshold voltage of the composition without adversely increasing the N→I transition temperature.
Claim 13
Dependent Claim
11 words
The liquid crystal cell of claim 8, wherein R is n-butyl.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-11-27 | 1993-05-29 | 1993-11-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-11-27 | 1997-05-29 | 1997-11-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-11-27 | 2001-05-29 | 2001-11-28 | $7700.00 | Window Closed / Lapsed |