Patent US4639439A successfully refreshed from Google Patents.
Patent US4427569A successfully refreshed from Google Patents.
US4427569A
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Short length ester liquid crystal mixtures and process for making same
Assignee: Victor Company of Japan Ltd
•
Filing: 1980-12-18
•
Granted: 1984-01-24
•
Expires: 2000-12-18
Abstract
Abstract New nematic liquid crystal (LC) ester mixtures with relatively short average molecular lengths are made by including one or more binary sets of components which have identical, or nearly identical, molecular lengths. Undesirable solids solution phase effects are avoided by either utilizing appreciable asymmetry in the alkyl end groups or by combining LC esters of different classes.
Inventors
- 👤 J. David Margerum
- 👤 Leroy J. Miller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 17:19
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/28; C09K19/20; C09K19/2007; C09K19/42; C09K19/46
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
343 words
Liquid crystal mixtures comprising a eutectic mixture consisting essentially of components selected from Table A herein and including at least one binary set of components, said binary set consisting of two components selected from one of the following Groups: Group 1: 1S04, 10-4, 10S4, 10-OOC3, 20-3, 20S3, 20-(C)3, 40S1; Group 2: 10-04, 10S04, 10S5, 10-(C)5, 40-01; Group 3: 1-06, 1S06, 20-5, 20S5, 20-(C)5, 40-3, 40S3; Group 4: 10-06, 10S06, 2-OOCφ2, 2-(Cl)OOCφ2, 2φCOO(CH 3 )-2, 40-(C)4, 60-01; Group 5: 40-6, 40-05, 40S6, 40-OOC4, 60-(C)4; Group 6: 4-OOCφ4, 4φCOO(CH 3 )-4; TABLE A
______________________________________
Code Structure
______________________________________
1-06
##STR35##
10-1
##STR36##
10-4
##STR37##
10-04
##STR38##
10-06
##STR39##
1604
##STR40##
1606
##STR41##
1064
##STR42##
1065
##STR43##
10604
##STR44##
10606
##STR45##
10-(C)5
##STR46##
10-OOC3
##STR47##
20-3
##STR48##
20-5
##STR49##
2063
##STR50##
2065
##STR51##
20-(C)3
##STR52##
20-(C)5
##STR53##
2-OOCφ2
##STR54##
2-(Cl)OOCφ2
##STR55##
2φCOO(CH.sub.3)2
##STR56##
3φ-4
##STR57##
40-1
##STR58##
40-3
##STR59##
40-6
##STR60##
40-01
##STR61##
40-05
##STR62##
4061
##STR63##
4063
##STR64##
4066
##STR65##
40-(C)4
##STR66##
40-OOC4
##STR67##
4-OOCφ4
##STR68##
4φCOO(CH.sub.3)4
##STR69##
5φ-4
##STR70##
5-φ5
##STR71##
5-(Cl)OOCφ5
##STR72##
60-3
##STR73##
60-4
##STR74##
60-5
##STR75##
60-01
##STR76##
60-(C)4
##STR77##
60-(C)5
##STR78##
60-OOC5
##STR79##
80-3
##STR80##
80-6
##STR81##
______________________________________
Code Name
______________________________________
1-06 p-tolyl p-hexoxybenzoate
10-1 p-methoxyphenyl p-toluate
10-4 p-methoxyphenyl p-butylbenzoate
10-04 p-methoxyphenyl p-butylbenzoate
10-06 p-methoxyphenyl p-hexoxybenzoate
1604 p-tolyl p-butoxythiobenzoate
1606 p-tolyl p-hexoxythiobenzoate
1064 p-methoxyphenyl p-butylthiobenzoate
1065 p-methoxyphenyl p-pentylthiobenzoate
10604 p-methoxyphenyl p-butoxythiobenzoate
10606 p-methoxyphenyl p-hexoxythiobenzoate
10-(C)5 p-methoxyphenyl trans-4-pentyl-
cyclohexanecarboxylate
10-OOC3 p-methoxyphenyl p-butyryloxybenzoate
20-3 p-ethoxyphenyl p-propylbenzoate
20-5 p-ethoxyphenyl p-pentylbenzoate
2063 p-ethoxyphenyl p-propylthiobenzoate
2065 p-ethoxyphenyl p-pentylthiobenzoate
20-(C)3 p-ethoxyphenyl trans-4-propyl-
cyclohexanecarboxylate
20-(C)5 p-ethoxyphenyl trans-4-pentyl
cyclohexanecarboxylate
2-OOCφ2
p-ethylphenyl p-(p-ethylbenzoyloxy)benzoate
2-(Cl)OOCφ2
p-ethylphenyl p-(p-ethylbenzoyloxy)-o-
chlorobenzoate
2φCOO(CH.sub.3)2
2-methyl-1,4-phenylene di(4-ethylbenzoate)
3φ-4 4-propylbiphenyl-4'-yl p-butylbenzoate
40-1 p-butoxyphenyl p-toluate
40-3 p-butoxyphenyl p-propylbenzoate
40-6 p-butoxyphenyl p-hexylbenzoate
40-01 p-butoxyphenyl p-methoxybenzoate
40-05 p-butoxyphenyl pentyloxybenzoate
4061 p-butoxyphenyl p-thiotoluate
4063 p-butoxyphenyl p-propylthiobenzoate
4066 p-butoxyphenyl p-hexylthiobenzoate
40-(C)4 p-butoxyphenyl trans-4-butyl-
cyclohexanecarboxylate
40-OOC4 p-butoxyphenyl p-valeryloxybenzoate
4-OOCφ4
p-butylphenyl p-(p-butylbenzoyloxy)benzoate
4φCOO(CH.sub.3)4
2-methyl-1,4-phenylene di(4-butylbenzoate)
5φ-4 4-pentylbiphenyl-4'-yl 4-butylbenzoate
5-φ5 p-pentylphenyl 4"-pentylbiphenyl-4'-carboxylate
5-(Cl)OOCφ5
p-pentylphenyl p-(p-pentylbenzoyloxy)-o-
chlorobenzoate
60-3 p-hexoxyphenyl p-propylbenzoate
60-4 p-hexoxyphenyl p-butylbenzoate
60-5 p-hexoxyphenyl p-pentylbenzoate
60-01 p-hexoxyphenyl p-methoxybenzoate
60-(C)4 p-hexoxyphenyl trans-4-butyl-
cyclohexanecarboxylate
60-(C)5 p-hexoxyphenyl trans-4-pentyl-
cyclohexanecarboxylate
60-OOC5 p-hexoxyphenyl p-hexanoyloxybenzoate
80-3 p-octyloxyphenyl p-propylbenzoate
80-6 p-octyloxyphenyl p-hexylbenzoate.
______________________________________
Claim 2
Dependent Claim
343 words
Liquid crystal mixtures comprising a eutectic mixture consisting essentially of components selected from Table A herein and including at least one binary set of components, said binary set consisting of two components selected from one of the following Groups: Group 1: 1S04, 10-4, 10S4, 10-OOC3, 20-3, 20S3, 20-(C)3, 40S1; Group 2: 10-04, 10S04, 10S5, 10-(C)5, 40-01; Group 3: 1-06, 1S06, 20-5, 20S5, 20-(C)5, 40-3, 40S3; Group 4: 10-06, 10S06, 2-OOCφ2, 2-(Cl)OOCφ2, 2φCOO(CH 3 )-2, 40-(C)4, 60-01; Group 5: 40-6, 40-05, 40S6, 40-OOC4, 60-(C)4; Group 6: 4-OOCφ4, 4φCOO(CH 3 )-4; TABLE A
______________________________________
Code Structure
______________________________________
1-06
##STR35##
10-1
##STR36##
10-4
##STR37##
10-04
##STR38##
10-06
##STR39##
1604
##STR40##
1606
##STR41##
1064
##STR42##
1065
##STR43##
10604
##STR44##
10606
##STR45##
10-(C)5
##STR46##
10-OOC3
##STR47##
20-3
##STR48##
20-5
##STR49##
2063
##STR50##
2065
##STR51##
20-(C)3
##STR52##
20-(C)5
##STR53##
2-OOCφ2
##STR54##
2-(Cl)OOCφ2
##STR55##
2φCOO(CH.sub.3)2
##STR56##
3φ-4
##STR57##
40-1
##STR58##
40-3
##STR59##
40-6
##STR60##
40-01
##STR61##
40-05
##STR62##
4061
##STR63##
4063
##STR64##
4066
##STR65##
40-(C)4
##STR66##
40-OOC4
##STR67##
4-OOCφ4
##STR68##
4φCOO(CH.sub.3)4
##STR69##
5φ-4
##STR70##
5-φ5
##STR71##
5-(Cl)OOCφ5
##STR72##
60-3
##STR73##
60-4
##STR74##
60-5
##STR75##
60-01
##STR76##
60-(C)4
##STR77##
60-(C)5
##STR78##
60-OOC5
##STR79##
80-3
##STR80##
80-6
##STR81##
______________________________________
Code Name
______________________________________
1-06 p-tolyl p-hexoxybenzoate
10-1 p-methoxyphenyl p-toluate
10-4 p-methoxyphenyl p-butylbenzoate
10-04 p-methoxyphenyl p-butylbenzoate
10-06 p-methoxyphenyl p-hexoxybenzoate
1604 p-tolyl p-butoxythiobenzoate
1606 p-tolyl p-hexoxythiobenzoate
1064 p-methoxyphenyl p-butylthiobenzoate
1065 p-methoxyphenyl p-pentylthiobenzoate
10604 p-methoxyphenyl p-butoxythiobenzoate
10606 p-methoxyphenyl p-hexoxythiobenzoate
10-(C)5 p-methoxyphenyl trans-4-pentyl-
cyclohexanecarboxylate
10-OOC3 p-methoxyphenyl p-butyryloxybenzoate
20-3 p-ethoxyphenyl p-propylbenzoate
20-5 p-ethoxyphenyl p-pentylbenzoate
2063 p-ethoxyphenyl p-propylthiobenzoate
2065 p-ethoxyphenyl p-pentylthiobenzoate
20-(C)3 p-ethoxyphenyl trans-4-propyl-
cyclohexanecarboxylate
20-(C)5 p-ethoxyphenyl trans-4-pentyl
cyclohexanecarboxylate
2-OOCφ2
p-ethylphenyl p-(p-ethylbenzoyloxy)benzoate
2-(Cl)OOCφ2
p-ethylphenyl p-(p-ethylbenzoyloxy)-o-
chlorobenzoate
2φCOO(CH.sub.3)2
2-methyl-1,4-phenylene di(4-ethylbenzoate)
3φ-4 4-propylbiphenyl-4'-yl p-butylbenzoate
40-1 p-butoxyphenyl p-toluate
40-3 p-butoxyphenyl p-propylbenzoate
40-6 p-butoxyphenyl p-hexylbenzoate
40-01 p-butoxyphenyl p-methoxybenzoate
40-05 p-butoxyphenyl pentyloxybenzoate
4061 p-butoxyphenyl p-thiotoluate
4063 p-butoxyphenyl p-propylthiobenzoate
4066 p-butoxyphenyl p-hexylthiobenzoate
40-(C)4 p-butoxyphenyl trans-4-butyl-
cyclohexanecarboxylate
40-OOC4 p-butoxyphenyl p-valeryloxybenzoate
4-OOCφ4
p-butylphenyl p-(p-butylbenzoyloxy)benzoate
4φCOO(CH.sub.3)4
2-methyl-1,4-phenylene di(4-butylbenzoate)
5φ-4 4-pentylbiphenyl-4'-yl 4-butylbenzoate
5-φ5 p-pentylphenyl 4"-pentylbiphenyl-4'-carboxylate
5-(Cl)OOCφ5
p-pentylphenyl p-(p-pentylbenzoyloxy)-o-
chlorobenzoate
60-3 p-hexoxyphenyl p-propylbenzoate
60-4 p-hexoxyphenyl p-butylbenzoate
60-5 p-hexoxyphenyl p-pentylbenzoate
60-01 p-hexoxyphenyl p-methoxybenzoate
60-(C)4 p-hexoxyphenyl trans-4-butyl-
cyclohexanecarboxylate
60-(C)5 p-hexoxyphenyl trans-4-pentyl-
cyclohexanecarboxylate
60-OOC5 p-hexoxyphenyl p-hexanoyloxybenzoate
80-3 p-octyloxyphenyl p-propylbenzoate
80-6 p-octyloxyphenyl p-hexylbenzoate.
______________________________________
Claim 3
Dependent Claim
36 words
A four component eutectic mixture of claim 1 wherein the binary set 20-5/40-3 is combined with 20-3 and 40-1 in mole fractions of approximately 0.32, 0.22, 0.25 and 0.22 for 20-5, 40-3, 20-3 and 40-1, respectively.
Claim 4
Dependent Claim
39 words
A five component eutectic mixture of claim 1 wherein the binary set 20-5/40-3 is combined with 20-3, 40-1 and 60-4 in mole fractions of approximately 0.12, 0.08, 0.10, 0.08 and 0.62 for 20-5, 40-3, 20-3, 40-1 and 60-4, respectively.
Claim 5
Dependent Claim
71 words
Multi-component eutectic mixtures of claim 1 wherein the components are phenyl thiobenzoates mixed in the mole fractions indicated in Table B for the mixtures 5N1, 5N2 and 5N3: TABLE B
______________________________________
Mixture No. and Mole Fraction
Compound of Each Compound
Code 5N1 5N2 5N3
______________________________________
10S4 0.131 0.094
10S5 0.157 0.123
10S06 0.110
20S3 0.074 0.058
20S5 0.063
40S1 0.127 0.134 0.097
40S3 0.270 0.283 0.217
40S6 0.372 0.389 0.302
______________________________________
Claim 6
Dependent Claim
82 words
Multi-component eutectic mixtures of claim 1 wherein the components are phenylbenzoates mixed in approximately the mole fractions indicated in Table C for the mixtures 2N42, 2N43, 2N44, 2N48, 42/48R: TABLE C
______________________________________
Mixture No. and Mole Fraction
Compound of Each Compound
Code 2N42 2N43 2N44 42/48R
______________________________________
10-1 0.112 0.073 0.032
20-3 0.222 0.148 0.068
20-5 0.283 0.180 0.240
0.075
40-1 0.191 0.119 0.048
40-3 0.192 0.117 0.160
0.045
40-6 0.364
60-3 0.197
60-4 0.601
60-5 0.249
80-3 0.165
80-6 0.0120.
______________________________________
Claim 7
Dependent Claim
193 words
Multi-component eutectic mistures of claim 1 wherein the components are mixed in approximately the mole fractions indicated in Tables D and E for the mixtures HRL-26N4, -256N1, -256N4, -256N5, -26N14, -26N20, -26N24, -26N25, -256N6 and -246N9: TABLE D
______________________________________
Compound
Mixture No. and Mole Fraction of Each Compound
Code 24N4 256N1 256N4 256N5 26N14
______________________________________
10-(C)5 0.293
10-00C3 0.058 0.043 0.047 0.044 0.041
10S5 0.163 0.163 0.138
10S06 0.116 0.108 0.101
20-3 0.108 0.070 0.084 0.078 0.068
20-(C)3 0.223 0.171 0.163 0.152 0.156
20-5 0.121 0.078 0.087 0.081 0.075
40-00C4 0.073 0.052 0.056 0.052
40-05 0.085
4-00Cφ4 0.041
60-01 0.194 0.134 0.154 0.144 0.147
60-00C5 0.223 0.174 0.137 0.128 0.169
______________________________________ TABLE E
______________________________________
Mole Fraction of Each Compound
Compound In Each Mixture
Code(a) 26N20 26N24 26N25 256N6 246N9
______________________________________
10-(C)5 0.257 0.272 0.242 0.267
10-00C3 0.034 0.037 0.031 0.036
10S5 0.131
20-3 0.057 0.033 0.061 0.053 0.060
20-(C)3 0.132 0.077 0.142 0.122 0.139
20-5 0.062 0.033 0.067 0.057 0.066
20-(C)5 0.071 0.077 0.065 0.075
3φ-4 0.088
40-00C4 0.041 0.045 0.037 0.044
40-(C)4 0.233
4-00Cφ4
0.066 0.070 0.061
4φC00(CH.sub.2)-4
0.065
5-(Cl)00Cφ5 0.167
60-3 0.108
60-5 0.215 0.133 0.229 0.201 0.224
60-(C)5 0.216.
______________________________________
Claim 8
Dependent Claim
187 words
Multi-Component eutectic mixtures of claim 1 wherein the components are mixed in approximately the mole fractions indicated in Tables F and G for the mixtures HRL-26N3, -256N12, -246N2, -246N3, -246N6, -246N7, -256N9 and -2456N1: TABLE F
______________________________________
Mole Fraction of Each Compound
Compound In Each Mixture
Code 26N3 256N12 246N2 246N3
______________________________________
10-(C)5 .176 .268 .278
10S5 .094
20-3 .033 .035 .060 .063
20-(C)3 .081 .139 .046
20-5 .036 .066 .070
20-(C)5 .040 .075 .080
20S5
2-(Cl)00φ2 .144
3φ-4 .093 .092
40-1 .022 .042 .044
40-3 .020 .039 .042
40-(C)4 .280 .242
40-6 .118
5φ-4 .083
5-φ5 .099 .102
5-(Cl)00Cφ5
.169
60-3 .113
60-5 .147
60-(C)5 .220
60-01 .065
80-3 .086
______________________________________ TABLE G
______________________________________
Mole Fraction of Each Compound
Compound In Each Mixture
Code 246N6 246N7 246N9 2456N1
______________________________________
10-(C)5 .235 .278 .246
10S5 .133
20-3 .051 .063 .076 .054
20-(C)3 .117 .146 .174 .125
20S3 .066
20-5 .054 .070 .085 .058
20-(C)5 .062 .080 .098 .066
20S5 .054
3φ-4 .078 .092 .082
40-1 .034 .044 .054 .037
40S1 .102
40-3 .032 .042 .052 .034
40S3 .239
40-6 .095
5-φ5 .088
60-3 .155 .186 .163.
______________________________________
Claim 9
Dependent Claim
21 words
Liquid crystal eutectic mixtures consisting of at least one binary set of components selected from the six groups in claim 1.
Claim 10
Dependent Claim
24 words
A binary eutectic mixture of claim 8 wherein the components 20-3 and 20-(C)3 are mixed in mole fractions of approximately 0.32 and 0.68, respectively.
Claim 11
Dependent Claim
24 words
A binary eutectic mixture of claim 8 wherein the components 10S5 and 10-(C)5 are mixed in mole fractions of approximately 0.36 and 0.64, respectively.
Claim 12
Dependent Claim
24 words
A binary eutectic mixture of claim 8 wherein the components 20-5 and 40-3 are mixed in mole fractions of approximately 0.58 and 0.42, respectively.
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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) | 1987-01-23 | 1987-07-25 | 1988-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-23 | 1991-07-25 | 1992-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-23 | 1995-07-25 | 1996-01-24 | $7700.00 | Window Closed / Lapsed |