CA1068096A - Liquid crystal composition - Google Patents
Liquid crystal compositionInfo
- Publication number
- CA1068096A CA1068096A CA232,816A CA232816A CA1068096A CA 1068096 A CA1068096 A CA 1068096A CA 232816 A CA232816 A CA 232816A CA 1068096 A CA1068096 A CA 1068096A
- Authority
- CA
- Canada
- Prior art keywords
- liquid crystal
- crystal composition
- compounds
- compound
- nematic liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
Abstract
LIQUID CRYSTAL COMPOSITION
ABSTRACT OF THE DISCLOSURE
A nematic liquid crystal composition comprising at least one of the compounds of the formula,
ABSTRACT OF THE DISCLOSURE
A nematic liquid crystal composition comprising at least one of the compounds of the formula,
Description
~06~3096 This invention relates to a novel nematic composition for use in a liquid crystal display device.
The liquid crystal display device is an electro-optical display device which diffuses or modulates light rays from a light source by utilizing a thin layer of a nematic state composition in which the molecules are arranged in a specific pattern.
This device comprises a first light-transmissible sub~
strate material, a first light-transmissible and electrically conductive coating applied on the first substrate material, a second substrate material, and a second light-transmissible and electrically conduc-tive coating applied on the second substrate material. -; 15 The device, as generally known, is so constructed that when a voltage is applied between said conductive coatings placed facing each other with a gap between them, said gap having been filled with a nematic liquid crystal composition, the latter undergoes a change in its molecular arrangement, resulting in velocity difference between the ordinary ray and the extraordinary ~-ay of `` incident light, change in the amount of light absorbed, and scattering of light due to the current flowing through said nematic liquid crystal composition.
"! 25 An optical display device, amont these known ''1 .
examples, has employed a nematic liquid crystal which ~
was developed for use in an electro-optical liquid -:
crystal display device operable at temperatures (about 25C) prevailing usually in residential structures.
There has been a strong demand, on the ., ' j~ ' :
~ .~
~ ~068096 other hand, for a nematic liquid crystal material which may remain in nematic state in a wider temperature range, because such a material would enlarge the : operable temperature range of an optical display device, leading to exploitation of new application fields for the electro-optical liquid crystal display device.
This invention is based on the finding that a number of specific compounds among bis(4'-n~-alkylbenzal)-2-methyl-1,4~phenylenediamines, R ~ CH=N ~ N=CH ~ R, and bis(4'-n-:~ CH3 alkylbenzal)-2-chloro-1,4-phenylenediamines, ~ .
R~ CH=N ~ N-CH ~ R (R represents an ;~ Cl . alkyl group) remain in the nematic state at tempera-tures in wide ranges and that a composition containing as one of the components at least one of said specific compounds also remains in the nematic ~tate in a wide .. temperature range.
Thus, according to the present invention there is provided a nematic liquid crystal composition comprising at least one of the compounds having the formula ~-:;:
: ,, Y ~ CH~N ~ N=CH ~ Y
". ~
. 2 '~
' 1068096 wherein X is methyl or chlorine and Y is a normal - CnH2n+l group wherein n is an integer of 2 to 8, and at least one of the compounds selected from the group consisting of the compounds having the general formula, CH=N ~} R2 ~ (A) : ~
,.': ':
0 R 0 ~ CH=N ~ R4 and (B) 3 ~ CH=N ~_~} 0-C- (CH2) 2CH3 ~ (C) CH30 ~CH=N ~} C- (CH2) 2CH3 ' (D) O ; ?
,~ .
wherein in the compound A, Rl is an alkyl group having 1 to 3 carbon atoms and R2 is an alkyl group having 2 to 5 carbon atoms;
and in the compound B, R3 is an alkyl group having 1 to 4 carbon `atoms and R4 is an alkyl group having 3 to 10 carbon atoms.
j~Before disclosing the invention in further detail, the :
procedure for synthesizing the present novel compounds is given ~
~:~ below. .-. ~
Synthesis Example 1 In 500 ml of benzene, were dissolved 0.2 mole of -`~ distilled and dried p-ethylbenzaldehyde, CH3CH2 ~ CHO , -~
:
~ 3 ~
~ .''"' ~,.
~`,,D, , , '~' and 0.1 mole of distilled and dried 2,5-diaminotoluene,
The liquid crystal display device is an electro-optical display device which diffuses or modulates light rays from a light source by utilizing a thin layer of a nematic state composition in which the molecules are arranged in a specific pattern.
This device comprises a first light-transmissible sub~
strate material, a first light-transmissible and electrically conductive coating applied on the first substrate material, a second substrate material, and a second light-transmissible and electrically conduc-tive coating applied on the second substrate material. -; 15 The device, as generally known, is so constructed that when a voltage is applied between said conductive coatings placed facing each other with a gap between them, said gap having been filled with a nematic liquid crystal composition, the latter undergoes a change in its molecular arrangement, resulting in velocity difference between the ordinary ray and the extraordinary ~-ay of `` incident light, change in the amount of light absorbed, and scattering of light due to the current flowing through said nematic liquid crystal composition.
"! 25 An optical display device, amont these known ''1 .
examples, has employed a nematic liquid crystal which ~
was developed for use in an electro-optical liquid -:
crystal display device operable at temperatures (about 25C) prevailing usually in residential structures.
There has been a strong demand, on the ., ' j~ ' :
~ .~
~ ~068096 other hand, for a nematic liquid crystal material which may remain in nematic state in a wider temperature range, because such a material would enlarge the : operable temperature range of an optical display device, leading to exploitation of new application fields for the electro-optical liquid crystal display device.
This invention is based on the finding that a number of specific compounds among bis(4'-n~-alkylbenzal)-2-methyl-1,4~phenylenediamines, R ~ CH=N ~ N=CH ~ R, and bis(4'-n-:~ CH3 alkylbenzal)-2-chloro-1,4-phenylenediamines, ~ .
R~ CH=N ~ N-CH ~ R (R represents an ;~ Cl . alkyl group) remain in the nematic state at tempera-tures in wide ranges and that a composition containing as one of the components at least one of said specific compounds also remains in the nematic ~tate in a wide .. temperature range.
Thus, according to the present invention there is provided a nematic liquid crystal composition comprising at least one of the compounds having the formula ~-:;:
: ,, Y ~ CH~N ~ N=CH ~ Y
". ~
. 2 '~
' 1068096 wherein X is methyl or chlorine and Y is a normal - CnH2n+l group wherein n is an integer of 2 to 8, and at least one of the compounds selected from the group consisting of the compounds having the general formula, CH=N ~} R2 ~ (A) : ~
,.': ':
0 R 0 ~ CH=N ~ R4 and (B) 3 ~ CH=N ~_~} 0-C- (CH2) 2CH3 ~ (C) CH30 ~CH=N ~} C- (CH2) 2CH3 ' (D) O ; ?
,~ .
wherein in the compound A, Rl is an alkyl group having 1 to 3 carbon atoms and R2 is an alkyl group having 2 to 5 carbon atoms;
and in the compound B, R3 is an alkyl group having 1 to 4 carbon `atoms and R4 is an alkyl group having 3 to 10 carbon atoms.
j~Before disclosing the invention in further detail, the :
procedure for synthesizing the present novel compounds is given ~
~:~ below. .-. ~
Synthesis Example 1 In 500 ml of benzene, were dissolved 0.2 mole of -`~ distilled and dried p-ethylbenzaldehyde, CH3CH2 ~ CHO , -~
:
~ 3 ~
~ .''"' ~,.
~`,,D, , , '~' and 0.1 mole of distilled and dried 2,5-diaminotoluene,
2 ~ NH 2 CH
The resulting solution was refluxed for 4 hours, while removing :~ the azeotropically distilled water by means of a Dean-Stark trap. Thereafter, the solvent was removed from the reaction mix-ture by distillation by use of a rotary evaporator. The distilla-tionresidue was collected and purified by repeated recrystalli-aztion from ethyle alcohol until a constant melting point was attained to obtain bis(4'-ethylbenzal)-2-methyl-1,4-phenylene- ~ :
diamine, CN3CEi`2~CH=N ~N=CH --e~ CH2CN3 (compound A), which remained in nematic state ~,i ,, .. .
: .
:",, , 'lo68~96 ~
in the temperature range of 93.8 - 182.5C. (herein-after said mesomorphic temperature range is referred to as M.R.).
In a manner similar to that mentioned above, the following compounds were preparedO
Bis-(4'-n-propylbenzal)-2-meth-1-1,4-phenylenediamine H3(CH2)2 ~ CH N ~ -N=CH- ~ -(CH2)2CH3
The resulting solution was refluxed for 4 hours, while removing :~ the azeotropically distilled water by means of a Dean-Stark trap. Thereafter, the solvent was removed from the reaction mix-ture by distillation by use of a rotary evaporator. The distilla-tionresidue was collected and purified by repeated recrystalli-aztion from ethyle alcohol until a constant melting point was attained to obtain bis(4'-ethylbenzal)-2-methyl-1,4-phenylene- ~ :
diamine, CN3CEi`2~CH=N ~N=CH --e~ CH2CN3 (compound A), which remained in nematic state ~,i ,, .. .
: .
:",, , 'lo68~96 ~
in the temperature range of 93.8 - 182.5C. (herein-after said mesomorphic temperature range is referred to as M.R.).
In a manner similar to that mentioned above, the following compounds were preparedO
Bis-(4'-n-propylbenzal)-2-meth-1-1,4-phenylenediamine H3(CH2)2 ~ CH N ~ -N=CH- ~ -(CH2)2CH3
3 (Compound B) M.R. 104.3- 195.6C
,', .
Bis-(4'-n-butylbenzal)-2-methyl-1,4-phenylenediamine 3(CH2)3- ~ -CH--N- ~ -N=CH- ~ -(CH2) CH
3 (Compound C) ,,- .
` Bis-(4'-n-pentylbenzal)-2-methyl-1,4-phenylenediamine CH3(CH2)4- ~ -CH=N ~ N--CH- ~ -(CH2)4CH3 3 (Compound D) M.R. 58.1 - 169.3C
, ~
Bis-(4'-n-hexylbenzal)-2-methyl-1,4-phenylenediamine ; 3(CH2)5- ~ -CH=N ~ -N-CH- ~ -(CH2)5CH
~, 3 (Compound E) M.R. 49.0 - 143.3C
~.
.. '', .
:, :
:. - - :
,', .
Bis-(4'-n-butylbenzal)-2-methyl-1,4-phenylenediamine 3(CH2)3- ~ -CH--N- ~ -N=CH- ~ -(CH2) CH
3 (Compound C) ,,- .
` Bis-(4'-n-pentylbenzal)-2-methyl-1,4-phenylenediamine CH3(CH2)4- ~ -CH=N ~ N--CH- ~ -(CH2)4CH3 3 (Compound D) M.R. 58.1 - 169.3C
, ~
Bis-(4'-n-hexylbenzal)-2-methyl-1,4-phenylenediamine ; 3(CH2)5- ~ -CH=N ~ -N-CH- ~ -(CH2)5CH
~, 3 (Compound E) M.R. 49.0 - 143.3C
~.
.. '', .
:, :
:. - - :
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Bis-(4~-n-heptylbenzal-2-methyl-1,4-phenylenediamine ; CH3(CH2)6- ~ -CH=N ~ N-CH- ~ -(CH2)6CH3 CH3 (Compound F) M-R- 44.7C - 143.7C
Bis-(4'-n-octylbenzal)-2-methyl-1,4-phenylenediamine CH3(CH2)7-~-CH_N-~-N-CH-~-(CH2)7CH3 3 (Compound G) M.R. 46.2 - 130.2C
.', .:.
Synthesis Example 2 2-Chloro-1,4-phenylenediamine sulfate, NH ~ -NH2.H2SO4, was dissolved in water, neutralized ... :.
with an aqueous sodium hydroxide solution, and extract-!', ed with ethyl ether. The ether extract layer, after -removal of the ether, was purified by recrystallization, repeated twice, from chlorobenzene, and dried to obtain 2-chloro-1,4-phenylenediamine, NH2- ~ -NH2. In 500 ml Cl . ~ :
of benzene, were dissolved 0.1 mole of said 2-chloro-1,4-phenylenediamine and 0.2 mole of distilled and dried p-methylbenzaldehyde. me resulting solution was refluxed for about 4 hours, while removing the - azeotropically distilled water by means of a Dean- -:
Stark trap~ Thereafter, the solvent was removed from the reaction mixture by distillation by use of a , . . .
~ 068096 rotary evaporator The distillation residue was collect-ed and purified by repea-ted recrystallization from isopropyl alcohol until a constant melting point was attained to obtain bis(4'-methylbenzal)-2-chloro-1,4~
phenylenediamine, CH3- ~ -CH=N- ~ -N=CH- ~ -CH3 Cl ; (Compound H), which showed M.R. of 144.4 - 196.6C.
In a manner similar to that mentioned above, the following compounds were prepared. .
Bis-(4'-ethylbenzal)2-chloro-1,4-phenylenediamine CH3CH2 ~ -CH_N- ~ -N=CH- ~ -CH2CH3 (Compound I) : M.R. 110.2 - 164.0C
. Bis-(4'-propylbenzal)-2-chloro-1,4-phenylenediamine :
CH3(CH2)2- ~ -CH-N- ~ -N=CH- ~ -(CH2)2CH3 Cl (Compound J) ~.
M-R- 84.8 - 186.7C
: 15 Bis-(4'-n-butylbenzal)-2-chloro-1,4-phenylenediamine ; 3(CH2)3- ~ -CH=N- ~ -N=CH- ~ -(CH2) CH
Cl (Ccmpound K) ..
! M.R. 4906 - 155.5C ;.
'.' ''' . ~.
,: ,j . ,;: , .
. .'.~:: ' ~` ~
., ', .
. 6 '''.' ~' ' ~06~096 Bis-(4'-n-pentylbenzal)-2-chloro-1,4-phenylenediamine CH3(CH2)4 ~ -CH=N ~ N=CH ~ -(CH2)4CH3 Cl (Compound LJ
~,;', , .
~ ~068~
Bis-(4~-n-heptylbenzal-2-methyl-1,4-phenylenediamine ; CH3(CH2)6- ~ -CH=N ~ N-CH- ~ -(CH2)6CH3 CH3 (Compound F) M-R- 44.7C - 143.7C
Bis-(4'-n-octylbenzal)-2-methyl-1,4-phenylenediamine CH3(CH2)7-~-CH_N-~-N-CH-~-(CH2)7CH3 3 (Compound G) M.R. 46.2 - 130.2C
.', .:.
Synthesis Example 2 2-Chloro-1,4-phenylenediamine sulfate, NH ~ -NH2.H2SO4, was dissolved in water, neutralized ... :.
with an aqueous sodium hydroxide solution, and extract-!', ed with ethyl ether. The ether extract layer, after -removal of the ether, was purified by recrystallization, repeated twice, from chlorobenzene, and dried to obtain 2-chloro-1,4-phenylenediamine, NH2- ~ -NH2. In 500 ml Cl . ~ :
of benzene, were dissolved 0.1 mole of said 2-chloro-1,4-phenylenediamine and 0.2 mole of distilled and dried p-methylbenzaldehyde. me resulting solution was refluxed for about 4 hours, while removing the - azeotropically distilled water by means of a Dean- -:
Stark trap~ Thereafter, the solvent was removed from the reaction mixture by distillation by use of a , . . .
~ 068096 rotary evaporator The distillation residue was collect-ed and purified by repea-ted recrystallization from isopropyl alcohol until a constant melting point was attained to obtain bis(4'-methylbenzal)-2-chloro-1,4~
phenylenediamine, CH3- ~ -CH=N- ~ -N=CH- ~ -CH3 Cl ; (Compound H), which showed M.R. of 144.4 - 196.6C.
In a manner similar to that mentioned above, the following compounds were prepared. .
Bis-(4'-ethylbenzal)2-chloro-1,4-phenylenediamine CH3CH2 ~ -CH_N- ~ -N=CH- ~ -CH2CH3 (Compound I) : M.R. 110.2 - 164.0C
. Bis-(4'-propylbenzal)-2-chloro-1,4-phenylenediamine :
CH3(CH2)2- ~ -CH-N- ~ -N=CH- ~ -(CH2)2CH3 Cl (Compound J) ~.
M-R- 84.8 - 186.7C
: 15 Bis-(4'-n-butylbenzal)-2-chloro-1,4-phenylenediamine ; 3(CH2)3- ~ -CH=N- ~ -N=CH- ~ -(CH2) CH
Cl (Ccmpound K) ..
! M.R. 4906 - 155.5C ;.
'.' ''' . ~.
,: ,j . ,;: , .
. .'.~:: ' ~` ~
., ', .
. 6 '''.' ~' ' ~06~096 Bis-(4'-n-pentylbenzal)-2-chloro-1,4-phenylenediamine CH3(CH2)4 ~ -CH=N ~ N=CH ~ -(CH2)4CH3 Cl (Compound LJ
5 Bis- (4'-n-hexylbenzal)-2-chloro-1,4-phenylenediamine 3( 2)5 ~ -CH=N ~ -N=CH ~ -(CH2) CH
Cl (Compound M) M.R. 36.8 - 134.0 C
There is scarcely any single compound which re-mains in nematic liquid crystal state over a wide temperature range, including near room temperatures. Accordingly, attempts have been made to achieve this object by a mixture of two or more compounds.
According to this invention, there is provided compositions which remain in nematic state over a wide tempe-- rature range and, in addition, at temperatures in the neighbor-hood of room temperature, by mixing the present novel nematic liquid crys~ 1 compound with other compounds in a suitable `;
proportion. Such compositions are very useful as liquid crystal material for use in electro-optical liquid crystal display devices.
By way of illustration, but not by way of limita-tion, Examples of compositions according to this invention are listed below.
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There is scarcely any single compound which re-mains in nematic liquid crystal state over a wide temperature range, including near room temperatures. Accordingly, attempts have been made to achieve this object by a mixture of two or more compounds.
According to this invention, there is provided compositions which remain in nematic state over a wide tempe-- rature range and, in addition, at temperatures in the neighbor-hood of room temperature, by mixing the present novel nematic liquid crys~ 1 compound with other compounds in a suitable `;
proportion. Such compositions are very useful as liquid crystal material for use in electro-optical liquid crystal display devices.
By way of illustration, but not by way of limita-tion, Examples of compositions according to this invention are listed below.
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Claims (5)
1. A nematic liquid crystal composition comprising at least one of the compounds having the formula, wherein X is methyl and Y is a normal - CnH2n+1 group wherein n is an integer of 2 to 8, and at least one of the compounds selected from the group consisting of the compounds having the general formula, (A) (B) , (C) wherein in the compound A, R1 is an alkyl group having 1 to 3 carbon atoms and R2 is an alkyl group having 2 to 5 carbon atoms;
and in the compound B, R3 is an alkyl group having 1 to 4 carbon atoms and R4 is an alkyl group having 3 to 10 carbon atoms.
and in the compound B, R3 is an alkyl group having 1 to 4 carbon atoms and R4 is an alkyl group having 3 to 10 carbon atoms.
2. A nematic liquid crystal composition according to claim 1, which comprises one of the compounds of the formulas, and .
3. A nematic liquid crystal composition according to claim 1, which comprises one of the compounds of the formulas, and .
4. A nematic liquid crystal composition according to claim 1, which comprises one of the compounds of the formula, .
5. A nematic liquid crystal composition according to claim 1, which comprises one of the compounds of the formula, wherein X is methyl and Y is a normal-CnH2n+1 group, wherein n is an integer of 2 or 3.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9047474A JPS5118283A (en) | 1974-08-06 | 1974-08-06 | EKISHOHYOJISOCHI |
| JP9047374A JPS5118282A (en) | 1974-08-06 | 1974-08-06 | EKISHOHYOJISOCHI |
| JP10114174A JPS5127885A (en) | 1974-09-02 | 1974-09-02 | EKISHOHYOJISOCHI |
| JP10540574A JPS5131685A (en) | 1974-09-11 | 1974-09-11 | EKISHOHYOJISOCHI |
| JP10540674A JPS5131686A (en) | 1974-09-11 | 1974-09-11 | EKISHOHYOJISOCHI |
| JP13399674A JPS5159076A (en) | 1974-11-19 | 1974-11-19 | EKISHOHYOJISOCHI |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068096A true CA1068096A (en) | 1979-12-18 |
Family
ID=27551807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,816A Expired CA1068096A (en) | 1974-08-06 | 1975-08-05 | Liquid crystal composition |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4082686A (en) |
| CA (1) | CA1068096A (en) |
| DE (1) | DE2535125A1 (en) |
| FR (1) | FR2281416A1 (en) |
| GB (1) | GB1472836A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4090975A (en) * | 1974-11-01 | 1978-05-23 | Itek Corporation | Mixtures of nematic liquid crystal materials |
| DE2557267A1 (en) * | 1975-12-19 | 1977-06-30 | Bbc Brown Boveri & Cie | LIQUID CRYSTAL SUBSTANCE |
| US4180475A (en) * | 1976-02-26 | 1979-12-25 | Hoffmann La Roche | Liquid crystal mixtures |
| JPS5928326B2 (en) * | 1976-12-02 | 1984-07-12 | 富士写真フイルム株式会社 | Photopolymerizable composition |
| US4406814A (en) * | 1981-04-10 | 1983-09-27 | Eaton Corporation | Liquid crystalline materials and optical displays utilizing same |
| JPS588779A (en) * | 1981-07-08 | 1983-01-18 | Hitachi Ltd | Liquid crystal display device |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3731986A (en) * | 1971-04-22 | 1973-05-08 | Int Liquid Xtal Co | Display devices utilizing liquid crystal light modulation |
| US3655270A (en) * | 1971-06-01 | 1972-04-11 | Linda Truitt Creagh | Electro-optical display devices using nematic mixtures with very wide temperature ranges |
| US3970579A (en) * | 1971-08-02 | 1976-07-20 | Owens-Illinois, Inc. | Low melting liquid-crystal mixtures |
| US3838059A (en) * | 1972-02-22 | 1974-09-24 | Hughes Aircraft Co | Liquid crystal composition |
| US3965029A (en) * | 1974-02-04 | 1976-06-22 | Kent State University | Liquid crystal materials |
| JPS5637268B2 (en) * | 1974-03-25 | 1981-08-29 |
-
1975
- 1975-08-04 GB GB3259475A patent/GB1472836A/en not_active Expired
- 1975-08-04 US US05/601,343 patent/US4082686A/en not_active Expired - Lifetime
- 1975-08-05 FR FR7524362A patent/FR2281416A1/en active Granted
- 1975-08-05 CA CA232,816A patent/CA1068096A/en not_active Expired
- 1975-08-06 DE DE19752535125 patent/DE2535125A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2535125A1 (en) | 1976-02-26 |
| US4082686A (en) | 1978-04-04 |
| FR2281416A1 (en) | 1976-03-05 |
| FR2281416B1 (en) | 1980-04-30 |
| GB1472836A (en) | 1977-05-11 |
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