US5310509A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Dye-containing light-polarizing film
Assignee: Sumitomo Chemical Co Ltd
•
Filing: 1992-12-18
•
Granted: 1994-05-10
•
Expires: 2012-12-18
Abstract
Abstract The present invention relates to a dye-containing light-polarizing film wherein a disazo dye represented by the formula (I) is used: <IMAGE> (I) wherein Me represents a transition metal, being copper, nickel, zinc or iron, R represents a 1-naphthol or 2-naphthol residue which is bonded to azo group at the position adjacent to its hydroxyl group forming a complex bond together with the transition metal and which may have a substituent such as a sulfonic acid, sulfonamide, amino, acylamino or arylamino group or a hydroxyl group not adjacent to the azo group, X and Y represent a hydrogen atom, a C1-C4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, sulfonalkylamide, amino, acrylamino or nitro group or a halogen atom, and Z represents a hydrogen atom or a C1-C4 alkyl or lower alkoxy group, said formula (I) having from 1 to 3 sulfonic acid groups. Said dye-containing light-polarizing film, as compared with the conventional ones, not only exhibits a high durability, but also has excellent polarization performance enough to be comparable to the light-polarizing films in which iodine is used. Consequently, said dye-containing light-polarizing film is effectively used for use in displays in which liquid crystals are used and optical instruments including CRT filters.
Inventors
- 👤 Toyokazu Okada
- 👤 Koji Higashi
- 👤 Shinjiro Kawasaki
- 👤 Yutaka Nishii
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 00:59
CPC Classifications
G; G02; G02B; G02B5/00; G02B5/30; G02B1/00; G02B1/08; C; C09; C09B; C09B45/00; C09B45/02; C09B45/24; G02B5/3025; G02B5/3033
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
157 words
A dye-containing light-polarizing film comprising a dichroic dye absorbed into a high polymer film, in which said dichroic dye is a water-soluble copper-, nickel-, zinc- or iron-containing diazo dye represented by formula (I) as a free acid ##STR12## wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino, acylamino, nitro or halogen; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 2
Dependent Claim
157 words
A dye-containing light-polarizing film comprising a dichroic dye absorbed into a high polymer film, in which said dichroic dye is a water-soluble copper-, nickel-, zinc- or iron-containing diazo dye represented by formula (I) as a free acid ##STR12## wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino, acylamino, nitro or halogen; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 3
Dependent Claim
185 words
A dye-containing light-polarizing film showing a neutral gray comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is used in combination with an organic direct dye having absorption in a particular wave length region, wherein said dichroic dye is at least one of water-soluble copper-, nickel-, zinc- and iron-containing diazo dyes represented by formula (I) as a free acid, ##STR13## wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino, acylamino, nitro or halogen; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 4
Dependent Claim
185 words
A dye-containing light-polarizing film showing a neutral gray comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is used in combination with an organic direct dye having absorption in a particular wave length region, wherein said dichroic dye is at least one of water-soluble copper-, nickel-, zinc- and iron-containing diazo dyes represented by formula (I) as a free acid, ##STR13## wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino, acylamino, nitro or halogen; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 5
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 1, wherein the high polymer film is a film comprising polyvinyl alcohol or its derivatives.
Claim 6
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 2, wherein the high polymer film is a film comprising polyvinyl alcohol or its derivatives.
Claim 7
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 1, wherein, in formula (I), at least one of X and Y is sulfonic acid.
Claim 8
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 2, wherein, in formula (I), at least one of X and Y is sulfonic acid.
Claim 9
Dependent Claim
23 words
A dye-containing light-polarizing film according to claim 1, wherein, in formula (I), at least one of the substituents of R is sulfonic acid.
Claim 10
Dependent Claim
23 words
A dye-containing light-polarizing film according to claim 2, wherein, in formula (I), at least one of the substituents of R is sulfonic acid.
Claim 11
Dependent Claim
24 words
A dye-containing light-polarizing film according to claim 1, wherein, in formula (I), R is a 1-naphthol residue having at least one sulfonic acid group.
Claim 12
Dependent Claim
24 words
A dye-containing light-polarizing film according to claim 2, wherein, in formula (I), R is a 1-naphthol residue having at least one sulfonic acid group.
Claim 13
Dependent Claim
49 words
A dye-containing light-polarizing film according to claim 1, wherein, in formula (I), at least one of substituents X and Y other than hydrogen is present in the para-position to the azo bond, and at least one of the substituents of R other than hydrogen is present in the 6-position.
Claim 14
Dependent Claim
49 words
A dye-containing light-polarizing film according to claim 2, wherein, in formula (I), at least one of substituents X and Y other than hydrogen is present in the para-position to the azo bond, and at least one of the substituents of R other than hydrogen is present in the 6-position.
Claim 15
Dependent Claim
154 words
A dye-containing light-polarizing film comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is a water-soluble copper-, nickel-, zinc- or iron-containing diazo dye represented by formula (I) as a free acid wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino or acylamino, and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 16
Dependent Claim
154 words
A dye-containing light-polarizing film comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is a water-soluble copper-, nickel-, zinc- or iron-containing diazo dye represented by formula (I) as a free acid wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino or acylamino, and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 17
Dependent Claim
183 words
A dye-containing light-polarizing film showing a neutral gray comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is used in combination with an organic direct dye having absorption in a particular wave length region, wherein said dichroic dye is at least one of water-soluble copper-, nickel-, zinc- and iron-containing diazo dyes represented by formula (I) as a free acid, ##STR14## wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino or acylamino; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 18
Dependent Claim
183 words
A dye-containing light-polarizing film showing a neutral gray comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is used in combination with an organic direct dye having absorption in a particular wave length region, wherein said dichroic dye is at least one of water-soluble copper-, nickel-, zinc- and iron-containing diazo dyes represented by formula (I) as a free acid, ##STR14## wherein Me represents a transition metal selected from the group consisting of copper, nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent hydrogen, C 1 -C 4 alkyl, lower alkoxy, carboxylic acid, sulfonic acid, sulfonamide, amino or acylamino; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 19
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 13, wherein the high polymer film is a film comprising polyvinyl alcohol or its derivatives.
Claim 20
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 14, wherein the high polymer film is a film comprising polyvinyl alcohol or its derivatives.
Claim 21
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 13, wherein, in formula (I), at least one of X and Y is sulfonic acid.
Claim 22
Dependent Claim
22 words
A dye-containing light-polarizing film according to claim 14, wherein, in formula (I), at least one of X and Y is sulfonic acid.
Claim 23
Dependent Claim
23 words
A dye-containing light-polarizing film according to claim 13, wherein, in formula (I), at least one of the substituents of R is sulfonic acid.
Claim 24
Dependent Claim
23 words
A dye-containing light-polarizing film according to claim 14, wherein, in formula (I), at least one of the substituents of R is sulfonic acid.
Claim 25
Dependent Claim
23 words
A dye-containing light-polarizing film according to claim 13, wherein, in formula (I), R is 1-naphthol residue having at least one sulfonic acid group.
Claim 26
Dependent Claim
24 words
A dye-containing light-polarizing film according to claim 14, wherein, in formula (I), R is a 1-naphthol residue having at least one sulfonic acid group.
Claim 27
Dependent Claim
49 words
A dye-containing light-polarizing film according to claim 13, wherein, in formula (I), at least one of substituents X and Y other than hydrogen is present in the para-position to the azo bond, and at least one of the substituents of R other than hydrogen is present in the 6-position.
Claim 28
Dependent Claim
49 words
A dye-containing light-polarizing film according to claim 14, wherein, in formula (I), at least one of substituents X and Y other than hydrogen is present in the para-position to the azo bond, and at least one of the substituents of R other than hydrogen is present in the 6-position.
Claim 29
Dependent Claim
140 words
A dye-containing light-polarizing film comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is a water-soluble nickel-, zinc- or iron-containing diazo dye represented by formula (I) as a free acid ##STR15## wherein Me represents a transition metal selected from the group consisting of nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent nitro or halogen, and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 30
Dependent Claim
140 words
A dye-containing light-polarizing film comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is a water-soluble nickel-, zinc- or iron-containing diazo dye represented by formula (I) as a free acid ##STR15## wherein Me represents a transition metal selected from the group consisting of nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group; X and Y represent nitro or halogen, and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 31
Dependent Claim
168 words
A dye-containing light-polarizing film showing a neutral gray comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is used in combination with an organic direct dye having absorption in a particular wave length region, wherein said dichroic dye is at least one of water-soluble nickel-, zinc- and iron-containing diazo dyes represented by formula (I) as a free acid, ##STR16## wherein Me represents a transition metal selected from the group consisting of nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group, X and Y represent nitro or halogen; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
Claim 32
Dependent Claim
168 words
A dye-containing light-polarizing film showing a neutral gray comprising a dichroic dye adsorbed into a high polymer film, in which said dichroic dye is used in combination with an organic direct dye having absorption in a particular wave length region, wherein said dichroic dye is at least one of water-soluble nickel-, zinc- and iron-containing diazo dyes represented by formula (I) as a free acid, ##STR16## wherein Me represents a transition metal selected from the group consisting of nickel, zinc and iron; R represents a 1-naphthol or 2-naphthol residue which is bonded to the azo group at the position adjacent to the hydroxyl group forming a complex bond together with the transition metal and which may have a substituent selected from the group consisting of sulfonic acid, sulfonamide, amino, acylamino, arylamino and hydroxyl not adjacent to the azo group, X and Y represent nitro or halogen; and Z represents hydrogen, C 1 -C 4 alkyl or lower alkoxy; said formula (I) having from 1 to 3 sulfonic acid groups.
References Cited (Backward Citations)
DE2116008A1
Cited
US4128544A
Cited
EP0021372A2
Cited
US4514559A
Cited
EP0182632A2
Cited
JPS61255304A
Cited
JPS62156602A
Cited
JPS63189803A
Cited
US5007942A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-05-09 | 1997-11-08 | 1998-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-05-09 | 2001-11-08 | 2002-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-05-09 | 2005-11-08 | 2006-05-10 | $7700.00 | Window Closed / Lapsed |