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US4297401A Expired / Lapsed US ⏱️ 0.0 years remaining

Liquid crystal display and photopolymerizable sealant therefor

Assignee: 3M Co
•
Filing: 1978-12-26
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Granted: 1981-10-27
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Expires: 1998-12-26
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Abstract

Abstract A method of making a liquid crystal display cell wherein the planar glass plates of the cell are bonded together with a photopolymerizable epoxy-containing material to form a hermetically sealed cell and wherein the photocured seal is chemically resistant to the contents of the liquid crystals cell. Adhesion of the photopolymerizable epoxy material to the glass plates of the liquid crystal cell is improved by addition of glycidoxypropyl triethoxy silane or its precondensate.

Inventors

  • 👤 Mao-Jin Chern
  • 👤 Robert D. Lowrey

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 10:00
CPC Classifications
G; G02; G02F; G02F1/00; G02F1/01; G02F1/13; G02F1/133; G02F1/1333; G02F1/1339; C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/105; C09; C09J; C09J163/00; C09J171/00; C09J171/02; C08L; C08L2666/00; C08L2666/28; C08L2666/44; C09K; C09K2323/00; C09K2323/05; C09K2323/055

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 195 words
An improved liquid crystal display cell comprising a pair of half-cells having portions thereof bonded together by organic seal means wherein the improvement comprises an organic seal means comprising a photopolymerized sealant comprising a polymerized mixture of: (a) cationically polymerizable epoxide with a functionality of at least 1, and; (b) an organic aromatic onium catalyst comprising an aromatic adduct of (1) a diaromatic, triaromatic, or tetraaromatic organoatomic cation of a Group Va, VIa, or VIIa atom and (2) an anion; said onium catalyst being represented by the formula: ##STR5## wherein R 2 is an aromatic group at least as electron withdrawing as benzene, R 1 is an alkyl or alkenyl group, A is a Group Va, VIa, or VIIa atom, X is an anion, n is a positive whole integer of at least 2 up to the valence of A plus one, a is 0 or a positive whole integer up to the valence of A minus one, and n plus a is equal to the valence of A plus one and wherein at let two of said R 2 groups are bonded to A; said photopolymerized sealant being chemically resistant to liquid crystal materials.
Claim 2
Dependent Claim 195 words
An improved liquid crystal display cell comprising a pair of half-cells having portions thereof bonded together by organic seal means wherein the improvement comprises an organic seal means comprising a photopolymerized sealant comprising a polymerized mixture of: (a) cationically polymerizable epoxide with a functionality of at least 1, and; (b) an organic aromatic onium catalyst comprising an aromatic adduct of (1) a diaromatic, triaromatic, or tetraaromatic organoatomic cation of a Group Va, VIa, or VIIa atom and (2) an anion; said onium catalyst being represented by the formula: ##STR5## wherein R 2 is an aromatic group at least as electron withdrawing as benzene, R 1 is an alkyl or alkenyl group, A is a Group Va, VIa, or VIIa atom, X is an anion, n is a positive whole integer of at least 2 up to the valence of A plus one, a is 0 or a positive whole integer up to the valence of A minus one, and n plus a is equal to the valence of A plus one and wherein at let two of said R 2 groups are bonded to A; said photopolymerized sealant being chemically resistant to liquid crystal materials.
Claim 3
Dependent Claim 25 words
An improved liquid crystal display cell in accordance with claim 1, wherein said sealant comprises an adhesive-aiding amount of glycidoxpropyl triethoxy silane or its precondensate.
Claim 4
Dependent Claim 81 words
An improved liquid crystal display cell in accordance with claim 2, wherein said cationically polymerizable epoxide is selected from the group consisting of: (a) a mixture of Bisphenol A diglycidyl ether epoxy, triglycidyl ether epoxies of trihydroxymethyl propane, and 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexene carboxylate, and; (b) 3,4 epoxycyclohexylmethyl 3,4-epoxycyclohexylcarboxylate, and; (c) Bisphenol A diglycidyl ether; wherein said organic aromatic onium catalyst is triphenyl sulfonium hexafluorophosphate, and said adhesion-aiding amount of glycidoxypropyl triethoxy silane or its precondensate is 4-30% by weight of said photopolymerizable sealant.
Claim 5
Dependent Claim 26 words
An improved liquid crystal display cell in accordance with claim 1, wherein said seal means defines a plurality of cavities within said liquid crystal display cell.
Claim 6
Dependent Claim 23 words
An improved liquid crystal display cell in accordance with claim 1, wherein said display cell includes liquid crystal material disposed in said cell.
Claim 7
Dependent Claim 74 words
An improved multi-cavity liquid crystal display according to claim 1, 4 or 5 wherein: (a) said cationically polymerizable epoxide is a mixture of 55 parts by weight Bisphenol A diglycidyl ether epoxy, 25 parts triglycidyl ether epoxies of trihydroxymethyl propane, and 20 parts 3,4-epoxy-cyclohexylmethyl-3,4-epoxycyclohexene carboxylate; (b) said organic aromatic onium catalyst is triphenyl sulfonium hexafluorophosphate; (c) said adhesion-aiding amount of glycidoxypropyl triethoxy silane or its precondensate is 4-30% by weight of said photopolymerizable sealant.
Claim 8
Dependent Claim 228 words
A process for bonding a radiation-transparent substrate to a second substrate comprising: A. disposing a layer of an adhesive, sealant composition between said substrates and in contact therewith; said sealant composition comprising: (a) a cationically polymerizable epoxide with a functionality of at least 1, and (b) an organic aromatic onium catalyst comprising an aromatic adduct of (1) a diaromatic, triaromatic, or tetraaromatic organoatomic cation of a Group Va, VIa, or VIIa atom and (2) an anion; said onium catalyst being represented by the formula: ##STR6## wherein R 2 is an aromatic group at least as electron withdrawing as benzene, R 1 is an alkyl or alkenyl group, A is a Group Va, VIa, or VIIa atom, X is an anion, n is a positive whole integer of at least 2 up to the valence of A plus one, a is 0 or a positive whole integer up to the valence of A minus one, and n plus a is equal to the valence of A plus one and wherein at least two of said R 2 groups are bonded to A, and (c) an adhesion-aiding amount of glydicoxypropyl triethoxy silane or its precondensate; and said sealant composition being chemically resistant to liquid crystal materials; and B. exposing said layer to polymerizing radiation through said radiation-transparent substrate in an amount and for a time sufficient to polymerize said layer.
Claim 9
Dependent Claim 228 words
A process for bonding a radiation-transparent substrate to a second substrate comprising: A. disposing a layer of an adhesive, sealant composition between said substrates and in contact therewith; said sealant composition comprising: (a) a cationically polymerizable epoxide with a functionality of at least 1, and (b) an organic aromatic onium catalyst comprising an aromatic adduct of (1) a diaromatic, triaromatic, or tetraaromatic organoatomic cation of a Group Va, VIa, or VIIa atom and (2) an anion; said onium catalyst being represented by the formula: ##STR6## wherein R 2 is an aromatic group at least as electron withdrawing as benzene, R 1 is an alkyl or alkenyl group, A is a Group Va, VIa, or VIIa atom, X is an anion, n is a positive whole integer of at least 2 up to the valence of A plus one, a is 0 or a positive whole integer up to the valence of A minus one, and n plus a is equal to the valence of A plus one and wherein at least two of said R 2 groups are bonded to A, and (c) an adhesion-aiding amount of glydicoxypropyl triethoxy silane or its precondensate; and said sealant composition being chemically resistant to liquid crystal materials; and B. exposing said layer to polymerizing radiation through said radiation-transparent substrate in an amount and for a time sufficient to polymerize said layer.
Claim 10
Dependent Claim 32 words
A process for bonding a radiation-transparent substrate to a second substrate according to claim 7 wherein, said radiation-transparent substrate and said second substrate are both portions of a liquid crystal display cell.
Claim 11
Independent Claim 129 words
A method of bonding together corresponding half-cells of a liquid crystal display cell comprising: (a) providing a pair of corresponding display half-cells (b) applying a layer of photopolymerizable sealant to at least one of said half-cells in a pattern which, in cooperation with the corresponding half-cell, defines at least one cavity which can be filled with a liquid crystal material, said photopolymerizable composition being chemically resistant to liquid crystal materials, and said composition comprising: (1) a mixture of 55 parts by weight Bisphenol A diglycidyl ether epoxy, 25 parts triglycidyl ether epoxies or trihydroxymethyl propane and 20 parts 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexene carboxylate; (2) the organic aromatic onium catalyst triphenyl sulfonium hexafluorophosphate, and (3) 4-30% by weight glycidoxypropyl triethoxy silane or its precondensate; and (c) exposing said photopolymerizable composition to polymerizing radiation.
Claim 12
Independent Claim 129 words
A method of bonding together corresponding half-cells of a liquid crystal display cell comprising: (a) providing a pair of corresponding display half-cells (b) applying a layer of photopolymerizable sealant to at least one of said half-cells in a pattern which, in cooperation with the corresponding half-cell, defines at least one cavity which can be filled with a liquid crystal material, said photopolymerizable composition being chemically resistant to liquid crystal materials, and said composition comprising: (1) a mixture of 55 parts by weight Bisphenol A diglycidyl ether epoxy, 25 parts triglycidyl ether epoxies or trihydroxymethyl propane and 20 parts 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexene carboxylate; (2) the organic aromatic onium catalyst triphenyl sulfonium hexafluorophosphate, and (3) 4-30% by weight glycidoxypropyl triethoxy silane or its precondensate; and (c) exposing said photopolymerizable composition to polymerizing radiation.
Claim 13
Dependent Claim 14 words
A method according to claim 9 wherein said pattern defines a plurality of cavities.
Claim 14
Dependent Claim 24 words
A method according to claim 9 or 10 wherein said cavity is subsequently filled with a liquid crystal material and the cavity is plugged.

References Cited (Backward Citations)

US3702783A Cited
US3871746A Cited
US4007077A Cited
US3990781A Cited
GB1485658A Cited
US4037930A Cited
US4101513A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-10-26 1985-04-27 1985-10-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-10-26 1989-04-27 1989-10-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-10-26 1993-04-27 1993-10-27 $7700.00 Window Closed / Lapsed

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