Source: http://www.google.com/patents/US5830385?dq=6,250,774
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Patent US5830385 - Method of making liquid crystal composite - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA liquid crystal light composite in which discrete volumes of a liquid crystal material are dispersed in a matrix material is produced by a process in which a reactive additive formulation is added and photopolymerized. The reactive additive formulation includes mono- and multifunctional compounds in...http://www.google.com/patents/US5830385?utm_source=gb-gplus-sharePatent US5830385 - Method of making liquid crystal compositeAdvanced Patent SearchPublication numberUS5830385 APublication typeGrantApplication numberUS 08/773,803Publication dateNov 3, 1998Filing dateJan 24, 1997Priority dateDec 21, 1994Fee statusPaidAlso published asCA2208509A1, CA2208509C, EP0799287A1, WO1996019547A1Publication number08773803, 773803, US 5830385 A, US 5830385A, US-A-5830385, US5830385 A, US5830385AInventorsAldrich N. K. Lau, Lanchi P. Vo, Robert H. Reamey, John R. Havens, Kathleen Di ZioOriginal AssigneeRaychem CorporationExport CitationBiBTeX, EndNote, RefManPatent Citations (41), Non-Patent Citations (26), Referenced by (6), Classifications (13), Legal Events (6) External Links: USPTO, USPTO Assignment, EspacenetMethod of making liquid crystal composite
US 5830385 AAbstract
1. A method of making a liquid crystal light composite in which discrete volumes of a liquid crystal material are dispersed in a matrix material and the matrix material and the liquid crystal material are separated from each other by a wall formed by the polymerization of a reactive additive formulation, comprising the steps of:(a) providing an emulsion comprising plural discrete volumes of a liquid crystal material encapsulated in a matrix material carried in a carrier medium, the emulsion further comprising a reactive additive formulation comprising:(I) between 83 and 93.3 weight percent of at least two monofunctional compounds of the structure ##STR43## the group --R1 being --CH3 or --H and the group --R2 being an alkyl, aryl, alkylaryl, alkylcycloalkyl, cycloalkylalkyl, hydroxyalkyl, fluoroalkyl, or fluoroaryl group; wherein (A) each group --R2 has a chain length of 6 or (B) at least one group --R2 has a chain length other than six, in which latter event the distribution of chain lengths among the groups --R2 is according to the following table ______________________________________Mole Percent  Chain Length______________________________________ 5 to 90      &#8806;510 to 95      &gt;5______________________________________ the mole percent's being based on the total amount of monofunctional compounds; (II) between 5 and 16.9 weight percent of at least one multifunctional compound having acrylic or methacrylic functionality and being derived from diols or polyols containing aliphatic, aromatic, ester, epoxy, amide, imide, carbamate, or mesogenic segments; and (III) between 0.1 and 5.0 weight percent of at least one photoinitiator; the weight percent's being based on the combined amounts of monofunctional compounds, multifunctional compound, and photoinitiator; (b) photopolymerizing the monofunctional and multifunctional compounds in the reactive additive formulation to form the wall separating the matrix material and the liquid crystal material; (c) applying a coating of the emulsion onto a substrate; and (d) drying the coating by permitting the carrier medium to evaporate. 2. A method according to claim 1, wherein the at least two monofunctional compounds are selected from the group consisting of n-pentyl acrylate, 2,4,4-trimethylpentyl acrylate, n-hexyl acrylate, n-decyl acrylate, 3,5,5-trimethylhexyl acrylate, 2-ethylhexyl acrylate, and 4-tert-butyl-cyclohexyl acrylate.
TABLE I______________________________________                        --R2                        Group                        Chain   AmountCompound         Type        Length  (wt %)______________________________________3,5,5-Trimethylhexyl acrylate (XI)            Monofunctional                        6       44.52-Ethylhexyl acrylate (X)            Monofunctional                        6       44.5Photomer &#8482; 5018            Multifunctional                        N/A     10.0n-Pentyl acrylate (III)            Monofunctional                        5       13.52-Ethylhexyl acrylate (X)            Monofunctional                        6       35.1n-Decyl acrylate (XVI)            Monofunctional                        10      40.4Photomer &#8482; 5018            Multifunctional                        N/A     10.0n-Pentyl acrylate ((III)            Monofunctional                        5       62.3n-Hexyl acrylate (VII)            Monofunctional                        6       26.7Photomer &#8482; 5018            Multifunctional                        N/A     10.0______________________________________
The monofunctional and multifunctional compounds are photopolymerized by irradiating the emulsion with ultraviolet (UV) light). A conventional UV light source is suitable, but we have generally used a medium pressure mercury vapor lamp having emission peaks at 250, 310, and 360 nm. This emission pattern is found to fit well with the absorption spectrum of a preferred photoinitiator, Darocur™ 4265. Those skilled in the art will appreciate that, for a given UV light source, one particular photoinitiator may be more effective than the others. Typically, irradiation is effected for 15 min at 0� C. under 12 mW/cm2 radiation. The temperature and duration may vary depending on the exact formulation. The promote complete photo-polymerization, the emulsion is stirred during irradiation. Thermal and photo DSC data indicates the degree of cure is greater than 98%.
This is a representative procedure for preparing of liquid crystal composites according to this invention and the corresponding light valves. Liquid crystal material (preferably a halogenated nematic liquid crystal, such as the TL-- series of liquid crystals from EM Industries) is dissolved in a known amount of a reactive additive formulation at 21� C. until saturation, as indicated by a slight cloudiness of the solution. The solution is emulsified in a 5 to 15 weight % aqueous solution of PVA (e.g., Airvol™ 205 from Air Products). Emulsifying agents other than PVA may be used. Optionally a surfactant or coating aid may be added prior to emulsification. The coating aid may also be added to the final coating emulsion prior to coating. Both the speed and duration of mixing can be adjusted to yield the desired particle size, usually in the range of 1.5 to 2.5 μm (preferably 2.0 μm) median volume diameter. The emulsion is adjusted to 40 weight % of non-aqueous components by adding the necessary amount of water, then allowed to defoam by standing for at least 2 hours. After filtering through a 3.0 μm polycarbonate membrane and storing at approximately 0� C. for at least 30 min, aliquots of the cold emulsion about 8 mL in size are transferred into 30 mL plastic beakers equipped with a magnetic stirrer. Each batch is cooled to about -5� C. by blowing cold nitrogen gas across it with constant stirring for 5 min. The batches are then irradiated with UV light at an intensity of about 12 mW/cm2 for 15 min, while maintaining the temperature at or below 0� C. The emulsion is filtered again through a 5 μm polycarbonate membrane. The emulsion may be centrifuged if desired to narrow the droplet size distribution. The pellet obtained from the centrifugation is redispersed in another matrix material (e.g., a 50:50 wt % mixture of Neorez™ R967 (a polyurethane matrix) and Airvol™ 205 PVA) to form an emulsion ready for coating.
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Phys. , vol. 65, No. 6, pp. 2224 2230 (1976).* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS6093344 *Jun 25, 1998Jul 25, 2000Hyundai Electronics Industries Co., Ltd.Polymer dispersed liquid crystal display deviceUS6180028 *Jul 30, 1998Jan 30, 2001Asahi Glass Company Ltd.Liquid-crystal composition and polymeric liquid crystal obtained by polymerizing the sameUS6203866 *Mar 13, 1998Mar 20, 2001Fujitsu LimitedFerroelectric liquid crystal display element and manufacturing method thereofUS6395352Sep 28, 2000May 28, 2002Fujitsu LimitedFerroelectric liquid crystal display element and manufacturing method thereofUS6548127 *Jan 26, 1999Apr 15, 2003Rolic AgLiquid-crystalline photocrosslinkable mixtureUS7896484 *Jun 5, 2008Mar 1, 2011Kabushiki Kaisha ToshibaInk jet recording apparatus* Cited by examinerClassifications U.S. Classification252/299.01, 349/187, 252/299.1International ClassificationC08F220/10, C08F2/48, C09K19/54, G02F1/13, C09D155/00, C08F290/06, G02F1/1333, C09D133/04Cooperative ClassificationC09K19/544European ClassificationC09K19/54A3Legal EventsDateCodeEventDescriptionApr 5, 2000ASAssignmentOwner name: AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA, PFree format text: MERGER & REORGANIZATION;ASSIGNOR:RAYCHEM CORPORATION, A CORPORATION OF DELAWARE;REEL/FRAME:011682/0001Effective date: 19990812Owner name: TYCO INTERNATIONAL LTD., A CORPORATION OF BERMUDA,Free format text: MERGER & REORGANIZATION;ASSIGNOR:RAYCHEM CORPORATION, A CORPORATION OF DELAWARE;REEL/FRAME:011682/0001Effective date: 19990812Owner name: AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA 10Owner name: TYCO INTERNATIONAL LTD., A CORPORATION OF BERMUDAOwner name: AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA 10Free format text: MERGER & REORGANIZATION;ASSIGNOR:RAYCHEM CORPORATION, A CORPORATION OF DELAWARE;REEL/FRAME:011682/0001Effective date: 19990812Owner name: TYCO INTERNATIONAL (PA), INC., A CORPORATION OF NEFree format text: MERGER & REORGANIZATION;ASSIGNOR:RAYCHEM CORPORATION, A CORPORATION OF DELAWARE;REEL/FRAME:011682/0001Effective date: 19990812Owner name: TYCO INTERNATIONAL LTD., A CORPORATION OF BERMUDAFree format text: MERGER & REORGANIZATION;ASSIGNOR:RAYCHEM CORPORATION, A CORPORATION OF DELAWARE;REEL/FRAME:011682/0001Effective date: 19990812Owner name: TYCO INTERNATIONAL (PA), INC., A CORPORATION OF NEFree format text: MERGER & REORGANIZATION;ASSIGNOR:RAYCHEM CORPORATION, A CORPORATION OF DELAWARE;REEL/FRAME:011682/0001Effective date: 19990812Apr 5, 2001ASAssignmentFree format text: CHANGE OF NAME;ASSIGNOR:AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA /AR;REEL/FRAME:011675/0436Owner name: TYCO ELECTRONICS CORPORATION, A CORPORATION OF PENFree format text: CHANGE OF NAME;ASSIGNOR:AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA /AR;REEL/FRAME:011675/0436Effective date: 19990913Owner name: TYCO ELECTRONICS CORPORATION, A CORPORATION OF PENFree format text: CHANGE OF NAME;ASSIGNOR:AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA;REEL/FRAME:011675/0436Effective date: 19990913Owner name: TYCO ELECTRONICS CORPORATION, A CORPORATION OF PENFree format text: CHANGE OF NAME;ASSIGNOR:AMP INCORPORATED, A CORPORATION OF PENNSYLVANIA;REEL/FRAME:011675/0436Effective date: 19990913Apr 29, 2002FPAYFee paymentYear of fee payment: 4May 21, 2002REMIMaintenance fee reminder mailedMay 3, 2006FPAYFee paymentYear of fee payment: 8May 3, 2010FPAYFee paymentYear of fee payment: 12RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services