Oriented polymeric sheets exhibiting dichroism and articles containing the same

Patent metadata

Field	Value
Publication number	US-10619018-B2
Application number	US-201514740340-A
Country	US
Kind code	B2
Filing date	Jun 16, 2015
Priority date	Jul 1, 2003
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

Provided is an oriented polymeric sheet comprising a photochromic-dichroic material, wherein the sheet exhibits dichroism in an activated state. Also provided is a multilayer composite comprising at least a support layer; and an oriented thermoplastic polymeric sheet having two opposing surfaces and comprising a photochromic-dichroic material. The sheet exhibits dichroism in an activated state. At least one surface of the sheet is connected to at least a portion of the support layer. The present invention also relates to an optical element comprising the multilayer composite. Related methods also are disclosed.

First claim

We claim:

1. An oriented polymeric sheet comprising,
a first photochromic-dichroic material having a first alignment along the long-axis of said first photochromic-dichroic material in an activated state, and
at least one second photochromic-dichroic material having a second alignment along the long-axis of said second photochromic-dichroic material in said activated state that is different than said first alignment along the long-axis of said first photochromic-dichroic material,
wherein said oriented polymeric sheet is formed by,
providing a polymeric sheet comprising said first photochromic-dichroic material and said second photochromic-dichroic material, and
stretching said polymeric sheet biaxially in two or more sequential stages,

wherein the oriented polymeric sheet exhibits dichroism in said activated state,
and
wherein the first photochromic-dichroic material and the second photochromic-dichroic material each transition from a first state having a first absorbance spectrum to a second state having a second absorption spectrum different from the first absorption spectrum in response to at least actinic radiation, each revert back to the first state in response to thermal energy, and each linearly polarize at least transmitted radiation in at least the second state, the first photochromic-dichroic material and the second photochromic-dichroic material each comprising a compound having,
(a) at least one photochromic (PC) group chosen from a pyran, an oxazine, and a fulgide; and
(b) at least one lengthening agent L attached to the photochromic group and represented by:
—[S 1 ] c -[Q 1 -[S 2 ] d ] d′ -[Q 2 -[S 3 ] e ] e′ -[Q 3 -[S 4 ] f ] f′ —S 5 —P

wherein:
(i) each Q 1 , Q 2 , and Q 3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C 1 -C 18 alkoxy, poly(C 1 -C 18 alkoxy), amino, amino(C 1 -C 8 )alkylene, C 1 -C 18 alkylamino, di-(C 1 -C 18 )alkyl amino, C 1 -C 18 alkyl, C 2 -C 18 alkene, C 2 -C 18 alkyne, C 1 -C 18 alkyl(C 1 -C 18 )alkoxy, C 1 -C 18 alkoxycarbonyl, C 1 -C 18 alkylcarbonyl, C 1 -C 18 alkyl carbonate, aryl carbonate, C 1 -C 18 acetyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C 1 -C 18 alkyl group that is mono-substituted with cyano, halo, or C 1 -C 18 alkoxy, or poly-substituted with halo, and a group represented by one of the following formulae: -M(T) (t-1) and -M(OT) (t-1) , wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S 1 , S 2 , S 3 , S 4 , and S 5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) —(CH 2 ) g —, —(CF 2 ) h —, —Si(CH 2 ) g —, —(Si[(CH 3 ) 2 ]O) h —, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) —N(Z)—, —C(Z)═C(Z)—, —C(Z)═N—, —C(Z′)—C(Z′)—, wherein Z is independently chosen for each occurrence from hydrogen, C 1 -C 6 alkyl, cycloalkyl and aryl, and Z′ is independently chosen for each occurrence from C 1 -C 6 alkyl, cycloalkyl and aryl; and
(C) —O—, —C(O)—, —C≡C—, —N═N—, —S—, —S(O)—, —S(O)(O)—, straight-chain or branched C 1 -C 24 alkylene residue, said C 1 -C 24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S 1 and S 5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;

(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C 1 -C 6 )alkyl(C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, cryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and
(iv) d′, e′ and f′ are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d′+e′+f′ is at least 3,

wherein said oriented polymeric sheet comprises an elastomeric polymer.

2. The oriented polymeric sheet of claim 1 , wherein said oriented polymeric sheet has a desired pattern that is formed by the stretching of said polymeric sheet biaxially in two or more sequential stages.

Assignees

• Transitions Optical Inc

Inventors

• Kumar Anil
• Foller Peter C
• Park David
• Devine Declan
• Bastiaansen C W M
• Teunissen J P
• Cloonan Martin
• Higginbotham Clement L

Classifications

• B29C55/12 Primary

  biaxial · CPC title

• G02B5/305

  including organic materials, e.g. polymeric layers · CPC title

• G02F2202/14

  photochromic · CPC title

• G01N21/19

  Dichroism · CPC title

• G02B5/23 Primary

  Photochromic filters · CPC title