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US 12,703,774 B2Granted
Regioselectively substituted cellulose ester based negative birefringent compensation films having improved wavelength dispersion
AssigneeEastman Chemical Company
InventorsQianqian Zhang, Charles Michael Buchanan, Casey Lynn Elkins, Wesley Wayne McConnell, Bin Wang, Robert Jacks Sharpe, Mustafa Humbel Ahmed
Life of this patent
Estimating the term…
Abstract
The present application discloses stretched films comprising regioselectively substituted cellulose esters and a component A wherein rings A, B, C, R1, R2, R5, R6, R8, R9, m, n, and k are defined herein. The films exhibit negative birefringence and improved wavelength dispersion.
Claims20
A film, comprising:
- (1) a regioselectively substituted cellulose ester comprising:
- (i) a plurality of aromatic-CO— substituents;
- (ii) a plurality of a first unsaturated or saturated (C1-6)alkyl-CO— substituents;
- and
- (iii) a plurality of hydroxyl substituents;
- wherein:
- the degree of substitution for the hydroxyl (“DSOH”) is from 0.2 to 1.1,
- the cellulose ester has a C2 degree of substitution for the aromatic-CO— substituent (“C2DSArCO”) which is from 0.15 to 0.8,
- the cellulose ester has a C3 degree of substitution for the aromatic-CO— substituent (“C3DSArCO”) which is from 0.05 to 0.6,
- the cellulose ester has a C6 degree of substitution for the aromatic-CO— substituent (“C6DSArCO”) which is from 0.05 to 0.6,
- the total degree of substitution for the aromatic-CO— substituent (“TotDSArCO”) which is from 0.25 to 2.0,
- the aromatic-CO— is
- (i) an (C6-20)aryl-CO—, wherein the aryl is unsubstituted or substituted by 1-5 R1;
- (ii) a heteroaryl-CO—, wherein the heteroaryl is a 5- to 10-membered ring having 1- to 4-heteroatoms chosen from N, O, or S, and wherein the heteroaryl is unsubstituted or substituted by 1-5 R1;
- and
- (2) a component A that is
- wherein:
- ring A is an (C6-20)aryl or a 5- to 10-membered heteroaryl containing 1-4 heteroatoms chosen from N, O, or S;
- ring B is (C6-20)aryl or a 5- to 10-membered heteroaryl containing 1-4 heteroatoms chosen from N, O, or S;
- ring C is (C6-20)aryl a 5- to 10-membered heteroaryl containing 1-4 heteroatoms chosen from N, O, or S;
- R1 is saturated or unsaturated (C1-20)alkyl;
- saturated or unsaturated halo(C1-20)alkyl;
- (C6-20)aryl optionally by 1-5 substituted by alkyl, haloalkyl, alkoxy, haloalkoxy, halo;
- 5- to 10-membered heteroaryl containing 1-4 heteroatoms chosen from N, O, or S;
- or —CH2C(O)—R3;
- R2 is independently hydrogen, saturated or unsaturated (C1-20)alkyl, or saturated or unsaturated halo(C1-20)alkyl;
- R3 is saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, (C6-20)aryl, or 5- to 10-membered heteroaryl containing 1-4 heteroatoms chosen from N, O, or S, wherein the aryl or heteroaryl are unsubstituted or substituted by 1-5 R6;
- R4 is saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, or saturated or unsaturated (C1-20)alkyl-CO—(C1-20)alkyl, wherein each of the groups is unsubstituted or substituted by 1-3 hydroxyl, saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy, saturated or unsaturated halo(C1-20)alkoxy, saturated or unsaturated hydroxy(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-hydroxy(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl-CO—(C1-20)alkyl, saturated or unsaturated (C1-20)alkyl-CO, saturated or unsaturated (C1-20)alkyl-COO, saturated or unsaturated (C1-20)alkyl-O—CO—C(1-20)alkyl, saturated or unsaturated (C1-20)alkyl-COO—C(1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl-COO—(C1-20)alkyl, or (C1-20)alkoxy-(C1-20)alkyl-O—CO—(C1-20)alkyl;
- each R5 is independently hydroxy, cyano, saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy, saturated or unsaturated halo(C1-20)alkoxy, or halo;
- each R6 is independently hydroxy, cyano, saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy, saturated or unsaturated halo(C1-20)alkoxy, or halo or (C6-20)aryl, wherein the aryl is unsubstituted or substituted by 1-5 R7;
- each R7 is independently hydroxyl, saturated or unsaturated (C1-6)alkyl, saturated or unsaturated halo(C1-6)alkyl, or saturated or unsaturated (C1-6)alkoxyl;
- R8 is saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxyl, or saturated or unsaturated halo(C1-20)alkoxyl;
- each R9 is R4—O—, hydroxy, saturated or unsaturated (C1-20)alkyl, saturated or unsaturated hetero(C1-20)alkyl containing 1-2 heteroatoms chosen from N, O or S, saturated or unsaturated halo(C1-20)alkyl, saturated or unsaturated (C1-20)alkyl-CO—(C1-20)alkyl-, saturated or unsaturated (C1-20)alkyl-COO—(C1-20)alkyl-, saturated or unsaturated (C1-20)alkyl-COO—, saturated or unsaturated (C1-20)alkyl-O—CO—, saturated or unsaturated (C1-2)alkyl-CO—, saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl-CO— O—(C1-2)alkyl, saturated or unsaturated (C1-2)alkoxy-(C1-2)alkyl-O—CO— (C1-2)alkyl, saturated or unsaturated (C1-2)alkoxy-(C1-2)alkyl-CO— (C1-20)alkyl, (C1-20)alkoxy-(C1-20)alkyl-O—CO—(C1-20)alkyl-(C6-10)aryl, 5- to 10-membered heteroaryl containing 1-4 heteroatoms chosen from N, O, or S,
- wherein each of the groups are unsubstituted or substituted by 1-3 hydroxyl, saturated or unsaturated (C1-20)alkyl, saturated or unsaturated halo(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxyl, or saturated or unsaturated halo(C1-20)alkoxyl, saturated or unsaturated hydroxy(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-hydroxy(C1-20)alkyl, or saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl-CO—(C1-20)alkyl-, saturated or unsaturated (C1-20)alkyl-CO, saturated or unsaturated (C1-20)alkyl-COO, saturated or unsaturated (C1-20)alkyl-O—CO—C(1-20)alkyl, saturated or unsaturated (C1-20)alkyl-COO—C(1-20)alkyl, saturated or unsaturated (C1-20)alkoxy-(C1-20)alkyl-COO—(C1-20)alkyl, or (C1-20)alkoxy-(C1-20)alkyl-O—CO—(C1-20)alkyl;
- each n is 0, 1, 2, 3, 4, or 5;
- each m is 0, 1, 2, 3, or 4;
- and
- k is 0, 1, 3, or 4,
- wherein:
- component A is present at less than 30 wt %, based on the total weight of the film,
- the thickness of the film (“d”) (μm) is from 10 μm to 200 μm,
- the film exhibits a Re(589 nm) that is less than zero,
- the ratio of the Re(589 nm) and d (nm) multiplied by 1000 is from −10 to −0.5,
- the ratio of the Rth (589 nm) and d (nm) multiplied by 1000 is from −6.0 to 6.0,
- the film exhibits a [[—Rth(589 nm)/Re(589 nm)]+0.5](“Nz”) is from −3.0 to 3.0,
- each Re(589 nm) is the in-plane retardation measured at 589 nm,
- each Rth(589 nm) is the out-of-plane retardation measured at 589 nm, and the film is stretched.
44 more elements
Dependencies are inferred from the claim text.