US 12,252,603 B2
Regioselectively substituted cellulose ester based C+ compensation films with improved wavelength dispersion
Qianqian Zhang, Kingsport, TN (US); Bin Wang, Kingsport, TN (US); Robert Jacks Sharpe, Madison, AL (US); Wesley Wayne McConnell, Gray, TN (US); Casey Lynn Elkins, Kingsport, TN (US); and Charles Michael Buchanan, Bluff City, TN (US)
Assigned to Eastman Chemical Company, Kingsport, TN (US)
Appl. No. 17/760,458
Filed by Eastman Chemical Company, Kingsport, TN (US)
PCT Filed Feb. 10, 2021, PCT No. PCT/US2021/017363
§ 371(c)(1), (2) Date Aug. 10, 2022,
PCT Pub. No. WO2021/163121, PCT Pub. Date Aug. 19, 2021.
Claims priority of provisional application 62/975,873, filed on Feb. 13, 2020.
Prior Publication US 2023/0138841 A1, May 4, 2023
Int. Cl. C08L 1/32 (2006.01); C08J 5/18 (2006.01); C08K 5/07 (2006.01); C08K 5/3492 (2006.01); G02B 5/30 (2006.01)
CPC C08L 1/32 (2013.01) [C08J 5/18 (2013.01); C08K 5/07 (2013.01); C08K 5/3492 (2013.01); C08J 2301/32 (2013.01); C08L 2203/16 (2013.01); G02B 5/3083 (2013.01)] 12 Claims
OG exemplary drawing
 
1. 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 to 0.7,
the degree of substitution for the aromatic-CO-substituent (“DSArco”) is from 0.8 to 1.6,
the degree of substitution for the (C1-6)alkyl-CO— substituent (“DSAK”) is from 0.9-2.2, and
the plurality of aromatic-CO-— is an (C6-20) aryl-CO—, wherein the aryl is unsubstituted or substituted by 1-5 R1; and
(2) a component A that is

OG Complex Work Unit Chemistry
wherein:
ring A is an (C6-20)aryl or a 5 to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S;
ring B is (C6-20)aryl or 5 to 10 membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S;
ring C is (C6-20)aryl; or 5 to 10 membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S;
R1 is alkyl, haloalkyl, (C6-20)aryl optionally by 1-5 substituted by alkyl, haloalkyl, alkoxy, haloalkoxy, halo; 5 to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S; —CH2C(O)—R3;
R2 is independently hydrogen, alkyl, or haloalkyl;
R3 is alkyl, haloalkyl, (C6-20)aryl, or 5 to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S, wherein the aryl or heteroaryl are unsubstituted or substituted by 1-5 R6; R4 is (C1-20) alkyl, halo (C1-20) alkyl, (C1-20)alkyl-CO—(C1-20)alkyl,
wherein each is unsubstituted or substituted by 1-3 hydroxyl, (C1-20)alkoxyl, or halo (C1-20)alkoxyl. hydroxy(C1-20)alkyl, (C1-20)alkoxy-(C1-20)alkyl, (C1-20)alkoxy -hydroxy (C1-20)alkyl, or (C1-20)alkoxy-(C1-20)alkyl—CO—(C1-20)alkyl-;
each R5 is independently hydroxy, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, or halo;
each R6 is independently hydroxy, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, or halo or (C6-20)aryl, wherein the aryl is unsubstituted or substituted by 1-5 R7;
each R7 is independently hydroxyl, (C1-6)alkyl, halo(C1-6)alkyl, or (C1-6)alkoxyl;
R8 is R4—O—, (C1-20)alkyl, halo(C1-20)alkyl, (C1-20)alkyl-CO—(C1-20)alkyl-, (C1-20)alkenyl, (C1-20)alkenyl-O—, (C1-20)alkyl-COO—(C1-20)alkyl-, (C1-20)alkyl—COO—, (C1-20)alkyl, wherein 1-2 carbon atoms are replaced by O, N, or S, (C6-10) aryl, 5- to 10-membered heteroaryl containing 1-4 heteroatoms selected from the group consisting of N, O, and S,
wherein each of the groups are unsubstituted or substituted by 1-3 hydroxyl, (C1-20) alkoxyl, or halo(C1-20)alkoxyl. hydroxy(C1-20)alkyl, (C1-20)alkoxy—(C1-20)alkyl, (C1-20)alkoxy-hydroxy(C1-20)alkyl, or (C1-20)alkoxy-(C1-20)alkyl-CO—(C1-20)alkyl-;
each m is 1, 2, 3, 4 or 5;
n is 1, 2, 3, 4, or 5,
wherein:
the component A is present from 1 wt % to 30 wt %, based on the total weight of the composition,
the thickness of the film (“d”) in microns is from 1 μm to 200 μm,
the film exhibits a Re (589 nm) that is in the range of −10 nm to 10 nm,
the ratio of the Rth (589 nm) and d (nm) multiplied by 103 is greater than 1.0,
the Re l (589 nm) is the in-plane retardation measured at 589 nm,
the Rth(589 nm) is the out-of-plane retardation measured at 589 nm.