POLYMER COMPOUNDS AND A PREPARATION METHOD THEREOF
First Claim
Patent Images
1. A polymer compound containing at least one repeating unit represented by the following Formulae 1 to 14:
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In Formulae 1 to 14, Ar1 is a tetravalent C5-C24 arylene group or a tetravalent C5-C24 heterocyclic ring, which is substituted or unsubstituted with at least one substituent selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl and C1-C10 haloalkoxy, or two or more of which are fused together to form a condensation ring or covalently bonded to each other via a functional group selected from the group consisting of O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2 and C(═
O)NH;
Ar1′ and
Ar2 are identical to or different from each other and are each independently a bivalent C5-C24 arylene group or a bivalent C5-C24 heterocyclic ring, which is substituted or unsubstituted with at least one substituent selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl and C1-C10 haloalkoxy, or two or more of which are fused together to form a condensation ring or covalently bonded to each other via a functional group selected from the group consisting of O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2 and C(═
O)NH;
Q is O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2, C(═
O)NH, C(CH3)(CF3), C1-C6 alkyl-substituted phenyl or C1-C6 haloalkyl-substituted phenyl in which Q is linked to opposite both phenyl rings in the position of m-m, m-p, p-m or p-p;
Y″
is —
O or S;
n is an integer from 20 to 200;
m is an integer from 10 to 400; and
l is an integer from 10 to 400.
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Accused Products
Abstract
Disclosed herein are polymer compounds, a method for preparing thereof. More specifically, provided are polymer compounds with well-connected, narrow size distribution free-volume element and a method for preparing the polymer compounds by thermal rearrangement for aromatic polyimides containing ortho-positioned functional groups in the solid state.
44 Citations
19 Claims
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1. A polymer compound containing at least one repeating unit represented by the following Formulae 1 to 14:
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In Formulae 1 to 14, Ar1 is a tetravalent C5-C24 arylene group or a tetravalent C5-C24 heterocyclic ring, which is substituted or unsubstituted with at least one substituent selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl and C1-C10 haloalkoxy, or two or more of which are fused together to form a condensation ring or covalently bonded to each other via a functional group selected from the group consisting of O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2 and C(═
O)NH;Ar1′ and
Ar2 are identical to or different from each other and are each independently a bivalent C5-C24 arylene group or a bivalent C5-C24 heterocyclic ring, which is substituted or unsubstituted with at least one substituent selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl and C1-C10 haloalkoxy, or two or more of which are fused together to form a condensation ring or covalently bonded to each other via a functional group selected from the group consisting of O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2 and C(═
O)NH;Q is O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2, C(═
O)NH, C(CH3)(CF3), C1-C6 alkyl-substituted phenyl or C1-C6 haloalkyl-substituted phenyl in which Q is linked to opposite both phenyl rings in the position of m-m, m-p, p-m or p-p;Y″
is —
O or S;n is an integer from 20 to 200; m is an integer from 10 to 400; and l is an integer from 10 to 400. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
wherein X is O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2, or C(═
O)NH;
W is O, S or C(═
O); and
Z1, Z2 and Z3 are identical to or different from each other and are O, N or S.
-
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3. The polymer compound according to claim 1, wherein Ar1 is selected from the following compounds:
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4. The polymer compound according to claim 1, wherein Ar1′
- and Ar2 are selected from the following compounds;
wherein X is O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q (in which 1≦
q≦
10), C(CH3)2, C(CF3)2, or C(═
O)NH;
W is O, S or C(═
O); and
Z1, Z2 and Z3 are identical to or different from each other and are O, N or S.
- and Ar2 are selected from the following compounds;
-
5. The polymer compound according to claim 1, wherein Ar1′
- and Ar2 are selected from the following compounds;
- and Ar2 are selected from the following compounds;
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6. The polymer compound according to claim 1, wherein Q is selected from the group consisting of CH2, C(CH3)2, C(CF3)2, O, S, S(═
- O)2 and C(═
O).
- O)2 and C(═
-
7. The polymer compound according to claim 1, wherein Ar1 is
Ar1′ - is
Ar2 is and Q is C(CF3)2.
- is
-
8. The polymer compound according to claim 1, wherein the polymer compound is treated by an acidic dopant.
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9. The polymer compound according to claim 8, wherein the acidic dopant is selected from the group consisting of sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, HBrO3, HClO4, HPF6, HBF6, 1-methyl-3-methylimidazolium cation (BMIM+) and mixtures thereof.
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10. The polymer compound according to claim 1, wherein the polymer compound includes inorganic oxide selected from the group consisting of fumed silica, zirconium oxide, tetraethoxy silane, montmorillonite clay and mixtures thereof.
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11. The polymer compound according to claim 1, wherein the polymer compound includes inorganic filler selected from the group consisting of phosphotungstic acid (PWA), phosphomolybdenic acid, silicotungstic acid (SiWA), molybdophosphoric acid, silicomolybdic acid, phosphotin acid, zirconium phosphate (ZrP) and mixtures thereof.
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12. The polymer compound according to claim 1, wherein the polymer compound has a fractional free volume (FFV) of 0.18 to 0.40.
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13. The polymer compound according to claim 1, wherein the polymer compound has a d-spacing of 0.58 to 0.80 nm.
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14. The polymer compound according to claim 1, wherein the polymer compound has a cavity radius difference of 0.1 to 0.4 Å
- between maximum cavity radius and minimum cavity radius.
-
15. A method for preparing the polymer compound of claim 1 comprising:
-
thermally treating polyimides represented by the following Formulae 15 to 32. In Formulae 15 to 32, Ar1 is a tetravalent C5-C24 arylene group or a tetravalent C5-C24 heterocyclic ring, which is substituted or unsubstituted with at least one substituent selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl and C1-C10 haloalkoxy, or two or more of which are fused together to form a condensation ring or covalently bonded to each other via a functional group selected from the group consisting of O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2 and C(═
O)NH;Ar2 is a bivalent C5-C24 arylene group or a bivalent C5-C24 heterocyclic ring, which is substituted or unsubstituted with at least one substituent selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl and C1-C10 haloalkoxy, or two or more of which are fused together to form a condensation ring or covalently bonded to each other via a functional group selected from the group consisting of O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q, (in which 1≦
q≦
10), C(CH3)2, C(CF3)2 and C(═
O)NH;Q is O, S, C(═
O), CH(OH), S(═
O)2, Si(CH3)2, (CH2)p (in which 1≦
p≦
10), (CF2)q (in which 1≦
q≦
10), C(CH3)2, C(CF3)2, C(═
O)NH, C(CH3)(CF3), C1-C6 alkyl-substituted phenyl or C1-C6 haloalkyl-substituted phenyl in which Q is linked to opposite both phenyl rings in the position of m-m, m-p, p-m or p-p;Y is —
OH, —
SH or —
NH2;Y′
is different from Y and is —
OH, —
SH or —
NH2;n is an integer from 20 to 200; m is an integer from 10 to 400; and l is an integer from 10 to 400.
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16. The method according to claim 15, wherein the thermal treatment is carried out at 350 to 500°
- C. for 1 minute to 12 hours under an inert atmosphere.
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17. The method according to claim 15, wherein the thermal treatment is carried out at 400 to 450°
- C. for 10 minutes to 2 hours under an inert atmosphere.
-
18. The method according to claim 15, wherein the polyimides represented by Formulae 15 to 32 are obtained by imidization of polyamic acids represented by Formulae 33 to 50 below:
In Formulae 33 to 50, Ar1, Ar2, Q, Y, n, m and l are defined as above; and Y′
is different from Y and is —
OH, —
SH or —
NH2;
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19. The method according to claim 19, wherein the imidization performs chemical imidization method, thermal imidization method or solution-thermal imidization method.
Specification
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Current AssigneeIndustry-University Cooperation Foundation Hanyang University
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Original AssigneeIndustry-University Cooperation Foundation Hanyang University
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InventorsLEE, Young-Moo, Jung, Chul-Ho, Park, Ho-Bum, Han, Sang-Hoon
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current524/261
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CPC Class CodesC08F 214/18 Monomers containing fluorineC08F 222/36 Amides or imidesC08G 73/10 Polyimides; Polyester-imide...C08G 73/18 Polybenzimidazoles
