TWI512029B

TWI512029B - Hardened composition

Hardened composition Download PDF

Info

Publication number: TWI512029B
Authority: TW; Taiwan
Prior art keywords: group; polymer; curable composition; decane compound; synthesis example
Prior art date: 2010-10-27

Application number

TW100138649A

Other languages

English (en)

Chinese (zh)

Other versions

TW201231536A (en

Inventor

Yutaka Watanabe

Naomi Okamura

Atsushi Saito

Hirohito Mizuno

Original Assignee

Cemedine Co Ltd

Priority date

2010-10-27

Filing date

2011-10-25

Publication date

2015-12-11

2011-10-25 Application filed by Cemedine Co Ltd filed Critical Cemedine Co Ltd

2012-08-01 Publication of TW201231536A publication Critical patent/TW201231536A/zh

2015-12-11 Application granted granted Critical

2015-12-11 Publication of TWI512029B publication Critical patent/TWI512029B/zh

Links

239000000203 mixture Substances 0.000 title claims description 243
229920000642 polymer Polymers 0.000 claims description 273
-1 epoxy decane compound Chemical class 0.000 claims description 252
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 143
229910052719 titanium Inorganic materials 0.000 claims description 142
239000010936 titanium Substances 0.000 claims description 142
239000003054 catalyst Substances 0.000 claims description 137
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 128
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 110
239000000178 monomer Substances 0.000 claims description 109
238000006243 chemical reaction Methods 0.000 claims description 70
229920000620 organic polymer Polymers 0.000 claims description 64
125000003396 thiol group Chemical group [H]S* 0.000 claims description 64
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 58
229910000019 calcium carbonate Inorganic materials 0.000 claims description 54
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 52
239000005977 Ethylene Substances 0.000 claims description 52
239000000843 powder Substances 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 31
150000002430 hydrocarbons Chemical group 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
239000002245 particle Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 19
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 19
239000013522 chelant Substances 0.000 claims description 18
229920002554 vinyl polymer Polymers 0.000 claims description 17
125000003277 amino group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
239000003085 diluting agent Substances 0.000 claims description 15
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims description 14
229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 14
239000000945 filler Substances 0.000 claims description 14
229910000000 metal hydroxide Inorganic materials 0.000 claims description 14
150000004692 metal hydroxides Chemical class 0.000 claims description 14
229930195734 saturated hydrocarbon Natural products 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 9
239000007791 liquid phase Substances 0.000 claims description 9
229920000058 polyacrylate Polymers 0.000 claims description 8
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 7
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 6
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
230000000379 polymerizing effect Effects 0.000 claims description 6
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical group [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 5
229940125904 compound 1 Drugs 0.000 claims description 4
239000002994 raw material Substances 0.000 claims description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
239000010931 gold Substances 0.000 claims 1
229910052737 gold Inorganic materials 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 description 159
238000003786 synthesis reaction Methods 0.000 description 157
238000012360 testing method Methods 0.000 description 95
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 87
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
238000003756 stirring Methods 0.000 description 68
238000003860 storage Methods 0.000 description 56
235000010216 calcium carbonate Nutrition 0.000 description 54
238000000034 method Methods 0.000 description 45
239000000126 substance Substances 0.000 description 42
238000013112 stability test Methods 0.000 description 34
238000005481 NMR spectroscopy Methods 0.000 description 33
229910001873 dinitrogen Inorganic materials 0.000 description 33
229910052757 nitrogen Inorganic materials 0.000 description 30
239000003795 chemical substances by application Substances 0.000 description 27
238000010992 reflux Methods 0.000 description 27
NOGBEXBVDOCGDB-NRFIWDAESA-L (z)-4-ethoxy-4-oxobut-2-en-2-olate;propan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)[O-].CC(C)[O-].CCOC(=O)\C=C(\C)[O-].CCOC(=O)\C=C(\C)[O-] NOGBEXBVDOCGDB-NRFIWDAESA-L 0.000 description 26
QUBWTXNVPULBEW-UHFFFAOYSA-N acetic acid;butanimidamide Chemical compound CC(O)=O.CCCC(N)=N QUBWTXNVPULBEW-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 25
238000007872 degassing Methods 0.000 description 24
238000010438 heat treatment Methods 0.000 description 23
230000008859 change Effects 0.000 description 21
125000003545 alkoxy group Chemical group 0.000 description 19
229920001577 copolymer Polymers 0.000 description 19
239000000463 material Substances 0.000 description 19
229940057995 liquid paraffin Drugs 0.000 description 18
238000002156 mixing Methods 0.000 description 17
230000005070 ripening Effects 0.000 description 17
230000032683 aging Effects 0.000 description 16
150000001412 amines Chemical class 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
230000000052 comparative effect Effects 0.000 description 14
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 14
238000006116 polymerization reaction Methods 0.000 description 14
229920001296 polysiloxane Polymers 0.000 description 14
239000000047 product Substances 0.000 description 14
MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 13
235000014113 dietary fatty acids Nutrition 0.000 description 13
238000009826 distribution Methods 0.000 description 13
239000000194 fatty acid Substances 0.000 description 13
229930195729 fatty acid Natural products 0.000 description 13
238000010526 radical polymerization reaction Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
230000003449 preventive effect Effects 0.000 description 12
239000011164 primary particle Substances 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
229910000420 cerium oxide Inorganic materials 0.000 description 11
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 11
125000003700 epoxy group Chemical group 0.000 description 11
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 11
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
125000003118 aryl group Chemical group 0.000 description 10
238000001723 curing Methods 0.000 description 10
150000004665 fatty acids Chemical class 0.000 description 10
125000000524 functional group Chemical group 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
VSCVYVRTQIRCTN-UHFFFAOYSA-N COC(CCCCCCCCC)(OC)OC.C=C Chemical compound COC(CCCCCCCCC)(OC)OC.C=C VSCVYVRTQIRCTN-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000001070 adhesive effect Effects 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000003063 flame retardant Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
239000002904 solvent Substances 0.000 description 9
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
239000000853 adhesive Substances 0.000 description 8
230000000704 physical effect Effects 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
229920001451 polypropylene glycol Polymers 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
229910052707 ruthenium Inorganic materials 0.000 description 8
239000000243 solution Substances 0.000 description 8
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 description 7
XJDCHDFUMGSEHD-UHFFFAOYSA-N NCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)OC)CCCCCCCC XJDCHDFUMGSEHD-UHFFFAOYSA-N 0.000 description 7
239000011324 bead Substances 0.000 description 7
239000011575 calcium Substances 0.000 description 7
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LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
238000005259 measurement Methods 0.000 description 7
239000004014 plasticizer Substances 0.000 description 7
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 7
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 7
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
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CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 6
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238000011156 evaluation Methods 0.000 description 6
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230000035484 reaction time Effects 0.000 description 6
239000003566 sealing material Substances 0.000 description 6
238000004381 surface treatment Methods 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
239000006097 ultraviolet radiation absorber Substances 0.000 description 6
OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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239000003963 antioxidant agent Substances 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
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238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 5
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000004575 stone Substances 0.000 description 5
239000012756 surface treatment agent Substances 0.000 description 5
DFYGYTNMHPUJBY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane-1-thiol Chemical compound SCCCC(C(OC)(OC)OC)CCCCCCCC DFYGYTNMHPUJBY-UHFFFAOYSA-N 0.000 description 4
239000004593 Epoxy Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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239000004677 Nylon Substances 0.000 description 4
229920002292 Nylon 6 Polymers 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
239000005062 Polybutadiene Substances 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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230000003712 anti-aging effect Effects 0.000 description 4
230000003078 antioxidant effect Effects 0.000 description 4
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
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239000007788 liquid Substances 0.000 description 4
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239000011976 maleic acid Substances 0.000 description 4
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
239000003643 water by type Substances 0.000 description 4
239000001993 wax Substances 0.000 description 4
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ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 description 3
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NSZNOCGQPUUMSL-UHFFFAOYSA-N 2-propan-2-yloxypropane;titanium Chemical compound [Ti].CC(C)OC(C)C NSZNOCGQPUUMSL-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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239000002202 Polyethylene glycol Substances 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
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