JPH0323582B2 - - Google Patents
Info
- Publication number
- JPH0323582B2 JPH0323582B2 JP27168687A JP27168687A JPH0323582B2 JP H0323582 B2 JPH0323582 B2 JP H0323582B2 JP 27168687 A JP27168687 A JP 27168687A JP 27168687 A JP27168687 A JP 27168687A JP H0323582 B2 JPH0323582 B2 JP H0323582B2
- Authority
- JP
- Japan
- Prior art keywords
- block copolymer
- adhesive
- weight
- hydrogenated block
- hydrogenated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001400 block copolymer Polymers 0.000 claims description 56
- -1 vinyl aromatic compounds Chemical class 0.000 claims description 45
- 239000000853 adhesive Substances 0.000 claims description 41
- 230000001070 adhesive effect Effects 0.000 claims description 41
- 229920002554 vinyl polymer Polymers 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000003700 epoxy group Chemical group 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000002998 adhesive polymer Substances 0.000 description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 238000009826 distribution Methods 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 229920002725 thermoplastic elastomer Polymers 0.000 description 4
- 238000013022 venting Methods 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006011 modification reaction Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005672 polyolefin resin Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000007765 extrusion coating Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- WQJUBZMZVKITBU-UHFFFAOYSA-N (3,4-dimethyl-4-phenylhexan-3-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(CC)C(C)(CC)C1=CC=CC=C1 WQJUBZMZVKITBU-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- NYOMUYWTCCBHQC-NSCUHMNNSA-N (E)-4-[1-(oxiran-2-yl)ethoxy]-4-oxobut-2-enoic acid Chemical compound OC(=O)/C=C/C(=O)OC(C)C1CO1 NYOMUYWTCCBHQC-NSCUHMNNSA-N 0.000 description 1
- YGMFIHATRQXGFA-ONEGZZNKSA-N (E)-4-[2-methyl-1-(oxiran-2-yl)propoxy]-4-oxobut-2-enoic acid Chemical compound OC(=O)/C=C/C(=O)OC(C(C)C)C1CO1 YGMFIHATRQXGFA-ONEGZZNKSA-N 0.000 description 1
- PVHXENUVKCPUTF-PLNGDYQASA-N (Z)-4-[2,2-dimethyl-1-(oxiran-2-yl)propoxy]-4-oxobut-2-enoic acid Chemical compound CC(C)(C)C(C1CO1)OC(=O)/C=C\C(=O)O PVHXENUVKCPUTF-PLNGDYQASA-N 0.000 description 1
- YGMFIHATRQXGFA-ARJAWSKDSA-N (Z)-4-[2-methyl-1-(oxiran-2-yl)propoxy]-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC(C(C)C)C1CO1 YGMFIHATRQXGFA-ARJAWSKDSA-N 0.000 description 1
- NYOMUYWTCCBHQC-IHWYPQMZSA-N (z)-4-[1-(oxiran-2-yl)ethoxy]-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC(C)C1CO1 NYOMUYWTCCBHQC-IHWYPQMZSA-N 0.000 description 1
- PYOLJOJPIPCRDP-UHFFFAOYSA-N 1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1 PYOLJOJPIPCRDP-UHFFFAOYSA-N 0.000 description 1
- XMGJKSGJGACOMI-UHFFFAOYSA-N 1-bromo-2-[3-(2-bromophenyl)butan-2-yl]benzene Chemical compound BrC1=C(C=CC=C1)C(C)C(C)C1=C(C=CC=C1)Br XMGJKSGJGACOMI-UHFFFAOYSA-N 0.000 description 1
- SBBKUBSYOVDBBC-UHFFFAOYSA-N 1-butyl-4-methylbenzene Chemical compound CCCCC1=CC=C(C)C=C1 SBBKUBSYOVDBBC-UHFFFAOYSA-N 0.000 description 1
- SFUDBXKBPOKIIW-ARJAWSKDSA-N 1-o-ethyl 4-o-(oxiran-2-ylmethyl) (z)-but-2-enedioate Chemical compound CCOC(=O)\C=C/C(=O)OCC1CO1 SFUDBXKBPOKIIW-ARJAWSKDSA-N 0.000 description 1
- SZFDQMKAGLCYPA-UHFFFAOYSA-N 1-phenylbutylbenzene Chemical compound C=1C=CC=CC=1C(CCC)C1=CC=CC=C1 SZFDQMKAGLCYPA-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- NMSZFQAFWHFSPE-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxycarbonyl)but-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OCC1CO1 NMSZFQAFWHFSPE-UHFFFAOYSA-N 0.000 description 1
- SXGGTMKKTMUBTE-UHFFFAOYSA-N 3-[1-(oxiran-2-yl)ethoxycarbonyl]but-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC(C)C1CO1 SXGGTMKKTMUBTE-UHFFFAOYSA-N 0.000 description 1
- ZWIJBAZQXSDQTJ-UHFFFAOYSA-N 3-[2-methyl-1-(oxiran-2-yl)propoxy]carbonylbut-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OC(C(C)C)C1CO1 ZWIJBAZQXSDQTJ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MLVSWIXRZNPEKF-OWOJBTEDSA-N bis(oxiran-2-ylmethyl) (e)-but-2-enedioate Chemical compound C1OC1COC(=O)/C=C/C(=O)OCC1CO1 MLVSWIXRZNPEKF-OWOJBTEDSA-N 0.000 description 1
- MLVSWIXRZNPEKF-UPHRSURJSA-N bis(oxiran-2-ylmethyl) (z)-but-2-enedioate Chemical compound C1OC1COC(=O)\C=C/C(=O)OCC1CO1 MLVSWIXRZNPEKF-UPHRSURJSA-N 0.000 description 1
- NRTSLUOVGBFANI-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) 2-methylidenebutanedioate Chemical compound C1OC1COC(=O)C(=C)CC(=O)OCC1CO1 NRTSLUOVGBFANI-UHFFFAOYSA-N 0.000 description 1
- WYLFIJGVMZESQI-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) 2-methylidenepentanedioate Chemical compound C1OC1COC(=O)C(=C)CCC(=O)OCC1CO1 WYLFIJGVMZESQI-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- BXIQXYOPGBXIEM-UHFFFAOYSA-N butyl 4,4-bis(tert-butylperoxy)pentanoate Chemical compound CCCCOC(=O)CCC(C)(OOC(C)(C)C)OOC(C)(C)C BXIQXYOPGBXIEM-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000009503 electrostatic coating Methods 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27168687A JPH01115978A (ja) | 1987-10-29 | 1987-10-29 | 接着剤 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27168687A JPH01115978A (ja) | 1987-10-29 | 1987-10-29 | 接着剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01115978A JPH01115978A (ja) | 1989-05-09 |
JPH0323582B2 true JPH0323582B2 (US07860544-20101228-C00003.png) | 1991-03-29 |
Family
ID=17503441
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP27168687A Granted JPH01115978A (ja) | 1987-10-29 | 1987-10-29 | 接着剤 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH01115978A (US07860544-20101228-C00003.png) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5399626A (en) * | 1991-04-29 | 1995-03-21 | Shell Oil Company | Viscous conjugated diene block copolymers |
US5229464A (en) * | 1991-04-29 | 1993-07-20 | Shell Oil Company | Epoxidized viscous conjugated diene block copolymers |
US5382604A (en) * | 1991-10-07 | 1995-01-17 | Shell Oil Company | Crosslinked epoxy functionalized polydiene block polymers and adhesives |
US5686535A (en) * | 1991-04-29 | 1997-11-11 | Shell Oil Company | Viscous conjugated diene block copolymers |
US5247026A (en) * | 1992-06-19 | 1993-09-21 | Shell Oil Company | Randomly epoxidized small star polymers |
US5536772A (en) * | 1993-06-18 | 1996-07-16 | Shell Oil Company | Radiation cured conjugated diene block copolymer compositions |
USH1517H (en) * | 1993-07-12 | 1996-02-06 | Shell Oil Company | Radiation curable printing ink composition |
EP1961778B1 (en) * | 2005-12-14 | 2018-12-05 | Kuraray Co., Ltd. | Block copolymer and hydrogenated product thereof |
KR20130008045A (ko) * | 2010-03-16 | 2013-01-21 | 닛토덴코 가부시키가이샤 | 점접착제층 부착 광학 시트, 점접착제층 부착 광학 시트의 제조 방법, 점접착제층 부착 광학 시트를 이용한 광원, 점접착제층 부착 광학 시트를 이용한 화상 표시 장치 |
JP6568275B2 (ja) * | 2018-08-22 | 2019-08-28 | 日本エラストマー株式会社 | 分岐材、重合体組成物の製造方法及び重合体組成物 |
-
1987
- 1987-10-29 JP JP27168687A patent/JPH01115978A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPH01115978A (ja) | 1989-05-09 |
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Legal Events
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