CA2647325C - Methods and systems for preparing antimicrobial bridged polycyclic compounds - Google Patents
Methods and systems for preparing antimicrobial bridged polycyclic compounds Download PDFInfo
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- CA2647325C CA2647325C CA2647325A CA2647325A CA2647325C CA 2647325 C CA2647325 C CA 2647325C CA 2647325 A CA2647325 A CA 2647325A CA 2647325 A CA2647325 A CA 2647325A CA 2647325 C CA2647325 C CA 2647325C
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- chemical compound
- alkyl
- compound
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 141
- 238000000034 method Methods 0.000 title abstract description 121
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 98
- 239000000203 mixture Substances 0.000 claims abstract description 190
- 238000000576 coating method Methods 0.000 claims abstract description 140
- 239000011248 coating agent Substances 0.000 claims abstract description 110
- 239000004599 antimicrobial Substances 0.000 claims abstract description 71
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 38
- -1 polymethylene chains Polymers 0.000 claims description 358
- 150000001875 compounds Chemical class 0.000 claims description 299
- 125000000623 heterocyclic group Chemical group 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 131
- 125000001424 substituent group Chemical group 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 239000000126 substance Substances 0.000 claims description 88
- 125000003107 substituted aryl group Chemical group 0.000 claims description 77
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 76
- 229920000642 polymer Polymers 0.000 claims description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 48
- 125000000732 arylene group Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 150000002500 ions Chemical class 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
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- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 238000005859 coupling reaction Methods 0.000 claims description 26
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- 230000008878 coupling Effects 0.000 claims description 25
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000004442 acylamino group Chemical group 0.000 claims description 22
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
- 229940124530 sulfonamide Drugs 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 13
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
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- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 7
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- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 7
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
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- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 abstract description 48
- 238000004140 cleaning Methods 0.000 abstract description 36
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 117
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| US60/755,292 | 2005-12-30 | ||
| US75640106P | 2006-01-05 | 2006-01-05 | |
| US60/756,401 | 2006-01-05 | ||
| PCT/US2006/061936 WO2007070801A2 (en) | 2005-12-12 | 2006-12-12 | Methods and systems for preparing antimicrobial films and coatings |
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| CA2647325C true CA2647325C (en) | 2015-03-24 |
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| WO2022040799A1 (en) * | 2020-08-27 | 2022-03-03 | Gp Tech Inovasyon Teknoloji Ve Arastirma A.S | Antimicrobial composition |
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2010
- 2010-05-06 US US12/775,277 patent/US9212286B2/en active Active
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2012
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022040799A1 (en) * | 2020-08-27 | 2022-03-03 | Gp Tech Inovasyon Teknoloji Ve Arastirma A.S | Antimicrobial composition |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080020127A1 (en) | 2008-01-24 |
| WO2007070801A3 (en) | 2007-11-08 |
| NZ569756A (en) | 2011-07-29 |
| US9957395B2 (en) | 2018-05-01 |
| US20110015300A1 (en) | 2011-01-20 |
| US20080021212A1 (en) | 2008-01-24 |
| EP1973587B1 (en) | 2019-02-06 |
| US20130150809A1 (en) | 2013-06-13 |
| EP1973587A2 (en) | 2008-10-01 |
| CA2647325A1 (en) | 2007-06-21 |
| AU2006325820A1 (en) | 2007-06-21 |
| EP1973587A4 (en) | 2012-12-19 |
| AU2006325820B2 (en) | 2013-02-14 |
| US20070202342A1 (en) | 2007-08-30 |
| US7713955B2 (en) | 2010-05-11 |
| US8067402B2 (en) | 2011-11-29 |
| US20080207581A1 (en) | 2008-08-28 |
| US8268381B2 (en) | 2012-09-18 |
| US9212286B2 (en) | 2015-12-15 |
| US8067403B2 (en) | 2011-11-29 |
| WO2007070801A2 (en) | 2007-06-21 |
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