JP5725712B2 - 化学変性による表面特性の調整制御 - Google Patents
化学変性による表面特性の調整制御 Download PDFInfo
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- JP5725712B2 JP5725712B2 JP2009525106A JP2009525106A JP5725712B2 JP 5725712 B2 JP5725712 B2 JP 5725712B2 JP 2009525106 A JP2009525106 A JP 2009525106A JP 2009525106 A JP2009525106 A JP 2009525106A JP 5725712 B2 JP5725712 B2 JP 5725712B2
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- Prior art keywords
- alkyl
- aryl
- arylene
- group
- alkylene
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- 238000007385 chemical modification Methods 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims description 360
- 125000000217 alkyl group Chemical group 0.000 claims description 327
- 239000000758 substrate Substances 0.000 claims description 187
- 125000001072 heteroaryl group Chemical group 0.000 claims description 170
- 125000000732 arylene group Chemical group 0.000 claims description 166
- 229910052799 carbon Inorganic materials 0.000 claims description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims description 160
- 230000001070 adhesive effect Effects 0.000 claims description 154
- 239000000853 adhesive Substances 0.000 claims description 150
- 239000002243 precursor Substances 0.000 claims description 143
- 229910052760 oxygen Inorganic materials 0.000 claims description 127
- -1 cyano, amino Chemical group 0.000 claims description 119
- 125000000524 functional group Chemical group 0.000 claims description 112
- 125000000623 heterocyclic group Chemical group 0.000 claims description 109
- 150000003839 salts Chemical class 0.000 claims description 106
- 229910052717 sulfur Inorganic materials 0.000 claims description 105
- 125000003282 alkyl amino group Chemical group 0.000 claims description 99
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 91
- 229910052751 metal Inorganic materials 0.000 claims description 84
- 239000002184 metal Substances 0.000 claims description 84
- 229920000642 polymer Polymers 0.000 claims description 80
- 125000002947 alkylene group Chemical group 0.000 claims description 72
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 66
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 61
- 125000004414 alkyl thio group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000004104 aryloxy group Chemical group 0.000 claims description 55
- 125000005110 aryl thio group Chemical group 0.000 claims description 54
- 125000004986 diarylamino group Chemical group 0.000 claims description 54
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 47
- 150000002148 esters Chemical class 0.000 claims description 44
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 42
- 125000001769 aryl amino group Chemical group 0.000 claims description 42
- 229910045601 alloy Inorganic materials 0.000 claims description 40
- 239000000956 alloy Substances 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 238000004519 manufacturing process Methods 0.000 claims description 39
- 150000001408 amides Chemical class 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 239000012048 reactive intermediate Substances 0.000 claims description 30
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 26
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 23
- 150000003573 thiols Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000000468 ketone group Chemical group 0.000 claims description 21
- 229930194542 Keto Natural products 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 159000000007 calcium salts Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
- 239000002105 nanoparticle Substances 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- SZOKREAZWPYRCB-UHFFFAOYSA-N [4-[diazo(phenyl)methyl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C(=[N+]=[N-])C1=CC=CC=C1 SZOKREAZWPYRCB-UHFFFAOYSA-N 0.000 claims description 14
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
- 229910010272 inorganic material Inorganic materials 0.000 claims description 14
- 239000011147 inorganic material Substances 0.000 claims description 14
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- LNHHGTQAAIRWIU-UHFFFAOYSA-N 1-[diazo(phenyl)methyl]-4-(diethoxyphosphorylmethyl)benzene Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C(=[N+]=[N-])C1=CC=CC=C1 LNHHGTQAAIRWIU-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000010419 fine particle Substances 0.000 claims description 10
- 239000011859 microparticle Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 9
- 239000002071 nanotube Substances 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- 229920000058 polyacrylate Polymers 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 7
- DCWLXAJSZTVBJO-UHFFFAOYSA-N C(C)(=O)NCCC1=C(C=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1 Chemical compound C(C)(=O)NCCC1=C(C=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1 DCWLXAJSZTVBJO-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 229920002492 poly(sulfone) Polymers 0.000 claims description 6
- 229920000647 polyepoxide Polymers 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 229920001721 polyimide Polymers 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- 229920005992 thermoplastic resin Polymers 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 229910021387 carbon allotrope Inorganic materials 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920001470 polyketone Polymers 0.000 claims description 3
- 229920001184 polypeptide Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 239000005060 rubber Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- HLZLZWREBWOZCZ-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound O1C2C(C(=O)O)CC1C=C2 HLZLZWREBWOZCZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229920006295 polythiol Polymers 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims 1
- 239000004810 polytetrafluoroethylene Substances 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
- 239000000243 solution Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- 125000005842 heteroatom Chemical group 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RYULULVJWLRDQH-UHFFFAOYSA-N [4-(bromomethyl)phenyl]-phenylmethanone Chemical compound C1=CC(CBr)=CC=C1C(=O)C1=CC=CC=C1 RYULULVJWLRDQH-UHFFFAOYSA-N 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000004132 cross linking Methods 0.000 description 15
- 150000002739 metals Chemical class 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 13
- YZHGHGHCDSLOBP-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]-phenylmethanone Chemical compound C1=CC(CO)=CC=C1C(=O)C1=CC=CC=C1 YZHGHGHCDSLOBP-UHFFFAOYSA-N 0.000 description 13
- 125000002843 carboxylic acid group Chemical group 0.000 description 13
- 125000006413 ring segment Chemical group 0.000 description 13
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KIZFHUJKFSNWKO-UHFFFAOYSA-M calcium monohydroxide Chemical compound [Ca]O KIZFHUJKFSNWKO-UHFFFAOYSA-M 0.000 description 10
- 125000000542 sulfonic acid group Chemical group 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001994 activation Methods 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CAWWBGGPLHIRHC-UHFFFAOYSA-N [4-[diazo(phenyl)methyl]phenyl]methyl 7-oxabicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C=1C=C(COC(=O)C2C3OC(C=C3)C2)C=CC=1C(=[N+]=[N-])C1=CC=CC=C1 CAWWBGGPLHIRHC-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 description 8
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000000269 nucleophilic effect Effects 0.000 description 8
- 150000008366 benzophenones Chemical class 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- LJKIORZJGPINEV-UHFFFAOYSA-N phenyl-[4-(prop-2-enoxymethyl)phenyl]methanone Chemical compound C1=CC(COCC=C)=CC=C1C(=O)C1=CC=CC=C1 LJKIORZJGPINEV-UHFFFAOYSA-N 0.000 description 7
- 125000003107 substituted aryl group Chemical group 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 5
- UDMZSDUVAIIRHH-UHFFFAOYSA-N 4-[[4-[diazo(phenyl)methyl]phenyl]methoxy]-1,2-dimethoxybenzene Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CC=C(C(=[N+]=[N-])C=2C=CC=CC=2)C=C1 UDMZSDUVAIIRHH-UHFFFAOYSA-N 0.000 description 5
- DEZLVVUQKHTQCF-UHFFFAOYSA-N C1=C(OC)C(OC)=CC=C1OCC1=CC=C(C(=NN)C=2C=CC=CC=2)C=C1 Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CC=C(C(=NN)C=2C=CC=CC=2)C=C1 DEZLVVUQKHTQCF-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- DXNSGYZNUYPASW-UHFFFAOYSA-N [4-(c-phenylcarbonohydrazonoyl)phenyl]methanol Chemical compound C=1C=C(CO)C=CC=1C(=NN)C1=CC=CC=C1 DXNSGYZNUYPASW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- OMAAXMJMHFXYFY-UHFFFAOYSA-L calcium trioxidophosphanium Chemical compound [Ca+2].[O-]P([O-])=O OMAAXMJMHFXYFY-UHFFFAOYSA-L 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 229910052745 lead Inorganic materials 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 238000001465 metallisation Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- JRGJKWJJFXZEHI-UHFFFAOYSA-N n-ethyl-n-[2-[[4-(c-phenylcarbonohydrazonoyl)phenyl]methoxy]ethyl]aniline Chemical compound C=1C=CC=CC=1N(CC)CCOCC(C=C1)=CC=C1C(=NN)C1=CC=CC=C1 JRGJKWJJFXZEHI-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000005096 rolling process Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000000565 sulfonamide group Chemical group 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- QBGLYCVIVWIZKC-UHFFFAOYSA-N 1-phenyl-3-[2-[[4-(c-phenylcarbonohydrazonoyl)phenyl]methoxy]ethyl]urea Chemical compound C=1C=C(COCCNC(=O)NC=2C=CC=CC=2)C=CC=1C(=NN)C1=CC=CC=C1 QBGLYCVIVWIZKC-UHFFFAOYSA-N 0.000 description 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- LJGIWAVQIXBEKV-UHFFFAOYSA-N N-[2-[4-[C-[4-(2-acetamidoethyl)phenyl]carbonohydrazonoyl]phenyl]ethyl]acetamide Chemical compound C1=CC(CCNC(=O)C)=CC=C1C(=NN)C1=CC=C(CCNC(C)=O)C=C1 LJGIWAVQIXBEKV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- MCLLSIOYBXJHAW-UHFFFAOYSA-N n-[2-[[4-[diazo(phenyl)methyl]phenyl]methoxy]ethyl]-n-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CCOCC(C=C1)=CC=C1C(=[N+]=[N-])C1=CC=CC=C1 MCLLSIOYBXJHAW-UHFFFAOYSA-N 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Images
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- C—CHEMISTRY; METALLURGY
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C245/20—Diazonium compounds
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3882—Arylalkanephosphonic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
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- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
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- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/10—Treatment with macromolecular organic compounds
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
- D06M13/03—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons with unsaturated hydrocarbons, e.g. alkenes, or alkynes
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/11—Compounds containing epoxy groups or precursors thereof
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
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- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/338—Organic hydrazines; Hydrazinium compounds
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
Landscapes
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GB0616724A GB0616724D0 (en) | 2006-08-23 | 2006-08-23 | Surface adhesion using arylcarbene reactive intermediates |
| GB0616724.1 | 2006-08-23 | ||
| PCT/GB2007/003194 WO2008023170A1 (en) | 2006-08-23 | 2007-08-22 | Tailored control of surface properties by chemical modification |
Publications (3)
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| JP2010501536A JP2010501536A (ja) | 2010-01-21 |
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| JP2009525106A Active JP5725712B2 (ja) | 2006-08-23 | 2007-08-22 | 化学変性による表面特性の調整制御 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102008042718A1 (de) | 2008-10-09 | 2010-04-15 | Invendo Medical Gmbh | Medizintechnischer, elastischer Polymerschlauch und Verfahren zu seiner Herstellung |
| US10221496B2 (en) * | 2008-11-26 | 2019-03-05 | Macdermid Enthone Inc. | Copper filling of through silicon vias |
| KR101753917B1 (ko) | 2009-03-02 | 2017-07-04 | 옥스포드 어드밴스드 서패이시즈 리미티드 | 공유결합 3차원 네트워크를 형성할 수 있는 화학제 |
| WO2013012905A2 (en) | 2011-07-18 | 2013-01-24 | Celgard Llc | Surface modified polymeric materials, modified functionalized polymers, functional polymers, and methods |
| MX366743B (es) | 2012-04-13 | 2019-07-04 | Sigma Alimentos Sa De Cv | Papel o cartón hidrofóbico con nanopartículas auto-ensambladas y método para elaborarlo. |
| US8859098B2 (en) * | 2012-05-18 | 2014-10-14 | Lord Corporation | Acrylic adhesion promoters |
| JP2015534464A (ja) | 2012-10-09 | 2015-12-03 | カリフォルニア インスティチュート オブ テクノロジー | ヘム酵素によって触媒されるインビボおよびインビトロオレフィンシクロプロパン化 |
| WO2014081391A1 (en) | 2012-11-23 | 2014-05-30 | Nanyang Technological University | New photoactive bioadhesive compositions |
| CN103483554B (zh) | 2013-09-24 | 2015-12-02 | 艾达索高新材料无锡有限公司 | 可降解腙类环氧树脂固化剂及其应用 |
| US11357884B2 (en) | 2014-01-14 | 2022-06-14 | Nanyang Technological University | Electroactive bioadhesive compositions |
| TWI648271B (zh) | 2014-09-23 | 2019-01-21 | 日商住友電木股份有限公司 | 二氮環丙烯化合物及由其衍生之組成物 |
| US9899212B2 (en) * | 2015-04-17 | 2018-02-20 | The University Of Rochester | Methods for depositing a monolayer on a substrate |
| EP3472247A1 (en) * | 2016-06-20 | 2019-04-24 | Université de Mons | Omniphobic surface coatings |
| CN108400085B (zh) * | 2017-02-06 | 2019-11-19 | 联华电子股份有限公司 | 形成半导体元件图案的方法 |
| CN107082905B (zh) * | 2017-05-15 | 2019-12-27 | 齐鲁工业大学 | 紫外光照射后修饰法制备聚氨酯-纳米银长效抗菌薄膜的方法 |
| CN107163277B (zh) * | 2017-05-15 | 2019-12-27 | 齐鲁工业大学 | 一种紫外光照射制备疏水性聚氨酯薄膜的方法 |
| JP7178094B2 (ja) * | 2019-03-05 | 2022-11-25 | 国立大学法人岩手大学 | 反応性付与化合物、その製造方法、それを用いた表面反応性固体、及び表面反応性固体の製造方法 |
| US11274227B1 (en) * | 2019-08-06 | 2022-03-15 | Oceanit Laboratories, Inc. | Oil and water resistant low adhesion surface treatment and coatings |
| WO2021233959A1 (en) * | 2020-05-19 | 2021-11-25 | Universite De Nantes | Chemical functionalization of cellulosic materials with diazo compounds |
| CA3223390A1 (en) | 2021-08-17 | 2023-02-23 | Colin Brown | Methods and compositions for identifying methylated cytosines |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA812736A (en) | 1969-05-13 | A. Olsen Douglas | Carbene modified organic surfaces | |
| US2710862A (en) * | 1953-12-08 | 1955-06-14 | Schenley Ind Inc | Production of diaryldiazomethanes |
| US3376278A (en) * | 1964-11-06 | 1968-04-02 | Minnesota Mining & Mfg | Process for the chemical modification of the solid surface of a polymer |
| FR1500512A (fr) | 1965-10-23 | 1967-11-03 | Archer Daniels Midland Co | Procédé de modification par un carbène de surfaces en une substance organique |
| CH636093A5 (de) | 1978-01-28 | 1983-05-13 | Ciba Geigy Ag | Mikrobizide mittel. |
| DE2902959C2 (de) * | 1979-01-26 | 1984-11-29 | Battelle-Institut E.V., 6000 Frankfurt | Verfahren zur Oberflächenmodifizierung von Kunststoffen, Azido- bzw. Diazoderivate und deren Herstellung |
| US4280819A (en) * | 1980-04-30 | 1981-07-28 | Gulf Research & Development Company | Diesel fuel compositions containing certain azides for improved cetane number |
| US5002582A (en) * | 1982-09-29 | 1991-03-26 | Bio-Metric Systems, Inc. | Preparation of polymeric surfaces via covalently attaching polymers |
| JPS6178758A (ja) | 1984-09-27 | 1986-04-22 | Taoka Chem Co Ltd | ジアゾメタン誘導体の製造方法 |
| US5154808A (en) * | 1987-06-26 | 1992-10-13 | Fuji Photo Film Co., Ltd. | Functional organic thin film and process for producing the same |
| EP0425485B1 (en) | 1988-07-22 | 2000-10-04 | SurModics, Inc. | Preparation of polymeric surfaces |
| US5075427A (en) * | 1990-11-19 | 1991-12-24 | W. R. Grace & Co.-Conn. | Polymer surface modification using aqueous stable diazo solution |
| ATE212851T1 (de) * | 1993-03-12 | 2002-02-15 | Univ Auburn | Biozide polymere zyklische n-halamine |
| US5811460A (en) | 1994-01-24 | 1998-09-22 | The Regents Of The University Of California | Water soluble fullerenes with antiviral activity |
| AUPM666694A0 (en) | 1994-07-06 | 1994-07-28 | Unisearch Limited | Natural antifouling compositions |
| JP2860400B2 (ja) * | 1996-03-08 | 1999-02-24 | 工業技術院長 | 高反応性活性種の放出方法と固体表面の改質方法 |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| AUPO772097A0 (en) | 1997-07-04 | 1997-07-31 | Aquaculture Crc Limited | Antifouling polymers |
| GB9824023D0 (en) * | 1998-11-03 | 1998-12-30 | Isis Innovation | Surface functionalisation |
| EP1189643A1 (en) * | 1999-06-30 | 2002-03-27 | Novartis AG | Ophthalmic molding |
| KR20020016869A (ko) * | 1999-07-08 | 2002-03-06 | 나까니시 히로유끼 | 극성기 함유 열가소성 중합체, 그 용도 및 극성기 함유불포화 화합물 |
| CN1469785A (zh) | 2000-10-16 | 2004-01-21 | ��˹��ŵ�� | 涂敷材料表面的方法 |
| US7338805B2 (en) * | 2001-05-04 | 2008-03-04 | Bio Merieux | Labeling reagents, methods for synthesizing such reagents and methods for detecting biological molecules |
| FR2824323B1 (fr) | 2001-05-04 | 2008-04-25 | Bio Merieux | Reactif de marquage et procede de detection de molecules biologiques |
| GB0322173D0 (en) | 2003-09-23 | 2003-10-22 | Secr Defence | Surface functionalised adhesion |
| GB0500895D0 (en) * | 2005-01-17 | 2005-02-23 | Isis Innovation | Biocidal surface functionalisation |
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| PL2054465T3 (pl) | 2013-01-31 |
| WO2008023170A1 (en) | 2008-02-28 |
| KR20090054446A (ko) | 2009-05-29 |
| ES2387416T3 (es) | 2012-09-21 |
| CN101558106A (zh) | 2009-10-14 |
| US8530212B2 (en) | 2013-09-10 |
| CN101558106B (zh) | 2012-10-17 |
| KR101479122B1 (ko) | 2015-01-07 |
| GB0616724D0 (en) | 2006-10-04 |
| EP2054465B1 (en) | 2012-07-11 |
| EP2054465A1 (en) | 2009-05-06 |
| US20100068783A1 (en) | 2010-03-18 |
| JP2010501536A (ja) | 2010-01-21 |
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