CA2681201C - Photoactivable nitrogen bases - Google Patents
Photoactivable nitrogen bases Download PDFInfo
- Publication number
- CA2681201C CA2681201C CA2681201A CA2681201A CA2681201C CA 2681201 C CA2681201 C CA 2681201C CA 2681201 A CA2681201 A CA 2681201A CA 2681201 A CA2681201 A CA 2681201A CA 2681201 C CA2681201 C CA 2681201C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- substituted
- interrupted
- unsubstituted
- hydrogen
- 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 - Fee Related
Links
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 273
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 79
- 239000001257 hydrogen Substances 0.000 claims abstract description 78
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 47
- 150000002367 halogens Chemical class 0.000 claims abstract description 47
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 39
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 28
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 28
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims abstract description 10
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 158
- -1 amino, carboxyl Chemical group 0.000 claims description 123
- 239000002585 base Substances 0.000 claims description 113
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 62
- 239000012948 isocyanate Substances 0.000 claims description 57
- 238000002360 preparation method Methods 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- 150000002513 isocyanates Chemical class 0.000 claims description 47
- 238000000576 coating method Methods 0.000 claims description 41
- 230000008569 process Effects 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 30
- 239000007858 starting material Substances 0.000 claims description 28
- 239000000853 adhesive Substances 0.000 claims description 25
- 230000001070 adhesive effect Effects 0.000 claims description 25
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- 229920000058 polyacrylate Polymers 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006555 catalytic reaction Methods 0.000 claims description 17
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 150000003573 thiols Chemical class 0.000 claims description 15
- 229920000728 polyester Polymers 0.000 claims description 14
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 13
- 239000003822 epoxy resin Substances 0.000 claims description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 238000007259 addition reaction Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 150000002118 epoxides Chemical class 0.000 claims description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000976 ink Substances 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004653 anthracenylene group Chemical group 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 229920001281 polyalkylene Polymers 0.000 claims description 5
- 229920006295 polythiol Polymers 0.000 claims description 5
- 239000013638 trimer Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 4
- 150000004658 ketimines Chemical class 0.000 claims description 4
- 239000000206 moulding compound Substances 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 3
- 229920006243 acrylic copolymer Polymers 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 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 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 229920001744 Polyaldehyde Polymers 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000002917 oxazolidines Chemical class 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 abstract description 3
- 235000013350 formula milk Nutrition 0.000 description 109
- 239000000306 component Substances 0.000 description 90
- 238000006243 chemical reaction Methods 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 238000009472 formulation Methods 0.000 description 46
- 239000002904 solvent Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 150000003254 radicals Chemical class 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 238000001723 curing Methods 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000011248 coating agent Substances 0.000 description 24
- 231100000489 sensitizer Toxicity 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 21
- 239000000725 suspension Substances 0.000 description 20
- 238000004132 cross linking Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000012965 benzophenone Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000002156 mixing Methods 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 239000000049 pigment Substances 0.000 description 15
- 239000004814 polyurethane Substances 0.000 description 15
- 239000000654 additive Substances 0.000 description 14
- 229940024874 benzophenone Drugs 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 description 13
- LTXRZOZLUURSKO-UHFFFAOYSA-N methyl 4-(3,4,6,7,8,8a-hexahydro-2h-pyrrolo[1,2-a]pyrimidin-1-ylmethyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C2CCCN2CCC1 LTXRZOZLUURSKO-UHFFFAOYSA-N 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000005809 transesterification reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229940043232 butyl acetate Drugs 0.000 description 11
- 229940052303 ethers for general anesthesia Drugs 0.000 description 11
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 11
- 150000002989 phenols Chemical class 0.000 description 11
- 150000003077 polyols Chemical class 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 238000005755 formation reaction Methods 0.000 description 9
- 230000005855 radiation Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 150000001409 amidines Chemical class 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 229940095050 propylene Drugs 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 150000008366 benzophenones Chemical class 0.000 description 7
- 229960004132 diethyl ether Drugs 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 6
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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- 150000007513 acids Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
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- 125000000524 functional group Chemical group 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- YZYWRUFNOZZQFC-UHFFFAOYSA-N 4-(3,4,6,7,8,8a-hexahydro-2h-pyrrolo[1,2-a]pyrimidin-1-ylmethyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2CCCN2CCC1 YZYWRUFNOZZQFC-UHFFFAOYSA-N 0.000 description 5
- 238000005815 base catalysis Methods 0.000 description 5
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- 150000002540 isothiocyanates Chemical class 0.000 description 5
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- 229910000103 lithium hydride Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
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- 229910052700 potassium Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- IHGJZNUBLMAEGL-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]nonane Chemical compound N1CCCN2CCCC21 IHGJZNUBLMAEGL-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000002981 blocking agent Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229950005499 carbon tetrachloride Drugs 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
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- OAUXBAZCEXSXGL-UHFFFAOYSA-M triphenyl(phenylsulfanylmethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CSC1=CC=CC=C1 OAUXBAZCEXSXGL-UHFFFAOYSA-M 0.000 description 1
- FWYKRJUVEOBFGH-UHFFFAOYSA-M triphenyl(prop-2-enyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 FWYKRJUVEOBFGH-UHFFFAOYSA-M 0.000 description 1
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- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
- FUMBGFNGBMYHGH-UHFFFAOYSA-M triphenyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCCCC)C1=CC=CC=C1 FUMBGFNGBMYHGH-UHFFFAOYSA-M 0.000 description 1
- PPORXBBMZZFXTB-UHFFFAOYSA-M triphenyl(trimethylsilylmethyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C[Si](C)(C)C)C1=CC=CC=C1 PPORXBBMZZFXTB-UHFFFAOYSA-M 0.000 description 1
- AELWOFMTABHNQJ-UHFFFAOYSA-M triphenyl(undecyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCC)C1=CC=CC=C1 AELWOFMTABHNQJ-UHFFFAOYSA-M 0.000 description 1
- TVFYBHGFLHYJNV-GLDAUVFXSA-L triphenyl-[(e)-2-triphenylphosphaniumylethenyl]phosphanium;dibromide Chemical compound [Br-].[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)/C=C/[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 TVFYBHGFLHYJNV-GLDAUVFXSA-L 0.000 description 1
- APIBROGXENTUGB-ZUQRMPMESA-M triphenyl-[(e)-3-phenylprop-2-enyl]phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 APIBROGXENTUGB-ZUQRMPMESA-M 0.000 description 1
- NBGQQOBCTPJEFE-ZUQRMPMESA-M triphenyl-[(e)-3-phenylprop-2-enyl]phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 NBGQQOBCTPJEFE-ZUQRMPMESA-M 0.000 description 1
- OOACLPDZHDFCQP-LLIZZRELSA-L triphenyl-[(e)-4-triphenylphosphaniumylbut-2-enyl]phosphanium;dichloride Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OOACLPDZHDFCQP-LLIZZRELSA-L 0.000 description 1
- MXCBXCYGWQAOSN-UHFFFAOYSA-L triphenyl-[[2-(triphenylphosphaniumylmethyl)phenyl]methyl]phosphanium;dibromide Chemical compound [Br-].[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MXCBXCYGWQAOSN-UHFFFAOYSA-L 0.000 description 1
- IUNJPQCPINLADS-UHFFFAOYSA-L triphenyl-[[4-(triphenylphosphaniumylmethyl)phenyl]methyl]phosphanium;dichloride Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC(C=C1)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IUNJPQCPINLADS-UHFFFAOYSA-L 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
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- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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- 239000011345 viscous material Substances 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2014—Contact or film exposure of light sensitive plates such as lithographic plates or circuit boards, e.g. in a vacuum frame
- G03F7/2016—Contact mask being integral part of the photosensitive element and subject to destructive removal during post-exposure processing
- G03F7/202—Masking pattern being obtained by thermal means, e.g. laser ablation
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Ceramic Engineering (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07105510.7 | 2007-04-03 | ||
| EP07105510 | 2007-04-03 | ||
| PCT/EP2008/053456 WO2008119688A1 (en) | 2007-04-03 | 2008-03-25 | Photoactivable nitrogen bases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2681201A1 CA2681201A1 (en) | 2008-10-09 |
| CA2681201C true CA2681201C (en) | 2016-06-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2681201A Expired - Fee Related CA2681201C (en) | 2007-04-03 | 2008-03-25 | Photoactivable nitrogen bases |
Country Status (9)
| Country | Link |
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| US (3) | US9921477B2 (OSRAM) |
| EP (1) | EP2145231B1 (OSRAM) |
| JP (1) | JP5606308B2 (OSRAM) |
| KR (2) | KR101944734B1 (OSRAM) |
| CN (1) | CN101641643B (OSRAM) |
| AT (1) | ATE524765T1 (OSRAM) |
| CA (1) | CA2681201C (OSRAM) |
| MX (1) | MX2009010309A (OSRAM) |
| WO (1) | WO2008119688A1 (OSRAM) |
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| ATE524765T1 (de) | 2007-04-03 | 2011-09-15 | Basf Se | Fotoaktivierbare stickstoffbasen |
| EP2285836B1 (en) * | 2008-06-06 | 2012-01-18 | Basf Se | Photoinitiator mixtures |
| CN101967343A (zh) * | 2010-10-22 | 2011-02-09 | 广州市博兴化工科技有限公司 | 一种光固化色漆 |
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| US9758607B2 (en) | 2013-10-10 | 2017-09-12 | Research Foundation Of The City University Of New York | Polymer with antibacterial activity |
| DE102014202609B4 (de) | 2014-02-13 | 2020-06-04 | tooz technologies GmbH | Aminkatalysierte Thiolhärtung von Epoxidharzen |
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| JP6802712B2 (ja) | 2014-06-23 | 2020-12-16 | カーボン，インコーポレイテッド | 三次元物体の製造に使用する多様な硬化機構を有するポリウレタン樹脂 |
| JP6731930B2 (ja) | 2015-02-05 | 2020-07-29 | カーボン，インコーポレイテッド | 断続的曝露による付加製造方法 |
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| JP7069006B2 (ja) | 2015-09-04 | 2022-05-17 | カーボン，インコーポレイテッド | 積層造形用シアネートエステル二重硬化樹脂 |
| CN108291011B (zh) | 2015-09-09 | 2021-03-02 | 卡本有限公司 | 用于增材制造的环氧双重固化树脂 |
| US10647873B2 (en) | 2015-10-30 | 2020-05-12 | Carbon, Inc. | Dual cure article of manufacture with portions of differing solubility |
| US11891485B2 (en) | 2015-11-05 | 2024-02-06 | Carbon, Inc. | Silicone dual cure resins for additive manufacturing |
| WO2017112571A1 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Dual cure additive manufacturing of rigid intermediates that generate semi-rigid, flexible, or elastic final products |
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| US10501572B2 (en) | 2015-12-22 | 2019-12-10 | Carbon, Inc. | Cyclic ester dual cure resins for additive manufacturing |
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| US10343331B2 (en) | 2015-12-22 | 2019-07-09 | Carbon, Inc. | Wash liquids for use in additive manufacturing with dual cure resins |
| JP6944935B2 (ja) | 2015-12-22 | 2021-10-06 | カーボン，インコーポレイテッド | 二重硬化樹脂を用いた積層造形による複数の中間体からの複合生産物の製作 |
| US10647054B2 (en) | 2015-12-22 | 2020-05-12 | Carbon, Inc. | Accelerants for additive manufacturing with dual cure resins |
| US10500786B2 (en) | 2016-06-22 | 2019-12-10 | Carbon, Inc. | Dual cure resins containing microwave absorbing materials and methods of using the same |
| EP3526301B1 (en) | 2016-10-14 | 2021-06-16 | Basf Se | Hardenable polymer composition |
| WO2018094131A1 (en) * | 2016-11-21 | 2018-05-24 | Carbon, Inc. | Method of making three-dimensional object by delivering reactive component for subsequent cure |
| CA3044541A1 (en) | 2016-12-05 | 2018-06-14 | Arkema Inc. | Initiator blends and photocurable compositions containing such initiator blends useful for 3d printing |
| WO2018165090A1 (en) | 2017-03-09 | 2018-09-13 | Carbon, Inc. | Tough, high temperature polymers produced by stereolithography |
| US10367228B2 (en) * | 2017-04-07 | 2019-07-30 | Seeo, Inc. | Diester-based polymer electrolytes for high voltage lithium ion batteries |
| US10316213B1 (en) | 2017-05-01 | 2019-06-11 | Formlabs, Inc. | Dual-cure resins and related methods |
| WO2018237038A1 (en) | 2017-06-21 | 2018-12-27 | Carbon, Inc. | Method of additive manufacturing |
| AU2018373053C1 (en) | 2017-11-24 | 2021-04-01 | Lunella Biotech, Inc. | Triphenylphosphonium-derivative compounds for eradicating cancer stem cells |
| US11135649B2 (en) | 2018-02-27 | 2021-10-05 | Arizona Board Of Regents On Behalf Of Arizona State University | Direct metal printing with stereolithography |
| US11504903B2 (en) | 2018-08-28 | 2022-11-22 | Carbon, Inc. | 1K alcohol dual cure resins for additive manufacturing |
| EP3848179A1 (de) | 2020-01-10 | 2021-07-14 | Carl Zeiss Vision International GmbH | Inkjet-verfahren zur herstellung eines brillenglases |
| US20220011670A1 (en) * | 2020-07-08 | 2022-01-13 | International Business Machines Corporation | Resist underlayer surface modification |
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| CN117466862B (zh) * | 2022-07-20 | 2025-10-21 | 天津久日新材料股份有限公司 | 一种含硫光引发剂及其制备方法和应用 |
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| EP0448154A1 (en) | 1990-03-20 | 1991-09-25 | Akzo Nobel N.V. | Coating composition including a blocked basic catalyst |
| EP0702707A1 (en) | 1993-05-26 | 1996-03-27 | Akzo Nobel N.V. | Coating composition including a uv-deblockable basic catalyst |
| US6362301B1 (en) | 1994-06-13 | 2002-03-26 | Rohm And Haas Company | Curable composition |
| US5998496A (en) | 1995-10-31 | 1999-12-07 | Spectra Group Limited, Inc. | Photosensitive intramolecular electron transfer compounds |
| BR9707687A (pt) | 1996-02-22 | 1999-07-27 | Dsm Nv | Fotocatalisador aniônico |
| EP0971924B1 (en) | 1997-01-22 | 2002-08-21 | Ciba SC Holding AG | Photoactivatable nitrogen-containing bases based on alpha-amino ketones |
| BR9807790B1 (pt) | 1997-02-26 | 2010-05-18 | bases fotoativadas contendo nitrogênio baseadas em alfa-amÈnio cetonas, imìnio cetonas ou amidìnio cetonas e aril boratos, composição que as contém e processo para execução de reações catalisadas por base. | |
| KR100527614B1 (ko) * | 1997-03-18 | 2005-11-15 | 시바 스페셜티 케미칼스 홀딩 인크. | α-아미노 알켄 화합물, 이의 제조방법 및 당해 화합물을 포함하는 조성물 |
| EP0898202B1 (en) | 1997-08-22 | 2000-07-19 | Ciba SC Holding AG | Photogeneration of amines from alpha-aminoacetophenones |
| EP1105368B1 (de) | 1998-08-21 | 2002-10-30 | Ciba SC Holding AG | Photoaktivierbare stickstoffhaltige basen |
| JP4906221B2 (ja) | 2000-05-26 | 2012-03-28 | アクゾ ノーベル ナムローゼ フェンノートシャップ | 光活性化可能なコーティング組成物 |
| CA2459374C (en) * | 2001-10-17 | 2011-02-08 | Ciba Specialty Chemicals Holding Inc. | Photoactivable nitrogen bases |
| PL207529B1 (pl) * | 2002-04-19 | 2010-12-31 | Ciba Sc Holding Ag | Sposób wytwarzania powlekanego podłoża |
| EP1789188A2 (en) | 2004-07-21 | 2007-05-30 | CIBA SPECIALTY CHEMICALS HOLDING INC. Patent Departement | Process for the photoactivation and use of a catalyst by an inverted two-stage procedure |
| CN101490155A (zh) | 2006-07-17 | 2009-07-22 | 西巴控股有限公司 | 粘结方法 |
| BRPI0717655B1 (pt) | 2006-09-29 | 2018-12-18 | Basf Se | bases fotolatentes para sistema à base de isocianatos bloqueados |
| ATE524765T1 (de) | 2007-04-03 | 2011-09-15 | Basf Se | Fotoaktivierbare stickstoffbasen |
-
2008
- 2008-03-25 AT AT08718153T patent/ATE524765T1/de not_active IP Right Cessation
- 2008-03-25 KR KR1020147033474A patent/KR101944734B1/ko not_active Expired - Fee Related
- 2008-03-25 KR KR1020097022890A patent/KR101514093B1/ko not_active Expired - Fee Related
- 2008-03-25 JP JP2010501474A patent/JP5606308B2/ja not_active Expired - Fee Related
- 2008-03-25 CN CN200880009820XA patent/CN101641643B/zh not_active Expired - Fee Related
- 2008-03-25 MX MX2009010309A patent/MX2009010309A/es active IP Right Grant
- 2008-03-25 US US12/532,840 patent/US9921477B2/en active Active
- 2008-03-25 WO PCT/EP2008/053456 patent/WO2008119688A1/en not_active Ceased
- 2008-03-25 EP EP08718153A patent/EP2145231B1/en not_active Not-in-force
- 2008-03-25 CA CA2681201A patent/CA2681201C/en not_active Expired - Fee Related
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2018
- 2018-01-26 US US15/880,695 patent/US10928728B2/en not_active Expired - Fee Related
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2020
- 2020-10-09 US US17/066,750 patent/US20210033972A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20180217498A1 (en) | 2018-08-02 |
| US10928728B2 (en) | 2021-02-23 |
| US20210033972A1 (en) | 2021-02-04 |
| KR101944734B1 (ko) | 2019-02-07 |
| MX2009010309A (es) | 2009-10-16 |
| US9921477B2 (en) | 2018-03-20 |
| ATE524765T1 (de) | 2011-09-15 |
| CN101641643B (zh) | 2013-08-07 |
| KR101514093B1 (ko) | 2015-04-21 |
| US20100105794A1 (en) | 2010-04-29 |
| KR20150005683A (ko) | 2015-01-14 |
| WO2008119688A1 (en) | 2008-10-09 |
| CA2681201A1 (en) | 2008-10-09 |
| EP2145231B1 (en) | 2011-09-14 |
| CN101641643A (zh) | 2010-02-03 |
| EP2145231A1 (en) | 2010-01-20 |
| KR20100016136A (ko) | 2010-02-12 |
| JP5606308B2 (ja) | 2014-10-15 |
| JP2010523515A (ja) | 2010-07-15 |
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