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)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Ceramic Engineering (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)
- Plural Heterocyclic Compounds (AREA)
- Indole 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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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2681201A Expired - Fee Related CA2681201C (en) | 2007-04-03 | 2008-03-25 | Photoactivable nitrogen bases |
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| KR (2) | KR101514093B1 (e) |
| CN (1) | CN101641643B (e) |
| AT (1) | ATE524765T1 (e) |
| CA (1) | CA2681201C (e) |
| MX (1) | MX2009010309A (e) |
| WO (1) | WO2008119688A1 (e) |
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| RU2009115962A (ru) * | 2006-09-29 | 2010-11-10 | Циба Холдинг Инк. (Ch) | Фотолатентные основания для систем, основанных на блокированных изоцианатах |
| EP2145231B1 (en) | 2007-04-03 | 2011-09-14 | Basf Se | Photoactivable nitrogen bases |
| US9624171B2 (en) * | 2008-06-06 | 2017-04-18 | 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 |
| GB2491643A (en) | 2011-06-10 | 2012-12-12 | Lambson Ltd | Method of forming a polymeric material on a substrate |
| US9616460B2 (en) | 2011-12-02 | 2017-04-11 | Toyota Motor Engineering & Manufacturing North America, Inc. | Terminate-on-demand cationic polymerization method for forming a two-dimensional coating |
| 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 |
| WO2015157983A1 (en) * | 2014-04-18 | 2015-10-22 | Dow Global Technologies Llc | Anthraquinone compound used for color filter of lcd |
| CN114734628A (zh) | 2014-06-23 | 2022-07-12 | 卡本有限公司 | 由具有多重硬化机制的材料制备三维物体的方法 |
| WO2016126796A2 (en) | 2015-02-05 | 2016-08-11 | Carbon3D, Inc. | Method of additive manufacturing by intermittent exposure |
| WO2016140886A1 (en) | 2015-03-05 | 2016-09-09 | Carbon3D, Inc. | Fabrication of three dimensional objects with multiple operating modes |
| CA2984145A1 (en) | 2015-04-29 | 2016-11-03 | 3M Innovative Properties Company | Method of making a polymer network from a polythiol and a polyepoxide |
| CN108350145B (zh) | 2015-09-04 | 2021-06-22 | 卡本有限公司 | 用于增材制造的氰酸酯双重固化树脂 |
| US10975193B2 (en) | 2015-09-09 | 2021-04-13 | Carbon, Inc. | Epoxy dual cure resins for additive manufacturing |
| 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 |
| US10501572B2 (en) | 2015-12-22 | 2019-12-10 | Carbon, Inc. | Cyclic ester dual cure resins for additive manufacturing |
| US10343331B2 (en) | 2015-12-22 | 2019-07-09 | Carbon, Inc. | Wash liquids for use in additive manufacturing with dual cure resins |
| 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 |
| EP3394673A1 (en) | 2015-12-22 | 2018-10-31 | Carbon, Inc. | Fabrication of compound products from multiple intermediates by additive manufacturing with dual cure resins |
| US10647054B2 (en) | 2015-12-22 | 2020-05-12 | Carbon, Inc. | Accelerants for additive manufacturing with dual cure resins |
| CN115195104B (zh) | 2015-12-22 | 2023-12-05 | 卡本有限公司 | 用于用双重固化树脂的增材制造的双重前体树脂系统 |
| WO2017112751A1 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Blocked silicone dual cure resins for additive manufacturing |
| US10500786B2 (en) | 2016-06-22 | 2019-12-10 | Carbon, Inc. | Dual cure resins containing microwave absorbing materials and methods of using the same |
| KR102426999B1 (ko) | 2016-10-14 | 2022-08-01 | 바스프 에스이 | 경질화가능한 중합체 조성물 |
| CN110023056B (zh) * | 2016-11-21 | 2021-08-24 | 卡本有限公司 | 通过递送反应性组分用于后续固化来制造三维物体的方法 |
| EP3548969A1 (en) | 2016-12-05 | 2019-10-09 | Arkema, Inc. | Initiator blends and photocurable compositions containing such initiator blends useful for 3d printing |
| US11535686B2 (en) | 2017-03-09 | 2022-12-27 | 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 |
| EP3600843B1 (en) | 2017-06-21 | 2021-07-21 | Carbon, Inc. | Resin dispenser for additive manufacturing |
| RU2020120686A (ru) | 2017-11-24 | 2021-12-24 | Лунелла Байотек, Инк. | Соединения производных трифенилфосфония для эрадикации раковых стволовых клеток |
| 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 |
| DE102022110540A1 (de) | 2022-04-29 | 2023-11-02 | tooz technologies GmbH | Verfahren zur anpassung des brechungsindex |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0448154A1 (en) | 1990-03-20 | 1991-09-25 | Akzo Nobel N.V. | Coating composition including a blocked basic catalyst |
| WO1994028075A1 (en) | 1993-05-26 | 1994-12-08 | 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 |
| DE69703480T3 (de) | 1996-02-22 | 2006-07-06 | Ciba Speciality Chemicals Holding Inc. | Anionischer photokatalysator |
| DE69807322T2 (de) | 1997-01-22 | 2003-04-17 | Ciba Speciality Chemicals Holding Inc., Basel | Fotoaktivierbare stickstoffhaltige basen, die auf alpha-aminoketonen basieren |
| KR100542419B1 (ko) | 1997-02-26 | 2006-01-11 | 시바 스페셜티 케미칼스 홀딩 인크. | α-암모늄 케톤, 이미늄 케톤 또는 아미디늄 케톤 및 아릴 보레이트계의 광활성화 가능한 질소 함유 염기, 이의 제조방법 및 이를 포함하는 조성물 |
| WO1998041524A1 (en) | 1997-03-18 | 1998-09-24 | Ciba Specialty Chemicals Holding Inc. | PHOTOACTIVATABLE NITROGEN-CONTAINING BASES BASED ON α-AMINO ALKENES |
| EP0898202B1 (en) | 1997-08-22 | 2000-07-19 | Ciba SC Holding AG | Photogeneration of amines from alpha-aminoacetophenones |
| DE59903270D1 (de) | 1998-08-21 | 2002-12-05 | Ciba Sc Holding Ag | Photoaktivierbare stickstoffhaltige basen |
| DE60125929T2 (de) | 2000-05-26 | 2007-11-08 | Akzo Nobel Coatings International B.V. | Photoaktivierbare beschichtungszusammensetzung |
| EP1436297B1 (en) * | 2001-10-17 | 2007-04-25 | Ciba Specialty Chemicals Holding Inc. | Photoactivable nitrogen bases |
| AU2003227644B2 (en) * | 2002-04-19 | 2008-08-21 | Ciba Specialty Chemicals Holding Inc. | Curing of coatings induced by plasma |
| WO2006008251A2 (en) | 2004-07-21 | 2006-01-26 | Ciba Specialty Chemicals Holding Inc. | Process for the photoactivation and use of a catalyst by an inverted two-stage procedure |
| US20100236707A1 (en) | 2006-07-17 | 2010-09-23 | Katia Studer | Method of bonding |
| RU2009115962A (ru) | 2006-09-29 | 2010-11-10 | Циба Холдинг Инк. (Ch) | Фотолатентные основания для систем, основанных на блокированных изоцианатах |
| EP2145231B1 (en) | 2007-04-03 | 2011-09-14 | Basf Se | Photoactivable nitrogen bases |
-
2008
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- 2008-03-25 CN CN200880009820XA patent/CN101641643B/zh not_active Expired - Fee Related
- 2008-03-25 JP JP2010501474A patent/JP5606308B2/ja not_active Expired - Fee Related
- 2008-03-25 KR KR1020097022890A patent/KR101514093B1/ko not_active Expired - Fee Related
- 2008-03-25 MX MX2009010309A patent/MX2009010309A/es active IP Right Grant
- 2008-03-25 WO PCT/EP2008/053456 patent/WO2008119688A1/en not_active Ceased
- 2008-03-25 KR KR1020147033474A patent/KR101944734B1/ko not_active Expired - Fee Related
- 2008-03-25 US US12/532,840 patent/US9921477B2/en active Active
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- 2008-03-25 CA CA2681201A patent/CA2681201C/en not_active Expired - Fee Related
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2018
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- 2020-10-09 US US17/066,750 patent/US20210033972A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP5606308B2 (ja) | 2014-10-15 |
| CN101641643B (zh) | 2013-08-07 |
| KR20150005683A (ko) | 2015-01-14 |
| KR20100016136A (ko) | 2010-02-12 |
| KR101944734B1 (ko) | 2019-02-07 |
| EP2145231B1 (en) | 2011-09-14 |
| US20180217498A1 (en) | 2018-08-02 |
| ATE524765T1 (de) | 2011-09-15 |
| US20100105794A1 (en) | 2010-04-29 |
| US10928728B2 (en) | 2021-02-23 |
| EP2145231A1 (en) | 2010-01-20 |
| KR101514093B1 (ko) | 2015-04-21 |
| MX2009010309A (es) | 2009-10-16 |
| JP2010523515A (ja) | 2010-07-15 |
| US9921477B2 (en) | 2018-03-20 |
| WO2008119688A1 (en) | 2008-10-09 |
| CA2681201A1 (en) | 2008-10-09 |
| US20210033972A1 (en) | 2021-02-04 |
| CN101641643A (zh) | 2010-02-03 |
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| EEER | Examination request |
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| MKLA | Lapsed |
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