DK2588549T3 - D1479-stabil flydende bap-fotoinitiator og dens anvendelse i strålingshærdende sammensætninger - Google Patents
D1479-stabil flydende bap-fotoinitiator og dens anvendelse i strålingshærdende sammensætninger Download PDFInfo
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- DK2588549T3 DK2588549T3 DK11728156.8T DK11728156T DK2588549T3 DK 2588549 T3 DK2588549 T3 DK 2588549T3 DK 11728156 T DK11728156 T DK 11728156T DK 2588549 T3 DK2588549 T3 DK 2588549T3
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- liquid
- acyl
- phosphine
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- 239000007788 liquid Substances 0.000 title claims description 243
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 257
- 239000000203 mixture Substances 0.000 claims description 166
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 128
- 230000005855 radiation Effects 0.000 claims description 104
- 238000000576 coating method Methods 0.000 claims description 103
- 239000007787 solid Substances 0.000 claims description 99
- -1 ethylphenyl group Chemical group 0.000 claims description 97
- 239000008199 coating composition Substances 0.000 claims description 78
- 239000011248 coating agent Substances 0.000 claims description 64
- 125000002252 acyl group Chemical group 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 239000013307 optical fiber Substances 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 42
- 239000002184 metal Substances 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 239000004567 concrete Substances 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 18
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 17
- 229910052753 mercury Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- VVBXKASDRZXWON-UHFFFAOYSA-N N=[PH3] Chemical compound N=[PH3] VVBXKASDRZXWON-UHFFFAOYSA-N 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- KGQCLZJFUIPDGS-UHFFFAOYSA-N dioxaphospholane Chemical compound C1CPOO1 KGQCLZJFUIPDGS-UHFFFAOYSA-N 0.000 claims description 9
- 238000004806 packaging method and process Methods 0.000 claims description 9
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 238000003860 storage Methods 0.000 claims description 9
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 claims description 9
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002841 Lewis acid Substances 0.000 claims description 8
- IBQKNIQGYSISEM-UHFFFAOYSA-N [Se]=[PH3] Chemical compound [Se]=[PH3] IBQKNIQGYSISEM-UHFFFAOYSA-N 0.000 claims description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 8
- 239000012965 benzophenone Substances 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 239000011651 chromium Substances 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- 229920002677 supramolecular polymer Polymers 0.000 claims description 7
- SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052788 barium Inorganic materials 0.000 claims description 6
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 6
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052793 cadmium Inorganic materials 0.000 claims description 6
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 6
- 239000010931 gold Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 230000035699 permeability Effects 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 5
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 4
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 230000005496 eutectics Effects 0.000 claims description 4
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 4
- 238000005057 refrigeration Methods 0.000 claims description 4
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- ZANRHLGMHYOWQU-UHFFFAOYSA-N 1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)C(=O)C(C)CC1=CC=C(OCCO)C=C1 ZANRHLGMHYOWQU-UHFFFAOYSA-N 0.000 claims description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 3
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 claims description 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052776 Thorium Inorganic materials 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical group CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052790 beryllium Inorganic materials 0.000 claims description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
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- 229910052763 palladium Inorganic materials 0.000 claims description 3
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 claims description 3
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 claims description 3
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- 239000004332 silver Substances 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 3
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 claims description 3
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- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 claims description 2
- IFBMOBFQBJZBMV-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphanyl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C IFBMOBFQBJZBMV-UHFFFAOYSA-N 0.000 claims description 2
- 238000003847 radiation curing Methods 0.000 claims 7
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- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- SYJCUYXTMQSJLM-UHFFFAOYSA-N phenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)PC1=CC=CC=C1 SYJCUYXTMQSJLM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- G—PHYSICS
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- C03C25/1055—
-
- 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
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/104—Coating to obtain optical fibres
- C03C25/106—Single coatings
-
- 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
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/25—Non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/48—Macromolecular compounds
- C04B41/483—Polyacrylates
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/60—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only artificial stone
- C04B41/61—Coating or impregnation
- C04B41/62—Coating or impregnation with organic materials
- C04B41/63—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F9/50—Organo-phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F9/50—Organo-phosphines
- C07F9/5036—Phosphines containing the structure -C(=X)-P or NC-P
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
- C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
-
- 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
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Claims (12)
1. Strålingshærdende sammensætning valgt fra gruppen bestående af en belægningssammensætning til optiske fibre (hvilken belægningssammensætning fortrinsvis er valgt fra gruppen bestående af en primær belægning, en sekundær belægning, og farvebelægning, og upjacketing-belægning, en bufferbelægning og en matrixbelægning), en belægningssammensætning, som kan strålingshærde på beton, og en belægningssammensætning, som kan strålingshærde på metal, hvilken sammensætning omfatter en flydende /vv(acyl)phosphin med formlen (I):
(I) , og mindst én bestanddel, som kan polymeriseres ved hjælp af frie radikaler; hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe.
2. Strålingshærdende sammensætning ifølge krav 1, som endvidere omfatter et fe(acyl)phosphinoxid med formlen (II), som er flydende ved 20°C:
(II) , hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe.
3. Strålingshærdende sammensætning ifølge krav 1 eller 2, hvor hver af Ar1, Ar2 og Ar3 er uafhængigt valgt fra gruppen bestående af en phenylgruppe, en methylphenylgruppe, en ethylphenylgruppe, en dimethylphenylgruppe, en trialkylphenylgruppe, en isopropylphenylgruppe, en fert-butylphenylgruppe, en methoxyphenylgruppe, en dimethoxyphenylgruppe, en ethoxyphenylgruppe, en diethoxyphenylgruppe, en isopropoxyphenylgruppe, en thiomethoxyphenylgruppe, en naphthylgruppe, en thiophenylgruppe og en pyridylgruppe, hvor phosphinoxidet fortrinsvis er bis(2,4,6-1rimethylbenzoyl)pheny 1 phosphinoxid, hvor Ar1 er en phenylgruppe, og hvor hver af Ar2 og Ar3 er en 2,4,6-trimethylphenylgruppe.
4. Strålingshærdende sammensætning valgt fra gruppen bestående af en belægningssammensætning til optiske fibre og en belægningssammensætning, som kan strålingshærde på beton, og en belægningssammensætning, som kan strålingshærde på metal, hvilken sammensætning omfatter mindst én bestanddel, som kan polymeriseres ved hjælp af frie radikaler, og en kombination af mindst to fotoinitiatorer, hvor mindst én fotoinitiator er flydende bis(2,4,6-trimethylbenzoyl)phenylphosphin, og mindst én fotoinitiator er bis(2,4,6-trimethylbenzoyl)phenylphosphinoxid, hvor kombinationen af /v,v(acyl)phosphin og /vv(acyl)phosphinoxid fortrinsvis er flydende ved en temperatur på ca. 15°C eller derover, og hvor 6A(2,4,6-trimethylbcnzoyl)phenylphosphinct, som er flydende ved 20°C, og bis(2,4,6-trimethylbenzoyljphenylphosphinoxidet fortrinsvis forefindes i et forhold på ca. 1:1 som målt ved HPLC.
5. Strålingshærdende sammensætning ifølge et hvilket som helst af kravene 1-4, hvor sammensætningen kan hærdes ved hjælp af UV-lys genereret af en konventionel UV-lyskilde og/eller ved hjælp aflys genereret af en LED-lyskilde. 6. 5A(acyl)phosphin med formlen (I), som er flydende ved 20°C:
(I), hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe; og hvor tø(acyl)phosphinen er stabiliseret med mindst én teknik valgt fra gruppen bestående af emballage med lav oxygenpermeabilitet, køling under forsendelse og opbevaring og indhylning i inert gas. 7. 5A(acyl)phosphin med formlen (I), som er flydende ved 20°C:
(I), hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe; og hvor &A(acyl)phosphincn er stabiliseret som en blanding med en eller flere forbindelser valgt fra gruppen bestående af en flydende fotoinitiator, en fast fotoinitiator, et flydende eller fast phosphit, en flydende eller fast thiophosphinsyre, et flydende eller fast phosphinsulfid, et flydende eller fast phosphinselenid, et flydende eller fast phosphintellurid, et flydende eller fast phosphinhalogenid, et flydende eller fast iminophosphoran og et flydende eller fast dioxaphospholan, hvor blandingen fortrinsvis omfatter mindst én flydende fotoinitiator valgt fra gruppen bestående af 2,4,6-(trimethylbenzoylethoxy,phenylphosphin)oxid, diethoxyacetophenon, 2-hydroxy-2-methyl-l-phenyl-propan-l-on, methylphenylglyoxylat og acryleret benzophenon, hvor den stabiliserede flydende Å/s(acyl)phosphin fortrinsvis omfatter 25 til 75 vægtprocent /vs(acyl)phosphin.
8. Stabiliseret flydende Å/s(acyl)phosphin ifølge krav 7, hvor tø(acyl)phosphinen er stabiliseret som en blanding med mindst én fast fotoinitiator valgt fra gruppen bestående af 4-methylbenzophenon, p-phenylbenzophenon, 4,4'-/v,s(dimcthylamino)benzophenon, 4-benzoyl-4'-methyldiphenylsulfid, 4,4'-(tetraethyldiamino)benzophenon, 4,4’-(tetraethyldiamino)benzophenon, benzophenon, 2-hydroxy-l-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propan-l-on, 1-hydroxycyclohexylphenylketon, 2,2-dimethoxy-2-phenylacetophenon, 4-(2-hydroxyethoxy)phenyl-(2-propyl)keton, kamferquinon og 2,4,6-trimethylbenzophenon, hvor den stabiliserede flydende /v.s(acyl)phosphin fortrinsvis omfatter 25 til 75 vægtprocent éii(acyl)phosphin, og/eller hvor blandingen fortrinsvis er en eutektisk blanding.
9. Stabiliseret flydende /v.v(acyl)phosphin ifølge krav 7, hvor (i) blandingen omfatter mindst ét flydende eller fast phosphit med formlen (III):
(III), hvor hver af R1, R2 og R3 er uafhængigt valgt fra gruppen bestående af en (C1-C12)-alkylgruppe og en phenylgruppe, og hvor phenylgruppen er en substitueret eller usubstitueret phenylgruppe, hvor hver af R1, R2 og R3 fortrinsvis uafhængigt er en alkylphenylgruppe, og/eller hvor det flydende eller faste phosphit fortrinsvis er valgt fra gruppen bestående af ira(no ny 1 p hc ny 1) pho sp h it, tributylphosphit eller blandinger deraf, og/eller hvor blandingen fortrinsvis er en ca. 1:1 blanding eller mindre med hensyn til phosphit; (ii) blandingen omfatter mindst én flydende eller fast thiophosphinsyre med formlen (IV):
(IV) , hvor hver af R4 og R5 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, hvor hver af R4 og R5 eventuelt er substitueret; (iii) blandingen omfatter mindst ét flydende eller fast phosphinsulfid med formlen (V):
(V) , hvor hver af R6, R7 og R8 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, hvor hver af R6, R7 og R8 eventuelt er substitueret; (iv) blandingen omfatter mindst ét flydende eller fast phosphinselenid med formlen (VI):
(VI) , hvor hver af R6, R7 og R8 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, hvor hver af R6, R7 og R8 eventuelt er substitueret; (v) blandingen omfatter mindst ét flydende eller fast phosphintellurid med formlen (VII):
(VII) , hvor hver af R6, R7 og R8 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, hvor hver af R6, R7 og R8 eventuelt er substitueret; (vi) blandingen omfatter mindst ét flydende eller fast phosphinhalogenid med formlen (VIII):
(VIII) , hvor hver af R9, R10 og R11 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, hvor hver af X1 og X2 uafhængigt er et halogen, og hvor hver af R9, R10 og R11 eventuelt er substitueret; (vii) blandingen omfatter mindst ét flydende eller fast iminophosphoran med formlen (IX):
(IX) , hvor hver af R12, R13 og R14 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, hvor Ar4 er en arylgruppe, og hvor hver af R12, R13 og R14 og Ar4 eventuelt er substitueret; eller (viii) blandingen omfatter mindst ét flydende eller fast dioxaphospholan med formlen (X):
(X) , hvor hver af R15, R16, R17, R18, R19, R20 og R21 er uafhængigt valgt fra gruppen bestående af en alkylgruppe, en arylgruppe, en acylgruppe og en heteroarylgruppe, og hvor hver af R15, R16, R17, R18, R19, R20 og R21 eventuelt er substitueret. 10. 5A(acyl)phosphin med formlen (I), som er flydende ved 20°C:
(I), hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe; og hvor 6A(acyl)phosphinen er stabiliseret som et reaktionsprodukt med en forbindelse valgt fra gruppen bestående af et metal, dodecylravsyreanhydrid, en ureaforbindelse, en Lewis-syre (fortrinsvis valgt fra gruppen bestående af supramolekylære polymerer, imidazolderivater og guanidinderivater) og en catecholforbindelse.
11. Stabiliseret flydende /vv(acyl)phosphin ifølge krav 10, hvor metallet er et overgangsmetal, eller hvor metallet er valgt fra gruppen bestående af vanadium (V), jern (Fe), indium (In), thorium (Th), kviksølv (Hg), kobber (Cu), nikkel (Ni), yttrium (Y), bly (Pb), zink (Zn), cadmium (Cd), cobalt (Co), mangan (Mn), calcium (Ca), magnesium (Mg), strontium (Sr), barium (Ba), zirkonium (Zr), titan (Ti), chrom (Cr), rubidium (Rb), molybden (Mo), ruthenium (Ru), palladium (Pd), sølv (Ag), cadmium (Cd), tin (Sn), antimon (Sb), barium (Ba), wolfram (W), platin (Pt), guld (Au), bismuth (Bi) og beryllium (Be), hvor den stabiliserede flydende 6A(acyl)phosphin fortrinsvis har formlen (XI) eller formlen (XII):
(XI) , (XII) , hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe, og hvor M er et metal.
12. Stabiliseret flydende /vv(acyl)phosphin ifølge krav 10, som har formlen (XIII) eller formlen (XIV): (Χΐιΐ),
(XIV), hvor hver af Ar1, Ar2 og Ar3 uafhængigt er en substitueret eller usubstitueret arylgruppe; og hvor hver af Ra, Rb og Rc er uafhængigt valgt fra gruppen bestående af hydrogen, en alkylgruppe og en substitueret alkylgruppe, hvor alkylgruppen og den substituerede alkylgruppe eventuelt er substitueret.
13. Stabiliseret flydende /v',v(acyl)phosphin ifølge et hvilket som helst af kravene 6-12, hvor hver af Ar1, Ar2 og Ar3 er uafhængigt valgt fra gruppen bestående af en phenylgruppe, en methylphenylgruppe, en ethylphenylgruppe, en dimethylphenylgruppe, en trialkylphenylgruppe, en isopropylphenylgruppe, en feri-butylphenylgruppe, en methoxyphenylgruppe, en dimethoxyphenylgruppe, en ethoxyphenylgruppe, en diethoxyphenylgruppe, en isopropoxyphenylgruppe, en thiomethoxyphenylgruppe, en naphthylgruppe, en thiophenylgruppe og en pyridylgruppe, hvor den stabiliserede phosphin fortrinsvis er stabiliseret flydende bis(2,4,6-trimethylbenzoyl)phenylphosphin, hvor Ar1 er en phenylgruppe, og hver af Ar2 og Ar3 er en 2,4,6-trimethylphenylgruppe.
14. Strålingshærdende sammensætning, som fortrinsvis er valgt fra gruppen bestående af en belægningssammensætning til optiske fibre (hvilken belægningssammensætning fortrinsvis er valgt fra gruppen bestående af en primær belægning, en sekundær belægning, en farvebelægning, en upjacketing-belægning, en bufferbelægning og en matrixbelægning), en belægningssammensætning, som kan strålingshærde på beton, og en belægningssammensætning, som kan strålingshærde på metal, hvilken sammensætning omfatter den stabiliserede flydende Z?z',y(acyl)phosphm ifølge et hvilket som helst af kravene 6-13 og mindst én bestanddel, som kan polymeriseres ved hjælp af frie radikaler, hvor sammensætningen fortrinsvis er flydende ved 20°C.
15. Strålingshærdende sammensætning ifølge krav 14, hvor sammensætningen kan hærdes ved hjælp af UV-lys genereret af en konventionel UV-lyskilde og/eller ved hjælp af lys genereret af en LED-lyskilde.
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KR101555800B1 (ko) | 2015-09-24 |
CN102471633B (zh) | 2015-03-18 |
BR112012029161A2 (pt) | 2017-02-21 |
US9062083B2 (en) | 2015-06-23 |
WO2012003106A1 (en) | 2012-01-05 |
US9062082B2 (en) | 2015-06-23 |
RU2012148698A (ru) | 2014-08-10 |
US20120129969A1 (en) | 2012-05-24 |
KR20140129242A (ko) | 2014-11-06 |
BR112012029161B1 (pt) | 2019-09-24 |
KR101580424B1 (ko) | 2015-12-24 |
KR20140129243A (ko) | 2014-11-06 |
US20130237626A1 (en) | 2013-09-12 |
JP5843326B2 (ja) | 2016-01-13 |
JP2013534935A (ja) | 2013-09-09 |
CN104327116A (zh) | 2015-02-04 |
EP2588549A1 (en) | 2013-05-08 |
EP2588549B1 (en) | 2014-12-10 |
RU2600053C2 (ru) | 2016-10-20 |
CN102471633A (zh) | 2012-05-23 |
WO2012003106A8 (en) | 2012-08-02 |
KR20130020790A (ko) | 2013-02-28 |
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