JP4965264B2 - フルオロケミカルモノイソシアネートを調製する方法 - Google Patents
フルオロケミカルモノイソシアネートを調製する方法 Download PDFInfo
- Publication number
- JP4965264B2 JP4965264B2 JP2006547104A JP2006547104A JP4965264B2 JP 4965264 B2 JP4965264 B2 JP 4965264B2 JP 2006547104 A JP2006547104 A JP 2006547104A JP 2006547104 A JP2006547104 A JP 2006547104A JP 4965264 B2 JP4965264 B2 JP 4965264B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- mdi
- heptane
- mefbse
- fluorochemical
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000002904 solvent Substances 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 6
- DJXNLVJQMJNEMN-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,2,3,3,3-heptafluoropropane Chemical compound COC(F)(F)C(F)(C(F)(F)F)C(F)(F)F DJXNLVJQMJNEMN-UHFFFAOYSA-N 0.000 claims description 4
- FNUBKINEQIEODM-UHFFFAOYSA-N 3,3,4,4,5,5,5-heptafluoropentanal Chemical compound FC(F)(F)C(F)(F)C(F)(F)CC=O FNUBKINEQIEODM-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 18
- 239000012975 dibutyltin dilaurate Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000000843 powder Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- DSRUAYIFDCHEEV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(2-hydroxyethyl)-n-methylbutane-1-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DSRUAYIFDCHEEV-UHFFFAOYSA-N 0.000 description 4
- ZDKQQLGFDAYLPC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(4-hydroxybutyl)-n-methylbutane-1-sulfonamide Chemical compound OCCCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZDKQQLGFDAYLPC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 231100000693 bioaccumulation Toxicity 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- GRJRKPMIRMSBNK-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol Chemical compound OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GRJRKPMIRMSBNK-UHFFFAOYSA-N 0.000 description 2
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- CWRORZJYSUFYHO-UHFFFAOYSA-N (3z)-3-diazobicyclo[2.2.2]octane Chemical compound C1CC2C(=[N+]=[N-])CC1CC2 CWRORZJYSUFYHO-UHFFFAOYSA-N 0.000 description 1
- 0 *c1ccc(Cc(cc2)ccc2N=C=O)cc1 Chemical compound *c1ccc(Cc(cc2)ccc2N=C=O)cc1 0.000 description 1
- XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- PYLDCZJUHYVOAF-UHFFFAOYSA-N 4-chlorobutyl acetate Chemical compound CC(=O)OCCCCCl PYLDCZJUHYVOAF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- -1 hydroxyalkyl acrylate Chemical compound 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/751,142 | 2003-12-31 | ||
| US10/751,142 US7081545B2 (en) | 2003-12-31 | 2003-12-31 | Process for preparing fluorochemical monoisocyanates |
| PCT/US2004/041743 WO2005065164A2 (en) | 2003-12-31 | 2004-12-14 | Process for preparing fluorochemical monoisocyanates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007517033A JP2007517033A (ja) | 2007-06-28 |
| JP2007517033A5 JP2007517033A5 (enExample) | 2008-02-07 |
| JP4965264B2 true JP4965264B2 (ja) | 2012-07-04 |
Family
ID=34701272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006547104A Expired - Fee Related JP4965264B2 (ja) | 2003-12-31 | 2004-12-14 | フルオロケミカルモノイソシアネートを調製する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7081545B2 (enExample) |
| EP (1) | EP1699755B1 (enExample) |
| JP (1) | JP4965264B2 (enExample) |
| KR (1) | KR20060107836A (enExample) |
| CN (1) | CN100471834C (enExample) |
| AT (1) | ATE525348T1 (enExample) |
| CA (1) | CA2552000A1 (enExample) |
| WO (1) | WO2005065164A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004012324T2 (de) * | 2003-12-31 | 2009-03-19 | 3M Innovative Properties Co., St. Paul | Wasser- und ölabweisende fluoracrylate |
| US7253241B2 (en) | 2004-12-28 | 2007-08-07 | 3M Innovative Properties Company | Fluorochemical containing low adhesion backsize |
| US20060142530A1 (en) * | 2004-12-28 | 2006-06-29 | Moore George G | Water- and oil-repellent fluorourethanes and fluoroureas |
| US7291688B2 (en) * | 2004-12-28 | 2007-11-06 | 3M Innovative Properties Company | Fluoroacrylate-mercaptofunctional copolymers |
| US7411020B2 (en) | 2004-12-28 | 2008-08-12 | 3M Innovative Properties Company | Water-based release coating containing fluorochemical |
| US7345123B2 (en) * | 2004-12-28 | 2008-03-18 | 3M Innovative Properties Company | Fluoroacrylate-multifunctional acrylate copolymer compositions |
| AU2006263574B2 (en) * | 2005-06-29 | 2012-01-12 | 3M Innovative Properties Company | Polyurethanes derived from oligomeric fluoroacrylates |
| US7279210B2 (en) * | 2005-09-07 | 2007-10-09 | 3M Innovative Properties Company | Curable compositions, methods of making and using the same, and articles therefrom |
| US7560166B2 (en) * | 2005-12-28 | 2009-07-14 | 3M Innovative Properties Company | Adhesive article, composite article, and methods of making the same |
| US7981988B2 (en) * | 2006-05-25 | 2011-07-19 | 3M Innovative Properties Company | Ultraviolet radiation-polymerizable compositions |
| US20080075951A1 (en) * | 2006-09-27 | 2008-03-27 | 3M Innovative Properties Company | Fluoroacrylates and hardcoat compositions including the same |
| US8530054B2 (en) * | 2006-09-27 | 2013-09-10 | 3M Innovative Properties Company | Solar control multilayer film |
| WO2008083272A1 (en) * | 2006-12-29 | 2008-07-10 | 3M Innovative Properties Company | Stain and fouling resistant polyurea and polyurethane coatings |
| WO2011005396A1 (en) | 2009-06-12 | 2011-01-13 | 3M Innovative Properties Company | Fluorinated aromatic bis(acyl)-containing compounds and polyesters prepared therefrom |
| CN102686561B (zh) | 2009-12-22 | 2014-03-05 | 3M创新有限公司 | 氟化的含亚芳基化合物、方法以及由其制得的聚合物 |
| CN104927024A (zh) * | 2014-03-20 | 2015-09-23 | 江南大学 | 一种氟改性光固化聚氨酯丙烯酸酯树脂的制备方法及其作为光固化涂层疏水填料的应用 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2803656A (en) * | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbonsulfonamidoalkanols and sulfates thereof |
| US3776805A (en) * | 1971-09-07 | 1973-12-04 | Minnesota Mining & Mfg | Solar control products |
| US4321404A (en) * | 1980-05-20 | 1982-03-23 | Minnesota Mining And Manufacturing Company | Compositions for providing abherent coatings |
| US4540497A (en) * | 1982-11-09 | 1985-09-10 | Minnesota Mining And Manufacturing Company | Fluoroaliphatic radical-containing, substituted guanidines and fibrous substrates treated therewith |
| US4668726A (en) * | 1984-03-30 | 1987-05-26 | Minnesota Mining And Manufacturing Company | Cationic and non-ionic fluorochemicals and fibrous substrates treated therewith |
| US4566981A (en) * | 1984-03-30 | 1986-01-28 | Minnesota Mining And Manufacturing Company | Fluorochemicals and fibrous substrates treated therewith: compositions of cationic and non-ionic fluorochemicals |
| DE3521762A1 (de) * | 1985-06-19 | 1987-01-02 | Bayer Ag | Ionisch modifizierte pur-streichpasten und ihre verwendung |
| FR2588555B1 (fr) * | 1985-10-16 | 1987-12-11 | Atochem | Monomeres acryliques fluores, polymeres en derivant et leur application au traitement hydrofuge et oleofuge de substrats divers |
| US5144056A (en) * | 1985-12-03 | 1992-09-01 | Atochem | Fluorinated acrylic monomers as hydrophobic and oleophobic agents |
| FR2590895B1 (fr) * | 1985-12-03 | 1988-01-15 | Atochem | Monomeres acryliques fluores, polymeres en derivant et leur application comme agents hydrophobes et oleophobes |
| CA2048232A1 (en) * | 1990-09-05 | 1992-03-06 | Jerry W. Williams | Energy curable pressure-sensitive compositions |
| JPH0689462A (ja) | 1992-09-07 | 1994-03-29 | Three Bond Co Ltd | 光ディスク |
| TW312700B (enExample) * | 1994-05-17 | 1997-08-11 | Sony Co Ltd | |
| US5446118A (en) * | 1994-08-11 | 1995-08-29 | W. L. Gore & Associates, Inc. | Fluorinated acrylic monomers containing urethane groups and their polymers |
| US6017603A (en) * | 1995-04-28 | 2000-01-25 | Nippon Kayaku Kabushiki Kaisha | Ultraviolet-curing adhesive composition and article |
| US5688884A (en) * | 1995-08-31 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| DE19541174C2 (de) * | 1995-11-04 | 1998-11-26 | Spraying Systems Deutschland G | Hochleistungsstrahldüse |
| JPH09291258A (ja) * | 1996-04-26 | 1997-11-11 | Lintec Corp | 粘着剤組成物およびこれを用いた粘着シート |
| JP3835857B2 (ja) | 1996-06-18 | 2006-10-18 | 日本化薬株式会社 | 光ディスク用接着剤組成物、硬化物、物品及び接着方法 |
| JPH1025453A (ja) | 1996-07-08 | 1998-01-27 | Nippon Kayaku Co Ltd | 陰極線管用接着剤及びその硬化物 |
| JP3911728B2 (ja) | 1996-08-07 | 2007-05-09 | 住友化学株式会社 | ディジタルビデオディスクの保護コート兼接着用樹脂組成物 |
| JPH10140090A (ja) | 1996-11-08 | 1998-05-26 | Daicel U C B Kk | 陰極線管用接着剤およびその硬化物 |
| CN1252136A (zh) | 1997-02-13 | 2000-05-03 | Dsm有限公司 | 可光固化的树脂组合物 |
| TW430672B (en) * | 1997-07-03 | 2001-04-21 | Sumitomo Chemical Co | A photo-curing resin composition for DVD |
| US5959775A (en) * | 1997-12-23 | 1999-09-28 | 3M Innovative Properties Company | Urethane/acrylate bead bond for retroreflective articles |
| US6180200B1 (en) * | 1998-06-01 | 2001-01-30 | Dsm N. V. | Cationic and hybrid radiation curable pressure sensitive adhesives for bonding of optical discs |
| DE60042561D1 (de) * | 1999-10-27 | 2009-08-27 | 3M Innovative Properties Co | Fluorochemische sulfonamide tenside |
| DE19962272A1 (de) * | 1999-12-23 | 2001-06-28 | Basf Ag | Isocyanatgruppen aufweisende Bausteine sowie ihre Verwendung zur Funktionalisierung oder Modifizierung von Verbindungen oder Oberflächen |
| EP1142912A1 (en) | 2000-04-05 | 2001-10-10 | Dsm N.V. | Radiation curable compositions |
| US6949297B2 (en) * | 2001-11-02 | 2005-09-27 | 3M Innovative Properties Company | Hybrid adhesives, articles, and methods |
| DE602004012324T2 (de) * | 2003-12-31 | 2009-03-19 | 3M Innovative Properties Co., St. Paul | Wasser- und ölabweisende fluoracrylate |
-
2003
- 2003-12-31 US US10/751,142 patent/US7081545B2/en not_active Expired - Fee Related
-
2004
- 2004-12-14 AT AT04813986T patent/ATE525348T1/de not_active IP Right Cessation
- 2004-12-14 CA CA002552000A patent/CA2552000A1/en not_active Abandoned
- 2004-12-14 JP JP2006547104A patent/JP4965264B2/ja not_active Expired - Fee Related
- 2004-12-14 EP EP04813986A patent/EP1699755B1/en not_active Expired - Lifetime
- 2004-12-14 KR KR1020067013191A patent/KR20060107836A/ko not_active Withdrawn
- 2004-12-14 CN CNB2004800396658A patent/CN100471834C/zh not_active Expired - Fee Related
- 2004-12-14 WO PCT/US2004/041743 patent/WO2005065164A2/en not_active Ceased
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2006
- 2006-07-12 US US11/457,037 patent/US7361782B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7081545B2 (en) | 2006-07-25 |
| ATE525348T1 (de) | 2011-10-15 |
| EP1699755A4 (en) | 2007-11-07 |
| JP2007517033A (ja) | 2007-06-28 |
| CA2552000A1 (en) | 2005-07-21 |
| WO2005065164A2 (en) | 2005-07-21 |
| WO2005065164A3 (en) | 2005-09-09 |
| KR20060107836A (ko) | 2006-10-16 |
| EP1699755B1 (en) | 2011-09-21 |
| EP1699755A2 (en) | 2006-09-13 |
| US7361782B2 (en) | 2008-04-22 |
| US20050143595A1 (en) | 2005-06-30 |
| US20060247460A1 (en) | 2006-11-02 |
| CN1902164A (zh) | 2007-01-24 |
| CN100471834C (zh) | 2009-03-25 |
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