WO2001002464A1 - Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates - Google Patents
Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates Download PDFInfo
- Publication number
- WO2001002464A1 WO2001002464A1 PCT/EP2000/006203 EP0006203W WO0102464A1 WO 2001002464 A1 WO2001002464 A1 WO 2001002464A1 EP 0006203 W EP0006203 W EP 0006203W WO 0102464 A1 WO0102464 A1 WO 0102464A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- polycyanate
- alkyl
- monocyanate
- polycyanate copolymer
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 38
- 150000001913 cyanates Chemical class 0.000 title abstract description 11
- 230000003287 optical effect Effects 0.000 claims abstract description 34
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 229920005989 resin Polymers 0.000 claims abstract description 12
- 239000011347 resin Substances 0.000 claims abstract description 12
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 11
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 238000005253 cladding Methods 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000000872 buffer Substances 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000013307 optical fiber Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 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 8
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000620 organic polymer Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- -1 polyarylsulfones Polymers 0.000 description 5
- 239000004644 polycyanurate Substances 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- 229920006037 cross link polymer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 0 C**(*(C1CC(C)C1)C(*)(C1)CC2C)C1(*C(C1)(CC(*)(CC3*)*(C4)CCCC5)*4*5C1(*)C(*)C3OC#C)CC(*)C(*)C2OC#N Chemical compound C**(*(C1CC(C)C1)C(*)(C1)CC2C)C1(*C(C1)(CC(*)(CC3*)*(C4)CCCC5)*4*5C1(*)C(*)C3OC#C)CC(*)C(*)C2OC#N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000003486 chemical etching Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001029 thermal curing Methods 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- BRWSGXBWHTWKRJ-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) cyanate Chemical compound FC1=C(F)C(F)=C(OC#N)C(F)=C1F BRWSGXBWHTWKRJ-UHFFFAOYSA-N 0.000 description 1
- JDIPZHAYUYYGSN-UHFFFAOYSA-N (4-propylphenyl) cyanate Chemical compound CCCC1=CC=C(OC#N)C=C1 JDIPZHAYUYYGSN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- WFKPHGVHNRTDGT-UHFFFAOYSA-N [4-(1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl] cyanate Chemical compound FC(F)(F)C(C(F)(F)F)C1=CC=C(OC#N)C=C1 WFKPHGVHNRTDGT-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 description 1
- 229920006260 polyaryletherketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT00952993T ATE259846T1 (en) | 1999-07-01 | 2000-07-03 | WAVEGUIDE COMPONENTS OR STRUCTURES OR PARTS THEREOF CONTAINING POLYCYANATE COPOLYMERS FROM POLYFUNCTIONAL CYANATES AND FLUORINATED MONOCYANATES |
EP20000952993 EP1198493B1 (en) | 1999-07-01 | 2000-07-03 | Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates |
US10/019,447 US6716958B1 (en) | 1999-07-01 | 2000-07-03 | Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates |
DE60008384T DE60008384T2 (en) | 1999-07-01 | 2000-07-03 | WAVE GUIDE COMPONENTS OR STRUCTURES OR PARTS CONTAINING THEM POLYCYANATE COPOLYMERS MADE OF POLYFUNCTIONAL CYANATES AND FLUORINE MONOCYANATES |
AU65605/00A AU6560500A (en) | 1999-07-01 | 2000-07-03 | Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates |
CA002377745A CA2377745A1 (en) | 1999-07-01 | 2000-07-03 | Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99112596.4 | 1999-07-01 | ||
EP99112596A EP1067149A1 (en) | 1999-07-01 | 1999-07-01 | Polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001002464A1 true WO2001002464A1 (en) | 2001-01-11 |
Family
ID=8238479
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/006203 WO2001002464A1 (en) | 1999-07-01 | 2000-07-03 | Waveguide systems or structures or parts thereof, containing polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates |
PCT/EP2000/006206 WO2001002465A1 (en) | 1999-07-01 | 2000-07-03 | Polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates, and optical elements prepared therefrom |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/006206 WO2001002465A1 (en) | 1999-07-01 | 2000-07-03 | Polycyanate copolymers prepared from polyfunctional cyanates and fluorinated monocyanates, and optical elements prepared therefrom |
Country Status (7)
Country | Link |
---|---|
US (1) | US6716958B1 (en) |
EP (3) | EP1067149A1 (en) |
AT (1) | ATE259846T1 (en) |
AU (2) | AU6560500A (en) |
CA (1) | CA2377745A1 (en) |
DE (1) | DE60008384T2 (en) |
WO (2) | WO2001002464A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112014924A (en) * | 2020-09-07 | 2020-12-01 | 科竟达生物科技有限公司 | Method for decorating nanocubes on surface of polymer optical waveguide, optical waveguide manufactured by method, biosensing system and application |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1726607A3 (en) * | 2005-05-25 | 2009-08-05 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Triazine containing polymers |
CN102199289B (en) * | 2011-04-08 | 2013-01-02 | 扬州天启化学股份有限公司 | Method for preparing tetramethyl bisphenol F type cyanate resin prepolymer |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0581268A1 (en) * | 1992-07-29 | 1994-02-02 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Flame-retarded thermosetting resin composition, prepregs and electrical laminates made therefrom |
US5780159A (en) * | 1994-10-08 | 1998-07-14 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Plastic optical components |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5089660A (en) * | 1988-01-22 | 1992-02-18 | The Dow Chemical Company | Aromatic polycyanate/monocyanate comonomer compositions and polytriazines derived therefrom |
US5165959A (en) | 1990-05-18 | 1992-11-24 | At&T Bell Laboratories | Method of making triazine optical waveguides |
US5208892A (en) | 1990-05-18 | 1993-05-04 | At&T Bell Laboratories | Triazine optical waveguides |
EP0604823A1 (en) * | 1992-12-29 | 1994-07-06 | International Business Machines Corporation | Triazine polymer and use thereof |
-
1999
- 1999-07-01 EP EP99112596A patent/EP1067149A1/en not_active Withdrawn
-
2000
- 2000-07-03 EP EP20000952993 patent/EP1198493B1/en not_active Expired - Lifetime
- 2000-07-03 WO PCT/EP2000/006203 patent/WO2001002464A1/en active Search and Examination
- 2000-07-03 DE DE60008384T patent/DE60008384T2/en not_active Expired - Lifetime
- 2000-07-03 US US10/019,447 patent/US6716958B1/en not_active Expired - Lifetime
- 2000-07-03 CA CA002377745A patent/CA2377745A1/en not_active Abandoned
- 2000-07-03 AU AU65605/00A patent/AU6560500A/en not_active Abandoned
- 2000-07-03 WO PCT/EP2000/006206 patent/WO2001002465A1/en not_active Application Discontinuation
- 2000-07-03 AU AU62676/00A patent/AU6267600A/en not_active Abandoned
- 2000-07-03 EP EP00949246A patent/EP1196477A1/en not_active Withdrawn
- 2000-07-03 AT AT00952993T patent/ATE259846T1/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0581268A1 (en) * | 1992-07-29 | 1994-02-02 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Flame-retarded thermosetting resin composition, prepregs and electrical laminates made therefrom |
US5780159A (en) * | 1994-10-08 | 1998-07-14 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Plastic optical components |
Non-Patent Citations (1)
Title |
---|
SNOW A W ET AL: "FLUOROMETHYLENE CYANATE ESTER RESINS. SYNTHESIS, CHARACTERIZATION, AND FLUOROMETHYLENE CHAIN LENGTH EFFECTS", MACROMOLECULES, vol. 30, no. 3, 10 February 1997 (1997-02-10), pages 394 - 405, XP000678009, ISSN: 0024-9297 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112014924A (en) * | 2020-09-07 | 2020-12-01 | 科竟达生物科技有限公司 | Method for decorating nanocubes on surface of polymer optical waveguide, optical waveguide manufactured by method, biosensing system and application |
CN112014924B (en) * | 2020-09-07 | 2021-09-28 | 科竟达生物科技有限公司 | Method for decorating nanocubes on surface of polymer optical waveguide, optical waveguide manufactured by method, biosensing system and application |
Also Published As
Publication number | Publication date |
---|---|
AU6560500A (en) | 2001-01-22 |
EP1198493A1 (en) | 2002-04-24 |
DE60008384D1 (en) | 2004-03-25 |
AU6267600A (en) | 2001-01-22 |
DE60008384T2 (en) | 2004-12-02 |
EP1196477A1 (en) | 2002-04-17 |
EP1198493B1 (en) | 2004-02-18 |
WO2001002465A1 (en) | 2001-01-11 |
ATE259846T1 (en) | 2004-03-15 |
EP1067149A1 (en) | 2001-01-10 |
US6716958B1 (en) | 2004-04-06 |
CA2377745A1 (en) | 2001-01-11 |
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