CA1338200C - Method for preparing a microencapsulated compound of a platinum group metal - Google Patents
Method for preparing a microencapsulated compound of a platinum group metalInfo
- Publication number
- CA1338200C CA1338200C CA000571228A CA571228A CA1338200C CA 1338200 C CA1338200 C CA 1338200C CA 000571228 A CA000571228 A CA 000571228A CA 571228 A CA571228 A CA 571228A CA 1338200 C CA1338200 C CA 1338200C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- polymer
- platinum
- microencapsulated
- ethylenically unsaturated
- 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 8
- 239000002184 metal Substances 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 49
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 229920000620 organic polymer Polymers 0.000 claims abstract description 12
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 12
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 10
- 238000005406 washing Methods 0.000 claims abstract description 8
- 238000001556 precipitation Methods 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims description 37
- -1 platinum group metals Chemical class 0.000 claims description 36
- 125000005375 organosiloxane group Chemical group 0.000 claims description 32
- 239000002245 particle Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 17
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 9
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 238000000151 deposition Methods 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims 1
- 239000003094 microcapsule Substances 0.000 abstract description 41
- 239000008393 encapsulating agent Substances 0.000 abstract description 37
- 238000006116 polymerization reaction Methods 0.000 abstract description 9
- 238000011065 in-situ storage Methods 0.000 abstract description 5
- 230000000737 periodic effect Effects 0.000 abstract description 5
- 150000002739 metals Chemical class 0.000 abstract description 4
- 238000010420 art technique Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 97
- 150000003058 platinum compounds Chemical class 0.000 description 54
- 239000003054 catalyst Substances 0.000 description 43
- 229910052697 platinum Inorganic materials 0.000 description 26
- 239000000463 material Substances 0.000 description 25
- 239000004615 ingredient Substances 0.000 description 20
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 11
- 238000006459 hydrosilylation reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 238000005354 coacervation Methods 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920000867 polyelectrolyte Polymers 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241001028048 Nicola Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000010406 interfacial reaction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/20—After-treatment of capsule walls, e.g. hardening
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/901—Room temperature curable silicon-containing polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
- Y10T428/2987—Addition polymer from unsaturated monomers only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US075,790 | 1987-07-20 | ||
| US07/075,790 US4784879A (en) | 1987-07-20 | 1987-07-20 | Method for preparing a microencapsulated compound of a platinum group metal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1338200C true CA1338200C (en) | 1996-04-02 |
Family
ID=22128005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000571228A Expired - Fee Related CA1338200C (en) | 1987-07-20 | 1988-07-06 | Method for preparing a microencapsulated compound of a platinum group metal |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4784879A (enFirst) |
| EP (1) | EP0300644B1 (enFirst) |
| JP (1) | JPS6447442A (enFirst) |
| AU (1) | AU602102B2 (enFirst) |
| BR (1) | BR8803620A (enFirst) |
| CA (1) | CA1338200C (enFirst) |
| DE (1) | DE3852120T2 (enFirst) |
Families Citing this family (203)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4874667A (en) * | 1987-07-20 | 1989-10-17 | Dow Corning Corporation | Microencapsulated platinum-group metals and compounds thereof |
| JP2665941B2 (ja) * | 1988-06-29 | 1997-10-22 | 東レ・ダウコーニング・シリコーン株式会社 | ヒドロシリル化反応用白金系触媒含有粒状物 |
| JPH0214244A (ja) * | 1988-06-30 | 1990-01-18 | Toray Dow Corning Silicone Co Ltd | 加熱硬化性オルガノポリシロキサン組成物 |
| US5015691A (en) * | 1989-05-22 | 1991-05-14 | General Electric Company | One part heat curable organopolysiloxane compositions |
| JP2916179B2 (ja) * | 1989-11-17 | 1999-07-05 | 東レ・ダウコーニング・シリコーン株式会社 | 加熱硬化性オルガノポリシロキサン組成物 |
| DE4015753A1 (de) * | 1990-05-16 | 1991-11-21 | Basf Ag | Farbbildner enthaltende mikrokapseln |
| US5066699A (en) * | 1990-08-31 | 1991-11-19 | Dow Corning Corporation | Storage stable heat curable organosiloxane compositions containing a microencapsulated catalyst and method for preparing said catalyst |
| JP3137701B2 (ja) * | 1990-12-19 | 2001-02-26 | 三井化学株式会社 | 架橋ポリオレフィン成形物の製造方法 |
| US5194460A (en) * | 1992-01-02 | 1993-03-16 | Dow Corning Corporation | Storage stable heat curable organosiloxane compositions containing a microencapsulated catalyst and method for preparing said catalyst |
| US5254656A (en) * | 1992-08-31 | 1993-10-19 | Dow Corning Corporation | Curable organosiloxane compositions containing organotitanate/microencapsulated platinum co-catalysts |
| US5424374A (en) * | 1992-09-30 | 1995-06-13 | Shin-Etsu Chemical Co., Ltd. | Heat curable organopolysiloxane compositions |
| JP3024432B2 (ja) * | 1993-04-23 | 2000-03-21 | 信越化学工業株式会社 | シリコーンゴム組成物及びその硬化方法 |
| US5525425A (en) * | 1993-10-19 | 1996-06-11 | Shin-Etsu Chemical Co., Ltd. | Heat curable silicone elastomer compositions |
| JP3024473B2 (ja) * | 1993-12-07 | 2000-03-21 | 信越化学工業株式会社 | 熱可塑性フルオロシリコーン樹脂及びその製造方法 |
| JP3899134B2 (ja) * | 1993-12-29 | 2007-03-28 | 東レ・ダウコーニング株式会社 | 加熱硬化性シリコーン組成物 |
| US5527837A (en) * | 1994-04-25 | 1996-06-18 | Shin-Etsu Chemical Co., Ltd. | Heat-curable silicone elastomer compositions |
| JP3763484B2 (ja) * | 1995-08-31 | 2006-04-05 | 東レ・ダウコーニング株式会社 | ヒドロシリル化反応用微粒子触媒およびこれを含有してなる加熱硬化性シリコーン組成物 |
| US5863968A (en) * | 1996-04-19 | 1999-01-26 | Dow Corning Corporation | High tear strength high consistency organosiloxane compositions comprising fluorinated and non-fluorinated polyorganosiloxanes |
| US5665794A (en) * | 1996-05-20 | 1997-09-09 | Dow Corning Corporation | Method for controlling cure initiation and curing times of platinum group metal curing fluorosilicone compositions |
| US20050095492A1 (en) * | 2001-05-15 | 2005-05-05 | Hydrogenics Corporation | Fuel cell stack |
| US20040258977A1 (en) * | 2003-01-24 | 2004-12-23 | Hydrogenics Corporation | Apparatus for and method of forming seals in fuel cells and fuel cell stacks |
| US6852439B2 (en) | 2001-05-15 | 2005-02-08 | Hydrogenics Corporation | Apparatus for and method of forming seals in fuel cells and fuel cell stacks |
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| NL137652C (enFirst) * | 1962-07-11 | |||
| GB1103202A (en) * | 1963-08-09 | 1968-02-14 | Dunlop Co Ltd | Improvements relating to encapsulated materials |
| US3284406A (en) * | 1963-12-18 | 1966-11-08 | Dow Corning | Organosiloxane encapsulating resins |
| NL131800C (enFirst) * | 1965-05-17 | |||
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| US3635667A (en) * | 1970-07-23 | 1972-01-18 | Fmc Corp | Drycleaning with hydrogen peroxide |
| GB1354694A (en) * | 1970-08-13 | 1974-06-05 | Magnesium Elektron Ltd | Encapsulation of fluids and solids |
| US3954678A (en) * | 1974-07-11 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Semipermeable microcapsules containing a silica gel |
| DE2734577A1 (de) * | 1977-07-30 | 1979-02-08 | Bayer Ag | Polymerloesungen |
| JPS55161849A (en) * | 1979-06-04 | 1980-12-16 | Toray Silicone Co Ltd | Organopolysiloxane composition |
| US4225460A (en) * | 1979-06-28 | 1980-09-30 | Minnesota Mining And Manufacturing Company | Latent Lewis acid catalyst system and process |
| DE3016170A1 (de) * | 1980-04-26 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | Mikrokapseln mit definierter oeffnungstemperatur, verfahren zu deren herstellung sowie deren verwendung |
| US4389330A (en) * | 1980-10-06 | 1983-06-21 | Stolle Research And Development Corporation | Microencapsulation process |
| JPS57123532A (en) * | 1981-01-20 | 1982-08-02 | Fuji Photo Film Co Ltd | Magnetic recording medium |
| DE3131734A1 (de) * | 1981-08-11 | 1983-02-24 | Bayer Ag, 5090 Leverkusen | Hitzehaertbare organopolysiloxan-mischungen |
| DE3268643D1 (en) * | 1981-08-14 | 1986-03-06 | Ici Plc | Catalysts |
| JPS5858146A (ja) * | 1981-10-05 | 1983-04-06 | Tanabe Seiyaku Co Ltd | 速放性マイクロカプセル |
| US4421903A (en) * | 1982-02-26 | 1983-12-20 | General Electric Company | Platinum complex catalysts |
| JPS5916821A (ja) * | 1982-07-16 | 1984-01-28 | Tanabe Seiyaku Co Ltd | 非凝集性マイクロカプセルの製法 |
| US4546164A (en) * | 1982-11-29 | 1985-10-08 | Sws Silicones Corporation | Process for preparing a one-component organopolysiloxane composition |
| FR2553784B1 (fr) * | 1983-10-19 | 1986-12-12 | Rhone Poulenc Spec Chim | Encapsulation de l'accelerateur de durcissement de compositions organopolysiloxaniques contenant des polyacyloxysilanes et durcissant en elastomeres |
| US4528354A (en) * | 1984-04-25 | 1985-07-09 | Mcdougal John R | Process and composition for the manufacture of products from silicone rubber |
| US4613659A (en) * | 1985-12-16 | 1986-09-23 | Dow Corning Corporation | Low temperature polymethylsiloxane containing silicon-bonded hydrogen and curable compositions made therewith |
| US4766176A (en) * | 1987-07-20 | 1988-08-23 | Dow Corning Corporation | Storage stable heat curable organosiloxane compositions containing microencapsulated platinum-containing catalysts |
| US4874667A (en) * | 1987-07-20 | 1989-10-17 | Dow Corning Corporation | Microencapsulated platinum-group metals and compounds thereof |
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- 1987-07-20 US US07/075,790 patent/US4784879A/en not_active Expired - Fee Related
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1988
- 1988-07-06 CA CA000571228A patent/CA1338200C/en not_active Expired - Fee Related
- 1988-07-07 DE DE3852120T patent/DE3852120T2/de not_active Expired - Fee Related
- 1988-07-07 EP EP88306214A patent/EP0300644B1/en not_active Expired - Lifetime
- 1988-07-19 AU AU19144/88A patent/AU602102B2/en not_active Ceased
- 1988-07-19 JP JP63178301A patent/JPS6447442A/ja active Granted
- 1988-07-19 BR BR8803620A patent/BR8803620A/pt unknown
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| EP0300644B1 (en) | 1994-11-17 |
| DE3852120T2 (de) | 1995-06-01 |
| EP0300644A2 (en) | 1989-01-25 |
| JPS6447442A (en) | 1989-02-21 |
| JPH0569580B2 (enFirst) | 1993-10-01 |
| US4784879A (en) | 1988-11-15 |
| DE3852120D1 (de) | 1994-12-22 |
| AU1914488A (en) | 1989-01-27 |
| BR8803620A (pt) | 1989-02-08 |
| EP0300644A3 (en) | 1989-11-02 |
| AU602102B2 (en) | 1990-09-27 |
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