WO1997038041B1 - Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders - Google Patents
Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powdersInfo
- Publication number
- WO1997038041B1 WO1997038041B1 PCT/US1997/005179 US9705179W WO9738041B1 WO 1997038041 B1 WO1997038041 B1 WO 1997038041B1 US 9705179 W US9705179 W US 9705179W WO 9738041 B1 WO9738041 B1 WO 9738041B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ceramic powder
- coated
- ceramic
- siloxane
- powder
- Prior art date
Links
- 239000000919 ceramic Substances 0.000 title claims abstract 43
- 239000000843 powder Substances 0.000 title claims abstract 35
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 title claims abstract 20
- 229920000578 graft polymer Polymers 0.000 title claims 3
- 239000000178 monomer Substances 0.000 claims abstract 8
- 239000002245 particle Substances 0.000 claims abstract 7
- 229920001688 coating polymer Polymers 0.000 claims abstract 6
- 229920000642 polymer Polymers 0.000 claims abstract 6
- 230000000379 polymerizing Effects 0.000 claims abstract 2
- 229910000460 iron oxide Inorganic materials 0.000 claims 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims 3
- LIKFHECYJZWXFJ-UHFFFAOYSA-N Dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims 3
- NRAYZPGATNMOSB-UHFFFAOYSA-N dichloro(dihexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)CCCCCC NRAYZPGATNMOSB-UHFFFAOYSA-N 0.000 claims 3
- KKRMHVJQWMXYBZ-UHFFFAOYSA-N dichloro-hexyl-methylsilane Chemical compound CCCCCC[Si](C)(Cl)Cl KKRMHVJQWMXYBZ-UHFFFAOYSA-N 0.000 claims 3
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 claims 3
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims 3
- GOIPELYWYGMEFQ-UHFFFAOYSA-N dimethoxy-methyl-octylsilane Chemical compound CCCCCCCC[Si](C)(OC)OC GOIPELYWYGMEFQ-UHFFFAOYSA-N 0.000 claims 3
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 claims 3
- RUFRLNPHRPYBLF-UHFFFAOYSA-N methoxy-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)OC RUFRLNPHRPYBLF-UHFFFAOYSA-N 0.000 claims 3
- SLYCYWCVSGPDFR-UHFFFAOYSA-N Octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 claims 2
- ZVMRWPHIZSSUKP-UHFFFAOYSA-N dicyclohexyl(dimethoxy)silane Chemical compound C1CCCCC1[Si](OC)(OC)C1CCCCC1 ZVMRWPHIZSSUKP-UHFFFAOYSA-N 0.000 claims 2
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 claims 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims 2
- AILBOMWJRYLVFG-UHFFFAOYSA-N dodecyl-diethoxy-methylsilane Chemical compound CCCCCCCCCCCC[Si](C)(OCC)OCC AILBOMWJRYLVFG-UHFFFAOYSA-N 0.000 claims 2
- CZWLNMOIEMTDJY-UHFFFAOYSA-N hexyl(trimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)OC CZWLNMOIEMTDJY-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 claims 2
- 238000009877 rendering Methods 0.000 claims 2
- -1 triethyleilanol Chemical compound 0.000 claims 2
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 claims 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical group CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N Dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 claims 1
- WVMSIBFANXCZKT-UHFFFAOYSA-N triethyl(hydroxy)silane Chemical compound CC[Si](O)(CC)CC WVMSIBFANXCZKT-UHFFFAOYSA-N 0.000 claims 1
Abstract
A coated ceramic powder comprises a plurality of ceramic particles and a siloxane star-graft coating polymer encapsulating at least a portion of the particles. The coating polymer comprises Si(w,x,y,z), where w, x, y and z are the mole percent tetrafunctional, trifunctional, difunctional and monofunctional monomeric units, respectively, and wherein w is about 20-100 and x, y and z are about 0-30, 0-50 and 0-10, respectively, and at least one of x, y and z is greater than zero. A method of preparing a coated ceramic powder comprises the steps of a) polymerizing a tetrafunctional siloxane monomer and at least one of a trifunctional siloxane monomer, a difunctional siloxane monomer and a monofunctional siloxane monomer, b) adding a quantity of ceramic powder to a reaction vessel, c) shear mixing the ceramic powder for a time sufficient to wet substantially all of the powder surface, d) adding the siloxane polymer prepared in step (a) to the reaction vessel containing the shear mixed ceramic powder, e) shear mixing the shear mixed ceramic powder and the siloxane polymer for a time sufficient to form a siloxane polymer coated ceramic powder, and f) separating the coated ceramic powder from the components remaining in the reaction vessel.
Claims
1. A coated ceramic powder comprising a plurality of ceramic particles and a siloxane star- graft coating polymer encapsulating at least a portion of said particles, said coating polymer comprising:
Si(w,x.y,z)
where w, x, y and z are the mole percent tetrafunctional, trifunctional, difunctional and monofunctional monomeric units, respectively, and wherein w, x, y and z are about 45-75, 5-25, 5-45 and 5-10, respectively.
2. The coated ceramic powder of claim 1 wherein said ceramic is Ti02.
3. The coated ceramic powder of claim 2 further comprising Al"5 centers to introduce surface defects into the Ti02 powder, thereby rendering said coated Ti02 powder non-photoactive.
4. The coated ceramic powder of claim 1 wherein said ceramic iε Al203.
5. The coated ceramic powder of claim 1 wherein said ceramic is ZnO.
6. The coated ceramic powder of claim 1 wherein said ceramic is an iron oxide.
7. The coated ceramic powder of claim 6 wherein said iron oxide is 7-Fe203. - -
8. The coated ceramic powder of claim 6 wherein said iron oxide is α-Fe-Oj.
9. The coated ceramic powder of claim 6 wherein said iron oxide is Fe30,.
10. The coated ceramic powder of claim 1 wherein said ceramic is Si02.
11. The coated ceramic powder of claim l wherein: w is tetraethylorthosilicate; x is selected from the group consisting of γ-glycidoxypropyltrimethoxysilane, n- hexyltrimethoxysilaπe, isobutyltrimethoxy-' silane, γ-methacryloxypropyltrimethoxysilane, n-octadecyltrimethoxyεilane, and n-propyltri- methoxysilane; y is selected from the group consisting of dicyclohexyldimethoxysilane, diethyldieth- oxysilane, dimethyldichlorosilane, dimethyl- diethoxysilane, dimethyldimethoxysilane, diphenyldiethoxysilane, diphenyldimethoxy- silane, di-n-hexyldichlorosilane, n-hexyl- methyldichlorosilane, methyldodecyldiethoxy- silane, neophylmethyldimethoxysilane, and n- octylmethyldimethoxysilane; and z is selected from the group consisting of n-octadecyldimethylmethoxysilane, triethyl- silanol, trimethylethoxysilane, and trimethyl- methoxysilane.
12. A method of preparing a coated ceramic powder comprising a plurality of ceramic particles and a siloxane star-graft coating polymer encapsulating at least a portion of said particles, the method comprising the steps of : (a) polymerizing tetrafunctional, trifunctional, difunctional and monofunctional siloxane monomers;
(b) adding a quantity of ceramic powder to a reaction vessel;
(c) shear mixing said ceramic powder for a time sufficient to wet substantially all of said powder surface; (d) adding the siloxane polymer prepared in step (a) to said reaction vessel containing said shear mixed ceramic powder;
(e) shear mixing said shear mixed ceramic powder and said siloxane polymer for a time sufficient to form a siloxane polymer coated ceramic powder;
(f) separating said coated ceramic powder from the components remaining in said reaction vessel.
13. The method of claim 12 wherein said ceramic is Tiθ2.
14. The method of claim 13 wherein a further quantity of aluminum tri-sec-butoxide is added to the reaction vessel in step (b) to introduce surface defects into said TiO- powder, thereby rendering said coated Ti02 powder non-photoactive.
15. The method of claim 12 wherein said ceramic is A1203.
16. The method of claim 12 wherein said ceramic is ZnO.
17. The method of claim 12 wherein said ceramic is an iron oxide.
18. The method of claim 17 wherein said iron oxide is γ-Fe203.
19. The method of claim 17 wherein said iron oxide is α-Fe203.
20. The method of claim 17 wherein said iron oxide is Fe30<.
21. The method of claim 12 wherein said ceramic is Si02.
22. The method of claim 12 wherein: said tetrafunctional siloxane monomer is tetraethylorthosilicate,- said trifunctional siloxane monomer is selected from the group consisting of γ- glycidoxypropyltrimethoxyeilane, n- hexyltrimethoxysilane, isobutyltrimethoxy- silane, γ-methacryloxypropyltrimethoxysilane, n-octadecyltrimethoxysilane, and n-propyltri- methoxysi1ane; said difunctional siloxane monomer is selected from the group conεisting of dicyclohexyldimethoxysilane, diethyldiethoxysilane, dimethyldichlorosilane, dimethyldiethoxyεilane, dimethyldimeth- oxyeilane, diphenyldiethoxysilane, diphenyldi- methoxysilane, di-n-hexyldichlorosilane, n- hexylmethyldichlorosilane, methyldodecyl- diethoxysilane, neophylmethyldimethoxysilane, and n-octylmethyldimethoxysilane; and said monofunctional siloxane monomer is selected from the group consisting of n- _24_ 1
octadecyldimethylmethoxysilane, triethyleilanol, trimethylethoxysilane, and trimethyl-methoxysilaπe.
23. The coated ceramic powder prepared according to the method of any one of claims 12-22.
24. A siloxane star-graft polymer for coating and encapsulating ceramic particles, said coating polymer comprising:
where w, x, y and z are the mole percent tetrafunctional, trifunctional, difunctiσnal and monofunctional monomeric units, respectively, and wherein w, x, y and z are about 45-75, 5-25, 5-45 and 5-10, respectively.
25. The star-graft polymer of claim 24 wherein: w is tetraethylorthosilicate,- x is selected from the group consisting of γ-glycidoxypropyltrimethoxysilane, n- hexyltrimethoxysilane, isobutyltrimethoxy- silane, γ-methacryloxypropyltrimethoxysilane, n-octadecyltrimethoxysilane, and n-propyltri- methoxysilane; y ie selected from the group consisting of dicyclohexyldimethoxyεilane, diethyldieth¬ oxysilane, dimethyldichlorosilane, dimethyl- diethoxyεilane, dimethyldimethoxysilane, diphenyldiethoxysilane, diphenyldimethoxy- silane, di-n-hexyldichlorosilane, n-hexyl- methyldichlorosilane, methyldodecyldiethoxy- εilane, neophylmethyldimethoxysilane, and n- octylmethyldimethoxysilane; and z is selected from the group consisting of n-octadecyldimethylmethoxysilane, triethyl- εilanol, trimethylethoxysilane, and trimethyl- methoxysilane.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002250962A CA2250962C (en) | 1996-04-04 | 1997-03-28 | Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders |
| EP97919963A EP0891387B1 (en) | 1996-04-04 | 1997-03-28 | Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders |
| AU24271/97A AU715859B2 (en) | 1996-04-04 | 1997-03-28 | Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders |
| JP9536259A JP2000508684A (en) | 1996-04-04 | 1997-03-28 | Siloxane star graft polymer, ceramic powder coated thereby, and method for preparing coated ceramic powder |
| DE69729290T DE69729290T2 (en) | 1996-04-04 | 1997-03-28 | STARTER-MOLDED SILOXANE POLYMERS, CERAMIC POWDER COATED THEREFOR, AND A METHOD FOR THE PRODUCTION THEREOF |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1483896P | 1996-04-04 | 1996-04-04 | |
| US60/014,838 | 1996-04-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997038041A1 WO1997038041A1 (en) | 1997-10-16 |
| WO1997038041B1 true WO1997038041B1 (en) | 1997-11-06 |
Family
ID=21768045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/005179 WO1997038041A1 (en) | 1996-04-04 | 1997-03-28 | Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6033781A (en) |
| EP (1) | EP0891387B1 (en) |
| JP (2) | JP2000508684A (en) |
| AU (1) | AU715859B2 (en) |
| CA (1) | CA2250962C (en) |
| DE (1) | DE69729290T2 (en) |
| WO (1) | WO1997038041A1 (en) |
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| US4574082A (en) * | 1983-07-29 | 1986-03-04 | Revlon, Inc. | One-phase silicone-based cosmetic products containing wax |
| US4644077A (en) * | 1984-07-11 | 1987-02-17 | The Sherwin-Williams Company | Process for producing organophilic silica |
| US4818614A (en) * | 1985-07-29 | 1989-04-04 | Shiseido Company Ltd. | Modified powder |
| DE3684836D1 (en) * | 1985-07-29 | 1992-05-21 | Shiseido Co Ltd | POWDER COVERED WITH SILICONE POLYMER OR PARTICULAR MATERIAL. |
| US5143722B1 (en) * | 1986-12-19 | 1999-08-24 | Revlon Consumer Prod Corp | Cosmetic makeup compositions comprising water-in-oil emulsions containing pigment |
| GB8712752D0 (en) * | 1987-05-30 | 1987-07-01 | Tioxide Group Plc | Particulate material |
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-
1997
- 1997-03-28 EP EP97919963A patent/EP0891387B1/en not_active Expired - Lifetime
- 1997-03-28 US US08/827,229 patent/US6033781A/en not_active Expired - Lifetime
- 1997-03-28 JP JP9536259A patent/JP2000508684A/en not_active Withdrawn
- 1997-03-28 WO PCT/US1997/005179 patent/WO1997038041A1/en active IP Right Grant
- 1997-03-28 AU AU24271/97A patent/AU715859B2/en not_active Expired
- 1997-03-28 CA CA002250962A patent/CA2250962C/en not_active Expired - Lifetime
- 1997-03-28 DE DE69729290T patent/DE69729290T2/en not_active Expired - Lifetime
-
2006
- 2006-09-13 JP JP2006248645A patent/JP2007092063A/en active Pending
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