WO1997014735B1 - Fluorinated polyisocyanates - Google Patents
Fluorinated polyisocyanatesInfo
- Publication number
- WO1997014735B1 WO1997014735B1 PCT/US1996/016270 US9616270W WO9714735B1 WO 1997014735 B1 WO1997014735 B1 WO 1997014735B1 US 9616270 W US9616270 W US 9616270W WO 9714735 B1 WO9714735 B1 WO 9714735B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fluorinated
- polyisocyanate
- carbon atoms
- monofunctional alcohol
- diisocyanate
- Prior art date
Links
- 229920001228 Polyisocyanate Polymers 0.000 title claims abstract 12
- 239000005056 polyisocyanate Substances 0.000 title claims abstract 12
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005442 diisocyanate group Chemical group 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive Effects 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 229920000058 polyacrylate Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000000565 sealant Substances 0.000 abstract 1
Abstract
A fluorinated polyisocyanate which comprises an organic polyisocyanate reacted with a fluorinated monofunctional alcohol represented by formula (I), where Rf is a fluoroalkyl containing group having at least 4 carbon atoms, X is a divalent radical, R3 is H or an alkyl group having 1-4 carbon atoms, n is 0-1 and m is 0-30, provided that when n is 0 then m must be equal to or greater than 1 and when m is 0, n is 1, wherein about 0.1-33 mole percent of active isocyanate groups are reacted with the fluorinated monofunctional alcohol; the fluorinated polyisocyanate can be used with acrylic polymers, polyesters, alkyl resins, polyols and the like to form coating compositions, sealants, adhesives and the like.
Claims
1. A fluorinated polyisocyanate which comprises an organic polyisocyanate reacted with a fluorinated monofunctional alcohol represented by the formula
2. The fluorinated polyisocyanate of claim 1 in which Rf is a straight chain or branched chain perfluoroalkyl group having 4-20 carbon atoms.
3. The fluorinated polyisocyanate of claim 2 in which X is -O-, -CH2CH20-, -CH2O-, -SO2N(R4)CH2CH 0-, -CH2- where R4 is an alkyl group having 1-4 carbon atoms, R3 is H or methyl.
4. The fluorinated polyisocyanate of claim 1 in which the organic polyisocyanate is an aromatic diisocyanate, aliphatic diisocyanate, cycloaliphatic diisocyanate, aromatic triisocyanate, aliphatic triisocyanate, cycloaliphatic triisocyanate or an oligomer of a diisocyanate.
5. A process for forming the fluorinated polyisocyanate of claim 1 which comprises reacting a fluorinated monofunctional alcohol represented by the formula
R3
Rf— (X)n— (CH^H-OJm-H where Rf is a fluoroalkyl group containing at least 4 carbon atoms, X is a divalent radical, R3 is H or an alkyl group having 1-4 carbon atoms, n is 1 and m is 1-30, with an organic polyisocyanate in the
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96936351A EP0856022B1 (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanates |
BR9611085A BR9611085A (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanate for the formation of fluorinated polyisocyanate composition and substrate |
DE69603282T DE69603282T2 (en) | 1995-10-16 | 1996-10-11 | FLUORRINATED POLYISOLYANATE |
JP9515880A JPH11513732A (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanate |
AU74380/96A AU718618B2 (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanates |
BR9611589-0A BR9611589A (en) | 1995-11-06 | 1996-10-11 | Process for manufacturing decomposition of automatic dish washing containing diacyl peroxide |
NZ321104A NZ321104A (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanates containing organic polyisocyanates with a fluorinated alcohol used to form sealants, coating compositions and adhesives |
CA 2234371 CA2234371C (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/543,773 US5605956A (en) | 1995-10-16 | 1995-10-16 | Fluorinated polyisocyanates |
US08/543,773 | 1995-10-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1997014735A1 WO1997014735A1 (en) | 1997-04-24 |
WO1997014735B1 true WO1997014735B1 (en) | 1997-05-15 |
Family
ID=24169512
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/016270 WO1997014735A1 (en) | 1995-10-16 | 1996-10-11 | Fluorinated polyisocyanates |
Country Status (9)
Country | Link |
---|---|
US (1) | US5605956A (en) |
EP (1) | EP0856022B1 (en) |
JP (1) | JPH11513732A (en) |
AU (1) | AU718618B2 (en) |
BR (1) | BR9611085A (en) |
DE (1) | DE69603282T2 (en) |
MX (1) | MX201366B (en) |
NZ (1) | NZ321104A (en) |
WO (1) | WO1997014735A1 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6413588B1 (en) * | 1999-01-11 | 2002-07-02 | E. I. Du Pont De Nemours And Company | Method of producing durable layered coatings |
US6673889B1 (en) * | 1999-06-28 | 2004-01-06 | Omnova Solutions Inc. | Radiation curable coating containing polyfuorooxetane |
EP1265827B1 (en) | 2000-02-22 | 2006-07-05 | E.I. Dupont De Nemours And Company | A method for protection of stone with fluorinated urethane |
DE10208567A1 (en) * | 2002-02-27 | 2003-09-11 | Degussa Construction Chem Gmbh | Aqueous fluorine-modified polyurethane system for anti-graffiti and anti-soiling coatings |
US6933005B2 (en) * | 2003-09-22 | 2005-08-23 | E. I. Du Pont De Nemours And Company | Method for achieving recoat adhesion over a fluorinated topcoat |
US7288282B2 (en) * | 2003-09-22 | 2007-10-30 | E. I. Du Pont De Nemours And Company | Coating compositions containing a fluorinated organosilane polymer |
US7348389B2 (en) * | 2003-09-22 | 2008-03-25 | E. I. Du Pont De Nemours And Company | Method for achieving recoat adhesion over a fluorinated topcoat |
US9464160B2 (en) * | 2010-08-27 | 2016-10-11 | The Chemours Company Fc, Llc | Fluorinated ethoxylated polyurethanes |
EP2904026B1 (en) | 2012-10-04 | 2018-08-15 | BASF Coatings GmbH | Nonaqueous coating composition containing fluorine, coating process and use of said coating composition |
EP2716680A1 (en) | 2012-10-04 | 2014-04-09 | Basf Se | Fluorinated polymerizable compound |
CN107001855B (en) * | 2014-12-08 | 2020-12-04 | 巴斯夫涂料有限公司 | Non-aqueous coating composition, coating prepared therefrom with improved adhesion and scratch resistance and use thereof |
CN107001854B (en) * | 2014-12-08 | 2021-01-15 | 巴斯夫涂料有限公司 | Coating composition and coating prepared therefrom and use thereof |
CN112480355B (en) * | 2020-12-04 | 2022-07-05 | 上海应用技术大学 | Low-surface-energy resin emulsion and preparation method thereof |
CN112480304A (en) * | 2020-12-04 | 2021-03-12 | 上海应用技术大学 | Functional emulsion and preparation method thereof |
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US2803615A (en) * | 1956-01-23 | 1957-08-20 | Minnesota Mining & Mfg | Fluorocarbon acrylate and methacrylate esters and polymers |
US3255131A (en) * | 1961-05-10 | 1966-06-07 | Minnesota Mining & Mfg | Fluorochemical-containing varnishes |
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US3318852A (en) * | 1965-04-05 | 1967-05-09 | Minnesota Mining & Mfg | Fluorine-containing polymers |
US3478116A (en) * | 1967-07-26 | 1969-11-11 | Du Pont | Fluorinated alcohols |
US3972856A (en) * | 1969-03-10 | 1976-08-03 | Minnesota Mining And Manufacturing Company | Polyurethanes containing poly(perfluoroalkylene oxides) units |
US3759874A (en) * | 1971-08-30 | 1973-09-18 | Fmc Corp | Fluorinated polyurethanes as soil release agents |
FR2476097A1 (en) * | 1980-02-19 | 1981-08-21 | Ugine Kuhlmann | |
US4371657A (en) * | 1981-03-04 | 1983-02-01 | E. I. Du Pont De Nemours And Company | Crater resistant acrylic enamel |
US4396680A (en) * | 1981-03-04 | 1983-08-02 | E. I. Du Pont De Nemours And Co. | Substrate coated with crater resistant acrylic enamel |
JPS60184513A (en) * | 1984-03-02 | 1985-09-20 | Showa Denko Kk | Production of graft polymer |
JPS6114267A (en) * | 1984-06-29 | 1986-01-22 | Showa Denko Kk | Water-and oil-repellent paint |
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JPS6123656A (en) * | 1984-07-11 | 1986-02-01 | Kansai Paint Co Ltd | Anti-icing organic coating composition |
JPS6163646A (en) * | 1984-09-04 | 1986-04-01 | Sannopuko Kk | Fluorine-containing isocyanate compound and surface treatment using same |
JPS6195078A (en) * | 1984-10-15 | 1986-05-13 | Kansai Paint Co Ltd | Anti-icing organic resin coating composition |
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DE3943127A1 (en) * | 1989-12-28 | 1991-07-04 | Hoechst Ag | URETHANES AS ALIPHATIC FLUORO ALCOHOL, ISOCYANATES AND CARBONIC ACIDS, PROCESS FOR THEIR PREPARATION AND THEIR USE |
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DE4136768A1 (en) * | 1991-11-08 | 1993-05-13 | Bayer Ag | THE USE OF POLYISOCYANATE SOLUTIONS FOR IMPREGNATING MINERAL SUBSTANCES |
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US5484818A (en) * | 1993-07-22 | 1996-01-16 | Imperial Chemical Industries Plc | Organic aerogels |
US5541281A (en) * | 1994-12-20 | 1996-07-30 | Bayer Corporation | Low surface energy polyisocyanates and their use in one- or two-component coating compositions |
-
1995
- 1995-10-16 US US08/543,773 patent/US5605956A/en not_active Expired - Lifetime
-
1996
- 1996-10-11 EP EP96936351A patent/EP0856022B1/en not_active Expired - Lifetime
- 1996-10-11 AU AU74380/96A patent/AU718618B2/en not_active Ceased
- 1996-10-11 BR BR9611085A patent/BR9611085A/en not_active IP Right Cessation
- 1996-10-11 WO PCT/US1996/016270 patent/WO1997014735A1/en active IP Right Grant
- 1996-10-11 DE DE69603282T patent/DE69603282T2/en not_active Expired - Fee Related
- 1996-10-11 JP JP9515880A patent/JPH11513732A/en not_active Ceased
- 1996-10-11 NZ NZ321104A patent/NZ321104A/en unknown
-
1998
- 1998-03-31 MX MX9802512A patent/MX201366B/en not_active IP Right Cessation
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