WO1997014733B1 - Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate - Google Patents
Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanateInfo
- Publication number
- WO1997014733B1 WO1997014733B1 PCT/US1996/016289 US9616289W WO9714733B1 WO 1997014733 B1 WO1997014733 B1 WO 1997014733B1 US 9616289 W US9616289 W US 9616289W WO 9714733 B1 WO9714733 B1 WO 9714733B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- carbon atoms
- ofthe
- alkyl
- acrylic polymer
- Prior art date
Links
- 239000008199 coating composition Substances 0.000 title claims abstract 10
- 229920001228 Polyisocyanate Polymers 0.000 title claims abstract 7
- 239000005056 polyisocyanate Substances 0.000 title claims abstract 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims 2
- 229920002313 fluoropolymer Polymers 0.000 title 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract 11
- 239000011230 binding agent Substances 0.000 claims abstract 10
- 229920000058 polyacrylate Polymers 0.000 claims abstract 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract 7
- 239000000178 monomer Substances 0.000 claims abstract 6
- 239000000203 mixture Substances 0.000 claims abstract 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract 3
- 239000003431 cross linking reagent Substances 0.000 claims abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 239000007788 liquid Substances 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- -1 hydroxy alkyl methacrylates Chemical class 0.000 claims 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 3
- 239000000758 substrate Substances 0.000 claims 3
- 125000005442 diisocyanate group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 230000003078 antioxidant Effects 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N butyl 2-methylprop-2-enoate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 1
- 238000005227 gel permeation chromatography Methods 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 2
Abstract
A coating composition containing about 45-80 % by weight of a binder and 20-55 % by weight of an organic liquid; wherein the binder contains (A) about 40-90 % by weight, based on the weight of the binder, of an acrylic polymer containing polymerized hydroxyl containing monomers of the following group of hydroxy alkyl acrylate or methacrylates having 1-4 carbon atoms in the alkyl group, and polymerized alkyl acrylates and methacrylates having 1-18 carbon atoms in the alkyl groups, or styrene or any mixtures of the above and 0.1-5.0 % by weight, based on the weight of the acrylic polymer, of polymerized fluoroalkyl containing monomer represented by formula (I) where R is hydrogen or an alkyl group having 1-2 carbon atoms, n is an integer of 1-11 and Rf is a fluoroalkyl containing group having at least 4 carbon atoms and (B) about 10-60 % by weight, based on the weight of the binder, of a fluorinated organic polyisocyanate cross-linking agent.
Claims
1. A coating composition containing about 45-80% by weight ofa binder and 20-55% by weight of an organic liquid; wherein the binder comprises (A) about 40-90% by weight, based on the weight ofthe binder, of an acrylic polymer consisting essentially of about 20-45% by weight, based on the weight ofthe acrylic polymer, of polymerized hydroxyl containing monomers selected from the group consisting of hydroxy alkyl acrylate and hydroxy alkyl methacrylates having 1-4 carbon atoms in the alkyl groups, 50
- 79.9% by weight, based on the weight ofthe acrylic polymer, of polymerized monomers selected from the group consisting of alkyl acrylates and alkyl methacrylates having 1 - 18 carbon atoms in the alkyl groups, styrene and any mixtures ofthe above and 0.1 - 5.0% by weight, based on the weight ofthe acrylic polymer, of polymerized fluoroalkyl contaming monomer represented by the formula
CH2= CR C O (CHsJn Rf where R is selected from the group consisting of hydrogen or an alkyl group having 1 - 2 carbon atoms, n is an integer of 1 -
11 and R is a fluoroalkyl containing group having at least 4 carbon atoms and the acrylic polymer having a weight average molecular weight of about 2,000 - 20,000 determined by gel permeation chromatography, and (B) about 10-60% by weight, based on the weight ofthe binder, of a fluorinated organic polyisocyanate crosslinking agent consisting essentially of an adduct ofa fluorinated monofunctional alcohol and an organic polyisocyanate where the fluorinated monofunctional alcohol is represented by the formula
where Rf is as defined above, 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 and where about 0.1-33 mole percent of active isocyanate groups are reacted with the fluorinated monofunctional alcohol.
2. The coating composition of Claim 1 in which Rf ofthe fluoroalkyl monomer ofthe acrylic polymer and the fluorinated organic polyisocyanate is a straight chain or branched chain perfluoroalkyl group having 4-20 carbon atoms.
3. The coating compositions of Claim 2 in which the acrylic polymer consists essentially of polymerized monomers of an alkyl methacrylate having 2-6 carbon atoms in the alkyl groups, an alkyl acrylate having 2-8 carbon atoms in the alkyl group, a hydroxy alkyl acrylate having 2-4 carbon atoms in the alkyl group, styrene and a fluoroalkyl containing monomer wherein R is CH3 and n is 2.
4. The coating composition of Claim 3 in which the acrylic polyerm consists essentially of butyl methacrylate, butyl acrylate, styrene, hydroxy propyl acrylate and the perfluoroalkyl contaming monomer.
5. The coating composition of Claim 3 in which the fluoroalkyl containing monomer ofthe acrylic polymer is represented by the formula
Rl is a perfluoroalkyl group having 4-12 carbon atoms,
R2 is an alkyl group having 1-4 carbon atoms and n is an integer of 1-
6. The coating composition of Claim 1 in the fluorinated monofunctional alcohol X is -O-, -CH2O-, CH2CH2O-, -SO2N(R4)CH2CH2O-, CH2- where R4 is H or methyl.
7. The coating composition 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 ofa diisocyanate.
19
8. The coating composition of Claim 1 containing about 0.1-10% by weight, based on the weight ofthe binder, of ultraviolet light stabilizers or an antioxidant or mixtures thereof.
9. A substrate coated with a dried and cured layer ofthe composition of Claim 1.
10. A substrate coated with a pigmented base coat on which is coated a clear layer ofthe dried and cured composition of Claim 1.
11. The coated substrate of Claim 10 in which the pigmented base coat contains about 10-40% by weight, based on the weight of binder ofthe base coat, ofa fluorinated polyisocyanate crosslinking agent.
20
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96936367A EP0856021B1 (en) | 1995-10-16 | 1996-10-11 | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
| NZ321114A NZ321114A (en) | 1995-10-16 | 1996-10-11 | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
| CA002234421A CA2234421C (en) | 1995-10-16 | 1996-10-11 | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
| JP51588497A JP4074340B2 (en) | 1995-10-16 | 1996-10-11 | Coating composition of acrylic fluorocarbon polymer and fluorinated polyisocyanate |
| AU74392/96A AU706335B2 (en) | 1995-10-16 | 1996-10-11 | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
| DE69603195T DE69603195T2 (en) | 1995-10-16 | 1996-10-11 | COATING COMPOSITIONS OF AN ACRYLIC FLUOROCOLATE POLYMER AND A FLUORINE POLYISOCYANATE |
| BR9611102A BR9611102A (en) | 1995-10-16 | 1996-10-11 | Coating composition and coated substrate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/543,721 US5597874A (en) | 1995-10-16 | 1995-10-16 | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
| US08/543,721 | 1995-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997014733A1 WO1997014733A1 (en) | 1997-04-24 |
| WO1997014733B1 true WO1997014733B1 (en) | 1997-05-15 |
Family
ID=24169307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/016289 WO1997014733A1 (en) | 1995-10-16 | 1996-10-11 | Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US5597874A (en) |
| EP (1) | EP0856021B1 (en) |
| JP (1) | JP4074340B2 (en) |
| AU (1) | AU706335B2 (en) |
| BR (1) | BR9611102A (en) |
| CA (1) | CA2234421C (en) |
| DE (1) | DE69603195T2 (en) |
| NZ (1) | NZ321114A (en) |
| WO (1) | WO1997014733A1 (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5914384A (en) * | 1997-11-21 | 1999-06-22 | E. I. Du Pont De Nemours And Company | Coating compositions containing a highly fluorinated hydroxyl containing additive |
| US6168866B1 (en) | 1998-08-19 | 2001-01-02 | 3M Innovative Properties Company | Abrasion and stain resistant curable fluorinated coating |
| US6583223B2 (en) | 2001-09-27 | 2003-06-24 | Ppg Industries Ohio, Inc. | Coating compositions which contain a low surface tension (meth) acrylate containing block copolymer flow control agent |
| US6586530B1 (en) | 2001-09-27 | 2003-07-01 | Ppg Industries Ohio, Inc. | Low surface tension (meth) acrylate containing block copolymer prepared by controlled radical polymerization |
| US6841641B2 (en) * | 2001-09-27 | 2005-01-11 | Ppg Industries Ohio, Inc. | Copolymers comprising low surface tension (meth) acrylates |
| 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 |
| US7288282B2 (en) * | 2003-09-22 | 2007-10-30 | E. I. Du Pont De Nemours And Company | Coating compositions containing a fluorinated organosilane polymer |
| 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 |
| US8431216B2 (en) * | 2007-05-05 | 2013-04-30 | Lg Display Co., Ltd. | Optical film for a display device and method of fabricating the same |
| US9464160B2 (en) | 2010-08-27 | 2016-10-11 | The Chemours Company Fc, Llc | Fluorinated ethoxylated polyurethanes |
| CN104159944B (en) | 2011-11-30 | 2015-11-25 | 涂层国外知识产权有限公司 | Varnish colour composition |
| WO2013081815A1 (en) | 2011-11-30 | 2013-06-06 | U.S. Coatings Ip Co. Llc | Clear coat coating composition |
| US20140329934A1 (en) | 2011-11-30 | 2014-11-06 | Axalta Coating Systems Ip Co., Llc | Coating composition |
| WO2013081816A1 (en) | 2011-11-30 | 2013-06-06 | U.S. Coatings Ip Co. Llc | Clear coat coating composition |
| RU2494875C1 (en) * | 2012-02-29 | 2013-10-10 | Закрытое акционерное общество по разработке и внедрению новых информационных материалов и технологий "БИТ" | Protective coating for power-saving films |
| CN105765012B (en) | 2013-11-20 | 2019-08-16 | 大阪有机化学工业株式会社 | Clear coating composition |
| JP6157442B2 (en) * | 2013-12-25 | 2017-07-05 | 大阪有機化学工業株式会社 | Clear coat composition |
| ES2740125T3 (en) * | 2014-12-08 | 2020-02-05 | Basf Coatings Gmbh | Non-aqueous compositions of coating agents, coatings manufactured from them, with improved scratch resistance and adhesion, as well as their use |
| CA2970120C (en) * | 2014-12-08 | 2019-10-15 | Basf Coatings Gmbh | Coating material compositions and coatings produced therefrom and also use thereof |
| CN104710557A (en) * | 2014-12-31 | 2015-06-17 | 佛山市顺德区巴德富实业有限公司 | Fluorine-containing acrylate emulsion and preparation method thereof |
| WO2016176389A1 (en) | 2015-04-30 | 2016-11-03 | The Chemours Company Tt, Llc | Crosslinkable fluorinated urethane additives for durable exterior coatings |
| WO2017081126A1 (en) | 2015-11-11 | 2017-05-18 | Solvay Specialty Polymers Italy S.P.A. | Novel hydroxy-terminated (per)fluoropolyether-urethane polymers and their use in clear-coat compositions |
| CN109929066A (en) * | 2017-12-15 | 2019-06-25 | 上海飞凯光电材料股份有限公司 | A kind of UV-cured resin, preparation method, coating |
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-
1995
- 1995-10-16 US US08/543,721 patent/US5597874A/en not_active Expired - Lifetime
-
1996
- 1996-10-11 JP JP51588497A patent/JP4074340B2/en not_active Expired - Fee Related
- 1996-10-11 WO PCT/US1996/016289 patent/WO1997014733A1/en active IP Right Grant
- 1996-10-11 AU AU74392/96A patent/AU706335B2/en not_active Ceased
- 1996-10-11 EP EP96936367A patent/EP0856021B1/en not_active Expired - Lifetime
- 1996-10-11 CA CA002234421A patent/CA2234421C/en not_active Expired - Fee Related
- 1996-10-11 DE DE69603195T patent/DE69603195T2/en not_active Expired - Fee Related
- 1996-10-11 BR BR9611102A patent/BR9611102A/en not_active IP Right Cessation
- 1996-10-11 NZ NZ321114A patent/NZ321114A/en unknown
- 1996-10-28 US US08/698,983 patent/US5705276A/en not_active Expired - Fee Related
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