CA2482489A1 - Repellent fluorochemical compositions - Google Patents

Repellent fluorochemical compositions Download PDF

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Publication number
CA2482489A1
CA2482489A1 CA 2482489 CA2482489A CA2482489A1 CA 2482489 A1 CA2482489 A1 CA 2482489A1 CA 2482489 CA2482489 CA 2482489 CA 2482489 A CA2482489 A CA 2482489A CA 2482489 A1 CA2482489 A1 CA 2482489A1
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CA
Canada
Prior art keywords
composition
group
fluorochemical
aliphatic
monofunctional compound
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.)
Granted
Application number
CA 2482489
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French (fr)
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CA2482489C (en
Inventor
Malcolm B. Burleigh
David P. Cheatham
John C. Clark
A. Dale Otteson
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3M Innovative Properties Co
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Individual
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Publication of CA2482489A1 publication Critical patent/CA2482489A1/en
Application granted granted Critical
Publication of CA2482489C publication Critical patent/CA2482489C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/186—Monomers containing fluorine with non-fluorinated comonomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/27—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of alkylpolyalkylene glycol esters of unsaturated carboxylic acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties
    • 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

This invention provides compositions for treating fibrous substrates to rend er those substrates durably repellent to water and oil and durably resistant to dry soil comprising a 1) fluorochemical urethane formed by reacting a tri- o r higher order isocyanate with a fluorochemical monofunctional compound and optionally a non-fluorinated aliphatic monofunctional compound; and 2) a fluorochemical polymeric surfactant. The present invention also provides a method of treating fibrous substrates to render those substrates durably repellent to water and oil and durably resistant to dry soil comprising application of the aforementioned composition to a fibrous substrate with optionally one or more stainblocker compounds such as acrylic and methacryli c acid polymers and copolymers, sulfonated phenol-formaldehyde resins, and styrene-maleic anhydride polymers and copolymers, said application of the composition taking place either coincident with or following application of the hydrophilic anti-staining compound or compounds to the substrate. Fibrou s substrates treated according to this method and fibrous substrates treated with the aforementioned compositions are also disclosed.

Claims (15)

1. A fluorochemical treatment composition comprising 1) a fluorochemical urethane comprising the reaction product of:
a. an aliphatic polyisocyanate having three or more isocyanate groups;
and b. a fluorochemical monofunctional compound of the formula R f -Q'-Z;
wherein R f a perfluoroalkyl or perfluoroheteroalkyl group, Q' is an organic linking group, and Z is an isocyanate-reactive functional group, and said fluorochemical is in an amount sufficient to react with at least about 50% of the available isocyanate groups; and
2) a fluoroalkyl (meth)acrylate/polyoxyalkylene (meth)acrylate copolymer.

2. The composition of claim 1 wherein said Z group is selected from -NH2, -SH, -OH, -NCO, NR1H, and said R f group has from 3 to 5 carbon atoms.
3. The composition of claim 1 wherein said fluorochemical monofunctional compound is selected from the group consisting of:

CF3(CF2)3SO2N(CH3)CH2CH2OH, ~CF3(CF2)3SO2N(CH3)CH(CH3)CH2OH, CF3(CF2)3SO2N(CH3)CH2CH(CH3)NH2,~CF3(CF2)3SO2N(CH2CH3)CH2CH2SH, CF3(CF2)3SO2N(CH3)CH2CH2SCH2CH2OH,~C6F13SO2N(CH3)(CH2)4OH, CF3(CF2)5SO2N(H)(CH2)3OH, ~C3F7SO2N(CH3)CH2CH2OH, CF3(CF2)4SO2N(CH3)(CH2)4NH2, ~C4F9SO2N(CH3)(CH2)3OH, CF3(CF2)5SO2N(CH2CH3)CH2CH2OH, ~CF3(CF2)5SO2N(C2H5)(CH2)4OH, CF3(CF2)3SO2N(C3H7)CH2OCH2CH2CH2OH, CF3(CF2)2SO2N(C2H5)(CH2)4OH, CF3(CF2)4SO2N(CH2CH2CH3)CH2CH2OH, CF3(CF2)4SO2N(CH2CH2CH3)CH2CH2NCH3H, CF3(CF2)3SO2N(C4H9)CH2CH2NH2, and CF3(CF2)3SO2N(C4H9)(CH2)4SH.
4. The composition of claim 1 wherein said fluorochemical urethane comprises the reaction product of an aliphatic monofunctional compound.
5. The composition of claim 4 wherein said aliphatic monofunctional compound is of the formula R'''-Z, wherein R''',is an aliphatic group and Z is an isocyanate-reactive functional group.
6. The composition of claim 5 wherein said aliphatic monofunctional compound comprises at least one unbranched, aliphatic alcohol having from 12 to about 72 carbon atoms.
7. The composition of claim 5 comprising a fluorochemical urethane of the formula (R f*)n A(NHCO-Z'R''')m-n, wherein R f* is R f -Q'-Z', Z' is the residue of Z, A is the residue of said aliphatic isocyanate, having valency m, R''' is an aliphatic group, and n (average) is at least 1.5.
8. The composition of claim 1 wherein R f a fluoroalkyl group having from 3 to about 5 carbon atoms, Q' is -SO2N(R1)R2-, R1 is a -H or -CH3, R2 is an alkylene group having 1 to 3 carbon atoms, and Z is -OH.
9. The composition of claim 4 wherein the aliphatic monofunctional compound is in an amount sufficient to react with the remaining available isocyanate groups.
10. The composition of claim 4 wherein said aliphatic monofunctional compound is in an amount sufficient to react with 33% or less of the available isocyanate groups.
11. The composition of claim 4 wherein the aliphatic monofunctional compound is in an amount sufficient to react with 15% of less of the available isocyanate groups.
12. The composition of claim 1 wherein the fluorochemical monofunctional compound is in an amount sufficient to react with 75% or more of the available isocyanate groups.
13. The composition of claim 1 further comprising a hydrophilic anti-staining compound.
14. The composition of claim 1 wherein said (meth)acrylate copolymer comprises interpolymerized units of fluoroalkyl (meth)acrylate monomer units and poly(oxyalkylene) (meth)acrylate monomer units of the formula:

wherein R1f a fluoroalkyl group, R3 is H or a C1 to C4 alkyl group, R4 is an alkylene group having 2 to 4 carbon atoms, Q is an organic linking group and x is an integer of at least 5.
15. The composition of claim 14 wherein said R1f group has 3 to 5 carbon atoms.

17. The copolymer of claim 11 further comprising interpolymerized monomer units of acrylic ester or acrylamides bearing a water-solubilizing group.

18. The copolymer of claim 11 wherein said monomer units are of the formula wherein R3 is H or C1 to C4 alkyl group;
n' is an integer of 1 to 10, and M is hydrogen, a metal cation, or a tertiary amine.

19. The treatment composition of claim 1 further comprising a solvent.

20. The treatment composition of claim 16 comprising at least 65 wt.% water.

21. The treatment composition of claim 11 comprising from about 20 to about 99.5 weight percent of the above described fluorochemical urethane compounds, and 0.5 to 80 weight percent of said fluorochemical polymeric surfactants.

22. The composition of claim 1, further comprising a hydrocarbon surfactant.

23. The treatment composition of claim 1, further comprising a polycarboxylic acid stainblocker and wherein the pH of said treatment composition is from 5 to 11.

24. A method for imparting stain-release characteristics to a fibrous substrate comprising the steps of:
(a) applying a treatment composition of claim 1, and (b) allowing the treatment composition to cure.

25. The method of claim 21 wherein said treatment composition is applied in an amount sufficient to provide between 0.05% and 3% solids on fiber.

25. An article comprising:
a fibrous substrate having a cured coating derived from at least one solvent and a chemical composition of claim 1.
CA2482489A 2002-04-17 2003-02-18 Repellent fluorochemical compositions Expired - Fee Related CA2482489C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/124,523 2002-04-17
US10/124,523 US7078454B2 (en) 2002-04-17 2002-04-17 Repellent fluorochemical compositions
PCT/US2003/004933 WO2003089712A1 (en) 2002-04-17 2003-02-18 Repellent fluorochemical compositions

Publications (2)

Publication Number Publication Date
CA2482489A1 true CA2482489A1 (en) 2003-10-30
CA2482489C CA2482489C (en) 2012-07-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2482489A Expired - Fee Related CA2482489C (en) 2002-04-17 2003-02-18 Repellent fluorochemical compositions

Country Status (10)

Country Link
US (1) US7078454B2 (en)
EP (1) EP1495182B1 (en)
JP (1) JP4537073B2 (en)
KR (1) KR20050000517A (en)
CN (1) CN100408751C (en)
AT (1) ATE406475T1 (en)
AU (1) AU2003213124B2 (en)
CA (1) CA2482489C (en)
DE (1) DE60323216D1 (en)
WO (1) WO2003089712A1 (en)

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EP1495182B1 (en) 2008-08-27
WO2003089712A1 (en) 2003-10-30
KR20050000517A (en) 2005-01-05
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AU2003213124B2 (en) 2009-01-08
AU2003213124A1 (en) 2003-11-03
JP4537073B2 (en) 2010-09-01
ATE406475T1 (en) 2008-09-15
US7078454B2 (en) 2006-07-18
CN100408751C (en) 2008-08-06
US20030204015A1 (en) 2003-10-30
WO2003089712A8 (en) 2005-03-17
CA2482489C (en) 2012-07-10

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