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US4382798A Expired / Lapsed US ⏱️ 0.0 years remaining

Anti-soiling treating agent

Assignee: DIC Corp
•
Filing: 1981-08-10
•
Granted: 1983-05-10
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Expires: 2001-08-10
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Abstract

Abstract An anti-soiling treating agent comprising (a) a perfluoroalkyl-containing hybrid urethane compound (I) resulting from the addition reaction of two perfluoroalkyl-containing alcohols which have a difference in melting point of at least 20 DEG C. and are selected from compounds of the following formula Rf-A-B-OH wherein Rf represents a linear or branched perfluoroalkyl group, A is the group -CH2-l in which l is an integer of 0 to 5, the group <IMAGE> in which R is a hydrogen atom, an alkyl group having not more than 12 carbon atoms or a substituted alkyl group, the group <IMAGE> in which R is as defined above, a phenylene group, an ether linkage, or an ester linkage, and B represents an alkylene or aralkylene group having not more than 12 carbon atoms, or a derivative thereof containing an ether linkage, the mole ratio between the two alcohols being 33-67:67-33, with a polyisocyanate, or (b) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I) and a fluorine-free vinyl polymer (II) having a Rockwell hardness of 90 to 130, or (c) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I) and a perfluoroalkyl-containing vinyl polymer (III), or (d) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I), the perfluoroalkyl-containing vinyl polymer (III) and the fluorine-free vinyl polymer (II), and if desired, water and/or an organic solvent.

Inventors

  • 👤 Yasuyuki Suzuki
  • 👤 Tadashi Ito

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 23:16
CPC Classifications
C; C14; C14C; C14C11/00; C14C11/003; C14C11/006; D; D06; D06M; D06M13/00; D06M13/322; D06M13/402; D06M13/425; D06M13/428; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31558; Y10T428/31591; Y10T428/31605

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 604 words
An anti-soiling treating agent having a solids content of 0.001 to 70% comprising (a) a perfluoroalkyl-containing hybrid urethane compound (I) resulting from the addition reaction of two perfluoroalkyl-containing alcohols which have a difference in melting point of at least 20° C. and are selected from compounds of the following formula Rf--A--B--OH wherein Rf represents a linear or branched perfluoroalkyl group, A is the group --CH 2 -- l in which l is an integer of 0 to 5, the group ##STR12## in which R is a hydrogen atom, an alkyl group having not more than 12 carbon atoms or a substituted alkyl group, the group ##STR13## in which R is as defined above, a phenylene group, an ether linkage, or an ester linkage, and B represents an alkylene or aralkylene group having not more than 12 carbon atoms, or a derivative thereof containing an ether linkage, the mole ratio between the two alcohols being 33-67:67-33, with a polyisocyanate, said addition reaction being carried out at a temperature of 50° to 150° C. in the presence or absence of an orgainic solvent in an anhydrous condition while maintaining the equivalent ratio of the alcohol to the isocyanate at from 1:1.2 to 1.2:1, or (b) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I) and a fluorine-free vinyl polymer (II) having a Rockwell hardness of 90 to 130, the weight ratio of (I) to (II) being in the range of from 1:10 to 10:1, or (c) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I) and a perfluoroalkyl-containing vinyl polymer (III), said perfluoroalkyl-containing vinyl polymer (III) being represented by the general formula ##STR14## wherein Rf, A and B are as defined above, X represents a divalent bonding group such as ##STR15## R 1 and R 2 represent a hydrogen atom or an alkyl group having not more than 2 carbon atoms, R 3 represents Rf--A--B-- or an alkyl group having not more than 8 carbon atoms, and p is a number of 5 to 100 which shows the number of recurring monomeric units, or being represented by the general formula ##STR16## wherein Rf, A, B, X, and R 3 are as defined above, R 4 , R 5 and R 6 each represents a hydrogen atom, an alkyl group having not more than 8 carbon atoms, or a halogen atom other than fluorine, Y represents a divalent bonding group such as an ester, ether or an acid amide group or a direct bond between R 7 and a carbon atom in the main chain, R 7 represents a hydrogen atom, a halogen atom other than fluorine, a nitrile group, or an alkyl, alkenyl or aryl group having not more than 20 carbon atoms, and m and n independently represent a number of 5 to 100 which shows the number of recurring monomeric units, provided that m and n are selected such that the ratio of the two monomers to be copolymerized is in the range of from 3:97 to 90:10, wherein the weight ratio of the hybrid urethane compound (I) to the perfluoroalkyl-containing vinyl polymer (III) is in the range of from 1:10 to 10:1 or (d) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I), the perfluoroalkyl-containing vinyl polymer (III) and the fluorine-free vinyl polymer (II), wherein the weight ratio of the hybrid urethane compound (I) to the perfluoroalkyl-containing vinyl polymer (III) is in the range of from 1:10 to 10:1, and the weight ratio of the sum of (I) and (III) to the fluorine-free vinyl polymer (II) is in the range of from 1:10 to 10:1, and if desired, water and/or an organic solvent.
Claim 2
Dependent Claim 604 words
An anti-soiling treating agent having a solids content of 0.001 to 70% comprising (a) a perfluoroalkyl-containing hybrid urethane compound (I) resulting from the addition reaction of two perfluoroalkyl-containing alcohols which have a difference in melting point of at least 20° C. and are selected from compounds of the following formula Rf--A--B--OH wherein Rf represents a linear or branched perfluoroalkyl group, A is the group --CH 2 -- l in which l is an integer of 0 to 5, the group ##STR12## in which R is a hydrogen atom, an alkyl group having not more than 12 carbon atoms or a substituted alkyl group, the group ##STR13## in which R is as defined above, a phenylene group, an ether linkage, or an ester linkage, and B represents an alkylene or aralkylene group having not more than 12 carbon atoms, or a derivative thereof containing an ether linkage, the mole ratio between the two alcohols being 33-67:67-33, with a polyisocyanate, said addition reaction being carried out at a temperature of 50° to 150° C. in the presence or absence of an orgainic solvent in an anhydrous condition while maintaining the equivalent ratio of the alcohol to the isocyanate at from 1:1.2 to 1.2:1, or (b) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I) and a fluorine-free vinyl polymer (II) having a Rockwell hardness of 90 to 130, the weight ratio of (I) to (II) being in the range of from 1:10 to 10:1, or (c) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I) and a perfluoroalkyl-containing vinyl polymer (III), said perfluoroalkyl-containing vinyl polymer (III) being represented by the general formula ##STR14## wherein Rf, A and B are as defined above, X represents a divalent bonding group such as ##STR15## R 1 and R 2 represent a hydrogen atom or an alkyl group having not more than 2 carbon atoms, R 3 represents Rf--A--B-- or an alkyl group having not more than 8 carbon atoms, and p is a number of 5 to 100 which shows the number of recurring monomeric units, or being represented by the general formula ##STR16## wherein Rf, A, B, X, and R 3 are as defined above, R 4 , R 5 and R 6 each represents a hydrogen atom, an alkyl group having not more than 8 carbon atoms, or a halogen atom other than fluorine, Y represents a divalent bonding group such as an ester, ether or an acid amide group or a direct bond between R 7 and a carbon atom in the main chain, R 7 represents a hydrogen atom, a halogen atom other than fluorine, a nitrile group, or an alkyl, alkenyl or aryl group having not more than 20 carbon atoms, and m and n independently represent a number of 5 to 100 which shows the number of recurring monomeric units, provided that m and n are selected such that the ratio of the two monomers to be copolymerized is in the range of from 3:97 to 90:10, wherein the weight ratio of the hybrid urethane compound (I) to the perfluoroalkyl-containing vinyl polymer (III) is in the range of from 1:10 to 10:1 or (d) a composition comprising the perfluoroalkyl-containing hybrid urethane compound (I), the perfluoroalkyl-containing vinyl polymer (III) and the fluorine-free vinyl polymer (II), wherein the weight ratio of the hybrid urethane compound (I) to the perfluoroalkyl-containing vinyl polymer (III) is in the range of from 1:10 to 10:1, and the weight ratio of the sum of (I) and (III) to the fluorine-free vinyl polymer (II) is in the range of from 1:10 to 10:1, and if desired, water and/or an organic solvent.
Claim 3
Dependent Claim 19 words
The treating agent of claim 1 wherein the perfluoroalkyl group represented by Rf has 4 to 16 carbon atoms.
Claim 4
Dependent Claim 41 words
The treating agent of claim 1 wherein one of the perfluoroalkyl-containing alcohols has a melting point of at least 70° C., and the other has a melting point at least 20° C. lower than the melting point of the first-mentioned alcohol.
Claim 5
Dependent Claim 21 words
The treating agent of claim 1 wherein the hybrid urethane compound (I) has a melting point of 20° to 150° C.
Claim 6
Dependent Claim 31 words
The treating agent of claim 1 wherein the weight ratio of the hybrid urethane compound (I) to the fluorine-free vinyl polymer (II) is in the range of from 1:5 to 5:1.
Claim 7
Dependent Claim 19 words
The treating agent of claim 1 wherein the anti-soiling treating agent comprises (a) the perfluoroalkyl-containing hybrid urethane compound (I).
Claim 8
Dependent Claim 25 words
The treating agent of claim 1 wherein the anti-soiling treating agent comprises (b) the perfluoroalkyl-containing hybrid urethane compound (I) and the fluorine-free vinyl polymer (II).
Claim 9
Dependent Claim 25 words
The treating agent of claim 1 wherein the anti-soiling treating agent comprises (c) the perfluoroalkyl-containing hybrid urethane compound (I) and the perfluoroalkyl-containing vinyl polymer (III).
Claim 10
Dependent Claim 31 words
The treating agent of claim 8 wherein the weight ratio of the hybrid urethane compound (I) to the perfluoroalkyl-containing vinyl polymer (III) is in the range of from 1:5 to 5:1.
Claim 11
Dependent Claim 18 words
The treating agent of claim 8 wherein the perfluoroalkyl-containing vinyl polymer (III) is a polymer of formula (III-1).
Claim 12
Dependent Claim 18 words
The treating agent of claim 8 wherein the perfluoroalkyl-containing vinyl polymer (III) is a polymer of formula (III-2).
Claim 13
Dependent Claim 30 words
The treating agent of claim 1 wherein the anti-soiling treating agent comprises (d) the perfluoroalkyl-containing hybrid urethane compound (I), the fluorine-free vinyl polymer (II) and the perfluoroalkyl-containing vinyl polymer (III).
Claim 14
Dependent Claim 20 words
The treating agent of claim 1 wherein the two perfluoroalkyl-containing alcohols are compounds selected from the group consisting of: ##STR17##
Claim 15
Dependent Claim 28 words
The treating agent of claim 8 or claim 12 wherein the perfluoroalkyl-containing vinyl polymer (III) is a polymer of a monomer selected from the group consisting of: ##STR18##
Claim 16
Dependent Claim 57 words
The treating agent of claim 12 wherein the weight ratio of the hybrid urethane compound (I) to the perfluoroalkyl-containing vinyl polymer (III) is in the range of from 1:5 to 5:1, and the weight ratio of the sum of (I) and (III) and the fluorine-free vinyl polymer (II) is in the range of from 1:5 to 5:1.
Claim 17
Dependent Claim 20 words
The treating agent of claim 1 wherein the polyisocyanate is an aromatic polyisocyanate, an alicyclic polyisocyanate or an aliphatic polyisocyanate.
Claim 18
Dependent Claim 22 words
The treating agent of claim 7 or 12 wherein the fluorine-free vinyl polymer (II) has a Rockwell hardness of 100 to 120.
Claim 19
Dependent Claim 22 words
The treating agent of claim 7 or 12 wherein the fluorine-free vinyl polymer (II) is polystyrene, hard polyvinyl chloride, or poly(methyl methacrylate).
Claim 20
Dependent Claim 11 words
A textile article treated with the treating agent of claim 1.
Claim 21
Dependent Claim 11 words
A paper product treated with the treating agent of claim 1.
Claim 22
Dependent Claim 11 words
A plastic article treated with the treating agent of claim 1.
Claim 23
Dependent Claim 11 words
A leather article treated with the treating agent of claim 1.
Claim 24
Dependent Claim 11 words
A metallic article treated with the treating agent of claim 1.

References Cited (Backward Citations)

US3940435A Cited
US3920389A Cited
US3965074A Cited
US3968066A Cited
US4060681A Cited
US4264484A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-05-09 1986-11-08 1987-05-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-05-09 1990-11-08 1991-05-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-05-09 1994-11-08 1995-05-10 $7700.00 Window Closed / Lapsed

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