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US4598131A Expired / Lapsed US ⏱️ 0.0 years remaining

Catalysts for curable coating vehicle based upon aminoalkyloxy silanes and organic isocyanates

Assignee: PPG Industries Inc
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Filing: 1984-12-19
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Granted: 1986-07-01
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Expires: 2004-12-19
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Abstract

Abstract Disclosed is a composition containing a novel ungelled resin in combination with an effective amount of a cure-promoting catalyst selected from the group consisting of triflic acid (i.e., trifluoromethane sulfonic acid), a neutralization product of triflic acid with ammonia, a neutralization product of triflic acid with an amine, a tetraalkyl ammonium salt of triflic acid, and mixtures of one or more of the aforesaid catalysts. The composition can be cured with moisture and/or with polyols and can be used to provide protective and/or decorative films on a variety of substrates. The novel ungelled resin comprises a compound corresponding to a specified formula (I) which compound typically is prepared by reaction of an aminoalkyloxy silane with an organic isocyanate. The ungelled resin contains a hydrolyzable group that is attached directly to silicon.

Inventors

  • 👤 Paul J. Prucnal

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 12:44
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/08; C08G18/10

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 259 words
A composition comprising: (A) an ungelled resin containing a compound corresponding to the formula, ##STR16## wherein Q represents the residue of an organic isocyanate having an average isocyanate functionality of at least 1, R 1 independently represents H, a C 1 to C 10 alkyl radical, a C 1 -C 10 hydroxyalkyl radical or a radical corresponding to the formula ##STR17## wherein Z represents H or C 1 to C 4 alkyl, and W represents ##STR18## in which R 8 represents C 1 to C 8 alkyl, X represents a divalent radical containing at least 2 carbon atoms, A represents a monovalent silicon-containing group corresponding to the formula ##STR19## wherein R 2 independently represents hydrogen, a C 1 to C 10 alkyl group, a C 4 to C 10 cycloalkyl group, a C 6 to C 10 aryl group, or a monovalent aminoalkyl group, that is attached directly to Si, Y represents a hydrolyzable group that is attached directly to Si m is an integer ranging from 1 to 5, e is a positive integer wherein 1≦e≦11, d is zero or a positive integer wherein 0≦d≦10, and 3≦d+e≦11, and wherein x is a positive number which is equal to or less than the average isocyanate functionality of said organic isocyanate; and (B) an effective amount of a cure-accelerating catalyst selected from the group consisting of trifluoromethane sulfonic acid, a neutralization product of trifluoromethane sulfonic acid with ammonia, a neutralization product of trifluoromethane sulfonic acid with an amine, a tetraalkyl ammonium salt of trifluoromethane sulfonic acid, and a mixture thereof.
Claim 2
Dependent Claim 259 words
A composition comprising: (A) an ungelled resin containing a compound corresponding to the formula, ##STR16## wherein Q represents the residue of an organic isocyanate having an average isocyanate functionality of at least 1, R 1 independently represents H, a C 1 to C 10 alkyl radical, a C 1 -C 10 hydroxyalkyl radical or a radical corresponding to the formula ##STR17## wherein Z represents H or C 1 to C 4 alkyl, and W represents ##STR18## in which R 8 represents C 1 to C 8 alkyl, X represents a divalent radical containing at least 2 carbon atoms, A represents a monovalent silicon-containing group corresponding to the formula ##STR19## wherein R 2 independently represents hydrogen, a C 1 to C 10 alkyl group, a C 4 to C 10 cycloalkyl group, a C 6 to C 10 aryl group, or a monovalent aminoalkyl group, that is attached directly to Si, Y represents a hydrolyzable group that is attached directly to Si m is an integer ranging from 1 to 5, e is a positive integer wherein 1≦e≦11, d is zero or a positive integer wherein 0≦d≦10, and 3≦d+e≦11, and wherein x is a positive number which is equal to or less than the average isocyanate functionality of said organic isocyanate; and (B) an effective amount of a cure-accelerating catalyst selected from the group consisting of trifluoromethane sulfonic acid, a neutralization product of trifluoromethane sulfonic acid with ammonia, a neutralization product of trifluoromethane sulfonic acid with an amine, a tetraalkyl ammonium salt of trifluoromethane sulfonic acid, and a mixture thereof.
Claim 3
Dependent Claim 98 words
The composition of claim 1 wherein said hydrolyzable group Y is selected from the group consisting of ##STR20## and the C 2 to C 3 residue of a 1,2- or 1,3-glycol, wherein R 3 represents C 1 -C 7 alkyl, C 6 -C 8 cycloalkyl, C 6 -C 8 aryl, or C 3 -C 8 alkoxyalkyl, R 4 represents H or C 1 -C 4 alkyl, R 5 and R 6 independently represent C 1 -C 4 alkyl, C 6 -C 8 cycloalkyl, or C 6 -C 8 aryl, and R 7 represents C 4 -C 7 alkylene.
Claim 4
Dependent Claim 37 words
The composition of claim 2 wherein Q represents the residue from an isocyanate-functional polyisocyanate which is a reaction product of an organic polyisocyanate and a polyol having an average molecular weight ranging from 62 to about 3,000.
Claim 5
Dependent Claim 24 words
The composition of claim 3 wherein said polyol comprises a polyester polyol having an average molecular weight ranging from about 170 to about 2,000.
Claim 6
Dependent Claim 10 words
The composition of claim 1 additionally comprising an epoxy resin.
Claim 7
Dependent Claim 13 words
The composition of claim 5 wherein said epoxy resin contains an aliphatic diepoxide.
Claim 8
Dependent Claim 18 words
The composition of claim 3 wherein said polyol comprises a polyol containing at least one carboxylic acid group.
Claim 9
Dependent Claim 19 words
The composition of claim 5 wherein said cure-accelerating catalyst is a neutralization product of triflic acid with an amine.
Claim 10
Dependent Claim 17 words
The composition of claim 5 wherein said cure-accelerating catalyst is a tetraalkyl ammonium salt of triflic acid.
Claim 11
Dependent Claim 57 words
The composition of claim 5 wherein Q represents the residue from an isocyanate-functional polyisocyanate prepolymer which is a reaction product of an organic polyisocyanate and a polyol, which polyol has an average molecular weight ranging from 62 to about 3,000; R 1 represents hydrogen; A represents a monovalent silicon-containing group from an organosilicate and d equals zero.
Claim 12
Dependent Claim 18 words
The composition of claim 10 wherein said polyol comprises a polyol containing at least one carboxylic acid group.
Claim 13
Dependent Claim 266 words
A two-pack composition, a first pack comprising an ungelled resin containing a compound according to the formula, ##STR21## wherein Q represents the residue of an organic isocyanate having an average isocyanate functionality of at least 1, R 1 independently represents H or a C 1 to C 10 alkyl radical, a C 1 -C 10 hydroxyalkyl radical or a radical corresponding to the formula ##STR22## wherein Z represents H or C 1 to C 4 alkyl, and W represents ##STR23## in which R 8 represents C 1 to C 8 alkyl, X represents a divalent radical containing at least 2 carbon atoms, A represents a monovalent silicon-containing group corresponding to the formula ##STR24## wherein R 2 independently represents hydrogen, a C 1 to C 10 alkyl group, a C 4 to C 10 cycloalkyl group, a C 6 to C 10 aryl group, or a monovalent aminoalkyl group, that is attached directly to Si, Y represents a hydrolyzable group that is attached directly to Si m is an integer ranging from 1 to 5, e is a positive integer wherein 1≦e≦11, d is zero or a positive integer wherein 0≦d≦10, and 3≦d+e≦11, and wherein x is a positive number which is equal to or less than the average isocyanate functionality of said organic isocyanate; and a second pack comprising an effective amount of a cure-accelerating catalyst selected from the group consisting of trifluoromethane sulfonic acid, a neutralization product of trifluoromethane sulfonic acid with ammonia, a neutralization product of trifluoromethane sulfonic acid with an amine, a tetraalkyl ammonium salt of trifluoromethane sulfonic acid, and a mixture thereof.
Claim 14
Dependent Claim 266 words
A two-pack composition, a first pack comprising an ungelled resin containing a compound according to the formula, ##STR21## wherein Q represents the residue of an organic isocyanate having an average isocyanate functionality of at least 1, R 1 independently represents H or a C 1 to C 10 alkyl radical, a C 1 -C 10 hydroxyalkyl radical or a radical corresponding to the formula ##STR22## wherein Z represents H or C 1 to C 4 alkyl, and W represents ##STR23## in which R 8 represents C 1 to C 8 alkyl, X represents a divalent radical containing at least 2 carbon atoms, A represents a monovalent silicon-containing group corresponding to the formula ##STR24## wherein R 2 independently represents hydrogen, a C 1 to C 10 alkyl group, a C 4 to C 10 cycloalkyl group, a C 6 to C 10 aryl group, or a monovalent aminoalkyl group, that is attached directly to Si, Y represents a hydrolyzable group that is attached directly to Si m is an integer ranging from 1 to 5, e is a positive integer wherein 1≦e≦11, d is zero or a positive integer wherein 0≦d≦10, and 3≦d+e≦11, and wherein x is a positive number which is equal to or less than the average isocyanate functionality of said organic isocyanate; and a second pack comprising an effective amount of a cure-accelerating catalyst selected from the group consisting of trifluoromethane sulfonic acid, a neutralization product of trifluoromethane sulfonic acid with ammonia, a neutralization product of trifluoromethane sulfonic acid with an amine, a tetraalkyl ammonium salt of trifluoromethane sulfonic acid, and a mixture thereof.
Claim 15
Dependent Claim 16 words
The two pack composition of claim 12 additionally comprising an epoxy resin in said first pack.
Claim 16
Dependent Claim 15 words
The two pack composition of claim 13 wherein said epoxy resin contains an aliphatic diepoxide.
Claim 17
Dependent Claim 21 words
The two pack composition of claim 12 wherein said cure-accelerating catalyst is a neutralization product of triflic acid with an amine.
Claim 18
Dependent Claim 19 words
The two pack composition of claim 12 wherein said cure-accelerating catalyst is a tetraalkyl ammonium salt of triflic acid.
Claim 19
Dependent Claim 62 words
The two pack composition of claim 13 where for said resin, Q represents the residue from an isocyanate-functional polyisocyanate which is a reaction product of an organic polyisocyanate and a polyol, which polyol has an average molecular weight ranging from 62 to about 3,000; R 1 represents hydrogen; and A represents a monovalent silicon-containing group from an organosilicate and d equals zero.
Claim 20
Dependent Claim 20 words
The two pack composition of claim 17 wherein said polyol comprises a polyol containing at least one carboxylic acid group.
Claim 21
Dependent Claim 31 words
The composition of claim 1 wherein X represents a divalent radical containing at least 2 carbon atoms containing one or more groups selected from ether, amino, amido, carbamate, urea, and thio.
Claim 22
Dependent Claim 32 words
The two-pack composition of claim 12 wherein X represents a divalent radical containing at least 2 carbon atoms containing one or more groups selected from ether, amino, amido, carbamate, urea, and thio.

References Cited (Backward Citations)

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US3426057A Cited
US3345194A Cited
US3453122A Cited
US3726907A Cited
US3895043A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-06-30 1989-12-30 1990-07-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-06-30 1993-12-30 1994-07-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-06-30 1997-12-30 1998-07-01 $7700.00 Window Closed / Lapsed

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