← Back to Patent Explorer
US4622369A Expired / Lapsed US ⏱️ 0.0 years remaining

Urethane resins containing hydrolyzable moieties from organosilane compounds

Assignee: PPG Industries Inc
•
Filing: 1985-04-30
•
Granted: 1986-11-11
•
Expires: 2005-04-30
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Disclosed is an ungelled urethane resin composition containing a urethane compound having in a molecule thereof at least one group containing a silicon atom selected from: ##STR1## wherein Q represents the residue from a urethane polyol; each R which may be the same or different, represents hydrogen or a C 1 -C 10 group joined to Si through an Si-C linkage; and Y represents an easily hydrolyzable group. The urethane resin composition contains an amount of easily hydrolyzable Y moieties such that the ratio of the number of grams of the ungelled urethane resin composition to equivalents of easily hydrolyzable Y moieties in the ungelled urethane resin composition is in a range of from 40 to 667. Preferred urethane resin compositions can be cured in the presence of atmospheric moisture and a suitable catalyst at a temperature of less than or equal to 121 degrees Celsius within 3 hours. Disclosed is a method for producing the ungelled urethane resin composition. Also disclosed is a nonaqueous composition, particularly a nonaqueous coating composition, containing an ungelled urethane resin composition. Preferred coating compositions containing an ungelled urethane resin composition can be cured in the presence of atmospheric moisture and a suitable catalyst at a temperature of less than or equal to 121 degrees Celsius.

Inventors

  • 👤 Wen H. Chang
  • 👤 David T. McKeough
  • 👤 Ronald R. Ambrose

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 15:25
CPC Classifications
C; C08; C08L; C08L75/00; C08L75/04; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/837

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 118 words
An ungelled urethane resin composition comprising a urethane compound having at least one group containing a silicon atom said group selected from: ##STR18## wherein Q represents the residue from a urethane polyol, and each R independently is selected from the group of moieties consisting of hydrogen and a C 1 -C 1O group joined to Si through an Si--C linkage, and Y represents an easily hydrolyzable group; provided that said urethane resin composition contains an amount of easily hydrolyzable Y moieties such that the ratio of the number of grams of said ungelled urethane resin composition to equivalents of easily hydrolyzable Y moieties in said ungelled urethane resin composition is in a range of from 40 to 667.
Claim 2
Dependent Claim 118 words
An ungelled urethane resin composition comprising a urethane compound having at least one group containing a silicon atom said group selected from: ##STR18## wherein Q represents the residue from a urethane polyol, and each R independently is selected from the group of moieties consisting of hydrogen and a C 1 -C 1O group joined to Si through an Si--C linkage, and Y represents an easily hydrolyzable group; provided that said urethane resin composition contains an amount of easily hydrolyzable Y moieties such that the ratio of the number of grams of said ungelled urethane resin composition to equivalents of easily hydrolyzable Y moieties in said ungelled urethane resin composition is in a range of from 40 to 667.
Claim 3
Dependent Claim 40 words
The ungelled urethane resin composition of claim 1 which is curable to a tack free state in the presence of atmospheric moisture and a catalyst at a temperature of less than or equal to 121 degrees C. within 3 hours.
Claim 4
Dependent Claim 35 words
The ungelled urethane resin composition of claim 1 which is curable to a tack free state in the presence of atmospheric moisture and a catalyst at a temperature of 24 degrees C. within 24 hours.
Claim 5
Dependent Claim 92 words
The ungelled urethane resin composition of claim 1 wherein at least a portion of the R moieties independently represent a C 1 -C 10 group, joined to Si through an Si--C linkage, containing a primary amino group, a secondary amino group, a tertiary amino group, a polyamino group, a mercapto group, a urea group, a cyclic urea group, a urethane group, a 1,2-epoxy group, an ester group, an ether group, a thioether group, an amido group, an imidazolinyl group, a cyano group, an allyl group, a vinyl group, or a halo atom.
Claim 6
Dependent Claim 87 words
The ungelled urethane resin composition of claim 1 wherein each Y independently is selected from the group consisting of --OR 1 , ##STR19## and the monohydroxy or cyclic C 2 -C 3 residue of a 1,2- or 1,3-glycol, wherein R 1 represents a C 1 -C 3 alkyl R 2 independently represents H or C 1 -C 4 alkyl, R 3 and R 4 independently represent H, C 1 -C 4 alkyl, or C 6 -C 8 aryl, and R 5 represents C 4 -C 7 alkylene.
Claim 7
Dependent Claim 29 words
The ungelled urethane resin composition of claim 1 wherein at least one Y is a methoxy group and at least one R is a C 1 -C 3 group.
Claim 8
Dependent Claim 23 words
The urethane resin composition of claim 6 wherein R is selected from the group consisting of a methyl group and a vinyl group.
Claim 9
Dependent Claim 77 words
The ungelled urethane resin composition of claim 1 wherein said urethane polymer is a reaction product of said urethane polyol and an organosilicon-containing material comprising at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula R--Si(OR 6 ) 3 wherein R independently represents hydrogen or a C 1 -C 1O group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 10
Dependent Claim 71 words
The ungelled urethane resin composition of claim 1 which is a reaction product of a urethane polyol and an organosilicon-containing material comprising at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula ##STR20## wherein R independently represents hydrogen or a C 1 -C 1O group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 11
Dependent Claim 71 words
The ungelled urethane resin composition of claim 1 which is a reaction product of a urethane polyol and an organosilicon-containing material comprising at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula ##STR21## wherein R independently represents hydrogen or a C 1 -C 1O group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 12
Dependent Claim 96 words
The ungelled urethane resin composition of claim 1 which is a reaction product of a urethane polyol and an organosilicon-containing material comprising a mixture containing at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula R--Si(OR 6 ) 3 and at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula ##STR22## wherein R independently represents hydrogen or a C 1 -C 1O group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 13
Dependent Claim 64 words
The ungelled urethane resin composition of claim 1 which is a reaction product of a urethane polyol and a partial hydrolysis product of a compound corresponding to the formula R--Si(OR 6 ) 3 wherein R independently represents hydrogen or a C 1 -C 1O group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 14
Dependent Claim 29 words
The ungelled urethane resin composition of claim 11 wherein at least one OR 6 is a methoxy group and at least one R is selected from methyl or vinyl.
Claim 15
Dependent Claim 32 words
The ungelled urethane resin composition of claim 11 wherein said urethane polyol has a weight average molecular weight determined by gel permeation chromatography using a polystyrene standard of from 200 to 50,000.
Claim 16
Dependent Claim 22 words
The ungelled urethane resin composition of claim 11 wherein said urethane polyol has a hydroxyl equivalent weight of from 74 to 1,000.
Claim 17
Dependent Claim 122 words
A nonaqueous composition comprising: an ungelled urethane resin composition containing a urethane compound having at least one group containing a silicon atom said group selected from: ##STR23## wherein Q represents the residue from a urethane polyol, and each R independently is selected from the group of moieties consisting of hydrogen and a C 1 -C 1O group joined to Si through an Si--C linkage, and Y represents an easily hydrolyzable group; provided that the urethane resin composition contains an amount of easily hydrolyzable Y moieties such that the ratio of the number of grams of said ungelled urethane resin composition to equivalents of easily hydrolyzable Y moieties in said ungelled urethane resin composition is in a range of from 40 to 667.
Claim 18
Dependent Claim 122 words
A nonaqueous composition comprising: an ungelled urethane resin composition containing a urethane compound having at least one group containing a silicon atom said group selected from: ##STR23## wherein Q represents the residue from a urethane polyol, and each R independently is selected from the group of moieties consisting of hydrogen and a C 1 -C 1O group joined to Si through an Si--C linkage, and Y represents an easily hydrolyzable group; provided that the urethane resin composition contains an amount of easily hydrolyzable Y moieties such that the ratio of the number of grams of said ungelled urethane resin composition to equivalents of easily hydrolyzable Y moieties in said ungelled urethane resin composition is in a range of from 40 to 667.
Claim 19
Dependent Claim 33 words
The nonaqueous composition of claim 16 which is curable in the presence of atmospheric moisture and a catalyst at a temperature of less than or equal to 121 degrees C. within 3 hours.
Claim 20
Dependent Claim 28 words
The nonaqueous composition of claim 16 which is curable in the presence of atmospheric moisture and a catalyst at a temperature of 24 degrees C. within 24 hours.
Claim 21
Dependent Claim 90 words
The nonaqueous composition of claim 16 wherein at least a portion of the R moieties independently represent a C 1 -C 1O group, joined to Si through an Si--C linkage, containing a primary amino group, a secondary amino group, a tertiary amino group, a polyamino group, a mercapto group, a urea group, a cyclic urea group, a urethane group, a 1,2-epoxy group, an ester group, an ether group, a thioether group, an amido group, an imidazolinyl group, a cyano group, an allyl group, a vinyl group, or a halo atom.
Claim 22
Dependent Claim 91 words
The nonaqueous composition of claim 16 wherein each easily hydrolyzable group Y of said urethane compound independently is selected from the group consisting of --OR 1 , ##STR24## and the monohydroxy or cyclic C 2 -C 3 residue of a 1,2- or 1,3-glycol, wherein R 1 represents a C 1 -C 3 alkyl R 2 represents H or C 1 -C 4 alkyl, R 3 and R 4 independently represent H, C 1 -C 4 alkyl, or C 6 -C 8 aryl, and R 5 represents C 4 -C 7 alkylene.
Claim 23
Dependent Claim 24 words
The nonaqueous composition of claim 16 wherein at least one Y is a methoxy group and at least one R is methyl or vinyl.
Claim 24
Dependent Claim 99 words
The nonaqueous composition of claim 16 wherein said ungelled urethane resin composition is a reaction product of a urethane polyol and an organosilicon-containing material comprising a mixture containing at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula R--Si(OR 6 ) 3 and at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula ##STR25## wherein R independently represents hydrogen or a C 1 -C 10 group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 25
Dependent Claim 14 words
A substrate having thereon a cured film comprising the nonaqueous composition of claim 16.
Claim 26
Dependent Claim 14 words
A substrate having thereof a cured film comprising the nonaqueous composition of claim 17.
Claim 27
Independent Claim 97 words
A method of preparing an ungelled urethane resin composition, curable in the presence of atmospheric moisture and a catalyst at a temperature of less than or equal to 121 degrees C. by reacting components comprising: (A) a urethane polyol; and (B) an organosilicon-containing material comprising at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula R--Si(OR 6 ) 3 wherein R independently represents hydrogen or a C 1 -C 10 group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 28
Independent Claim 97 words
A method of preparing an ungelled urethane resin composition, curable in the presence of atmospheric moisture and a catalyst at a temperature of less than or equal to 121 degrees C. by reacting components comprising: (A) a urethane polyol; and (B) an organosilicon-containing material comprising at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula R--Si(OR 6 ) 3 wherein R independently represents hydrogen or a C 1 -C 10 group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 29
Dependent Claim 60 words
The method of claim 25 wherein said organosilicon-containing material additionally comprises at least 10 percent by weight of said organosilicon-containing material of a compound corresponding to the formula ##STR26## wherein R independently represents hydrogen or a C 1 -C 10 group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 30
Dependent Claim 56 words
The method of claim 25 wherein said organosilicon-containing material is a partial hydrolysis product of a compound corresponding to the formula R--Si(OR 6 ) 3 wherein R independently represents hydrogen or a C 1 -C 10 group joined to Si through an Si--C linkage, and R 6 independently represents a C 1 -C 3 alkyl group.
Claim 31
Dependent Claim 25 words
The nonaqueous coating composition of claim 16 additionally comprising an organic polyol wherein said ungelled urethane resin is a curing agent for said organic polyol.
Claim 32
Dependent Claim 43 words
The nonaqueous composition of claim 28 wherein said organic polyol is selected from the group consisting of: simple diols, triols and higher hydric alcohols; acrylic polyols; polyurethane polyols; polyester polyols, polyether polyols; amide-containing polyols; polyhydroxyl-functional epoxy resins; polyhyric polyvinyl alcohols; and mixtures thereof.

References Cited (Backward Citations)

US4093673A Cited
US4113665A Cited
US4191713A Cited
US4243767A Cited
US4368294A Cited
US4399261A Cited
US4472465A Cited
JPS59126470A Cited
US4446292A Cited
US4467081A Cited
US4501872A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-11-10 1990-05-12 1990-11-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-11-10 1994-05-12 1994-11-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-11-10 1998-05-12 1998-11-11 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag