US4540598A
Expired / Lapsed
US
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Process for curing acid-curable finishes
Assignee: BASF Corp
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Filing: 1984-08-09
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Granted: 1985-09-10
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Expires: 2004-08-09
Abstract
Abstract Oxime sulfonates of the formula I ##STR1## in which m is 0 or 1 and n is 1 or 2, R 1 and R 2 are monovalent radicals or, together with the atoms to which they are linked, form a ring system, and R 3 is the n-valent radical of a mono- or di-sulfonic acid, can be split photochemically to give the free sulfonic acid. They can therefore be used as latent acid catalysts for combined radiation curing and heat curing of acid-curable finishes.
Inventors
- 👤 Godwin Berner
- 👤 Werner Rutsch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:26
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/41; C08K5/42; C09; C09D; C09D161/00
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
321 words
A process for curing baking finishes which contain an acid-curable resin and, as a curing catalyst, a blocked sulfonic acid of the formula I ##STR21## in which m is 0 or 1 and n is 1 or 2, R 1 is C 1 -C 12 -alkyl, C 1 -C 4 -halogenoalkyl, C 2 -C 6 -alkenyl, C 5 -C 12 -cycloalkyl, C 6 -C 10 -aryl which is unsubstituted or mono- or poly-substituted by halogen, C 1 -C 16 -alkyl, C 1 -C 4 -alkoxy, phenoxy, phenyl or nitro, furyl, thienyl, C 7 -C 12 -aralkyl, C 1 -C 8 -alkoxy, C 5 -C 8 -cycloalkoxy, phenoxy or H 2 N--CO--NH--, R 2 is as defined for R 1 or is --CN, C 2 -C 5 -alkanoyl, benzoyl, C 2 -C 5 -alkoxycarbonyl, phenoxycarbonyl, --N(R 4 )(R 5 ), morpholino or piperidino, or R 1 and R 2 , together with the atoms to which they are linked, form a 5-membered to 8-membered ring to which 1 to 2 benzo radicals can be fused, R 4 being hydrogen, C 1 -C 12 -alkyl, phenyl, C 2 -C 9 -alkanoyl or benzoyl and R 5 being hydrogen, C 1 -C 12 -alkyl or cyclohexyl, and R 3 , with n=1, is C 1 -C 18 -alkyl, C 6 -C 10 -aryl which is unsubstituted or mono- or poly-substituted by halogen, C 1 -C 4 -halogenoalkyl, C 1 -C 16 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl-CONH-, phenyl-CONH-, benzoyl or nitro, C 5 -C 12 -cycloalkyl, C 7 -C 9 -aralkyl, camphoryl, --CF 3 , --CCl 3 or --NH 2 , and, with n=2, R 3 is C 2 -C 12 -alkylene, or unsubstituted or C 1 -C 12 -alkyl-substituted phenylene, naphthylene, diphenylene or oxydiphenylene, which comprises irradiating the finish with short-wave light, whereby the free sulfonic acid is formed, and then fully curing it at an elevated temperature.
Claim 2
Dependent Claim
321 words
A process for curing baking finishes which contain an acid-curable resin and, as a curing catalyst, a blocked sulfonic acid of the formula I ##STR21## in which m is 0 or 1 and n is 1 or 2, R 1 is C 1 -C 12 -alkyl, C 1 -C 4 -halogenoalkyl, C 2 -C 6 -alkenyl, C 5 -C 12 -cycloalkyl, C 6 -C 10 -aryl which is unsubstituted or mono- or poly-substituted by halogen, C 1 -C 16 -alkyl, C 1 -C 4 -alkoxy, phenoxy, phenyl or nitro, furyl, thienyl, C 7 -C 12 -aralkyl, C 1 -C 8 -alkoxy, C 5 -C 8 -cycloalkoxy, phenoxy or H 2 N--CO--NH--, R 2 is as defined for R 1 or is --CN, C 2 -C 5 -alkanoyl, benzoyl, C 2 -C 5 -alkoxycarbonyl, phenoxycarbonyl, --N(R 4 )(R 5 ), morpholino or piperidino, or R 1 and R 2 , together with the atoms to which they are linked, form a 5-membered to 8-membered ring to which 1 to 2 benzo radicals can be fused, R 4 being hydrogen, C 1 -C 12 -alkyl, phenyl, C 2 -C 9 -alkanoyl or benzoyl and R 5 being hydrogen, C 1 -C 12 -alkyl or cyclohexyl, and R 3 , with n=1, is C 1 -C 18 -alkyl, C 6 -C 10 -aryl which is unsubstituted or mono- or poly-substituted by halogen, C 1 -C 4 -halogenoalkyl, C 1 -C 16 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl-CONH-, phenyl-CONH-, benzoyl or nitro, C 5 -C 12 -cycloalkyl, C 7 -C 9 -aralkyl, camphoryl, --CF 3 , --CCl 3 or --NH 2 , and, with n=2, R 3 is C 2 -C 12 -alkylene, or unsubstituted or C 1 -C 12 -alkyl-substituted phenylene, naphthylene, diphenylene or oxydiphenylene, which comprises irradiating the finish with short-wave light, whereby the free sulfonic acid is formed, and then fully curing it at an elevated temperature.
Claim 3
Dependent Claim
223 words
A process according to claim 1, wherein the finish contains a curing catalyst of the formula I, in which m is 0 or 1, n is 1, R 1 is C 1 -C 12 -alkyl, C 1 -C 4 -halogenoalkyl, C 5 -C 12 -cycloalkyl, C 6 -C 10 -aryl which is unsubstituted or mono- or di-substituted by Cl, C 1 -C 16 -alkyl, C 1 -C 4 -alkoxy, phenoxy or nitro, 2-furyl, 2-thienyl, C 1 -C 4 -alkoxy, cyclohexyloxy or phenoxy, R 2 is as defined for R 1 or is --CN, C 2 -C 5 -alkanoyl, benzoyl, C 2 -C 5 -alkoxycarbonyl, --N(R 4 )(R 5 ) or morpholino, or R 1 and R 2 , together with the atoms to which they are linked, form a 5-membered to 8-membered ring to which 1 or 2 benzo radicals can be fused, R 4 being hydrogen, C 1 -C 4 -alkyl, phenyl, C 2 -C 5 -alkanoyl or benzoyl and R 5 being hydrogen or C 1 -C 4 -alkyl, and R 3 is C 1 -C 18 -alkyl, C 6 -C 10 -aryl which is unsubstituted or mono- or poly-substituted by halogen, C 1 -C 4 -halogenoalkyl, C 1 -C 16 -alkyl, C 1 -C 4 -alkoxy or nitro, C 5 -C 12 -cycloalkyl, camphoryl, --CF 3 or --CCl 3 .
Claim 4
Dependent Claim
144 words
A process according to claim 1, wherein the finish contains a curing catalyst of the formula I, in which m is 0 or 1, n is 1, R 1 is C 1 -C 4 -alkyl, trifluoromethyl, phenyl which is unsubstituted or mono- or di-substituted by Cl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or nitro, 2-furyl, 2-thienyl or C 1 -C 4 -alkoxy, R 2 is as defined for R 1 or is --CN, dialkylamino or morpholino, or R 1 and R 2 , together with the atoms to which they are linked, form a 5-membered or 6-membered ring to which 1 or 2 benzo radicals can be fused, and R 3 is C 1 -C 4 -alkyl, or phenyl which is unsubstituted or mono- or di-substituted by Cl, CF 3 , C 1 -C 16 -alkyl or NO 2 .
Claim 5
Dependent Claim
97 words
A process according to claim 1, wherein the finish contains a curing catalyst of the formula I, in which m is 0 or 1, n is 1, R 1 is C 1 -C 4 -alkyl, trifluoromethyl, phenyl, mono- or di-chlorophenyl or nitrophenyl, R 2 is as defined for R 1 or is --CN, or R 1 and R 2 , together with the atoms to which they are linked, form a 5-membered to 6-membered ring to which one or two benzo radicals are fused, and R 3 is methyl, phenyl or C 1 -C 16 -alkyl-substituted phenyl.
Claim 6
Dependent Claim
17 words
A process according to claim 1, wherein the finish contains an amino resin as the acid-curable resin.
Claim 7
Dependent Claim
23 words
A process according to claim 1, wherein the finish contains a mixture of a melamine resin with an acrylic, polyester or alkyd resin.
Claim 8
Dependent Claim
26 words
A process according to claim 1, wherein, after the irradiation, the finish is fully cured at a temperature below 1120° C., in particular at 80°-100° C.
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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) | 1988-09-09 | 1989-03-11 | 1989-09-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-09 | 1993-03-11 | 1993-09-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-09 | 1997-03-11 | 1997-09-10 | $7700.00 | Window Closed / Lapsed |