Patent US4463154A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4463154A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyurethane powder enamels free of cleavage products as well as enamel coatings produced from such powders

Assignee: Evonik Operations GmbH
•
Filing: 1983-01-25
•
Granted: 1984-07-31
•
Expires: 2003-01-25
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract A polyurethane powder enamel free of volatile cleavage products comprising an adduct of the uretidinedione dimer of isophorone diisocyanate with a diol, wherein the adduct has the formula ##STR1## wherein R= ##STR2## X=NCO or ##STR3## R"=a divalent aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical or a diol, n>1, and R'=a monoalcohol radical or primary or secondary monoamine radical with 1-30 C-atoms, wherein the NCO/OH ratio of the dimer to the diol is from 1:0.5 to 1:0.9, the dimer/diol molar ratio is from 2:1 to 6:5, the average molecular weight is between 550 and 4300, and the melting point is ≧70° C. and ≦130° C., and wherein the uretidinedione groups present in the adduct are cleavable with heat into ≧98% --NCO groups, and a polyol having an OH functionality ≧3.4 to ≦7, an average molecular weight of 2000 to 5000, an OH number between 30 and 100 mg KOH/g, a viscosity of <100,000 mpa.s at 160° C., and a melting point ≧70° C. and ≦120° C., and wherein the mole ratio of the adduct to the polyol is chosen so that the ratio of NCO groups in the adduct to OH groups in the polyol is from 0.8:1 to 1.2:1.

Inventors

  • 👤 Josef Disteldorf
  • 👤 Rainer Gras
  • 👤 Horst Schnurbusch
  • 👤 Werner Hubel
  • 👤 Elmar Wolf

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 10:30
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/80; C08G18/8003; C08G18/8006; C08G18/8009; C08G18/8012; C08G18/77; C08G18/78; C08G18/79; C08G18/798; C08G18/8061; C08G2150/00; C08G2150/20

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 297 words
A process for preparing polyurethane powder enamles free of cleavage products selected from monoalcohols, primary or secondary amines, having good storage stability, which are curable above 120° C., and which are linear polyisocyanate addition products which are irreversibly, partially or completely, blocked and which contain uretidinedione groups, characterized in that, a. linear isophorone diisocyanate-diol polyaddition adducts which are irreversibly, partially or completely, blocked with terminal monoalcohols or monoamines and which contain uretidinedione groups, whose uretidinedione groups are essentially free from isocyanurate groups and are derived from isophorone diisocyanate which can be more than 98% decomposed back into isophorone diisocyanate by heating, having the following formula: ##STR7## wherein R= ##STR8## X= ##STR9## R'=a divalent aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical of a diol, n>1, R"=a monoalcohol radical or primary or secondary monoamine radical having 1-30 C-atoms, having an NCO/OH ratio or uretidinedione dimer of isophorone diisocyanate to diol of 1:0.5 to 1:0.9, preferably 1:0.6 to 1:0.8, a uretidinedione/diol molar ratio between 2:1 and 6:5, preferably 3:2 to 5:4, a molecular weight between 550 and 4300, preferably between 1500 and 2000, and a melting point of ≧70° C. to ≦130° C., preferably 80° C. to 120° C., b. polyhydroxy compounds having an OH functionality of ≧3.4 to ≦7, preferably 3.7 to 4.5, an average molecular weight of 2000 to 5000, preferably 2500 to 4500, a hydroxyl number between 30 and 100 mg KOH/g, preferably between 40 and 80 mg KOH/g, a viscosity of <100,000 mPa s preferably <40,000 mPa s at 160° C. and a melting point of ≦70° C. to ≦120° C., preferably 75° C. to 100° C., and c. the additives customary in polyurethane chemistry, are reacted, wherein the molar ratio of a. and b. is selected so that the NCO/OH ratio is 0.8:1 to 1.2:1.
Claim 2
Dependent Claim 297 words
A process for preparing polyurethane powder enamles free of cleavage products selected from monoalcohols, primary or secondary amines, having good storage stability, which are curable above 120° C., and which are linear polyisocyanate addition products which are irreversibly, partially or completely, blocked and which contain uretidinedione groups, characterized in that, a. linear isophorone diisocyanate-diol polyaddition adducts which are irreversibly, partially or completely, blocked with terminal monoalcohols or monoamines and which contain uretidinedione groups, whose uretidinedione groups are essentially free from isocyanurate groups and are derived from isophorone diisocyanate which can be more than 98% decomposed back into isophorone diisocyanate by heating, having the following formula: ##STR7## wherein R= ##STR8## X= ##STR9## R'=a divalent aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical of a diol, n>1, R"=a monoalcohol radical or primary or secondary monoamine radical having 1-30 C-atoms, having an NCO/OH ratio or uretidinedione dimer of isophorone diisocyanate to diol of 1:0.5 to 1:0.9, preferably 1:0.6 to 1:0.8, a uretidinedione/diol molar ratio between 2:1 and 6:5, preferably 3:2 to 5:4, a molecular weight between 550 and 4300, preferably between 1500 and 2000, and a melting point of ≧70° C. to ≦130° C., preferably 80° C. to 120° C., b. polyhydroxy compounds having an OH functionality of ≧3.4 to ≦7, preferably 3.7 to 4.5, an average molecular weight of 2000 to 5000, preferably 2500 to 4500, a hydroxyl number between 30 and 100 mg KOH/g, preferably between 40 and 80 mg KOH/g, a viscosity of <100,000 mPa s preferably <40,000 mPa s at 160° C. and a melting point of ≦70° C. to ≦120° C., preferably 75° C. to 100° C., and c. the additives customary in polyurethane chemistry, are reacted, wherein the molar ratio of a. and b. is selected so that the NCO/OH ratio is 0.8:1 to 1.2:1.
Claim 3
Dependent Claim 8 words
Polyurethane powder enamels prepared according to claim 1.
Claim 4
Dependent Claim 224 words
A polyurethane powder enamel free of volatile cleaverage products selected from monoalcohols or primary or secondary amines comprising: a. a partially or completely blocked adduct of the uretidinedione dimer of isophorone diisocyanate, essentially free from isocyanurate groups, with a diol, wherein said adduct has the formula: ##STR10## wherein R= ##STR11## X=NCO or ##STR12## R'=a divalent aliphatic cycloaliphatic, aromatic or araliphatic hydrocarbon radical of a diol, n>1, and R"-a monoalcohol radical or primary or secondary monoamine radical with 1-30 C-atoms, the NCO/OH ratio of said dimer to said diol is from 1:0.5 to 1:0.9, the dimer-diol molar ratio is from 2:1 to 6:5, the average molecular weight is between 550 and 4300, and the melting point is ≧70° C. and ≦130° C., and wherein the uretidinedione groups present in said adduct are cleavable with heat into ≧98% --NCO groups, and b. a polyol having an OH functionality >3.4 to <7, an average molecular weight of 2000 to 5000, an OH number between 30 and 100 mg KOH/g, a viscosity of <100,000 mPa s at 160° C., and a melting point ≧70° C. and ≦120° C., c. the additives customary in polyurethane chemistry, wherein the mole ratio of said adduct to said polyol is chosen so that the ratio of NCO groups in said adduct to OH groups in said polyol is from 0.8:1 to 1.2:1.
Claim 5
Dependent Claim 224 words
A polyurethane powder enamel free of volatile cleaverage products selected from monoalcohols or primary or secondary amines comprising: a. a partially or completely blocked adduct of the uretidinedione dimer of isophorone diisocyanate, essentially free from isocyanurate groups, with a diol, wherein said adduct has the formula: ##STR10## wherein R= ##STR11## X=NCO or ##STR12## R'=a divalent aliphatic cycloaliphatic, aromatic or araliphatic hydrocarbon radical of a diol, n>1, and R"-a monoalcohol radical or primary or secondary monoamine radical with 1-30 C-atoms, the NCO/OH ratio of said dimer to said diol is from 1:0.5 to 1:0.9, the dimer-diol molar ratio is from 2:1 to 6:5, the average molecular weight is between 550 and 4300, and the melting point is ≧70° C. and ≦130° C., and wherein the uretidinedione groups present in said adduct are cleavable with heat into ≧98% --NCO groups, and b. a polyol having an OH functionality >3.4 to <7, an average molecular weight of 2000 to 5000, an OH number between 30 and 100 mg KOH/g, a viscosity of <100,000 mPa s at 160° C., and a melting point ≧70° C. and ≦120° C., c. the additives customary in polyurethane chemistry, wherein the mole ratio of said adduct to said polyol is chosen so that the ratio of NCO groups in said adduct to OH groups in said polyol is from 0.8:1 to 1.2:1.
Claim 6
Dependent Claim 21 words
The powder enamel of claim 3, wherein the NCO/OH ratio of said dimer to said diol is from 1:0.6 to 1:0.8.
Claim 7
Dependent Claim 16 words
The powder enamel of claim 3, wherein the dimer/diol molar ratio is ferom 3:2 to 5:4.
Claim 8
Dependent Claim 20 words
The powder enamel of claim 3, wherein the melting point of said adduct is from 85° C. to 120° C.
Claim 9
Dependent Claim 18 words
The powder enamel of claim 3, wherein the OH functionality of said polyol is from 3.7 to 4.5.
Claim 10
Dependent Claim 19 words
The powder enamel of claim 3, wherein the average molecular weight of said polyol is from 2500 to 4500.
Claim 11
Dependent Claim 17 words
The powder enamel of claim 3, wherein said OH number is between 40 and 80 mg KOH/g.
Claim 12
Dependent Claim 15 words
The powder enamel of claim 3, wherein said viscosity is <40,000 mPas.s at 160° C.
Claim 13
Dependent Claim 20 words
The powder enamel of claim 3, wherein the melting point of said polyol is from 75° C. to 100° C.
Claim 14
Dependent Claim 18 words
The powder enamel of claim 3, wherein said powder enamel additionally comprises an additive common to polyurethane chemistry.
Claim 15
Dependent Claim 20 words
The powder enamel of claim 3, wherein said additive is a pigment, a spreading agent, a softener, or a catalyst.
Claim 16
Dependent Claim 12 words
A polyurethane enamel coating produced from the powder enamel of claim 3.

References Cited (Backward Citations)

US3998794A Cited
DE2420475A1 Cited
DE2502934A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-07-31 1988-01-30 1988-07-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-07-31 1992-01-30 1992-07-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-07-31 1996-01-30 1996-07-31 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag