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US 9,868,689 B2Granted
Anaerobic curable compositions containing blocked (meth)acrylate acid compounds
AssigneeHenkel IP & Holding GmbH
InventorsAndrew D. Messana, Sean M. Burdzy, Joel D. Schall, Anthony F. Jacobine
Life of this patent
Estimating the term…
Abstract
Anaerobic curable compositions, such as adhesives and sealants, containing blocked carboxylic acid compounds are provided. The blocked carboxylic acid compounds are labile carboxylic acid compounds having acetal linkages, which cleave to release the underlying carboxylic acid during anaerobic cure.
Claims10
An anaerobic curable composition comprising;
- (a) a (meth)acrylate component;
- (b) an anaerobic cure system;
- and
- (c) a compound of structure I
- [An(CO2R)q I
- wherein A is C1-12 alkyl or alkylene, C2-12 alkenyl or alkenylene, C5-14 cycloalkyl, C5-14 cycloalkenyl, C5-14 cycloalkylene, or C5-14 cycloalkenylene, or C6-14 aryl, each of which may be interrupted or substituted by one or more heteroatoms or heteroatom containing groups, respectively;
- R is an acetal residue derived from a vinyl ether compound selected from one or more of ethyl vinyl ether;
- isobutyl vinyl ether;
- n-butyl vinyl ether;
- tert-butyl vinyl ether;
- cyclohexyl vinyl ether;
- 1,4-cyclohexane dimethanol divinyl ether;
- butanediol divinyl ether;
- hydroxybutyl vinyl ether;
- diethylene glycol divinyl ether;
- triethylene glycol divinyl ether;
- dodecyl vinyl ether;
- octadecyl vinyl ether;
- 4-(hydroxy methyl) cyclohexyl methyl vinyl ether;
- 2-ethyl hexyl vinyl ether;
- diethylene glycol monovinyl ether;
- poly-THF 290-divinyl ether;
- 3-amino propyl vinyl ether;
- tert-amyl vinyl ether;
- diethylaminoethyl vinyl ether;
- ethyleneglycol butyl vinyl ether;
- ethyleneglycol divinyl ether;
- ethyleneglycol monovinyl ether;
- hexanediol divinyl ether;
- hexanediol monovinyl ether;
- isopropyl vinyl ether;
- polyethyleneglycol-520 methyl vinyl ether;
- pluriol-E200 divinyl ether;
- n-propyl vinyl ether;
- tetraethyleneglycol divinyl ether;
- triethyleneglycol methyl vinyl ether;
- and trimethylolpropane trivinyl ether;
- n is 0-5;
- and q is 1-5.
36 more elements
A composition comprising the reaction product of:
- (a) a (meth)acrylate component;
- (b) an anaerobic cure system;
- and
- (c) a compound of structure
- [An(CO2R)q I
- wherein A is C1-12 alkyl or alkylene, C2-12 alkenyl or alkenylene, C5-14 cycloalkyl, C5-14 cycloalkenyl, C5-14 cycloalkylene, or C5-14 cycloalkenylene, or C6-14 aryl, each of which may be interrupted or substituted by one or more heteroatoms or heteroatom containing groups, respectively;
- R is an acetal residue derived from a vinyl ether compound selected from one or more of ethyl vinyl ether;
- isobutyl vinyl ether;
- n-butyl vinyl ether;
- tert-butyl vinyl ether;
- cyclohexyl vinyl ether;
- 1,4-cyclohexane dimethanol divinyl ether;
- butanediol divinyl ether;
- hydroxybutyl vinyl ether;
- diethylene glycol divinyl ether;
- triethylene glycol divinyl ether;
- dodecyl vinyl ether;
- octadecyl vinyl ether;
- 4-(hydroxy methyl) cyclohexyl methyl vinyl ether;
- 2-ethyl hexyl vinyl ether;
- diethylene glycol monovinyl ether;
- poly-TEF 290-divinyl ether;
- 3-amino propyl vinyl ether;
- tert-amyl vinyl ether;
- diethylaminoethyl vinyl ether;
- ethyleneglycol butyl vinyl ether;
- ethyleneglycol divinyl ether;
- ethyleneglycol monovinyl ether;
- hexanediol divinyl ether;
- hexanediol monovinyl ether;
- isopropyl vinyl ether;
- polyethyleneglycol-520 methyl vinyl ether;
- pluriol-E200 divinyl ether;
- n-propyl vinyl ether;
- tetraethyleneglycol divinyl ether;
- triethyleneglycol methyl vinyl ether;
- and trimethylolpropane trivinyl ether;
- n is 0-5;
- and q is 1-5.
36 more elements
A method of making an anaerobic curable composition comprising;
- (i) Providing a composition comprising:
- (a) a (meth)acrylate component;
- and
- (b) an anaerobic cure system;
- and
- (ii) Adding to the composition of step (i) a compound of structure I
- [An(CO2R)q I
- wherein A is C1-12 alkyl or alkylene, C2-12 alkenyl or alkenylene, C5-14 cycloalkyl, C5-14 cycloalkenyl, C5-14 cycloalkylene, or C5-14 cycloalkenylene, or C6-14 aryl, each of which may be interrupted or substituted by one or more heteroatoms or heteroatom containing groups, respectively, as the case may be;
- R is an acetal residue derived from a vinyl ether compound selected from one or more of ethyl vinyl ether;
- isobutyl vinyl ether;
- n-butyl vinyl ether;
- tert-butyl vinyl ether;
- cyclohexyl vinyl ether;
- 1,4-cyclohexane dimethanol divinyl ether;
- butanediol divinyl ether;
- hydroxybutyl vinyl ether;
- diethylene glycol divinyl ether;
- triethylene glycol divinyl ether;
- dodecyl vinyl ether;
- octadecyl vinyl ether;
- 4-(hydroxy methyl) cyclohexyl methyl vinyl ether;
- 2-ethyl hexyl vinyl ether;
- diethylene glycol monovinyl ether;
- poly-THF 290-divinyl ether;
- 3-amino propyl vinyl ether;
- tert-amyl vinyl ether;
- diethylaminoethyl vinyl ether;
- ethyleneglycol butyl vinyl ether;
- ethyleneglycol divinyl ether;
- ethyleneglycol monovinyl ether;
- hexanediol divinyl ether;
- hexanediol monovinyl ether;
- isopropyl vinyl ether;
- polyethyleneglycol-520 methyl vinyl ether;
- pluriol-E200 divinyl ether;
- n-propyl vinyl ether;
- tetraethyleneglycol divinyl ether;
- triethyleneglycol methyl vinyl ether;
- and trimethylolpropane trivinyl ether;
- n is 0-5;
- and q is 1-5.
38 more elements
Dependencies are inferred from the claim text.