Low odor reactive methacrylate composition for fast room temperature curing floor coating formulations
A UV or thermally curable, low odor, liquid coating composition, which readily applied at room temperature without heating comprising: a) a reactive acrylic based polymer comprising pendant acrylate or methacrylate groups; b) reactive unsaturated monomers, typically acrylic or methacrylic monomers, often polyfunctional monomers; c) a thermal or UV activated radical initiator; and in many embodiments, d) an inert and non-polar wax or viscous oil, e.g., a paraffinic material, and e) optionally a tertiary amine, for example, a tertiary amine accelerator used with a thermally activated radical initiator. Also provided are substrates coated with the composition of the invention, for example, flooring coated with the inventive composition.
1. A liquid coating composition comprising
a) from 10 to 40 wt %, based on the weight of components a) through e), of an acrylic based polymer comprising acrylate or methacrylate pendant groups prepared by reacting glycidyl acrylate and/or glycidyl methacrylate with a co-polymer prepared from a mixture of monomers comprising at least one acrylic and/or methacrylic acid monomer and one or more monomers of formula Ia and/or IIa,
wherein R, R′ and R″ are independently selected from methyl and hydrogen;
G is C 1-18 , straight or branched chain saturated alkyl; C 2-12 , straight or branched chain unsaturated alkyl; said alkyl or unsaturated alkyl substituted by OH, OR, NR 2 and/or interrupted by one or more carbonyl, carboxylate, O or NR; C 3-12 epoxyalkyl; phenyl; phenyl substituted by alkyl, alkoxy or amino; benzyl; benzyl substituted by alkyl, alkoxy or amino; phenethyl; phenethyl substituted by alkyl, alkoxy or amino alcohol;
n is 2 or 3, and
Z is straight or branched chain C 2-12 alkyl or C 2-12 alkyl substituted by OH, OR, or NR 2 and/or interrupted by one or more carbonyl, carboxylate, O or NR, e.g., C 4-24 alkyl or C 4-24 alkyl substituted by OH, OR, NR 2 and/or interrupted by one or more carbonyl, carboxylate, O or NR;
b) from 50 to 89 wt % of one or more reactive monomers having a boiling point at 1 atmosphere of greater than 100° C. wherein at least 50 mole % of the reactive monomers are selected from the group consisting of compounds of formula I
R′R″C═C(R)COOY Formula I
and compounds comprising two or more reactive groups of formula II,
R′R″C═C(R)COO—, Formula II:
wherein R, R′ and R″ are each individually selected from H, C 1-12 alkyl, C 1-6 alkyl substituted by phenyl, C 1-6 alkyl substituted by phenyl substituted by one or more C 1-4 alkyl, phenyl, and phenyl substituted by one or more C 1-4 alkyl, and
Y is selected from H, C 1-18 , straight or branched chain saturated alkyl; C 2-12 , straight or branched chain unsaturated alkyl; said alkyl or unsaturated alkyl substituted by OH, OR, NR 2 and/or interrupted by one or more carbonyl, carboxylate, O or NR; C 3-12 epoxyalkyl; phenyl; phenyl substituted by alkyl, alkoxy or amino; benzyl; benzyl substituted by alkyl, alkoxy or amino; phenethyl; phenethyl substituted by alkyl, alkoxy or amino alcohol
c) 0.1 to 10 wt % of a thermally activated or UV activated radical initiator,
d) 0 to 10 wt % of a non-polar, inert wax or oil, and
e) 0 to 5 wt % of a tertiary amine,
wherein the coating composition has a viscosity of 50,000 cps or less at 25° C.
2. The coating composition according to claim 1 wherein at least 50 mole % of the monomer mixture is made up of acrylic and/or methacrylic esters and acids.
3. The coating composition according to claim 2 , wherein 60 wt % or more of the monomers of formula Ia and IIa are monomers of formula Ia.
4. The coating composition according to claim 3 , wherein 80 wt % or more of the monomers of formula Ia and IIa are monomers of formula Ia.
5. The coating composition according to claim 1 , wherein in Formula Ia G is C 1-6 straight or branched chain saturated alkyl; C 2-6 straight or branched chain unsaturated alkyl; said alkyl or unsaturated alkyl substituted by OH, NR 2 and/or interrupted by one or more O or NR; or C 3-12 epoxyalkyl.
6. The coating composition according to claim 1 wherein the compounds of formula I and the compounds comprising two or moieties of formula II of component b), R, R′ and R″ are each individually selected from H and methyl and Y is selected from C 6-12 alkyl, and C 2-6 alkyl substituted by OR, NRR′, or oxirane.
7. The coating composition according to claim 6 wherein in the compounds of formula I and the compounds comprising two or moieties of formula IIII, R and R′ are H.
8. The coating composition according to claim 1 wherein the wax or oil is a paraffin wax.
9. The coating composition according to claim 1 wherein component b) comprises at least one compound of formula I and at least one compound comprising two or more reactive groups of formula II.
10. The liquid coating composition according to claim 1 comprising
a) from 10 to 40 wt %, based on the weight of components a) through e), of an acrylic based polymer comprising acrylate or methacrylate pendant groups prepared by reacting glycidyl acrylate and/or glycidyl methacrylate with a co-polymer prepared from a mixture of monomers comprising at least one acrylic and/or methacrylic acid monomer and one or more monomers of formula Ia and/or IIa,
wherein R, R′ and R″ are independently selected from methyl and hydrogen;
G is C 1-12 straight or branched chain saturated alkyl; C 2-12 straight or branched chain unsaturated alkyl; C 2-12 said alkyl or unsaturated alkyl substituted by OH, NR 2 and/or interrupted by one or more O or NR; C 3-12 epoxyalkyl; phenyl; phenyl substituted by alkyl, alkoxy or amino; benzyl;
benzyl substituted by alkyl, alkoxy or amino; phenethyl; phenethyl substituted by alkyl, alkoxy or amino alcohol; and the like; n is 2 or 3; and
Z is straight or branched chain C 2-12 alkyl, C 4-24 alkyl interrupted by one or more O or NR 2 ,
Wherein at least 90 mole % of the monomer mixture is made up of acrylic and/or methacrylic esters and acids;
b) from 50 to 89 wt % of one or more reactive monomers having a boiling point at 1 atmosphere of greater than 100° C. selected from the group consisting of compounds of formula I
R′R″C═C(R)COOY Formula I
and compounds comprising two or more reactive groups of formula II,
R′R″C═C(R)COO—, Formula II:
and
wherein R, R′ and R″ are each individually selected from H, C 1-12 alkyl, C 1-6 alkyl substituted by phenyl, C 1-6 alkyl substituted by phenyl substituted by one or more C 1-4 alkyl, phenyl, and phenyl substituted by one or more C 1-4 alkyl, and
Y is selected from H, C 1-12 alkyl, and C 1-6 alkyl substituted by phenyl, OR, NRR′, or oxirane;
c) 0.1 to 10 wt % of a thermally activated or UV activated radical initiator,
d) 0 to 5 wt % of a non-polar, inert wax or oil, and
e) 0 to 5 wt % of a tertiary amine,
wherein 60 wt % or more of the monomers of formula Ia and IIa are monomers of formula Ia and wherein the coating composition has a viscosity of less than 10,000 cps at 25° C.
11. The coating composition according to claim 1 comprising
a) 10 to 40 wt %, of the acrylic based polymer comprising acrylate or methacrylate pendant groups;
b) 50 to 89 wt % of the one or more reactive monomers having a boiling point at 1 atmosphere of greater than 100° C.
c) 0.1 to 10 wt %, of a thermally activated radical initiator,
d) 0.1 to 5 wt % of an inert wax or oil, and
e) 0.1 to 5 wt % of a tertiary amine.
12. A substrate coated with film obtained by curing the coating composition of claim 11 .
13. The coating composition according to claim 12 wherein the acrylic polymer comprising acrylate or methacrylate pendant groups has a molecular wt of less than Mn 1900.
14. A flooring material coated with a 5 to 60 micron film obtained by curing the coating composition of claim 11 .
15. The coating composition according to claim 1 comprising
a) 10 to 40 wt % of the acrylic polymer comprising acrylate or methacrylate pendant groups;
b) 50 to 89 wt % of the one or more reactive monomers having a boiling point at 1 atmosphere of greater than 100° C.
c) 0.1 to 10 wt %, of a UV activated radical initiator,
d) 0 to 5 wt % of an inert wax or oil, and
e) 0 to 5 wt % of a tertiary amine.
16. A substrate coated with a film obtained by curing the coating composition of claim 15 .
17. A flooring material coated with film obtained by curing the coating composition of claim 15 .
18. The coating composition according to claim 15 having a viscosity of 50-7,500 cps at 25° C.
19. The coating composition according to claim 1 wherein the acrylic polymer comprising acrylate or methacrylate pendant groups has a molecular wt of less than Mn 1900.
20. A process for coating a flooring material comprising apply a coating composition of claim 1 to a floor or material used in preparing a floor, and then allowing the coating to cure at room temperature or exposing the coating to UV radiation and allowing the coating to cure at room temperature.