Accelerators for two step adhesive systems
View Patent ↗Benzoylthiourea or benzoylthiourethane derivatives as cure accelerators in primers for two step adhesive systems are provided.
1. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, to a desired substrate surface,
applying a composition comprising a (meth)acrylate component and an oxidant to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.
2. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying a composition comprising a (meth)acrylate component and an oxidant to a desired substrate surface,
applying a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.
3. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying an oxidant to a desired substrate surface,
applying a composition comprising a (meth)acrylate component and a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2 to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.
4. A process for preparing a reaction product from a curable composition, comprising the steps of:
applying a composition comprising a (meth)acrylate component and a benzoyl thiourea or benzoyl thiourethane compound within structure I or IA
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring;
wherein X is optional, but when X is present, X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, to a desired substrate surface,
applying an oxidant to that desired substrate surface,
mating a second surface to that substrate surface to form an assembly, and
exposing the assembly to appropriate conditions for a time sufficient to cure the composition.
5. A primer composition comprising a cure accelerator within structures I or IA
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring; X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2, or
wherein R and R′ are independently selected from hydrogen, alkyl, alkenyl, aryl, hydroxyalkyl, hydroxyalkenyl, alkylene (meth)acrylate, carbonyl, carboxyl, or sulfonato, or R and R′ taken together form a carbocyclic or hetero atom-containing ring, or R′ is a direct bond attaching to the phenyl ring; X is halogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, hydroxyalkenyl, alkoxy, amino, alkylene- or alkenylene-ether, alkylene (meth)acrylate, carbonyl, carboxyl, nitroso, sulfonate, hydroxyl or haloalkyl; and Y is —SO 2 NH—, —CONH—, —NH—, and —PO(NHCONHCSNH 2 )NH—; and n is 0 or 1 and m is 1 or 2.
6. A reaction product prepared from the process of claim 1 .
7. A reaction product prepared from the process of claim 2 .
8. A reaction product prepared from the process of claim 3 .
9. A reaction product prepared from the process of claim 4 .
10. The process of claim 1 , wherein the oxidant is selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-butyl hydroperoxide, t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butyl cumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, and combinations thereof.
11. The process of claim 2 , wherein the oxidant is selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-butyl hydroperoxide, t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butyl cumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, and combinations thereof.
12. The process of claim 3 , wherein the oxidant is selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-butyl hydroperoxide, t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butyl cumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, and combinations thereof.
13. The process of claim 4 , wherein the oxidant is selected from the group consisting of cumene hydroperoxide, para-menthane hydroperoxide, t-amyl hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-butyl hydroperoxide, t-butyl perbenzoate, benzoyl peroxide, dibenzoyl peroxide, 1,3-bis(t-butylperoxyisopropyl)benzene, diacetyl peroxide, butyl 4,4-bis(t-butylperoxy)valerate, p-chlorobenzoyl peroxide, t-butyl cumyl peroxide, t-butyl perbenzoate, di-t-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne, 4-methyl-2,2-di-t-butylperoxypentane, and combinations thereof.
14. The process of claim 1 , wherein the (meth)acrylate component is within the general structure H 2 C═CGCO 2 R 1 , wherein G may be hydrogen or alkyl groups having from 1 to about 4 carbon atoms, and R 1 may be a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl, and aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.
15. The process of claim 2 , wherein the (meth)acrylate component is within the general structure H 2 C═CGCO 2 R 1 , wherein G may be hydrogen or alkyl groups having from 1 to about 4 carbon atoms, and R 1 may be a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl, and aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.
16. The process of claim 3 , wherein the (meth)acrylate component is within the general structure H 2 C═CGCO 2 R 1 , wherein G may be hydrogen or alkyl groups having from 1 to about 4 carbon atoms, and R 1 may be a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl, and aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.
17. The process of claim 4 , wherein the (meth)acrylate component is within the general structure H 2 C═CGCO 2 R 1 , wherein G may be hydrogen or alkyl groups having from 1 to about 4 carbon atoms, and R 1 may be a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl, and aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.