Redox-curing type nonaqueous curable composition

Abstract

The present invention relates to processes of making a cured dental adhesive compositions, in contact with a wetting material surface, by contacting the wetting material surface having water present on the surface with a nonaqueous composition including at least one liquid radical polymeric monomer (a), an organic peroxide (b), and a water-soluble reducing compound (c) in the form of a solid, where the water-soluble reducing compound (c) is dispersed in the liquid radical polymeric monomer (a); and solvating the water-soluble reducing compound (c) present at an interface between the redox-curing nonaqueous curable composition and the wetting material with the water present on the wetting material surface.

1 . A process of making a cured dental adhesive composition, in contact with a wetting material surface, comprising:
 contacting said wetting material surface having water present thereon with a nonaqueous composition comprising:
 at least one liquid radical polymeric monomer (a), 
 an organic peroxide (b), and 
 a water-soluble reducing compound (c) in the form of a solid,
 wherein said water-soluble reducing compound (c) is dispersed in said at least one liquid radical polymeric monomer (a); and 
 
   solvating said water-soluble reducing compound (c) present at an interface between said redox-curing nonaqueous curable composition and said wetting material with said water present on said wetting material surface.   
     
     
         2 . The process according to  claim 1 , wherein said water-soluble reducing compound (c) in the form of a solid is a sulfite powder. 
     
     
         3 . The process according to  claim 1 , wherein said organic peroxide (b) and said water-soluble reducing compound (c) in the form of a solid are present respectively in ratios of 0.05 through 10 parts by weight and 0.01 through 15 parts by weight based on 100 parts by weight of said liquid radical polymeric monomer (a). 
     
     
         4 . The process according to  claim 1 , further comprising first dividedly packing a first agent comprising said liquid radical polymeric monomer (a) and said organic peroxide (b) and a second agent comprising said liquid radical polymeric monomer (a) and said water-soluble reducing compound (c) in the form of a solid. 
     
     
         5 . The process according to  claim 4 , wherein said water-soluble reducing compound (c) in the form of a solid is a sulfite powder. 
     
     
         6 . The process according to  claim 4 , wherein
 said first agent comprises 0.1 through 50 parts by weight of said organic peroxide (b) based on 100 parts by weight of said liquid radical polymeric monomer (a),   said second agent comprises 0.1 through 50 parts by weight of said water-soluble reducing compound (c) in the form of a solid based on 100 parts by weight of said liquid radical polymeric monomer (a), and   said first agent and said second agent are dividedly packed in a weight ratio of 1:10 through 10:1.   
     
     
         7 . The process according to  claim 1 , wherein said organic peroxide is selected from the group consisting of benzoyl peroxide; 2,4-dichlorobenzoyl peroxide; m-toluoyl peroxide; t-butyl peroxybenzoate; bis-t-butyl peroxyisophthalate; 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane; t-butyl peroxy-2-ethyl hexanoate; t-butyl peroxyisopropyl carbonate; dicumyl peroxide; di-t-butyl peroxide; lauroyl peroxide; 1,1-bis(t-butyl peroxy)3,3,5-trimethyl cyclohexane; 1,1-bis(t-butyl peroxy)cyclohexane; 1,1-bis(t-hexyl peroxy)cyclohexane; methyl ethyl ketone peroxide; cyclohexanone peroxide; methyl acetoacetate peroxide; t-butyl hydroperoxide; cumene hydroperoxide; and p-diisopropyl benzene peroxide. 
     
     
         8 . The process according to  claim 4 , wherein said organic peroxide is selected from the group consisting of benzoyl peroxide; 2,4-dichlorobenzoyl peroxide; m-toluoyl peroxide; t-butyl peroxybenzoate; bis-t-butyl peroxyisophthalate; 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane; t-butyl peroxy-2-ethyl hexanoate; t-butyl peroxyisopropyl carbonate; dicumyl peroxide; di-t-butyl peroxide; lauroyl peroxide; 1,1-bis(t-butyl peroxy)3,3,5-trimethyl cyclohexane; 1,1-bis(t-butyl peroxy)cyclohexane; 1,1-bis(t-hexyl peroxy)cyclohexane; methyl ethyl ketone peroxide; cyclohexanone peroxide; methyl acetoacetate peroxide; t-butyl hydroperoxide; cumene hydroperoxide; and p-diisopropyl benzene peroxide. 
     
     
         9 . The process according to  claim 1 , wherein said water-soluble reducing compound (c) in the form of a solid is a compound having a solubility in water of 1 mg/100 mL or more. 
     
     
         10 . The process according to  claim 4 , wherein said water-soluble reducing compound (c) in the form of a solid is a compound having a solubility in water of 1 mg/100 mL or more. 
     
     
         11 . The process according to  claim 1 , wherein said water-soluble reducing compound (c) in the form of a solid is selected from the group consisting of sodium sulfite; potassium sulfite; calcium sulfite; ammonium sulfite; sodium hydrogensulfite; and potassium hydrogensulfite. 
     
     
         12 . The composition according to  claim 4 , wherein said water-soluble reducing compound (c) in the form of a solid is selected from the group consisting of sodium sulfite; potassium sulfite; calcium sulfite; ammonium sulfite; sodium hydrogensulfite; and potassium hydrogensulfite. 
     
     
         13 . The process according to  claim 1 , wherein said at least one liquid radical polymeric monomer (a) is at least one member selected from the group consisting of methyl (meth)acrylate; ethyl (meth)acrylate; propyl (meth)acrylate; isopropyl (meth)acrylate; butyl (meth)acrylate; isobutyl (meth)acrylate; benzyl (meth)acrylate; lauryl (meth)acrylate; 2,3-dibromopropyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate; 2-hydroxypropyl (meth)acrylate; 3-hydroxypropyl (meth)acrylate; 1,3-dihydroxypropyl (meth)acrylate; 2,3-dihydroxypropyl (meth)acrylate; 2-hydroxyethyl (meth) acrylamide; 3-methacryloyloxypropyl trimethoxysilane; 11-methacryloyloxyundecyl trimethoxysilane; (meth)acrylamide; ethylene glycol di(meth)acrylate; triethylene glycol di(meth)acrylate; propylene glycol di(meth)acrylate; polyethylene glycol di(meth)acrylate having nine or more oxyethylene groups; neopentyl glycol di(meth)acrylate; 1,6-hexanediol di(meth)acrylate; 1,10-decanediol di(meth)acrylate; dipentaerythritol di(meth)acrylate; bisphenol A diglycidyl (meth)acrylate; 2,2-bis[4-(meth)acryloyloxyethoxyphenyl]propane; 2,2-bis[4-(meth)acryloyloxypolyethoxyphenyl]propane; 2,2-bis[4[3-(meth)acryloyloxy-2-hydroxypropoxy]phenyl]propane; 1,2-bis[3-(meth)acryloyloxy-2-hydropropoxy]ethane; pentaerythritol di(meth)acrylate; 1,2-bis(3-methacryloyloxy-2-hydroxypropoxy)ethane; [2,2,4-trimethylhexamethylene bis(2-carbamoyloxyethyl)]dimethacrylate; 1,3-di(meth)acryloyloxy-2-hydroxypropane; trimethylolpropane tri(meth)acrylate; trimethylolethane tri(meth)acrylate; tetramethylolmethane tri(meth)acrylate; pentaerythritol tetra(meth)acrylate; N,N′-(2,2,4-trimethylhexamethylene) bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate; and 1,7-diacryloyloxy-2,2,6,6-tetraacryloyloxymethyl-4-oxyheptane. 
     
     
         14 . The process according to  claim 4 , wherein said at least one liquid radical polymeric monomer (a) is at least one member selected from the group consisting of methyl (meth)acrylate; ethyl (meth)acrylate; propyl (meth)acrylate; isopropyl (meth)acrylate; butyl (meth)acrylate; isobutyl (meth)acrylate; benzyl (meth)acrylate; lauryl (meth)acrylate; 2,3-dibromopropyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate; 2-hydroxypropyl (meth)acrylate; 3-hydroxypropyl (meth)acrylate; 1,3-dihydroxypropyl (meth)acrylate; 2,3-dihydroxypropyl (meth)acrylate; 2-hydroxyethyl (meth)acrylamide; 3-methacryloyloxypropyl trimethoxysilane; 11-methacryloyloxyundecyl trimethoxysilane; (meth)acrylamide; ethylene glycol di(meth)acrylate; triethylene glycol di(meth)acrylate; propylene glycol di(meth)acrylate; polyethylene glycol di(meth)acrylate having nine or more oxyethylene groups; neopentyl glycol di(meth)acrylate; 1,6-hexanediol di(meth)acrylate; 1,10-decanediol di(meth)acrylate; dipentaerythritol di(meth)acrylate; bisphenol A diglycidyl (meth)acrylate; 2,2-bis[4-(meth)acryloyloxyethoxyphenyl]propane; 2,2-bis[4-(meth)acryloyloxypolyethoxyphenyl]propane; 2,2-bis[4-[3-(meth)acryloyloxy-2-hydroxypropoxy]phenyl]propane; 1,2-bis[3-(meth)acryloyloxy-2-hydropropoxy]ethane; pentaerythritol di(meth)acrylate; 1,2-bis(3-methacryloyloxy-2-hydroxypropoxy)ethane; [2,2,4-trimethylhexamethylene bis(2-carbamoyloxyethyl)]dimethacrylate; 1,3-di(meth)acryloyloxy-2-hydroxypropane; trimethylolpropane tri(meth)acrylate; trimethylolethane tri(meth)acrylate; tetramethylolmethane tri(meth)acrylate; pentaerythritol tetra(meth)acrylate; N,N′-(2,2,4-trimethylhexamethylene) bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate; and 1,7-diacryloyloxy-2,2,6,6-tetraacryloyloxymethyl-4-oxyheptane.