US2002156144A1PendingUtilityA1

UV-curable, non-chlorinated adhesion promoters

39
Priority: Feb 9, 2001Filed: Aug 30, 2001Published: Oct 24, 2002
Est. expiryFeb 9, 2021(expired)· nominal 20-yr term from priority
Inventors:Kevin WilliamsMichael BellasCharlie Carroll Freeman, Jr.Lisa Kay Templeton
C08F 290/042C08J 7/043C08L 23/04C08L 23/10C08F 8/14C08J 2323/02C09D 7/65Y10T428/31855Y10T428/31504
39
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Claims

Abstract

Modified polyolefins are produced by reacting a functionalized polyolefin with one or more ethylenically unsaturated compounds having a functional group reactive with the functional group on the polyolefin. These modified polyolefins may then polymerize in the presence of a photoinitiator upon exposure to ultraviolet radiation and also have the capability of copolymerizing in the presence of a photoinitiator with other ethylenically unsaturated crosslinking agents upon exposure to ultraviolet radiation. These modified polyolefins may also contain pendant carboxyl groups, which have the propensity to form hydrophilic salts with amines, and therefore may be rendered water-dispersible.

Claims

exact text as granted — not AI-modified
What is claimed is:  
     
         1 . A modified polyolefin composition having pendant acrylate groups and at least one other pendant functional group comprising the reaction product of a functionalized polyolefin and one or more ethylenically unsaturated compounds having a functional group reactive with the functional group on the polyolefin.  
     
     
         2 . The modified polyolefin composition of  claim 1  wherein the functionalized polyolefin is obtained by reacting a polyolefin polymer selected from the group consisting of polyethylene, ethylene copolymers, containing alpha olefins having 2 to about 10 carbon atoms, polypropylene, propylene compolymers containing ethylene or alpha olefins having from 4 to about 10 carbon atoms, poly(1-butene), 1-butene copolymers containing ethylene or alpha olefins having 3 to about 10 carbon atoms; with monomers selected from the group consisting of unsaturated esters, unsaturated acids, unsaturated anhydrides, vinyl monomers, acrylic monomers or mixtures thereof.  
     
     
         3 . The modified polyolefin composition of  claim 2  wherein the polyolefin polymer is an ethylene-propylene copolymer comprised of about 80 mole percent propylene and about 20 mole percent ethylene.  
     
     
         4 . The modified polyolefin composition of  claim 2  wherein the unsaturated esters, unsaturated acids, unsaturated anhydrides, vinyl monomers, and acrylic monomers are selected from the group consisting of maleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride, 2,3-dimethylmaleic anhydride, maleic acid, fumaric acid, citraconic acid, 2-pentenoic acid, 2-methyl-2-pentenoic acid, dimethyl maleate, di-n-propyl maleate, diisopropyl fumarate, dimethyl itaconate, methyl acrylate, methacrylic acid, hydroxyethyl acrylate, ethyl acrylate, methyl acrylate, ethyl methacrylate, methyl crotanate, ethyl crotanate, hydroxyethyl methacrylate, hydroxy-propyl acrylate, hydroxypropyl methacrylate, and mixtures thereof.  
     
     
         5 . The modified polyolefin composition of  claim 1  wherein the ethylenically unsaturated compound is selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, polyethylene-glycol monoacrylate, polyethyleneglycol monomethacrylate, polyalkyleneglycol monomethacrylate, polypropyleneglycol monoacrylate, polypropyleneglycol mono-methacrylate, maleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride, 2,3-dimethylmaleic anhydride, maleic acid, fumaric acid, citraconic acid, mesaconic acid, glutaconic acid, acrylic acid, methacrylic acid, crotonic acid, 2-pentenoic acid, 2-methyl-2-pentenoic acid, dimethyl maleate, diethyl maleate, di-n-propyl maleate, diisopropyl maleate, dimethyl fumarate, diethyl fumarate, di-n-propyl fumarate, diisopropyl fumarate, dimethyl itaconate and mixtures thereof.  
     
     
         6 . A solvent based primer composition comprising the modified polyolefin of  claim 1 , a solvent, and a photoinitiator.  
     
     
         7 . The solvent-based primer composition of  claim 6  wherein the solvent is selected from the group consisting of ester solvents, ketone solvents, aliphatic solvents, aromatic solvents and mixtures thereof.  
     
     
         8 . The solvent-based primer composition of  claim 6  wherein said photoinitiator is selected from the group consisting of acetophenone and benzophenone/tertiary amine combinations; organic peroxides; benzoin and its ethers; and benzil and benzil ketals.  
     
     
         9 . The solvent-based primer composition of  claim 6  wherein said photoinitiator is added in the range of 0.01 to 8.0 weight percent based on the non-volatile, ethylenically unsaturated content of the coating composition.  
     
     
         10 . The solvent-based primer composition of  claim 6  further comprising auxiliary polymerizable monomers and/or oligomers.  
     
     
         11 . The solvent-based primer composition of  claim 10  wherein said auxiliary polymerizable monomers and/or oligomers is selected from the group consisting of vinyl acetate, N-vinyl pyrrolidone methyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, neopentylglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, trimethylolpropane triacrylate, (meth)acrylated urethanes, (meth)acrylated epoxies, and (meth)acrylated polyesters and polyethers.  
     
     
         12 . A water-based primer composition comprising: 
 a. the modified polyolefin composition of  claim 1;     b. from 18 to 50 weight percent, based on the weight of component (a), of a nonionic surfactant;    c. from 2 to 30 weight percent, based on the weight of component (a), of an amine;    d. a photoinitiator; and    e. water.    
     
     
         13 . The water-based primer composition of  claim 12  wherein said nonionic surfactant is selected from the group consisting of primary ethoxylated alcohols having 12 to 15 carbon atoms and secondary ethoxylated alcohols having 11 to 15 carbon atoms.  
     
     
         14 . The water-based primer composition of  claim 12  wherein said amine is a primary, secondary or tertiary amine selected from the group consisting of morpholine, 2-amino-2-methyl-1-propanol, triethylamine, tributylamine, ammonium hydroxide, 2-dimethylaminoethanol, triethanolamine, and 2-propylaminoethanol.  
     
     
         15 . The water-based primer composition of  claim 12  wherein said photoinitiator is selected from the group consisting of acetophenone and benzophenone/tertiary amine combinations; organic peroxides; benzoin and its ethers; and benzil and benzil ketals.  
     
     
         16 . The water-based primer composition of  claim 12  further comprising auxiliary polymerizable monomers and/or oligmers.  
     
     
         17 . The water-based primer composition of  claim 16  wherein said auxiliary polymerizable monomers and/or oligomers is selected from the group consisting of vinyl acetate, N-vinyl pyrrolidone methyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, neopentyl glycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, trimethylolpropane triacrylate, (meth)acrylated urethanes, (meth)acrylated epoxies, and (meth)acrylated polyesters and polyethers.  
     
     
         18 . A modified polyolefin adhesive composition comprising: 
 a. the modified polyolefin composition of  claim 1 , and    b. a photoinitiator    
     
     
         19 . The modified polyolefin adhesive composition of  claim 18  wherein said photoinitator is selected from the group consisting of acetophenone and benzophenone/tertiary amine combinations; organic peroxides; benzoin and its ethers; and benzil and benzil ketals.  
     
     
         20 . The modified polyolefin adhesive composition of  claim 18  further comprising auxiliary polymerizable monomers and/or oligomers.  
     
     
         21 . The modified polyolefin adhesive composition of  claim 20  wherein said auxiliary polymerizable monomers and/or oligomers is selected from the group consisting of vinyl acetate, N-vinyl pyrrolidone methyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, neopentyl glycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, trimethylolpropane triacrylate, (meth)acrylated urethanes, (meth)acrylated epoxies, and (meth)acrylated polyesters and polyethers.  
     
     
         22 . A process for preparing a coated substrate comprising: 
 a. applying a modified polyolefin composition to a substrate;    b. exposing the modified polyolefin composition on the substrate to an amount of ultraviolet radiation sufficient to affect a degree of curing of said modified polyolefin on said substrate; and    c. applying a paint topcoat to said substrate.    
     
     
         23 . The process of  claim 22  wherein said modified polyolefin composition is the modified polyolefin composition of  claim 1 .  
     
     
         24 . The process of  claim 22  wherein said modified polyolefin composition is the modified polyolefin of  claim 6 .  
     
     
         25 . The process of  claim 22  wherein said modified polyolefin composition is the modified polyolefin of  claim 10 .  
     
     
         26 . The process of  claim 22  wherein said modified polyolefin composition is the modified polyolefin of  claim 12 .  
     
     
         27 . The process of  claim 22  wherein said modified polyolefin composition is the modified polyolefin of  claim 16 .  
     
     
         28 . An article of manufacture comprising a substrate and a modified polyolefin.  
     
     
         29 . The article of manufacture of  claim 28  wherein said modified polyolefin is the modified polyolefin of  claim 1 .  
     
     
         30 . The article of manufacture of  claim 28  wherein said modified polyolefin is the modified polyolefin of  claim 6 .  
     
     
         31 . The article of manufacture of  claim 28  wherein said modified polyolefin is the modified polyolefin of  claim 10 .  
     
     
         32  The article of manufacture of  claim 28  wherein said modified polyolefin is the modified polyolefin of  claim 12 .  
     
     
         33 . The article of manufacture of  claim 28  wherein said modified polyolefin is the modified polyolefin of  claim 16 .  
     
     
         34 . A modified polyolefin composition having pendant acrylate groups comprising the reaction product of a functionalized polyolefin and one or more ethylenically unsaturated compounds having a functional group reactive with the functional group on the polyolefin.  
     
     
         35 . The modified polyolefin composition of  claim 34  wherein the functionalized polyolefin is obtained by reacting a polyolefin polymer selected from the group consisting of polyethylene, ethylene copolymers, containing alpha olefins having 2 to about 10 carbon atoms, polypropylene, propylene compolymers containing ethylene or alpha olefins having from 4 to about 10 carbon atoms, poly(1-butene), 1-butene copolymers containing ethylene or alpha olefins having 3 to about 10 carbon atoms; with monomers selected from the group consisting of unsaturated esters, unsaturated acids, unsaturated anhydrides, vinyl monomers, acrylic monomers or mixtures thereof.  
     
     
         36  The modified polyolefin composition of  claim 35  wherein the polyolefin polymer is an ethylene-propylene copolymer comprised of about 80 mole percent propylene and about 20 mole percent ethylene.  
     
     
         37 . The modified polyolefin composition of  claim 35  wherein the unsaturated esters, unsaturated acids, unsaturated anhydrides, vinyl monomers, and acrylic monomers are selected from the group consisting of maleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride, 2,3-dimethylmaleic anhydride, maleic acid, fumaric acid, citraconic acid, 2-pentenoic acid, 2-methyl-2-pentenoic acid, dimethyl maleate, di-n-propyl maleate, diisopropyl fumarate, dimethyl itaconate, methyl acrylate, methacrylic acid, hydroxyethyl acrylate, ethyl acrylate, methyl acrylate, ethyl methacrylate, methyl crotanate, ethyl crotanate, hydroxyethyl methacrylate, hydroxy-propyl acrylate, hydroxypropyl methacrylate, and mixtures thereof.  
     
     
         38 . The modified polyolefin composition of  claim 34  wherein the ethylenically unsaturated compound is selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, polyethylene-glycol monoacrylate, polyethyleneglycol monomethacrylate, polyalkyleneglycol monomethacrylate, polypropyleneglycol monoacrylate, polypropyleneglycol mono-methacrylate, maleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride, 2,3-dimethylmaleic anhydride, maleic acid, fumaric acid, citraconic acid, mesaconic acid, glutaconic acid, acrylic acid, methacrylic acid, crotonic acid, 2-pentenoic acid, 2-methyl-2-pentenoic acid, dimethyl maleate, diethyl maleate, di-n-propyl maleate, diisopropyl maleate, dimethyl fumarate, diethyl fumarate, di-n-propyl fumarate, diisopropyl fumarate, dimethyl itaconate and mixtures thereof.  
     
     
         39 . A solvent based primer composition comprising the modified polyolefin of  claim 34 , a solvent, and a photoinitiator.  
     
     
         40 . The solvent-based primer composition of  claim 39  wherein the solvent is selected from the group consisting of ester solvents, ketone solvents, aliphatic solvents, aromatic solvents and mixtures thereof.  
     
     
         41 . The solvent-based primer composition of  claim 39  wherein said photoinitiator is selected from the group consisting of acetophenone and benzophenone/tertiary amine combinations; organic peroxides; benzoin and its ethers; and benzil and benzil ketals.  
     
     
         42 . The solvent-based primer composition of  claim 39  wherein said photoinitiator is added in the range of 0.01 to 8.0 weight percent based on the non-volatile, ethylenically unsaturated content of the coating composition.  
     
     
         43 . The solvent-based primer composition of  claim 39  further comprising auxiliary polymerizable monomers and/or oligomers.  
     
     
         44 . The solvent-based primer composition of  claim 43  wherein said auxiliary polymerizable monomers and/or oligomers is selected from the group consisting of vinyl acetate, N-vinyl pyrrolidone methyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, neopentylglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, trimethylolpropane triacrylate, (meth)acrylated urethanes, (meth)acrylated epoxies, and (meth)acrylated polyesters and polyethers.  
     
     
         45 . A modified polyolefin adhesive composition comprising: 
 a. the modified polyolefin composition of  claim 34 , and    b. a photoinitiator    
     
     
         46 . The modified polyolefin adhesive composition of  claim 45  wherein said photoinitator is selected from the group consisting of acetophenone and benzophenone/tertiary amine combinations; organic peroxides; benzoin and its ethers; and benzil and benzil ketals.  
     
     
         47 . The modified polyolefin adhesive composition of  claim 45  further comprising auxiliary polymerizable monomers and/or oligomers.  
     
     
         48 . The modified polyolefin adhesive composition of  claim 47  wherein said auxiliary polymerizable monomers and/or oligomers is selected from the group consisting of vinyl acetate, N-vinyl pyrrolidone methyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, neopentyl glycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, trimethylolpropane triacrylate, (meth)acrylated urethanes, (meth)acrylated epoxies, and (meth)acrylated polyesters and polyethers.  
     
     
         49 . A process for preparing a coated substrate comprising: 
 a. applying a modified polyolefin composition to a substrate;    b. exposing the modified polyolefin composition on the substrate to an amount of ultraviolet radiation sufficient to affect a degree of curing of said modified polyolefin on said substrate; and    c. applying a paint topcoat to said substrate.    
     
     
         50 . The process of  claim 49  wherein said modified polyolefin composition is the modified polyolefin composition of  claim 34 .  
     
     
         51 . The process of  claim 49  wherein said modified polyolefin composition is the modified polyolefin of  claim 39 .  
     
     
         52 . The process of  claim 49  wherein said modified polyolefin composition is the modified polyolefin of  claim 45 .  
     
     
         53 . The process of  claim 39  wherein said modified polyolefin composition is the modified polyolefin of  claim 47 .  
     
     
         54 . An article of manufacture comprising a substrate and a modified polyolefin.  
     
     
         55 . The article of manufacture of  claim 54  wherein said modified polyolefin is the modified polyolefin of  claim 34 .  
     
     
         56 . The article of manufacture of  claim 54  wherein said modified polyolefin is the modified polyolefin of  claim 39 .  
     
     
         57 . The article of manufacture of  claim 54  wherein said modified polyolefin is the modified polyolefin of  claim 45 .  
     
     
         58 . The article of manufacture of  claim 54  wherein said modified polyolefin is the modified polyolefin of claim  47 .

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