2-methyl-2-(2-methylbutan-2-ylperoxy)butane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The anhydride-functional polymers which are useful in the practice of this invention will have an average of at least two anhydride groups per molecule and are prepared by polymerizing a monomer mixture comprising the alkenyl succinic anhydride and at least one (meth)acrylic monomer under free radical addition polymerization conditions. Polymerizing under free radical addition polymerization conditions means that the monomers are reacted in the presence of a free radical source at a temperature sufficient for polymerization. Optionally, other copolymerizable monomers, such as vinyl compounds, can be included in the polymerization reaction. The monomers which are copolymerized with the alkenyl succinic anhydride should, of course, be free of any functionality which could react with the anhydride group during the polymerization. The anhydride-functional polymers can be conveniently prepared by free radical addition polymerization techniques, however, the effective incorporation of the alkenyl succinic anhydride monomers requires special considerations which are not typically involved in (meth)acrylic free radical polymerization. For example, it is preferred to conduct the polymerization at relatively high temperatures, normally in excess of 110° C., and preferably at temperatures ranging from 135° C. to about 170° C. Additionally, relatively higher amounts of initiator are generally preferred than the levels normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations will typically be within a range of 0.2 to 15, and preferably 2 to 8 weight percent of the total monomer charge. Peroxide initiators, and especially those having a relatively long half-life, e.g. greater than about 15 minutes, at these reaction temperatures are generally preferred over the azo type initiators. Di-tertiary butyl peroxide, di-(tertiary-butyl peroxyisopropyl)benzene and, especially, di-tertiary-amyl peroxide are particularly useful initiators. Additionally, aromatic hydrocarbons are generally preferred as the inert solvent rather than oxygenated inert solvents when minimal color development during the polymerization if preferred. Exxate 600 (trade name for oxohexylacetate from Exxon Chemical Company) and xylene are representative useful solvents for the polymerization. Furthermore, monomers having acrylic, rather than methacrylic, unsaturation, or monomers having allylic hydrogen atoms, such as isobornyl methacrylate, generally provide higher degrees of incorporation of the alkenyl succinic anhydride into the polymer and it is especially preferred that the monomer mixture comprise at least one such monomer. Preferrably, at least 5% by weight of the monomer mixture will be monomers having such functionality. Although it is not our intent to be bound by theory, experimental evidence indicates that under these reaction conditions, the alkenyl succinic anhydride copolymerizes as alternating and/or block copolymers and also, to at least some extent, by grafting, free radical rearrangement or other mechanism to produce quaternary carbon atoms. The acrylic monomers, or monomers having allylic hydrogen, provide a preferred site for grafting or free radical rearrangement not present in the other monomers. In order to provide the lowest possible viscosity, the anhydride-functional polymers preferably are ungelled. By "ungelled" is meant that the polymer itself is substantially free of any gel structures, insoluble fractions or internal crosslinking, and that the monomer mixture used to prepare the polymer was substantially free of any monomers having multiple polymerizable unsaturated sites. are prepared by polymerizing a monomer mixture at least one (meth)acrylic monomer under free radical addition polymerization conditions Polymerizing under free radical addition polymerization conditions are reacted in the presence of a free radical source at a temperature sufficient for polymerization could react with the anhydride group during the polymerization are not typically involved in (meth)acrylic free radical polymerization the polymerization at relatively high temperatures excess of 110° C. ranging from 135° C. to about 170° C normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations charge than oxygenated inert solvents when minimal color development during the polymerization for the polymerization

Conditions: temp:300.02; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 38.7% beta-pinene, 25.0% methyl acrylate, 30.7% hydroxypropyl acrylate, 0.8% acrylic acid and 4.8% di-t-butyl peroxide was continuously fed to a 5 gallon continuous stirred tank reactor at a rate calculated to give a average residence time of 20 minutes. The reactor was maintained at a pressure of 500 psig and a temperature of 365° F. The reaction product was continuously pumped to a 30 gallon flash tank maintained at 20% fill level together with di-t-amyl peroxide (4% by weight on reaction product). The contents of the flash tank were maintained at 300° F. The output from the flash tank was mixed with sufficient butyl acetate in a static mixer to reduce the solids content to 81% and drained into storage containers. The reaction was run for a period of 6.5 hours. The resulting resin had a weight average molecular weight of 5000. was continuously fed to a 5 gallon continuous stirred tank reactor at a rate to give a average residence time of 20 minutes The reactor was maintained at a pressure of 500 psig a temperature of 365° F

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The anhydride-functional polymers which are useful in the practice of this invention will have an average of at least two anhydride groups per molecule and are prepared by polymerizing a monomer mixture comprising the alkenyl succinic anhydride and at least one (meth)acrylic monomer under free radical addition polymerization conditions. Polymerizing under free radical addition polymerization conditions means that the monomers are reacted in the presence of a free radical source at a temperature sufficient for polymerization. Optionally, other copolymerizable monomers, such as vinyl compounds, can be included in the polymerization reaction. The monomers which are copolymerized with the alkenyl succinic anhydride should, of course, be free of any functionality which could react with the anhydride group during the polymerization. The anhydride-functional polymers can be conveniently prepared by free radical addition polymerization techniques, however, the effective incorporation of the alkenyl succinic anhydride monomers requires special considerations which are not typically involved in (meth)acrylic free radical polymerization. For example, it is preferred to conduct the polymerization at relatively high temperatures, normally in excess of 110° C., and preferably at temperatures ranging from 135° C. to about 170° C. Additionally, relatively higher amounts of initiator are generally preferred than the levels normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations will typically be within a range of 0.2 to 15, and preferably 2 to 8 weight percent of the total monomer charge. Peroxide initiators, and especially those having a relatively long half-life, e.g. greater than about 15 minutes, at these reaction temperatures are generally preferred over the azo type initiators. Di-tertiary butyl peroxide, di-(tertiary-butyl peroxyisopropyl)benzene and, especially, di-tertiary-amyl peroxide are particularly useful initiators. Additionally, aromatic hydrocarbons are generally preferred as the inert solvent rather than oxygenated inert solvents when minimal color development during the polymerization if preferred. Exxate 600 (trade name for oxohexylacetate from Exxon Chemical Company) and xylene are representative useful solvents for the polymerization. Furthermore, monomers having acrylic, rather than methacrylic, unsaturation, or monomers having allylic hydrogen atoms, such as isobornyl methacrylate, generally provide higher degrees of incorporation of the alkenyl succinic anhydride into the polymer and it is especially preferred that the monomer mixture comprise at least one such monomer. Preferrably, at least 5% by weight of the monomer mixture will be monomers having such functionality. Although it is not our intent to be bound by theory, experimental evidence indicates that under these reaction conditions, the alkenyl succinic anhydride copolymerizes as alternating and/or block copolymers and also, to at least some extent, by grafting, free radical rearrangement or other mechanism to produce quaternary carbon atoms. The acrylic monomers, or monomers having allylic hydrogen, provide a preferred site for grafting or free radical rearrangement not present in the other monomers. In order to provide the lowest possible viscosity, the anhydride-functional polymers preferably are ungelled. By "ungelled" is meant that the polymer itself is substantially free of any gel structures, insoluble fractions or internal crosslinking, and that the monomer mixture used to prepare the polymer was substantially free of any monomers having multiple polymerizable unsaturated sites. are prepared by polymerizing a monomer mixture at least one (meth)acrylic monomer under free radical addition polymerization conditions Polymerizing under free radical addition polymerization conditions are reacted in the presence of a free radical source at a temperature sufficient for polymerization could react with the anhydride group during the polymerization are not typically involved in (meth)acrylic free radical polymerization the polymerization at relatively high temperatures excess of 110° C. ranging from 135° C. to about 170° C normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations charge than oxygenated inert solvents when minimal color development during the polymerization for the polymerization

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The anhydride-functional polymers which are useful in the practice of this invention will have an average of at least two anhydride groups per molecule and are prepared by polymerizing a monomer mixture comprising the alkenyl succinic anhydride and at least one (meth)acrylic monomer under free radical addition polymerization conditions. Polymerizing under free radical addition polymerization conditions means that the monomers are reacted in the presence of a free radical source at a temperature sufficient for polymerization. Optionally, other copolymerizable monomers, such as vinyl compounds, can be included in the polymerization reaction. The monomers which are copolymerized with the alkenyl succinic anhydride should, of course, be free of any functionality which could react with the anhydride group during the polymerization. The anhydride-functional polymers can be conveniently prepared by free radical addition polymerization techniques, however, the effective incorporation of the alkenyl succinic anhydride monomers requires special considerations which are not typically involved in (meth)acrylic free radical polymerization. For example, it is preferred to conduct the polymerization at relatively high temperatures, normally in excess of 110° C., and preferably at temperatures ranging from 135° C. to about 170° C. Additionally, relatively higher amounts of initiator are generally preferred than the levels normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations will typically be within a range of 0.2 to 15, and preferably 2 to 8 weight percent of the total monomer charge. Peroxide initiators, and especially those having a relatively long half-life, e.g. greater than about 15 minutes, at these reaction temperatures are generally preferred over the azo type initiators. Di-tertiary butyl peroxide, di-(tertiary-butyl peroxyisopropyl)benzene and, especially, di-tertiary-amyl peroxide are particularly useful initiators. Additionally, aromatic hydrocarbons are generally preferred as the inert solvent rather than oxygenated inert solvents when minimal color development during the polymerization if preferred. Exxate 600 (trade name for oxohexylacetate from Exxon Chemical Company) and xylene are representative useful solvents for the polymerization. Furthermore, monomers having acrylic, rather than methacrylic, unsaturation, or monomers having allylic hydrogen atoms, such as isobornyl methacrylate, generally provide higher degrees of incorporation of the alkenyl succinic anhydride into the polymer and it is especially preferred that the monomer mixture comprise at least one such monomer. Preferrably, at least 5% by weight of the monomer mixture will be monomers having such functionality. Although it is not our intent to be bound by theory, experimental evidence indicates that under these reaction conditions, the alkenyl succinic anhydride copolymerizes as alternating and/or block copolymers and also, to at least some extent, by grafting, free radical rearrangement or other mechanism to produce quaternary carbon atoms. The acrylic monomers, or monomers having allylic hydrogen, provide a preferred site for grafting or free radical rearrangement not present in the other monomers. In order to provide the lowest possible viscosity, the anhydride-functional polymers preferably are ungelled. By "ungelled" is meant that the polymer itself is substantially free of any gel structures, insoluble fractions or internal crosslinking, and that the monomer mixture used to prepare the polymer was substantially free of any monomers having multiple polymerizable unsaturated sites. are prepared by polymerizing a monomer mixture at least one (meth)acrylic monomer under free radical addition polymerization conditions Polymerizing under free radical addition polymerization conditions are reacted in the presence of a free radical source at a temperature sufficient for polymerization could react with the anhydride group during the polymerization are not typically involved in (meth)acrylic free radical polymerization the polymerization at relatively high temperatures excess of 110° C. ranging from 135° C. to about 170° C normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations charge than oxygenated inert solvents when minimal color development during the polymerization for the polymerization

Conditions: temp:300.02; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 38.7% beta-pinene, 25.0% methyl acrylate, 30.7% hydroxypropyl acrylate, 0.8% acrylic acid and 4.8% di-t-butyl peroxide was continuously fed to a 5 gallon continuous stirred tank reactor at a rate calculated to give a average residence time of 20 minutes. The reactor was maintained at a pressure of 500 psig and a temperature of 365° F. The reaction product was continuously pumped to a 30 gallon flash tank maintained at 20% fill level together with di-t-amyl peroxide (4% by weight on reaction product). The contents of the flash tank were maintained at 300° F. The output from the flash tank was mixed with sufficient butyl acetate in a static mixer to reduce the solids content to 81% and drained into storage containers. The reaction was run for a period of 6.5 hours. The resulting resin had a weight average molecular weight of 5000. was continuously fed to a 5 gallon continuous stirred tank reactor at a rate to give a average residence time of 20 minutes The reactor was maintained at a pressure of 500 psig a temperature of 365° F

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In similar manner, although optimal conditions may vary, hydrogen peroxide may be reacted with methyl t-amyl ether to provide t-amyl hydroperoxide or di-t-amyl peroxide; with methyl t-hexyl ether to provide t-hexyl hydroperoxide or di-t-hexyl peroxide; with ethyl t-butyl ether to provide t-butyl hydroperoxide or di-t-butyl peroxide; with ethyl t-amyl ether to provide t-amyl hydroperoxide or di-t-amyl peroxide; with ethyl t-hexyl ether to provide t-hexyl hydroperoxide or di-t-hexyl peroxide; with n-propyl t-butyl ether to provide t-butyl hydroperoxide or di-t-butyl peroxide; with n-propyl t-amyl ether to provide t-amyl hydroperoxide or di t-amyl peroxide; or with n-propyl t-hexyl ether to provide t-hexyl hydroperoxide or di-t-hexyl peroxide. Illustrative of reactions employing hydroperoxide reactants are the reaction of t-butyl hydroperoxide with methyl t-butyl ether to provide di-t-butyl peroxide; the reaction of t-hexyl hydroperoxide with methyl t-hexyl ether to provide di-t-hexyl peroxide; the reaction of t-butyl hydroperoxide with methyl t-amyl ether to provide t-butyl t-amyl peroxide; the reaction of t-butyl hydroperoxide with methyl t-hexyl ether to provide t-butyl t-hexyl peroxide; and the reaction of t-amyl hydroperoxide with ethyl t-hexyl ether to provide t-amyl t-hexyl peroxide.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,5-di(tert.-butyl peroxy)-2,5-dimethyl-3-hexane; 2,5-di(tert.-butyl peroxy)-2,5-dimethyl hexane, tert.-butylcumyl peroxide; di(tert.-butyl)peroxide; dicumyl peroxide; di(tert.-butyl peroxide-iso-propyl)benzene, butyl-4,4-bis(tert.-butyl peroxy)valerate; 1,1-bis(tert.-butyl peroxy)-3,3,5-trimethyl cyclohexane; tert.-butylperoxy benzoate, diene benzoyl peroxide are e.g. suitable as a peroxide.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-butyl peroxide and cumyl peroxide;

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The anhydride-functional polymers which are useful in the practice of this invention will have an average of at least two anhydride groups per molecule and are prepared by polymerizing a monomer mixture comprising the alkenyl succinic anhydride and at least one (meth)acrylic monomer under free radical addition polymerization conditions. Polymerizing under free radical addition polymerization conditions means that the monomers are reacted in the presence of a free radical source at a temperature sufficient for polymerization. Optionally, other copolymerizable monomers, such as vinyl compounds, can be included in the polymerization reaction. The monomers which are copolymerized with the alkenyl succinic anhydride should, of course, be free of any functionality which could react with the anhydride group during the polymerization. The anhydride-functional polymers can be conveniently prepared by free radical addition polymerization techniques, however, the effective incorporation of the alkenyl succinic anhydride monomers requires special considerations which are not typically involved in (meth)acrylic free radical polymerization. For example, it is preferred to conduct the polymerization at relatively high temperatures, normally in excess of 110° C., and preferably at temperatures ranging from 135° C. to about 170° C. Additionally, relatively higher amounts of initiator are generally preferred than the levels normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations will typically be within a range of 0.2 to 15, and preferably 2 to 8 weight percent of the total monomer charge. Peroxide initiators, and especially those having a relatively long half-life, e.g. greater than about 15 minutes, at these reaction temperatures are generally preferred over the azo type initiators. Di-tertiary butyl peroxide, di-(tertiary-butyl peroxyisopropyl)benzene and, especially, di-tertiary-amyl peroxide are particularly useful initiators. Additionally, aromatic hydrocarbons are generally preferred as the inert solvent rather than oxygenated inert solvents when minimal color development during the polymerization if preferred. Exxate 600 (trade name for oxohexylacetate from Exxon Chemical Company) and xylene are representative useful solvents for the polymerization. Furthermore, monomers having acrylic, rather than methacrylic, unsaturation, or monomers having allylic hydrogen atoms, such as isobornyl methacrylate, generally provide higher degrees of incorporation of the alkenyl succinic anhydride into the polymer and it is especially preferred that the monomer mixture comprise at least one such monomer. Preferrably, at least 5% by weight of the monomer mixture will be monomers having such functionality. Although it is not our intent to be bound by theory, experimental evidence indicates that under these reaction conditions, the alkenyl succinic anhydride copolymerizes as alternating and/or block copolymers and also, to at least some extent, by grafting, free radical rearrangement or other mechanism to produce quaternary carbon atoms. The acrylic monomers, or monomers having allylic hydrogen, provide a preferred site for grafting or free radical rearrangement not present in the other monomers. In order to provide the lowest possible viscosity, the anhydride-functional polymers preferably are ungelled. By "ungelled" is meant that the polymer itself is substantially free of any gel structures, insoluble fractions or internal crosslinking, and that the monomer mixture used to prepare the polymer was substantially free of any monomers having multiple polymerizable unsaturated sites. are prepared by polymerizing a monomer mixture at least one (meth)acrylic monomer under free radical addition polymerization conditions Polymerizing under free radical addition polymerization conditions are reacted in the presence of a free radical source at a temperature sufficient for polymerization could react with the anhydride group during the polymerization are not typically involved in (meth)acrylic free radical polymerization the polymerization at relatively high temperatures excess of 110° C. ranging from 135° C. to about 170° C normally used for conventional free radical polymerization of (meth)acrylic monomers and initiator concentrations charge than oxygenated inert solvents when minimal color development during the polymerization for the polymerization