Copolymers of vinyl pyrrolidone and a C30 alphaolefin in flake or powder form, process for making same and personal care compositions therewith

Abstract: Alkylated vinyl pyrrolidone copolymers are claimed. These polymers contain an olefinic monomer fraction which is predominantly C₃₀ alkyl olefin. The polymers can be made in the physical form of flakes or powders, and prepared by a novel process. The polymers can be used in personal care compositions.

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to linear copolymers of vinyl pyrrolidone and long chain alpha-olefins and, more particularly, to such copolymers in the form of flakes or powders. 2. Description of the Prior Art U.S. Patents 3,406,238; 3,417,054; 3,309,365; 3,423,381; and 3,423,367 describe the preparation of alkylated polymers of heterocyclic N-vinyl monomers by the simultaneous polymerization and alkylation of heterocyclic N-vinyl monomers and long chain alpha-olefin comonomers. Alkylated vinyl pyrrolidone copolymers, for example, are known as Ganex® polymers, and are sold by International Specialty Products. Typically, Ganex® V-216 is sold in the form of a straw-colored viscous liquid while Ganex® V-220 is a waxy solid. Other Ganex® polymers having different long chain alkyl groups therein are known but these are also prepared as bulk solids. The use of Ganex® copolymers as a waterproofing agent in sunscreen products is well known. However, its main disadvantage of bulk solids is that it is inconvenient to process into such formulations. GB-A-1 301 373 discloses the use of N-vinylpyrrolidone in cosmetic compositions suitable as hair lacquers and wave setting lotions. Accordingly, it is desired to provide such copolymers as flakes or powders which could be handled more easily, and, perhaps, have superior waterproofing properties in a personal care composition, such as a sunscreen composition than the bulk form. Another sought-after objective of this invention is to provide a process for making copolymers of vinyl pyrrolidone and long chain alpha-olefins in the physical form of flakes or powders. These and other objects and features of the invention will be made apparent from the following description of the invention. SUMMARY OF THE INVENTION What is provided herein is a process for making copolymers of vinyl pyrrolidone and long chain alpha-olefins in flake or powder form which is characterized by: (a) copolymerizing vinyl pyrrolidone and an olefinic fraction, containing predominately C₃₀ alpha-olefin in a organic solvent in the presence of a free radical initiator at a solids level of at least about 40% by weight at a temperature sufficient for activation of the initiator, (b) removing the solvent, (c) forming the molten copolymer reaction product into sheets, and (d) comminuting the sheets into flakes or powders, the melting point of the product being at least about 50°C. In a preferred form, the copolymer may comprise from 10 to 40% of vinyl pyrrolidone and from 60 to 90% of the olefinic fraction. The present invention further provides a personal care composition having improved water proofing properties and high temperature stability comprising a) an active personal care material and b) a copolymer of vinyl pyrrolidone and an olefinic fraction containing predominantly a C₃₀ alpha-olefin in flake or powder form having a melting point of at least 50°C. The personal care composition may be a sunscreen, an eye shadow or a lip balm. In a preferred form, the copolymer comprises about 1-10% by weight of the personal care composition. In a further embodiment of the present invention a sunscreen composition is provided wherein the active personal care material comprises (a) an active sunscreen material, and (b) about 1-10% by weight of a copolymer of vinyl pyrrolidone and an olefinic fraction containing predominantly a C₃₀ alpha-olefin in flake or powder form having a melting point of at least 50°C. In a still further preferred form of the invention, the organic solvent is butanol or hexanol, the melting point of the copolymer is at least 60°C., the copolymer comprises about 20% by weight of vinyl pyrrolidone and 80% by weight of a C₃₀ alpha-olefin, and residual olefin is substantially absent from the copolymer. DETAILED DESCRIPTION In accordance with the process of the invention, a mixture of vinyl pyrrolidone and a long chain alpha-olefin, such as a linear C₃₀ alpha-olefin fraction, is provided in an organic solvent, at a solids level of at least about 40% by weight, preferaby 50% or more. It is desirable that the solvent is high boiling such as butanol or hexanol. The mixture is copolymerized in the presence of about 5-15% by weight of a free radical initiator based on vinyl pyrrolidone at a temperature sufficient for activation of the initiator, usually about 130-135°C. The solvent is then removed from the reaction product by stripping off the solvent, forming the resultant molten copolymer into sheets, and comminuting the sheets into flakes or powders. The melting point of the resultant copolymer sheets is at least 50°C., preferably at least 60°C. Embodiments of the invention will now be described by reference to the following working examples. EXAMPLE 1 A glass kettle fitted with a nitrogen inlet, a thermometer, a condenser and an anchor agitator was charged with hexanol solvent and a predominately C₃₀ alpha-olefin fraction ("Gulfene C₃₀+" sold by Chevron Olefins Division, Houston, TX) monomer. The mixture was heated to 80°C. to dissolve the olefin and then stabilized vinyl pyrrolidone monomer and 12 g. of t-butyl peroxide initiator were added. The solids level of the solution was 51%. The reaction solution then was heated to 130-140°C. and held at that temperature for 20-24 hours. The reaction product was cooled to 80°C., and the solvent was removed under vacuum. The molten residue then was cooled into sheets. The resultant copolymer, which had a melting point of 63-64°C., was comminuted into flakes and powders. The bromine number of the product was 1-10, which indicated that the residual alpha-olefin level was quite low. EXAMPLE 2 The procedure of Example 1 was followed using butanol solvent with similar results. EXAMPLE 3 The material of Examples 1 and 2 were used in a conventional sunscreen composition. The composition exhibited superior waterproofing properties versus the same composition containing similar amounts of Ganex® V-220 (ISP) which exists in bulk form as a waxy solid.

Claims: Claims for the following Contracting States : BE, CH, LI, DE, FR, GB, GR, IT, LU, PT, SE A copolymer of vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin which copolymer is in flake or powder form having a melting point of at least 50°C. A copolymer according to claim 1 which comprises from 10 to 40% of said vinyl pyrrolidone and from 60 to 90% of said olefinic fraction. A copolymer according to claim 2 which comprises about 20% by weight of vinyl pyrrolidone and about 80% by weight of said C₃₀ alpha-olefin. A copolymer according to any one of claims 1 to 3 wherein the melting point is at least 60°C. A copolymer according to any one of claims 1 to 4 wherein residual C₃₀ alpha-olefin is substantially absent. A process for making copolymers of vinyl pyrrolidone and an alpha-olefin in flake or powder form which comprises: (a) copolymerizing vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin in organic solvent in the presence of a free radical initiator at a solids level of at least about 40% by weight and at a temperature sufficient for activation of the initiator, (b) removing the solvent, (c) forming the resultant molten copolymer into sheets, and (d) communiting the sheets into flakes or powders, the melting point of the copolymers being at least about 50°C. A process according to claim 6 wherein said organic solvent is butanol or hexanol. A process according to claim 6 or claim 7 wherein the copolymer is as defined in any one of claims 2 to 5. A process according to any one of the preceding claims wherein the initiator level is about 5-15% by weight based on vinyl pyrrolidone. A personal care composition having improved waterproofing properties and high temperature stability comprising (a) an active personal care material and (b) a copolymer of vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin which copolymer is provided in flake or powder form having a melting point of at least 50°C. A personal care composition according to claim 10 where (a) is a sunscreen, an eye shadow or a lip balm. A personal care composition according to claim 10 wherein said melting point is at least 60°C., and the copolymer comprises about 20% by weight vinyl pyrrolidone and about 80% by weight of said C₃₀ alpha-olefin. A personal care composition according to claim 10 wherein said copolymer comprises about 1-10% by weight of the composition. A sunscreen composition according to claim 10 the material comprising (a) an active sunscreen material, and (b) about 1-10% by weight of a copolymer of vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin which copolymer is provided in flake or powder form having a melting point of at least 50°C. Claims for the following Contracting State : ES A personal care composition including a copolymer of vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin which copolymer is in flake or powder form having a melting point of at least 50°C. A composition according to claim 1 which comprises from 10 to 40% of said vinyl pyrrolidone and from 60 to 90% of said olefinic fraction. A composition according to claim 2 which comprises about 20% by weight of vinyl pyrrolidone and about 80% by weight of said C₃₀ alpha-olefin. A composition according to any one of claims 1 to 3 wherein the melting point is at least 60°C. A composition according to any one of claims 1 to 4 wherein residual C₃₀ alpha-olefin is substantially absent. A process for making copolymers of vinyl pyrrolidone and an alpha-olefin in flake or powder form which comprises: (a) copolymerizing vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin in organic solvent in the presence of a free radical initiator at a solids level of at least about 40% by weight and at a temperature sufficient for activation of the initiator, (b) removing the solvent, (c) forming the resultant molten copolymer into sheets, and (d) communiting the sheets into flakes or powders, the melting point of the copolymers being at least about 50°C. A process according to claim 6 wherein said organic solvent is butanol or hexanol. A process according to claim 6 or claim 7 wherein the copolymer is as defined in any one of claims 2 to 5. A process according to any one of the preceding claims wherein the initiator level is about 5-15% by weight based on vinyl pyrrolidone. A personal care composition having improved waterproofing properties and high temperature stability comprising (a) an active personal care material and (b) a copolymer of vinyl pyrrolidone and an olefinic fraction containing predominately a C₃₀ alpha-olefin which copolymer is provided in flake or powder form having a melting point of at least 50°C. A personal care composition according to claim 10 where (a) is a sunscreen, an eye shadow or a lip balm. A personal care composition according to claim 10 wherein said melting point is at least 60°C., and the copolymer comprises about 20% by weight vinyl pyrrolidone and about 80% by weight of said C₃₀ alpha-olefin. A personal care composition according to claim 10 wherein said copolymer comprises about 1-10% by weight of the composition. A sunscreen composition according to claim 10 the material comprising (a) an active sunscreen material, and (b) about 1-10% by weight of a copolymer of vinyl pyrrolidone And an olefinic fraction containing predominately a C₃₀ alpha-olefin which copolymer is provided in flake or powder form having a melting point of at least 50°C.

Inventors: KOPOLOW STEPHEN L, KOPOLOW, STEPHEN L.
Applicants: ISP INVESTMENTS INC, ISP INVESTMENTS INC.
Application year: 1992
Main classification: C08F226
IPC codes: C08F210, C08J3, A61Q19, C08F226, C08F26, A61Q17, A61K8