Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2002-04-19
2004-07-27
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06768029
ABSTRACT:
This invention relates to the preparation of resins from unsaturated oils and to the use of the resins in forming composite and polymeric materials. More particularly, the invention relates to the formation of aldehyde and/or peroxide resin precursors through the oxidative cleavage of unsaturated oils.
BACKGROUND OF THE INVENTION
It is known to use ozonolysis to form aldehyde mixtures from soya oils, see E. H. Pryde et al., The Journal of the American Oil Chemists' Society, page 376, Vol. 38, 1961. Pryde et al disclose that the aldehyde mixtures formed from the ozonolysis are used to form resins with phenol.
The present invention relates primarily but not exclusively to the use of aldehydes derived from the ozonolysis of oils to form various useful industrial products. The invention further provides a number of novel processes for forming aldehydes from oils.
SUMMARY OF THE INVENTION
In a first aspect, the invention provides a solid composite material comprising a matrix formed from a particulate or fibrous material and a cured thermosetting resin, wherein the cured thermosetting resin is derived from an oxidative cleavage product selected from aldehydes and peroxides and mixtures thereof formed by the oxidative cleavage of an unsaturated bond in an unsaturated plant or animal oil, other than the ozonolysis cleavage product of cashew nut shell liquid.
The particulate or fibrous material can be an organic material, for example a lignocellulosic material such as a material selected from wood, straw, hemp, jute, flax, coconut fibre, rice straw and maize. One preferred lignocellulosic material comprises wood particles or wood fibre.
Although particulate or fibrous materials from natural sources arc preferred, it is also possible to use fibres or particulate materials of man-made type. For example, such fibres or particles can be formed from polymer compositions, examples being recycled plastics.
The particulate or fibrous material may alternatively (or additionally) be an inorganic material, for example an inorganic material selected from charcoal, marble (e.g crushed marble), mineral fibre, mineral particles, ceramics, crushed rock, clay, coal, slate and glass, e.g. fibre glass.
The solid composite material can take various forms such as, for example, sheet form or moulded form. Examples of composite materials in sheet form are boards and panels, particular examples being wood fibre boards such as chipboard, medium density fibre board (MDF), multilayer boards such as plywood, and building boards and panels.
The measured properties of test wood particle boards in which the binder used has been derived from oxidative cleavage products of the present invention exceed those required for boards to be of a standard acceptable in the marketplace and exceed the European Standards for Internal Bond Strength, Thickness Swell, and Bending Strength (Standards EN 319, EN 317, and EN 310).
In another aspect, the invention provides a solid foam material comprising a matrix formed from a cured resin, wherein the cured resin is derived from an oxidative cleavage product selected from aldehydes and peroxides and mixtures thereof formed by the oxidative cleavage of an unsaturated bond in an unsaturated plant or animal oil.
The foam material typically is formed by reacting the oxidative cleavage product with an isocyanate, for example methylene diphenyl diisocyanate (MDI). Foams formed in accordance with the invention can be used as inter alia insulating materials, upholstery padding and packaging.
In a further aspect, the invention provides resin compositions per se, the resin compositions being derived from an oxidative cleavage product selected from aldehydes, hemiacetals and peroxides and mixtures thereof formed by the oxidative cleavage of an unsaturated bond in an unsaturated plant or animal oil. In one embodiment, the oil is other than soya oil.
The invention further provides a resin composition as hereinbefore defined and including an acid or base catalyst. Examples of acid catalysts include sulphonic acids, particularly substituted sulphonic acids such as aromatic sulphonic acids, e.g. p-toluene-sulphonic acid. Examples of base catalysts include alkali metal hydroxides, and alkaline earth metal hydroxides, a particular basic catalyst being sodium hydroxide.
Acid and base catalysed cured resins form a further aspect of the invention.
The resins of the invention have a large number of applications, and examples of uses of the resins are in the formation and manufacture of moulded panels, non-woven materials, fibre-glass products, boards, paper treatments, fabric treatments, spun textiles, toys (e.g. children's toys), lubricants, adhesives, castings, automotive components (such as bumpers, fenders, steering wheels, interior panels and mouldings, exterior trim and mouldings), upholstery (as padding or mouldings), binding recycled materials, foundry castings and casting materials (for example binders for refractory articles), bearing, films and coatings, packaging, foams, paint components, pipes, architectural and building products such as door and window frames, varnishes, release controlling coatings such as release controlling coatings for pharmaceuticals, solid prosthetic devices and medical devices, and wood treatment agents, e.g. for preserving and modifying the properties of wood.
Articles of the type listed above, formed from resins derived from an oxidative cleavage product selected from aldehydes and peroxides and mixtures thereof formed by the oxidative cleavage of an unsaturated bond in an unsaturated plant or animal oil represent a further aspect of the invention
Plant oils useful in forming the products of the invention include unsaturated plant oils such as tung oil, mono-, di-, and tri-glyceride oils such as oils from oil seed rape, linseed, soya, olive oil, castor oil, mustard seed oil, ground nut oil, and phenolic oils such as cashew nut shell liquid (CNSL).
Oxidation of the oils is preferably effected by ozonolysis, although other oxidative methods suitable for cleaving unsaturated linkages present in the oils to form aldehydes and/or peroxides may also be used. Such alternative methods can include hydrogen peroxide, for example hydrogen peroxide in the presence of a suitable catalyst such as ferrous ions, oxidising metal salts such as periodates and permanganates.
Oxidation of the oils can be carried out in a variety of different solvents which may be either “participating” or “non-participating”. Protic solvents such as water or alcohols will tend to participate in the oxidation reaction. For example, the ozonation of unsaturated oils in a protic solvent such as an alcohol or water will lead to formation of a hydroperoxide whereas ozonides are formed in aprotic solvents such as hydrocarbons (e.g. cyclohexane, hexane) and chlorinated hydrocarbons (e.g. dichloromethane and chloroform).
The ozone can be used at concentrations in the range 1 to 10% in oxygen, and typically the treatment with ozone is continued until ozonolysis is complete. The end point for ozonolysis can be judged using thin layer chromatography (TLC), or chemical methods such as the starch iodide test. Such tests are used to check periodically for the end point of the ozonolysis, i.e. when none of the components present in the starting oil are present in the reaction mixture.
Where the oxidation is carried out using ozone, the reaction will typically be carried out at a temperature in the range −78° C. to 60° C., preferably at ambient temperature. Though the temperature of the reaction mixture may rise on introduction of ozone to as high as 45° C. it is preferable to operate at temperatures below 25° C.
After the oxidation (e.g ozonolysis) step, the intermediate ozonides and/or hydroperoxides are subject to cleavage (usually reductive cleavage) to form the aldehyde(s) and optionally hemiacetals thereof (in the case of reactions carried out in alcohols).
Reduction of the ozonolysis reaction products (e.g. ozonides) can be carried out using any of a variety of reducing conditions. Thus, reductio
Black Mairi Janet
Fitchett Colin Stanley
Khan Mohammed Lokman
Tomkinson Jeremy
Cambridge Biopolymers Limited
Carr Deborah D.
Lahive & Cockfield LLP
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