NATURAL OIL METATHESIS COMPOSITIONS AND METHODS

• US 20130344012A1
• Filed: 06/20/2013
• Published: 12/26/2013
• Est. Priority Date: 06/20/2012
• Status: Active Grant

• Current Assignee: Wilmar Trading Pte., Ltd. (Wilmar International Limited)
• Original Assignee: Elevance Renewable Sciences Incorporated
• Inventors: Cohen, Steven A., Bergmann, Benjamin, DiBiase, Stephen A., Christensen, S. Alexander, Morie-Bebel, M. Michelle, Ilseman, Alexander D.
• Granted Patent: US 9,890,348 B2
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 8/375 the alcohol moiety containing more than one hydroxy group
• CPC Class Codes: A61K 8/4973 with oxygen as the only hetero atom
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: C10G 3/42 Catalytic treatment
• CPC Class Codes: C11B 3/008 by filtration, e.g. including ultra filtration, dialysis C11B3/005 takes precedence
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/10 Ester interchange
• CPC Class Codes: Y02P 30/20 using bio-feedstock

Abstract

A metathesized natural oil composition comprising (i) a mixture olefins and/or esters, or (ii) a metathesized natural oil, is disclosed. The metathesized natural oil composition has a number average molecular weight in the range from about 100 g/mol to about 150,000 g/mol, a weight average molecular weight in the range from about 1,000 g/mol to about 100,000 g/mol, a z-average molecular weight in the range from about 5,000 g/mol to about 1,000,000 g/mol, and a polydispersity index of about 1 to about 20. The metathesized natural oil composition is metathesized at least once.

Claims

1. A metathesized natural oil composition comprising (i) a mixture olefins and/or esters, or (ii) a metathesized natural oil, wherein the metathesized natural oil composition has a number average molecular weight in the range from about 100 g/mol to about 150,000 g/mol, a weight average molecular weight in the range from about 1,000 g/mol to about 100,000 g/mol, a z-average molecular weight in the range from about 5,000 g/mol to about 1,000,000 g/mol, and a polydispersity index of about 1 to about 20, and further wherein the metathesized natural oil composition is metathesized at least once.

2. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition has a number average molecular weight in the range from about 2,000 g/mol to about 4,000 g/mol, a weight average molecular weight in the range from about 7,000 g/mol to about 35,000 g/mol, and a z-average molecular weight in the range from about 10,000 g/mol to about 125,000 g/mol, and a polydispersity index of about 2 to about 12.

3. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition has a number average molecular weight in the range from about 2,300 g/mol to about 3,400 g/mol, a weight average molecular weight in the range from about 9,600 g/mol to about 31,500 g/mol, and a z-average molecular weight in the range from about 28,000 g/mol to about 111,000 g/mol, and a polydispersity index of about 4 to about 12.

4. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition has a dynamic viscosity at 40°

C. of between about 200 centipoise and 3500 centipoise.

5. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition has a dynamic viscosity at 40°

C. of between about 550 centipoise and 3250 centipoise.

6. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition has a dynamic viscosity at 100°

C. of between about 75 centipoise and 600 centipoise.

7. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition is made by reacting a natural oil feedstock in the presence of a metathesis catalyst to form a first metathesized natural oil product, and further wherein the first metathesized natural oil product is self-metathesized to form another metathesized natural oil product.

8. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition is made by reacting a natural oil in the presence of a metathesis catalyst to form a first metathesized natural oil product, and further wherein the first metathesized natural oil product is cross-metathesized with a natural oil to form another metathesized natural oil product.

9. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition may be subject to steam stripping at a temperature of between about 100°

C. and 250°

C.

10. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition may be subject to reduced pressure conditions to remove C12 or lighter olefins.

11. The metathesized natural oil composition of claim 1, wherein when the metathesized natural oil composition comprises a mixture of olefins and esters, and further wherein the mixture of olefins and esters can be separated into olefins and esters, and thereafter transesterifying the esters in the presence of an alcohol to form a transesterified product.

12. The metathesized natural oil composition of claim 1, wherein the molecular weight of the metathesized natural oil composition can be increased by transesterifying the metathesized natural oil composition with diesters.

13. The metathesized natural oil composition of claim 1, wherein the molecular weight of the metathesized natural oil composition can be increased by transesterifying the metathesized natural oil composition with diacids.

14. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil in the metathesized natural oil composition is selected from the group consisting of metathesized canola oil, metathesized rapeseed oil, metathesized coconut oil, metathesized corn oil, metathesized cottonseed oil, metathesized olive oil, metathesized palm oil, metathesized peanut oil, metathesized safflower oil, metathesized sesame oil, metathesized soybean oil, metathesized sunflower oil, metathesized linseed oil, metathesized palm kernel oil, metathesized tung oil, metathesized jatropha oil, metathesized mustard oil, metathesized castor oil, metathesized camelina oil, metathesized pennycress oil, metathesized derivatives of these oils, and mixtures thereof.

15. The metathesized natural oil composition of claim 1, wherein the metathesized natural oil composition may be utilized independently and/or incorporated into various formulations and used as functional ingredients, selected from the group consisting of dimethicone replacements, laundry detergents, fabric softeners, emollients, hair fixative polymers, rheology modifiers, specialty conditioning polymers, surfactants, UV absorbers, solvents, humectants, occlusives, cosmetics, lip balms, lipsticks, hair dressings, sun care products, moisturizer, fragrance sticks, perfume carriers, skin feel agents, shampoos/conditioners, bar soaps, hand soaps/washes, bubble baths, body washes, facial cleansers, shower gels, wipes, baby cleansing products, creams/lotions, antiperspirants/deodorants, lubricants, functional fluids, fuels and fuel additives, additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, antistatic agents in the textile and plastics industries, flotation agents, gelling agents, epoxy curing agents, corrosion inhibitors, pigment wetting agents, in cleaning compositions, plastics, coatings, adhesives, skin feel agents, film formers, rheological modifiers, release agents, conditioners dispersants, hydrotropes, industrial and institutional cleaning products, oil field applications, gypsum foamers, sealants, agricultural formulations, enhanced oil recovery compositions, solvent products, gypsum products, gels, semi-solids, detergents, heavy duty liquid detergents, light duty liquid detergents, liquid detergent softeners, antistat formulations, dryer softeners, hard surface cleaners for household, autodishes, rinse aids, laundry additives, carpet cleaners, softergents, single rinse fabric softeners, oven cleaners, car washes, transportation cleaners, drain cleaners, defoamers, anti-foamers, foam boosters, anti-dust/dust repellants, industrial cleaners, institutional cleaners, janitorial cleaners, glass cleaners, graffiti removers, concrete cleaners, metal/machine parts cleaners, pesticides, agricultural formulations and food service cleaners, plasticizers, asphalt additives and emulsifiers, friction reducing agents, film formers, rheological modifiers, biocides, biocide potentiators, release agents, household cleaning products, including liquid and powdered laundry detergents, liquid and sheet fabric softeners, hard and soft surface cleaners, sanitizers and disinfectants, and industrial cleaning products, emulsion polymerization, including processes for the manufacture of latex and for use as surfactants as wetting agents, formulation inerts in pesticide applications or as adjuvants used in conjunction with the delivery of pesticides including agricultural crop protection turf and ornamental, home and garden, and professional applications, institutional cleaning products, oil field applications, including oil and gas transport, production, stimulation and drilling chemicals and reservoir conformance and enhancement, organoclays for drilling muds, specialty foamers for foam control or dispersancy in the manufacturing process of gypsum, cement wall board, concrete additives and firefighting foams, paints and coalescing agents, paint thickeners, or other applications requiring cold tolerance performance or winterization.

16. A metathesized natural oil composition comprising (i) a mixture olefins and/or esters, or (ii) a metathesized natural oil, wherein the metathesized natural oil composition has a number average molecular weight in the range from about 2,300 g/mol to about 3,400 g/mol, a weight average molecular weight in the range from about 9,600 g/mol to about 31,500 g/mol, and a z-average molecular weight in the range from about 28,000 g/mol to about 111,000 g/mol, and a polydispersity index of about 4 to about 12, and further wherein the metathesized natural oil composition is metathesized at least twice.