Vegetable oil adducts as emollients in skin and hair care products

• US 4,740,367 A
• Filed: 06/23/1986
• Issued: 04/26/1988
• Est. Priority Date: 07/19/1984
• Status: Expired due to Term

• Current Assignee: Meadwestvaco (WestRock Company)
• Original Assignee: Westvaco Corporation (Meadwestvaco Corporation)
• Inventors: Starr, Fredricke S., Force, Carlton G.
• Primary Examiner(s): Ore, Dale R.
• Application Number:
  US06/877,464
• Time in Patent Office: 673 Days
• Field of Search: 514/844, 424/47, 424/70
• US Class Current: 424/47
• CPC Class Codes: A61K 8/922 of vegetable origin
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 17/00 Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair
• CPC Class Codes: A61Q 5/006 Antidandruff preparations
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners

Abstract

Certain vegetable oil lipid adducts, either alone or in combination with disproportionated vegetable oils, are disclosed which provide persistent softening effects upon incorporation in skin and hair care preparations. The emollients of the invention include both the water-soluble and water-insoluble salts of the vegetable oil adducts. The certain vegetable oil adducts of the invention are the adducts prepared from vegetable oils containing nonconjugated polyunsaturated fatty acid esters which are conjugated and then modified via Diels-Alder addition with acrylic acid, fumaric acid, or maleic anhydride.

Claims

1. An improved skin care formulation including, as an emollient therefor, vegetable oil adducts, wherein the improvement comprises enhanced persistency of softening provided by adducts prepared from vegetable oils containing non-conjugated polyunsaturated fatty acid esters which are conjugated and elaidinized and then modified via Diels-Alder addition with a member of the group consisting of acrylic acid, fumaric acid or maleic anhydride.

2. The improved skin care formulation of claim 1 wherein the vegetable oil is soybean oil.

3. The improved skin care formulation of claim 1 which also includes as an emollient a member of the group selected from a vegetable oil, a modified vegetable oil produced by disproportionating the vegetable oil to conjugate the double bonds in the linoleic and linolenic acid groups present in the oil, and a mixture thereof.

4. The improved skin care formulation of claim 1 wherein the Diels-Alder modification reaction occurs by reacting the vegetable oil with fumaric acid.

5. The improved skin care formulation of claim 1 wherein the vegetable oil adduct has the general formula ##STR2## wherein x and y are integers from 3 to 9, x and y together equal 12, at least one Z is a carboxylic acid group, and any remaining Z is hydrogen, and R₁ and R₂ are saturated/unsaturated hydrocarbon radicals.

6. The improved skin care formulation of claim 5 wherein each Z is a carboxylic acid group in which all or part of the carboxyl groups may be in the anhydride form.

7. The improved skin care formulation of claim 1 wherein the vegetable oil adducts are subsequently converted into their soap forms selected from the group consisting of the soluble alkali metal and amine soaps and the insoluble alkaline earth and higher valent metal soaps.

8. The improved skin care formulation of claim 1 comprised of soybean oil-fumaric acid Diels-Alder adduct 16.00%, mineral oil 4.00%, cetyl alcohol 2.00%, ethoxylated stearyl alcohol and stearyl alcohol blend 4.00%, glycerin 5.00%, methylparaben 0.18%, and purified water, USP 68.82%.

9. The improved skin care formulation of claim 1 as follows:

soybean oil-fumaric acid Diels-Alder adduct 16.00%, mineral oil 4.00%, cetyl alcohol 4.00%, ethoxylated stearyl alcohol and stearyl alcohol blend 6.00%, glycerin 5.00%, methylparaben 0.15%, and purified water, USP 64.85%.

10. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 5.0%, cetyl alcohol is 5.0%, mineral oil is 4.0%, isopropyl myristate 5.0%, propylparaben 0.1%;

B is glycerin 8.0%, triethanolamine 3.0%, methylparaben 0.2%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

11. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 8.0%, cetyl alcohol 2.0%, propylene glycol 1.0%, petrolatum 2.0%, isopropyl myristate 4.0%, propylparaben 0.1%, dimethicone 0.5%;

polyacrylate filler 0.2%;

B is triethanolamine 3.2%, glycerin 5.0%, methylparaben 0.2%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

12. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 12.0%, cetyl alcohol 2.5%, petrolatum 3.0%, isopropyl myristate 1.0%, acetylated lanolin alcohol 1.0%, glyceryl monostearate 5.0%, propylparaben 0.1%;

B is glycerin 5.0%, methylparaben 0.2%, triethanolamine 2.5%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

13. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 5.0%, cetyl alcohol 2.0%, ethoxylated stearyl alcohol and stearyl alcohol blend 2.0%, petrolatum 4.0%, lanolin oil 0.5%, acetylated lanolin alcohol 1.0%, propylene glycol 1.0%, propylparaben 0.1%;

polyacrylate thickener 0.1%;

B is triethanolamine 2.0%, methylparaben 0.2%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

14. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 16.0%, cetyl alcohol 2.5%, petrolatum 4.0%, glyceryl monostearate 6.0%, dimethicone 5.0%, stearic acid 2.0%, propylparaben 0.1%;

B is triethanolamine 2.0%, glycerin 5.0%, methylparaben 0.2%; and

purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

15. The improved skin care formulation of claim 1 comprising an oil phase, "A," and water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 4.0%, mineral oil 4.5%, petrolatum 3.0%, stearyl alcohol 2.0%, lanolin oil 2.0%, glyceryl monostearate and PEG 100 stearate blend 15.0%, propylparaben 0.1%;

B is glycerin 2.0%, methylparaben 0.2%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

16. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 16.0%, petrolatum 13.0%, propylene glycol monostearate 4.0%, cetyl alcohol 2.0%, mineral oil 4.0%, stearic acid 3.0%, propylparaben 0.1%;

B is methylparaben 0.2%, triethanolamine 3.0%, glycerin 6.0%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

17. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 12.0%, cetyl alcohol 3.5%, petrolatum 3.0%, isopropyl myristate 1.0%, acetylated lanolin alcohol 1.0%, triethanolamine 2.5%, glyceryl monostearate, SE 5.0%, propylparaben 0.1%;

B is glycerin 5.0%, methylparaben 0.2%, disodium EDTA 0.1%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

18. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 2.0%, cetyl alcohol 2.0%, stearyl alcohol 0.5%, isopropyl myristate 1.0%, propylparaben 0.1%;

B is sodium lauryl sulfate 0.5%, methylparaben 0.2%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

19. The improved skin care formulation of claim 1 comprising an oil phase, "A," and a water phase, "B," as follows:

A is a soybean oil-fumaric acid Diels-Alder adduct 4.0%, mineral oil 4.5%, petrolatum 3.0%, stearyl alcohol 2.0%, cetyl alcohol 1.0%, lanolin oil 2.0%, glyceryl monostearate and PEG 100 stearate blend 15.0%, propylparaben 0.1%;

B is glycerin 2.0%, methylparaben 0.2%; and

fragrance 0.05%, purified water, USP qs

wherein A and B are heated separately to about 70°

-80°

C., A is then added to B with mild agitation and the combined materials are cooled to about 40°

C. at which time the fragrance and water are added and mixing is continued until the product temperature reaches about 35°

C.

20. An improved hair care preparation including as an emollient therefor, vegetable oil adducts, wherein the improvement comprises enhanced softening of hair cuticle provided by adducts prepared from vegetable oils containing non-conjugated polyunsaturated fatty acid esters which are conjugated and elaidinized and then modified via Diels-Alder addition with a member of the group consisting of acrylic acid, fumaric acid or maleic anhydride.

21. The improved hair care preparation of claim 20 wherein the vegetable oil is soybean oil.

22. The improved hair care preparation of claim 20 which also includes as an emollient a member of the group selected from a vegetable oil, a modified vegetable oil produced by disproportionating the oil to conjugate the double bonds in the linoleic and linolenic acid groups present in the oil, and a mixture thereof.

23. The improved hair care preparation of claim 20 wherein the Diels-Alder modification reaction occurs by reacting the vegetable oil with fumaric acid.

24. The improved hair care preparation of claim 20 wherein the vegetable oil adduct has the general formula ##STR3## wherein x and y are integers from 3 to 9, x and y together equal 12, at least one Z is a carboxylic acid group, and any remaining Z is hydrogen, and R₁ and R₂ are saturated/unsaturated hydrocarbon radicals.

25. The improved hair care preparation of claim 20 wherein the vegetable oil adducts are subsequently converted into their soap forms selected from the group consisting of the soluble alkali metal and amine soaps and the insoluble alkaline earth and higher valent metal soaps.

26. The improved hair care preparation of claim 24 wherein each Z is a carboxylic acid group in which all or part of the carboxyl groups may be in the anhydride form.

27. The improved hair care preparation of claim 20 as follows:

denatured alcohol 4.0%, a soybean oil-fumaric acid Diels-Alder adduct 3.0%, dimethicone 5.0%, and isobutane 88.0%.