CA2144912A1 - Glycine-containing reducing solution - Google Patents

Glycine-containing reducing solution

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Publication number
CA2144912A1
CA2144912A1 CA 2144912 CA2144912A CA2144912A1 CA 2144912 A1 CA2144912 A1 CA 2144912A1 CA 2144912 CA2144912 CA 2144912 CA 2144912 A CA2144912 A CA 2144912A CA 2144912 A1 CA2144912 A1 CA 2144912A1
Authority
CA
Canada
Prior art keywords
hair
glycine
reducing
reducing solution
strength
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA 2144912
Other languages
French (fr)
Inventor
Joan M. Bergstrom
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DowBrands Inc
Original Assignee
DowBrands Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by DowBrands Inc filed Critical DowBrands Inc
Publication of CA2144912A1 publication Critical patent/CA2144912A1/en
Abandoned legal-status Critical Current

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Abstract

A glycine-containing reducing solution useful for permanent waving of hair. Glycine in the reducing solution decreases the loss of hair strength normally observed as the result of using reducing solutions in the process of permanent waving of hair.

Description

2tg4912 GLYCINE-CONTAINING REDUCING SOLUTION

The present invention generally relates to the art of permanent waving ("perming") of hair and, more particularly, to novel reducing solutions containing glycine that impart significantly higher retention of tensile strength in hair that has been permed using the reducing solutions of the present invention.
Permanent waving of human hair broadly involves two steps. The first step is a reducing step which involves an application of a reducing solution to hair to chemically break the sulfur to sulfur or disulfide cystine bonds occurring naturally in human hair. The disulfide cystine bonds in human hair maintain the hair shape or configuration. While the disulfide cystine bonds are broken the hair can be rearranged into a different configuration. The second step in the permanent waving of hair is an oxidation step which involves application of an oxidizing agent to restore the disulfide bonds in the new rearranged configuration.
Reducing solutions useful for permanent waving of hair contain a reducing agent. It is the reducing agent that chemically breaks the disulfide bonds in the hair. Examples of reducing agents useful in reducing solutions include cysteamine, esters and salts of thioglycolic acid, cysteine, and thiolactic acid.
Typical examples of reducing agents and reducing 3 solutions are taught in U.S. Patent No. 5,260,054.
The reducing step is generally carried out under alkaline conditions. The rearrangement of the disulfide bonds results from both the mechanical stress put on the hair by mandrels or waving rods and from the 41,382-F -1--- 21119~ ~

action of the alkali. The alkali serves to swell the hair by allowing the dissociated sulfur atoms generated by the breaking of the disulfide bonds, to slip past one another more easily under the stress applied by the rods. Consequently, reducing solutions generally have a pH value above about 8.
Generally, reducing solutions may also contain other ingredients like surfactants, chelating agents, or fragrances. Surfactants useful in reducing solutions may be anionic~ cationic~ or nonionic. Examples of surfactants useful in a reducing solution include Laureth-23, and Poloxomar-188. Examples of chelating agents useful in reducing solutions may include ethylenediaminetetraacetic acid ("EDTA")~ as well as salts and derivatives of EDTA.
Permanent waving can damage the structure of the hair, especially if done frequently. This damage can result in hair that has lost much of its strength, thus becoming brittle and breaking easily.
The present invention is directed to reducing solutions containing glycine that are useful in the permanent waving of hair. It is an object of the present invention to overcome the deficiencies of the prior art mentioned above.
The present invention provides reducing solutions that preserve much of the hair strength that is normally lost as a result of perming hair. The present invention is based on the discovery that the addition of glycine into reducing solutions used in permanent waving of hair results in permed hair having increased strength over hair permed using reducing 41,382-F -2-- 214~912 solutions not containing glycine. Generally, reducing solutions of the present invention contain at least about 0.5 percent by weight glycine.
Figure l is a graphical representation of hair strength data obtained by measuring the hair strength of a hair fiber before and after the hair fiber was treated with a comparative sample composition.
Figure 2 is a graphical representation of hair strength data obtained by measuring the hair strength of a hair fiber before and after the hair fiber was treated with an embodiment of the present invention.
Figure 3 is a graphical representation of hair strength data obtained by measuring the hair strength of a hair fiber before and after the hair fiber was treated with another embodiment of the present invention.
Figure 4 is a graphical representation of hair strength data obtained by measuring the hair strength of a hair fiber before and after the hair fiber was treated with yet another embodiment of the present invention.
The present invention is directed to reducing solutions containing glycine.
Generally, the reducing solutions of the present invention contain a functional amount of reducing agent and sufficient alkali to give the reducing solution a pH above about 8. Most preferably, the reducing solutions of the present invention have a pH of from 8.5 to 9Ø A functional amount of reducing agent is any amount that allows the reducing solution to be used effectively in the permanent waving of human hair. These amounts may vary depending on the type of 41,382-F -3-21~912 -reducing agent used. The types and amounts of reducing agents useful in the present invention are generally well known to one of ordinary skill in the art. Most preferably, the reducing agent is cysteamine.
It is believed that the use of cysteamine as the preferred reducing agent in the composition would result in less damage to hair than would the use of thioglycolic acid or the salts of thioglycolic acid.
Cysteamine has a pK2 value of 8.3 and thioglycolic acid and the salts of thioglycolic acid have pK2 values that range from 9.2 to 10.6. The difference in pK2 values indicates that cysteamine would be more fully ionized than thioglycolic acid or the salts of thioglycolic acid at a given pH above pH 8.0 and less than 9Ø It is believed that the more fully ionized cysteamine (pH 8 to 9) forms and association complex with glycine (pK2 =
9.6) that thioglycolic acid or the salts of thioglycolic acid cannot form in the same pH range. Since cysteamine forms a complex with glycine, there is less free cysteamine to react with the disulfide bonds of hair, causing less damage to hair than free thioglycolic acid or salts of thioglycolic acid.
Other ingredients may be added to reducing solutions of the present invention. These additional ingredients may include, for example, surfactants, chelating agents, and fragrances.
Hair treated with reducing solutions of the present invention maintain greater strength than hair treated with similar reducing solutions but containing no glycine. The following amino acids have been tested, but do not appear to impart increased hair strength as does glycine: lactic acid, alanine, glulamine, succinic 41,382-F _4-- 214~912 acid, glycolic acid, serine, lysine, asparagine, and adipic acids.
Generally, the reducing solutions of the present invention contain at least about 0.5 percent by weight glycine. Increasing the amount of glycine in a reducing solution of the present invention results in increased hair strength. However, higher amounts of glycine in some embodiments may result in some loss of curl efficiency. Consequently, lower amounts of glycine can be used to impart sufficient hair strength without compromising curl efficiency. Preferably, the reducing solutions of the present invention contain from 0.5 percent by weight to lO percent by weight glycine. Most preferably~ the reducing solutions of the present invention contain from 0.5 percent by weight to 5 percent by weight glycine.
The method of making the reducing solutions of the present invention is not critical. Methods for making reducing solutions are well known in the art and the addition of glycine to reducing solutions is easily accomplished by anyone with ordinary skill in the art.

Example l Table I shows the composition of one example of an embodiment of the present invention ("Example l") as well as a comparative sample ("Comparative Sample l").
3o 41,382-F -5-TABLE I

Percent by Weight Ingredient Example 1 Comparative Deionized Water 70.96 75.36 Cysteamine HCL 11.50 11.50 Aqueous Ammonia (28% active) 5.64 5.64 10 Glycine 4.40 --Versenol 120 (chelating agent) 2.00 2.00 Pluronic F-68 (surfactant) 2.00 2.00 Brij 35 (surfactant) 2.00 2.00 Dequest 2016 (chelating agent) 1.00 1.00 Fragrance 0.50 0.50 The effect these compositions have on hair strength of treated hair was measured using a rhecneter commercially available from Dia-Stron Limited. The rheometer is a miniature tensile tester and is used in applications where information on the elastic properties or tensile strength of small fibers and other materials iS required-The rheometer was used to measure the break load and break strain of untreated hair, hair treated with Comparative Sample 1, and hair treated with Example 1- The break load is the amount of force, in grams of force ("gmf"), required to break a sample. The break load is the percent elongation of a sample at the breaking point. For example, if an initial sample length is 20.0 mm before measuring and the sample broke at 31 mm~ then the sample was elongated 11 mm or 55 41,382-F -6-percent of the initial sample length and the break load is 55 percent.
The results of the rheometer measurements are shown in Table II.

TABLE II

Treatment Break Load Break Strain Composition (gmf) (percent) Untreated 103 60.9 Comparative Sample 1 87 57.5 Treated with Example 1 126.5 65.8 For the untreated hair a break load of 103 gmf and a break strain of 60.9% was measured. For the hair treated with Comparative Sample l a break load of 87 gmf and a break strain of 57.5% was measured. And for the hair treated with Example l a break load of 126.5 gmf and a break strain of 65.8% was measured.
While taking the measurements shown in Table II, each hair sample was broken during the measurement.
Thus, each measurement shown in Table II was taken on a different hair sample.
Examples 2-4 Table III shows four different compositions: a comparative sample ("Comparative Sample 2") and three examples of embodiments of the present invention. The four compositions shown in Table III differ only in the amount of glycine and water contained in each composition.

41,382-F _7_ 214~91~

TABLE III

Percent by Weight Ingredient Compar-ative Example Example Example Sample 2 Deionized Water 77.03 66.53 72.53 67.53 Cysteamine HCL ll.lO ll.lO ll.lO ll.lO
Aqueous Ammonia (28~) 5.87 5.87 5.87 5.87 Pluronic F-68 2.00 2.00 2.00 2.00 Dequest 2016 2.00 2.00 2.00 2.00 Isoascorbic Acid 2.00 2.00 2.00 2.00 Glycine 0.0 0.5 5.0 lO.0 The tensile strength of hair treated with each of the compositions shown in Table III was measured on the rheometer by the 20% method. In the 20% method, single fibers of hair were mounted and stretched on the rheometer to measure the force required to extend the hair 20% of its original length. Tensile strength (i.e., hair strength) is measured on the rheometer as work expended in extending the sample. A higher measured rheometer value indicates higher hair strength.
This 20% method allows the hair strength to be measured without breaking the hair. Thus, the same hair fiber can then be treated and re-measured on the 3 rheometer to determine the effect of the treatment on hair strength.
Each of the four compositions shown in Table III was tested using the 20% method to determine the effect each composition has on the strength of hair 41,382-F -8-- 214491~
g treated with the composition. For this test, hair samples were soaked in tap water 24 hours prior to the initial (baseline) measurement on the rheometer. After the baseline measurement, each hair sample was removed from the rheometer and placed in an individual glass vial filled with tap water until the time of treatment.
The samples were allowed to stand for a minimum of 24 hours to allow the hair to return to its original shape.
Next, each hair sample was treated with one of the four compositions of Table III. The treatment process took place for 20 minutes at room temperature in a bag. Each hair fiber was then neutralized with 2.0%
H22 in water.
The treated hair was then placed in a weighing dish filled with tap water until the time it was re-measured on the rheometer. The treated hair was then mounted on the rheometer and measured. All hair fiber samples tested were blond hair.
The results of the test using this 20% method are shown in Table IV. These results are also graphed in Figures l-4.

3o 41,382-F _g_ 214491~

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C-4 1, 382 - 1 0 -` 2144312 .

, 1 For each of the four samples, the rheometer measurement for the treated hair was subtracted from the rheometer measurement for the untreated hair. This difference between the measured value for the untreated hair and the measured value for the treated hair indicates loss of hair strength due to the treatment of the hair fibers. The average of these differences was computed for the ten hair fibers for each of the four samples. The results of these computations are shown in Table V.
TABLE V
Average Strength Loss (Untreated - Treated) Composition Loss Comparative Sample 2 0.581 Example 2 0.495 Example 3 0.435 Example 4 0.214 As shown in Table IV, Table V, and in Figures 1-4, for each of the compositions tested, the treated hair lost some strength versus the untreated hair.
However, hair treated with compositions containing higher amounts of glycine lost less strength, on average, than hair treated with the compositions containing lesser amounts of glycine.
Table VI shows the composition of a particularly preferred embodiment of the present invention ("Example 5").

41,382-F -11-_ 2144912 TABLE VI

. Percent by Ingredlent Weight Deionized Water 73.99 Cysteamine HCL 11.36 Aqueous Ammonia (28X active) 3.65 Brij 35 (surfactant) 2.50 Dequest 2016 (chelating agent)2.00 Pluronic F-68 (surfactant) 2.00 Glycine 2.00 Isoascorbic Acid 2.00 Belmay 3069-3725V (fragrance) 0.50 Example 5 Example 5 was prepared according to the follwing procedure:
l. The total amount of water was added to beaker.
2. Pluronic F-68 was added to water in beaker.
Mix until completely dissolved.
3. Dequest 2016 was added to batch. The batch was mixed until completely dissolved.
4. Glycine was added to the batch. The batch was mixed until completely dissolved.
5. Mixing speed was reduced and Aqua Ammonia (28%) was added to the batch. The remainder of the batch was mixed continously at slow speed.

41,382-F -12-~ 2144912 6. Cysteamine HCL was added to the batch. The batch was mixed until completely dissolved.
7. Isoascorbic acid was added to batch. The batch was mixed until completely dissolved.
8. The Brij 35 was weighed into a small beaker and melted on a hot plate. The beaker of liquid Brij 35 was removed from the hot plate and the Belmay 3069-3725V fragrance was added to it while mixing. The fragrance/Brij 35 mixture was added to the batch. The batch was mixed until completely solubilized.
Note: Solution will be clear after the addition of all ingredients and after thorough mixing.

3o 41,382-F -13-

Claims (6)

1. A reducing solution useful in permanent waving of hair, comprising:
a) a functional amount of reducing agent;
b) sufficient alkali to give the reducing solution a pH above about 8; and c) at least about 0.5 weight percent glycine based on the weight of the reducing solution.
2. A reducing solution according to Claim 1, wherein the glycine is present in an amount from 0.5 weight percent to 10 weight percent of the reducing solution.
3. A reducing solution according to Claim 1, wherein the glycine is present in an amount from 0.5 weight percent to 5 weight percent of the reducing solution.
4. A reducing solution according to Claim 1, wherein the reducing agent is Cysteamine.
5. A reducing solution according to Claim 1, wherein the reducing solution further comprises a surfactant.
6. A reducing solution according to Claim 1, wherein the reducing solution further comprises a chelating agent.
CA 2144912 1994-03-18 1995-03-17 Glycine-containing reducing solution Abandoned CA2144912A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US21080494A 1994-03-18 1994-03-18
US08/210,804 1994-03-18

Publications (1)

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CA2144912A1 true CA2144912A1 (en) 1995-09-19

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Family Applications (1)

Application Number Title Priority Date Filing Date
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5589163A (en) * 1994-02-09 1996-12-31 Helene Curtis, Inc. Permanent wave composition and method
WO2018146054A1 (en) * 2017-02-13 2018-08-16 Unilever Plc Method of strengthening hair
WO2018146051A1 (en) * 2017-02-13 2018-08-16 Unilever Plc Method of strengthening oxidatively-treated hair

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5589163A (en) * 1994-02-09 1996-12-31 Helene Curtis, Inc. Permanent wave composition and method
WO2018146054A1 (en) * 2017-02-13 2018-08-16 Unilever Plc Method of strengthening hair
WO2018146051A1 (en) * 2017-02-13 2018-08-16 Unilever Plc Method of strengthening oxidatively-treated hair
EA038207B1 (en) * 2017-02-13 2021-07-23 ЮНИЛЕВЕР АйПи ХОЛДИНГС Б.В. Method of strengthening hair
EA038216B1 (en) * 2017-02-13 2021-07-26 ЮНИЛЕВЕР АйПи ХОЛДИНГС Б.В. Method of strengthening oxidatively-treated hair
US11219589B2 (en) 2017-02-13 2022-01-11 Conopco, Inc Method of strengthening oxidatively-treated hair

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