Fatty acid esters of oxalkylated alkylalkylenediamines and salts thereof and compositions for conditioning of hair

Abstract

Hair conditioner compositions comprising an ester of an oxalkylated alkylalkylene diamine of formula (I) ##STR00001##
wherein: R denotes C.sub.8-C.sub.24-alkyl or C.sub.8-C.sub.24-alkenyl A denotes a group —C.sub.2H.sub.4— or —C.sub.3H.sub.6 Z.sup.1 denotes a group —C(O)—R′, wherein R′ denotes C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.2 denotes a group —C(O)—R″, wherein R″ denotes C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.3 denotes a group —C(O)—R′″, wherein R′″ denotes C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.4 denotes a group —C(O)—R″″,
wherein R″″ denotes C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, a denotes 0 or 1, m denotes 2 or 3, and u, v, w and x are each independently numbers from 1 to 9, or the quaternized salts thereof, and comprising at least one alcohol component, having 6 to 18 carbon atoms, lead to improved conditioning and gloss of the hair.

Claims

1. A hair conditioning composition comprising 0.1 to 10% by weight of an oxalkylated alkylalkylene diamine of formula (I) ##STR00011## wherein R is C.sub.8-C.sub.24-alkyl or C.sub.8-C.sub.24-alkenyl A is —C.sub.2H.sub.4— or —C.sub.3H.sub.6—, Z.sup.1 is —C(O)—R′, wherein R′ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.2 is —C(O)—R″, wherein R″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.3 is —C(O)—R′″, wherein R′″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.4 is —C(O)—R″″, wherein R″″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, a is 0 or 1, m is 2 or 3, u, v, x and w are each independently numbers from 1 to 9, where if a=0 the sum of u, v, and w is from 3 to 30, and where if a=1 the sum of u, v, w and x is from 4 to 35, or a quaternized salt thereof, and 0.5 10% by weight of a fatty alcohol component, having 6 to 18 carbon atoms.

2. The hair conditioning composition according to claim 1, comprising an oxalkylated alkylalkylene diamine of formula (I), wherein R is C.sub.8-C.sub.24-alkyl or C.sub.8-C.sub.24-alkenyl A is a group —C.sub.2H.sub.4— Z.sup.1 is —C(O)—R′, wherein R′ is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl Z.sup.2 is —C(O)—R″, wherein R″ is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl Z.sup.3 is —C(O)—R′″, wherein R′″ is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl Z.sup.4 is —C(O)—R″″, wherein R″″ is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl a is 0 m is 3, u, v and w are each independently numbers from 3 to 9, where the sum of u, v and w is from 6 to 30, or a quaternized salt thereof, where the salt is formed by quaternizing one or two of the nitrogen atoms of the compound of formula (I).

3. The hair conditioning composition according to claim 1, comprising an oxalkylated alkylalkylene diamine of formula (I), wherein R is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl A is a group —C.sub.2H.sub.4— Z.sup.1 ,Z.sup.2 ,Z.sup.3 and Z.sup.4 are the same and are —C(O)—R′ with R′ being C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl a is 0, m is 3 u, v, and w are each independently numbers from 3 to 9, where the sum of u, v and w is from 6 to 30, or a quaternized salt thereof, where the salt is formed by quaternizing one or two of the nitrogen atoms of the compound of formula (I).

4. The hair conditioning composition according claim 1, comprising a salt of an ester of an oxalkylated alkylalkylene diamine of formula (I).

5. A method of preparing a hair conditioning composition, comprising the step of mixing an oxalkylated alkylalkylene diamine of formula (I), ##STR00012## wherein R is C.sub.8-C.sub.24-alkyl or C.sub.8-C.sub.24-alkenyl A is —C.sub.2H.sub.4— or —C.sub.3H.sub.6—, Z.sup.1 is —C(O)—R′, wherein R′ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.2 is —C(O)—R″, wherein R″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.3 is —C(O)—R′″, wherein R′″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.4 is —C(O)—R″″, wherein R″″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, a is 0 or 1, m is 2 or 3, u, v, w and x are each independently numbers from 1 to 9, where if a=0, the sum of u, v and w is from 3 to 30, and where if a=1, the sum of u, v, w and x is from 4 to 35, or a quaternized salt thereof, and a fatty alcohol component, having 6 to 18 carbon atoms.

6. A method of conditioning the hair, comprising the steps of applying a hair conditioner composition onto wet hair and removing the conditioner composition from the hair, wherein the hair conditioner composition comprises an ester of an oxalkylated alkylalkylene diamine of formula (I), ##STR00013## wherein R is C.sub.8-C.sub.24-alkyl or C.sub.8-C.sub.24-alkenyl A is —C.sub.2H.sub.4— or —C.sub.3H.sub.6—, Z.sup.1 is —C(O)—R′, wherein R′ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.2 is —C(O)—R″, wherein R″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.3 is —C(O)—R′″, wherein R′″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, Z.sup.4 is —C(O)—R″″, wherein R″″ is C.sub.5-C.sub.35-alkyl or C.sub.5-C.sub.35-alkenyl, a is 0 or 1, m is 2 or 3, u, v, w and x are each independently numbers from 1 to 9, where if a=0, the sum of u, v and w is from 3 to 30, and where if a=1, the sum of u, v, w and x is from 4 to 35, or a quaternized salt thereof, and a fatty alcohol component, having 6 to 18 carbon atoms.

7. The method of conditioning the hair according to claim 6, further comprising the following steps: a) applying a shampoo composition onto the hair; b) washing the hair with the shampoo composition; c) removing the shampoo composition from the hair; prior to applying a hair conditioner composition onto wet hair and removing the conditioner composition from the hair.

8. The method of claim 6, wherein the hair conditioner composition comprises a quaternized salt of an oxalkylated alkylalkylene diamine of formula (I), where the salt is quaternized at one or two of the nitrogen atoms of the compound of formula (I).

9. The method of claim 6, wherein the hair conditioner composition further comprises as a lubricant a fatty alcohol component, having 6 to 18 carbon atoms.

10. The method of claim 6, wherein the hair conditioner composition further comprises a silicone, and a further surfactant.

11. The method of claim 6, wherein the hair conditioner composition further comprises a further surfactant which is selected from the group consisting of non-polymeric, cationic quaternary ammonium compounds.

12. The method of claim 6, wherein the hair conditioner composition is applied to the hair on a weekly to bi-weekly basis following initial treatment of the hair with a shampoo composition.

13. The hair conditioner composition according to claim 1, wherein at least one of Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl.

14. The hair conditioner composition according to claim 1, wherein the quaternized salt is formed by using an alkylating agent selected from the group consisting of dimethyl sulfate, diethyl sulfate, dimethyl carbonate, diethyl carbonate, methyl chloride, ethyl chloride, methyl bromide, ethyl bromide, methyl iodide, and ethyl iodide.

15. The method of claim 6, wherein the hair conditioner composition further comprises cetyl trimethylammonium chloride.

16. The hair conditioning composition according to claim 1, comprising an oxalkylated alkylalkylene diamine of formula (I), wherein the oxalkylated alkylalkylene diamine of formula (I) is a quaternized salt.

Description

EXAMPLE 1

Preparation of a Salt with Two Quaternized N-atoms

(1) The following compound 13-SK009 was prepared as following:

(2) ##STR00007##
509.2 g (0.250 mol) of a compound with the formula (I) with R=C-Chain derived from tallow fatty acid (C16/C18), a=0, m=3, A=—C.sub.2H.sub.4—, u+v+w=23, Z.sup.2=Z.sup.3=Z.sup.4=C-Chain derived from cocos fatty acid (C12/C14) were initially charged in a 1 L-flask equipped with a reflux condenser and a thermometer and heated to 60° C.

(3) While stirring, 62.4 g (0.495 mol) dimethyl sulfate were added dropwise within 30 minutes. During that period, the temperature raised to 80° C. The reaction mixture was stirred for 5 h at 80° C. After cooling to room temperature, 530 g product (salt with two quaternized N-atoms) were obtained (Bas.N<0.1%) as clear yellow-brown liquid. The group “Me” in the above formula denotes a methyl group.

EXAMPLE 2

Preparation of a Salt with (on Average) One Quarternized N-atom

(4) The following compound 13-CK068 (mixture) was prepared as following:

(5) ##STR00008##
203.7 g (0.1 mol) of a compound with the formula (I) with R=C-Chain derived from tallow fatty acid (C16/C18), a=0, m=3, A=—C.sub.2H.sub.4—, u+v+w=23, Z.sup.2=Z.sup.3=Z.sup.4=C-Chain derived from cocos fatty acid (C12/C14) were initially charged in a 1 L-flask equipped with a reflux condenser and a thermometer and heated to 60° C.

(6) While stirring, 12.3 g (0.1 mol) dimethyl sulfate were added drop wise within 30 minutes. During that period, the temperature raised to 80° C. The reaction mixture was stirred for 5 h at 80° C. After cooling to room temperature, 207.6 g product were obtained (Bas.N=0.67%) as clear yellow-brown liquid.

EXAMPLE 3

Preparation of a Salt with Two Quaternized N Atoms

(7) The following compound (14-CK050) was prepared corresponding to the method of Example 1:

(8) ##STR00009##
n=2.5; 2CH.sub.3SO.sub.4.sup.31 ; R=C-chain derived from tallow fatty acid (C.sub.16/C.sub.18), a=0, m=3, A=—C.sub.2H.sub.4—, u+v+w=7.5, Z.sup.2=Z.sup.3=Z.sup.4=C-chain derived from caprylic acid (C.sub.8)

EXAMPLE 4

Preparation of a Salt with Two Quaternized N Atoms

(9) The following compound (14-CK097) was prepared corresponding to the method of Example 1:

(10) ##STR00010##
n=5.00; 2CH.sub.3SO.sub.4.sup.−; R=C-chain derived from tallow fatty acid (C.sub.16/C.sub.18), a=0, m=3, A=—C.sub.2H.sub.4—, u+v+w=15, Z.sup.2=Z.sup.3=Z.sup.4=C-chain derived from stearic acid (C.sub.18)

EXAMPLES 5 to 9

Preparation of Conditioner Compositions

(11) The hair conditioner compositions (E5 to E9) were prepared by mixing the following components (Table 1).

(12) TABLE-US-00001 TABLE 1 Composition of hair conditioners containing molecules of Examples 1 to 4. Silicone New Cetearyl DC Formulation/ New component CTAC alcohol PMX 200 Example component (%) (%) (%) (%) Example 5 13-SK009 2.0 0 4.00 0.2 (Example 1) Example 6 13-CK068 2.0 0 4.00 0.2 (Example 2) Example 7 14-CK050 1.8 0.2 4.0 0.2 (Example 3) Example 8 14-CK097 1.8 0.2 4.0 0.2 (Example 4) Example 9 14-CK097 2.0 0 4.0 0.2 (Example 4)

(13) All % are based on the weight of the composition.

(14) For all samples, pH of the water based compositions was adjusted between 3.5 and 5.

EXAMPLE 10

Use of the Conditioner Composition

(15) The studies were conducted with hair swatches (using dark brown, straight European hair tresses, 12 cm long, and 4 h bleached European hair, 12 cm long, both from Kerling, Germany).

(16) These hair swatches were pre-treated (base wash with a 14% by weight sodium lauryl ether sulfate (SLES) solution) and then treated with a classical, silicone-free shampoo composition, and then with one of the conditioner compositions E5 to E9, according to the steps: a) applying the shampoo composition onto the hair; b) washing the hair with the shampoo composition; c) removing the shampoo composition from the hair; d) applying the conditioner composition of Examples 5 to 9 onto the hair; e) removing said conditioner composition from the hair.

(17) During rinsing the conditioner, for all examples E5 to E9, hair became detangled, had a smooth feel under running water and a pleasant tactile profile. Wet hair was tested for combing force (using an MTT175 tensile tester from Diastron, UK). Afterwards, the swatches were left to dry hanging in air at room temperature. The dry hair after all treatments with conditioner compositions E5 to E9 also showed good tactile results and led to nice hair appearance.

(18) After the use of the hair conditioning system, comprising a pre-treatment with shampoo and a conditioner treatment, the hair probes were tested for hair shine (using a Samba Hair System, from Bossa Nova Tech) and dry combing force (using an MTT175 tensile tester from Diastron, UK).

(19) Regarding hair shine, this measurement technique allows for quantitative evaluation of the light intensity reflected from hair swatches mounted on a drum in a half-circle arrangement. The technique selectively analyzes the following components: First reflection (SHINE): from the surface of the fibers, creates a shine band on hair Second reflection (CHROMA): reflection of the transmitted light off the bottom surface of the fibers—creates a band carrying color information specific to the fiber DIFFUSED LIGHT results from the internal scattering, and corresponds to ‘bulk hair’ shine and color intensity.

(20) Conventionally, maximum values of each peak are compared for samples treated with different materials.

(21) Combing results and hair shine data for hair treated with the conditioners of Examples 5 to 9 are summarized in Table 2. As references, conditioners containing CTAC at 2% (active level) or BTAC at 2% (active level) were used, with the same levels of cetearyl alcohol (4% active) and 0.2% silicone oil (Dow Corning PMX 200).

(22) TABLE-US-00002 TABLE 2 Performance results of hair conditioners of Examples 5 to 9. wet wet combing dry combing force, dry combing force, virgin bleached combing force, hair shine, hair hair force, virgin bleached virgin hair, (average), (average), hair hair BossaNovaluster Conditioner gmf gmf (max), gmf (max), gmf values CTAC 2% — 12.1 140.8 117.2 15.5 BTAC 2% 10.7 — — — — Example 5 — — 92.9 28.7 16.0 Example 6 — — 65.2 28.8 16.6 Example 7 8.8 11.9 — 58.7 16.3 Example 8 9.7 — — 43.0 17.5 Example 9 10.2 — — 66.9 16.1

(23) It is seen from the data of Table 2 that the use of the new compositions described here significantly improves the properties of hair conditioner products. In particular, the lowering of wet and dry combing force has been observed for both virgin and bleached (damaged) hair, in comparison to typical market benchmarks. For consumers, this corresponds to easier combing, less tangling and better alignment of hair, which further leads to easier styling. Additionally, hair shine has been improved by applying a composition comprising an oxalkylated alkylalkylene diamine of formula (I).