KR20140102138A - Composition of Flavor In Oral Care Products - Google Patents

Abstract

The present invention relates to an oral flavor composition including one or more cooling agents selected from a group consisting of (N-etoxycarbonylmethyl)-p-menthane-3-carboxamide (WS-5), N-(4-mentoxyphenyl)-p-menthanecarboxamide(presscholate SC1), N-ehtyl-p-menthane-3-carboxamide (WS-3), N,2,3-trimethyl-2-isopropyl buthaneamide (WS-23), menthone glycerin acethal(presscholate MGA), menthyl ractate(presscholate ML), monomenthyl succinate, and (1R, 3R, 4S)-3-methyl 3,6-dioxaheptanoate. The oral flavor composition of the present invention can not only enhance freshness and sustain enhanced freshness, but also lower a sense of irritation.

Description

[0001] Composition of Flavor In Oral Care Products [

The present invention relates to an oral flavoring composition capable of promoting freshness, which is the most important sensory quality in oral care products.

A study of the refreshing cooling agent has been actively carried out since the development of WS-3 (USP 4,178,459) by Wilkinson Sword in the 1970s and has already been developed and marketed by many perfume companies, have.

Recently, a method of enhancing the effect of applying a refreshing enhancer has been studied, and it has been tried to improve the freshness by using Phenji's press collate MGA + menthol and / or WS-3 and / or WS-23 and the like (Enhanced cooling properties, US 5,451,404 (1995)), Wigley's WS-3, WS-23, ML, MGA and menthyl succinate are used to improve the refreshing properties of chewing gum. (Chewing gum: mixing at least two physiological cooling agents with a release modification material, WO 99/12734 to Wrigley.)

Meanwhile, l-menthol (l-menthol) is widely used as a fragrance for refreshing feeling of coolness and chilly and refreshing feeling in human skin, mouth, nose and throat, Has come. However, l-menthol has insufficient persistence of cold feeling effect, has a problem of irritation, and has a disadvantage of increasing the amount of its use to enhance cold feeling but accompanied by bad bitterness.

It has been reported that simple mixing of refreshing agents or mixing of conventionally used el-menthol and refreshing enhancer has been reported. However, further research is needed to solve the problems of stimulant of el-menthol while improving and maintaining freshness.

U.S. Patent No. 5,451,404

Accordingly, the present inventors intend to provide an oral flavoring composition which can further improve the refreshing effect and lower the irritation to el-menthol.

In order to achieve the above object, the present inventors have studied an oral flavor composition which can enhance freshness and maintain the enhanced freshness while at the same time reducing the irritation of el-menthol. As a result, an optimum composition capable of promoting and sustaining refreshing properties was identified and the present invention was completed.

The present invention relates to a pharmaceutical composition comprising (N-ethoxycarbonylmethyl) -p-menthane-3-carboxamide (WS-5), N- (4-menthoxyphenyl) (WS-3), N, 2,3-trimethyl-2-isopropylbutanamide (WS-23), menthone glycerin acetal (press collate MGA), mental rock An oral cavity comprising at least one cooling agent selected from the group consisting of Tate (press collate ML), monomentyl succinate and (1R, 3R, 4S) -3-methyl 3,6-dioxaheptanoate. To provide a flavor composition.

In the present invention, the oral flavor composition refers to a composition containing a perfume material, a refreshing agent, and the like, which is used to add good fragrance and freshness to mouth care products including toothpaste, toothpaste and the like. The mouthwash compositions may further comprise a solvent, such as glycerin or propylene glycol, for dissolving them, in addition to flavor and sweetness enhancer.

In the present invention, the perfume or fragrance material is a substance used to add flavor and refreshing to the oral care product. The types of tablets used in oral care products are well known and include, for example, el-menthol, peppermint, spearmint, anethole or eucalyptol. Of these, the most effective ingredient in the freshness and irritation of oral care products is L-menthol.

In the present invention, the refreshing enhancer means a substance included in the oral flavor composition in order to improve the strength and duration of refreshing.

In one embodiment of the invention, the oral flavor composition may further comprise ethanol. By further containing ethanol, the mouthfeel composition of the present invention is more excellent in improving the freshness, has a longer lasting freshness, and has the advantage of lowering the irritation of el-menthol.

In one embodiment of the invention, the oral flavor composition is selected from the group consisting of N-ethyl-p-menthane-3-carboxamide (WS-3), N- (4-menthoxyphenyl) Cholate SC1) and ethanol. In the case of the oral flavoring composition of the above composition, the effect of enhancing freshness, sustaining freshness and reducing irritation is particularly excellent.

In one embodiment of the invention, the oral flavor composition is selected from the group consisting of N-ethyl-p-menthane-3-carboxamide (WS-3), (N- ethoxycarbonylmethyl) (WS-5), N- (4-menthoxyphenyl) -p-menthanecarboxamide (press collate SC1) and ethanol.

In another embodiment of the present invention, the oral flavor composition is selected from the group consisting of N-ethyl-p-menthane-3-carboxamide (WS-3), N- (4-menthoxyphenyl) Presskolate SC1), monomentyl succinate and ethanol.

In another embodiment of the invention, the oral flavor composition is selected from the group consisting of N-ethyl-p-menthane-3-carboxamide (WS-3), menthyl lactate (press collate ML) Phenyl) -p-methanecarboxamide (Press Collate SC1) and ethanol.

When the oral flavoring composition has the above composition, the effect of improving the freshness and reducing the irritation is particularly excellent.

Generally, the oral flavor composition is included in an amount of 0.1 to 1% by weight of the total ingredients used in oral care products, and in one embodiment of the present invention, the refreshing enhancer is 0.1 to 20% by weight ≪ / RTI > For example, the freshness enhancing agent may be contained in an amount of 0.1 to 18 parts by weight, 0.1 to 16 parts by weight, 0.1 to 14 parts by weight, 0.1 to 12 parts by weight, or 0.1 to 10 parts by weight based on 100 parts by weight of the total oral flavor composition. When the freshness enhancing agent is 0.1 to 20 parts by weight, the freshness enhancing effect is more excellent. On the contrary, when the freshness enhancing agent is less than 0.1 part by weight, the effect of improving the freshness is weak. When the amount is more than 20 parts by weight, it is difficult to realize feeling of use due to an increase in the price of the oral flavoring agent and weakening of the overall flavor.

In one embodiment of the present invention, when the oral flavor composition contains ethanol, the ethanol may be included in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavor composition. For example, ethanol may be included in an amount of 0.1 to 18 parts by weight, 0.1 to 16 parts by weight, 0.1 to 14 parts by weight, 0.1 to 12 parts by weight, or 0.1 to 10 parts by weight, relative to the total oral flavor composition. When 0.1 to 20 parts by weight of ethanol is contained, it is possible to further improve the refreshing effect, the refreshing effect, and the irritation reducing effect.

The present invention also provides an oral care article comprising the oral flavor composition as described above. Oral care products are products that are used to maintain and / or enhance the cleanliness or freshness of the mouth, or to remove or alleviate bad breath. The oral flavor compositions according to the present invention are suitable for oral use and can be used without limitation in any kind of oral care products. For example, the oral care article can be toothpaste, toothpaste, mouse spray, film-type mouthwash, tablet-type mouthwash or gum.

The dentifrice containing the oral flavor composition according to the present invention and the mouthwash were prepared to evaluate the effect of improving the freshness, sustaining the refreshing effect and stimulating sensation (Test Example 1). The evaluation of freshness and stimuli was excellent in taste and olfactory function. The panel was selected and the degree of freshness felt over time from the time of brushing was analyzed. As a result, it was confirmed that the oral flavor composition according to the present invention improved refreshing, sustained freshness, and lowered stimulus intensity.

The oral flavoring composition of the present invention not only improves freshness, sustains the enhanced freshness, but also reduces irritation.

Hereinafter, the present invention will be described in detail with reference to examples. The following examples illustrate the invention and are not intended to limit the scope of the invention. These embodiments are provided so that the disclosure of the present invention is not limited thereto and that those skilled in the art will fully understand the scope of the present invention and that the present invention is not limited by the scope of the claims Only.

[Preparation Example 1] Preparation of oral flavor composition

The most important factor in refreshing the oral care composition of mouth care products is l-menthol, which is different in freshness depending on the content of el-menthol. Therefore, the present invention minimizes the experimental error by preparing the oral flavoring composition under the same conditions containing about 50% of el-menthol.

Specific experimental examples are shown in Tables 1 and 2 below.

(Based on 100 g,%, w / w) Raw material name Experimental Example 1 Experimental Example 2 Experimental Example 3 Experimental Example 4 Experimental Example 5 Experimental Example 6 Experimental Example 7 Peppermint oil 20.0 20.0 20.0 20.0 20.0 20.0 20.0 Spearmint Oil 5.0 5.0 5.0 5.0 5.0 5.0 5.0 El-menthol 50.0 50.0 50.0 50.0 50.0 50.0 50.0 Anethole 10.0 10.0 10.0 10.0 10.0 10.0 10.0 Eucalyptol 5.0 5.0 5.0 5.0 5.0 5.0 5.0 WS-3 10.0 4.5 6.0 7.0 WS-5 1.0 2.5 2.0 WS-23 3.0 Press Collate MGA Press Collate ML 1.0 Press Collate SC-1 0.5 1.0 Monomentyl succinate 5.0 1.0 (1R, 3R, 4S) -3-menthyl 3,6-dioxaheptanoate 6.0 ethanol 4.0 2.5 2.0 1.0 Propylene glycol 10.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0 100.0

(Based on 100 g,%, w / w) Raw material name Experimental Example 8 Experimental Example 9 Experimental Example 10 Experimental Example 11 Experimental Example 12 Experimental Example 13 Peppermint oil 20.0 20.0 20.0 20.0 20.0 20.0 Spearmint Oil 5.0 5.0 5.0 5.0 5.0 5.0 l-menthol 50.0 50.0 50.0 50.0 50.0 50.0 Anethole 10.0 10.0 10.0 10.0 10.0 10.0 Eucalyptol 5.0 5.0 5.0 5.0 5.0 5.0 WS-3 6.0 5.0 WS-5 2.0 6.0 1.5 WS-23 2.5 6.0 Press Collate MGA 6.0 2.0 Press Collate ML 7.0 2.0 3.0 Press Collate SC-1 0.5 Monomentyl succinate 3.0 (1R, 3R, 4S) -3-menthyl 3,6-dioxaheptanoate 4.0 ethanol 1.5 Propylene glycol 2.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0

Toothpastes were prepared according to the following method using the oral flavor compositions having the compositions according to Tables 1 and 2 above.

① Measure each component according to the above contents, mix and stir until completely dissolved.

(2) A toothpaste product is prepared by adding 1% by weight of the oral flavor composition to the toothpaste base.

[Test Example 1] Evaluation of freshness and irritability

Test Example  1-1. Freshness evaluation

In order to evaluate the degree of enhancement of freshness designed in the present invention, a panel composed of 30 persons having excellent taste and olfactory functions was constituted, and an inhalant toothpaste product and a mouthwash solution for the oral flavor composition of the experiment example shown in Table 1 were prepared, The intensity of freshness was evaluated on a scale of 15 points.

The inversion rate of the toothpaste product was 1.0 wt% and the inversion rate of the toothpaste was 0.2 wt%.

1) Panel training

For the evaluation of the present invention, twelve panels having excellent taste and olfactory functions were selected and the strength of freshness was evaluated. Prior to evaluating oral care products using the oral flavor compositions according to the present invention, repeated evaluations were performed to reduce the error between the panels and to improve the efficiency of the evaluation.

As a method of evaluation, a 15-point scale was used. The panel was trained by presenting a standard sample in each 3-point scale, and the evaluation was performed 6 times. The final correction was completed through a double blind test .

The composition of the standard sample is shown in Table 3, and the final calibration result is shown in Table 4.

Standard samples (100g,%, w / w) Raw material name Standard 1 Standard 2 Standard 3 Standard 4 Standard 5 Peppermint oil 20.0 20.0 20.0 20.0 20.0 Spearmint Oil 5.0 5.0 5.0 5.0 5.0 l-menthol 40.0 45.0 50.0 55.0 60.0 Anethole 10.0 10.0 10.0 10.0 10.0 Eucalyptol 5.0 5.0 5.0 5.0 5.0 Propylene glycol 20.0 15.0 10.0 5.0 0.0 Sum 100.0 100.0 100.0 100.0 100.0

Panel training results Raw material name Whole El-menthol
(%, w / w) Standard score Final Panel Score Standard deviation (σ) Tolerance range Standard 1 50 3.0 2.89 0.34 3.0 ± 0.34 Standard 2 55 6.0 6.11 0.27 6.0 ± 0.27 Standard 3 60 9.0 8.89 0.30 9.0 ± 0.30 Standard 4 65 12.0 12.10 0.19 12.0 ± 0.19 Standard 5 70 15.0 14.85 0.26 15.0 ± 0.26

2) Freshness evaluation method

2-1) Evaluation of toothpaste

① Squeeze 1.5 g of toothpaste on the same toothbrush.

② Brushing is done by the method used by the panels and fingering is done for about 90 seconds.

③ Gaggle twice at the request of the host.

④ Another 1 minute brushing is done.

⑤ Final gagging is performed and brushing is completed within 20 seconds.

⑥ Evaluate the intensity of freshness immediately after brushing.

⑦ Measure the freshness intensity at 2 minutes, 5 minutes, 10 minutes, 20 minutes and 30 minutes immediately after brushing and evaluate the sustainability of freshness.

2-2) Evaluation of toothpaste

① Submerge 15 ml of the saliva solution into the prepared reagent cup.

② Put the subdivided toothpaste into your mouth and gargle for 20 seconds.

③ Spit out the saliva and repeat the procedure for 5 seconds with 20 ml of purified water and evaluate the intensity of the freshness.

④ Like toothpaste, evaluate the persistence of refreshing at 2, 5, 10, 20, 30 minutes.

3) Freshness evaluation result

A) Improvement of refreshing degree

Evaluation of toothpaste and toothpaste composition prepared using Experimental Example 1-13 showed that the freshness enhancing effect of Experimental Examples 2 to 13 using the freshness enhancing agent was excellent. (p < 0.05)

It was also found that the degree of refreshing enhancement was particularly excellent in Experimental Examples 5, 7, 11, 12 and 13.

Toothpaste and toothpaste showed similar trends.

Evaluation result of improvement of freshness Experimental group toothpaste Toothpaste Experimental Example 1 9.45 ± 0.27 9.75 ± 0.29 Experimental Example 2 9.87 ± 0.25 9.98 ± 0.26 Experimental Example 3 11.51 + - 0.31 11.25 + - 0.21 Experimental Example 4 10.08 + - 0.22 10.24 + 0.24 Experimental Example 5 13.78 ± 0.28 12.48 ± 0.23 Experimental Example 6 10.24 0.30 10.13 ± 0.31 Experimental Example 7 12.96 ± 0.29 12.08 + - 0.33 Experimental Example 8 10.05 + 0.33 10.13 ± 0.27 Experimental Example 9 10.15 ± 0.25 10.01 + - 0.23 Experimental Example 10 10.11 ± 0.24 10.19 ± 0.22 Experimental Example 11 11.89 ± 0.29 11.67 + - 0.25 Experimental Example 12 12.02 + - 0.31 11.87 ± 0.39 Experimental Example 13 13.41 ± 0.31 12.83 + - 0.25

B) freshness sustained intensity

The sustained strength of the freshness was significantly superior to that of Experimental Example 1 in Experimental Examples 2 to 13 using the freshness enhancing agent.

It was also found that the sustained strength of the freshness was particularly excellent in Experimental Examples 5, 7 and 13.

Experimental Example 6 and Experimental Example 9 were obtained by evaluating the sustained strength of freshness with and without ethanol. The initial intensities of freshness were similar, but the persistence of freshness over time was better in Experimental Example 6 including ethanol. (p < 0.05)

Especially, when the time elapsed for more than 30 minutes, when the freshness enhancer of the present invention and ethanol were mixed with each other, the strong refreshing power of about 7 times or more was maintained.

Freshness Continuous strength evaluation result (toothpaste) toothpaste Early 2 minutes 5 minutes 10 minutes 20 minutes 30 minutes Experimental Example 1 9.45 5.51 3.42 2.01 1.09 0.41 Experimental Example 2 9.87 9.88 7.45 6.41 5.55 3.25 Experimental Example 3 11.51 11.02 9.13 7.68 6.01 4.01 Experimental Example 4 10.08 10.56 8.74 6.25 4.77 3.91 Experimental Example 5 13.78 14.03 12.91 12.03 8.52 6.33 Experimental Example 6 10.24 10.36 8.44 6.25 4.57 3.89 Experimental Example 7 12.96 13.23 10.47 7.99 6.41 5.03 Experimental Example 8 10.05 10.23 8.51 6.23 4.44 3.52 Experimental Example 9 10.15 10.24 8.01 5.89 4.08 3.32 Experimental Example 10 10.11 10.56 8.57 6.74 4.86 3.21 Experimental Example 11 11.89 12.1 9.89 7.69 6.12 4.34 Experimental Example 12 12.02 12.48 10.01 7.12 5.92 4.22 Experimental Example 13 13.41 13.89 12.43 10.56 8.84 5.29

Freshness Continuous strength evaluation result (toothpaste) Toothpaste Early 2 minutes 5 minutes 10 minutes 20 minutes 30 minutes Experimental Example 1 9.75 7.01 5.15 1.12 0.85 0.21 Experimental Example 2 9.98 8.59 6.03 4.01 2.99 2.07 Experimental Example 3 11.25 9.99 7.15 4.56 3.12 2.74 Experimental Example 4 10.24 8.74 5.87 3.99 2.15 2.11 Experimental Example 5 12.48 11.05 8.9 7.01 4.98 3.56 Experimental Example 6 10.13 8.34 6.15 4.74 2.91 1.88 Experimental Example 7 12.08 10.87 8.09 6.45 4.12 3.15 Experimental Example 8 10.13 8.71 5.89 4.78 2.91 2.09 Experimental Example 9 10.01 8.41 5.69 4.01 2.59 1.45 Experimental Example 10 10.19 8.74 7.12 5.78 3.26 1.99 Experimental Example 11 11.67 10.77 6.99 5.45 3.78 2.41 Experimental Example 12 11.87 10.45 7.65 6.02 4.07 2.89 Experimental Example 13 12.83 12.11 9.15 7.27 5.33 4.14

Test Example  1-2. Irritability  evaluation

1) Evaluation method of irritability

Strength of stimulation was evaluated in relatively irritating toothpaste depending on use. The evaluation method is as follows.

① Squeeze 1.5 g of toothpaste on the same toothbrush.

② Brushing is done by the method used by the panels and fingering is done for about 90 seconds.

③ Gaggle twice at the request of the host.

④ Another 1 minute brushing is done.

⑤ Final gagging is performed and brushing is completed within 20 seconds.

⑥ Evaluate the intensity of stimulation immediately after brushing and immediately after 5 minutes.

The evaluation is based on a 5-point scale, with 1 score if there is little stimulation and 5 if the stimulus is too severe.

2) Results of stimulus evaluation

The results of the evaluation of the intensity of stimulation are shown in Table 8 below. As a result, in Experimental Examples 3, 5, 6, 7 and 13, the sensation of stimulus was generally evaluated to be low.

The results of Experimental Example 6 and Experimental Example 9 showing the intensity of stimulation for presence or absence of ethanol showed that the degree of stimulation was low at the beginning and after 5 minutes in Experimental Example 6 including ethanol (p <0.05). This suggests that experimental examples including ethanol in particular can show a feeling of better feeling due to the low intensity of stimulation.

Strength evaluation result of stimulus Experimental toothpaste group Immediately after brushing 5 minutes later Experimental Example 1 3.46 ± 0.73 2.88 ± 0.62 Experimental Example 2 3.15 ± 0.67 2.77 + - 0.24 Experimental Example 3 2.98 ± 0.59 2.48 ± 0.44 Experimental Example 4 3.22 ± 0.58 2.86 ± 0.48 Experimental Example 5 2.96 + - 0.62 2.42 ± 0.59 Experimental Example 6 2.97 ± 0.58 2.40 ± 0.48 Experimental Example 7 2.91 + - 0.53 2.48 0.41 Experimental Example 8 3.18 ± 0.72 2.83 ± 0.66 Experimental Example 9 3.41 ± 0.65 2.84 0.63 Experimental Example 10 3.19 ± 0.73 2.66 ± 0.60 Experimental Example 11 3.03 ± 0.97 2.72 ± 0.69 Experimental Example 12 3.12 ± 0.85 2.73 ± 0.69 Experimental Example 13 2.86 ± 0.71 2.44 0.49

Claims (10)

(N-ethoxycarbonylmethyl) -p-menthane-3-carboxamide, N- (4-menthoxyphenyl) -p- , N, 2,3-trimethyl-2-isopropylbutanamide, menthone glycerin acetal, menthyl lactate, monomenthyl succinate and (1R, 3R, 4S) -3-methyl 3,6-dioxaheptanoate &Lt; / RTI &gt; wherein the composition comprises at least one cooling agent selected from the group consisting of: &lt; RTI ID = 0.0 &gt;
The oral flavor composition of claim 1, wherein the oral flavor composition further comprises ethanol.
The oral flavor composition according to claim 2, wherein the oral flavor composition is an oral flavoring composition comprising N-ethyl-p-menthane-3-carboxamide, N- (4-menthoxyphenyl) .
3. The oral flavor composition of claim 2 wherein the oral flavor composition is selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, (N- ethoxycarbonylmethyl) -p- &Lt; / RTI &gt; menthoxy phenyl) -p-methanecampamide and ethanol.
The oral flavor composition of claim 2 wherein the oral flavor composition comprises N-ethyl-p-menthane-3-carboxamide, N- (4-menthoxyphenyl) -p-menthane cyanamide, monomentyl succinate and ethanol &Lt; / RTI &gt;
3. The composition of claim 2, wherein the oral flavor composition is selected from the group consisting of N-ethyl-p-menthane-3-carboxamide, menthyl lactate, N- (4-menthoxyphenyl) &Lt; / RTI &gt;
The oral flavoring composition according to claim 1, wherein the freshness enhancing agent is contained in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavoring composition.
The oral flavoring composition according to claim 2, wherein the ethanol is contained in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavor composition.
9. Oral care article comprising the oral flavor composition of any one of claims 1-8.
10. The oral care article of claim 9, wherein the oral care article is toothpaste, toothpaste, mouse spray, film-type mouthwash, tablet-type mouthwash or gum.