JP2005515272A - Imidazo Link at - Google Patents

Abstract

Provided is a mixture of dialkyl imidazoline ats with a specified substituent content. In one embodiment, at least a portion of the mixture comprises at least one dialkyl imidazoline att having at least one C _16- C ₃₀ alkyl group, and the C _16- C ₃₀ substituent content of the mixture is C ₁₀₊ based substitution About 10% to about 95% with respect to the base range.
Imidazoline at and quat mixtures, methods for producing personal care products and cosmetics and formulations containing imidazoline at and quat mixtures, methods for producing such personal care products and cosmetics and formulations, and such imidazo Also provided are methods of using link at, quat blends, personal care products and cosmetics and formulations. Various embodiments are disclosed.

Description

[Cross-reference of related applications]
This patent application is a retrospective application date of US Provisional Patent Application No. 60 / 347,170, filed Jan. 9, 2002, which is hereby incorporated by reference in its entirety. Alleged benefit and retrospective benefit of US Provisional Patent Application No. 60 / 403,037 filed Aug. 13, 2002.

は、当分野において知られている。それらは、例えば米国特許第４，８５１，１４１号、米国特許第４，４５２，７３２号、米国特許第４，２４７，５３８号、米国特許第４，２０６，１９５号、米国特許第４，１８７，２８９号、米国特許第４，１４９，５５１号、および米国特許第４，１０２，７９５号に開示されている。 [Background of the invention]
Compounds containing an imidazoline ring

Are known in the art. They are, for example, US Pat. No. 4,851,141, US Pat. No. 4,452,732, US Pat. No. 4,247,538, US Pat. No. 4,206,195, US Pat. No. 4,187. 289, U.S. Pat. No. 4,149,551, and U.S. Pat. No. 4,102,795.

（式中、Ｒ’およびＲ’’’は１１〜１２個の炭素原子を有するアルキル基、または１３〜２４個の炭素原子を有するβ−ヒドロキシアルキル基であり、Ｒ’’は１〜３個の炭素原子を有する低級アルキル基、ベンジル基、または−（Ｃ₂Ｈ₄Ｏ）_nＨ基（式中、ｎは１〜３である）であり、Ｙ^-はハロゲンまたはモノアルキルスルフェートである）のイミダゾリンを基剤とする第四級化合物（「クアット（quat）」）を含む、繊維または毛髪を柔らかくする組成物を開示している。第’７９５特許は、これらの化合物の混合物の可能性については言及しているが、何らかの特定混合物については記載していない。 U.S. Pat. No. 4,102,795 has the formula

Wherein R ′ and R ′ ″ are alkyl groups having 11 to 12 carbon atoms, or β-hydroxyalkyl groups having 13 to 24 carbon atoms, and R ″ is 1 to 3 A lower alkyl group, a benzyl group, or a — (C ₂ H ₄ O) _n H group (wherein n is 1 to 3), and Y ⁻ is a halogen or a monoalkyl sulfate. ) Imidazoline-based quaternary compounds (“quat”) are disclosed for softening fibers or hair. The '795 patent mentions the possibility of a mixture of these compounds, but does not describe any particular mixture.

（式中、Ｑ’およびＱ’’’基は、１６〜２２個の炭素原子、好ましくは１６〜１８個の炭素原子を含有する炭化水素基であり、Ｑ’’はＣ₁−Ｃ₄アルキルまたはヒドロキシアルキル基であり、Ｙ^-は適合性アニオンである）のイミダゾリンを基剤とする第四級化合物を含む数種の成分を含有するシャンプーを開示している。混合物の可能性は言及されているが、同様に特定化合物は含まれていない。 U.S. Pat. No. 4,452,732 has the formula

Wherein Q ′ and Q ′ ″ groups are hydrocarbon groups containing 16 to 22 carbon atoms, preferably 16 to 18 carbon atoms, and Q ″ is a C ₁ -C ₄ alkyl group. Or shampoos containing several components including quaternary compounds based on imidazolines of the hydroxyalkyl group, Y ^- is a compatible anion). The possibility of a mixture is mentioned but likewise no specific compounds are included.

（式中、Ｔ₁は１２〜１８個の炭素原子を有するアルキル基であり、Ｔ₂は１〜４個の炭素原子を有するアルキレンまたはヒドロキシアルキレン基であり、Ｍは水溶性カチオンである）のイミダゾリンを基剤とする化合物を含む数種の成分を含有する毛髪をシャンプーまたはコンディショニングするための組成物を開示している。第’５３８特許は、これらの化合物の混合物を開示していない。 U.S. Pat. No. 4,247,538 has the formula

Where T ₁ is an alkyl group having 12 to 18 carbon atoms, T ₂ is an alkylene or hydroxyalkylene group having 1 to 4 carbon atoms, and M is a water-soluble cation. Disclosed is a composition for shampooing or conditioning hair containing several components, including imidazoline-based compounds. The '538 patent does not disclose a mixture of these compounds.

In one aspect, the present invention provides a composition comprising a mixture of dialkyl imidazoline atts, where the entire mixture has a defined substituent content. Various embodiments are disclosed. In one embodiment, at least a portion of the mixture comprises at least one dialkyl imidazoline att having at least one C ₁₆ -C ₃₀ alkyl group, and the C _16-30 substituent content of the mixture is a C ₁₀₊ reference substituent. About 10% to about 95% of the range. In another embodiment, at least a portion of the mixture comprises at least one dialkyl imidazolium links at at least one C _20- C ₃₀ alkyl group, C _20-30 substituted group content of the mixture C ₁₀₊ reference substitution About 10% to about 95% relative to the reference substitution range. In another embodiment, at least a portion of the mixture comprises at least one dialkyl imidazolium links at at least one C _20- C ₂₄ alkyl group, C _20-24 substituted group content of the mixture C ₁₀₊ reference substitution About 10% to about 95% with respect to the base range.

  In yet another aspect, the present invention provides a composition comprising a mixture of monoalkyl imidazoline atts, where the entire mixture has a specified substitution content. Various embodiments are disclosed.

  In another aspect, the present invention provides an imidazoline at compound having a certain chemical structure. Various embodiments are disclosed.

  Imidazoline at and quat mixtures, personal care products and cosmetics containing imidazoline at and quat mixtures and methods for producing formulations, methods for producing such personal care products and cosmetics and formulations, such imidazoline Also provided are methods of using at, quat mixtures, personal care products and cosmetics and formulations. Various method embodiments are disclosed.

  For purposes of the present invention, various terms used herein are defined as follows: A “compound” is an individual chemical substance having molecules of the same chemical structure. A “compound” is not a mixture of molecules having different chemical structures. A “composition” may include one compound or a mixture of compounds.

An “alkyl group” is any substituent containing a chain of one or more carbon atoms. An alkyl group may terminate with an alkyl functional group (eg, —CH ₃ ) or a non-alkyl functional group (eg, —Br). Similarly, an alkyl group can be an alkyl functional group (eg, —CH ₂ — in MOL-CH ₂ CH ₃ ) or a non-alkyl functional group (eg, MOL-SO ₂ C) to the rest of the molecule (MOL). It can be bonded through —SO ₂ —) in ₃ H ₈ . For purely exemplary purposes, a — (CH ₂ ) ₃ —OH group, — (CH ₂ ) ₄ —CH ₃ group, —CH ₃ group, and —C (O) — (CH ₂ ) ₅ —CH ₃ group Each is an alkyl group. An “alkyl radical” is a chain of one or more carbon atoms bonded to one another. For purely exemplary purposes, the alkyl groups — (CH ₂ ) ₃ —OH, — (CH ₂ ) ₄ —CH ₃ , and —C (O) — (CH ₂ ) ₅ —CH ₃ are each represented by the structure — (CH _{2) 3 -, - (CH} 2) 4 -CH 3, and - (CH _{2) 5} containing an alkyl radical -CH _3.

The carbon chain of the alkyl group and the alkyl radical, and the alkyl group and the alkyl radical itself are described as “C _x -C _y ”. Alkyl groups containing C _x -C _y alkyl radicals are referred to as C _x -C _y alkyl. Such descriptions include each length of carbon chain containing carbon atoms in the x to y range. For example, descriptions of alkyl radicals “C ₁₀ -C ₂₀ ” include carbon chains having 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 carbon atoms. All alternative carbon chains having 10 to 20 carbon atoms are included.

Throughout this specification, terms such as alkylhydroxy, alkylcarboxy, carboxyalkyl and the like are used. For purely exemplary purposes, an alkyl hydroxy group contains a hydroxy group and an alkyl radical and is bonded to the rest of the molecule through the alkyl radical, and a carboxyalkyl group is a carboxy functional group that connects the alkyl radical and the carboxy group to the rest of the molecule. The alkylcarboxy group is attached to the rest of the molecule through an alkyl radical and terminated with a carboxy functional group. For purely exemplary purposes, “C ₁₀ -C ₃₀ alkyl” defines a range of alkyl groups containing alkyl radicals having 10 to 30 carbon atoms, and “C ₁₀ -C ₃₀ alkyl hydroxy” is hydroxy Define the range of alkyl groups containing groups and alkyl radicals having 10 to 30 carbon atoms.

  In the compounds described herein, and consistent with the definitions provided above, alkyl groups and alkyl radicals, when present, are substituted or unsubstituted, linear or branched, saturated or unsaturated. It's okay. Alkyl groups and alkyl radical substituents described herein, when present, are alkyl radicals having 1 to 8 carbon atoms (eg, methyl, ethyl, n-propyl, i-propyl, and butyl). Halogenated lower alkyl such as trifluoromethyl, perfluoroethyl, chloromethyl, and dichloromethyl; arylalkyl such as benzyl; alkylaryl such as p-methylbenzyl; halo such as fluoro, chloro and bromo; acetoxy and ethylcarboxy; Carboxy such as acetoxymethyl and acetoxyethyl; arylacetoxy such as acetylbenzyl; hydroxy; alkoxy such as methoxy, ethoxy and propoxy; and alkyl such as hydroxymethyl and hydroxyethyl It may include lower alkyl containing Dorokishi.

“Dialkyl imidazoline at” is a compound whose molecule contains one imidazoline ring, one quaternary nitrogen atom, and two alkyl groups (two C ₁₀₊ alkyl groups) having 10 or more carbon atoms. is there. “Monoalkylimidazoline at” is a compound whose molecule contains one imidazoline ring, one quaternary nitrogen atom, and one alkyl group (one C ₁₀₊ alkyl group) having 10 or more carbon atoms. It is.

  In this specification, the mixture of quat compounds will be described in terms of the content of substituents, which is a characteristic of the entire quat mixture. The substituent content of the quat mixture is the ratio of the molar content of the alkyl group contained within the specified substituent range to the molar content of the alkyl group contained within a broader range of reference substituents as a percentage. It is. The molar content values for both the specified substituent range and the reference substituent range are measured for the entire quat mixture.

The specified substituent range is denoted as “C _xy ” which means a range of alkyl groups or alkyl radicals having _{x to y} carbon atoms. The reference substituent range is indicated as “C _XY ” or “C ₁₀₊ ”. “C ₁₀₊ ” means a range of alkyl groups or alkyl radicals having 10 or more carbon atoms. “C _XY ” means a range of alkyl groups or alkyl radicals having X to _Y carbon atoms.

Quat mixtures are described by their “C _xy content” or “C _xy substituent content”. The C ₁₀₊ reference range is the default substituent range. Accordingly, unless otherwise specified, the C _xy substituent content of a quat mixture (abbreviated as “S _xy ” in the mixtures exemplified throughout this specification) is the mole of alkyl groups included within the C _xy range. Ratio _{expressed as} a numerical value of the percentage of the molar content (“M ₁₀₊ ”) of the alkyl group contained in the C ₁₀₊ range (“M _xy ”): S _xy = M _xy / M ₁₀₊ × 100 % ( _Where M _xy and M ₁₀₊ are both measured relative to the entire mixture). When a reference range other than C ₁₀₊ is used to describe the quat mixture (eg, C _XY range), the substituent content of the mixture (“S _{xy / XY} ” in the mixture exemplified throughout this specification) Is a ratio of the molar content of the alkyl group contained within the C _xy prescribed range (“M _xy ”) to the molar content of the alkyl group contained within the C _XY reference range (“M _XY ”): S _{xy / XY} = M _xy / M _XY × 100%.

To illustrate, consider a mixture M1 containing a single molecule of dialkylquat A1 and a different molecule of dialkylimidazoline at A2. By definition, each of the dialkyl quats A1 and A2 has two C ₁₀₊ alkyl groups. Molecules of the quat A1 has one to C ₂₀ alkyl group and one C ₁₂ alkyl group, and the molecule of quats A2 It should be assumed to have two to C ₂₀ alkyl group. Further, the mixture M1 has a C _16-30 substituent content (S _16-30 (M1) such that the specified range is C _16-30 when narrow and the reference range is C ₁₀₊ when wide, for example. )) Can be characterized by.

The C _16-30 substituent content of mixture M1 can be calculated as follows. S _16-30 (M1) = M _16-30 (M1) / M ₁₀₊ (M1) × 100% (where M _16-30 is the C _16-30 mol content of the mixture M1, M ₁₀₊ (M1) is the C ₁₀₊ molar content of mixture M1). Since the molar concentrations of quat A1 and quat A2 in the mixture M1 are the same (one molecule each), the relative molar concentration can be ignored, and instead the absolute number of alkyl groups contained within each range can be used. . Therefore, the C _16-30 substituent content of the entire mixture M1 can be calculated as follows. S _16-30 (M1) = N _16-30 (M1) / N ₁₀₊ (M1) × 100% (where N _16-30 (M1) is in the mixture M1 within the C _16-30 range) The number of alkyl groups, and N ₁₀₊ (M1) is the number of alkyl groups in the mixture M1 within the C ₁₀₊ range).

The first step is to calculate N _16-30 and N ₁₀₊ values for the mixture. To determine N _16-30 and N ₁₀₊ , substituents are counted for all molecules in the mixture as each falls within the C ₁₀₊ and C _16-30 ranges. The same group can be counted twice or more. Since C ₂₀ groups are included in both the C _16-30 range and the C ₁₀₊ range, they must be counted when calculating both N _16-30 (M1) and N ₁₀₊ (M1). However, since the other C ₁₂ group is only contained within the C ₁₀₊ range, it must be counted only when calculating N ₁₀₊ (M1). When a mixture M1 to perform the calculations for the entire, N _16-30 is 3 (2 to C ₂₀ groups of one to C ₂₀ groups and quat A2 of quats A1), N ₁₀₊ 4 (all four radicals Is in the C ₁₀₊ range). For this reason, the S _16-30 for the mixture M1 is 75% (3/4 × 100%).

For more complex quat mixtures, the molar concentration of quat in the mixture is taken into account. One non-limiting example illustrates the calculation of substituent content for a mixture M2 of dialkyl quats A3, A4, and A5. Mixture M2 is characterized by its C _20-30 substituent content (the specified substituent range is C _20-30 and the reference substituent range is C ₁₀₊ ).

The first step for calculating the C _20-30 substituent content (S _20-30 ) of the mixture M2 is to determine the C _20-30 content of each quat molecule based on its chemical structure. . Such substituent content is referred to as C _20-30 "molar content" and denoted as "P _20-30 ". The C _20-30 molar content of quat is determined by dividing the number of C _20-30 alkyl groups (N _20-30 ) in the quat molecule by the number of C ₁₀₊ alkyl groups (N ₁₀₊ ). P _20-30 = N _20-30 / N ₁₀₊ .
In this example, the nature of the substituent for quat in the mixture is described in column (II). The molecule of Quat A3 has one group that falls within the C _20-30 range. The number of groups within the C ₁₀₊ range is 2 for all dialkyl quats. Therefore, the C _20-30 mol content of Quat A3 (P _20-30 (A3)) is 1/2 = 0.5. C _20-30 mole content values for Quat A3, A4, and A5 were calculated in the same way by dividing the numerical value in column (II) by 2 and are shown in column (III).

Next, the C _20-30 molar contribution of each quat component of the mixture (M _20-30 ) is calculated. For this purpose, the C _20-30 molar content of each quat (P _20-30 , column (III)) is multiplied by the number of moles of the corresponding quat in the mixture (M ₀ , column (IV)): M _{20 -30} = P _20-30 × M _0. The calculation results are shown in the column (V). In practice, the product of multiplication is the molar amount of C _20-30 alkyl groups contributed by each quat component of mixture M2.

The total C _20-30 mole content of the mixture M2 (M _20-30 (M2)) is the sum of the C _20-30 mole contributions of the individual quats. M _20-30 (M2) = M _20-30 (A3) + M _20-30 (A4) + M _20-30 (A5). Referring to column (V), quat A3 contributes 1 mole of C _20-30 groups (M _20-30 (A3) = 1) and quat A4 contributes 0.75 moles (M _20-30 ( A4) = 0.75) and Quat A5 contributes 0 moles of C ₂₀ -C ₃₀ groups (M _20-30 (A5) = 0). For this reason, the C _20-30 molar content of the mixture M2 is 1.75 (M _20-30 (M2) = 1 + 0.75 + 0).

The sum of the C ₁₀₊ molar contributions of the individual quats is the total C ₁₀₊ molar content of the mixture M2 (M ₁₀₊ (M2)): M ₁₀₊ (M2) = M ₁₀₊ (A3) + M ₁₀₊ (A4 ) + M ₁₀₊ (A5). Since all dialkyl quats have two alkyl groups within the C ₁₀₊ range, the C ₁₀₊ mole content (M ₁₀₊ ) of the dialkyl quat component is the same as the number of moles of the quat component (M ₀ ). . Referring to column (IV), quat A3 contributes 2 moles of C ₁₀₊ groups (M ₀₊ (A3) = 2) and quat A4 contributes 0.75 moles (M ₀₊ (A4) = 0.75), and Quat A5 contributes 0.75 moles of C ₁₀₊ groups (M ₀₊ (A5) = 0.75). For this reason, the C ₁₀₊ molar content of the mixture M2 is 3.5 (M ₁₀₊ (M2) = 2 + 0.75 + 0.75). Finally, the C _20-30 substituent content of mixture M2 can be calculated as follows: _S20-30 (M2) = _M20-30 (M2) / _M10 + (M2) 1.75 / 3.5 = 50% (column (VI)).

Another non-limiting example illustrates the calculation of substituent content for a mixture of monoalkyl quats. Table 2 shows a mixture M3 of monoalkyl quats B1, B2 and B3. Mixture M3 is characterized by its C _20-24 substituent content (the specified substituent range is C _20-24 and the reference substituent range is C ₁₀₊ ).

Similar to the calculations described with reference to the mixtures in Table 1, the C _20-24 substituent content of the mixture M3 (S _20-24 (M3)) is calculated as follows.

1. The C _20-24 molar content for each monoalkyl _quat is determined. P _20-24 = N _20-24 / N ₁₀₊ . N ₁₀₊ is 1 for all monoalkyl quats, and the C _20-24 mole content for each quat is calculated as follows: P _20-24 = N _20-24 / 1. The calculation results are shown in column (III). It is clear that P _xy = N _xy in general for monoalkyl _quats . Thus, N _xy can be used in place of P _xy , and column (III) is omitted in the latter example of a monoalkylquat mixture.

2. C ₂₀ - to determine the C _20-24 molar contribution of quats component to the number of ₂₄ groups by multiplying the molar quantity of each quats component. M _20-24 = N _20-24 × M ₀ . _Multiply the N _20-24 value in column (II) by the corresponding M ₀ value in column (IV). The calculation results are shown in the column (V).

3. The C _20-24 mole content of mixture M3 is determined by adding the C _20-24 mole contribution of the quat component. M _20-24 (M3) = M _20-24 (B1) + M _20-24 (B2) + M _20-24 (B3). Add the M _20-24 value for each quat component in column (V). The calculated C _20-24 molar content of mixture M3 is also shown in column (V).

4). The C ₁₀₊ mole content of mixture M3 is determined by adding the C ₁₀₊ mole contribution of the quat component. Since all monoalkyl quats have one alkyl group in the C ₁₀₊ range, a molar amount of quat is used. M ₁₀₊ (M3) = M ₀ (B1) + M ₀ (B2) + M ₀ (B3). Add the M ₀ value of each quat component in column (IV). The calculated C ₁₀₊ molar content of mixture M3 is also shown in column (IV).

5. The C _20-24 substituent content of mixture M3 is determined by dividing the C _20-24 mole content of mixture M3 by the C ₁₀₊ mole content of quat in the mixture. S _20-24 (M3) = M _20-24 (M3) / M ₁₀₊ (M3). The calculated C _20-24 substituent content of mixture M3 is also shown in column (VI).

  The above definitions and calculation methods are used throughout to describe various aspects and embodiments of the present invention.

  According to one aspect, the present invention provides a composition comprising a mixture of at least two different dialkyl imidazoline ats. The mixture has a specified substituent content. In addition to the dialkyl imidazoline at, the composition of this aspect of the invention may comprise other quaternary compounds and non-quaternary compounds. If desired, monoalkyl imidazoline at and / or other quaternary compounds are substantially excluded from the composition.

In one embodiment, the mixture includes at least one dialkyl imidazoline at which one or both alkyl groups are C _16-30 alkyl groups. Thus, at least a portion of the mixture has a C ₁₆ -C ₃₀ alkyl group, providing the entire mixture with a C _16-30 substituent content greater than zero. In this embodiment, the C _16-30 substituent content of the mixture is from about 10% to about 95%, more preferably from about 15% to about 80%, even more preferably from about 20% to about 70%, even more preferably Is about 35% to about 60%.

In another embodiment, the mixture comprises at least one dialkyl imidazolium Link @ alkyl groups of one or both are C ₂₀ -C ₃₀ alkyl group. Thus, at least a portion of the mixture has a C ₂₀ -C ₃₀ alkyl group, providing the entire mixture with a C _20-30 substituent content greater than zero. In this embodiment, the C _20-30 substituent content of the mixture is from about 10% to about 95%, more preferably from about 15% to about 80%, even more preferably from about 20% to about 70%, even more preferably Is about 35% to about 60%.

In yet another embodiment, the mixture comprises at least one dialkyl imidazolium Link @ alkyl groups of one or both are C ₂₀ -C ₂₄ alkyl group. Thus, at least a portion of the mixture has a C ₂₀ -C ₂₄ alkyl group, providing the entire mixture with a C _20-24 substituent content greater than zero. In this embodiment, the C _20-24 substituent content of the mixture is from about 10% to about 95%, more preferably from about 15% to about 80%, even more preferably from about 20% to about 70%, even more preferably Is about 35% to about 60%.

（式中、Ｘは塩化物、臭化物、ヨウ化物、フッ化物、硫酸塩、硫酸メチル、硫酸メタンベンジル、リン酸塩、亜硝酸塩、硝酸塩、カルボン酸塩、またはそれらの混合物、好ましくは塩化物または硫酸メチル等の塩形成アニオンであり、ａはＸのイオン電荷であり、
Ｒ¹、Ｒ²、およびＲ³は独立して水素、Ｃ₁−Ｃ₃₀アルキル、Ｃ₁−Ｃ₃₀アルキルヒドロキシ、Ｃ₁−Ｃ₃₀アルキルアミドＲ_(C1-C6)（式中、Ｒ_(C1-C6)はＣ₁−Ｃ₆アルキレンまたはベンジルである）、Ｃ₁−Ｃ₃₀アルキルアリールアミドＲ_(C1-C6)またはＣ₁−Ｃ₃₀アルキルヒドロキシアミドＲ_(C1-C6)であり、
Ｒ¹、Ｒ²、およびＲ³のうちの２つは独立してＣ₁₀−Ｃ₃₀アルキル、Ｃ₁₀−Ｃ₃₀アルキルヒドロキシ、Ｃ₁₀−Ｃ₃₀アルキルアミドＲ_(C1-C6)、Ｃ₁−Ｃ₃₀アルキルアリールアミドＲ_(C1-C6)、またはＣ₁₀−Ｃ₃₀アルキルヒドロキシアミドＲ_(C1-C6)であり、Ｒ¹、Ｒ²、およびＲ³の残りの１つは、水素、Ｃ₁−Ｃ₈アルキル、Ｃ₁−Ｃ₈アルキルヒドロキシ、Ｃ₁−Ｃ₈アルキルアミドＲ_(C1-C6)、Ｃ₁−Ｃ₈アルキルアリールアミドＲ_(C1-C6)、またはＣ₁−Ｃ₈アルキルヒドロキシアミドＲ_(C1-C6)であり、
同一または相違するＲ⁴、Ｒ⁵、Ｒ⁶、およびＲ⁷は、独立して水素、アルキル、アリールアルキル、アルキルアリール、ブロモおよびクロロを含むハロゲン、アセトキシ、アルキルアセトキシ、アリールアセトキシ、カルボキシ、アルキルカルボキシ、ヒドロキシ、またはアルコキシヒドロキシであり、好ましくは同一または相違するＲ⁴、Ｒ⁵、Ｒ⁶、およびＲ⁷は、水素またはＣ₁−Ｃ₈アルキルである）の化合物から選択することができる。 The dialkyl imidazoline at the mixture is of formula (I):

Wherein X is chloride, bromide, iodide, fluoride, sulfate, methyl sulfate, methanebenzyl sulfate, phosphate, nitrite, nitrate, carboxylate, or mixtures thereof, preferably chloride or A salt-forming anion such as methyl sulfate, a is the ionic charge of X,
R ¹ , R ² , and R ³ are independently hydrogen, C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkyl hydroxy, C ₁ -C ₃₀ alkyl amide R _(C1-C6) (wherein R _{(C1 --C6)} is C ₁ -C ₆ alkylene or benzyl), a C ₁ -C ₃₀ alkylaryl amido R _(C1-C6) or C ₁ -C ₃₀ alkyl hydroxyamide R _(C1-C6),
R ^1, R ^2, and two of R ³ is independently C ₁₀ -C ₃₀ alkyl, C ₁₀ -C ₃₀ alkyl hydroxy, C ₁₀ -C ₃₀ alkyl amido _{R (C1-C6), C} 1 - C ₃₀ alkylaryl amide R _(C1-C6), or a C ₁₀ -C ₃₀ alkyl hydroxy amide R _(C1-C6), the remaining one of R ^1, R ^2, and R ³ is hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkyl hydroxy, C ₁ -C ₈ alkyl amido R _(C1-C6), C ₁ -C ₈ alkylaryl amido R _(C1-C6), or C ₁ -C ₈ alkyl hydroxy Amide R _(C1-C6) ,
R ⁴ , R ⁵ , R ⁶ , and R ^{7 which} are the same or different are independently hydrogen, alkyl, arylalkyl, alkylaryl, bromo and chloro containing halogen, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy R ⁴ , R ⁵ , R ⁶ , and R ⁷ are preferably hydrogen or C ₁ -C ₈ alkyl).

More preferably, the dialkylimidazoline at the mixture is of the formula (I) wherein R ¹ is C ₁₀ -C ₃₀ alkyl or C ₁₀ -C ₃₀ alkyl hydroxy and R ² is C ₁ -C ₆ alkyl. in and, R ³ is C ₁₀ -C ₃₀ alkyl amido R _(C1-C6) or C ₁₀ -C ₃₀ alkyl hydroxy amide _{R (C1-C6), R} 4, R 5, R 6, and R ⁷ independently selected from hydrogen or a compound of C ₁ -C ₈ alkyl). Even more preferably, R ¹ is C ₁₀ -C ₃₀ alkyl, R ² is methyl, R ³ is C ₁₀ -C ₃₀ alkylamide C ₁ -C ₃ alkylene or C ₁₀ -C ₃₀ alkylhydroxyamide C an ₁ -C ₃ ^{alkylene, R 4, R 5, R} 6, and R ⁷ are hydrogen, X is chloride or methyl sulfate.

The moiety that provides the mixture with a substituent content greater than C _10+, such as a C _16-30 , C _20-30 or C _20-24 substituent content, is of formula (I) wherein R ¹ is C ₁₆ -C was ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy compound of R ³ is C ₁₀ -C ₃₀ alkyl amido R _(C1-C6)); or the formula (I) (wherein, R ¹ is A compound of C ₁₀ -C ₃₀ alkyl or C ₁₀ -C ₃₀ alkyl hydroxy and R ³ is C ₁₆ -C ₃₀ alkylamide R _(C1-C6) ; or a compound of formula (I) R ¹ and R ³ may both contain compounds within the C _16-30 substituent range. The portions of the mixture may have the same relative variation in the content of the C ₁₆ -C ₃₀ and C ₂₀ -C ₂₄ substituent portions.

Non-limiting examples of dialkyl quats of formula (I) are quats (1), (2), (3), and (4).

In yet another non-limiting example, Table 3 shows a mixture M4 of dialkyl quats (1), (2), (3), and (4) and calculation of substituent content of this mixture. Mixture M4 is characterized by its C _20-30 substituent content (the specified substituent range is C _20-30 and the reference substituent range is C ₁₀₊ ).

（式中、Ｘおよびａは式（Ｉ）を参照して上記で定義したとおりであり、
ｎは１〜３で変動し、好ましくはｎは２であり、
ｍは１または２であり、好ましくはｍは２であり、
同一または相違するＲ⁸およびＲ¹¹はＣ₁₆−Ｃ₃₀アルキルであり、
Ｒ⁹は水素またはＣ₁−Ｃ₃アルキル、好ましくはメチルであり、
Ｒ¹⁰は水素、アルキル、アリールアルキル、アルキルアリール、ブロモおよびクロロを含むハロゲン、アセトキシ、アルキルアセトキシ、アリールアセトキシ、カルボキシ、アルキルカルボキシ、ヒドロキシまたはアルコキシヒドロキシであり、好ましくは水素または低級アルキル、より好ましくは水素である）のジアルキルイミダゾリンクアットの混合物を含む組成物もまた提供する。 The present invention is directed to formula (II):

Wherein X and a are as defined above with reference to formula (I),
n varies from 1 to 3, preferably n is 2.
m is 1 or 2, preferably m is 2,
The same or different R ⁸ and R ¹¹ are C ₁₆ -C ₃₀ alkyl;
R ⁹ is hydrogen or C ₁ -C ₃ alkyl, preferably methyl;
R ¹⁰ is hydrogen, alkyl, arylalkyl, alkylaryl, halogen including bromo and chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy or alkoxyhydroxy, preferably hydrogen or lower alkyl, more preferably Also provided is a composition comprising a mixture of dialkyl imidazoline at (which is hydrogen).

  In addition to the dialkyl imidazoline at of formula (II), the composition of this embodiment may contain other quaternary compounds and non-quaternary compounds. If desired, monoalkyl imidazoline at and / or other quaternary compounds can be substantially excluded from the composition.

In one embodiment, at least one portion of the mixture is of formula (II) wherein one or both of R ⁸ and R ¹¹ is a C ₁₆ -C ₂₄ alkyl group and the mixture's C ₁₆ -C ₂₄ substituent The content is about 10% to about 95%, more preferably about 15% to about 80%, more preferably about 20 to about 80%, even more preferably about 35%, relative to the C _16-30 reference substituent range. At least one quat (which varies from ~ 60%).

In yet another embodiment, at least one portion of the mixture is of formula (II), wherein one or both of R ⁸ and R ¹¹ is a C ₂₀ -C ₂₄ alkyl group, and the C _20-24 substituent of the mixture The content is about 10% to about 95%, more preferably about 15% to about 80%, more preferably about 20 to about 70%, even more preferably about 35%, relative to the C _16-30 reference substituent range. At least one quat (which varies from ~ 60%).

Non-limiting examples of dialkyl imidazoline at of formula (II) are quats (5), (6), (7), and (8).

  Other non-limiting examples of quats of formula (II) are quats (9) to (16) shown in Table 4.

In a non-limiting example, Table 5 shows a mixture M5 of dialkyl quats (9), (10), and (11) and a calculation of the substituent content of this mixture. Mixture M5 is characterized by its C _{20-24 / 16-30} substituent content (the specified substituent range is C _20-24 and the reference range is C _16-30 ). Since R ⁸ and R ¹¹ are C ₁₆ -C ₃₀ alkyl groups, the C _16-30 range was used instead of the default C ₁₀₊ reference range as the reference range. In the calculation, the bond molar content of R ⁸ and R ¹¹ groups in mixture M5 was used.

Other non-limiting examples of quat mixtures and their C _20-24 content calculations are shown in Tables 6 and 7.

（式中、Ｘは塩化物、臭化物、ヨウ化物、フッ化物、硫酸塩、硫酸メチル、硫酸メタンベンジル、リン酸塩、亜硝酸塩、硝酸塩、カルボン酸塩、またはそれらの混合物等の塩形成アニオンであり、
ａはＸのイオン電荷であり、
Ｒ^1a、Ｒ^2a、およびＲ^3aは独立して水素、Ｃ₁−Ｃ₃₆アルキル、Ｃ₁−Ｃ₃₆アルキルヒドロキシ、Ｃ₁−Ｃ₃₆アルキルアミドＲ_(C1-C6)、Ｃ₁−Ｃ₃₆アルキルアリールアミドＲ_(C1-C6)、またはＣ₁−Ｃ₃₆アルキルヒドロキシアミドＲ_(C1-C6)であり、Ｒ_(C1-C6)はＣ₁−Ｃ₆アルキレンまたはベンジルであり、
Ｒ^1a、Ｒ^2a、およびＲ^3aのうちの２つは独立してＣ₁₀−Ｃ₃₆アルキル、Ｃ₁₀−Ｃ₃₆アルキルヒドロキシ、Ｃ₁₀−Ｃ₃₆アルキルアミドＲ_(C1-C6)、Ｃ₁₀−Ｃ₃₆アルキルアリールアミドＲ_(C1-C6)またはＣ₁₀−Ｃ₃₆アルキルヒドロキシアミドＲ_(C1-C6)であり、
Ｒ^1a、Ｒ^2a、およびＲ^3aのうちの残りの１つは、水素、Ｃ₁−Ｃ₈アルキル、Ｃ₁−Ｃ₈アルキルヒドロキシ、Ｃ₁−Ｃ₈アルキルアミドＲ_(C1-C6)、Ｃ₁−Ｃ₈アルキルアリールアミドＲ_(C1-C6)またはＣ₁−Ｃ₈アルキルヒドロキシアミドＲ_(C1-C6)であり、同一または相違するＲ⁴、Ｒ⁵、Ｒ⁶、およびＲ⁷は、独立して水素、アルキル、アリールアルキル、アルキルアリール、フルオロ、ブロモ、クロロ、ヨード、アセトキシ、アルキルアセトキシ、アリールアセトキシ、カルボキシ、アルキルカルボキシ、ヒドロキシ、またはアルコキシヒドロキシである）のジアルキルイミダゾリンクアットを含む組成物であるが、
ただし該ジアルキルイミダゾリンクアットが式

（式中、Ｒ’はＣ₁₁−Ｃ₂₂アルキルまたはＣ₁₃−Ｃ₂₄β−アルキルヒドロキシであり、Ｒ’’はＣ₁−Ｃ₆アルキルであり、Ｒ’’’はＣ₁₂−Ｃ₂₀アルキルまたはＣ_1l−Ｃ₂₂アルキルアミドＣ₁−Ｃ₃アルキレンである）を有していないことを条件とする組成物を提供する。 In another aspect, the invention provides a compound of formula (IA):

Where X is a salt-forming anion such as chloride, bromide, iodide, fluoride, sulfate, methyl sulfate, methanebenzyl sulfate, phosphate, nitrite, nitrate, carboxylate, or mixtures thereof. Yes,
a is the ionic charge of X;
R ^1a , R ^2a , and R ^3a are independently hydrogen, C ₁ -C ₃₆ alkyl, C ₁ -C ₃₆ alkyl hydroxy, C ₁ -C ₃₆ alkyl amide R ₍ C ₁ -C ₆₎ , C ₁ -C ₃₆ alkyl Arylamide R _(C1-C6) or C ₁ -C ₃₆ alkylhydroxyamide R _(C1-C6) , wherein R _(C1-C6) is C ₁ -C ₆ alkylene or benzyl;
Two of R ^1a , R ^2a , and R ^3a are independently C ₁₀ -C ₃₆ alkyl, C ₁₀ -C ₃₆ alkylhydroxy, C ₁₀ -C ₃₆ alkylamide R _(C1-C6) , C _10- C ₃₆ alkylaryl amide R _(C1-C6) or C ₁₀ -C ₃₆ alkyl hydroxy amide R _(C1-C6),
The remaining one of R ^1a , R ^2a , and R ^3a is hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkyl hydroxy, C ₁ -C ₈ alkyl amide R _(C1-C6) , C ₁ -C ₈ alkyl aryl amide R _(C1-C6) or C ₁ -C ₈ alkyl hydroxyamide _{R (C1-C6), R} 4, R 5, R 6, and R ⁷ which are the same or different are independently And a dialkylimidazoline at a hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy, or alkoxyhydroxy) In Although,
Where the dialkyl imidazoline is

Wherein R ′ is C ₁₁ -C ₂₂ alkyl or C ₁₃ -C ₂₄ β-alkylhydroxy, R ″ is C ₁ -C ₆ alkyl, and R ′ ″ is C ₁₂ -C ₂₀ alkyl. Or a C ₁ -C ₂₂ alkylamide C ₁ -C ₃ alkylene).

（式中、ｎは１〜３で変動し、好ましくは、ｎは２であり、
ｍは１または２であり、好ましくは、ｍは２であり、
同一または相違するＲ¹²およびＲ¹⁴はＣ₂₄−Ｃ₃₀アルキルであり、
Ｒ¹³は水素またはＣ₁−Ｃ₃アルキルである）の化合物である。 In one embodiment of this aspect, the dialkyl imidazoline at is of formula (III):

(Wherein n varies from 1 to 3, preferably n is 2;
m is 1 or 2, preferably m is 2.
The same or different R ¹² and R ¹⁴ are C ₂₄ -C ₃₀ alkyl;
R ¹³ is hydrogen or C ₁ -C ₃ alkyl).

  In yet another aspect, the present invention provides a composition comprising a mixture of at least two monoalkyl imidazoline atts with a specified substituent content. In addition to the monoalkyl imidazoline at, the composition of the present invention may contain other quaternary compounds and non-quaternary compounds. If desired, dialkyl imidazoline at and / or other quaternary compounds may be substantially excluded from the composition.

In one embodiment, the mixture contains monoalkyl imidazoline at least one of which has a C ₁₆ -C ₃₀ alkyl group. The C _16-30 substituent content of the mixture is from about 10% to about 95%, preferably from about 15% to about 85%, more preferably from about 20% to about 80%, even more preferably from about 25% to about 75%.

In yet another embodiment, the mixture contains monoalkyl imidazoline at least one of which has a C ₁₈ -C ₂₆ alkyl group. The C _18-26 substituent content of the mixture is from about 10% to about 95%, preferably from about 15% to about 85%, more preferably from about 20% to about 80%, even more preferably from about 25% to about 75%.

In yet another embodiment, the mixture contains monoalkyl imidazoline at least one of which has a C ₂₀ -C ₂₄ alkyl group; the C _20-24 substituent content of the mixture is about 10 % To about 95%, preferably about 15% to about 85%, more preferably about 20% to about 80%, even more preferably about 25% to about 75%.

（式中、Ｘおよびａは式（Ｉ）を参照して定義したとおりであり、
Ｒ¹⁵、Ｒ¹⁶、およびＲ¹⁷は独立して水素、Ｃ₁−Ｃ₃₀アルキル、Ｃ₁−Ｃ₃₀アルキルヒドロキシ、Ｃ₁−Ｃ₃₀アルキルアミドＲ_(C1-C6)、Ｃ₁−Ｃ₃₀アルキルアリールアミドＲ_(C1-C6)、またはＣ₁−Ｃ₃₀アルキルヒドロキシアミドＲ_(C1-C6)であり、Ｒ_(C1-C6)はＣ₁−Ｃ₆アルキレンまたはベンジルであり、
Ｒ¹⁵、Ｒ¹⁶、およびＲ¹⁷の１つはＣ₁−Ｃ₃₀アルキル、Ｃ₁₀−Ｃ₃₀アルキルヒドロキシ、Ｃ₁₀−Ｃ₃₀アルキルアミドＲ_(C1-C6)、Ｃ₁₀−Ｃ₃₀アルキルアリールアミドＲ_(C1-C6)またはＣ₁₀−Ｃ₃₀アルキルヒドロキシアミドＲ_(C1-C6)であり、
Ｒ¹⁵、Ｒ¹⁶、およびＲ¹⁷の残りの２つは、独立して水素、Ｃ₁−Ｃ₈アルキル、Ｃ₁−Ｃ₈アルキルヒドロキシ、Ｃ₁−Ｃ₈アルキルアミドＲ_(C1-C6)、Ｃ₁−Ｃ₈アルキルアリールアミドＲ_(C1-C6)、またはＣ₁−Ｃ₈アルキルヒドロキシアミドＲ_(C1-C6)であり、
同一または相違するＲ¹⁸、Ｒ¹⁹、Ｒ²⁰、およびＲ²¹は独立して水素、アルキル、アリールアルキル、アルキルアリール、ブロモおよびクロロを含むハロゲン、アセトキシ、アルキルアセトキシ、アリールアセトキシ、カルボキシ、アルキルカルボキシ、ヒドロキシ、またはアルコキシヒドロキシであり、好ましくは同一または相違するＲ¹⁸、Ｒ¹⁹、Ｒ²⁰、およびＲ²¹は、水素またはＣ₁−Ｃ₈アルキルである）を有していてよい。 The monoalkyl quat in the mixture is of formula (IV):

Wherein X and a are as defined with reference to formula (I)
R ¹⁵ , R ¹⁶ , and R ¹⁷ are independently hydrogen, C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkyl hydroxy, C ₁ -C ₃₀ alkyl amide R ₍ C ₁ -C ₆₎ , C ₁ -C ₃₀ alkyl Arylamide R _(C1-C6) or C ₁ -C ₃₀ alkylhydroxyamide R _(C1-C6) , wherein R _(C1-C6) is C ₁ -C ₆ alkylene or benzyl;
R ^15, R ^16, and one of R ¹⁷ is C ₁ -C ₃₀ alkyl, C ₁₀ -C ₃₀ alkyl hydroxy, C ₁₀ -C ₃₀ alkyl amido _{R (C1-C6), C} 10 -C 30 alkylaryl amide R _(C1-C6) or C ₁₀ -C ₃₀ alkylhydroxyamide R _(C1-C6) ,
The remaining two of R ¹⁵ , R ¹⁶ , and R ¹⁷ are independently hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkyl hydroxy, C ₁ -C ₈ alkyl amide R _(C1-C6) , C ₁ -C ₈ alkylaryl amido R _(C1-C6), or a C ₁ -C ₈ alkyl hydroxyamide R _(C1-C6),
R ¹⁸ , R ¹⁹ , R ²⁰ , and R ^{21 which} are the same or different are independently hydrogen, alkyl, arylalkyl, alkylaryl, bromo and chloro containing halogen, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ may be hydrogen or C ₁ -C ₈ alkyl, preferably hydroxy or alkoxyhydroxy.

More preferably, R ¹⁵ is C ₁₀ -C ₃₀ alkyl or alkyl hydroxy, more preferably C ₁₄ -C ₃₀ alkyl or alkyl hydroxy, and even more preferably R ¹⁵ is C ₁₆ -C ₃₀ alkyl or alkyl hydroxy. Even more preferably R ¹⁵ is C ₂₀ -C ₃₀ alkyl or alkyl hydroxy;
R ¹⁶ is C ₁ -C ₆ alkyl, more preferably C ₁ -C ₃ alkyl, even more preferably methyl,
R ¹⁷ is C ₁ -C ₈ alkyl, C ₁ -C ₈ alkyl hydroxy, C ₁ -C ₈ alkyl amide R _(C1-C6) , or C ₁ -C ₈ alkyl hydroxy amide R _(C1-C6) ; More preferably, it may have C ₁ -C ₈ alkylcyamide C ₁ -C ₃ alkylene or C ₁ -C ₈ alkyl hydroxy).

Non-limiting examples of monoalkyl quats of formula (IV) are quats (17), (18), and (19).

または式（ＶＩ）

（式中、Ｘおよびａは式（Ｉ）を参照して上記で定義したとおりであり、
Ｒ²²およびＲ²⁶は独立してＣ₁₆−Ｃ₃₀アルキルであり、
Ｒ²³およびＲ²⁷は各々水素またはＣ₁−Ｃ₃アルキルであり、
Ｒ²⁴は、水素、アルキル、アリールアルキル、アルキルアリール、ブロモおよびクロロを含むハロゲン、アセトキシ、アルキルアセトキシ、アリールアセトキシ、カルボキシ、アルキルカルボキシ、ヒドロキシ、またはアルコキシヒドロキシであり、
Ｒ²⁵およびＲ²⁸は各々Ｃ₁−Ｃ₈アルキルまたはＣ₁−Ｃ₈アルキルヒドロキシであり、
ｎは１〜３で変動し、
ｍは１または２である）を有する。 More preferably, the monoalkyl quat in the mixture is of formula (V):

Or formula (VI)

Wherein X and a are as defined above with reference to formula (I),
R ²² and R ²⁶ are independently C ₁₆ -C ₃₀ alkyl;
R ²³ and R ²⁷ are each hydrogen or C ₁ -C ₃ alkyl;
R ²⁴ is hydrogen, alkyl, arylalkyl, alkylaryl, halogen, including bromo and chloro, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy, or alkoxyhydroxy;
R ²⁵ and R ²⁸ are each C ₁ -C ₈ alkyl or C ₁ -C ₈ alkyl hydroxy;
n varies from 1 to 3,
m is 1 or 2.

Even more preferably, R ²⁴ is hydrogen or lower alkyl, even more preferably hydrogen, n is 2, and m is 2.

Non-limiting examples of monoalkyl quats of formula (V) are quats (20) and (21).

Non-limiting examples of monoalkyl quats of formula (VI) are quats (22) and (23).

  Other non-limiting examples of monoalkyl quats of formula (V) are quats (24) to (28) shown in Table 8.

In a non-limiting example, Tables 9 and 10 show the calculations for mixtures M8 and M9 of Quat (24)-(28) and their substituent content, respectively. Both mixtures are characterized by their C _20-24 content (the specified range is C _20-24 and the reference range is C ₁₀₊ ).

  Monoalkyl imidazoline at and dialkyl imidazoline at can be prepared in a number of ways, including those known to those skilled in the art. One suitable method of preparation is described in US Pat. No. 4,855,440, which is hereby incorporated by reference. Possible synthetic routes include carboxylic acids, anhydrides, or natural or synthetic oils and the desired dialkyltriamine (to prepare dialkyl quats) or N-alkyl-N-alkylamino-diamines (monoalkyl ketones). Reaction to prepare at) followed by quaternization of the resulting imidazoline intermediate.

（式中、Ｒ’およびＲ’’は１０個以上の炭素原子を有するアルキル基、または１０個以上の炭素原子を有するアルキルラジカルを含有する基である） Reaction Scheme 1 shows that certain dialkyl imidazoline ats, especially 1-methyl-1- (alkyl-acylamido-) ethyl) -2-, through the reaction of 1 mole of diethylenetriamine with 2 moles of one or more fatty carboxylic acids. An example of a synthetic route for preparing an alkyl imidazolinium methyl sulfate followed by quaternization with dimethyl sulfate is shown.

(Wherein R ′ and R ″ are alkyl groups having 10 or more carbon atoms, or groups containing alkyl radicals having 10 or more carbon atoms)

（式中、Ｒ’は１０個以上の炭素原子を有するアルキル基またはアルキルラジカルを含有する基であり、Ｒ’’’は１〜８個の炭素原子を有するアルキル基またはアルキルラジカルを含有する基である） Similarly, Reaction Scheme 2 is based on the reaction of N-lower alkyl-N-ethyleneaminodiamine with one fatty carboxylic acid through certain monoalkyl imidazoline ats, especially 1-methyl-1- (lower alkyl)- An example of a synthetic route for preparing 2-alkylimidazolinium chloride followed by quaternization with methyl chloride is shown.

Wherein R ′ is a group containing an alkyl group or alkyl radical having 10 or more carbon atoms, and R ′ ″ is a group containing an alkyl group or alkyl radical having 1 to 8 carbon atoms. Is)

  Reaction Scheme 1 and Reaction Scheme 2 are non-limiting examples. A variety of other imidazoline ats can be obtained through various synthetic routes known to those skilled in the art and / or by varying the starting materials and reactants in the exemplified routes. For example, with respect to the synthetic route shown in Reaction Scheme 1, the carboxylic acids R′COOH and R ″ COOH may be the same or different and / or contain various groups R ′ and R ″. It may be. The nature of the R 'and R "substituents on the carboxylic acid can be used to change the R' and R" substituents on the resulting dialkylimidazoline compound. Similarly, the R ′ and R ″ groups may be varied in the route shown in Reaction Scheme 2.

The carboxyl groups R′CO— and R ″ CO— can be derived from various sources. Thus, essentially pure carboxylic acids can be used. Suitable carboxylic acids having a C ₁₈ -C ₂₄ alkyl group include, for example, arachidic acid (C ²⁰ , containing carboxy carbon ¹ and no double bond in the alkyl group (C ²⁰ : 0)), erucic acid ( C ^22: 1), behenic acid (C ^22: 0), gadoleic (C ^20: 1), erucic acid (C ^22: 1), arachidonic acid ^{(C 20: 4), culpodonic} (C 22: 5), eicosapentaenoic acid (C ^20: 5), docosahexaenoic acid (C ^22: 6), tetracosanoic acid (C ^24: 0); and nervonic acid (C ^24: 1) are included. Other carboxylic acids with any desired alkyl substituents can also be used.

  The mixture of quats may be obtained in any way. For example, in Reaction Scheme 1 and Reaction Scheme 2, an artificial mixture of carboxylic acids may be used. When a mixture of carboxylic acids is used, this reaction usually provides a mixture of corresponding compounds having an R '/ R "substituent content that is similar or identical to the R' / R" distribution in the mixture.

  The use of an artificial mixture of pure carboxylic acids is not economically feasible. Rather, mixtures of carboxylic acids from a single source containing various carboxyl groups such as natural or synthetic oils, triglycerides, etc. are used. For example, such mixtures are available in industrial quantities through saponification of ester-containing natural or synthetic materials.

  Indeed, the carboxylic acid can be directly replaced by an ester-containing natural or synthetic oil or similar substance in the above reaction. Similar to the use of carboxylic acid mixtures, the reaction of ester-containing oils with diamines or triamines usually results in R ′ / R ″ substituent content that is similar or identical to the R ′ / R ″ distribution in the oil. A mixture of compounds comprising is provided.

  Preferably, the compositions of the present invention contain compounds derived from natural and synthetic oils, fatty acids and / or triglycerides.

^The subscript on the number of carbon atoms indicates the number of carbon atoms that do not include the carboxyl carbon. The superscript indicates the number of carbon atoms of the carboxyl group including the carboxyl carbon. Therefore, C ²⁰ is C ₁₉ COO--.

（式中、Ｒ’はＣ₁−Ｃ₃アルキレン、好ましくは−ＣＨ₂ＣＨ₂−基であり、ＲはＲ’ＮＨ₂、Ｃ₁−Ｃ₃₀アルキル、またはＣ₁−Ｃ₃₀アルキルヒドロキシであり、好ましくはＲは−ＣＨ₂ＣＨ₂ＮＨ₂または−ＣＨ₂ＣＨ₂ＯＨである）の化合物と、
ｂ）天然油または合成油由来カルボン酸または天然油または合成油の混合物との反応生成物を提供する。 Thus, in yet another aspect, the present invention provides a) formula

Wherein R ′ is a C ₁ -C ₃ alkylene, preferably —CH ₂ CH ₂ — group, and R is R′NH ₂ , C ₁ -C ₃₀ alkyl, or C ₁ -C ₃₀ alkyl hydroxy. And preferably R is —CH ₂ CH ₂ NH ₂ or —CH ₂ CH ₂ OH);
b) providing a reaction product with a natural or synthetic oil-derived carboxylic acid or a mixture of natural or synthetic oils.

  Oils that can be used directly or provide a mixture of oil-derived carboxylic acids include, for example, HEAR oil, cod liver oil, herring oil, menhaden oil, mustard seed oil, pilchard oil, hair oil, salmon oil, sardine oil and shark liver oil Is included. Of course, other oils and similar materials can also be used. For a list of such substances, one “Bailey's Industrial Oil and Fat Products” (Daniel Stern, John Wiley & Sons, 4th Ed. 1979), which is incorporated herein by reference. Pp. 416-417, 447, 449-450, and 452.

The substituent content of any quat mixture, including those derived from natural or synthetic oils, can be fairly easily characterized by the weight percentage of certain substituents in the mixture. To determine the identity and weight ratio of the quat components in the mixture, any analytical method known to those skilled in the art, such as high performance liquid chromatography or gas chromatography, can be used where appropriate. Based on such analysis, the “substituent content” (eg, C _16-24 or C _24-24 content) of the mixture as defined herein is calculated using the calculation method described herein. And can easily be derived from the weight percentage and molecular weight of the quat component.

Table 11 shows some known approximate percentages of some C ²⁰⁺ in some common oils.

The oils shown in Table 11 generally contain from about 30% to about 90% C _20- C ₃₀ alkyl groups by weight in their fatty acid carboxyl groups. These oils are substantially often vary in C _20- C ₃₀ content further contains some C ₁ -C ₁₉ content.

Therefore, more preferable a mixture of dialkyl quats are rapeseed oil, in particular higher erucic acid rapeseed oil is a (HEAR oil), which is typically 46% by weight in C ^22: 1 alkyl (erucic acid) 1.5% C ²² : 0 alkyl (behenic acid) and 11% C ²⁰ : 1 alkyl (gadoleic acid). Even more preferred is a quat derived from hydrogenated HEAR oil in which the double bond of erucic acid is hydrogenated to give behenic acid (C ²² : 0). To obtain a quat mixture, HEAR oil or a HEAR oil-derived carboxylic acid mixture can be used. Dialkyl imidazoline at mixtures obtained in this way are preferred. In yet embodiment, C ^22: 1, reflecting the spread of alkyl, di - also discussed behenyl imidazolinium methosulfate.

  The composition containing imidazoline at may be in the form of a quat raw material.

  In general, producers provide quat ingredients to personal care product and cosmetic manufacturers who prepare them into final products. An important feature of quat raw materials, as well as the final products incorporating them, is the so-called cationic activity that measures the concentration of positive charges in substances, products, etc. Cationic activity can be measured by several methods readily understood by those skilled in the art. One such method utilizes a standardized solution of an anionic material such as sodium lauryl sulfate. This material is added to the solution containing the quat until complete complexation (end point) of the quat cation is reached. The end point can be measured by potentiometry or by the use of a color change indicator.

式中：ｍＬ＝アニオン性物質のｍＬ数
Ｎ＝使用した溶液の規定度
ＭＷ＝分析されているクアットの分子量
Ｓ．ｗｔ．＝サンプル重量（ｇ） A typical test involves titrating a sample of quat, usually dissolved in a solvent, with a standardized solution of sodium lauryl sulfate until the end point is reached. Reaching an endpoint as described in co-pending and assigned US patent application Ser. No. 09 / 438,631, which is incorporated herein by reference. Then, the cation activity can be calculated by the following formula.

Where: mL = number of mL of anionic material N = normality of the solution used MW = molecular weight of the quat being analyzed wt. = Sample weight (g)

  For additional information regarding methods for measuring cationic activity, both of which are hereby incorporated by reference. Schempp and H.M. T.A. Trau, Wochenblat fur Papierfabrication 19, 1981, pp. 726-732, or J. Org. P. Fischer and K.M. Lohr, Organic Coatings Science Technology, Vol. 8, pp. 227-249, Marcel Dekker, Inc. See April 1986.

  It is desirable to provide the quat raw material in a concentrated form with high cationic activity as a solid solution or semi-solid solution or dispersion. While not intending to be bound by any particular theory, the desired amount of a given quat or mixture of quats to be included in the formulation can be measured by the cationic activity of the quat raw material. Quat feeds with high cationic activity allow for better transport efficiency because they occupy less space while providing the same desired amount of quat. Furthermore, it is desirable to produce a quat feed that provides ease of industrial handling and storage in addition to having high cationic activity. For example, a quat feed that melts at a lower temperature minimizes quat degradation and improves energy efficiency. For this purpose, the quat raw material is preferably flaky or pastilleatable.

  Thus, a composition containing an imidazoline or quat mixture as described herein may be in the form of a concentrated, usually solid, solution or suspension of quat or mixture in a suitable carrier. Such a composition is referred to herein as a quat ingredient. Preferred carriers are solvents, and preferred solvents include isopropyl alcohol, SDA-40, propylene glycol, butylene glycol, various fatty alcohols, and mixtures thereof. Preferably, the quat raw material of the present invention is a flaky or puffable solid with high quat cation activity. The quat cation activity is a cation activity considered to be an attribute of the quaternary nitrogen compound. The preferred total quat cation activity of the quat raw material of the present invention is higher than 10%, preferably higher than 20%, more preferably higher than 35%, even more preferably higher than 50%.

  The quat ingredients of the present invention may also contain one or more desirable ingredients of the final cosmetic / personal care product formulation such as emollients as well as various impurities. A list of possible ingredients can be found below.

  The composition containing the imidazoline and / or quat mixture may be in the form of various cosmetic and / or personal care products. Such a composition can be referred to as a final product composition. Examples of final product compositions include sunscreen compositions for hair and / or skin such as lotions, gels, sprays, hand cleaners, bath compositions, suntan oils, antiperspirant compositions, perfumes and colons, cold cream , Preshaves, deodorants, topical ointments for skin, skin moisturizers, facial cleansers, cleansing creams, skin gels, shampoos, hair conditioners, detergents, household cleaners, makeup products, lipstick products, mascara and hair coloring agents. The preferred final product composition of the present invention is a composition for handling human hair, such as a shampoo or conditioner.

  The final product composition, including preparations for skin and hair, includes the imidazoline at or imidazoline at mixture described herein. The amount of imidazoline at or mixture in the product depends on the specific application and is about 0.1% to about 40%, more preferably about 0.1% to about 10%, even more preferably by weight of the product composition May vary from about 0.5% to about 2%. However, varying amounts of imidazoline or quat mixtures may be preferred depending on the nature of the product.

  The final product composition comprising imidazoline at or a mixture of imidazoline at may be in the form of liquids, gels, creams, emulsions, foams and solids and may be transparent or opaque. And can be prepared as aqueous and non-aqueous preparations including, but not limited to, topical preparations. Preferably, the final product composition is a dispersion or solution in water or a mixture of water and a suitable second solvent. Suitable inert solvents include various lower alkanols and glycols. Suitable for use with the present invention are lower alkanols having 1 to 4 carbon atoms, with lower alkanols having 2 to 3 carbon atoms being preferred. Although glycols having 3 to 8 carbon atoms are suitable for use with the present invention, glycols having 3 to 6 carbon atoms are preferred. Examples of suitable lower alkanols and glycols include methanol, ethanol, isopropanol, butanol, hexylene glycol, 1,3-butylene glycol, 1,2- and 1,3-propanediol, 2-methyl 1,3-propane Diol, propylene glycol, diethylene glycol and the like are included. The total amount of solvent may be up to about 98% by weight of the composition, preferably from about 20% to about 90%, more preferably from about 50% to about 90%. However, depending on the nature of the product, different amounts of solvent may be preferred. When a mixture of water and a second solvent is used, the second solvent may be present in an amount of up to 90%, preferably from about 25% to about 80% by weight of water in the composition.

  In addition to the imidazoline quaternary compound, the final product composition may contain both conventional and other various active ingredients and additional ingredients. Of course, the decision to include the selection of one ingredient and the particular active ingredient and additional ingredients depends on the particular application and product preparation method. Furthermore, the boundary between “active” ingredients and “additional ingredients” is artificial and depends on the specific application and product type. A substance that is an “active” ingredient in one application and product may be an “additional” ingredient in another application, and vice versa.

  The final product composition may contain one or more active ingredients that provide certain benefits for the application purpose of the composition, such as hair or skin. Such active ingredients include detergents, hair conditioning agents, skin conditioning agents, hair styling agents, anti-dandruff agents, hair growth promoters, perfumes, sunscreen compounds, dyes, humectants, film formers, hair color One or more substances may be included, such as makeup agents, cleaning agents, thickeners, emulsifiers, preservatives, deodorant active agents, surfactants and topical pharmaceuticals for transdermal delivery.

  The choice of active ingredient depends on the nature of the desired cosmetic or personal care product. For example, sunscreen compounds can be used in sunscreen lotions, shampoos, medicated shampoos, hair care lotions and the like. For each type of active ingredient, one or more compounds may be present. Similarly, one or more types of active ingredients may be present.

  Imidazoline at and / or quat mixtures are typically considered to be the degree of adhesion of the hydrophobic component to the hair, and the desired hair substantivity of the hydrophobic component of cosmetic and personal care products. It is thought to improve. The hydrophobic component is a substantially water-insoluble component. Typically, such hydrophobic components are oil soluble. Accordingly, the compositions described herein may further comprise at least one hydrophobic component, examples of which include plant extracts, vitamin E, vitamin A, silicones, waxes and antioxidants.

[Surfactant]
In addition to the imidazoline quaternary compound and / or mixture, the compositions described herein include one or more nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants. Other surfactants may be present, including zwitterionic surfactants, and mixtures thereof. For some surfactants that can be used in combination with the compositions of the present invention, McCutcheon's, Detergents and Emulsifiers, (1986), US Patent, all of which is incorporated herein by reference. 5,151,210, U.S. Patent 5,151,209, U.S. Patent 5,120,532, U.S. Patent 5,011,681, U.S. Patent 4,788,006, U.S. Patent See US Pat. No. 4,741,855, US Pat. No. 4,704,272, US Pat. No. 4,557,853, US Pat. No. 4,421,769, US Pat. No. 3,755,560. I want.

[Cationic surfactant]
The imidazoline quaternary compounds of the present invention are cationic surfactants that are particularly adapted for use in various personal care products such as hair care products such as conditioners and shampoos. In addition, other cationic surfactants may be present in the composition of the present invention. The amount and nature of the cationic surfactant present in the composition of the present invention depends on the nature of the composition. In the final product composition, the total amount of cationic surfactants including the imidazoline at and imidazoline at mixtures described herein is 0.1% to about 40% by weight of the product composition, and more. Preferably it may vary from about 0.1% to about 15%, even more preferably from about 0.5% to about 2%. However, varying amounts of cationic surfactant may be preferred depending on the nature of the product. Suitable additional cationic surfactants are incorporated herein by reference, McCutcheon, Detergents & Emulsifiers, (M.C. Publishing Co. 1979); US Pat. No. 3,155, No. 591, U.S. Pat. No. 3,929,678, U.S. Pat. No. 3,959,461, and U.S. Pat. No. 4,387,090.

（式中、Ｘおよびａは以前に記載したとおりであり、Ｑ₁はＣ₁₂−Ｃ₂₂アルキル、Ｃ₁₂−Ｃ₂₂アルキルアミドＲ_(C1-C6)アルキレン、Ｃ₁₂−Ｃ₂₂アルキルヒドロキシであり、Ｑ₂はＣ₁₂−Ｃ₂₂アルキル、Ｃ₁₂−Ｃ₂₂アルキルアミドＲ_(C1-C6)アルキレン、Ｃ₁₂−Ｃ₂₂アルキルヒドロキシ、ベンジル、またはＣ₁−Ｃ₆アルキルであり、Ｑ₃およびＱ₄は独立してＣ₁−Ｃ₆アルキルまたはベンジルである）の第四級アンモニウムカチオン性界面活性剤を含んでいてよい。 [Ammonium Quat]
The composition of the present invention has the formula

Wherein X and a are as previously described, Q ₁ is C ₁₂ -C ₂₂ alkyl, C ₁₂ -C ₂₂ alkylamide R _(C1-C6) alkylene, C ₁₂ -C ₂₂ alkylhydroxy , Q ₂ is C ₁₂ -C ₂₂ alkyl, C ₁₂ -C ₂₂ alkylamide R _(C1-C6) alkylene, C ₁₂ -C ₂₂ alkylhydroxy, benzyl, or C ₁ -C ₆ alkyl, and Q ₃ and Q ₄ may comprise a quaternary ammonium cationic surfactant of independently C ₁ -C ₆ alkyl or benzyl).

  Examples of suitable quaternary ammonium surfactants include cetyl ammonium chloride, cetyl ammonium bromide, lauryl ammonium chloride, lauryl ammonium bromide, stearyl ammonium chloride, stearyl ammonium bromide, cetyl dimethyl ammonium chloride, cetyl dimethyl ammonium bromide, lauryl dimethyl Ammonium chloride, lauryldimethylammonium bromide, stearyldimethylammonium chloride, stearyldimethylammonium bromide, cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, lauryltrimethylammonium chloride, lauryltrimethylammonium bromide, stearyltrimethylammonium chloride, stearyltrimethyl Ruammonium bromide, lauryl dimethyl ammonium chloride, stearyl dimethyl cetyl ditallow dimethyl ammonium chloride, dicetyl ammonium chloride, dicetyl ammonium bromide, dilauryl ammonium chloride, dilauryl ammonium bromide, distearyl ammonium bromide, distearyl ammonium bromide, dicetyl Included are methylammonium chloride, dicetylmethylammonium bromide, dilaurylmethylammonium chloride, dilaurylmethylammonium bromide, distearylmethylammonium chloride, distearyldimethylammonium chloride, distearylmethylammonium bromide, and mixtures thereof.

Additional quaternary ammonium salts include those where the C ₁₂ -C ₂₂ alkyl is derived from a tallow fatty acid or a coconut fatty acid. Examples of quaternary ammonium salts derived from these tallow and coconut sources include ditallow dimethyl ammonium chloride, ditallow dimethyl ammonium methyl sulfate, di (hydrogenated tallow) dimethyl ammonium chloride, di (hydrogenated tallow) dimethyl ammonium Acetate, ditallow dipropylammonium phosphate, ditallow dimethylammonium nitrate, di (coconut alkyl) dimethylammonium chloride, di (coconut alkyl) dimethylammonium bromide, tallow ammonium chloride, coconut ammonium chloride, stearamidepropyl PG-dimonium chloride phosphate , Stearamidopropyl ethyl dimonium etosulphate, stearamidopropyldimethyl (myristyl acetate) Niumukurorido, stearamidopropyl dimethyl cetearyl ammonium tosylate, stearamidopropyl dimethyl ammonium chloride, are included stearamidopropyl dimethyl ammonium lactate, and mixtures thereof.

  More preferred quaternary ammonium surfactants are dilauryldimethylammonium chloride, distearyldimethylammonium chloride, dimyristyldimethylammonium chloride, dipalmityldimethylammonium chloride, distearyldimethylammonium chloride, stearamidepropyl PG-dimonium chloride. Phosphate, stearamide propyl ethyl dimonium etosulphate, stearamide propyl dimethyl (myristyl acetate) ammonium chloride, stearamide propyl dimethyl cetearyl ammonium tosylate, stearamide propyl dimethyl ammonium chloride, stearamide propyl dimethyl ammonium lactate, and their It is a mixture.

[Aliphatic amine]
The compositions of the present invention may further comprise primary, secondary and tertiary C ₁₂ -C ₂₂ amine salts. Examples of such suitable amines include stearamidopropyldimethylamine, diethylaminoethyl stearamide, dimethyl stearamine, dimethyl soiamine, soiamine, tri (decyl) amine, ethyl stearylamine, ethoxylated stearylamine, dihydroxyethyl stearyl Amine, and arachidyl behenylamine are included. Suitable amine salts include halogens, acetates, phosphates, nitrates, citrates, lactates and alkyl sulfates. Such salts include stearylamine hydrochloride, soyamine chloride, stearylamine formate, N-tallowpropanediamine dichloride and stearamidepropyldimethylamine citrate. Some cationic amine surfactants useful in the compositions of the present invention are disclosed in US Pat. No. 4,275,055, which is hereby incorporated by reference.

[Amidamine]
The composition of the present invention is prepared by Croda Inc. It may also include aminoamides as disclosed in US patent application Ser. No. 09 / 409,203, assigned to the Company and incorporated herein by reference.

[Nonionic surfactant]
The compositions of the present invention may also contain various nonionic surfactants. Particularly suitable nonionic surfactants are the condensation products of C ₈ -C ₃₀ alcohol with a sugar or starch polymers. These compounds have the formula (S) _n —O—R (wherein S is a sugar component such as glucose, fructose, mannose and galactose, n is an integer from about 1 to about 1,000, and R is it can be represented by C ₈ -C ₃₀ alkyl). Examples of suitable C ₈ -C ₃₀ alcohol R groups may result from the decyl alcohol, cetyl alcohol, stearyl alcohol, lauryl alcohol, myristyl alcohol, oleyl alcohol and the like are included. Particular examples of these surfactants include decyl polyglucoside and lauryl polyglucoside.

Other suitable nonionic surfactants include alkylene oxide condensation products comprising fatty acids (eg, alkylene oxide esters of fatty acids). These materials have the general formula RCO (X) _n OH, where R is C ₁₀ -C ₃₀ alkyl and X is —OCH ₂ CH ₂ — (derived from ethylene oxide) or —OCH ₂ CHCH ₃ — (propylene And n is an integer from about 1 to about 200).

Yet another suitable nonionic surfactant is the formula RCO (X) _n OOCR _where R is C ₁₀ -C ₃₀ alkyl and X is —OCH ₂ CH ₂ — (derived from ethylene oxide). Or a condensation product of an alkylene oxide and a fatty acid (ie, an alkylene oxide diester of a fatty acid) having —OCH ₂ CHCH ₃ — (derived from propylene oxide), where n is an integer from about 1 to about 200. .

Yet another nonionic surfactant is a compound of the general formula R (X) _n OR ′, where R is C ₁₀ -C ₃₀ alkyl, n is an integer from about 1 to about 200, and R ′ Is a condensation product of an alkylene oxide and an aliphatic alcohol having H or C ₁₀ -C ₃₀ alkyl) (ie, an alkylene oxide ether of an aliphatic alcohol).

In addition, other nonionic surfactants are those of the formula RCO (X) _n OR ′ _where R and R ′ are C ₁₀ -C ₃₀ alkyl and X is —OCH ₂ CH ₂ — (derived from ethylene oxide). Or —OCH ₂ CHCH ₃ — (derived from propylene oxide) and n is an integer from about 1 to about 200.

  Examples of nonionic surfactants derived from alkylene oxides include ceteth-1, ceteth-2, ceteth-6, ceteth-10, ceteth-12, ceteareth-2, ceteareth-6, ceteareth-10, ceteareth- 12, steareth-1, steareth-2, steareth-6, steareth-10, steareth-12, PEG-2 stearate, PEG-4 stearate, PEG-6 stearate, PEG-10 stearate, PEG-12 stea Rate, PEG-20 glyceryl stearate, PEG-80 glyceryl tallowate, PPG-10 glyceryl stearate, PEG-30 glyceryl cocoate, PEG-80 glyceryl cocoate, PEG-200 glyceryl tallowate, PEG-8 dilaurate, PEG-10 distearate, Oh Beauty mixtures thereof.

  Still other useful nonionic surfactants include, for example, US Pat. No. 2,965,576, US Pat. No. 2,703,798, which is hereby incorporated by reference. And polyhydroxy fatty acid amides disclosed in US Pat. No. 1,985,424.

[Anionic surfactant]
The compositions of the present invention may also contain various anionic surfactants. Some examples of suitable anionic surfactants are disclosed in US Pat. No. 3,929,678, which is incorporated herein by reference. Examples of other suitable anionic surfactants include alcoyl isoethionate and alkyl ether sulfates.

Alcohol isethionates are typically of the formula RCO——OCH ₂ CH ₂ —SO ₃ M where R is C ₁₀ -C ₃₀ alkyl and M is such as ammonium, sodium, potassium or triethanolamine. A water-soluble cation). Examples of suitable isethionates include ammonium cocoyl isethionate, sodium cocoyl isethionate, sodium lauroiyl thiothionate, sodium stearoyl isethionate, and mixtures thereof. Preferred for use herein are ammonium cocoyl isethionate, sodium cocoyl isethionate, and mixtures thereof.

Alkyl ether sulfates are typically of the formula ROSO ₃ M and RO (C ₂ H ₄ O) _x SO ₃ M where R is C ₁₀ -C ₃₀ alkyl and x is from about 1 to about 10. And M is a water-soluble cation such as ammonium, sodium, potassium, and triethanolamine).

Yet another suitable class of anionic surfactants are succinates and alkali metal salts of C ₈ -C ₃₀ carboxylic acids, including C ₁₂ -C ₂₄ olefin sulfonates and carboxylates, and the formula R ₁ —SO ₃ M Wherein R ₁ is C ₈ -C ₃₀ alkyl, preferably C ₁₂ -C ₂₂ alkyl and M is a cation.

[Amphoteric surfactant]
The composition of the present invention may also contain a zwitterionic surfactant and an amphoteric surfactant. Suitable amphoteric and zwitterionic surfactants are, for example, the formulas RN (CH ₂ ) _m CO ₂ M ₂ and RNH (CH ₂ ) _m CO ₂ M, where m varies from 1 to 4, R is C ₈ -C ₃₀ alkyl, preferably C ₁₂ -C ₂₂ alkyl, and M is H, alkali metal, alkaline earth metal ammonium or alkanol ammonium) and includes iminodiaalkanoates and aminoalkanoates , alkyl imino acetates, carboxylates, sulfonates, sulfates, phosphates, and mono- phosphonates such as - or di -C ₈ -C ₂₄ derivatives of secondary and tertiary amines.

  Other suitable amphoteric surfactants and zwitterionic surfactants are imidazolinium and ammonium derivatives. Suitable examples of such amphoteric surfactants include sodium 3-dodecyl-aminopropionate, sodium 3-dodecylaminopropane sulfonate, N-alkyl taurine; N-higher alkyl aspartic acid, and coamidopropyl PG- Dimonium chloride phosphate is included. Additional examples of suitable amphoteric surfactants and zwitterionic surfactants are given in US Pat. No. 2,658,072, incorporated herein by reference, US Pat. See 438,091 and US Pat. No. 2,528,378.

  Yet another suitable amphoteric surfactant and zwitterionic surfactant is betaine. Examples of suitable betaines include cocodimethylcarboxymethylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethylalphacarboxyethylbetaine, cetyldimethylcarboxymethylbetaine, cetyldimethylbetaine, laurylbis- (2-hydroxyethyl) carboxymethylbetaine, stearyl Bis- (2-hydroxypropyl) carboxymethylbetaine, oleyldimethyl γ-carboxypropylbetaine, laurylbis- (2-hydroxypropyl) α-carboxyethylbetaine, cocodimethylsulfopropylbetaine, stearyldimethylsulfopropylbetaine, lauryldimethylsulfoethyl Betaine, lauryl bis- (2-hydroxyethyl) sulfopropyl betaine, and amide betaine And amidosulfobetaine, oleylbetaine, and cocamidopropylbetaine.

[Sunscreen compound]
A wide range of sunscreen compounds are suitable for use with the compositions of the present invention. Depending on the nature of the composition, the sunscreen compound can be added in an amount up to about 40% by weight of the composition, preferably from about 1% to about 30%. However, the preferred amount may vary depending on the nature of the product. Thus, for a final product composition in the form of a shampoo or conditioner, a suitable sunscreen agent is up to about 40% by weight of the composition, preferably from about 0.5% to about 5% by weight of the composition. %, More preferably from about 05 to about 1.5%. Examples of suitable sunscreen compounds include, for example, p-aminobenzoic acid, its salts and derivatives; anthranilate; salicylate; cinnamic acid derivatives; dihydroxycinnamic acid derivatives; trihydroxycinnamic acid derivatives; Naphthol sulfonate; dihydroxynaphtholic acid and its salts; coumarin derivatives; diazoles; quinine salts; quinoline derivatives; hydroxy- or methoxy-substituted benzophenones; uric acid and viral acids; Benzoic acid, salicylate, ferric acid derivative, phenylbenzimidazole sulfonic acid, benzophenone sulfonic acid, thioctic acid derivative, oil-soluble cinnamic acid, and benzophene It includes emissions. For other suitable sunscreen compounds, see Segarin, et al., Which is hereby incorporated by reference. , Cosmetics Science and Technology, Chapter VIII, page 189 et seq.

  Particularly suitable sunscreen compounds include 2-ethylhexyl p-methoxycinnamate, 4,4′-t-butylmethoxydibenzoylmethane, 2-hydroxy-4-methoxybenzophenone, octyldimethyl p-aminobenzoic acid, digalloyl. Trioleate, 2,2-dihydroxy-4-methoxybenzophenone, ethyl-4-> bis (hydroxypropyl)! -Aminobenzoate, 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate, 2-ethylhexyl salicylate, glyceryl p-aminobenzoate, 3,3,5-trimethylcyclohexyl salicylate, methyl anthranilate, p -Dimethyl-aminobenzoic acid or aminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, 2-phenylbenzimidazole-5-sulfonic acid, 2- (p-dimethyl-aminophenyl) -5-sulfonicbenzoxazoic acid, para-aminobenzoic acid Acid, benzophenone-1, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-8, benzophenone-12 Methoxycinnamate, avobenzone, ethyl dihydroxypropyl para-aminobenzoic acid, glyceryl para-aminobenzoic acid, methyl anthranilate, octocrylene, octyl dimethyl para-aminobenzoic acid, octyl methoxycinnamate, octyl salicylate, zinc oxide, Titanium dioxide and red petrolatum are included.

[Emulsifier]
The composition of the present invention may further comprise one or more emollient compounds such as fats, waxes, lipids, silicones, hydrocarbons, aliphatic alcohols and a wide range of solvent materials. The amount of emollient depends on the application. For the final product composition, the emollient is in an amount up to 50% by weight of the composition, preferably about 0.1% to about 20%, and more preferably about 0.5% by weight of the composition. % To about 10%.

Examples of suitable emollients, C ₈ -C ₃₀ alkyl esters of C ₈ -C ₃₀ carboxylic acids; C _1-6 diol monoesters and diesters of C ₈ -C ₃₀ carboxylic acids; C ₈ -C ₃₀ carboxylic monoglycerides of acids, diglycerides, and triglycerides, cholesterol esters of C ₈ -C ₃₀ carboxylic acids, cholesterol, and hydrocarbons. Examples of these materials include diisopropyl adipate, isopropyl myristate, isopropyl palmitate, ethylhexyl palmitate, isodecyl neopentanoate, C ₁₂ - ₁₅ alcohol benzoate, diethyl hexyl maleate, PPG-14 butyl ether, PPG-2 Myristyl ether propionate, cetyl ricinoleate, cholesterol stearate, cholesterol isostearate, cholesterol acetate, jojoba oil, cocoa butter, shea butter, lanolin, lanolin ester, mineral oil, petrolatum, and linear and branched C ₁₆ -C ₃₀ contains hydrocarbons.

Furthermore the useful is, for example, stearyl alcohol, isostearyl alcohol, Ehenyl alcohol, cetyl alcohol, isocetyl alcohol, and linear and branched aliphatic C ₈ -C ₃₀ alcohols, such as mixtures thereof. Examples of other suitable emollients are disclosed in US Pat. No. 4,919,934, which is hereby incorporated by reference.

  Other suitable emollients are various alkoxylated ethers, diethers, esters, diesters, and trimesters. Examples of suitable alkoxylated ethers include PPG-10 butyl ether, PPG-11 butyl ether, PPG-12 butyl ether, PPG-13 butyl ether, PPG-14 butyl ether, PPG-15 butyl ether, PPG-16 butyl ether, PPG-17 butyl ether, PPG-18 butyl ether, PPG-19 butyl ether, PPG-20 butyl ether, PPG-22 butyl ether, PPG-24 butyl ether, PPG-30 butyl ether, PPG-11 stearyl ether, PPG-15 stearyl ether, PPG-10 oleyl ether, PPG- 7 lauryl ether, PPG-30 isocetyl ether, PPG-10 glyceryl ether, PPG-15 glyceryl ether, PPG-10 butyre Glycol ether, PPG-15 butylene glycol ether, PPG-27 glyceryl ether, PPG-30 cetyl ether, PPG-28 cetyl ether, PPG-10 cetyl ether, PPG-10 hexylene glycol ether, PPG-15 hexylene glycol ether, PPG-10 1,2,6-hexanetriol ether, PPG-15 1,2,6-hexanetriol ether, and mixtures thereof are included.

  Examples of alkoxylated diethers include PPG-10 1,4-butanediol diether, PPG-12 1,4-butanediol diether, PPG-14 1,4-butanediol diether, PPG-2 butanediol diether. Ether, PPG-10 1,6-hexanediol diether, PPG-12 1,6-hexanediol diether, PPG-14 hexanediol diether, PPG-20 hexanediol diether, and mixtures thereof. PPG-10 1,4-butanediol diether, PPG-12 1,4-butanediol diether, PPG-10 1,6-hexanediol diether, and PPG-12 hexanediol diether, and One selected from the group consisting of mixtures thereof.

Examples of suitable alkoxylated diesters and trimesters are available from Croda Inc. US Pat. Nos. 5,382,377, 5,455,025 and 5,597,555, which are hereby incorporated by reference and made a part hereof. .
Suitable lipids, C ₈ -C ₂₀ alcohol mono sorbitan esters, C ₈ -C ₂₀ alcohol sorbitan diesters, C ₈ -C ₂₀ alcohol sorbitan triesters, C ₈ -C ₂₀ alcohol sucrose monoesters, C ₈ -C ₂₀ alcohol sucrose diesters, C ₈ -C ₂₀ alcohol sucrose triesters, and C ₂ -C ₆₂ - include C ₈ -C ₂₀ fatty alcohol esters of hydroxy acids. Examples of particularly suitable lipids are sorbitan diisostearate, sorbitan dioleate, sorbitan distearate, sorbitan isostearate, sorbitan laurate, sorbitan oleate, sorbitan palmitate, sorbitan sesquioleate, sorbitan esquiteate Rate, sorbitan stearate, sorbitan triisostearate, sorbitan trisoleate, sorbitan tristearate, sucrose cocoate, sucrose laurate, sucrose distearate, sucrose laurate, sucrose myristate, sucrose oleate, sucrose palmitate, sucrose Ricinoleate, sucrose stearate, sucrose tribehenate, sucrose tristearate, myristyl lactate, stearyl la Tate, isostearyl lactate, cetyl lactate, palmityl lactate, cocoyl lactate, and mixtures thereof.

  Other suitable emollients include mineral oil, petrolatum, cholesterol, dimethicone, dimethiconol, stearyl alcohol, cetyl alcohol, behenyl alcohol, diisopropyl adipate, isopropyl myristate, myristyl myristate, cetyl ricinoleate, sorbitan distearate, sorbitan Dilaurate, sorbitan stearate, sorbitan laurate, sucrose laurate, sucrose dilaurate, sodium isostearyl lactylate, lauryl pidolate, sorbitan stearate, stearyl alcohol, cetyl alcohol, behenyl alcohol, PPG-14 butyl ether, PPG-15 stearyl ether, And mixtures thereof.

[emulsifier]
The composition of the present invention may also contain various emulsifiers. In the final product composition of the present invention, the emulsifier can be included in an amount up to about 10% by weight of the composition, preferably in an amount of about 0.5% to about 5%. Examples of suitable emulsifiers include stearamide propyl PG-dimonium chloride phosphate, stearamide propyl ethyl dimonium ethosulphate, stearamide propyl dimethyl (myristyl acetate) ammonium chloride, stearamide propyl dimethyl cetearyl ammonium tosylate, stearamide propyl Aramidpropyl dimethyl ammonium chloride, stearamide propyl dimethyl ammonium lactate, polyethylene glycol, polypropylene glyosis, and mixtures thereof are included.

[Anti-dandruff agent]
The composition of the present invention may also contain an anti-dandruff agent. Examples of suitable anti-dandruff agents include zinc pyrithione, sulfur, and selenium sulfide.

[Hair oxidizer]
The composition of the present invention may also contain a hair oxidant / reducing agent. Examples of suitable hair oxidizers / reducing agents include hydrogen peroxide, perborate, thioglycolate and granulate.

[Thickener]
The compositions of the present invention may also include various thickening agents such as cross-linked acrylates, nonionic polyacrylamides, xanthan gum, guar gum, gellan gum, etc .; polyalkylsiloxanes, polyarylsiloxanes and aminosilicones. . In the final product composition of the present invention, the thickener may be included in an amount up to about 10% by weight of the composition, preferably in an amount of about 0.2% to about 5%.

  Specific examples of suitable thickening silicone compounds include polydimethylsiloxane, phenylsilicone, polydiethylsiloxane, and polymethylphenylsiloxane. Some suitable silicone compounds are disclosed in European Patent Application No. 95,238 and US Pat. No. 4,185,017, which are incorporated herein by reference. The compositions of the present invention may also include a silicone polymer material that provides both style retention and conditioning benefits to the hair. Such materials are described in US Pat. No. 4,902,499, which is hereby incorporated by reference.

[Hair conditioning agent]
The composition of the present invention may also comprise a hydrolyzed animal proteinaceous hair conditioning agent. Croda Incorporated sells commercially available materials, for example, under the trademark Crotain Q-RTM. Other examples include urea, glycerol, and propoxylated glycerol, including those disclosed in US Pat. No. 4,976,953, which is hereby incorporated by reference. .

[Hair setting agent]
The compositions of the present invention may also include a hair setting agent that imparts styling benefits when applied to the hair. The hair setting polymer may be a homopolymer, a copolymer, a terpolymer or the like. For convenience in describing polymers in this regard, the monomer units present in the polymer can be referred to as monomers from which they can be derived. The monomer may be ionic (eg, anionic, cationic, amphoteric, zwitterionic) or nonionic.

  Examples of anionic monomers include unsaturated carboxylic acid monomers such as acrylic acid, methacrylic acid, maleic acid, maleic acid half ester, itaconic acid, fumaric acid, and crotonic acid; hydroxyethyl acrylate, and hydroxyethyl methacrylate, hydroxypropyl Half-esters of unsaturated polybasic acid anhydrides such as succinic anhydride and phthalic anhydride with hydroxyl group-containing acrylates and / or methacrylates such as acrylates; monomers having sulfonic acid groups such as styrene sulfonic acid, sulfoethyl acrylate and methacrylate And having phosphate groups such as acid phosphooxyethyl acrylate and methacrylate, 3-chloro-2-acid phosphooxypropyl acrylate and methacrylate, etc. It includes a monomer.

Examples of cationic monomers include monomers derived from acrylic acid or methacrylic acid, and 1-5 carbon atoms in alkyl such as (meth) acryloxypropylmethylammonium chloride and (meth) acryloxypropyltriethylammonium bromide. A quaternized epihalohydrin product of a trialkylamine having C ₁ -C ₆ such as dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate or dimethylaminopropyl (meth) acrylamide Examples include methacrylic acid or methacrylamide having an alkyl group and amine derivatives of methacrylic acid derived from dialkylalkanolamines or amine derivatives of methacrylamide.

  Examples of amphoteric monomers include dimethylaminoethyl (meth) acrylate with halogenated fatty acid salts such as potassium monochloroacetate, sodium monobromopropionate, aminoethyl propanol salt of monochloroacetic acid, triethanolamine salt of monochloroacetic acid, Modified with an amine derivative of the above (meth) acrylic acid such as dimethylaminopropyl (meth) acrylamide or a zwitterionized derivative of an amine derivative of (meth) acrylamide; and propane sultone as discussed above ( An amine derivative of (meth) acrylic acid or (meth) acrylamide is included.

Examples of nonionic monomers are methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl -1-butanol, 1-methyl-1-butanol, 3-methyl-1-butanol, 1-methyl-1-pentanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, t- Butanol, cyclohexanol, 2-ethyl-1-butanol, 3-heptanol, benzyl alcohol, 2-octanol, 6-methyl-1-heptanol, 2-ethyl-1-hexanol, 3,5-dimethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, 1-decanol, 1-dodecanol, 1-hexadecane Vinyl esters such as vinyl acetate; Lumpur, 1-octadecanol, C ₁ -C ₂₄ alcohols acrylic acid or methacrylic acid esters, such as styrene; chlorostyrene vinyl chloride; vinylidene chloride; acrylonitrile; alpha-methylstyrene; t -Butylstyrene; butadiene; cyclohexadiene; ethylene; propylene; vinyl toluene; alkoxyalkyl (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate; allyl acrylate, allyl methacrylate, cyclohexyl acrylate and methacrylate, oleyl acrylate And methacrylate, benzyl acrylate and methacrylate, tetrahydrofurfuryl acrylate and methacrylate, ethylene glycol di Acrylate and ethylene glycol methacrylate, 1,3-butylene glycol diacrylate and 1,3-butylene glycol methacrylate, diacetone acrylamide, isobornyl (meth) acrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, methyl methacrylate, t -Butyl acrylate, t-butyl methacrylate, and mixtures thereof.

  Examples of anionic hair styling polymers include vinyl acetate and crotonic acid copolymers, vinyl acetates such as vinyl neodecanoate, crotonic acid, and terpolymers of vinyl esters of α-branched saturated aliphatic monocarboxylic acids; and Copolymers, acrylic copolymers and terpolymers of methyl vinyl ether and maleic anhydride containing acrylic acid or methacrylic acid.

  Examples of cationic hair styling polymers include amino functional acrylate monomers such as lower alkylaminoalkyl acrylate or methacrylate monomers such as dimethylaminomethyl methacrylate and alkyl methacrylates such as N-vinyl pyrrolidone or methyl methacrylate and ethyl methacrylate and methyl Copolymers with compatible monomers such as acrylates and alkyl acrylates such as butyl acrylate.

[Other ingredients]
The compositions of the present invention may also contain a wide range of other ingredients. Some suitable other ingredients commonly used in the cosmetic and personal care products industry are listed in The CTFA Cosmetic Ingredient Handbook, (2nd Ed., 1992), which is hereby incorporated by reference. Has been described.

  Therefore, the composition of the present invention comprises one or more hygroscopic agents, anti-acne agents, antiperspirants, anti-caking agents, antifoaming agents, antibacterial agents, antioxidants, anti-dandruff agents, astrogen, binders, buffering agents, Additive, buffer agent, filler, chelating agent, chemical additive, coupling agent, conditioner, colorant, cosmetic astringent, cosmetic biocide, denaturant, medicinal astringent, detergent, dispersant, Analgesics for external use, film forming agent, foaming agent, fragrance, moisturizer, keratolytic agent, opacifier, pH adjuster, preservative, propellant, protein, retinoid, reducing agent, sequestering agent, skin bleaching agent Agents, skin conditioning agents (moisturizers, miscellaneous and occlusive), skin soothing agents, skin treatment agents, softeners, solubilizers, lubricants, penetrants, fluidizers, solvents and cosolvents, sun Screening additive Salts, may not also contain essential oils as well as vitamins.

  Examples of suitable pH adjusting agents include sodium hydroxide, triethanolamine, and aminomethylpropanol, and mixtures thereof. If a pH adjusting agent is present in the final product composition, the amount may vary from about 0.01% to about 5%, preferably from about 0.1% to about 2% by weight of the composition. is there.

  Examples of suitable film formers include glycerin / diethylene glycol myristate copolymer, glycerin / diethylene glycol adipate copolymer, ethyl ester of PVM / MA copolymer, PVP / dimethiconyl acrylate / polycarbamyl / polyglycol ester, and mixtures thereof It is. If a film former is present in the final product composition, the amount is about 0.1% to about 15.0% by weight of the composition, preferably about 0.1% by weight of the composition. May vary from ~ 2.5%.

  Examples of suitable vitamins include tocopherol, tocopherol acetate, retinoic acid, retinol, and retinoid.

  Examples of suitable anti-acne agents include resorcinol, sulfur, salicylic acid, erythromycin, zinc, and benzoyl peroxide.

  Examples of suitable skin bleaches or lightening agents include hydroquinone, and kojic acid. Examples of suitable aesthetic ingredients such as fragrances, pigments, colorants, etc. include panthenol and its derivatives (eg ethyl panthenol), aloe vera, pantothenic acid and its derivatives, clove oil, menthol, camphor, eucalyptus oil, Eugenol, menthyl lactate, witch hazel distillate, allantoin, bisabolol, and dipotassium glycyrrhizinate.

  The compositions of the present invention are illustrated in detail in the following examples.

Preparation of 1-methyl-1-((ercylamido-) ethyl) -2-ercylimidazolinium methyl sulfate 3132 g (4.62 mol) of erucic acid and into a dry stirred pressure vessel equipped with a nitrogen inlet and 216 g (2.1 mol) of diethylenetriamine was added. The vessel was purged with nitrogen and heated to 170 ° C. for 4-5 hours. The reaction mixture was then heated to 180 ° C. and a vacuum was applied for an additional 4-5 hours. The reaction mixture was cooled to 95-100 ° C. and about 1.5 kg cetearyl alcohol was added. The reaction mixture was further cooled to 75-80 ° C. and 250 g of dimethyl sulfate was added slowly with stirring. Once all the dimethyl sulfate has been added, the reaction mixture is brought to 75-80 over about 1 hour to yield 1-methyl-1-((erucylamido-) ethyl) -2-ercylimidazolinium methyl sulfate as the product. Held at 0C.

Preparation of 1-methyl-1- (rapeseed erucate) ethyl) -2- (rapeseed erucate) imidazolinium methyl sulfate (mixture of hydrogenated rapeseed oil dialkylimidazoline at) with nitrogen inlet 1843.6 g (1.88 mol) hydrogenated rapeseed oil and 283.34 g (2.75 mol) diethylenetriamine were placed in a dry stirred pressure vessel. The vessel was purged with nitrogen and heated to 165 ° C. for 5 hours until a baseline value of 76 was reached. The reaction mixture was then heated to 190 ° C. and a vacuum was applied for 5 hours to obtain a tertiary amine content of 94%. The resulting imidazoline intermediate was then cooled to 95 ° C. and 1772 g of cetearyl alcohol was added to function as a solvent. The reaction mixture was further cooled to 85 ° C. and 330 g (2.6 mol) of dimethyl sulfate was slowly added over 30 minutes with stirring. Once all the dimethyl sulfate was added, the reaction mixture was held at 85-90 ° C. for an additional 60 minutes. The resulting pale yellow solid product contained di-hydrogenated rapeseed oil imidazoline at and cetearyl alcohol. The cationic activity of the mixture was 54%. This product could be flaked or pasted.

Preparation of 1-methyl-1-N- (n-propyl) -2-ercylimidazolinium methyl sulfate 1790 g (2.64 mol) of erucic acid and into a dry stirred pressure vessel equipped with a nitrogen inlet and 245 g (2.4 mol) of N- (n-propyl) -N-ethyleneamino) -diamine was added. The vessel was purged with nitrogen and heated to 195 ° C. for 4-5 hours. The reaction mixture was then heated to 190 ° C. and a vacuum was applied for an additional 4-5 hours. The reaction mixture was cooled to 100-105 ° C. and about 1.6 kg cetearyl alcohol was added. The reaction mixture was further cooled to 75-80 ° C. and about 280 g of dimethyl sulfate was added slowly with stirring. Once all of the dimethyl sulfate has been added, the reaction mixture is stirred for about 1 hour to 85-90 to yield 1-methyl-1-N- (n-propyl) -2-ercylimidazolinium methyl sulfate as the product. Held at 0C.

Quat raw material 1
The quat raw material 1 has the following composition.

  The cation activity of the quat raw material 1 is 45%.

Quat raw material 2
The quat raw material 2 has the following composition.

  The cationic activity of the quat raw material 2 is 25%.

Sunscreen lotion Sunscreen lotion contains the following ingredients.

  Sunscreen lotion was prepared as follows. Phase A materials were mixed and heated to 75 ° C. In a separate container, the Phase B material was also mixed and heated to 75 ° C. Phase A was added to phase B with stirring, and the mixed phase was cooled to 40 ° C. with continued stirring. Phase C was added and continued to cool to 25 ° C. to produce the desired lotion.

Sunscreen spray lotion Sunscreen spray lotion contains the following ingredients:

  Sunscreen spray lotion was prepared as follows. Phase A materials were mixed and heated to 75 ° C. In a separate container, the Phase B material was also mixed and heated to 75 ° C. Phase A was added to phase B with stirring, and the mixed phase was cooled to 40 ° C. with continued stirring. Phase C was added and cooling was continued to 25 ° C. to produce the desired lotion.

Hair conditioner The hair conditioner contains the following ingredients.

  A hair conditioner was prepared as follows. Phase A materials were mixed and heated to 75 ° C. In a separate container, the Phase B material was also mixed and heated to 75 ° C. Phase A was added to phase B with stirring, and the mixed phase was cooled to 40 ° C. with continued stirring. Phase C was added and continued to cool to 25 ° C. to produce the desired lotion.

Soft & Shine Conditioner Soft & Shine Conditioner contains the following materials:

Vitamin E-containing conditioner Vitamin E-containing conditioner has the following ingredients.

  The preparation method is as follows. The ingredients of Part A were mixed while mixing and heated to 75-80 ° C. Cool to 35 ° C. and add parts B and C with thorough mixing at once.

Adhesion of vitamin E to hair (Comparative Experiment 1)
Contains either 0.5% vitamin and 1.5% di-behenylimidazolinium methosulfate and cetrimonium methosulfate mixture (7/3 (w / w)) or behentrimonium chloride A simple conditioning formulation was used to treat untreated and decolorized hair bundles. The active ingredient was present at the same level. The hair bundle was washed for 30 seconds and rinsed, and then the attached vitamin E was extracted using a solvent and measured by UV absorbance.

The results are shown below.

Vitamin E adhesion (Comparative Experiment 2)
Conditioning shampoo formulation A and formulation for testing using a mixture of di-behenylimidazolinium methosulfate and cetrimonium metasulfate in a 7/3 (w / w) quat ratio to each other as active conditioning ingredients Product B was prepared. In general, the added conditioning ingredients derived from HEAR oils contained 70% effective quat in cetearyl alcohol with cationic activity. Test formulation A contained 1% quat with cationic activity, and test formulation A contained 0.5% quat with cationic activity. Reference formulation C used polyquaternium-10, a well-known polymer conditioner. A small amount of polyquaternium-10 was used to reflect the cost benefit considerations.

  Hair samples were treated with each conditioning shampoo for 3 minutes and rinsed under 40 ° C. tap water at a flow rate of 2.5 L / min for 20 seconds. Total hair persistence was determined by two successive extractions by PVCS method # 7-1. Only trace amounts of vitamin E were detected in the third extract.

The total hair persistence of the determined vitamin E derived from these conditioning shampoo samples is shown below.

  Conditioning shampoo samples containing di-behenylimidazolinium methosulfate showed better adherence of vitamin E on the hair surface than samples containing polyquaternium-10. Furthermore, the deposition of vitamin E on the hair surface was enhanced by increasing the concentration of di-behenylimidazolinium methosulfate in the formulation.

  Unless stated otherwise, the use of words such as “including”, “containing”, “comprising”, “having”, etc. is used without limitation It is meant to include, and should not be construed as limiting the general statement that it immediately follows a particular or similar item or substance.

Although the invention has been described with reference to particular embodiments, it is to be understood that these embodiments are merely illustrative of the principles and applications of the present invention. Thus, it should be understood that numerous modifications can be made to the exemplary embodiments, and that other formulations can be devised without departing from the spirit and scope of the invention as defined by the appended claims. I must.

Claims (66)

A composition comprising a mixture of dialkyl imidazoline ats, wherein at least a portion of the mixture comprises at least one dialkyl imidazoline at having at least one C ₁₆ -C ₃₀ alkyl group, wherein the C _16-30 substituent of the mixture A composition having a content of about 10% to about 95% relative to the C ₁₀₊ reference substituent range. The composition of claim 1, wherein the _C16-30 substituent content is from about 15% to about 80%. The composition of claim 2, wherein the C _16-30 substituent content is from about 20% to about 70%. 4. The composition of claim 3, wherein the _C16-30 substituent content is from about 35% to about 60%. A composition comprising a mixture of dialkyl imidazoline ats, wherein at least a portion of the mixture comprises at least one dialkyl imidazoline at having at least one C ₂₀ -C ₃₀ alkyl group, wherein the C _20-30 substituent of the mixture A composition having a content of about 10% to about 95% relative to the C ₁₀₊ reference substituent range. 6. The composition of claim 5, wherein the _C20-30 substituent content is from about 15% to about 80%. The composition of claim 6, wherein the _C20-30 substituent content is from about 20% to about 70%. 8. The composition of claim 7, wherein the _C20-30 substituent content is from about 35% to about 60%. A composition comprising a mixture of dialkyl imidazoline ats, wherein at least a portion of the mixture comprises at least one dialkyl imidazoline at having at least one C ₂₀ -C ₂₄ alkyl group, wherein the C _20-24 substituent of the mixture A composition having a content of about 10% to about 95% relative to the C ₁₀₊ reference substituent range. The composition of claim 9, wherein the _C20-24 substituent content is from about 15% to about 80%. 11. The composition of claim 10, wherein the _C20-24 substituent content is from about 20% to about 70%. 12. The composition of claim 11, wherein the _C20-24 substituent content is from about 35% to about 60%.   10. The composition of claim 1, 5 or 9, substantially free of monoalkyl imidazoline at. The dialkyl imidazoline at the mixture is of formula (I):

Wherein X is selected from the group consisting of chloride, bromide, iodide, fluoride, sulfate, methyl sulfate, methanebenzyl sulfate, phosphate, nitrite, nitrate, carboxylate, or mixtures thereof. A salt-forming anion
a is the ionic charge of X;
R ¹ , R ² , and R ³ are independently hydrogen, C ₁ -C ₃₀ alkyl, C ₁ -C ₃₀ alkyl hydroxy, C ₁ -C ₃₀ alkyl amide R ₍ C ₁ -C ₆₎ , C ₁ -C ₃₀ alkyl aryl amides R _(C1-C6) or C ₁ -C ₃₀ alkyl hydroxyamide _{R (C1-C6), R} (C1-C6) is C ₁ -C ₆ alkylene or benzyl,
R ^1, R ^2, and two of R ³ is independently C ₁₀ -C ₃₀ alkyl, C ₁₀ -C ₃₀ alkyl hydroxy, C ₁₀ -C ₃₀ alkyl amido _{R (C1-C6), C} 10 - a C ₃₀ alkylaryl amide R _(C1-C6) or C ₁₀ -C ₃₀ alkyl hydroxy amide R _(C1-C6),
R ^1, R ^2, and the remaining one of R ³ is hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkyl hydroxy, C ₁ -C ₈ alkyl amido _{R (C1-C6), C} 1 a -C ₈ alkylaryl amido R _(C1-C6) or C ₁ -C ₈ alkyl hydroxyamide R _(C1-C6),
R ⁴ , R ⁵ , R ⁶ and R ^{7 which} are the same or different are independently hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy , Hydroxy, or alkoxyhydroxy). R ¹ is C ₁₀ -C ₃₀ alkyl or C ₁₀ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₆ alkyl, and R ³ is C ₁₀ -C ₃₀ alkylamide R _(C1-C6) or C a ₁₀ -C ₃₀ alkyl hydroxy amide _{R (C1-C6), R} 4, R 5, R 6, and R ⁷ are independently hydrogen or C ₁ -C ₈ alkyl, composition of claim 14. R ¹ is C ₁₀ -C ₃₀ alkyl, R ² is methyl, R ³ is C ₁₀ -C ₃₀ alkylhydroxyamide C ₁ -C ₃ alkylene, R ⁴ , R ⁵ , R ⁶ , and R 16. The composition of claim 15, wherein ⁷ is hydrogen and X is chloride or methyl sulfate. R ¹ is C ₁₀ -C ₃₀ alkyl, R ² is methyl, R ³ is C ₁₀ -C ₃₀ alkylamide C ₁ -C ₃ alkylene, R ⁴ , R ⁵ , R ⁶ , and R ⁷ 16. The composition of claim 15, wherein is hydrogen and X is chloride or methyl sulfate. R ³ is C ₁₀ -C ₃₀ alkyl amides ethylene composition of claim 17. For the part of the mixture, R ¹ is C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₁₀ -C ₃₀ alkylamide ₍ a ^{_{C1-C6), R 4,}} R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₁₆ -C ₃₀ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₁₀ -C ₃₀ alkyl or C ₁₀ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₁₆ -C ₃₀ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₂₀ -C ₃₀ alkyl or C ₂₀ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₁₀ -C ₃₀ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₂₀ -C ₃₀ alkyl or C ₂₀ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₂₀ -C ₃₀ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₁₀ -C ₃₀ alkyl or C ₁₀ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₂₀ -C ₃₀ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₂₀ -C ₂₄ alkyl or C ₂₀ -C ₂₄ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₁₀ -C ₃₀ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₂₀ -C ₂₄ alkyl or C ₂₀ -C ₂₄ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₂₀ -C ₂₄ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. For the portion of the mixture, R ¹ is C ₁₀ -C ₃₀ alkyl or C ₁₀ -C ₃₀ alkyl hydroxy, R ² is C ₁ -C ₃ alkyl, and R ³ is C ₂₀ -C ₂₄ alkylamide R a ^{_{(C1-C6), R 4}} , R 5, R 6, and R ⁷ are hydrogen, composition of claim 14. Formula (II):

Wherein X is selected from the group consisting of chloride, bromide, iodide, fluoride, sulfate, methyl sulfate, methanebenzyl sulfate, phosphate, nitrite, nitrate, carboxylate, or mixtures thereof. A salt-forming anion
a is the ionic charge of X;
n varies from 1 to 3,
m is 1 or 2,
The same or different R ⁸ and R ¹¹ are independently C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy;
R ⁹ is hydrogen or C ₁ -C ₃ alkyl;
R ¹⁰ is hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy, or alkoxyhydroxy) mixture of dialkyl imidazoline at Wherein at least a portion of the mixture comprises at least one dialkylimidazoline at least one of R ⁸ and R ¹¹ is C ₁₆ -C ₂₄ alkyl or C ₁₆ -C ₂₄ alkyl hydroxy, composition ₃₀ from about 10% to about 95% with respect to the reference substituents range - C _16-24 substituents content C ₁₆ of the mixture. _30. The composition of claim 28, wherein the _C16-24 substituent content is from about 15% to about 80%. _30. The composition of claim 29, wherein the _C16-24 substituent content is from about 20% to about 70%. _32. The composition of claim 30, wherein the _C16-24 substituent content is from about 35% to about 60%. For dialkylimidazolium link at the said mixture, R ⁹ is C ₁ -C ₃ alkyl, R ¹⁰ is hydrogen, n is 2, m is 2, composition of claim 28. For the dialkyl imidazoline at the portion of the mixture, R ⁸ is C ₁₆ -C ₂₄ alkyl or C ₁₆ -C ₂₄ alkyl hydroxy and R ¹¹ is C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy 35. The composition of claim 32. For the dialkylimidazoline at the portion of the mixture, R ⁸ is C ₁₆ -C ₂₄ alkyl or C ₁₆ -C ₂₄ alkyl hydroxy and R ¹¹ is C ₁₆ -C ₂₄ alkyl or C ₁₆ -C ₂₄ alkyl hydroxy 35. The composition of claim 32. For the dialkyl imidazoline at the portion of the mixture, R ⁸ is C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy and R ¹¹ is C ₁₆ -C ₂₄ alkyl or C ₁₆ -C ₂₄ alkyl hydroxy 35. The composition of claim 32. For the at least one dialkylimidazoline at the portion of the mixture, R ⁸ and R ¹¹ are both linear alkyl radicals of the formula C ₂₁ H ₄₃ , R ⁹ is methyl, R ¹⁰ is hydrogen 29. The composition of claim 28, wherein n is 2 and m is 2. Formula (II):

Wherein X is selected from the group consisting of chloride, bromide, iodide, fluoride, sulfate, methyl sulfate, methanebenzyl sulfate, phosphate, nitrite, nitrate, carboxylate, or mixtures thereof. A salt-forming anion
a is the ionic charge of X;
n varies from 1 to 3,
m is 1 or 2,
The same or different R ⁸ and R ¹¹ are independently C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy;
R ⁹ is hydrogen or C ₁ -C ₃ alkyl;
R ¹⁰ is hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy, hydroxy, or alkoxyhydroxy) mixture of dialkyl imidazoline at Wherein at least a portion of the mixture comprises at least one dialkylimidazoline at least one of R ⁸ and R ¹¹ is C _20-24 alkyl or C _20-24 alkyl hydroxy, A composition wherein the C _20-24 substituent content of the mixture is from about 10% to about 95% relative to the C _16-30 reference substituent range. _38. The composition of claim 37, wherein the _C20-24 substituent content is from about 15% to about 80%. _40. The composition of claim 38, wherein the _C20-24 substituent content is from about 20% to about 70%. _40. The composition of claim 39, wherein the _C20-24 substituent content is from about 35% to about 60%. For dialkylimidazolium link at the mixture, R ⁹ is C ₁ -C ₃ alkyl, R ¹⁰ is hydrogen, n is 2, m is 2, The composition of claim 37. For the dialkyl imidazoline at the portion of the mixture, R ⁸ is C ₂₀ -C ₂₄ alkyl or C ₂₀ -C ₂₄ alkyl hydroxy and R ¹¹ is C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy 42. The composition of claim 41, wherein: For the dialkyl imidazoline at the portion of the mixture, R ⁸ is C ₂₀ -C ₂₄ alkyl or C ₂₀ -C ₂₄ alkyl hydroxy and R ¹¹ is C ₂₀ -C ₂₄ alkyl or C ₂₀ -C ₂₄ alkyl hydroxy 42. The composition of claim 41, wherein: For the dialkyl imidazoline at the portion of the mixture, R ⁸ is C ₁₆ -C ₃₀ alkyl or C ₁₆ -C ₃₀ alkyl hydroxy and R ¹¹ is 20 C ₂₄ alkyl or C ₂₀ -C ₂₄ alkyl hydroxy. Item 42. The composition of Item 41. For the at least one dialkylimidazoline at the portion of the mixture, R ⁸ and R ¹¹ are both linear alkyl radicals of the formula C ₂₁ H ₄₃ , R ⁹ is methyl, R ¹⁰ is hydrogen 38. The composition of claim 37, wherein n is 2 and m is 2. R ⁹ is methyl, composition of claim 27 or 36. R ¹⁰ is hydrogen, A composition according to claim 27 or 36.   37. The composition of claim 27 or 36, wherein n is 2 and m is 2. Formula (IA)

Wherein X is selected from the group consisting of chloride, bromide, iodide, fluoride, sulfate, methyl sulfate, methanebenzyl sulfate, phosphate, nitrite, nitrate, carboxylate, or mixtures thereof. A salt-forming anion
a is the ionic charge of X;
R ^1a , R ^2a , and R ^3a are independently hydrogen, C ₁ -C ₃₆ alkyl, C ₁ -C ₃₆ alkyl hydroxy, C ₁ -C ₃₆ alkyl amide R ₍ C ₁ -C ₆₎ , C ₁ -C ₃₆ alkyl aryl amides R _(C1-C6) or C ₁ -C ₃₆ alkyl hydroxyamide _{R (C1-C6), R} (C1-C6) is C ₁ -C ₆ alkylene or benzyl,
Two of R ^1a , R ^2a , and R ^3a are independently C ₁₀ -C ₃₆ alkyl, C ₁₀ -C ₃₆ alkylhydroxy, C ₁₀ -C ₃₆ alkylamide R _(C1-C6) , C _10- C ₃₆ alkylaryl amide R _(C1-C6) or C ₁₀ -C ₃₆ alkyl hydroxy amide R _(C1-C6),
The remaining one of R ^1a , R ^2a , and R ^3a is hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkyl hydroxy, C ₁ -C ₈ alkyl amide R _(C1-C6) , C ₁ a -C ₈ alkylaryl amido R _(C1-C6) or C ₁ -C ₈ alkyl hydroxyamide R _(C1-C6),
R ⁴ , R ⁵ , R ⁶ and R ^{7 which} are the same or different are independently hydrogen, alkyl, arylalkyl, alkylaryl, fluoro, bromo, chloro, iodo, acetoxy, alkylacetoxy, arylacetoxy, carboxy, alkylcarboxy , Hydroxy, or alkoxyhydroxy) of dialkyl imidazoline at
Where the dialkyl imidazoline is

Wherein R ′ is C ₁₁ -C ₂₂ alkyl or C ₁₃ -C ₂₄ β-alkylhydroxy, R ″ is C ₁ -C ₆ alkyl, and R ′ ″ is C ₁₂ -C ₂₀ alkyl. Or a C _1l -C ₂₂ alkylamide C ₁ -C ₃ alkylene). R ^1a is C ₂₄ -C ₃₆ alkyl, R ^2a is independently hydrogen or C ₁ -C ₃ alkyl, and R ^3a is a structure

Wherein R ^14a, which may be the same as or different from R ^1a , is C ₂₄ -C ₃₆ alkyl, R ⁴ , R ⁵ , R ⁶ , and R ⁷ are all hydrogen, and n is 51. The dialkylimidazoline compound of claim 50, having a range of 1 to 3 and m is 1 or 2.   38. The composition of claim 1, 5, 9, 28, and 37, further comprising at least one hydrophobic component.   52. The composition of claim 51, wherein said at least one hydrophobic component is selected from the group consisting of plant extracts, vitamin E, vitamin A, silicones, waxes and antioxidants.   53. The composition of claim 52, wherein the at least one hydrophobic component is vitamin E.   38. The composition of claim 1, 5, 9, 28, and 37, further comprising one or more preservatives, fragrances, foam enhancers, conditioners and emollients.   38. The composition of claim 1, 5, 9, 28, and 37, further comprising at least one active ingredient present in an amount of about 0.20 to about 40.0% by weight of the composition.   56. The composition of claim 55, wherein the active ingredient is selected from the group consisting of sunscreens, pigments, humectants, film formers, detergents, thickeners, emulsifiers, bactericides, conditioners and deodorants.   38. The composition of claim 1, 5, 9, 28, and 37, further comprising at least one additional surfactant present in an amount of about 1% to about 75% by weight of the composition.   58. The method of claim 57, wherein the additional surfactant is selected from the group consisting of a nonionic surfactant, an anionic surfactant, a cationic surfactant, and an amphoteric surfactant.   38. The composition of claim 1, 5, 9, 28, and 37 which is a raw material quat.   60. The composition of claim 59, further comprising a carrier.   61. The composition of claim 60, having a cationic activity of greater than 20%.   62. The composition of claim 61, wherein the cationic activity is greater than 35%.   64. The composition of claim 62, wherein the cationic activity is greater than 50%.   Cosmetics selected from the group consisting of shampoos, hair conditioners, sunscreen formulations, baby shampoos, baby baths, dishwashing detergents by hand, body soaps, facial cleansers, non-wovens for cosmetics, baby wet tissue and bubble bath products or 38. The composition of claim 1, 5, 9, 28, and 37, which is a personal care product.   65. The composition of claim 64, wherein the cosmetic or personal care product is a non-aqueous topical formulation. 65. The composition of claim 64, wherein the cosmetic or personal care product is an aqueous topical formulation.