JP2017219408A - Indicator for determining sweat smell - Google Patents
Indicator for determining sweat smell Download PDFInfo
- Publication number
- JP2017219408A JP2017219408A JP2016113572A JP2016113572A JP2017219408A JP 2017219408 A JP2017219408 A JP 2017219408A JP 2016113572 A JP2016113572 A JP 2016113572A JP 2016113572 A JP2016113572 A JP 2016113572A JP 2017219408 A JP2017219408 A JP 2017219408A
- Authority
- JP
- Japan
- Prior art keywords
- odor
- carboxylic acid
- sweat
- sweat odor
- mass
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 210000004243 sweat Anatomy 0.000 title claims abstract description 89
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 87
- 239000004753 textile Substances 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 25
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 33
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 238000007865 diluting Methods 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- 238000011156 evaluation Methods 0.000 abstract description 24
- 230000000873 masking effect Effects 0.000 abstract description 4
- 235000019645 odor Nutrition 0.000 description 124
- 239000000047 product Substances 0.000 description 36
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- 150000001875 compounds Chemical class 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
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- 238000004458 analytical method Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 4
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- 102100030530 Suppressor of cytokine signaling 6 Human genes 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
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- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UVECLJDRPFNRRQ-UHFFFAOYSA-N ethyl trifluoromethanesulfonate Chemical compound CCOS(=O)(=O)C(F)(F)F UVECLJDRPFNRRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本発明は、繊維製品から発生する汗臭の判定に用いる指標物質、並びにそれを用いた汗臭の判定方法及び擬似汗臭組成物に関する。 The present invention relates to an indicator substance used for determination of sweat odor generated from a textile product, a method for determining sweat odor using the same, and a pseudo sweat odor composition.
近年、消費者の生活環境への関心の高まりから、身の回りの不快な臭気、例えば職場や通勤時に、人から発生する体臭や衣類等の繊維製品から生じる臭気を気にする人が増えている。特に、着用時の衣類等の繊維製品から発生する臭気は、いわゆる「着用時の汗臭」として不快なニオイとして認識されている。従来、ヒトの汗臭としては、短鎖及び中鎖の複数の脂肪酸臭の寄与が大きいとされてきた。例えば、非特許文献1には、汗臭の主な臭気成分がイソ吉草酸であり、そのほかに炭素数2〜6の脂肪酸が合成体臭として用いられることが記載されている。 In recent years, due to increasing consumer interest in the living environment, an increasing number of people are concerned about unpleasant odors around them, such as body odors generated by people and odors generated from textiles such as clothes during work or commuting. In particular, an odor generated from a textile product such as clothing at the time of wearing is recognized as an unpleasant odor as a so-called “sweat odor at the time of wearing”. Conventionally, it has been considered that the contribution of a plurality of short-chain and medium-chain fatty acid odors is large as a human sweat odor. For example, Non-Patent Document 1 describes that the main odor component of sweat odor is isovaleric acid, and in addition, a fatty acid having 2 to 6 carbon atoms is used as a synthetic odor.
また、短鎖及び中鎖の複数の脂肪酸臭が関与する臭気成分としては、衣類、タオル、寝具等の繊維製品の乾燥が不十分な状態で長時間放置したときに発生しやすい不快な臭いである「生乾き臭」が知られている。この生乾き臭(部屋干し臭)は、中鎖アルデヒド、中鎖アルコール、ケトンなどの「黴様の臭い」、短鎖脂肪酸、中鎖脂肪酸などの「酸っぱい臭い」、窒素化合物などの「生臭い臭い」及び硫黄化合物から構成される複合臭であり、特に中鎖脂肪酸の寄与度が大きいことが報告されている(非特許文献2)。ここでは、生乾き臭の主要成分を「炭素数7〜9の分岐・不飽和を含む脂肪酸の混合物」であると推定し、これらは汗等の臭気にも含まれものとしている。すなわち、非特許文献1、非特許文献2のいずれも、着用時の繊維製品から発生する汗臭特有の成分の存在については、何ら示唆していない。 In addition, as an odor component in which a plurality of short-chain and medium-chain fatty acid odors are involved, an unpleasant odor that is likely to occur when the textiles such as clothes, towels, and bedding are left to dry for a long time. There is a certain “raw odor”. This freshly-dried odor (room-dried odor) is a “smell-like odor” such as medium-chain aldehydes, medium-chain alcohols, and ketones, a “sour odor” such as short-chain fatty acids and medium-chain fatty acids, and a “raw odor” such as nitrogen compounds. In addition, it is reported that the contribution of medium chain fatty acids is large (Non-patent Document 2). Here, it is presumed that the main component of the raw dry odor is “a mixture of fatty acids including branched / unsaturated carbon atoms of 7 to 9”, and these are also included in odors such as sweat. That is, neither Non-Patent Document 1 nor Non-Patent Document 2 suggests the existence of a component peculiar to sweat odor generated from a textile product at the time of wearing.
一方、特許文献1及び2では、洗濯後の繊維製品の乾燥が不十分な状態で発生する不快な臭い(生乾き臭)の原因物質として、4-メチル-3-ヘキセン酸など3種のメチルヘキセン酸を、寄与度が高い物質として開示している。 On the other hand, in Patent Documents 1 and 2, three types of methylhexene such as 4-methyl-3-hexenoic acid are used as causative substances of an unpleasant odor (raw dry odor) that occurs when the textiles after washing are insufficiently dried. The acid is disclosed as a highly contributing substance.
しかしながら、いずれの文献にも、着用時の繊維製品から発生する汗臭特有の成分については、何ら述べられていない。従来、繊維製品から発生する汗臭の判定方法及び汗臭の発生を防止する繊維製品用処理剤製品の有効性評価としては、着用時の臭気と着用後の臭気が同じであると仮定し、着用後の衣類の臭いを嗅いで判断する官能評価試験に依存していた。また、官能評価試験では、評価者の主観的判断が入る余地が大きいため定量的判定が難しく、かつ、客観性に欠けるという問題があった。 However, none of the documents describes a component unique to sweat odor generated from a textile product when worn. Conventionally, as the evaluation method of the sweat odor generated from the textile product and the effectiveness evaluation of the treatment agent product for the textile product that prevents the generation of the sweat odor, it is assumed that the odor at the time of wearing and the odor after wearing are the same, It relied on a sensory evaluation test to determine the smell of clothing after wearing. Further, in the sensory evaluation test, there is a large room for the evaluator's subjective judgment, so that there is a problem that quantitative judgment is difficult and objectivity is lacking.
本発明は、着用時の繊維製品から発生する汗臭を客観的かつ定量的に判定することを可能とする指標物質、及びそれを用いた繊維製品の汗臭判定方法、並びに汗臭マスキング効果等の評価に適した擬似生乾き臭組成物に関する。 The present invention provides an indicator substance that enables objective and quantitative determination of sweat odor generated from a textile product when worn, a sweat odor judgment method for a textile product using the same, and sweat odor masking effect, etc. The present invention relates to a simulated raw dry odor composition suitable for the evaluation of the above.
本発明者らは、着用時の衣類から発生する汗臭を有する衣類の原因成分について研究を行ったところ、特定構造のメチルペンテン酸及びメチルペンタン酸が、汗臭に対する寄与度が大きく、かつ定量し得る濃度で衣類中に存在することを見出し、かつこれらの化合物に構造の近い一群の化合物が、汗臭の程度を定量的に判定する客観的な指標として利用できることを見出した。 The present inventors have studied the causative component of clothing having sweat odor generated from clothing at the time of wearing. As a result, methylpentenoic acid and methylpentanoic acid having a specific structure have a large contribution to sweat odor and are quantitative. It has been found that a group of compounds having a structure close to those compounds can be used as an objective index for quantitatively determining the degree of sweat odor.
本発明は、一般式(1)で表されるカルボン酸及び当該カルボン酸のカルボキシ基に原子又は原子団を導入してなるカルボン酸誘導体よりなる群から選ばれる少なくとも1種を含有する、繊維製品の汗臭判定用指標物質を提供するものである。 The present invention provides a textile product comprising at least one selected from the group consisting of a carboxylic acid represented by the general formula (1) and a carboxylic acid derivative obtained by introducing an atom or an atomic group into the carboxy group of the carboxylic acid. It provides an index substance for determining sweat odor.
〔式中、破線は二重結合であってもよいことを示す。〕 [In the formula, a broken line indicates that it may be a double bond. ]
また本発明は、上記カルボン酸又はその誘導体を指標とする繊維製品の汗臭判定方法を提供するものである。 Moreover, this invention provides the sweat odor determination method of the textiles which uses the said carboxylic acid or its derivative (s) as a parameter | index.
更に本発明は、前記カルボン酸を含有する擬似汗臭組成物を提供するものである。 Furthermore, the present invention provides a pseudo sweat odor composition containing the carboxylic acid.
一般式(1)で表されるカルボン酸は、着用時の繊維製品の汗のニオイに極めて近い臭気を有しており、繊維製品の汗臭判定用指標物質として有用である。従って、当該化合物の存在量を基にして、繊維製品の汗臭の強さを客観的かつ定量的に評価することができる。 The carboxylic acid represented by the general formula (1) has an odor very close to the smell of sweat of the textile product when worn, and is useful as an index substance for determining the sweat odor of the textile product. Therefore, the strength of sweat odor of the textile product can be objectively and quantitatively evaluated based on the amount of the compound.
本発明の汗臭判定用指標物質は、一般式(1)で表されるカルボン酸(以下、カルボン酸(1)と称する)及び当該カルボン酸のカルボキシ基に原子又は原子団を導入してなるカルボン酸誘導体よりなる群から選ばれる少なくとも1種を含有する。 The sweat odor determination indicator substance of the present invention is obtained by introducing an atom or an atomic group into the carboxylic acid represented by the general formula (1) (hereinafter referred to as carboxylic acid (1)) and the carboxy group of the carboxylic acid. It contains at least one selected from the group consisting of carboxylic acid derivatives.
本発明者らが見出した着用時の繊維製品における汗臭の原因物質は、カルボン酸(1)に包含される化合物のうち、下記式(1a)で表される4-メチル-3-ペンテン酸(以下、4M3Pと称す)及び下記式(1b)で表される4-メチルペンタン酸(以下、4MPと称す)であり、いずれも着用時の繊維製品から発する汗臭に極めて近いニオイを持つ。 The causative substance of sweat odor in the textile product when worn by the present inventors, among the compounds included in the carboxylic acid (1), 4-methyl-3-pentenoic acid represented by the following formula (1a) (Hereinafter referred to as 4M3P) and 4-methylpentanoic acid (hereinafter referred to as 4MP) represented by the following formula (1b), both of which have an odor very close to the sweat odor emitted from the textile product when worn.
4M3P(1a)は、工業原料の中間体として知られている化合物であり〔US3082251A〕、4MP(1b)は、フレーバー成分として用いられている化合物であるが、いずれも、汗臭の構成成分として報告されたことはない。また、以下に示す特徴を有することから、汗臭を有する衣類における存在量と存在状態が、着用時の汗臭の程度を示すものと考えられる。 4M3P (1a) is a compound known as an intermediate of industrial raw materials [US3082251A], and 4MP (1b) is a compound used as a flavor component. It has never been reported. Moreover, since it has the characteristic shown below, it is thought that the abundance and the presence state in the clothing which has a sweat odor show the grade of the sweat odor at the time of wear.
(イ)4M3P及び4MPが検出されない着用時の衣類は、汗臭を発生しておらず、反対に4M3P及び4MPが検出される衣類は、汗臭が明らかに発生している。すなわち、以上の2化合物は、着用時の衣類の汗臭に特異的に存在するものである。
(ロ)衣類に含まれる4M3P及び4MPの量が多い衣類ほど、汗臭が強い。
(I) Clothing that does not detect 4M3P and 4MP does not generate sweat odor, while clothing that detects 4M3P and 4MP has obvious sweat odor. That is, the above two compounds exist specifically in the sweat odor of clothing when worn.
(B) Clothing that contains more 4M3P and 4MP in clothing has a stronger sweat odor.
カルボン酸(1)は、上記4M3P及び4MPのほか、化学構造上極めて類似した化合物を包含するものである。4M3P及び4MP以外のカルボン酸(1)の具体例としては、4-メチル-2-ペンテン酸、4-メチル-4-ペンテン酸が挙げられる。 Carboxylic acid (1) includes, in addition to the above 4M3P and 4MP, compounds very similar in chemical structure. Specific examples of the carboxylic acid (1) other than 4M3P and 4MP include 4-methyl-2-pentenoic acid and 4-methyl-4-pentenoic acid.
カルボン酸(1)は、公知の方法で合成可能であり、試薬としても購入できるため、一定品質の合成品を安定供給することで、時と場所を選ばずに汗臭を客観的に評価、判定できる点でも、指標物質として適している。 Since the carboxylic acid (1) can be synthesized by a known method and can be purchased as a reagent, it is possible to objectively evaluate sweat odors regardless of time and place by stably supplying a synthetic product of a certain quality. It is also suitable as an indicator substance because it can be determined.
カルボン酸(1)は、単体であっても、複数のカルボン酸(1)からなる混合物であってもよい。またその純度は高いほど好ましいが、臭気に影響を与えない限り夾雑物を含んでいてもよい。 The carboxylic acid (1) may be a simple substance or a mixture composed of a plurality of carboxylic acids (1). Moreover, although the purity is so preferable that it is high, as long as the odor is not affected, it may contain impurities.
また、カルボン酸(1)は、指標化合物としての検出機能を失わない限り、化学的修飾を施して、すなわちカルボキシ基に原子又は原子団を導入して用いてもよい。例えば、機器分析における分析感度を向上させるために、カルボキシ基をアシル化、エステル化、トリメチルシリル化、アミド化、カルボン酸塩化したり、指標物質を目視化できるようにするために、カルボキシ基に発色団を導入したりすることもできる。 The carboxylic acid (1) may be used after chemical modification, that is, by introducing an atom or an atomic group into the carboxy group, as long as the detection function as an indicator compound is not lost. For example, to improve analytical sensitivity in instrumental analysis, acylation, esterification, trimethylsilylation, amidation, carboxylation of the carboxy group, or coloration of the carboxy group to enable visualization of the indicator substance You can also introduce teams.
誘導体化試薬としては、O-(p-ニトロベンジル)-N,N-ジイソプロピルイソウレア(PNBDI)や、p-ブロモフェナシルブロミド(PBPB)などのUV試薬、4-ブロモメチル-7-メトキシクマリン(Br-MmC)などの蛍光試薬、N-トリメチルシリルイミダゾール(TMSI)やN,O-ビス(トリメチルシリル)アセトアミド(BSA)などのシリル化剤、無水トリフルオロ酢酸やトリフルオロアセチルイミダゾールなどのアシル化剤などを用いることができる。 Derivatizing reagents include UV reagents such as O- (p-nitrobenzyl) -N, N-diisopropylisourea (PNBDI) and p-bromophenacyl bromide (PBPB), 4-bromomethyl-7-methoxycoumarin ( Br-MmC) and other fluorescent reagents, silylating agents such as N-trimethylsilylimidazole (TMSI) and N, O-bis (trimethylsilyl) acetamide (BSA), acylating agents such as trifluoroacetic anhydride and trifluoroacetylimidazole, etc. Can be used.
また、カルボン酸(1)の標識化合物として、可視領域の発色団を用いる場合には、標識化合物の濃度−発色標準サンプルを調製し、サンプルから採取したニオイ抽出物を同じ試薬で発色させたものと比較して、目視で汗臭の程度を判断することも可能である。 When a chromophore in the visible region is used as the labeling compound for carboxylic acid (1), a concentration-coloring standard sample of the labeling compound is prepared, and the odorant extract collected from the sample is colored with the same reagent. It is also possible to judge the degree of sweat odor visually.
呈色反応を利用してカルボン酸(1)の有無や存在量を判定する方法としては、
i)カルボン酸(1)のカルボキシ基に直接発色団を導入する方法
ii)カルボン酸(1)を誘導体に変換した後、誘導体に発色団を導入する方法
iii)カルボン酸(1)を分解した後、分解物に発色団を導入する方法
等が挙げられる。
As a method of determining the presence or amount of carboxylic acid (1) using a color reaction,
i) Method of introducing a chromophore directly into the carboxy group of carboxylic acid (1)
ii) Method of introducing a chromophore into the derivative after converting the carboxylic acid (1) into the derivative
iii) A method of introducing a chromophore into the decomposed product after decomposing the carboxylic acid (1).
i)のカルボン酸(1)のカルボキシ基に直接発色団を導入する方法に用いられる呈色試薬としては、カルボン酸を縮合剤の存在下、発色性の酸ヒドラジドに導いて呈色させる試薬、カルボン酸を発色性のエステルに導いて呈色させる試薬、カルボン酸を発色性のアミドに導いて呈色させる試薬等がある。 As a color reagent used in the method of i) for introducing a chromophore directly into the carboxy group of the carboxylic acid (1), a reagent that introduces a carboxylic acid into a chromogenic acid hydrazide in the presence of a condensing agent to cause coloration; There are a reagent for introducing a carboxylic acid into a chromogenic ester to cause coloration, a reagent for introducing a carboxylic acid into a chromogenic amide for coloring, and the like.
カルボン酸を発色性の酸ヒドラジドに導いて呈色させる試薬としては、2-ニトロフェニルヒドラジン、6,7-ジメトキシ-1-メチル-2(1H)-キノキサリノン-3-プロピオニルカルボン酸ヒドラジド(DMEQ-H)、p-(4,5-ジフェニル-1H-イミダゾール-2-イル)-ベンゾヒドラジド、p-(1-メチル-1H-フェナントロ-[9,10-イミダゾール-2-イル)-ベンゾヒドラジド、p-(5,6-ジメトキシ-2-ベンゾチアゾイル)-ベンゾヒドラジド等が挙げられる。 Reagents that lead carboxylic acid to chromogenic acid hydrazide for coloration include 2-nitrophenylhydrazine, 6,7-dimethoxy-1-methyl-2 (1H) -quinoxalinone-3-propionylcarboxylic acid hydrazide (DMEQ- H), p- (4,5-diphenyl-1H-imidazol-2-yl) -benzohydrazide, p- (1-methyl-1H-phenanthro- [9,10-imidazol-2-yl) -benzohydrazide, and p- (5,6-dimethoxy-2-benzothiazoyl) -benzohydrazide.
カルボン酸を発色性のエステルに導いて呈色させる試薬としては、9-アンスリルジアゾメタン、1-ナフチルジアゾメタン、1-(2-ナフチル)ジアゾエタン、1-ピレニルジアゾメタン、4-ジアゾメチル-7-メトキシクマリン、4-ブロモメチル-7-メトキシクマリン、3-ブロモメチル-6,7-ジメトキシ-1-メチル-2(1H)-キノキザリノン、9-ブロモメチルアクリジン、4-ブロモメチル-6,7-メチレンジオキシクマリン、N-(9-アクリジニル)-ブロモアセトアミド、2-(2,3-ナフチルイミノ)エチルトリフルオロメタンスルホネート、2-(フタルイミノ)エチルトリフルオロメタンスルホネート、N-クロロメチルフタルイミド、N-クロロメチル-4-ニトロフタルイミド、N-クロロメチルイサチン、o-(p-ニトロベンジル)-N,N'-ジイソプロピルイソウレア等が挙げられる。 Reagents for introducing a carboxylic acid into a chromogenic ester to cause coloration include 9-anthryldiazomethane, 1-naphthyldiazomethane, 1- (2-naphthyl) diazoethane, 1-pyrenyldiazomethane, 4-diazomethyl-7-methoxy. Coumarin, 4-bromomethyl-7-methoxycoumarin, 3-bromomethyl-6,7-dimethoxy-1-methyl-2 (1H) -quinoxalinone, 9-bromomethylacridine, 4-bromomethyl-6,7-methylenedioxycoumarin N- (9-acridinyl) -bromoacetamide, 2- (2,3-naphthylimino) ethyl trifluoromethanesulfonate, 2- (phthalimino) ethyl trifluoromethanesulfonate, N-chloromethylphthalimide, N-chloromethyl-4-nitro Examples include phthalimide, N-chloromethyl isatin, o- (p-nitrobenzyl) -N, N′-diisopropylisourea and the like.
カルボン酸を発色性のアミドに導いて呈色させる試薬としては、モノダンシルカダベリン、2-(p-アミノメチルフェニル)-N,N'-ジメチル-2H-ベンゾトリアゾール-5-アミン等が挙げられる。 Examples of the reagent that introduces a carboxylic acid into a chromogenic amide to cause coloration include monodansylcadaverine, 2- (p-aminomethylphenyl) -N, N′-dimethyl-2H-benzotriazol-5-amine, and the like. .
ii)のカルボン酸を誘導体に変換した後、誘導体に発色団を導入する方法において、呈色反応に利用できるカルボン酸の誘導体としては、無機塩、酸クロライド等が挙げられる。 In the method of converting the carboxylic acid of ii) to a derivative and then introducing a chromophore into the derivative, examples of the carboxylic acid derivative that can be used for the color reaction include inorganic salts and acid chlorides.
カルボン酸の無機塩は芳香族ハロゲンと反応させて発色性のエステルに、酸クロライドは発色性のアミドに、それぞれ誘導することができる。カルボン酸を無機塩に変換する方法としては、カルボン酸を炭酸水素ナトリウム溶液、炭酸ナトリウム溶液、水酸化ナトリウム溶液、水酸化カリウム溶液等のアルカリ性物質と混合して中和する方法が挙げられる。ヒドロキシカルボン酸の無機塩と反応し、発色性のエステルに誘導できる芳香族ハロゲンとしては、p-ニトロベンジルブロミド、フェナシルブロミド、p-クロロフェナシルブロミド、p-ブロモフェナシルブロミド、p-ヨードフェナシルブロミド、p-ニトロフェナシルブロミド、p-フェニルフェナシルブロミド、p-フェニルアゾフェナシルブロミド、N,N'-ジメチル-p-アミノベンゼンアゾフェナシルクロライド等が挙げられる。 Carboxylic acid inorganic salts can be reacted with aromatic halogens to give chromogenic esters and acid chlorides to chromogenic amides. Examples of the method for converting the carboxylic acid into an inorganic salt include a method in which the carboxylic acid is mixed with an alkaline substance such as a sodium hydrogen carbonate solution, a sodium carbonate solution, a sodium hydroxide solution, a potassium hydroxide solution and neutralized. Aromatic halogens that can be converted to chromogenic esters by reacting with inorganic salts of hydroxycarboxylic acids include p-nitrobenzyl bromide, phenacyl bromide, p-chlorophenacyl bromide, p-bromophenacyl bromide, p-iodo Examples include phenacyl bromide, p-nitrophenacyl bromide, p-phenylphenacyl bromide, p-phenylazophenacyl bromide, N, N'-dimethyl-p-aminobenzeneazophenacyl chloride.
カルボン酸を酸クロライドに変換する方法としては、カルボン酸をオキザリルクロライドと反応させる方法等が挙げられる。酸クロライドを発色性のアミドに導く方法としては、トリエチルアミンの存在下、9-アミノフェナントレンと反応させる方法等が挙げられる。 Examples of the method for converting carboxylic acid to acid chloride include a method of reacting carboxylic acid with oxalyl chloride. Examples of the method for converting the acid chloride to a color-forming amide include a method of reacting with 9-aminophenanthrene in the presence of triethylamine.
iii)のカルボン酸を分解した後、その分解物に対して発色団を導入する方法としては、カルボン酸にアデノシン三リン酸(ATP)と補酵素CoAの存在のもとで、アシル-CoAシンテターゼを作用させて、アシル-CoAを生成せしめ、次にアシル-CoAオキシダーゼで処理して、エノイル-CoAと過酸化水素を生成せしめ、更に過酸化水素をカタラーゼで処理してホルムアルデヒドにし、これに呈色試薬である4-アミノ-3-ヒドラジノ-5-メルカプト-1,2,3-トリアゾール(AHMT)を反応させて、生じる紫色を比色する方法が挙げられる。 After degrading the carboxylic acid of iii), a chromophore can be introduced into the degradation product by acyl-CoA synthetase in the presence of adenosine triphosphate (ATP) and coenzyme CoA in the carboxylic acid. To produce acyl-CoA, then treated with acyl-CoA oxidase to produce enoyl-CoA and hydrogen peroxide, which is further treated with catalase to formaldehyde. There is a method in which a color reagent, 4-amino-3-hydrazino-5-mercapto-1,2,3-triazole (AHMT), is reacted to colorize the resulting purple color.
このように、本発明において、カルボン酸の呈色反応に用いられる試薬は、カルボン酸、カルボン酸誘導体、カルボン酸分解物のいずれかと反応して発色するものであれば特に限定されない。すなわちカルボン酸(1)を呈色化する汗臭判定試薬は、ガスクロマトグラフィーや液体クロマトグラフィー等の高価な分析機器を用いることなく、汗臭の程度を確実で迅速かつ簡単に判定することが可能であるので、特別な分析機器が無い環境において判定する場合に利用することができる。 Thus, in the present invention, the reagent used for the color reaction of the carboxylic acid is not particularly limited as long as it reacts with any of carboxylic acid, a carboxylic acid derivative, and a carboxylic acid decomposition product to develop a color. In other words, the sweat odor judging reagent that colors carboxylic acid (1) can reliably and quickly judge the degree of sweat odor without using expensive analytical instruments such as gas chromatography and liquid chromatography. Since it is possible, it can be used when determining in an environment where there is no special analytical instrument.
本発明においては、これらの指標物質を用いて、繊維製品における汗臭の程度について定量的に判定することが可能となる。 In the present invention, it is possible to quantitatively determine the degree of sweat odor in the textile product using these indicator substances.
カルボン酸(1)又はその誘導体を汗臭判定用指標物質として使用する方法としては、例えば、GC-MSで測定する場合には、カルボン酸(1)又はその誘導体を標準物質(スタンダード)として検量線を作成し、その検量線を使用して、採取した衣類に含まれるカルボン酸(1)のピークを同定し、その量を測定すればよい。 As a method of using carboxylic acid (1) or a derivative thereof as an index substance for determining sweat odor, for example, when measuring by GC-MS, calibration is performed using carboxylic acid (1) or a derivative thereof as a standard substance (standard). A line is prepared, and the calibration curve is used to identify the peak of carboxylic acid (1) contained in the collected clothing and measure the amount.
また、官能評価を行う場合には、カルボン酸(1)を数段階に希釈して各濃度のニオイ標準サンプルを調製し、汗臭を有する衣類から調製した評価サンプルのニオイを標準サンプルと照合し、衣類に含まれるカルボン酸(1)の量を官能評価により判定すればよい。このようにして衣類の汗臭を、ニオイ又はニオイ以外のパラメータを利用して定量的に判定することでその程度を判定する。 When performing sensory evaluation, prepare odor standard samples of various concentrations by diluting carboxylic acid (1) in several stages, and check the odor of the evaluation sample prepared from clothing with sweat odor against the standard sample. The amount of carboxylic acid (1) contained in clothing may be determined by sensory evaluation. In this way, the degree of sweat odor of clothing is determined by quantitatively using odors or parameters other than odors.
また、衣類においてカルボン酸(1)の生成量が多いにもかかわらず、それが塩等のニオイが無い又は弱い誘導体に変化している場合、汗臭の潜在状態が存在しているにもかかわらず、官能評価では汗臭の潜在状態を正確に評価できない場合がある。これに対して、本発明では、必要な化学処理によって分析可能なカルボン酸(1)あるいはそれらの誘導体を測定することによって、評価サンプルが汗臭を発生させる可能性のあるサンプルかどうか、すなわち、ポテンシャル評価を行うことができる。 In addition, when the amount of carboxylic acid (1) produced in clothing is large but it has no odor such as salt or has changed to a weak derivative, a sweat odor latent state exists, In some cases, the sensory evaluation cannot accurately evaluate the latent state of sweat odor. On the other hand, in the present invention, by measuring the carboxylic acid (1) or a derivative thereof that can be analyzed by a necessary chemical treatment, whether the evaluation sample is a sample that may generate a sweat odor, that is, Potential evaluation can be performed.
本発明の指標物質は、前述したように化学分析、機器分析又は官能評価等のいずれにも利用され客観性の高い定量的判定が可能となるが、特に、化学分析や機器分析等により、測定値をカルボン酸(1)の存在量で表現することで、判定結果から主観性を排除することが可能である。 As described above, the index substance of the present invention can be used for any of chemical analysis, instrumental analysis, sensory evaluation, etc. and can be quantitatively determined with high objectivity. By expressing the value as the abundance of carboxylic acid (1), it is possible to exclude subjectivity from the determination result.
更に本発明においては、汗臭をターゲットとする繊維製品用処理剤製品の有効性を、カルボン酸(1)又はその誘導体を含有する指標物質を用い、客観的かつ定量的に判定することができる。 Furthermore, in the present invention, the effectiveness of the treatment product for textile products targeting sweat odor can be objectively and quantitatively determined using an indicator substance containing carboxylic acid (1) or a derivative thereof. .
繊維製品用処理剤製品の有効性を判定する方法においては、前記指標物質を単体として使用するか、又は他の成分、例えば溶解又は希釈のための溶剤や、安定剤、抗菌剤、抗菌剤、界面活性剤、酸化防止剤、香料、植物抽出物等の添加剤を配合し、保存や判定試験での使用等の実用に即した組成物に調製して用いることができる。 In the method for determining the effectiveness of a treatment product for textile products, the indicator substance is used as a simple substance, or other components such as a solvent for dissolution or dilution, a stabilizer, an antibacterial agent, an antibacterial agent, Additives such as surfactants, antioxidants, fragrances, plant extracts and the like can be blended and used in preparations for practical use such as storage and use in judgment tests.
汗臭をターゲットとする繊維製品用処理剤としては、例えば、衣類に付着した菌を殺菌することにより衣類に残存した汗、皮脂などの分解を抑制する処理剤、ニオイ成分をにおわない誘導体に分解又は変化させる処理剤、或いは、ニオイをマスキングする処理剤等の効果を有する処理剤が挙げられる。カルボン酸(1)又はその誘導体を繊維製品用処理剤製品の有効性判定用指標物質として使用するには、繊維製品用処理剤製品の作用機序及び評価方式に適合させて用いればよい。 Examples of treatment agents for textile products that target sweaty odors include treatment agents that suppress the decomposition of sweat, sebum, etc. remaining in clothing by sterilizing bacteria attached to clothing, and decompose into odorless derivatives. Or the processing agent which has effects, such as the processing agent to change or the processing agent which masks odor, is mentioned. In order to use the carboxylic acid (1) or a derivative thereof as an index substance for determining the effectiveness of a fiber product treating agent product, the carboxylic acid (1) may be used in conformity with the action mechanism and evaluation method of the fiber product treating agent product.
具体的には、有効成分としてカルボン酸(1)又はその誘導体、好ましくは4M3P、4MP又はそれらの誘導体を所定濃度で含有する指標物質を衣類等の繊維に付着させ、所定量の繊維製品用処理剤サンプルを添加し、指標物質の変化状態を適切な方法で定量することで、繊維製品用処理剤サンプルの有効性を客観的かつ定量的に判定できる。 Specifically, a carboxylic acid (1) or a derivative thereof, preferably 4M3P, 4MP or a derivative thereof as an active ingredient is attached to a fiber such as clothing, and a predetermined amount of the fiber product is treated. By adding the agent sample and quantifying the change state of the indicator substance by an appropriate method, the effectiveness of the treatment agent sample for textile products can be objectively and quantitatively determined.
指標物質の変化状態を定量する方法の具体例としては、カルボン酸(1)を分解又は別の化合物に誘導してニオイを減じる繊維製品用処理剤サンプルである場合、指標物質の検量線を予め作成しておき、この検量線を用いて機器分析を行うか、指標物質の変化体又は未変化体を滴定又は抽出等の化学分析により定量する。また、汗臭をマスキングする繊維製品用処理剤サンプルである場合、指標物質を数段階に希釈して各濃度のニオイ標準サンプルを調製し、繊維製品用処理剤サンプルを添加した指標物質のニオイを標準サンプルと照合し、マスキング効果を官能評価により判定する。 As a specific example of the method for quantifying the change state of the indicator substance, in the case of a fiber product treatment sample that decomposes or induces carboxylic acid (1) into another compound to reduce odor, a calibration curve of the indicator substance is previously set. It is prepared and an instrumental analysis is performed using this calibration curve, or a changed or unchanged substance of the indicator substance is quantified by chemical analysis such as titration or extraction. In the case of a textile treatment agent sample that masks sweat odor, prepare an odor standard sample of each concentration by diluting the indicator substance in several stages, and then add the odor of the indicator substance to which the textile agent treatment sample is added. The masking effect is judged by sensory evaluation against a standard sample.
更に本発明は、カルボン酸(1)を含有し、汗臭の消臭やマスキング効果の評価に使用できる擬似汗臭組成物を提供するものである。この擬似汗臭組成物を使用することにより、消臭基剤のスクリーニングや、消臭剤組成物の汗臭の消臭効果を正確にかつ再現性よく評価することができる。 Furthermore, the present invention provides a pseudo sweat odor composition which contains carboxylic acid (1) and can be used for deodorizing sweat odor and evaluating the masking effect. By using this pseudo sweat odor composition, the screening of a deodorant base and the deodorant effect of the sweat odor of the deodorant composition can be evaluated accurately and with good reproducibility.
官能評価などにおける汗臭判定のためにこのカルボン酸(1)を用いる場合には、既知の汗臭構成成分を所定の比率で混合することで、更に実場面に近い汗臭を再現できる。すなわち、本発明の擬似生乾き臭組成物は、カルボン酸(1)を成分(A)として含有し、これに以下に示される成分(B)及び(C)の化合物を適宜含有させることができる。成分(A)は、少なくとも4M3P及び4MPのいずれかを含むことが好ましい。擬似汗臭組成物中における成分(A)の含有量は、好ましくは0.5質量%以上、より好ましくは1質量%以上であり、また、好ましくは60質量%以下、より好ましくは56質量%以下である。 When this carboxylic acid (1) is used for determination of sweat odor in sensory evaluation or the like, sweat odor closer to the actual situation can be reproduced by mixing known sweat odor components at a predetermined ratio. That is, the simulated raw dry odor composition of the present invention contains carboxylic acid (1) as component (A), and can appropriately contain the compounds of components (B) and (C) shown below. Component (A) preferably contains at least one of 4M3P and 4MP. The content of the component (A) in the pseudo sweat odor composition is preferably 0.5% by mass or more, more preferably 1% by mass or more, and preferably 60% by mass or less, more preferably 56% by mass or less. is there.
成分(B)は、炭素鎖数2〜5の低級脂肪酸であり、これらの化合物を組成物に加えることにより、汗様の酸っぱい臭いが付与され、着用時の繊維製品から発生する汗臭により近づけることができる。成分(B)としては、例えば酢酸、プロピオン酸、酪酸、2-メチル酪酸、吉草酸、イソ吉草酸が挙げられ、いずれかを単独で又は2種以上を組み合わせて使用することができる。擬似汗臭組成物中における成分(B)の含有量は、好ましくは0.1質量%以上、より好ましくは0.5質量%以上であり、また、好ましくは60質量%以下、より好ましくは55質量%以下である。 Component (B) is a lower fatty acid having 2 to 5 carbon chains, and by adding these compounds to the composition, a sweat-like sour odor is imparted, which is closer to the sweat odor generated from the fiber product when worn. be able to. Examples of the component (B) include acetic acid, propionic acid, butyric acid, 2-methylbutyric acid, valeric acid, and isovaleric acid, and any of these can be used alone or in combination of two or more. The content of the component (B) in the pseudo sweat odor composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and preferably 60% by mass or less, more preferably 55% by mass or less. is there.
本発明において、成分(A)に対する成分(B)の質量比(B)/(A)は、好ましくは0.005以上、より好ましくは0.01以上であり、また、好ましくは50以下、より好ましくは25以下である。 In the present invention, the mass ratio (B) / (A) of the component (B) to the component (A) is preferably 0.005 or more, more preferably 0.01 or more, and preferably 50 or less, more preferably 25 or less. It is.
成分(C)は、炭素数7の飽和又は不飽和のメチル分岐脂肪酸であり、これらの化合物を組成物に加えることにより、着用時の繊維製品から発生する特有の汗様臭気が付与され、実際の着用時に発する汗臭により近づけることができる。成分(C)としては、例えば4-メチル-3-ヘキセン酸(4M3H)、4-メチルヘキサン酸(4MH)、5-メチル-2-ヘキセン酸(5M2H)、5-メチル-4-ヘキセン酸(5M4H)などが挙げられ、いずれかを単独で又は2種以上を組み合わせて使用することができる。擬似汗臭組成物中における成分(C)の含有量は、好ましくは0.01質量%以上、より好ましくは0.05質量%以上であり、また、好ましくは15質量%以下、より好ましくは10質量%以下である。 Component (C) is a saturated or unsaturated methyl-branched fatty acid having 7 carbon atoms, and by adding these compounds to the composition, a specific sweat-like odor generated from the textile product at the time of wearing is imparted. It can be brought closer to the sweat odor that is emitted when wearing. Examples of the component (C) include 4-methyl-3-hexenoic acid (4M3H), 4-methylhexanoic acid (4MH), 5-methyl-2-hexenoic acid (5M2H), 5-methyl-4-hexenoic acid ( 5M4H) and the like, and any of them can be used alone or in combination of two or more. The content of the component (C) in the pseudo sweat odor composition is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and preferably 15% by mass or less, more preferably 10% by mass or less. is there.
本発明において、成分(A)に対する成分(C)の質量比(C)/(A)は、好ましくは0.001以上、より好ましくは0.01以上であり、また、好ましくは10以下である。 In the present invention, the mass ratio (C) / (A) of the component (C) to the component (A) is preferably 0.001 or more, more preferably 0.01 or more, and preferably 10 or less.
また、本発明の擬似汗臭組成物は、更に成分(D)として、ヒト皮脂や汗から検出される炭素鎖6〜12の直鎖飽和脂肪酸を含むことが、ヒト由来の臭い特有の甘さやこもったような酸臭を付与でき、着用時の繊維製品から発生する汗臭により近づけることができるため、好ましい。成分(D)は、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、ウンデカン酸及びドデカン酸から選ばれ、いずれかを単独で又は2種以上を組み合わせて使用することができる。擬似汗臭組成物中における成分(D)の含有量は、好ましくは0.5質量%以上、より好ましくは5質量%以上であり、また、好ましくは70質量%以下、より好ましくは60質量%以下である。 Further, the pseudo sweat odor composition of the present invention further contains, as component (D), a straight chain saturated fatty acid having 6 to 12 carbon chains detected from human sebum or sweat, and has a sweetness peculiar to human odors. It is preferable because it can give an acid odor like a stagnation, and can be made closer to a sweat odor generated from a textile product when worn. Component (D) is selected from hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid and dodecanoic acid, and any one of them can be used alone or in combination of two or more. The content of component (D) in the pseudo sweat odor composition is preferably 0.5% by mass or more, more preferably 5% by mass or more, and preferably 70% by mass or less, more preferably 60% by mass or less. is there.
成分(A)に対する成分(D)の質量比(D)/(A)は、好ましくは0.01以上、より好ましくは0.1以上であり、また、好ましくは100以下、より好ましくは50以下である。 The mass ratio (D) / (A) of the component (D) to the component (A) is preferably 0.01 or more, more preferably 0.1 or more, and preferably 100 or less, more preferably 50 or less.
本発明の擬似汗臭組成物は、成分(A)〜(D)以外の化合物、例えばピラジン類、ピリジン類、ジメチルジスルフィド、ジメチルトリスルフィド等のカビ臭由来の化合物、ミリスチン酸、パルミチン酸、パルミトイル酸、ステアリン酸、オレイン酸、リノール酸等の高級脂肪酸を含むことで、更に実際の汗臭により近づけることができる。 The pseudo sweat odor composition of the present invention comprises compounds other than components (A) to (D), such as compounds derived from mold odor such as pyrazines, pyridines, dimethyl disulfide, dimethyl trisulfide, myristic acid, palmitic acid, palmitoyl. By containing higher fatty acids such as acid, stearic acid, oleic acid and linoleic acid, it can be made closer to the actual sweat odor.
また、本発明の擬似汗臭組成物には、必要に応じて、水、ジエチルフタレート、ジプロピレングルコール、プロピレングルコール、トリエチルシトレート、ブチルジグリコール等の希釈剤やエタノールなどの溶剤を含有させることができる。その量は、本発明の擬似汗臭組成物の使用対象、使用目的等に応じて適宜決定することができる。 Further, the simulated sweat odor composition of the present invention contains a diluent such as water, diethyl phthalate, dipropylene glycol, propylene glycol, triethyl citrate, butyl diglycol or a solvent such as ethanol, if necessary. Can be made. The amount can be appropriately determined according to the intended use and intended purpose of the simulated sweat odor composition of the present invention.
また、本発明の疑似汗臭組成物は、前記指標物質であるカルボン酸(1)を用いた場合と同様に、繊維製品の汗臭強度の評価に用いることができる。例えば、疑似汗臭組成物を数段階に希釈して各濃度のニオイ標準サンプルを調製し、汗臭を有する衣類から調製した評価サンプルのニオイを標準サンプルと照合し、衣類に付着したニオイの強度を官能評価により定量的に測定できる。更に、これらの組成物は、混合臭の消臭をターゲットとするデオドランド剤、介護臭の消臭用、室内消臭剤、衣料用洗浄剤、衣料用消臭剤、住居用洗浄剤等の洗浄剤などの開発に応用してもよい。 Further, the pseudo sweat odor composition of the present invention can be used for the evaluation of the sweat odor strength of a textile product in the same manner as when the carboxylic acid (1) as the indicator substance is used. For example, the simulated sweat odor composition is diluted in several stages to prepare odor standard samples of each concentration, and the odor of the evaluation sample prepared from clothing with sweat odor is checked against the standard sample, and the strength of the odor attached to the clothing Can be quantitatively measured by sensory evaluation. In addition, these compositions can be used to clean deodorants, deodorants for nursing odors, indoor deodorants, clothing cleaners, clothing deodorants, residential cleaners, etc. It may be applied to the development of agents.
試験例1
汗臭が発生した衣類10gを細かく裁断してジエチルエーテル30mLに浸漬し、約15分間超音波をかけてニオイ成分抽出液を得た。ニオイ成分抽出液をフィルタ−濾過(0.4ミクロン孔)したのち、1N NaOH水溶液を10mL添加してよく撹拌した。静置分層後に上層のジエチルエーテル層を除き、残った下層(水層)に新しいジエチルエーテル10mLを添加してよく撹拌し、静置分層後に上層のジエチルエーテルを除いた。下層(水層)にジエチルエーテル3mLを添加したのち、塩酸を加えて中和させ、上層(ジエチルエーテル/遊離脂肪酸を含む)をフィルター濾過(0.2ミクロン孔)し、分析用のサンプルとした。
分析用サンプルについて、匂い嗅ぎGCを行い、汗臭様のニオイをもつ成分のGC保持時間(RT:Retention time)を特定した。続いて、分析用サンプルをGERSTEL社の大量注入ユニット(CIS4)をアジレント社製GC-MSに接続した装置にて分析を行い、汗臭様のニオイをもつ成分の解析を行った。それぞれの分析条件を示す。
Test example 1
10 g of clothing with sweaty odor was cut into fine pieces, soaked in 30 mL of diethyl ether, and sonicated for about 15 minutes to obtain an odor component extract. After the odor component extract was filtered and filtered (0.4 micron pore), 10 mL of 1N NaOH aqueous solution was added and stirred well. After the stationary separation layer, the upper diethyl ether layer was removed, and 10 mL of fresh diethyl ether was added to the remaining lower layer (aqueous layer) and stirred well. After the stationary separation layer, the upper diethyl ether layer was removed. After 3 mL of diethyl ether was added to the lower layer (aqueous layer), the mixture was neutralized by adding hydrochloric acid, and the upper layer (including diethyl ether / free fatty acid) was filtered (0.2 micron pore) to obtain a sample for analysis.
The sample for analysis was subjected to smell sniffing GC, and the GC retention time (RT: Retention time) of the component having sweat-like odor was specified. Subsequently, the sample for analysis was analyzed with a device in which a mass injection unit (CIS4) manufactured by GERSTEL was connected to GC-MS manufactured by Agilent, and components having sweat-like odor were analyzed. Each analysis condition is shown.
匂い嗅ぎGC条件
GC:Agilent 6890N
カラムDB-1(商品名、アジレント社製)、長さ30m、内径530μm、膜厚 1.0μm
40℃-2℃/min-280℃(30min.)
大量注入ユニット(CIS4)条件:
サンプル50μL注入後0℃で溶媒をベントした後、180℃でインジェクション
GC-MS条件:
GC:Agilent 6890N(商品名、アジレント社製)
MS:Agilent 5975(商品名、アジレント社製)
TDS脱着条件:250℃、パージ流量50mL/min、パージ時間3min.
カラム:DB-1(商品名、アジレント社製)、長さ60m、内径250μm、膜厚0.25μm
30℃(6min.)−10℃/min−60℃−5℃/min−95℃−3℃/min−300℃
Smell GC conditions
GC: Agilent 6890N
Column DB-1 (trade name, manufactured by Agilent), length 30 m, inner diameter 530 μm, film thickness 1.0 μm
40 ℃ -2 ℃ / min-280 ℃ (30min.)
Mass injection unit (CIS4) conditions:
After injecting 50 μL of sample, vent the solvent at 0 ° C, then inject at 180 ° C
GC-MS conditions:
GC: Agilent 6890N (trade name, manufactured by Agilent)
MS: Agilent 5975 (trade name, manufactured by Agilent)
TDS desorption conditions: 250 ° C, purge flow rate 50mL / min, purge time 3min.
Column: DB-1 (trade name, manufactured by Agilent), length 60 m, inner diameter 250 μm, film thickness 0.25 μm
30 ℃ (6min.)-10 ℃ / min-60 ℃ -5 ℃ / min-95 ℃ -3 ℃ / min-300 ℃
解析の結果、特徴的な汗臭様のニオイをもつ成分として、4M3P及び4MPの2種類のカルボン酸が同定された。それぞれの化合物の同定は、別途、試薬として購入した標準品と、GC保持時間及び検出された成分のマスフラグメントイオン(m/z(+))を比較することにより行った。2種のカルボン酸のm/z(+)は以下のとおりである。
4-メチル-3-ペンテン酸(4M3H)のm/z(+):41(82), 42(8), 43(10), 45(7), 53(14), 55(13), 67(11), 68(16), 69(100), 81(3), 96(7), 114(48)
4-メチルペンタン酸(4MP)のm/z(+):41(45), 42(11), 43(45), 45(14), 55(53), 56(16), 57(100), 59(15), 60(30), 73(63), 74(64), 83(20), 87(7), 101(5), 115(0.32), 116(0.03)
As a result of the analysis, two types of carboxylic acids, 4M3P and 4MP, were identified as components with characteristic sweaty odor. Each compound was identified by separately comparing a standard product purchased as a reagent with a GC retention time and a detected mass fragment ion (m / z (+)) of the component. The m / z (+) of the two carboxylic acids is as follows.
4-methyl-3-pentenoic acid (4M3H) m / z (+): 41 (82), 42 (8), 43 (10), 45 (7), 53 (14), 55 (13), 67 (11), 68 (16), 69 (100), 81 (3), 96 (7), 114 (48)
4-methylpentanoic acid (4MP) m / z (+): 41 (45), 42 (11), 43 (45), 45 (14), 55 (53), 56 (16), 57 (100) , 59 (15), 60 (30), 73 (63), 74 (64), 83 (20), 87 (7), 101 (5), 115 (0.32), 116 (0.03)
それぞれの化合物のニオイについて、専門評価者による官能評価を行った。結果を表1に示す。 A sensory evaluation by a professional evaluator was performed on the odor of each compound. The results are shown in Table 1.
実施例1〜7、比較例1
表2に示す擬似汗臭組成物を調製し、下記の評価方法に基づいて官能評価を行った。表2中の各成分の含有量は質量%である。
(評価方法)
室温(25℃)、湿度65%の環境に保たれた室内にて、5×5cmの未使用のタオル(木綿製)に、各擬似汗臭組成物をイオン交換水にて1000倍に希釈したものを0.1mL塗布した。このタオルのニオイがどの程度汗臭に近いかについて、4人の専門評価者によって、10段階の官能評価(10:非常に汗臭的なニオイ〜1:汗臭のニオイではない)を行い、その平均値を表2に示した。
Examples 1-7, Comparative Example 1
The pseudo sweat odor composition shown in Table 2 was prepared, and sensory evaluation was performed based on the following evaluation method. The content of each component in Table 2 is mass%.
(Evaluation method)
Each simulated sweat odor composition was diluted 1000 times with ion-exchanged water in a 5 x 5 cm unused towel (made of cotton) in a room maintained at room temperature (25 ° C) and humidity of 65%. 0.1 mL was applied. About how close the smell of this towel is to the sweaty odor, 10 expert evaluations (10: very sweaty odor-1: not the smell of sweaty odor) are performed by 4 expert evaluators, The average value is shown in Table 2.
Claims (7)
(A) 一般式(1)で表されるカルボン酸
(A) Carboxylic acid represented by the general formula (1)
(B) 炭素数2〜5の低級脂肪酸
(C) 炭素数7の飽和又は不飽和のメチル分岐脂肪酸 Furthermore, the pseudo sweat odor composition of Claim 4 containing the following component (B) and (C).
(B) C2-C5 lower fatty acid
(C) C7 saturated or unsaturated methyl branched fatty acid
(D) 炭素数6〜12の直鎖の飽和脂肪酸 Furthermore, the pseudo sweat odor composition of any one of Claims 4-6 containing the following component (D).
(D) C6-C12 linear saturated fatty acid
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