TWI778497B - 胺基酸界面活性劑 - Google Patents
胺基酸界面活性劑 Download PDFInfo
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- TWI778497B TWI778497B TW110101775A TW110101775A TWI778497B TW I778497 B TWI778497 B TW I778497B TW 110101775 A TW110101775 A TW 110101775A TW 110101775 A TW110101775 A TW 110101775A TW I778497 B TWI778497 B TW I778497B
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- compound
- surface tension
- amino acid
- surfactant
- water
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 57
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000000693 micelle Substances 0.000 claims abstract description 13
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 24
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 150000001450 anions Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 9
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229940100198 alkylating agent Drugs 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 7
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
- 229940107816 ammonium iodide Drugs 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
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- 150000003951 lactams Chemical class 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 35
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- 230000002209 hydrophobic effect Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 5
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- QEKATQBVVAZOAY-UHFFFAOYSA-M sodium;4-propan-2-ylbenzenesulfonate Chemical compound [Na+].CC(C)C1=CC=C(S([O-])(=O)=O)C=C1 QEKATQBVVAZOAY-UHFFFAOYSA-M 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
- SWCSXNZBAVHUMT-UHFFFAOYSA-N 6-(dimethylamino)hexanoic acid Chemical compound CN(C)CCCCCC(O)=O SWCSXNZBAVHUMT-UHFFFAOYSA-N 0.000 description 3
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- 229920006362 Teflon® Polymers 0.000 description 2
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- XVZIAZAFOVOYAT-TTWKNDKESA-N 2-methyloxirane;(e)-octadec-9-enoic acid;oxirane Chemical compound C1CO1.CC1CO1.CCCCCCCC\C=C\CCCCCCCC(O)=O XVZIAZAFOVOYAT-TTWKNDKESA-N 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09D5/021—Aerosols
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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Abstract
本發明提供具有界面活性特性之胺基酸衍生物。該胺基酸可為天然存在的或合成的,或其可經由內醯胺,諸如己內醯胺之開環反應獲得。該胺基酸可經官能化以形成具界面活性且具有有利界面活性劑特性之化合物。本發明之化合物具有低臨界微胞濃度(CMC)以及降低液體之表面張力的優異能力。
Description
本發明係關於胺基酸衍生物及其合成方法,其中胺基酸衍生物具有界面活性特性。
界面活性劑(具有界面活性特性之分子)為一類重要的具有備受追捧特性之分子。界面活性劑可為不帶電的、兩性離子的、陽離子的或陰離子的。通常,此等化合物為具有水不溶性疏水性「尾」基及水溶性親水性「頭」基之兩親媒性分子。此等化合物可吸附在界面處,諸如兩種液體、液體與氣體或液體與固體之間的界面。在水與油之間的界面之情況下,親水性頭基延伸至水中,而疏水性尾部延伸至油中。當添加至水中時,親水性頭基延伸至水中,而疏水性尾部延伸至空氣中。界面活性劑之存在破壞水分子之間的分子間相互作用,用水分子與界面活性劑之間的較弱相互作用將其替代。此導致表面張力降低且亦可用於穩定界面。
在足夠高的濃度下,界面活性劑可形成聚集體以限制疏水性尾部暴露於極性溶劑。一種此類聚集體為微胞,其中分子排列於球體中,疏水性尾部在球體內部且親水性頭在外部以與極性溶劑相互作用。給定化合物對表面張力及其形成微胞之濃度的影響可充當界面活性劑之限定特性。
界面活性劑廣泛用於範圍介於清潔劑至護髮產品至化妝品之調配物中的商業應用中。具有界面活性特性之化合物用作肥皂、清潔劑、潤滑劑、濕潤劑、發泡劑及展布劑等。因此,存在對鑑別及合成此類化合物之持續需求。
然而,僅自其結構,可難以預測給定化合物是否將具有界面活性特性,更不必說其他重要特性,諸如界面吸附動力學、可達成之最小表面張力及/或潤濕疏水性及/或疏油性表面之能力,其亦與化合物是否將變為有用界面活性劑為一體的。舉例而言,某些胺基酸及其衍生物作為界面活性劑之建構嵌段為合乎需要的,但使用何種胺基酸之選擇遠非直觀的。由於可歸因於同一分子中存在的不同元素及部分之溶解度差異,此類化合物之合成增加另一層困難。仍需要可經由簡單途徑以商業規模容易地合成之高功效界面活性劑。
本發明提供具有界面活性特性之胺基酸衍生物。胺基酸可為天然存在或合成胺基酸,或其可經由諸如內醯胺(例如己內醯胺)之分子的開環反應獲得。胺基酸可經官能化以形成具有界面活性特性之化合物。典型地,此等化合物可具有低臨界微胞濃度(CMC)及/或降低液體之表面張力之能力。
本發明提供以下式I化合物,在本文中亦稱為界面活性劑:
式I
其中R1
、R2
及R3
係獨立地選自C1
-C6
烷基,即C1
、C2
、C3
、C4
、C5
或C6
;n為2至5之整數,即2、3、4或5;m為9至20之整數,即9、10、11、12、13、14、15、16、17、18、19或20;及X為可選自由以下組成之群的陰離子:氯離子、溴離子、碘離子及氫氧根。
結合隨附圖式參考本發明實施例之以下描述,本發明之上述及其他特徵及其實現方式將變得更清楚且將更好理解。
相關申請案之交叉參考
本申請案主張2020年1月29日申請之美國臨時申請案第62/967,173號的優先權,其揭示內容以全文引用之方式併入本文中。
如本文所使用,片語「在界定於前述值中之任兩者之間的任何範圍內」字面上意謂可選自列於此類片語之前的值中之任兩者的任何範圍,不論該等值係處於列表之下半部分內或處於列表的上半部分內。舉例而言,一對值可選自兩個較低值、兩個較高值或一較低值及一較高值。
如本文所使用,字語「烷基」意謂任何飽和碳鏈,其可為直鏈或分支鏈。
如本文所使用,片語「界面活性」意謂相關化合物能夠降低其溶解於其中的介質之表面張力,及/或與其他相之界面張力,且相應地,可吸附在液相/氣相及/或其他界面。術語「界面活性劑」可應用於此類化合物。
關於不精密之術語,可互換地使用術語「約」及「大約」,來指示包括所陳述量測值且亦包括合理地接近所陳述量測值之任何量測值的量測值。合理地接近所陳述量測值之量測值合理地少量偏離所陳述量測值,如一般熟習相關技術技術者所理解及容易確定。舉例而言,此類偏差可歸因於量測誤差或為最佳化效能而進行之輕微調整。在確定一般熟習相關技術者將不容易確定此類合理小差異之值的情況下,術語「約」及「大約」可理解為意謂所陳述值之正或負10%。
本發明提供胺基酸之衍生物。胺基酸可為天然存在的或合成的,或其可獲自內醯胺,諸如己內醯胺之開環反應。舉例而言,本發明之化合物已展示具有界面活性特性,且可界面活性劑及濕潤劑。特定言之,本發明提供下文展示之式I化合物:
式I
其中R1
、R2
及R3
係獨立地選自C1
-C6
烷基,即C1
、C2
、C3
、C4
、C5
或C6
;n為2至5之整數,即2、3、4或5;m為9至20之整數,即9、10、11、12、13、14、15、16、17、18、19或20;及X為可選自由以下組成之群的陰離子:氯離子、溴離子、碘離子及氫氧根。
此等化合物可藉由各種方法合成。一種此類方法包括打開內醯胺以得到具有N端之胺基酸且使胺基酸之N端與烷基化劑反應以得到三級胺。所得三級胺接著可與醇在酸性條件下反應以提供具有N端之胺基酸酯。胺基酸酯N端接著可與烷基化劑在鹼性條件下反應以得到四級胺。
胺基酸在N-端與C-端之間可具有少至2個或多達5個,即2、3、4或5個碳。烷基鏈可為分支鏈或直鏈的。烷基鏈可間雜有氮、氧或硫。烷基鏈可進一步經一或多個選自由以下組成之群的取代基取代:羥基、胺基、醯胺基、磺醯基、磺酸根、羧基及羧酸根。N端氮可經一或多個烷基醯基化或烷基化。舉例而言,胺基酸可為6-(二甲胺基)己酸。
胺基酸之衍生物可如下文流程2中所示合成。如所展示,在回流下將6-胺基己酸用含甲醛之甲酸處理以得到6-(二甲胺基)己酸。接著在含對甲苯磺酸(PTSA)之甲苯的存在下,將游離羧酸用醇(諸如十二醇)處理以得到對應酯,6-(二甲胺基)己酸十二烷酯。接著在碳酸鈉之存在下,將N端用碘代甲烷烷基化。
流程2
本發明之化合物展現界面活性特性。此等特性可藉由各種方法來量測及描述。可描述界面活性劑之一種方法為分子之臨界微胞濃度(CMC)。CMC可定義為微胞形成時界面活性劑之濃度,且高於該濃度時,所有額外界面活性劑併入至微胞中。
隨著界面活性劑濃度增加,表面張力降低。一旦表面完全覆蓋有界面活性劑分子,則微胞開始形成。此點表示CMC,以及最小表面張力。進一步添加界面活性劑將不進一步影響表面張力。因此CMC可藉由觀測隨界面活性劑濃度而變化之表面張力的變化來量測。一種用於量測此值之此類方法為威廉氏平板法(Wilhelmy plate method)。威廉氏板通常為藉由導線連接至天平且垂直於氣-液界面置放之薄銥鉑板。天平用於量測藉由潤濕施加於板上之力。此值接著用於根據等式1計算表面張力(γ):
等式1:γ = F/l cos θ
其中l等於潤濕周長(2w + 2d,其中w及d分別為板厚度及寬度)且cos θ (液體與板之間的接觸角)在不存在現存文獻值之情況下假設為0。
用於評定界面活性劑之效能之另一參數為動態表面張力。動態表面張力為用於特定表面或界面年齡之表面張力值。在添加界面活性劑之液體的情況下,此可不同於平衡值。在產生表面之後,表面張力立即等於純液體之表面張力。如上文所描述,界面活性劑降低表面張力;因此,表面張力下降直至達至平衡值。達至平衡所需之時間視界面活性劑之擴散速率及吸附速率而定。
量測動態表面張力之一種方法依賴於氣泡壓力張力計。此裝置量測藉助於毛細管形成於液體中之氣泡之最大內壓。所量測值對應於在某一表面年齡(即自氣泡形成開始至出現最大壓力之時間)下之表面張力。表面張力對表面年齡之相關性可藉由改變產生氣泡之速度來量測。
界面活性化合物亦可藉由如藉由接觸角所量測的其在固體基板上之潤濕能力來評定。當液滴在諸如空氣之第三種介質中與固體表面接觸時,在液體、氣體及固體之間形成三相線。在作用於三相線上且在液滴處正切之表面張力單位向量與表面之間的角描述為接觸角。接觸角(亦稱為潤濕角)為固體經液體之可濕性之量度。在完全潤濕之情況下,液體完全擴散於固體上且接觸角為0°。通常在1-100× CMC之濃度下量測給定化合物之潤濕特性,然而,其並非濃度依賴性之特性,因此可在更高或更低之濃度下量測潤濕特性之量測結果。
在一種方法中,光學接觸角測角計可用於量測接觸角。此裝置使用數位攝影機及軟體以藉由分析表面上不濡液滴(sessile droplet of liquid)之輪廓形狀來提取接觸角。
本發明之界面活性化合物之潛在應用包括適用作以下之調配物:洗髮精、護髮素、清潔劑、無斑點沖洗溶液、地板及地毯清潔劑、用於塗鴉移除之清潔劑、用於作物保護之濕潤劑、用於作物保護之佐劑及用於氣溶膠噴霧塗料之濕潤劑。
熟習此項技術者應理解,化合物之間的小差異可導致實質上不同之界面活性劑特性,使得不同化合物可在不同應用中與不同基板一起使用。
提供以下非限制性實施例以展現不同界面活性劑之不同特性。
化合物作為界面活性劑為有效的,適用於濕潤劑或發泡劑、分散劑、乳化劑及清潔劑以及其他應用。
本發明之化合物可適用於上文所描述之應用及一些其他特殊應用,諸如表面處理(諸如在個人護髮產品)中,且亦可用於產生拒水性表面。
調配物中所使用的本文所揭示之化合物的量可低至約0.001 wt%、約0.05 wt%、約0.1 wt%、約0.5 wt%、約1 wt%、約2 wt%或約5 wt%,或高達約8 wt%、約10 wt%、約15 wt%、約20 wt%或約25 wt%,或在前述值中之任兩者之間定義的任何範圍內。實例
在Bruker 500 MHz光譜儀上進行核磁共振(NMR)光譜分析。藉由威廉氏平板法在23℃下用配備有Pt-Ir板之張力計(DCAT 11,DataPhysics Instruments GmbH)測定臨界微胞濃度(CMC)。在23℃下,用氣泡壓力張力計(Krüss BP100,Krüss GmbH)測定動態表面張力。用配備有數位攝影機之光學接觸角測角計(OCA 15 Pro,DataPhysics GmbH)測定接觸角。實例 1 : 合成碘化 6-( 十二烷氧基 )-N,N,N- 三甲基 -6- 側氧基己 -1- 銨
在配備有迪安-斯塔克分水器(Dean-Stark trap)之圓底燒瓶中,將6-(二甲胺基)己酸(11.99 g,75.36 mmol)溶解於甲苯(50 mL)中。接著添加十二醇(12.68 g,75.36 mmol)及單水合對甲苯磺酸(PTSA) (14.33 g,75.36 mmol)。將反應加熱至回流持續24小時,直至在迪安-斯塔克分水器中未注意到其他水為止。在真空下移除溶劑且用己烷洗滌所得固體。將固體溶解於二氯甲烷(200 mL)中且用飽和碳酸鈉洗滌以得到51%產率之6-(二甲胺基)己酸十二烷酯。1
H NMR (DMSO) δ 4.00 (t,J
= 6.5 Hz, 2H), 2.27 (t,J
= 7.3 Hz, 2H), 2.13-2.16 (m, 2H), 2.01 (s, 6H), 1.54 - 1.53 (m, 6H), 1.27-1.18 (m, 20H), 0.86 (t, 3H)。
將6-(二甲胺基)己酸十二烷酯(1.0 g,3.05 mmol)溶解於乙腈(10 mL)中。接著添加碳酸鈉(0.388 g,3.66 mmol),且將反應物在室溫下攪拌10分鐘。添加碘代甲烷(0.57 mL,9.16 mmol),且將反應混合物加熱至40℃持續24小時,接著冷卻至室溫。將混合物過濾且濃縮以得到92%產率的呈黃色固體狀之碘化6-(十二烷氧基)-N,N,N-三甲基-6-側氧基己-1-銨。1
H NMR (DMSO) δ 4.00 (t,J
= 6.7 Hz, 2H), 3.30 – 3.22 (m, 2H), 3.04 (s, 9H), 2.34 (t,J
= 7.4 Hz, 2H), 1.70 – 1.63 (m, 2H), 1.62 – 1.46 (m, 4H), 1.31 – 1.20 (m, 20H), 0.86 (t,J
= 6.9 Hz, 3H)。實例 2 : 測定臨界微胞濃度 (CMC)
測試臨界微胞濃度(CMC)。根據在水中表面張力隨濃度之變化,測定CMC為約1 mM。可藉由此界面活性劑達至之最小表面張力之平穩值為約33 mN/m,即33 mN/m ± 3.3 mN/m。圖1為此等結果之標繪圖,展示表面張力相對於濃度。根據標繪圖,表面張力為約34 mN/m,且在1.0 mM或更大之濃度下CMC為約33.8 mN/m。實例 3 : 測定動態表面張力
用氣泡壓力張力計測定動態表面張力,該氣泡壓力張力計量測新產生之空氣-水界面之表面張力隨時間的變化。圖2呈現作為表面張力之結果與時間之標繪圖,展示在1 ms至75 ms之時間間隔內表面張力自約55.5 mN/m快速下降至約39.9 mN/m。在75 ms至50,410 ms之時間間隔內,表面張力自約39.9 mN/m緩慢下降至約34 mN/m,從而在CMC下漸近地接近表面張力之飽和值。實例 4 : 測定潤濕特性
除表面張力及表面動力學之外,亦在各種表面上測試化合物之潤濕特性。舉例而言,諸如聚乙烯-HD之疏水性基板展現具有32°之接觸角的表面潤濕。在諸如鐵氟龍(Teflon)之疏油性及疏水性基板上,所量測之接觸角比水之接觸角小得多,即67.1o
(表1)。
表1
實例 5 : 用於洗髮精之調配物
基板 | 界面活性劑之 CA (o ) | 濃度 | 水之 CA (o ) |
鐵氟龍 | 67.1 | 10× CMC | 119 |
聚乙烯-HD | 32 | 10× CMC | 93.6 |
耐綸 | 31.5 | 10× CMC | 50 |
聚對苯二甲酸伸乙酯 | 38.4 | 10× CMC | 65.3 |
在此實例中,提供一種適用作洗髮精之調配物。此調配物用於為頭髮提供光滑及絲滑的感覺。調配物之組分展示於下表2中。另外,調配物可包括呈小於1 wt%之量的其他天然油及成分,以及用於消費者訴求之維生素。
表2
實例 6 : 用於護髮素之調配物
組分 | 功能 | 重量 % |
界面活性劑 | 界面活性劑 | 0.1-10 |
月桂基硫酸銨 | 發泡劑 | 10-25 |
椰油醯胺基丙基甜菜鹼 | 輔助界面活性劑 | 0.1-5 |
椰油醯胺二乙醇胺 | 泡沫輔助劑 | 1-4 |
三仙膠或丙烯酸酯共聚物 | 增稠劑/流變改質劑 | 0-5 |
檸檬酸 | pH穩定劑 | 0.1-0.3 |
芳香劑 | 0.02-0.1 | |
水 | 49.5-89 |
在此實例中,提供一種適用作護髮素之調配物。此調配物可用於置換或還原聚四級銨-10、聚四級銨-7及二甲聚矽氧烷油,同時保持護髮素提供之易梳理性及絲般柔軟的感覺。
調配物展示於下表3中。
表3
實例 7 : 用於移除表面之難洗斑點的洗車清潔劑之調配物
組分 | 功能 | 重量 % |
界面活性劑 | 界面活性劑 | 0.1-10 |
異丙苯磺酸鈉 | 水溶助劑 | 1-3 |
月桂基硫酸銨 | 界面活性劑 | 0.1-6 |
月桂醇醚-3硫酸銨 | 界面活性劑 | 0.1-6 |
椰油醯胺二乙醇胺 | 發泡劑 | 0.5-2 |
PEG-55丙二醇油酸酯 | 乳化劑 | 0.01-1 |
芳香劑 | 0.02-0.1 | |
水 | 61.9-97.2 |
在此實例中,提供一種用於移除表面之難洗斑點的洗車用清潔劑之調配物。
調配物展示於下表4中。
表4
實例 8 : 用於無斑點沖洗或乾燥溶液之調配物
組分 | 功能 | 重量 % |
界面活性劑 | 界面活性劑 | 0.1-10 |
十二烷基苯磺酸或月桂基硫酸銨 | 發泡劑/清潔劑 | 5-14 |
單乙醇胺、二乙醇胺或三乙醇胺 | pH穩定劑 | <0.5 |
椰油醯胺二乙醇胺 | 泡沫穩定劑 | 0.1-2 |
丙二醇 | 助溶劑 | 0.05-1.6 |
芳香劑 | 0.02-0.1 | |
著色劑 | 0-0.1 | |
水 | 71.6-95.0 |
在此實例中,提供一種用於無斑點沖洗或乾燥溶液之調配物。在完成主洗滌之後,可將溶液塗覆至汽車之車窗或車身。
調配物展示於下表5中。
表5
實例 9 : 用於重型地毯清潔劑之調配物
組分 | 功能 | 重量 % |
界面活性劑 | 界面活性劑 | 0.001-2 |
水 | 98-99.999 |
在此實例中,提供一種用於重型地毯清潔劑之調配物。清潔劑為高發泡深層清潔劑。
調配物展示於下表6中。
表6
實例 10 : 用於重型表面清潔劑之調配物
組分 | 功能 | 重量 % |
界面活性劑 | 界面活性劑 | 1-15 |
十二烷基苯磺酸或月桂基硫酸銨 | 發泡劑/清潔劑 | 0.001-10 |
異丙苯磺酸鈉 | 水溶助劑 | 0.001-3 |
單乙醇胺、二乙醇胺或三乙醇胺 | pH穩定劑 | 0.01-1 |
水 | 74.95-99 |
在此實例中,提供一種用於重型表面清潔劑之調配物。此清潔劑可用於手動或自動表面清潔機器。
調配物展示於下表7中。
表7
實例 11 : 用於集中塗鴉移除清潔劑之調配物
組分 | 功能 | 重量 % |
界面活性劑 | 界面活性劑 | 0.001-25 |
十二烷基苯磺酸或月桂基硫酸銨 | 發泡劑/清潔劑 | 0.001-10 |
異丙苯磺酸鈉 | 水溶助劑 | <0.5 |
丙二醇 | 助溶劑 | 0.01-5 |
水 | 59.5-99.99 |
在此實例中,提供一種用於集中塗鴉移除清潔劑之調配物。清潔劑可用於高壓軟管中。
調配物展示於下表8中。
表8
實例 12 : 用於氣溶膠噴霧劑中之濕潤劑之調配物
組分 | 功能 | 重量 % |
界面活性劑4 | 界面活性劑 | 0.001-15 |
異丙苯磺酸鈉 | 水溶助劑 | 0.001-3 |
丙二醇 | 助溶劑 | 0.01-5 |
水 | 67-99.99 |
在此實例中,提供一種用於氣溶膠噴霧劑中之濕潤劑佐劑之調配物。氣溶膠噴霧劑可用於施加殺蟲劑或其他作物保護劑。所提供調配物旨在藉由經由極好的潤濕及低CMC提供較佳效能來降低殺蟲劑及作物保護中界面活性劑化學物質的量(通常在2-5%之間),因此提供更環保之選擇。
調配物展示於下表9中。
表9
實例 13 : 用於氣溶膠噴霧油漆之添加劑的調配物
組分 | 功能 | 重量 % |
界面活性劑 | 輔助濕潤劑 | 0.001-2 |
殺蟲劑及/或其他作物保護劑 | 0.1-10 | |
水 | 88-99.899 |
在此實例中,提供一種用於基於水之氣溶膠噴霧油漆或塗料之添加劑的調配物。調配物旨在在塗覆後提供表面上氣溶膠液滴之良好動態潤濕,因此防止油漆陷缺及其他此類問題。
調配物展示於下表10中。
表10
態樣
組分 | 功能 | 重量 % |
界面活性劑 | 濕潤劑/流平劑/防滑劑 | 0.001-5 |
氣體推進劑 | 推進劑 | 5-30 |
水包油乳液 | 色素沉著 | 0.1-25 |
Tamol 731A | 分散劑 | 1-4 |
異丙醇(97-99%純度) | 溶劑/載劑 | 7-15 |
Efka SI2022或SI 2723 | 消泡劑 | 0.001-2 |
水 | 19-86.9 |
態樣3為如態樣1或態樣2之化合物,其在水中具有約1 mM之臨界微胞濃度(CMC)。
態樣4為如態樣1至3中任一項之化合物,其在水中具有約33 mN/m之最小表面張力的平穩值。
態樣5為如態樣1至4中任一項之化合物,其在1.0 mM或更大之濃度下在水中具有等於或小於33.8 mN/m之表面張力。
態樣6為如態樣1至5中任一項之化合物,其在75 ms或更大之表面年齡下在水中具有等於或小於39.9 mN/m之表面張力。
態樣7為一種合成胺基酸界面活性劑之方法,其包含以下步驟:(1)打開內醯胺以得到具有N端之胺基酸;(2)使胺基酸之N端與烷基化劑反應以得到三級胺;(3)使三級胺與醇在酸性條件下反應以得到具有N端之胺基酸酯;及(4)使胺基酸酯之N端與烷基化劑在鹼性條件下反應以得到下式之胺基酸界面活性劑:其中X為選自由以下組成之群的陰離子:氯離子、溴離子、碘離子及氫氧根。
態樣8為如態樣7之方法,其中在步驟1中,內醯胺為己內醯胺。
態樣9為如態樣7或態樣8之方法,其中在步驟2中,烷基化劑為甲醛或多聚甲醛。
態樣10為如態樣7至9中任一項之方法,其中在步驟3中,醇為十二醇。
態樣11為如態樣7至10中任一項之方法,其中在步驟3中,酸為對甲苯磺酸。
態樣12為如態樣7至11中任一項之方法,其中在步驟4中,烷基化劑為碘代甲烷。
態樣13為如態樣7至12中任一項之方法,其中在步驟4中,該鹼為碳酸鈉。
態樣15為如態樣14之組合物,其中介質為水。
圖1展示如實例2中所描述的在pH = 7時量測的表面張力相對於濃度之標繪圖,其中Y軸描繪以毫牛頓/公尺(mN/m)為單位之表面張力(γ)及X軸描繪以毫莫耳(mM)為單位之濃度(c)。
圖2展示如實例3中所描述的作為表面張力之變化之動態表面張力與時間之標繪圖,其中Y軸描繪以毫牛頓/公尺(mN/m)為單位之表面張力及X軸描繪以毫秒(ms)為單位之表面年齡。
Claims (15)
- 如請求項1之化合物,其在水中具有約1 mM之臨界微胞濃度(CMC)。
- 如請求項1之化合物,其具有約33 mN/m之最小表面張力的平穩值。
- 如請求項1之化合物,其在1.0 mM或更大之濃度下在水中具有等於或小於33.8 mN/m之表面張力。
- 如請求項1之化合物,其在75 ms或更大之表面年齡下在水中具有等於或小於39.9 mN/m之表面張力。
- 如請求項7之方法,其中在步驟1中,該內醯胺為己內醯胺。
- 如請求項7之方法,其中在步驟2中,該烷基化劑為甲醛或多聚甲醛。
- 如請求項7之方法,其中在步驟3中,該醇為十二醇。
- 如請求項7之方法,其中在步驟3中,該酸為對甲苯磺酸。
- 如請求項7之方法,其中在步驟4中,該烷基化劑為碘代甲烷。
- 如請求項7之方法,其中在步驟4中,該鹼為碳酸鈉。
- 如請求項14之組合物,其中該介質為水。
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5798095A (en) * | 1995-07-15 | 1998-08-25 | Wella Aktiengesellschaft | Hair treatment composition and method of making same |
US5972323A (en) * | 1996-08-06 | 1999-10-26 | Wella Ag | Hydrolytically cleavable active ingredient derivative compounds, hair treatment compositions containing them and hair treatment methods |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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GB2310659A (en) * | 1996-02-27 | 1997-09-03 | Procter & Gamble | Cationic detergent compounds |
WO2000032559A1 (en) * | 1998-12-03 | 2000-06-08 | The Dow Chemical Company | Cationic ester surfactants which are suitable for both liquid and powder formulations |
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US7073588B2 (en) * | 2004-02-27 | 2006-07-11 | Halliburton Energy Services, Inc. | Esterquat acidic subterranean treatment fluids and methods of using esterquats acidic subterranean treatment fluids |
US9217929B2 (en) * | 2004-07-22 | 2015-12-22 | Air Products And Chemicals, Inc. | Composition for removing photoresist and/or etching residue from a substrate and use thereof |
US7863485B2 (en) * | 2004-12-10 | 2011-01-04 | Omnitech Environmental, Llc | Additive and vehicle for inks, paints, coatings and adhesives |
KR102059398B1 (ko) * | 2012-06-15 | 2019-12-26 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 계면활성제 시스템을 위한 알킬 글리코사이드-기반 마이셀 증점제 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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