JP2020531666A - 新規アニオン性界面活性剤、ならびにそれを含有する洗剤および洗浄剤 - Google Patents
新規アニオン性界面活性剤、ならびにそれを含有する洗剤および洗浄剤 Download PDFInfo
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- JP2020531666A JP2020531666A JP2020512041A JP2020512041A JP2020531666A JP 2020531666 A JP2020531666 A JP 2020531666A JP 2020512041 A JP2020512041 A JP 2020512041A JP 2020512041 A JP2020512041 A JP 2020512041A JP 2020531666 A JP2020531666 A JP 2020531666A
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- 239000011975 tartaric acid Substances 0.000 description 1
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- UDBAOKKMUMKEGZ-UHFFFAOYSA-K trichloromanganese Chemical compound [Cl-].[Cl-].[Cl-].[Mn+3] UDBAOKKMUMKEGZ-UHFFFAOYSA-K 0.000 description 1
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristoyl-sn-glycerol Natural products CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/26—Sulfonic acids or sulfuric acid esters; Salts thereof derived from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
- C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
- C11D17/042—Water soluble or water disintegrable containers or substrates containing cleaning compositions or additives for cleaning compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/12—Soft surfaces, e.g. textile
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
Description
の化合物を、硫酸化剤、例えばクロロスルホン酸または三酸化硫黄ピリジンを使用して硫酸化すること、および場合により、その後にX+OH−、X+HCO− 3、またはX+ 2CO2− 3(式中、X+は上記で特定された意味を有する)と反応させて中和することにより調製できる。一般式(III)および(IV)の化合物、特にその混合物は、2−ヒドロキシメチル−テトラヒドロフラン−3,4−ジオールのアセタール化により、特にアルデヒドとそれらとの酸触媒反応により得ることができる。一般式(III)の化合物は、有機化学の従来の方法によって一般式(IV)の化合物から分離できる。同じことが一般式(I)および(II)の化合物にも、それらの混合物が一般式(III)および(IV)の化合物の混合物から生成された場合に当てはまる。2−ヒドロキシメチル−テトラヒドロフラン−3,4−ジオールは、ペンチトールの酸誘導環化により調製できる。リビトール、D−またはL−アラビトール、またはキシリトールが出発点であるかどうか、およびペンチトールのどの末端C原子がテトラヒドロフラン環部分を形成するかに応じて、アルデヒドとの反応により、その元のカルボニルC原子に別のキラル中心が生じ、三置換テトラヒドロフラン環の3つのキラル中心に、異なる配置が生じ得る。したがって、一般式(I)、(II)、(III)および(IV)の化合物は、その生成に応じて、通常、立体異性体混合物として存在する。ペンチトールは、ペントースを還元することにより得ることができ、それらは、ヘミセルロース、特に生成されるリビトールの還元的切断によっても得られる。ペントースおよびヘミセルロースは、種々の植物から得られる。
A:2−(ヒドロキシメチル)テトラヒドロフラン−3,4−ジオールの調製
50.0g(0.329mol)のリビトールを70mlの3モルのH2SO4と混合した。反応混合物を24時間加熱還流した。次いで、それを氷水で冷却し、14gの水酸化ナトリウム(0.35mol)を添加することにより前記硫酸を中和した。暗褐色のシロップが形成されるまで、反応混合物を真空下で濃縮した。これを150mlのエタノールと混合し、そして、混合物を60℃に加熱し、プリーツフィルターを通して濾過した。ろ液を50体積%に濃縮し、−18℃に冷却した。 沈殿物を濾別し、高真空下で乾燥させた。40.9gの2−(ヒドロキシメチル)テトラヒドロフラン−3,4−ジオールが得られた。収率:93%
1H-NMR[D2O]:δ=3.54(dd,J=12.3,5.1Hz,1H);3.73(m,3H);3.98(m,2H);4.17(m,1H)ppm
13C−NMR[D2O]:δ=61.23;70.97;71.50;72.14;81.44ppm
40mlのエタノールに溶解した10.00gの2−(ヒドロキシメチル)テトラヒドロフラン−3,4−ジオール(74.6mmol)を、11mlのn−ドデカナール(49.7mmol)および0.2重量%のカンフル−10−スルホン酸と混合し、80°Cで24時間攪拌した。反応混合物を室温に冷却した後、25mlのジエチルエーテルおよび25mlの希釈NaCl水溶液で2回抽出した。複合有機層を10mlの飽和NaHCO3水溶液および希釈NaCl水溶液で洗浄し、NaSO4で乾燥させた。ジエチルエーテルをロータリーエバポレーターで除去し、残渣を高真空下50℃で乾燥させた。2−(ヒドロキシメチル)テトラヒドロフラン−3,4−ジオールと2−ウンデシルテトラヒドロ−4H−フロ[3,2−d][1,3]ジオキシン−7−オールとの比率が46:54である混合物13.65gが得られた。収率:61%
13C−NMR[CDCl3]:δ=14.11;22.68;23.92;23.98;29.33;29.50;29.53;29.58;29.61;29.63;31.90;33.40;33.45;61.74;62.01;62.21;72.46;72.72;80.00;80.05;80.97;81.56;82.11;83.92;84.58;104.59;107.60ppm
300mlアセトニトリルに溶解した工程Bで得られた2−(ヒドロキシメチル)テトラヒドロフラン−3,4−ジオールおよび2−ウンデシルテトラヒドロ−4H−フロ[3,2−d][1,3]ジオキシン7−オールの混合物13.65g(45.43mmol)を8.68gの三酸化硫黄ピリジン錯体(54.51mmol、1.2当量)と混合し、反応混合物を75℃で16時間撹拌した。次に、0.5mlの脱イオン水を加え、混合物を75℃でさらに15分間攪拌した。薄茶色のシロップが残るまで、溶媒をロータリーエバポレーターで除去した。このシロップを200mlのエタノールに吸収させ、7.25gのNa2CO3(68.13mmol、1.5当量)と混合し、40℃で4日間撹拌した。次いで、混合物をシリカゲル150により濾過し、エタノール200mlおよびメタノール200mlで2回洗浄した。濾液をロータリーエバポレーターで濃縮し、残った白色/ベージュ色の固体を高真空下で乾燥させ、アセトンで2回洗浄し、遠心分離(7,000rpm、10分間)で除去した。高真空下で乾燥した後、重量比46:54で7.2gのP1およびP2が得られた。収率:60%
13C−NMR[D2O]:δ=13.83;13.86;22.71;24.19;24.43;29.70;29.94;30.05;30.12;30.15;30.24;32.12;33.28;33.55;67.48;67.67;72.68;73.15;80.07;80.98;81.41;82.07;82.11;82.18;104.68;106.72ppm
Claims (9)
- 一般式(I)または一般式(II):
またはそれらの混合物のアニオン性界面活性剤。 - 一般式(I)または一般式(II):
またはそれらの混合物のアニオン性界面活性剤の製造方法であり、
a)リビトール、アラビトール、キシリトールまたはそれらの混合物から、酸誘導により水を分離すること、
b)このようにして得られた2−ヒドロキシメチル−テトラヒドロフラン−3,4−ジオールをアルデヒドRCHO[式中、Rは上記の意味を有する]と反応させること、および
c)次いで、硫酸化剤を使用して硫酸化すること、および場合により、次いで、X+OH−、X+HCO− 3、またはX+ 2CO2− 3[式中、X+はアルカリ金属カチオンまたはグループN+R1R2R3であり、R1、R2、およびR3は、互いに独立して、水素、1〜6個のC原子を有するアルキル基、または2〜6個のC原子を有するヒドロキシアルキル基である]と反応させて中和すること
による、方法。 - 一般式(I)または一般式(II):
またはそれらの混合物のアニオン性界面活性剤を含有する洗剤または洗浄剤。 - 1重量%〜99重量%、特に3重量%〜65重量%の一般式(I)または一般式(II)、またはそれらの混合物のアニオン性界面活性剤を含有することを特徴とする、請求項3に記載の洗剤または洗浄剤。
- 最大で99重量%、特に3重量%〜65重量%の追加の界面活性剤をさらに含有することを特徴とする、請求項3または4に記載の洗剤または洗浄剤。
- 微粒子であり、ビルダーを、特に1重量%〜60重量%の範囲の量で含有することを特徴とする、または、液体であり、1重量%〜90重量%、特に10重量%〜85重量%の水、水混和性溶媒、または水と水混和性溶媒との混合物を含むことを特徴とする、請求項3〜5のいずれか一項に記載の洗剤または洗浄剤。
- 個別に投与可能なように、水溶性材料で作られたチャンバー内に分割され、15重量%未満の、特に1重量%〜12重量%の範囲の水を含有することを特徴とする、請求項3〜5のいずれか一項に記載の洗剤または洗浄剤。
- 一般式(I)または一般式(II):
またはそれらの混合物のアニオン性界面活性剤の、洗濯物を洗濯する、または硬質表面を洗浄するときの洗剤または洗浄剤の性能を向上させるための使用。 - 一般式(I)および一般式(II)、またはそれらの混合物の化合物において、Rは7〜21個のC原子を有する直鎖状または分枝状の、特に直鎖状のアルキル基である、請求項1に記載の界面活性剤、請求項2に記載の製造方法、請求項3〜7のいずれか一項に記載の洗剤または洗浄剤、または請求項8に記載の使用。
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