JP6655025B2 - 増粘安定剤、及びそれを用いた増粘安定化組成物 - Google Patents
増粘安定剤、及びそれを用いた増粘安定化組成物 Download PDFInfo
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- JP6655025B2 JP6655025B2 JP2016560163A JP2016560163A JP6655025B2 JP 6655025 B2 JP6655025 B2 JP 6655025B2 JP 2016560163 A JP2016560163 A JP 2016560163A JP 2016560163 A JP2016560163 A JP 2016560163A JP 6655025 B2 JP6655025 B2 JP 6655025B2
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- thickening
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- stabilizer
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- 230000009969 flowable effect Effects 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 230000000087 stabilizing effect Effects 0.000 claims description 15
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940093609 tricaprylin Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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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
- C09D7/43—Thickening agents
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
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Description
本発明の他の目的は、前記化合物を含有する増粘安定剤、前記増粘安定剤により増粘又は安定化された増粘安定化組成物、及びその製造方法を提供することにある。
(R2−HNOC)4-n−R1−(CONH−R3)n (1)
(式中、R1はブタンの構造式から4個の水素原子を除いた基であり、R2、R3は互いに異なって、炭素数4以上の脂肪族炭化水素基である。nは1〜3の整数である)
で表される化合物を提供する。
[1] 下記式(1)
(R2−HNOC)4-n−R1−(CONH−R3)n (1)
(式中、R1はブタンの構造式から4個の水素原子を除いた基であり、R2、R3は互いに異なって、炭素数4以上の脂肪族炭化水素基である。nは1〜3の整数である)
で表される化合物。
[2] 式(1)中のR2、R3が炭素数4〜20の分岐鎖状アルキル基と、炭素数4〜20の直鎖状アルキル基又は直鎖状アルケニル基の組み合わせである[1]に記載の化合物。
[3] 式(1)で表される化合物が、式(1-1)〜(1-5)で表される化合物から選択される少なくとも1種の化合物である[1]又は[2]に記載の化合物。
[4] 式(1)で表される化合物が、式(1-1)で表される化合物及び/又は式(1-2)で表される化合物である[1]又は[2]に記載の化合物。
[5] [1]〜[4]の何れか1つに記載の化合物を含む増粘安定剤。
[6] 式(1)で表される化合物を、増粘安定剤全量の60重量%以上含有する[5]に記載の増粘安定剤。
[7] [5]又は[6]に記載の増粘安定剤と流動性有機物質を含む増粘安定化組成物。
[8] 流動性有機物質が、炭化水素油、エーテル、ハロゲン化炭化水素、石油成分、動植物油、シリコーン油、エステル、芳香族カルボン酸、及びピリジンから選択される少なくとも1種の化合物である[7]に記載の増粘安定化組成物。
[9] 増粘安定剤を流動性有機物質1000重量部に対して0.1〜100重量部含有する[7]又は[8]に記載の増粘安定化組成物。
[10] 粘度[25℃、せん断速度10(1/s)における]が0.1〜20Pa・sである[7]〜[9]の何れか1つに記載の増粘安定化組成物。
[11] [5]又は[6]に記載の増粘安定剤と流動性有機物質を相溶させる工程を経て、[7]〜[10]の何れか1つに記載の増粘安定化組成物を得る増粘安定化組成物の製造方法。
本発明の化合物は下記式(1)で表される。
(R2−HNOC)4-n−R1−(CONH−R3)n (1)
1. ブタンテトラカルボン酸を塩化チオニルと反応させてブタンテトラカルボン酸テトラクロライドを得、得られたブタンテトラカルボン酸テトラクロライドにアミン(R2−NH2とR3−NH2;R2、R3は前記に同じ)を反応させる方法
2. ブタンテトラカルボン酸二無水物にアミン(1)(R2−NH2;R2は前記に同じ)を反応させてアミック酸を得、更にアミン(2)(R3−NH2;R3は前記に同じ)を縮合剤を用いて縮合させる方法
R−N=C=N−R’
上記式中、R、R’としては、例えば、ヘテロ原子含有置換基を有していてもよい、炭素数3〜8の直鎖状若しくは分岐鎖状のアルキル基、又は3〜8員のシクロアルキル基である。R、R’は同一であってもよく、異なっていてもよい。また、RとR’は互いに結合して−N=C=N−基と共に環を形成していてもよい。
本発明の増粘安定剤は、上記式(1)で表される化合物を1種単独で、又は2種以上を組み合わせて含むことを特徴とする。
本発明の増粘安定化組成物は、上記増粘安定剤と流動性有機物質を含み、前記増粘安定剤により流動性有機物質が増粘された組成物、又は前記増粘安定剤により流動性有機物質が増粘されることによって組成が均一に安定化された組成物である。
ジムロート冷却管、窒素導入口、滴下ロート、及び熱電対を備えた100mL4つ口セパラブルフラスコにピリジン20mL、1,2,3,4−ブタンテトラカルボン酸−1,2:3,4−二無水物4.2g(0.021mol)、オレイルアミン11.3g(0.042mol)を仕込んだ。系内温度を50℃に設定し、3時間熟成した。
その後、2−エチルヘキシルアミン5.4g(0.042mol)、ジイソプロピルカルボジイミド5.8g(0.048mol)を仕込み、更に8時間熟成を行った。
その後、得られた粗液の低沸分をエバポレータにて除去し、メタノールで洗浄し、淡黄色の湿粉を得た。更に得られた湿粉についてCHCl3/CH3OH(70/30(v/v))で再結晶を行い、1,2,3,4−ブタンテトラカルボン酸ジ(2−エチルヘキシルアミド)ジ(オレイルアミド)[1,2,3,4−ブタンテトラカルボン酸−1,4−ジ(2−エチルヘキシルアミド)−2,3−ジ(オレイルアミド)と1,2,3,4−ブタンテトラカルボン酸−1,3−ジ(2−エチルヘキシルアミド)−2,4−ジ(オレイルアミド)の混合物]を16.7g得た(収率:83%)。反応生成物の構造は1H−NMRにより確認した。
1H-NMR (270MHz, CDCl3):δ 0.81-0.88(m, 18H), 1.0-1.4(m, 70H), 1.40-1.45(m, 8H), 1.81-1.99(m, 8H), 2.90-3.45(m, 6H), 5.32-5.40(m, 4H), 6.32(m,4H)
2−エチルヘキシルアミン5.4g(0.042mol)に代えて、オレイルアミン11.3g(0.042mol)を使用した以外は実施例1と同様にして、1,2,3,4−ブタンテトラカルボン酸テトラオレイルアミドを20.9g得た(収率:81%)。反応生成物の構造は1H−NMRにより確認した。
1H-NMR (270MHz, CDCl3):δ 0.81-0.88(m, 12H), 1.0-1.4(m, 104H), 1.40-1.45(m, 8H), 1.81-1.99(m, 8H), 2.90-3.45(m, 6H), 5.32-5.40(m, 8H), 6.32(m,4H)
表に示す各種流動性有機物質[流動パラフィン(粘度:0.14Pa・s)、イソドデカン(粘度:0.001Pa・s)、オクタン酸セチル(粘度:0.012Pa・s);何れも沸点は100℃以上]を試験管に1cm3ずつはかりとり、これに実施例1で得られた増粘安定剤(1)をそれぞれ10mg加えて混合し、100℃で加熱撹拌して流動性有機物質と増粘安定剤(1)を相溶させ、25℃まで冷却して増粘安定化組成物を得た。
得られた増粘安定化組成物の粘度は、以下の通りであった。
流動パラフィンの増粘安定化組成物:2.31Pa・s
イソドデカンの増粘安定化組成物:0.86Pa・s
オクタン酸セチルの増粘安定化組成物:2.67Pa・s
増粘倍率=増粘安定化組成物の粘度/増粘安定化する前の流動性有機物質の粘度
<評価基準>
1: 1.0倍を超え、2.0倍以下
2: 2.0倍を超え、4.8倍以下
3: 4.8倍を超え、10倍以下
4: 10倍を超え、50倍以下
5: 50倍を超え、100倍以下
6: 100倍を超え、10000倍以下
7: 10000倍超
増粘安定剤(1)に代えて、比較例1で得られた増粘安定剤(2)を使用した以外は実施例2と同様に行った。
Claims (5)
- 下記式(1)
(R2−HNOC)4-n−R1−(CONH−R3)n (1)
(式中、R1はブタンの構造式から4個の水素原子を除いた基であり、R 2 、R 3 は、何れか一方が炭素数4〜20の分岐鎖状アルキル基であり、他の一方が炭素数4〜20の直鎖状アルキル基又は直鎖状アルケニル基である。nは1〜3の整数である)
で表される化合物。 - 請求項1又は2に記載の化合物を含む増粘安定剤。
- 請求項3に記載の増粘安定剤と流動性有機物質を含む増粘安定化組成物。
- 請求項3に記載の増粘安定剤と流動性有機物質を相溶させる工程を経て、請求項4に記載の増粘安定化組成物を得る増粘安定化組成物の製造方法。
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US5973076A (en) * | 1995-05-31 | 1999-10-26 | New Japan Chemical Co., Ltd. | Polybutene-1 resin composition and a method of accelerating the crystal transformation thereof |
JP5401644B2 (ja) * | 2007-12-28 | 2014-01-29 | 新日本理化株式会社 | 新規な有機ゲル化剤 |
JP2010111761A (ja) * | 2008-11-06 | 2010-05-20 | New Japan Chem Co Ltd | ポリエチレン樹脂組成物及びその成形体 |
EP2813558B1 (en) * | 2012-02-08 | 2018-01-17 | Ajinomoto Co., Inc. | Gelling agent |
JP6246138B2 (ja) | 2013-02-08 | 2017-12-13 | 株式会社ダイセル | 増粘安定剤、及びそれを用いた増粘安定化組成物 |
JP6064740B2 (ja) * | 2013-03-28 | 2017-01-25 | 大日本印刷株式会社 | 加飾シート及び加飾樹脂成形品 |
KR102181705B1 (ko) | 2013-05-20 | 2020-11-23 | 아지노모토 가부시키가이샤 | 겔화제 |
WO2015174343A1 (ja) * | 2014-05-14 | 2015-11-19 | 株式会社ダイセル | ヘアオイル |
KR102454319B1 (ko) * | 2014-06-09 | 2022-10-14 | 주식회사 다이셀 | 클렌징 화장료 |
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