JP2019530566A - 香料を封入する方法におけるコロイド安定剤としての両性電解質コポリマーの使用 - Google Patents
香料を封入する方法におけるコロイド安定剤としての両性電解質コポリマーの使用 Download PDFInfo
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- JP2019530566A JP2019530566A JP2019514798A JP2019514798A JP2019530566A JP 2019530566 A JP2019530566 A JP 2019530566A JP 2019514798 A JP2019514798 A JP 2019514798A JP 2019514798 A JP2019514798 A JP 2019514798A JP 2019530566 A JP2019530566 A JP 2019530566A
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- ampholyte copolymer
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 1
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- 229920003226 polyurethane urea Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 238000012673 precipitation polymerization Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 229940113147 shellac Drugs 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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Classifications
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/87—Polyurethanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
-
- A—HUMAN NECESSITIES
- 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
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
-
- A—HUMAN NECESSITIES
- 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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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Fats And Perfumes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
- エマルション(その中でマイクロカプセルが形成される)の安定性、
- マイクロカプセルのシェルの厚さの制御、
- マイクロ粒子の凝集塊の形成防止、
- マイクロカプセルを含有する水性組成物即ちスラリーの安定性
を向上させる。
両性電解質コポリマーは
- 2から99モル%の、少なくとも1つの第四級アンモニウム基、好ましくは1つの第四級アンモニウム基を有するカチオン性モノマー、
- 1から98モル%のアクリル系モノマー、
- 0から97モル%の非イオン性モノマー
を含み、両性電解質コポリマーは、アニオン電荷よりもカチオン電荷を多く有する、使用に関する。
両性電解質コポリマーは
- 2から99モル%の、少なくとも1つの第四級アンモニウム基、好ましくは1つの第四級アンモニウム基を有するカチオン性モノマー、
- 1から98モル%のアクリル系モノマー、
- 0から97モル%の非イオン性モノマー
を含み、両性電解質コポリマーは、アニオン電荷よりもカチオン電荷を多く有する、使用に関する。
- 両性電解質コポリマー、少なくとも1種のアニオン修飾ポリイソシアナート及び少なくとも1種の香料成分を含む水性相を調製する工程、
- 得られた組成物をコアセルベート又は乳化させる工程、
- 少なくとも1種の多官能アミン又は少なくとも1種の多官能アルコールを添加して、重付加反応を開始する工程、
- 混合物を加熱することにより、マイクロカプセル分散液を形成する工程
によって、香料を含有するコアシェルマイクロカプセルを調製する方法において、両性電解質コポリマーをコロイド安定剤として使用してもよい。
- 両性電解質コポリマー、少なくとも1種のアニオン修飾ポリイソシアナート、少なくとも1種の非イオン性ポリイソシアナート及び少なくとも1種の香料成分を含む水性相を調製する工程、
- 得られた組成物をコアセルベート又は乳化させる工程、
- 少なくとも1種の多官能アミン又は少なくとも1種の多官能アルコールを添加して、重付加反応を開始する工程、
- 混合物を加熱することにより、マイクロカプセル分散液を形成する工程
によって、香料を含有するコアシェルマイクロカプセルを調製する方法において、両性電解質コポリマーをコロイド安定剤として使用してもよい。
- 30から95モル%、好ましくは60から90モル%のメタクリルアミドプロピルトリメチルアンモニウムクロリド(MAPTAC)、
- 5から70モル%、好ましく10から40モル%のアクリル酸又はその水溶性塩、
- 0から80モル%、好ましくは0から50モル%のアクリルアミド
を含む。
- 少なくとも1種の非イオン性ポリイソシアナート(A)及び少なくとも1種のアニオン修飾ポリイソシアナート(B)を含む、少なくとも2種の異なるポリイソシアナート
- 及び少なくとも1種の多官能アミン
の混合物の反応生成物で作製されている。
本発明のポリマーは、以下の手順を用いて得られる。本例は、アクリル酸/MAPTACコポリマーで実施する。本ポリマーを製造するために、以下の化合物を反応器に導入する。
MAPTAC(50%水溶液) 464g
アクリル酸(90%水溶液) 34.4g
水 119g
EDTA 0.03g
次亜リン酸ナトリウム 0.14g
反応媒体のpHを、NaOHを用いて5.0〜5.2に調整する。
2,2'-アゾビス(2-アミジノプロパン)二塩酸塩(10%水溶液)53gも、反応器に導入する。
100gのポリマー[AP]と450gの水との水溶液を調製し、緩衝塩でpHを9に調整した。封入すべき香水300gと、Desmodur(登録商標)W1(ジシクロヘキシルメタンジイソシアナート)20gとBayhydur(登録商標)XP2547(ヘキサメチレンジイソシアナートのアニオン修飾イソシアヌレート)8gとを含む混合物を調製した。この水溶液と混合物とを合わせ、室温で撹拌装置により乳化させた。この乳化プロセスを、所望の液滴径になるまで実施した。次にLupasol(登録商標)G100溶液(直鎖状ポリエチレンイミン)10gを1度に添加した。反応混合物を4時間かけて80℃まで徐々に加熱した。界面重合後、アンモニア溶液12g及びNatrosol 250HX 0.4gを添加した。次いで混合物を室温まで冷却した。
水450gを用意し、緩衝塩を用いてpHを9に調整した。封入すべき香水300gと、Desmodur(登録商標)W1 20gとBayhydur(登録商標)XP2547 8gとを含む混合物を調製した。水溶液と混合物とを合わせ、室温で撹拌装置により撹拌した。撹拌を、所望の液滴径になるまで実施した。次にLupasol(登録商標)G100溶液10gを1度に添加した。反応混合物を60℃まで徐々に加熱し、[AP]100gの水溶液を添加した。次に、反応混合物を80℃まで2時間更に加熱した。その後、アンモニア溶液12g及びNatrosol 250HX 0.4gを添加した。次いで混合物を室温まで冷却した。
Claims (15)
- 香料を含有するコアシェルマイクロカプセルの調製における、コロイド安定剤としての両性電解質コポリマーの使用であって、前記マイクロカプセルは、少なくとも1種のアニオン修飾ポリイソシアナートと少なくとも1種のポリアミン又は少なくとも1種の多官能アルコールとの反応生成物で作製されており、
前記両性電解質コポリマーは、
- 2から99モル%の、少なくとも1つの第四級アンモニウム基を有するカチオン性モノマー、
- 1から98モル%のアクリル系モノマー、
- 0から97モル%の非イオン性モノマー
を含み、前記両性電解質コポリマーは、アニオン電荷よりもカチオン電荷を多く有し、
前記両性電解質コポリマーのカチオン電荷は、前記カチオン性モノマーの前記少なくとも1つの第四級アンモニウム基のみによるものである、使用。 - マイクロカプセルが、少なくとも1種のアニオン修飾ポリイソシアナート及び少なくとも1種の非イオン性ポリイソシアナートと、少なくとも1種のポリアミン又は少なくとも1種の多官能アルコールとの反応生成物で作製されていることを特徴とする、請求項1に記載の両性電解質コポリマーの使用。
- 前記カチオン性モノマーが、四級化ジメチルアミノエチルアクリレート(ADAME)、四級化ジメチルアミノエチルメタクリレート(MADAME)、ジメチルジアリルアンモニウムクロリド(DADMAC)、アクリルアミドプロピルトリメチルアンモニウムクロリド(APTAC)及びメタクリルアミドプロピルトリメチルアンモニウムクロリド(MAPTAC)からなる群から選択されることを特徴とする、請求項1又は2に記載の両性電解質コポリマーの使用。
- 前記カチオン性モノマーがメタクリルアミドプロピルトリメチルアンモニウムクロリド(MAPTAC)であることを特徴とする、請求項1から3のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記アクリル系モノマーが、アクリル酸、メタクリル酸、イタコン酸、クロトン酸、マレイン酸、フマル酸、2-アクリルアミド-2-メチルプロパンスルホン酸、ビニルスルホン酸、ビニルホスホン酸、アリルスルホン酸、アリルホスホン酸、スチレンスルホン酸、及びそれらのアルカリ金属、アルカリ土類金属又はアンモニウムの水溶性塩からなる群から選択されることを特徴とする、請求項1から4のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記アクリル系モノマーが(メタ)アクリル酸又はその水溶性塩であることを特徴とする、請求項1から5のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記非イオン性モノマーが、アクリルアミド、メタクリルアミド、N-イソプロピルアクリルアミド、N,N-ジメチルアクリルアミド、N-メチロールアクリルアミド、N-ビニルホルムアミド、N-ビニルアセトアミド、N-ビニルピリジン及びN-ビニルピロリドンからなる群から選択されることを特徴とする、請求項1から6のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記非イオン性モノマーがアクリルアミドであることを特徴とする、請求項1から7のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記両性電解質コポリマーが30から95モル%のカチオン性モノマーを含むことを特徴とする、請求項1から8のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記両性電解質コポリマーが60から90モル%のカチオン性モノマーを含むことを特徴とする、請求項1から9のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記両性電解質コポリマーが5から70モル%のアクリル系モノマーを含むことを特徴とする、請求項1から10のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記両性電解質コポリマーが10から40モル%のアクリル系モノマーを含むことを特徴とする、請求項1から11のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記両性電解質コポリマーが、
- 30から95モル%、好ましくは60から90モル%のメタクリルアミドプロピルトリメチルアンモニウムクロリド(MAPTAC)、
- 5から70モル%、好ましく10から40モル%のアクリル酸又はその水溶性塩、
- 0から80モル%、好ましくは0から50モル%のアクリルアミド
を含むことを特徴とする、請求項1から9のいずれか一項に記載の両性電解質コポリマーの使用。 - 前記両性電解質コポリマーが少なくとも100,000g/molの分子量を有することを特徴とする、請求項1から13のいずれか一項に記載の両性電解質コポリマーの使用。
- 前記両性電解質コポリマーが少なくとも500,000g/molの分子量を有することを特徴とする、請求項1から14のいずれか一項に記載の両性電解質コポリマーの使用。
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EP16306196.3 | 2016-09-19 | ||
EP16306196.3A EP3295929A1 (en) | 2016-09-19 | 2016-09-19 | Use of an ampholyte copolymer as colloidal stabilizer in a process of encapsulating fragrance |
PCT/EP2017/073518 WO2018050899A2 (en) | 2016-09-19 | 2017-09-18 | Use of an ampholyte copolymer as colloidal stabilizer in a process of encapsulating fragrance |
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EP (2) | EP3295929A1 (ja) |
JP (1) | JP6980007B2 (ja) |
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BR (1) | BR112019004886B1 (ja) |
ES (1) | ES2846248T3 (ja) |
MX (1) | MX2019002958A (ja) |
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EP3784713B1 (en) * | 2018-04-24 | 2024-02-21 | Symrise AG | Core-shell capsules prepared with linear and cyclic aliphatic polyisocyanates |
CN112725098B (zh) * | 2020-12-28 | 2022-04-08 | 厦门琥珀日化科技股份有限公司 | 一种微胶囊香精洗衣液及其制备方法 |
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BR112019004886A2 (pt) | 2019-06-11 |
EP3295929A1 (en) | 2018-03-21 |
CN109789084A (zh) | 2019-05-21 |
SG11201901917RA (en) | 2019-04-29 |
US20190255501A1 (en) | 2019-08-22 |
CN109789084B (zh) | 2022-03-08 |
ES2846248T3 (es) | 2021-07-28 |
PL3515403T3 (pl) | 2021-06-14 |
WO2018050899A3 (en) | 2019-04-25 |
JP6980007B2 (ja) | 2021-12-15 |
MX2019002958A (es) | 2019-07-04 |
US10758885B2 (en) | 2020-09-01 |
WO2018050899A2 (en) | 2018-03-22 |
EP3515403B1 (en) | 2021-01-13 |
BR112019004886B1 (pt) | 2022-07-12 |
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