JPH0257428B2 - - Google Patents
Info
- Publication number
- JPH0257428B2 JPH0257428B2 JP60252894A JP25289485A JPH0257428B2 JP H0257428 B2 JPH0257428 B2 JP H0257428B2 JP 60252894 A JP60252894 A JP 60252894A JP 25289485 A JP25289485 A JP 25289485A JP H0257428 B2 JPH0257428 B2 JP H0257428B2
- Authority
- JP
- Japan
- Prior art keywords
- weight ratio
- polyvinyl pyrrolidone
- weight
- added
- fragrance
- 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.)
- Expired - Lifetime
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000003205 fragrance Substances 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 20
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 20
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 17
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 15
- 229920000858 Cyclodextrin Polymers 0.000 claims description 15
- 230000005923 long-lasting effect Effects 0.000 claims description 15
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 15
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 8
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 8
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000001568 sexual effect Effects 0.000 claims description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims 2
- 150000005846 sugar alcohols Chemical class 0.000 claims 1
- 239000002304 perfume Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 244000178870 Lavandula angustifolia Species 0.000 description 4
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 4
- 239000001102 lavandula vera Substances 0.000 description 4
- 235000018219 lavender Nutrition 0.000 description 4
- 230000002085 persistent effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010635 coffee oil Substances 0.000 description 1
- 239000010639 cypress oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】
<産業上の利用分野>
この発明は、香りが芳香豊かに永続きし、しか
もフイルムや紙等に塗り易い持続性香料の製造方
法に関するものである。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a method for producing a long-lasting fragrance that has a rich and persistent fragrance and is easy to apply to films, paper, and the like.
<従来の技術>
アルコールに香油を溶解した香料は広く使用さ
れているが香りに持続性がない。また、固形物に
した香料もあるが、これは固形物であるために香
りの発散量が液体のものに比し劣る。そこで、本
発明者は先に、アルコールにヒドロキシプロピル
セルロースを少量溶解させたものと香料にD−ベ
ンジリデンソルビトールを混合させたものとを混
合して香りが長期間持続するようにした香料の製
造方法を開発して特許出願(特願昭57−149075号
(特公昭61−60046号公報))した。<Prior art> Perfume prepared by dissolving perfume oil in alcohol is widely used, but the fragrance does not last long. There are also solid fragrances, but because they are solids, the amount of scent released is inferior to that of liquids. Therefore, the present inventor first developed a method for producing a fragrance that has a long-lasting fragrance by mixing a small amount of hydroxypropylcellulose dissolved in alcohol and a fragrance mixed with D-benzylidene sorbitol. We developed this and filed a patent application (Japanese Patent Application No. 149075/1983 (Japanese Patent Publication No. 60046/1983)).
<発明が解決しようとする問題点>
上記特許出願したものは、香りを永続きさせる
という目的は達し、スプレーに使用するのは有効
であつた。しかし、フイルムや紙等の表面に塗る
には塗りにくく向いていないという欠点があつ
た。<Problems to be Solved by the Invention> The above-mentioned patent application achieved the purpose of making the fragrance last longer and was effective when used as a spray. However, it has the disadvantage that it is difficult to apply and is not suitable for coating on surfaces such as film and paper.
<問題点を解決するための手段>
そこで、この発明にかかる持続性香料の製造方
法はポリビニールピロリドンの1%〜60%(重量
比)のエタノール又はメタノール溶解液に香料類
を1%〜60%(重量比)加えて撹拌混合してポリ
ビニールピロリドンにより香りの揮散を抑制させ
て保香性を高めるとともに、さらにこれにヒドロ
キシプロピルセルロースを1%〜30%(重量比)
加えたりベンジルアルコール又はデイエチルフタ
レイトを1%〜10%(重量比)添加してさらに香
りの持続性を高めたり、香料類をサイクロデキス
トリン若しくはサイクロデキストリンを含有した
澱粉分解物若しくはサイクロデキストリンを含有
した糖化アルコールで乳化させて香料の分散性を
高め、また乳化させることによりポリビニールピ
ロリドン水溶液とも混合するようにしたものであ
り、フイルムや紙などに塗つて使用できるように
したものである。<Means for Solving the Problems> Therefore, the method for producing a long-lasting fragrance according to the present invention involves adding 1% to 60% (by weight) of a fragrance to a solution of 1% to 60% (by weight) ethanol or methanol of polyvinyl pyrrolidone. % (weight ratio) and stir and mix to suppress scent volatilization with polyvinyl pyrrolidone and increase fragrance retention, and further add 1% to 30% (weight ratio) of hydroxypropyl cellulose.
Adding benzyl alcohol or daythyl phthalate from 1% to 10% (by weight) to further enhance the persistence of the fragrance, or adding cyclodextrin or starch decomposition products containing cyclodextrin or fragrances containing cyclodextrin. It is emulsified with saccharified alcohol to improve the dispersibility of the fragrance, and emulsified so that it can be mixed with an aqueous solution of polyvinyl pyrrolidone, allowing it to be applied to film, paper, etc.
香料類は天然のものでも合成のものでもどちら
でもよく、天然のものは動物性でも植物性でもど
ちらでもよい。 Flavors can be either natural or synthetic, and natural ones can be either animal or vegetable.
ポリビニールピロリドンはビニールピロリドン
の重合体であり、水及びメタノール、エタノール
等の有機溶媒に溶ける。そしてこの発明に係る持
続性香料を紙に塗ると、ポリビニールピロリドン
のエタノール若しくはメタノール溶解液又は水溶
液が蒸発して、ポリビニールピロリドンの皮膜が
でき紙の目の中に入つた香料を丁度被覆するよう
になり香料の揮散を抑制するのである。また、ヒ
ドロキシプロピルセルロースを併用すると、ヒド
ロキシプロピルセルロースがメタノールやエタノ
ールを不活性化するので香料の揮散が抑制される
とともに、ヒドロキシプロピルセルロースが形成
する皮膜は吸湿性が弱いので皮膜が強固なものと
なる。 Polyvinylpyrrolidone is a polymer of vinylpyrrolidone and is soluble in water and organic solvents such as methanol and ethanol. When the persistent fragrance according to the present invention is applied to paper, the ethanol or methanol solution or aqueous solution of polyvinyl pyrrolidone evaporates, forming a film of polyvinyl pyrrolidone that exactly covers the fragrance that has entered the grain of the paper. This suppresses the volatilization of fragrance. In addition, when hydroxypropylcellulose is used in combination, hydroxypropylcellulose inactivates methanol and ethanol, which suppresses the volatilization of fragrances, and the film formed by hydroxypropylcellulose has weak hygroscopicity, so the film becomes strong. Become.
香料類をサイクロデキストリンで乳化すると、
溶液中に均一に混合され易くなるとともに、水溶
液とも混合できるようになる。この発明で使用す
るサイクロデキストリンはα、β、γ等のサイク
ロデキストリン単体でもよいが、サイクロデキス
トリンを含有した澱物分解物やサイクロデキスト
リンを含有した糖化アルコール等を使用してもよ
い。 When fragrances are emulsified with cyclodextrin,
It becomes easier to mix uniformly into a solution, and it also becomes possible to mix with an aqueous solution. The cyclodextrin used in this invention may be a single cyclodextrin such as α, β, or γ, but a decomposed product of lees containing cyclodextrin, a saccharified alcohol containing cyclodextrin, or the like may also be used.
<実施例>
実施例 1
ポリビニールピロリドンの20%(重量比)メタ
ノール溶液とヒドロキシプロピルセルロースの5
%(重量比)メタノール溶液を5:5の割合で混
合したものにラベンダー香油を15%(重量比)加
えて加温しながら10分撹拌し、常温に2時間放置
し、持続性香料を製造した。<Example> Example 1 20% (weight ratio) methanol solution of polyvinyl pyrrolidone and 5% of hydroxypropyl cellulose
Add 15% (weight ratio) of lavender perfume oil to a mixture of 5:5% (weight ratio) methanol solution, stir for 10 minutes while heating, and leave at room temperature for 2 hours to produce a long-lasting fragrance. did.
これをコーターで1平方メートルにつき15g平
均で上質紙に塗布、乾燥して常温で放置したが約
3箇月香りが持続した。 This was applied to high-quality paper using a coater at an average rate of 15g per square meter, dried and left at room temperature, but the scent lasted for about 3 months.
実施例 2
ポリビニールピロリドンの2%(重量比)エタ
ノール溶液にデイエチルフタレイトを5%(重量
比)添加し、これにラベンダー香油を10%(重量
比)加えて加温しながら15分撹拌し、常温に2時
間放置して持続性香料を製造した。Example 2 5% (weight ratio) of daythyl phthalate was added to a 2% (weight ratio) ethanol solution of polyvinyl pyrrolidone, and 10% (weight ratio) of lavender perfume oil was added thereto and stirred for 15 minutes while heating. The mixture was left at room temperature for 2 hours to produce a long-lasting fragrance.
これをコーターで1平方メートルにつき10g平
均でケント紙に塗布、乾燥して常温で放置したが
約2箇月香りが持続した。 This was applied to Kent paper using a coater at an average rate of 10g per square meter, dried and left at room temperature, but the scent lasted for about two months.
実施例 3
ポリビニールピロリドンの50%(重量比)水溶
液にローズ香油をサイクロデキストリンで乳化し
たものを15%(重量比)加えて加温しながら15分
撹拌し、常温に2時間放置して持続性香料を製造
した。Example 3 Add 15% (by weight) of rose perfume oil emulsified with cyclodextrin to a 50% (by weight) aqueous solution of polyvinyl pyrrolidone, stir for 15 minutes while heating, and leave to stand at room temperature for 2 hours to sustain. produced a sexual fragrance.
これをコーターで1平方メートルにつき5g平
均でケント紙に塗布、乾燥して常温で放置したが
約3箇月香りが持続した。 This was applied to Kent paper using a coater at an average rate of 5g per square meter, dried and left at room temperature, but the scent lasted for about 3 months.
実施例 4
ポリビニールピロリドンの2%(重量比)エタ
ノール溶液にラベンダー香油を10%(重量比)添
加し、これにデイエチルフタレイトを5%(重量
比)加えて撹拌した。更にこれにラベンダー香油
をサイクロデキストリンで2%乳化液にしたもの
を加えて加温しながら15分撹拌し、常温に2時間
放置して持続性香料を製造した。Example 4 To a 2% (weight ratio) ethanol solution of polyvinyl pyrrolidone was added 10% (weight ratio) lavender perfume oil, and to this was added 5% (weight ratio) daythyl phthalate and stirred. Furthermore, a 2% emulsion of lavender perfume oil with cyclodextrin was added, stirred for 15 minutes while heating, and left at room temperature for 2 hours to produce a long-lasting fragrance.
これをコーターで1平方メートルにつき10g平
均で上質紙に塗布、乾燥して常温で放置したが約
2箇月香りが持続した。 This was applied to high-quality paper using a coater at an average rate of 10g per square meter, dried and left at room temperature, but the scent lasted for about two months.
実施例 5
ポリビニールピロリドンの5%(重量比)メタ
ノール溶液にコーヒー油を15%(重量比)加え、
これにベンジルアルコールを7%(重量比)添加
して撹拌した。更にヒドロキシプロピルセルロー
スの2%(重量比)メタノール溶液を10%(重量
比)添加して60℃に加温しながら10分撹拌し、常
温に2時間放置して持続性香料を製造した。Example 5 15% (weight ratio) of coffee oil was added to a 5% (weight ratio) methanol solution of polyvinyl pyrrolidone,
7% (weight ratio) benzyl alcohol was added to this and stirred. Further, 10% (by weight) of a 2% (by weight) methanol solution of hydroxypropylcellulose was added, stirred for 10 minutes while heating to 60°C, and left at room temperature for 2 hours to produce a long-lasting fragrance.
これをコーターで1平方メートルにつき8g平
均でケント紙に塗布、乾燥して常温で放置したが
約3箇月香りが持続した。 This was applied to Kent paper using a coater at an average rate of 8g per square meter, dried and left at room temperature, but the scent lasted for about 3 months.
実施例 6
ポリビニールピロリドンの5%(重量比)メタ
ノール溶液に、ラベンダー油をサイクロデキスト
リン含有糖化アルコール(日本食品加工株式会社
製、商品名セルデツクスCH−20H)で乳化した
ものを15%(重量比)加え、これにベンジルアル
コールを7%(重量比)添加して60℃に加温しな
がら15分間撹拌し、常温に2時間放置して持続性
香料を製造した。Example 6 A 5% (weight ratio) methanol solution of polyvinyl pyrrolidone was emulsified with cyclodextrin-containing glycated alcohol (manufactured by Nihon Shokuhin Kako Co., Ltd., trade name Celldex CH-20H) and a 15% (weight ratio) solution of lavender oil was added. ), and 7% (weight ratio) benzyl alcohol was added thereto, stirred for 15 minutes while heating to 60°C, and left at room temperature for 2 hours to produce a long-lasting fragrance.
これをコーターで1平方メートルにつき8g平
均でケント紙に塗布、乾燥して常温で放置したが
約3箇月香りが持続した。 This was applied to Kent paper using a coater at an average rate of 8g per square meter, dried and left at room temperature, but the scent lasted for about 3 months.
実施例 7
サイクロデキストリン含有水飴(日本食品加工
株式会社製、商品名セルデツクスCH−30)200
部に天然桧油200部を加え60℃に加温しながら此
にポリビニールピロリドンの2%(H2O−50%、
エタノール−50%)溶解液を600部を滴下して約
30分間撹拌後常温で放置して持続性香料を製造し
た。Example 7 Cyclodextrin-containing starch syrup (manufactured by Nihon Shokuhin Kako Co., Ltd., trade name Celldex CH-30) 200
200 parts of natural cypress oil was added to the mixture, and 2% of polyvinyl pyrrolidone (H 2 O - 50%,
Add 600 parts of ethanol (50%) solution dropwise to approx.
After stirring for 30 minutes, the mixture was left at room temperature to produce a long-lasting fragrance.
これをコーターで上質紙に塗布、約3箇月香り
を持続させることができた。 This was applied to high-quality paper using a coater, and the scent lasted for about three months.
<発明の効果>
以上のようにこの発明にかかる持続性香料の製
造方法によれば、ポリビニールピロリドンが香料
を被覆して香りの揮散を抑制し、フイルムや紙に
塗つた場合に芳香が永く持続するという効果を有
する持続性香料が製造できるのである。<Effects of the Invention> As described above, according to the method for producing a long-lasting fragrance according to the present invention, polyvinyl pyrrolidone coats the fragrance to suppress the volatilization of the fragrance, and when applied to a film or paper, the fragrance remains for a long time. It is possible to produce a long-lasting fragrance that has a long-lasting effect.
Claims (1)
比)のエタノール又はメタノール溶解液にヒドロ
キシプロピルセルロースを1%〜30%(重量比)
添加し、これに香料類を1%〜60%(重量比)加
えて撹拌混合したことを特徴とする持続性香料の
製造方法。 2 ポリビニールピロリドンの1%〜60%(重量
比)のエタノール又はメタノール溶解液に、ベン
ジルアルコール又はデイエチルフタレイトを1%
〜10%(重量比)添加し、これに香料類を1%〜
60%(重量比)加えて撹拌混合したことを特徴と
する持続性香料の製造方法。 3 ポリビニールピロリドンの1%〜60%(重量
比)のエタノール若しくはメタノール溶解液又は
ポリビニールピロリドンの1%〜60%(重量比)
水溶液に、香料類をサイクロデキストリン若しく
はサイクロデキストリンを含有した澱粉分解物若
しくはサイクロデキストリンを含有した糖化アル
コールで乳化したものを1%〜60%(重量比)加
えて撹拌混合したことを特徴とする持続性香料の
製造方法。 4 ポリビニールピロリドンの1%〜60%(重量
比)のエタノール若しくはメタノール溶解液又は
ポリビニールピロリドンの1%〜60%(重量比)
水溶液に、ベンジルアルコール又はデイエチルフ
タレイトのエタノール溶液若しくはメタノール溶
液を1%〜10%(重量比)添加し、これに香料類
をサイクロデキストリン若しくはサイクロデキス
トリンを含有した澱粉分解物若しくはサイクロデ
キストリンを含有した糖化アルコールで乳化した
ものを1%〜60%(重量比)加えて撹拌混合した
ことを特徴とする持続性香料の製造方法。[Claims] 1. 1% to 30% (by weight) of hydroxypropyl cellulose in a solution of 1% to 60% (by weight) of polyvinyl pyrrolidone in ethanol or methanol.
1. A method for producing a long-lasting fragrance, characterized in that 1% to 60% (by weight) of fragrances are added thereto and stirred and mixed. 2 Add 1% benzyl alcohol or diethyl phthalate to a 1% to 60% (weight ratio) ethanol or methanol solution of polyvinyl pyrrolidone.
~10% (weight ratio) is added, and 1%~ of fragrances are added to this.
A method for producing a long-lasting fragrance characterized by adding 60% (by weight) and stirring and mixing. 3 Ethanol or methanol solution of 1% to 60% (weight ratio) of polyvinyl pyrrolidone or 1% to 60% (weight ratio) of polyvinyl pyrrolidone
1% to 60% (weight ratio) of fragrances emulsified with cyclodextrin, a starch decomposition product containing cyclodextrin, or a saccharified alcohol containing cyclodextrin is added to an aqueous solution, and the mixture is stirred. A method for producing sexual fragrances. 4 Ethanol or methanol solution of 1% to 60% (weight ratio) of polyvinyl pyrrolidone or 1% to 60% (weight ratio) of polyvinyl pyrrolidone
To the aqueous solution, add 1% to 10% (weight ratio) of an ethanolic or methanol solution of benzyl alcohol or daythyl phthalate, and add fragrances to the aqueous solution. A method for producing a long-lasting fragrance, characterized in that 1% to 60% (by weight) of emulsified sugar alcohol is added and mixed by stirring.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60252894A JPS62114909A (en) | 1985-11-13 | 1985-11-13 | Production of durative perfume |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP60252894A JPS62114909A (en) | 1985-11-13 | 1985-11-13 | Production of durative perfume |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62114909A JPS62114909A (en) | 1987-05-26 |
JPH0257428B2 true JPH0257428B2 (en) | 1990-12-04 |
Family
ID=17243645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60252894A Granted JPS62114909A (en) | 1985-11-13 | 1985-11-13 | Production of durative perfume |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62114909A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0983043B1 (en) | 1997-05-21 | 2003-06-25 | Quest International B.V. | Perfume fixatives comprising polyvinylpyrrolidone and hydroxypropyl cellulose |
US9707171B2 (en) | 2012-12-11 | 2017-07-18 | Colgate-Palmolive Company | Antiperspirant/deodorant with alkylated polyvinylpyrrolidone |
-
1985
- 1985-11-13 JP JP60252894A patent/JPS62114909A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS62114909A (en) | 1987-05-26 |
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