JPH0226507B2 - - Google Patents
Info
- Publication number
- JPH0226507B2 JPH0226507B2 JP58113676A JP11367683A JPH0226507B2 JP H0226507 B2 JPH0226507 B2 JP H0226507B2 JP 58113676 A JP58113676 A JP 58113676A JP 11367683 A JP11367683 A JP 11367683A JP H0226507 B2 JPH0226507 B2 JP H0226507B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- fragrance
- solid
- volatile
- polymer
- 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
- 239000003205 fragrance Substances 0.000 claims description 42
- 239000007787 solid Substances 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- -1 polyoxyethylene Polymers 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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
- 239000000463 material Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])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
- 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
- 125000001312 palmitoyl group Chemical group O=C([*])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
- 125000000913 palmityl 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])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 238000003756 stirring Methods 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Fats And Perfumes (AREA)
Description
この発明は固形芳香剤、特に重合体および揮発
性芳香成分を含有する透明な固形芳香剤に関する
ものである。
便所、風呂場、脱衣場、自動車の中等において
用いられる固形芳香剤として、香料を水に分散さ
せて、ゼラチンやカラゲーナンでゲル化したもの
が提案されているが、これらは不透明で耐熱性が
弱く、通常は容器に入れられており、固形芳香剤
自体は外部から見えないようになつている。
一方、重合体および揮発性芳香成分を含有する
固形芳香剤、すなわち重合体の中に揮発性芳香成
分を閉じ込めた固形芳香剤が提案されている（特
開昭53−99252号、特開昭56−67356号）。この種
の従来の固形芳香剤は不飽和モノマー類に、可溶
化剤を用いて揮発性物質を可溶化した後に重合さ
せたもので、透明でかついかなる形にも成形でき
るが、揮発性物質を可溶化するための可溶化剤が
親水性であるため、高湿度下では、可溶化剤と揮
発性物質が固形芳香剤の表面ににじみ出てしま
い、透明でなくなつたり、べとついたり、あるい
は著しく汚れてしまい、清潔感を損うなどの問題
があつた。
この発明は上記のような従来の問題点を解決す
るためのもので、特定の重合体および揮発性芳香
成分を含有させることにより、重合体中に揮発性
芳香成分を閉じ込め、透明でかつ高温、高湿度に
さらされても、組成および外観に変化をきたさな
い固形芳香剤を提供することを目的としている。
この発明は、下記一般式で示される構造単位
を55重量％以上含む重合体および揮発性芳香成分
を含有する組成物からなることを特徴とする固形
芳香剤である。
（ただし、Ｒは水素原子またはメチル基、AOは
炭素数３〜４のオキシアルキレン基、Ｘは水素原
子または炭素数１〜22のアルキル基、アルケニル
基、アルキルアリール基またはアシル基、ａおよ
びｂはそれぞれ１〜100で、｛ ｝内はブロツク状
に付加していてもランダム状に付加していてもよ
い。）
式において、AOとしてはプロピレンオキシ
ド、ブチレンオキシド、テトラヒドロフランなど
があり、これらはそれぞれ単独で付加していても
よく、また混合状態で付加していてもよい。これ
らのアルキレンオキシドとエチレンオキシドとは
ブロツク状付加、ランダム状付加またはこれらの
組合せでもよく、ブロツク状付加の場合、その順
序は任意である。ａとｂの比は１：100ないし
100：１であるが、特に好ましいのは１：10ない
し10：１である。
Ｘで表わされるアルキル基、アルケニル基、ア
ルキルアリール基、アシル基としては、メチル
基、エチル基、ｎ−プロピル基、イソプロピル
基、ｎ−ブチル基、ｎ−オクチル基、２−エチル
ヘキシル基、ノニル基、ｎ−デシル基、ラウリル
基、トリデシル基、ミリスチル基、パルミチル
基、ステアリル基、ベヘニル基、シクロヘキシル
基、オレイル基、アリル基、ジブチルフエニル
基、オクチルフエニル基、ノニルフエニル基、ア
セチル基、プロパノイル基、ブチロイル基、オク
タノイル基、ラウロイル基、パルミトイル基、ス
テアロイル基、オレオイル基、アクリロイル基、
メタクリロイル基などがある。
本発明における重合体は式の構造単位を55重
量％以上含む重合体であり、他の構造単位を45重
量％以下含んでいてもよい。透明でべとつきのな
い固形芳香剤を得るためには式の構造単位が65
重量％以上、他の構造単位が35重量％以下とする
のが好ましい。この重合体は式の構造単位とな
る単量体であるポリオキシエチレンポリオキシア
ルキレンアクリル酸エステルもしくはメタクリル
酸エステルまたはその誘導体の単独重合体、ある
いはこれらの単量体と重合可能な他の単量体との
共重合体である。
式の構造単位となる単量体と重合可能な他の
単量体としては、アクリル酸、メタクリル酸、ま
たはこれらと炭素数１〜４の１価アルコール、エ
チレングリコール、ポリエチレングリコール、プ
ロピレングリコール、ポリプロピレングリコー
ル、ポリエチレングリコールモノアルキルエーテ
ル、ポリプロピレングリコールモノアルキルエー
テル、グリセリン、ペンタエリスリトール等のア
ルコール類とのエステルなどがあり、式以外の
構造単位はこれらの単量体から導びかれるもので
ある。
本発明の固形芳香剤は上記重合体および揮発性
芳香成分を含有する組成物からなるものである。
揮発性芳香成分としては、天然または合成の一般
に使用されている香料が使用でき、例えばミント
系、フローラル系、かんきつ系などの調合香料が
使用できる。揮発性芳香成分の量は特に制限はな
いが、固形芳香剤の外観、すなわち透明性を保
ち、べとつきがないこと等のほか、芳香を適度に
維持するためには、固形芳香剤組成物中１〜20重
量％の範囲が好ましい。
本発明の固形芳香剤は重合体および揮発性芳香
成分以外に、他の成分例えば着色剤、ドライフラ
ワーのような装飾材などを含有していてもよい。
揮発性芳香成分その他の成分は重合体中に均一に
分散しているのが望ましく、このためには、これ
らの成分を単量体と混合した状態で重合を行い、
生成する重合体中に分散させることができる。
本発明の固形芳香剤は、式の構造単位となる
単量体および必要に応じて他の単量体と、揮発性
芳香成分および他の成分とを混合し、適当な型に
注入してベンゾイルペルオキシド等の硬化剤とと
もに加熱するか、あるいは前記混合物をレドツク
ス系触媒で硬化することによつて製造することが
できる。生成する重合体は所定の形状に成形さ
れ、揮発性芳香成分その他の成分を均一に分散し
た状態で抱き込み、この状態で揮発性芳香成分は
重合体中に溶解し、透明な固形芳香剤が得られ
る。
式の構造単位となる単量体は、アクリル酸、
メタクリル酸またはそのグリコールモノエステル
に、プロピレンオキシド、ブチレンオキシド、テ
トラヒドロフラン等を単独もしくは混合状態で付
加し、次いでエチレンオキシドを付加するか、あ
るいはこれらを逆の順序で付加するか、または前
記アルキレンオキシドとエチレンオキシドを同時
に付加するか、あるいは前述のアルキル基、アル
ケニル基、アルキルアリール基に前記アルキレン
オキシドとエチレンオキシドとを付加させた後、
アクリル酸またはメタクリル酸によりエステル化
するか、さらにはグリコール類に前記アルキレン
オキシドとエチレンオキシドとを付加させた後、
アクリル酸またはメタクリル酸によりエステル化
することにより製造される。
式において、ａ、ｂがそれぞれ１〜100に限
定されるのは、この範囲内でないと、重合体にな
つたときに揮発性芳香成分を溶解して含有してお
くことができず、不透明になつたり、べとついた
りして不都合なためである。式の構造単位が55
重量％以上に限定されるのも同じ理由による。
本発明の固形芳香剤は、特定の重合体および揮
発性芳香成分を含有するので、可溶化剤を用いる
ことなく、重合体中に揮発性芳香成分を溶解させ
ることができ、このため高温、高湿下でも形が崩
れたり、べとついたりすることがなく、優れた外
観および芳香発散効果を維持できるとともに、い
かなる形状にも成形できるなどの効果がある。
次に本発明の実施例について説明する。各例に
おいて部および％は重量部および重量％を示す。
実施例 １
フローラル系香料10ｇ、表１に示す単量体89ｇ
およびベンゾイルペルオキシド１ｇを100ml容ビ
ーカに採り、加熱して均一に溶解させた後、アル
ミはくで覆い、70℃恒温槽中に５時間静置して硬
化させた。室温まで冷却させた後、容器より取り
出し、透明性およびべとつきを観察した。その
後、その組成物を40℃、相対湿度98％の恒温恒湿
槽に48時間静置し、透明性およびべとつきを観察
した。その結果を表１に示す。
表１中、ランダムとあるのは｛ ｝内がランダ
ム状付加物であることを示し、他の化合物の
｛ ｝内は式の順序のブロツク状付加物であるこ
とを示す。また外観の〇は透明、×は不透明を示
し、べとつきの〇はなし、△はわずかにあり、×
は著しいを示す。
This invention relates to solid fragrances, particularly transparent solid fragrances containing polymeric and volatile fragrance components. Solid fragrances for use in toilets, bathrooms, changing rooms, cars, etc. have been proposed by dispersing fragrances in water and gelatinizing them with gelatin or carrageenan, but these are opaque and have poor heat resistance. , usually in a container so that the solid fragrance itself is not visible from the outside. On the other hand, solid fragrances containing polymers and volatile fragrance components, that is, solid fragrances in which volatile fragrance components are trapped in polymers, have been proposed (JP-A-53-99252, JP-A-Sho 56). −67356). This type of conventional solid fragrance is made by polymerizing unsaturated monomers after solubilizing volatile substances using a solubilizer, and is transparent and can be formed into any shape, but does not contain volatile substances. Because the solubilizing agent used for solubilization is hydrophilic, under high humidity conditions, the solubilizing agent and volatile substances may ooze out onto the surface of the solid fragrance, causing it to become opaque, sticky, or There were problems such as it becoming extremely dirty and impairing the sense of cleanliness. This invention is intended to solve the above-mentioned conventional problems. By containing a specific polymer and a volatile aroma component, the volatile aroma component is trapped in the polymer, and it is transparent, high temperature, The object is to provide a solid fragrance that does not change in composition and appearance even when exposed to high humidity. This invention is a solid fragrance characterized by comprising a composition containing a polymer containing 55% by weight or more of a structural unit represented by the following general formula and a volatile fragrance component. (However, R is a hydrogen atom or a methyl group, AO is an oxyalkylene group having 3 to 4 carbon atoms, X is a hydrogen atom or an alkyl group, alkenyl group, alkylaryl group, or acyl group having 1 to 22 carbon atoms, a and b are each from 1 to 100, and the numbers in { } may be added in blocks or randomly.) In the formula, AO includes propylene oxide, butylene oxide, tetrahydrofuran, etc. They may be added alone or in a mixed state. The alkylene oxide and ethylene oxide may be added in block form, random form, or a combination thereof, and in the case of block form addition, the order of addition may be arbitrary. The ratio of a and b is 1:100 or
100:1, particularly preferred is 1:10 to 10:1. The alkyl group, alkenyl group, alkylaryl group, and acyl group represented by X include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, n-octyl group, 2-ethylhexyl group, and nonyl group. , n-decyl group, lauryl group, tridecyl group, myristyl group, palmityl group, stearyl group, behenyl group, cyclohexyl group, oleyl group, allyl group, dibutylphenyl group, octylphenyl group, nonylphenyl group, acetyl group, propanoyl group, Butyroyl group, octanoyl group, lauroyl group, palmitoyl group, stearoyl group, oleoyl group, acryloyl group,
There are methacryloyl groups, etc. The polymer in the present invention is a polymer containing 55% by weight or more of the structural unit of the formula, and may contain 45% by weight or less of other structural units. In order to obtain a transparent, non-sticky solid fragrance, the structural unit of the formula must be 65.
It is preferable that the amount of other structural units is at least 35% by weight. This polymer is a homopolymer of polyoxyethylene polyoxyalkylene acrylic ester or methacrylic ester or its derivatives, which are the monomers forming the structural unit of the formula, or other monomers that can be polymerized with these monomers. It is a copolymer with the body. Other monomers that can be polymerized with the monomer serving as the structural unit of the formula include acrylic acid, methacrylic acid, or monohydric alcohols having 1 to 4 carbon atoms, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene. Examples include esters with alcohols such as glycol, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, glycerin, and pentaerythritol, and structural units other than the formulas are derived from these monomers. The solid fragrance of the present invention consists of a composition containing the above polymer and a volatile fragrance component.
As the volatile aroma component, commonly used natural or synthetic fragrances can be used, such as mint-based, floral-based, citrus-based, and other blended fragrances. There is no particular limit to the amount of volatile aroma components, but in order to maintain the appearance of the solid aroma agent, that is, transparency and non-stickiness, and to maintain a suitable aroma, it is necessary to add 1% to the solid aroma composition. A range of ~20% by weight is preferred. In addition to the polymer and volatile aroma components, the solid fragrance of the present invention may contain other components such as coloring agents and decorative materials such as dried flowers.
It is desirable that the volatile aroma components and other components are uniformly dispersed in the polymer, and for this purpose, polymerization is carried out in a state in which these components are mixed with the monomers.
It can be dispersed in the resulting polymer. The solid fragrance of the present invention is produced by mixing the monomer serving as the structural unit of the formula and other monomers as necessary with volatile fragrance components and other components, and pouring the mixture into a suitable mold to form a benzoyl It can be produced by heating together with a curing agent such as peroxide, or by curing the mixture with a redox catalyst. The resulting polymer is molded into a predetermined shape and envelops the volatile aroma components and other components in a uniformly dispersed state. In this state, the volatile aroma components are dissolved in the polymer and a transparent solid fragrance is created. can get. The monomer serving as the structural unit of the formula is acrylic acid,
Propylene oxide, butylene oxide, tetrahydrofuran, etc. are added alone or in a mixed state to methacrylic acid or its glycol monoester, and then ethylene oxide is added, or these are added in the reverse order, or the above alkylene oxide and ethylene oxide are added. or after adding the alkylene oxide and ethylene oxide to the aforementioned alkyl group, alkenyl group, or alkylaryl group,
After esterification with acrylic acid or methacrylic acid, or further adding the alkylene oxide and ethylene oxide to glycols,
Manufactured by esterification with acrylic acid or methacrylic acid. In the formula, a and b are each limited to 1 to 100. If they are not within this range, volatile aromatic components cannot be dissolved and contained when the polymer is formed, and it becomes opaque. This is because it becomes dry and sticky, which is inconvenient. The structural unit of the formula is 55
It is for the same reason that it is limited to % by weight or more. Since the solid fragrance of the present invention contains a specific polymer and a volatile fragrance component, the volatile fragrance component can be dissolved in the polymer without using a solubilizer. It does not lose its shape or become sticky even under humidity, maintains an excellent appearance and aroma emitting effect, and can be molded into any shape. Next, examples of the present invention will be described. In each example, parts and percentages indicate parts and percentages by weight. Example 1 10g of floral fragrance, 89g of monomer shown in Table 1
Then, 1 g of benzoyl peroxide was placed in a 100 ml beaker, heated to uniformly dissolve it, covered with aluminum foil, and left to stand in a thermostat at 70° C. for 5 hours to cure. After cooling to room temperature, it was taken out from the container and observed for transparency and stickiness. Thereafter, the composition was allowed to stand for 48 hours in a constant temperature and humidity bath at 40° C. and 98% relative humidity, and its transparency and stickiness were observed. The results are shown in Table 1. In Table 1, the word "random" in { } indicates a random adduct, and in other compounds, the compound in { } indicates a block-shaped adduct in the order of the formula. In terms of appearance, ○ indicates transparent, × indicates opaque, ○ indicates no stickiness, △ indicates slight stickiness, and ×
indicates significant.
【表】【table】
【表】【table】
【表】
表１の結果より、本発明品は透明性が優れ、べ
とつきがなく、高温高湿下でも何ら変化しないこ
とがわかる。
実施例 ２
表１のNo.９またはNo.12の単量体組成物89％、フ
ローラル系香料9.99％、赤色系染料0.01％、なら
びにベンゾイルペルオキシド１％からなる組成物
を円板状の容器に流し込み、70℃の恒温槽中に５
時間静置して硬化させ、円板状の透明な固形芳香
剤を得た。得られた固形芳香剤を風呂場に吊して
１ケ月間使用したところ、いずれも芳香を発した
が、No.９の単量体を使用したものは外観、べとつ
きともに製造直後と変わりなく、透明でべとつき
がなかつたが、No.12の単量体を使用したものは２
日目より汗をかくようになり、７日目にひびが入
つた。
実施例 ３
表１のNo.８の単量体組成物89ｇ、ローズ系香料
10ｇ、アスコルビン酸0.3ｇ、および１％塩化第
二鉄水溶液0.4ｇを混合し、均一になるまでかく
はんした。その混合物をドライフラワーがセツト
されたワイングラフに移し、35％過酸化水素水溶
液0.4ｇを加え、ドライフラワーが浮上しないよ
うに注意しながら約２分間かくはんし、均一透明
溶液を得た。かくはん停止後、約５分間経過する
と重合が始まつた。常温の水で冷却して組成物の
温度を50℃以下に１時間保ち、ワイングラス中に
ドライフラワーを閉じ込めた透明な固形芳香剤を
得た。この固形芳香剤を風呂場で１カ月間使用し
たところ、外観は製造直後と変わらず透明で、べ
とつきもなかつた。
以上の結果より、本発明の固形芳香剤は透明性
に優れ、べとつきがなく、高温高湿下で使用して
も変化しないことがわかる。[Table] From the results in Table 1, it can be seen that the product of the present invention has excellent transparency, is not sticky, and does not change at all even under high temperature and high humidity conditions. Example 2 A composition consisting of 89% monomer composition No. 9 or No. 12 in Table 1, 9.99% floral fragrance, 0.01% red dye, and 1% benzoyl peroxide was placed in a disc-shaped container. Pour into a thermostat at 70℃ for 5 minutes.
The mixture was allowed to stand for a period of time to harden, yielding a disk-shaped transparent solid fragrance. When the obtained solid air fresheners were hung in a bathroom and used for one month, all of them emitted a fragrance, but the one using monomer No. 9 had the same appearance and stickiness as it did immediately after production. It was transparent and non-sticky, but the one using monomer No. 12
I started sweating from day one, and cracks appeared on the seventh day. Example 3 89 g of monomer composition No. 8 in Table 1, rose fragrance
10 g, ascorbic acid 0.3 g, and 1% ferric chloride aqueous solution 0.4 g were mixed and stirred until uniform. The mixture was transferred to a wine graph set with dried flowers, 0.4 g of a 35% aqueous hydrogen peroxide solution was added, and stirred for about 2 minutes while being careful not to float the dried flowers to obtain a homogeneous and transparent solution. Polymerization started about 5 minutes after the stirring stopped. The temperature of the composition was kept below 50° C. for 1 hour by cooling with water at room temperature to obtain a transparent solid fragrance containing dried flowers trapped in a wine glass. When this solid air freshener was used in the bathroom for one month, it appeared as transparent as it was immediately after manufacture, and was not sticky. The above results show that the solid fragrance of the present invention has excellent transparency, is not sticky, and does not change even when used under high temperature and high humidity conditions.
Claims (1)
以上含む重合体および揮発性芳香成分を含有する
組成物からなることを特徴とする固形芳香剤。 （ただし、Ｒは水素原子またはメチル基、AOは
炭素数３〜４のオキシアルキレン基、Ｘは水素原
子または炭素数１〜22のアルキル基、アルケニル
基、アルキルアリール基またはアシル基、ａおよ
びｂはそれぞれ１〜100で、｛ ｝内はブロツク状
に付加していてもランダム状に付加していてもよ
い。） ２ 重合体がポリオキシエチレンポリオキシアル
キレンアクリル酸エステルもしくはメタクリル酸
エステルまたはその誘導体の単独重合体である特
許請求の範囲第１項記載の固形芳香剤。 ３ 重合体がポリオキシエチレンポリオキシアル
キレンアクリル酸エステルもしくはメタクリル酸
エステルまたはその誘導体と、アクリル酸、メタ
クリル酸またはこれらと炭素数１〜４の１価アル
コール、エチレングリコール、ポリエチレングリ
コール、プロピレングリコール、ポリプロピレン
グリコール、ポリエチレングリコールモノアルキ
ルエーテル、ポリプロピレングリコールモノアル
キルエーテル、グリセリンまたはペンタエリスリ
トールのエステルとの共重合体である特許請求の
範囲第１項記載の固形芳香剤。 ４ 揮発性芳香成分が香料である特許請求の範囲
第１項ないし第３項のいずれかに記載の固形芳香
剤。 ５ 揮発性芳香成分が組成物中１〜20重量％含有
される特許請求の範囲第１項ないし第４項のいず
れかに記載の固形芳香剤。[Claims] 1. 55% by weight of the structural unit represented by the following general formula
A solid fragrance comprising a composition containing a polymer containing the above and a volatile fragrance component. (However, R is a hydrogen atom or a methyl group, AO is an oxyalkylene group having 3 to 4 carbon atoms, X is a hydrogen atom or an alkyl group, alkenyl group, alkylaryl group, or acyl group having 1 to 22 carbon atoms, a and b are each from 1 to 100, { { } may be added in block form or randomly added.) 2 The polymer is polyoxyethylene polyoxyalkylene acrylic ester or methacrylic ester or a derivative thereof. The solid fragrance according to claim 1, which is a homopolymer of. 3 The polymer is polyoxyethylene polyoxyalkylene acrylic ester or methacrylic ester or a derivative thereof, acrylic acid, methacrylic acid, or a monohydric alcohol having 1 to 4 carbon atoms, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene. The solid fragrance according to claim 1, which is a copolymer with an ester of glycol, polyethylene glycol monoalkyl ether, polypropylene glycol monoalkyl ether, glycerin or pentaerythritol. 4. The solid fragrance according to any one of claims 1 to 3, wherein the volatile aroma component is a fragrance. 5. The solid fragrance according to any one of claims 1 to 4, wherein the volatile fragrance component is contained in an amount of 1 to 20% by weight in the composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58113676A JPS606610A (en) | 1983-06-24 | 1983-06-24 | Solid perfumery |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58113676A JPS606610A (en) | 1983-06-24 | 1983-06-24 | Solid perfumery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS606610A JPS606610A (en) | 1985-01-14 |
| JPH0226507B2 true JPH0226507B2 (en) | 1990-06-11 |
Family
ID=14618339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58113676A Granted JPS606610A (en) | 1983-06-24 | 1983-06-24 | Solid perfumery |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS606610A (en) |
-
1983
- 1983-06-24 JP JP58113676A patent/JPS606610A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS606610A (en) | 1985-01-14 |
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