CA1124180A - Inclusion compound from volatile odiferous substance with cyclodextrin - Google Patents
Inclusion compound from volatile odiferous substance with cyclodextrinInfo
- Publication number
- CA1124180A CA1124180A CA341,955A CA341955A CA1124180A CA 1124180 A CA1124180 A CA 1124180A CA 341955 A CA341955 A CA 341955A CA 1124180 A CA1124180 A CA 1124180A
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- product according
- synthetic resin
- odiferous
- substance
- 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
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
ABSTRACT
Inclusion compounds of odiferous substances such as fragrances with cyclodextrin can be used for compounding with synthetic resins to provide perfumed resin products of improved life and quality.
Inclusion compounds of odiferous substances such as fragrances with cyclodextrin can be used for compounding with synthetic resins to provide perfumed resin products of improved life and quality.
Description
~ t~ ~
The present invention relates to a stabilized odiferous substance and to a synthetic resin prodllct which continues emitting perfume over a long period o-E time.
In general~ perfumes are substances of high volatility, and moreover are liable to undergo deterioration with time as well as being un-stable to heat. Accordingly, it is extremely dif:Eicult to mix the perfumes into synthetic resins when heat processing them. Temperatures as high as 260C
to 270C are not uncommonly encountered in such processing. Moreover, many such volatile substances are not particularly compatible with many synthetic resins.
The present invention is based on the discovery that many volatile odiferous substances are capable of forming inclusion compounds with cyclo-dextrin which are well suited to incorporating in synthetic resins prior to heat processing to form products such as films, fibres, moldingsJ extrusions, etc.
Accordingly, the present invention provides a stabilised odiferous substance comprising the inclusion compound of a volatile odiferous substance with cyclodextrin.
The invention also provides a perfumed synthetic resin product formed from a synthetic resin composition having admixed therewith the inclusion compound of a volatile odiferous substance with cyclodextrin.
According to the invention, the stabilized odiferous substance is prepared by contacting a volatile odiferous substance with cyclodextrin until an inclusion compound of the cyclodextrin and the odiferous substance has formed.
Furthermore, according to the invention, the perfumed synthetic resin product is prepared by admixing with a synthetic resin the inclusion compound of a volatile odiferous substance with cyclodextrin, and heat pro-~.2~
cessing the mixture to Form said product.
As the odiferous substance J there may be used any such product capable of forming an inclusion compound with cyclodextrin. ~ssential oils such as lavender oil, citronella oil, rose oil, etc., are examples of many naturally occurring fragrances that may be used. Synthetic substances, whether or not they also occur naturally are also useful e.g. geraniol, di-methyl phthalate, etc.
The cyclodextrin may be,~ - or ~- cyclodextrin. The methods of producing these cyclodextrins are disclosed in Japanese patent Nos.
8,865,583 and 91~,137, and in Japanese patent publication 31223/1978.
As synthetic resins there may be used any of the usual resins used for making heat processed products, e.g. polyolefins such as polyethy-lene, polypropylene, polybutene as well as copolymers thereof, acrylo-nitrile polymers such as polyacrylonitrile or acrylonitrile copolymers, vinyl chloride and vinylidene chloride polymers such as polyvinyl chloride or vinyl chloride-vinylidene chloride copolymer, vinyl ester polymers such as polyvinyl acetate, polyvinyl acetate butyrate, etc., polyesters such as polyethylene terephthalate, polyamides such as nylon, and the like. Pre--ferred are those synthetic resins of fairly low melting point which can be formed into products of large surface area, particularly films and fibres, so as to promote a sufficient degree of evaporation of the odiferous in-gredient. For instance, films formed from polyethylene containing the inclusion compound of a fragrance such as rose oil or geraniol with cyclo-dextrin, have been made and exhibit useful fragrant properties for six months or more. Moreover, the character of the perfume remains essentially unchanged during this period. Other molded products can also be produced but because of their relatively smaller surface area to weight ratio, either exhibit a less pronounced fragrance or must be formulated with a larger pro-po~tion of the inclusion compound.
To prepare these synthetic resin products, the inclusion compound is formed by mixing the odiferous substance with the cyclodextrin, preferably accompanied by stirring with the application of moderate heat e.g. to 50C.
The product is then dried~ e.g. in a vacuum drier, and pulverized, or is treated in a pulverizing drier, e.g. at 60C. The particle size of the pro-duct is preferably less than 150 mesh. This powdery product is then suitable for incorporating in synthetic resin compositions e.g. at a level of 1 to 50%
by weight, particularly 5 to 20% by weight. The usual methods of incorporat-ing additives may be employed. Other conventional additives such as colour-ants, stabilizers~ fillers and the like may also be included. When it is necessary to provide coloring to products, the powdered cyclodextrin inclusion compound can be used as a coloring agent. This enables the compatibility with the synthetic resin to be remarkably improved, so that a more stable coloring is obtainable.
The following examples illustrate the invention:
.
Lavender oil and cyclodextrin are mixed and the cyclodextrin in-clusion compound of the lavender oil thus obtained is dried and powdered.
The powder and a synthetic resin molding material are then mixed molded to obtain a synthetic resin product having a pronounced lavender perfume.
Example 2.
Citronella oil is used instead of the lavender oil in the procedure of Example 1, and a synthetic resin product having an insect repellant effect is obtained.
Example 3.
~-Cyclodextrin (85 parts by weight) is added to geraniol (15 parts by weight) and the cyclodextrin inclusion compound is obtained by stirring and mi~ing for hour at a constallt temperature of 50C. The product is powdered by the use oE a vacuum dryer or a pulverizing dryer operated at a temperature of 60C, the product being reduced to a particle siæe of less than 150 mesh. The following various molding goods have been obtained. From a mixture of the powder ~iO parts by weight) and a polyethylene pelletted mold-lng composition ~90 parts by weight~ the :Eollowing products were formed:
(1) By injection molding, products such as cups, pencil stands, brushes and toys with the perfume of rose;
~ 2) By extrusion, particularly by the blown film process, a rose-perfumed wrapping film.
All these products exhibited an ele~ant rose perfume for over 6 months without any change in the character of the perfume. A purse-size toilet tissue container made of the film of item (2) above was pleasant to use, with the perfume being transferred to the tissues.
Example 4.
The following additional products have been obtained from a mixture of the inclusion compound of Example 3 (5 parts by weight) and a fibre-forming polymer such as an acrylonitrile-vinyl acetate copolymer:
(1) By using a melt-spun :Eibre obtained from the above composition, a wig with the perfume of rose was manufactured.
The present invention relates to a stabilized odiferous substance and to a synthetic resin prodllct which continues emitting perfume over a long period o-E time.
In general~ perfumes are substances of high volatility, and moreover are liable to undergo deterioration with time as well as being un-stable to heat. Accordingly, it is extremely dif:Eicult to mix the perfumes into synthetic resins when heat processing them. Temperatures as high as 260C
to 270C are not uncommonly encountered in such processing. Moreover, many such volatile substances are not particularly compatible with many synthetic resins.
The present invention is based on the discovery that many volatile odiferous substances are capable of forming inclusion compounds with cyclo-dextrin which are well suited to incorporating in synthetic resins prior to heat processing to form products such as films, fibres, moldingsJ extrusions, etc.
Accordingly, the present invention provides a stabilised odiferous substance comprising the inclusion compound of a volatile odiferous substance with cyclodextrin.
The invention also provides a perfumed synthetic resin product formed from a synthetic resin composition having admixed therewith the inclusion compound of a volatile odiferous substance with cyclodextrin.
According to the invention, the stabilized odiferous substance is prepared by contacting a volatile odiferous substance with cyclodextrin until an inclusion compound of the cyclodextrin and the odiferous substance has formed.
Furthermore, according to the invention, the perfumed synthetic resin product is prepared by admixing with a synthetic resin the inclusion compound of a volatile odiferous substance with cyclodextrin, and heat pro-~.2~
cessing the mixture to Form said product.
As the odiferous substance J there may be used any such product capable of forming an inclusion compound with cyclodextrin. ~ssential oils such as lavender oil, citronella oil, rose oil, etc., are examples of many naturally occurring fragrances that may be used. Synthetic substances, whether or not they also occur naturally are also useful e.g. geraniol, di-methyl phthalate, etc.
The cyclodextrin may be,~ - or ~- cyclodextrin. The methods of producing these cyclodextrins are disclosed in Japanese patent Nos.
8,865,583 and 91~,137, and in Japanese patent publication 31223/1978.
As synthetic resins there may be used any of the usual resins used for making heat processed products, e.g. polyolefins such as polyethy-lene, polypropylene, polybutene as well as copolymers thereof, acrylo-nitrile polymers such as polyacrylonitrile or acrylonitrile copolymers, vinyl chloride and vinylidene chloride polymers such as polyvinyl chloride or vinyl chloride-vinylidene chloride copolymer, vinyl ester polymers such as polyvinyl acetate, polyvinyl acetate butyrate, etc., polyesters such as polyethylene terephthalate, polyamides such as nylon, and the like. Pre--ferred are those synthetic resins of fairly low melting point which can be formed into products of large surface area, particularly films and fibres, so as to promote a sufficient degree of evaporation of the odiferous in-gredient. For instance, films formed from polyethylene containing the inclusion compound of a fragrance such as rose oil or geraniol with cyclo-dextrin, have been made and exhibit useful fragrant properties for six months or more. Moreover, the character of the perfume remains essentially unchanged during this period. Other molded products can also be produced but because of their relatively smaller surface area to weight ratio, either exhibit a less pronounced fragrance or must be formulated with a larger pro-po~tion of the inclusion compound.
To prepare these synthetic resin products, the inclusion compound is formed by mixing the odiferous substance with the cyclodextrin, preferably accompanied by stirring with the application of moderate heat e.g. to 50C.
The product is then dried~ e.g. in a vacuum drier, and pulverized, or is treated in a pulverizing drier, e.g. at 60C. The particle size of the pro-duct is preferably less than 150 mesh. This powdery product is then suitable for incorporating in synthetic resin compositions e.g. at a level of 1 to 50%
by weight, particularly 5 to 20% by weight. The usual methods of incorporat-ing additives may be employed. Other conventional additives such as colour-ants, stabilizers~ fillers and the like may also be included. When it is necessary to provide coloring to products, the powdered cyclodextrin inclusion compound can be used as a coloring agent. This enables the compatibility with the synthetic resin to be remarkably improved, so that a more stable coloring is obtainable.
The following examples illustrate the invention:
.
Lavender oil and cyclodextrin are mixed and the cyclodextrin in-clusion compound of the lavender oil thus obtained is dried and powdered.
The powder and a synthetic resin molding material are then mixed molded to obtain a synthetic resin product having a pronounced lavender perfume.
Example 2.
Citronella oil is used instead of the lavender oil in the procedure of Example 1, and a synthetic resin product having an insect repellant effect is obtained.
Example 3.
~-Cyclodextrin (85 parts by weight) is added to geraniol (15 parts by weight) and the cyclodextrin inclusion compound is obtained by stirring and mi~ing for hour at a constallt temperature of 50C. The product is powdered by the use oE a vacuum dryer or a pulverizing dryer operated at a temperature of 60C, the product being reduced to a particle siæe of less than 150 mesh. The following various molding goods have been obtained. From a mixture of the powder ~iO parts by weight) and a polyethylene pelletted mold-lng composition ~90 parts by weight~ the :Eollowing products were formed:
(1) By injection molding, products such as cups, pencil stands, brushes and toys with the perfume of rose;
~ 2) By extrusion, particularly by the blown film process, a rose-perfumed wrapping film.
All these products exhibited an ele~ant rose perfume for over 6 months without any change in the character of the perfume. A purse-size toilet tissue container made of the film of item (2) above was pleasant to use, with the perfume being transferred to the tissues.
Example 4.
The following additional products have been obtained from a mixture of the inclusion compound of Example 3 (5 parts by weight) and a fibre-forming polymer such as an acrylonitrile-vinyl acetate copolymer:
(1) By using a melt-spun :Eibre obtained from the above composition, a wig with the perfume of rose was manufactured.
(2) By spinning the same fibre, a cloth was manufactwred with the perfume of rose, and articles such as garments, unbrellas, furoshiki (a traditional Japanese piece of wrapping cloth~, and curtains have been manu-factured. These products exhibited a true rose perfume for over 6 months.
Example 5.
By using dimethyl phthalate instead of geraniol in the procedure of example 3, a polyethylene Eilm with insect-repellant properties has been by the blown-film process. The insect-repellant properties were noticeable for nearly a year.
Example 5.
By using dimethyl phthalate instead of geraniol in the procedure of example 3, a polyethylene Eilm with insect-repellant properties has been by the blown-film process. The insect-repellant properties were noticeable for nearly a year.
Claims (25)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A stabilised odiferous substance comprising the inclusion compound of a volatile odiferous substance with cyclodextrin.
2. A product according to claim 1 wherein the volatile odiferous sub-stance is a naturally occurring fragrance.
3. A product according to claim 1 wherein the volatile odiferous substance is a synthetic substance.
4. A product according to claim 1 wherein the volatile odiferous sub-stance is lavender oil.
5. A product according to claim 1 wherein the volatile odiferous sub-stance is citronella oil.
6. A product according to claim 1 wherein the volatile odiferous sub-stance is geraniol.
7. A product according to claim 1 wherein the volatile odiferous sub-stance is rose oil.
8. A product according to claim 1 wherein the volatile odiferous sub-stance is dimethyl phthalate.
9. A product according to claim 1, 2 or 3 wherein the cyclodextrin is .alpha.-cyclodextrin.
10. A product according to claim 1, 2 or 3 wherein the cyclodextrin is .beta.-cyclodextrin.
11. A product according to claim 1, 2 or 3 wherein the cyclodextrin is .alpha.-cyclodextrin.
12. A method of preparing a stabilised odiferous substance which com-prises contacting a volatile odiferous substance with cyclodextrin until an inclusion compound of the cyclodextrin and the odiferous substance has formed.
13. A method according to claim 12 wherein the reaction is conducted by stirring the ingredients together at a temperature of about 50°C.
14. A method according to claim 12 wherein the reaction product is thereafter dried and pulverised to a particle side of less than 150 mesh.
15. A perfumed synthetic resin product formed from a synthetic resin composition having admixed therewith the inclusion compound of a volatile odiferous substance with cyclodextrin.
16. A product according to claim 15 wherein the synthetic resin is a polyolefin.
17. A product according to claim 15 wherein the synthetic resin is polyethylene.
18. A product according to claim 15 wherein the synthetic resin is an acrylonitrile polymer.
19. A product according to claim 15 wherein the synthetic resin is polyacrylonitrile.
20. A product according to claim 15 wherein the synthetic resin is a vinyl or vinylidene chloride polymer.
21. A product according to claim 15 wherein the synthetic resin is polyvinyl chloride.
22. A perfumed synthetic resin film formed from a film-forming polymer having admixed therewith the inclusion compound of a volatile odiferous sub-stance with cyclodextrin.
23. A perfumed synthetic resin fibre formed from a fibre-forming poly-mer having admixed therewith the inclusion compound of a volatile odiferous substance with cyclodextrin.
24. A method of forming a perfumed synthetic resin product which com-prises admixing with a synthetic resin the inclusion compound of a volatile odiferous substance with cyclodextrin, and heat processing the mixture to form said product.
25. A method according to claim 24 wherein the inclusion compound is employed in the form of a dry powdered material having a particle size of less than 150 mesh.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15413578A JPS5581831A (en) | 1978-12-15 | 1978-12-15 | Preparation of propionaldehyde derivative |
| JP53-154135 | 1978-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1124180A true CA1124180A (en) | 1982-05-25 |
Family
ID=15577650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA341,955A Expired CA1124180A (en) | 1978-12-15 | 1979-12-14 | Inclusion compound from volatile odiferous substance with cyclodextrin |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5581831A (en) |
| CA (1) | CA1124180A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880774A (en) * | 1987-04-14 | 1989-11-14 | Kurita Water Industries, Ltd. | Sustained release aromatic |
| US5238915A (en) * | 1991-02-08 | 1993-08-24 | Wakunaga Seiyaku K.K. | Aromatic composition and method for controlling aroma |
| US5543157A (en) * | 1990-03-06 | 1996-08-06 | The Procter & Gamble Company | Solid consumer product compositions containing small particle clyclodextrin complexes |
| CN116284506A (en) * | 2023-03-22 | 2023-06-23 | 江南大学 | Gamma-cyclodextrin-geraniol derivative and preparation method and application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1329586A (en) | 1998-12-11 | 2002-01-02 | 日产化学工业株式会社 | Processes for preparation of (p-chlorophenyl) propanol derivatives |
-
1978
- 1978-12-15 JP JP15413578A patent/JPS5581831A/en active Pending
-
1979
- 1979-12-14 CA CA341,955A patent/CA1124180A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880774A (en) * | 1987-04-14 | 1989-11-14 | Kurita Water Industries, Ltd. | Sustained release aromatic |
| US5543157A (en) * | 1990-03-06 | 1996-08-06 | The Procter & Gamble Company | Solid consumer product compositions containing small particle clyclodextrin complexes |
| US5552378A (en) * | 1990-03-06 | 1996-09-03 | The Procter & Gamble Company | Solid consumer product compositions containing small particle cyclodextrin complexes |
| US5571782A (en) * | 1990-03-06 | 1996-11-05 | The Procter & Gamble Company | Solid consumer product compositions containing small particle cyclodextrin complexes |
| US5580851A (en) * | 1990-03-06 | 1996-12-03 | The Procter & Gamble Company | Solid consumer product compositions containing small particle cyclodextrin complexes |
| US5635238A (en) * | 1990-03-06 | 1997-06-03 | The Procter & Gamble Company | Solid consumer product compositions containing small particle cyclodextrin complexes |
| US5238915A (en) * | 1991-02-08 | 1993-08-24 | Wakunaga Seiyaku K.K. | Aromatic composition and method for controlling aroma |
| US5382567A (en) * | 1991-02-08 | 1995-01-17 | Wakunaga Seiyaku Kabushiki Kaisha | Aromatic composition and method for controlling aroma |
| CN116284506A (en) * | 2023-03-22 | 2023-06-23 | 江南大学 | Gamma-cyclodextrin-geraniol derivative and preparation method and application thereof |
| CN116284506B (en) * | 2023-03-22 | 2023-12-08 | 江南大学 | Gamma-cyclodextrin-geraniol derivative and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5581831A (en) | 1980-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |