CA1144074A - Vapor-control agent with perfume absorbed on substrate - Google Patents
Vapor-control agent with perfume absorbed on substrateInfo
- Publication number
- CA1144074A CA1144074A CA000352292A CA352292A CA1144074A CA 1144074 A CA1144074 A CA 1144074A CA 000352292 A CA000352292 A CA 000352292A CA 352292 A CA352292 A CA 352292A CA 1144074 A CA1144074 A CA 1144074A
- Authority
- CA
- Canada
- Prior art keywords
- perfume
- vapor
- control agent
- weight
- moles
- 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
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
- A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
- A61L9/044—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating with the help of an organic compound other than a macromolecular compound
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/015—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone
- A61L9/04—Disinfection, sterilisation or deodorisation of air using gaseous or vaporous substances, e.g. ozone using substances evaporated in the air without heating
Abstract
ABSTRACT
A method for controlling the rate of evaporation or rate of release of a perfume from an absorbent sub-strate in a continous action air freshener comprising in-corporating into the perfume from 10 to 900% by weight based on the weight of the perfume of a vapor control agent selected from the group consisting of nonionic sur-factants having an average of from 1 to 5 moles of ethy-lene oxide per molecule, a compound having the structure:
wherein m and n are intigers, the same or different, sel-ected from 1 to 4, and R is an alkyl group having from 12 to 18 carbon atoms, a compound having the structure:
A method for controlling the rate of evaporation or rate of release of a perfume from an absorbent sub-strate in a continous action air freshener comprising in-corporating into the perfume from 10 to 900% by weight based on the weight of the perfume of a vapor control agent selected from the group consisting of nonionic sur-factants having an average of from 1 to 5 moles of ethy-lene oxide per molecule, a compound having the structure:
wherein m and n are intigers, the same or different, sel-ected from 1 to 4, and R is an alkyl group having from 12 to 18 carbon atoms, a compound having the structure:
Description
This invention relates to a method of controlling the rate of release of perfumes from continuous action air fresheners and more particularly to controlling the rate of release of perfumes from continuous action air fresheners having cellulosic substrates as the perfume reservoir and generator.
Continuous action air fresheners are slow dif-fusers which release perfume into an environment at a rela-tively controlled rate over an extended period of time to 10 impart a desirable perfume to cover or mask undesirable odors which may be present. There have been numerous materials described as reservoirs for continuous action air fresheners. Some of these reservoirs such as car-rageenin gels as disclosed in U.S. Patent 2,927,055, metal crosslinked carboxymetyl cellulose gels as dis-closed in U.S. Patent 3j969,280 and amylose gels as de-scribed ïn U.S. Patent 4,071,616 inherently release per-fume o~er an extended period of time~as the gel evaporates or sublimes into the atmosphere. There also have been 20 attempts to control the release of perfumes from cellu-losic substrates such as described in Belgian Patent 865,425 which utilizes specific nonionic surfactants, namely, octyl and nonyl phenols having relatively high degree of ethoxylation and British Patent 1,517,410 which describes the use of polyethylene or another plastic film to surround a cellulosic substrate to control the rate of release of th~ perfume from the substrate.
The various carrageenin, CMC and amylose gels, .although effective as continuous action air fresheners are ..
.: ~
. , .
' 4~7~
, ~ 2 --somewhat difficult to prepare and all have some form of syneresis present in the product. Furthermore, these gels typically have a useful life of 21-30 days. Furthermore, these products are heavy because of the high water con-tent and must be protected from freezing as the gels gen-erally are not freeze-thaw sta~le.
On the oth~r hand, the products using cellulosic substrates as reservoirs and generators as typified by the above-noted Belgian and British patents offer certain 1~ advantages over the gel-t~pe forms. However, the structure as exemplified by the above-noted Brit;sh Patent is dif-ficult to pac~age because the plastic or polyethylene film wrapper is permeable to the perfume. When this pac~age is sealed in an outer impermeable package, the perfume diffuses-through the inner package to form a damp or wet surface on the film when the package is opened. This can be solved by using various ampoules to contain the perfume, however, this also has some disadvantages. The use of a vapor retardant as taught in the Belgian patent acts to 2Q slow down the perfume without requiring artificial bar-riers and the like. The particular vapor retardants de-scribed in this patent do not control the rate of release of the perfume to an acceptable degree for extended pro-duct life.
U. S. Patent 3,016,192 contains a general dis-closure of the use of nonionic surfactants similar to those taught in the Belgian patent in combination with cellulosic su~strates and perfumes.
It has now been discovered, however, that cer-30 tain surfactants having a particular critical degree ofethoxylation have superior vapor retardant properties as compared to the nonionic surfactants generally disclosed in Belgian Patent 865,425 and U.S. Patent 3,016,1~9.
The present invention provides a method for con-trolling the rate of evaporation of a volatile perfume from an absor~ent substrate in a continuous action air freshener comprising incorporating into the perfume from 10 to ~0~% by weight, ~ased on the weight of the perfume, o~ a vapor-control agent selected from the group consisting : - 3 -of nonionic surfactants having an average of from l to 5 moles of ethylene oxide per molecule, a compound having the structure:
HO-(.CH2)m N- -R
HO-(CH2)n /
wherein m and n are intigers, which may be the same or different, selected from l to 4 and R is an alkyl group having from 12 to 1~ carbon atoms, a compound having the structure HO-(CH2)m \ / (CH2)m-OH
N-C-R .NH
HO-(.CH2)n ~ (.CH2)n-OH
wherein m and n are intigers, which may be the same or different, selected f.rom l to 4, and R is an alkyl group having from 12 to 18 carbon atoms., and mixtures thereof.
It is the primary object of the present in-vention to provide an improved method for controlling the rate of release of perfumes from absorbent substrates.
The method of the present invention for control-ling the rate of release of a volatile perfume from an absorbent substrate in which the perfume has been impregna-ted in a continuous action air freshener comprises in-corporating into the perfume from 10 to 900% by weight based on the weight of the perfume of a vapor-control agent selected from the group consisting of nonionic sur-factants having an average of from l to 5 moles of ethy-lene oxide per molecule, a compound having the formula HO-~CH2)m \
N-C-R
HO-(CH2)n ~
4~
wherein-m and n are intigers, the same or different, selected from 1 to 4 and R is an alkyl group having from 12 to 18 carbon atoms, a compound having the formula HO-(CH2)m~ / t CH2 ) m~OH
N-C-R . NH
HO-(CH2)n (CH2)n-OH
wherein m and n are intigers, the same or different, selected from 1 to 4 and R is an alkyl group having from 12 to 18 carbon atoms, and mixtures thereof; incorporatingthe perfume and the vapor control agent in-to the absorbent substrate the absorbent substrate including from 2 to 20 grams of the perfume.
When used in the instant specification and in attached claims, the term "cellulosic substrate" refers to a fibrous, woven or non-woven, substrate formed from a cellulosic material such as cotton, paper, cardboard, pulp, and the likè, in a relatively flat sheet form. This term does not refer to and does not include carboxymethylcellulose gels as described in U.S. Patent 3,9fi9,280.
Any absorbent substrate can be utilized as the substrate in the method of the present invention. The substrate should be sufficiently absorbent so as to absorb sufficient perfume and vapor-control agent without ap~reciable free moisture which would give a wet or damp surface. The substrates should be sufficiently absorbent to absorb from 50 to 500% by weight, based on the weight of the substrate, of perfume and vapor-control agent. It is preferred that the substrate be sufficiently-30 absorbent to absorb 100 to 400% by weight, based on substrate weight, of perfume and vapor-control agent. The density of the substrate is not particularly critical; however, it is preferred that the substrate have a bulk density within the range of from about 0.15 g/cc to 1.0 g/cc and preferably 0.20 g/cc to 0.60 g/cc.
Suitable substrates include cotton batting, cotton fiber based non-woven substrates, including filter substrates, wood pulp sheets such as pulp sheets formed from .
- : : . :
, ~ ~9 4~74 prehydrolysed Kraft hardwood, sulfated pine and other soft woods and the like. Highly absorbent papers are suitable as are synthetic non-woven materials such as polyester felts, sintered polyethylene and other absorbent sub-strates. Other similar absorbent substrates are suit-able so long as~-the absorbency and density are within the above ranges.
Although any of the a~ove-noted substrates can be used in the method of the present invention, cellulosic 10 substrates are preferred. Furthermore, the following cel-lulosic substrates are particularly preferred: cotton based non-woven filter substrate, sulfated pine pulp and absorbent paper. Each of the above substrates are com-mercially available materials.
Furthermore, the absorbent substrate can be sub-stantially any size or shape. The only requirement being that sufficient surface area is exposed or can be exposed to the atmosphere to release the perfume. These air fresheners can be arranged or stored in various dispensing 20 devices such as described in U.S. Patents 3,964,684 or 4,077,183. Other suitable package designs which sufficient-ly afford the large surface area can be utilized.
As the perfumes used in the continuous action air fresheners, almost any perfume designed Eor use in con-tinuous action a;r fresheners which is available from a commercial perfumer can be utilized. Typ;cally, perfumes are complex proprietary mixtures of ingredients to proYide a specific scent or fragrance. Perfumes generally are de-scribed in terms of their vapor characteristics and in 30 terms of the notes or fragrances which the perfumes emit.
Suita~le perfume classes for the use in the continuous action air fresheners of the present invention include floral per-fumes, such as rose, various flower garden mixtures, lavender, and the like, various citrus fragrances like ]emon, lime, citrus mixtures, and the like, various evergreen or out-door fragrances such as pine, spruce, and the like; var-ious herb or spice fragrances, such as cinnamon, vanilla ~, , , , ' , ~
~ ~4~4 strawberry, etc. Substantially any fragrance can be used utilized ;n the method of the present invention so long as the fragrance is compatible with the substrate chosen.
As noted earlier, perfumes available from commer-cial perfume suppliers generally are mixtures of various ingredients which have various components which evaporate or vaporize at different rates. By controlling the rate of evaporation of the more ~uickly evaporating materials, the profile of the perfume can be altered to improve the frayrance and extend the effective life of the perfume.
10 Generally it is desirable to have the perfume have an initial lift of fragrance which provides an initial im-pression of Pragrance which is the continued on in the less volatile substances. The choice of a particular perfume is up to the taste of the individual user. The amount of perfume used is a matter of choice. Generally from 2 to 20 grams of perfume is incorporated into each generator.
In order to slow down or control the evapora-tion or release oE the perfumes from the absorbent sub-strate, it is necessary to incorporate a vapor-control 20agent. If the perfumes are merely impregnated or in-corporated into the absorbent substrate without the use of a vapor-control agent, the perfumes quickly evaporate within a period of one or ten days after the package is opened. However, by utilizing vapor-control agents and particular utilizing the vapor-control agents descrihed and claimed in the instant method, i-t is possible to ex-tend the use and usable lifetime of these perfumes from an absorbent substrate to a period of from 30 to 60 days. Of course, the useful life of a generator is highly dependent 30 on the amount and type of perfume incorporated into the substrate as well as the amount and type of vapor-control agent.
Furthermore, it has been found that the vapor-control agents used in the present invention improve the fragrance profile of aged perfume which are impregnated in cellulosic substrates. These vapor control agents appear to inhibit rapid volatilization of the lighter fractions in ~-..
the perfume so that thP perfume plus vapor~control ~gent is preferred over perfume alone.
It has been found that from 10 to 900% by weight, based on the weight of the perfume, the vapor-control agent can be incorporated into the perfume. It is pre-ferred that the vapor-control agent be present in an amount of from 50 to 30~ by weigh-t, based on the weight of the perfume. It is most preferred to incorporate Erom 75 to 200~ by weight, based on the weight of the perfume, of the 10 vapor control agent.
The first class of vapor-control agents useful in the method of the present invention are the nonionic surfactants having an average of from 1 to 5 moles, and preferably 1 to 3 moles, of ethylene oxide per molecule.
These nonionic surfactants fall into a number of general - classes of nonionic sur~actants such as the octyl and nonyl phenol ethoxylates, the straight chain alcohol ethoxylates, the branch chain ethoxylates and the like. The only cri-terion with regard to the nonionic surfactants be that 20 the nonionic surfactants each have an average degree of ethoxylation of from 1 to 5 moles of ethylene oxide per molecule. This excludes the use of higher ethoxylates such as described in the Belgian Patent 782,565, which do not function as efficiently or as effectively as these lower ethoxylate nonionic surfactants. Specific nonionic sur-factants which are usable in the method of the present in-~ention include the following: the octyl phenols having an average of one to five moles of ethylene oxide such as the Triton X series from Rohm and Haas, nonyl phenols ha~-30 ing an a~erage of one to five moles of ethylene oxide - such as the Surfonic N series from Jefferson Chemicals, the primary alcohol etholylates such as the Neodol series from Shell Chemicals, and the secondary alcohol ethyxylates such as the 'rergitol'S series from Union Carbide and the like.
Certain specific nonionic surfactants include: octyl phenol + 1.0 EO, octyl phenol + 3.5 EO, octyl phenol +
4.5 EO nonyl phenol + 1 EO, nonyl phenol + 4 EO, mixed C12-C15 alc~hols + 3 EO, mixed Cl~-C15 alcohol + 3 EO, mixed C12-C15 alcohol + 5 EO, mixed C12-C15 secondary al-cohol + 3 EO, mixed C12~C15 secondary alcohol + 5 EO, stear-deno~e~ ~r6de ~a~
7~a A second class of surfactants usable as a vapor-control agent in -the present invention are the di-lower alkyl, i.e. having l to 4 carbon atoms, alcohol fatty am-ides. These materials are exemplified by the following formula:
HO-(CH2~m \ Cl N- -R
( 2)n /
wherein m and n are intigers and can be the same or dif-10 ferent selected from 1 to 4, and R is an alkyl group hav-ing from 12 to 18 carbon atoms. It is preferred that the lower alkyl group be the same and the preferred lower alkyl group is ethyl. With regard to the higher alkyl group it is preferred that this alkyl group be selected from the following groups: dodecaryl, tetradecaryl, hexadecaryl, octadecaryl and mixtures such as produced from coco acids and other natural mlxtures. The most preferred alkyl group is lauryl. Suitable amides include diethanol amide laurate, diethanol amide palmitate, diethanol amide 20 stearate, dimethanol amide laurate, dipropanol amide laurate, dibutanol amide laurate. Furthermore r the pre-ferred amides of this class are the diethanol amide laurate.
A third class of compounds are related to this second group of compounds and are described as super-amides.
These complex compounds are thought to have the following co-ordinate formula:
HO-(CH2)m ~ ~O / (~H2)m~H
N- -R . NH _ HO-(CH2)n (CH2)n OH
30 wherein m and n are intigers and can be the same or dif-ferent, preferably the same, selected from l to 4, and R
is a alkyl group having from 12 to 18 carbon atoms. The preferred values for m and n are 2 while the preferred values for the alkyl group are the lauryl, coco and stearyl, ., ., . ~ .
7~
g with lauryl being the most preferred.
Preferred vapor-control agents are the nonyl phenols plus 1 to 5 E0 groups, octyl phenols plus 1 to 5 EO groups, the dialkanol amides laurates. The most preferred are the octyl and nonyl phenols plus 1 to 3 EO groups.
The vapor-control agents can be incorporated into the perfume by simple mixing technique prior to the impregnating or incorporation of the perfume, vapor-con-trol agent into the substrate. It is necessary to hermet-ically seal the impregnated or treated absorbent sub-strate until the container is used to prevent premature perfume loss. Suitable methods of such sealing are well known in the art and need not be described here.
The method of the present invention will be fully described by the following examples wherein all parts and per~entages are by weight and all temperatures and degrees Celcius. These examples shall in no way be construed as limiting the scope o~ the subject matter of the present invention.
- A mixture-of 6 grams of a floral perfume and 4 grams of Surfonin N-10, a nonyl phenol+lE nonionic2 surfactant were impregnated into J-5 pads having 42 in surface area from Filter Materials. The pad is placed in a dispenser as disclosed in U.S. Patent 4,220,281, issued September 2, 1980. As a control 6 grams of the same perfume on the same substrate material was placed in an identical package. The packages were exposed to the atmosphere at room temperature and the weight loss were measured at various intervals as shown in Table I.
Table I
Control Example 1 No. of Days Grams Lost Grams Lost 151 1.50 1.06
Continuous action air fresheners are slow dif-fusers which release perfume into an environment at a rela-tively controlled rate over an extended period of time to 10 impart a desirable perfume to cover or mask undesirable odors which may be present. There have been numerous materials described as reservoirs for continuous action air fresheners. Some of these reservoirs such as car-rageenin gels as disclosed in U.S. Patent 2,927,055, metal crosslinked carboxymetyl cellulose gels as dis-closed in U.S. Patent 3j969,280 and amylose gels as de-scribed ïn U.S. Patent 4,071,616 inherently release per-fume o~er an extended period of time~as the gel evaporates or sublimes into the atmosphere. There also have been 20 attempts to control the release of perfumes from cellu-losic substrates such as described in Belgian Patent 865,425 which utilizes specific nonionic surfactants, namely, octyl and nonyl phenols having relatively high degree of ethoxylation and British Patent 1,517,410 which describes the use of polyethylene or another plastic film to surround a cellulosic substrate to control the rate of release of th~ perfume from the substrate.
The various carrageenin, CMC and amylose gels, .although effective as continuous action air fresheners are ..
.: ~
. , .
' 4~7~
, ~ 2 --somewhat difficult to prepare and all have some form of syneresis present in the product. Furthermore, these gels typically have a useful life of 21-30 days. Furthermore, these products are heavy because of the high water con-tent and must be protected from freezing as the gels gen-erally are not freeze-thaw sta~le.
On the oth~r hand, the products using cellulosic substrates as reservoirs and generators as typified by the above-noted Belgian and British patents offer certain 1~ advantages over the gel-t~pe forms. However, the structure as exemplified by the above-noted Brit;sh Patent is dif-ficult to pac~age because the plastic or polyethylene film wrapper is permeable to the perfume. When this pac~age is sealed in an outer impermeable package, the perfume diffuses-through the inner package to form a damp or wet surface on the film when the package is opened. This can be solved by using various ampoules to contain the perfume, however, this also has some disadvantages. The use of a vapor retardant as taught in the Belgian patent acts to 2Q slow down the perfume without requiring artificial bar-riers and the like. The particular vapor retardants de-scribed in this patent do not control the rate of release of the perfume to an acceptable degree for extended pro-duct life.
U. S. Patent 3,016,192 contains a general dis-closure of the use of nonionic surfactants similar to those taught in the Belgian patent in combination with cellulosic su~strates and perfumes.
It has now been discovered, however, that cer-30 tain surfactants having a particular critical degree ofethoxylation have superior vapor retardant properties as compared to the nonionic surfactants generally disclosed in Belgian Patent 865,425 and U.S. Patent 3,016,1~9.
The present invention provides a method for con-trolling the rate of evaporation of a volatile perfume from an absor~ent substrate in a continuous action air freshener comprising incorporating into the perfume from 10 to ~0~% by weight, ~ased on the weight of the perfume, o~ a vapor-control agent selected from the group consisting : - 3 -of nonionic surfactants having an average of from l to 5 moles of ethylene oxide per molecule, a compound having the structure:
HO-(.CH2)m N- -R
HO-(CH2)n /
wherein m and n are intigers, which may be the same or different, selected from l to 4 and R is an alkyl group having from 12 to 1~ carbon atoms, a compound having the structure HO-(CH2)m \ / (CH2)m-OH
N-C-R .NH
HO-(.CH2)n ~ (.CH2)n-OH
wherein m and n are intigers, which may be the same or different, selected f.rom l to 4, and R is an alkyl group having from 12 to 18 carbon atoms., and mixtures thereof.
It is the primary object of the present in-vention to provide an improved method for controlling the rate of release of perfumes from absorbent substrates.
The method of the present invention for control-ling the rate of release of a volatile perfume from an absorbent substrate in which the perfume has been impregna-ted in a continuous action air freshener comprises in-corporating into the perfume from 10 to 900% by weight based on the weight of the perfume of a vapor-control agent selected from the group consisting of nonionic sur-factants having an average of from l to 5 moles of ethy-lene oxide per molecule, a compound having the formula HO-~CH2)m \
N-C-R
HO-(CH2)n ~
4~
wherein-m and n are intigers, the same or different, selected from 1 to 4 and R is an alkyl group having from 12 to 18 carbon atoms, a compound having the formula HO-(CH2)m~ / t CH2 ) m~OH
N-C-R . NH
HO-(CH2)n (CH2)n-OH
wherein m and n are intigers, the same or different, selected from 1 to 4 and R is an alkyl group having from 12 to 18 carbon atoms, and mixtures thereof; incorporatingthe perfume and the vapor control agent in-to the absorbent substrate the absorbent substrate including from 2 to 20 grams of the perfume.
When used in the instant specification and in attached claims, the term "cellulosic substrate" refers to a fibrous, woven or non-woven, substrate formed from a cellulosic material such as cotton, paper, cardboard, pulp, and the likè, in a relatively flat sheet form. This term does not refer to and does not include carboxymethylcellulose gels as described in U.S. Patent 3,9fi9,280.
Any absorbent substrate can be utilized as the substrate in the method of the present invention. The substrate should be sufficiently absorbent so as to absorb sufficient perfume and vapor-control agent without ap~reciable free moisture which would give a wet or damp surface. The substrates should be sufficiently absorbent to absorb from 50 to 500% by weight, based on the weight of the substrate, of perfume and vapor-control agent. It is preferred that the substrate be sufficiently-30 absorbent to absorb 100 to 400% by weight, based on substrate weight, of perfume and vapor-control agent. The density of the substrate is not particularly critical; however, it is preferred that the substrate have a bulk density within the range of from about 0.15 g/cc to 1.0 g/cc and preferably 0.20 g/cc to 0.60 g/cc.
Suitable substrates include cotton batting, cotton fiber based non-woven substrates, including filter substrates, wood pulp sheets such as pulp sheets formed from .
- : : . :
, ~ ~9 4~74 prehydrolysed Kraft hardwood, sulfated pine and other soft woods and the like. Highly absorbent papers are suitable as are synthetic non-woven materials such as polyester felts, sintered polyethylene and other absorbent sub-strates. Other similar absorbent substrates are suit-able so long as~-the absorbency and density are within the above ranges.
Although any of the a~ove-noted substrates can be used in the method of the present invention, cellulosic 10 substrates are preferred. Furthermore, the following cel-lulosic substrates are particularly preferred: cotton based non-woven filter substrate, sulfated pine pulp and absorbent paper. Each of the above substrates are com-mercially available materials.
Furthermore, the absorbent substrate can be sub-stantially any size or shape. The only requirement being that sufficient surface area is exposed or can be exposed to the atmosphere to release the perfume. These air fresheners can be arranged or stored in various dispensing 20 devices such as described in U.S. Patents 3,964,684 or 4,077,183. Other suitable package designs which sufficient-ly afford the large surface area can be utilized.
As the perfumes used in the continuous action air fresheners, almost any perfume designed Eor use in con-tinuous action a;r fresheners which is available from a commercial perfumer can be utilized. Typ;cally, perfumes are complex proprietary mixtures of ingredients to proYide a specific scent or fragrance. Perfumes generally are de-scribed in terms of their vapor characteristics and in 30 terms of the notes or fragrances which the perfumes emit.
Suita~le perfume classes for the use in the continuous action air fresheners of the present invention include floral per-fumes, such as rose, various flower garden mixtures, lavender, and the like, various citrus fragrances like ]emon, lime, citrus mixtures, and the like, various evergreen or out-door fragrances such as pine, spruce, and the like; var-ious herb or spice fragrances, such as cinnamon, vanilla ~, , , , ' , ~
~ ~4~4 strawberry, etc. Substantially any fragrance can be used utilized ;n the method of the present invention so long as the fragrance is compatible with the substrate chosen.
As noted earlier, perfumes available from commer-cial perfume suppliers generally are mixtures of various ingredients which have various components which evaporate or vaporize at different rates. By controlling the rate of evaporation of the more ~uickly evaporating materials, the profile of the perfume can be altered to improve the frayrance and extend the effective life of the perfume.
10 Generally it is desirable to have the perfume have an initial lift of fragrance which provides an initial im-pression of Pragrance which is the continued on in the less volatile substances. The choice of a particular perfume is up to the taste of the individual user. The amount of perfume used is a matter of choice. Generally from 2 to 20 grams of perfume is incorporated into each generator.
In order to slow down or control the evapora-tion or release oE the perfumes from the absorbent sub-strate, it is necessary to incorporate a vapor-control 20agent. If the perfumes are merely impregnated or in-corporated into the absorbent substrate without the use of a vapor-control agent, the perfumes quickly evaporate within a period of one or ten days after the package is opened. However, by utilizing vapor-control agents and particular utilizing the vapor-control agents descrihed and claimed in the instant method, i-t is possible to ex-tend the use and usable lifetime of these perfumes from an absorbent substrate to a period of from 30 to 60 days. Of course, the useful life of a generator is highly dependent 30 on the amount and type of perfume incorporated into the substrate as well as the amount and type of vapor-control agent.
Furthermore, it has been found that the vapor-control agents used in the present invention improve the fragrance profile of aged perfume which are impregnated in cellulosic substrates. These vapor control agents appear to inhibit rapid volatilization of the lighter fractions in ~-..
the perfume so that thP perfume plus vapor~control ~gent is preferred over perfume alone.
It has been found that from 10 to 900% by weight, based on the weight of the perfume, the vapor-control agent can be incorporated into the perfume. It is pre-ferred that the vapor-control agent be present in an amount of from 50 to 30~ by weigh-t, based on the weight of the perfume. It is most preferred to incorporate Erom 75 to 200~ by weight, based on the weight of the perfume, of the 10 vapor control agent.
The first class of vapor-control agents useful in the method of the present invention are the nonionic surfactants having an average of from 1 to 5 moles, and preferably 1 to 3 moles, of ethylene oxide per molecule.
These nonionic surfactants fall into a number of general - classes of nonionic sur~actants such as the octyl and nonyl phenol ethoxylates, the straight chain alcohol ethoxylates, the branch chain ethoxylates and the like. The only cri-terion with regard to the nonionic surfactants be that 20 the nonionic surfactants each have an average degree of ethoxylation of from 1 to 5 moles of ethylene oxide per molecule. This excludes the use of higher ethoxylates such as described in the Belgian Patent 782,565, which do not function as efficiently or as effectively as these lower ethoxylate nonionic surfactants. Specific nonionic sur-factants which are usable in the method of the present in-~ention include the following: the octyl phenols having an average of one to five moles of ethylene oxide such as the Triton X series from Rohm and Haas, nonyl phenols ha~-30 ing an a~erage of one to five moles of ethylene oxide - such as the Surfonic N series from Jefferson Chemicals, the primary alcohol etholylates such as the Neodol series from Shell Chemicals, and the secondary alcohol ethyxylates such as the 'rergitol'S series from Union Carbide and the like.
Certain specific nonionic surfactants include: octyl phenol + 1.0 EO, octyl phenol + 3.5 EO, octyl phenol +
4.5 EO nonyl phenol + 1 EO, nonyl phenol + 4 EO, mixed C12-C15 alc~hols + 3 EO, mixed Cl~-C15 alcohol + 3 EO, mixed C12-C15 alcohol + 5 EO, mixed C12-C15 secondary al-cohol + 3 EO, mixed C12~C15 secondary alcohol + 5 EO, stear-deno~e~ ~r6de ~a~
7~a A second class of surfactants usable as a vapor-control agent in -the present invention are the di-lower alkyl, i.e. having l to 4 carbon atoms, alcohol fatty am-ides. These materials are exemplified by the following formula:
HO-(CH2~m \ Cl N- -R
( 2)n /
wherein m and n are intigers and can be the same or dif-10 ferent selected from 1 to 4, and R is an alkyl group hav-ing from 12 to 18 carbon atoms. It is preferred that the lower alkyl group be the same and the preferred lower alkyl group is ethyl. With regard to the higher alkyl group it is preferred that this alkyl group be selected from the following groups: dodecaryl, tetradecaryl, hexadecaryl, octadecaryl and mixtures such as produced from coco acids and other natural mlxtures. The most preferred alkyl group is lauryl. Suitable amides include diethanol amide laurate, diethanol amide palmitate, diethanol amide 20 stearate, dimethanol amide laurate, dipropanol amide laurate, dibutanol amide laurate. Furthermore r the pre-ferred amides of this class are the diethanol amide laurate.
A third class of compounds are related to this second group of compounds and are described as super-amides.
These complex compounds are thought to have the following co-ordinate formula:
HO-(CH2)m ~ ~O / (~H2)m~H
N- -R . NH _ HO-(CH2)n (CH2)n OH
30 wherein m and n are intigers and can be the same or dif-ferent, preferably the same, selected from l to 4, and R
is a alkyl group having from 12 to 18 carbon atoms. The preferred values for m and n are 2 while the preferred values for the alkyl group are the lauryl, coco and stearyl, ., ., . ~ .
7~
g with lauryl being the most preferred.
Preferred vapor-control agents are the nonyl phenols plus 1 to 5 E0 groups, octyl phenols plus 1 to 5 EO groups, the dialkanol amides laurates. The most preferred are the octyl and nonyl phenols plus 1 to 3 EO groups.
The vapor-control agents can be incorporated into the perfume by simple mixing technique prior to the impregnating or incorporation of the perfume, vapor-con-trol agent into the substrate. It is necessary to hermet-ically seal the impregnated or treated absorbent sub-strate until the container is used to prevent premature perfume loss. Suitable methods of such sealing are well known in the art and need not be described here.
The method of the present invention will be fully described by the following examples wherein all parts and per~entages are by weight and all temperatures and degrees Celcius. These examples shall in no way be construed as limiting the scope o~ the subject matter of the present invention.
- A mixture-of 6 grams of a floral perfume and 4 grams of Surfonin N-10, a nonyl phenol+lE nonionic2 surfactant were impregnated into J-5 pads having 42 in surface area from Filter Materials. The pad is placed in a dispenser as disclosed in U.S. Patent 4,220,281, issued September 2, 1980. As a control 6 grams of the same perfume on the same substrate material was placed in an identical package. The packages were exposed to the atmosphere at room temperature and the weight loss were measured at various intervals as shown in Table I.
Table I
Control Example 1 No. of Days Grams Lost Grams Lost 151 1.50 1.06
2 1.87 1.36 2.28 1.66 6 2.47 1.83 7 2.71 2.01 2013 3.27 2.46 14 3.48 2.63 16 3.63 2.70 19 3.77 2.77
3.90 2.89 2522 4.16 3.06 34 4.&0 3.53
4.79 3.46 37 4.9g 3.62 44 5.22 3.81 3047 5.42 4.01 51 5.39 4.03
5.49 4.15 58 5.54 4.22 5.62 4.40 As is apparent from Table I, the addition of the specific nonionic surfactant reduced the loss of perfume to the atmosphere. The sample without surfactant lost over one-'~ ; ~' - , 7D~
half the perfume in 13 days while 22 days were required for the mixture of EXAMPLE 1.
, ' 7~
A mixture of 4 grams of a rose perfume oil was mixed with 6 grams of nonyl phenol + 1 EO. The mixture was impregnated into a 3.25" x 4.50" x 0.160" sheet of J-5 paper from Filter Materials, weighing 10.69 grams. The sheet was exposed to the air at room temperature and the weight loss was recorded at various intervals. In tne control, 4 grams of the same perfume was impregnated in a similar paper ~eighing 11.00 grams. The results are shown in Table II.
Table II
Control Example 2 No. of Days Grams Lost Grams Lost 1 0.~6 0.52 2 1.49 0.90 3 1.98 1.20
half the perfume in 13 days while 22 days were required for the mixture of EXAMPLE 1.
, ' 7~
A mixture of 4 grams of a rose perfume oil was mixed with 6 grams of nonyl phenol + 1 EO. The mixture was impregnated into a 3.25" x 4.50" x 0.160" sheet of J-5 paper from Filter Materials, weighing 10.69 grams. The sheet was exposed to the air at room temperature and the weight loss was recorded at various intervals. In tne control, 4 grams of the same perfume was impregnated in a similar paper ~eighing 11.00 grams. The results are shown in Table II.
Table II
Control Example 2 No. of Days Grams Lost Grams Lost 1 0.~6 0.52 2 1.49 0.90 3 1.98 1.20
6 2.13 1.19
7 2.20 1.21 2.40 1.34 2013 2.62 1.51 14 2.70 1.56 16 2.75 ~ 1.57 28 3.11 1.9 31 3.30 2.17 34 3.33 2.27 38 3.27 2.26 3.31 2.46 52 3.49 2.74 59 3.52 2.86 3070 3O51 3.03 As is apparent from the Table, the modified perfume of EXAMPLE 2 was much more controlled taking 31 days to lose 2.17 grams while the perfume alone lost 2.13 grams in 6 days. This clearly shows control.
....
EXAMPL~ 3 Some 4.0 grams of lemon perfume oil was mixed with 4.0 grams of a nonyl phenol plus 1 EO nonionic sur-factant. The mixture and a control using only 4.0 grams of the same lemon perfume were impregnated in 3.25" x 4.50" x 0.160" sheets of Filter Materials J-5 paper.
EXAMPLE 3 and the control were exposed to the air at room temperature. The weight loss data is shown in Table III. --Ta~le III
Days Example 3 Control Grams Lost Grams Lost 2 2.40 2.87 3 2.51 3.07 6 2.75 3.29 7 2.85 3.32 9 2.86 3.33 21 3.08 3.38 24 3.17 3.44 27 3.22 3.49 31 3.24 3.38 38 3.34 3.41 ., .. ~ ' : .
, 7~
Some 5.0 g of a lemon perf-ume oil was mixed with 7.50 g of nonyl phenol plus 1 EO nonionic surfactant.
This was ~mpregnated in a 3.25" x 4.50" x 0.160" sheet of Filter Materials J-5 paper. The weight loss data is shown in Table IV. Althou h there is no control, the wei~ht loss data has a flatter curve than other controls.
EXAMPLE 4 was repeated exceyt that 7.50 g of 10 Superamide 100 CG, a coconut diethanolamide superamide was used in place of the nonionic surfactant. The weight loss data is shown in Table I~. This surfactant provided bet-ter control than the nonionic of EXAMPLE 4.
Table IV
Days Example 4 5 Grams Lost Grams Lost 1 3.14 3.18 2 3.53 3.40 3.84 3.50 7 3.96 3.53 9 4.02 3.56 16 4.26 3.71 23 4.40 3.87 4.37 3.84 ~.43 3.87 44 4.47 3.86 58 4.54 3.98 .
., .
i74 COMPARATrVE EX~PLES 1 - 3 Three nonyl phenol ethoylates having more than 5 moles of ethylene oxide were mixed with four grams of lemon perfume oil. In each ins-tance 6 grams of non-ionic was used. The mixtures were impregnated on a 4.25" x 4.50"
sulfatate R-J pulp. The weight loss data is shown as Ta~le VI.
Ta~le ~I
Comp. Ex. 1 2 3 Control Moles f 61 8.52 33 Ethylene Oxide Days Wt. Loss G. Wt. Loss G. Wt. Loss ~. Wt. Loss ~
2 2.99 3.06 3.11 3.63 14 3.40 3.44 3.56 3.74 17 3.46 3.49 3.61 3.75 21 3.60 3.66 3.75 -3.85 23 3.64 3.68 3.78 3.87 ~J.~
1 - Surfonic N-60 2 - Surfonic N-85 20 3 - Igepol C0-880 Although the higher ethoxylates retarded perfume evaporation somewhat, the rate is higher than the lower ethoxylates.
~de~o~es ~rale~ark .:
.. ~ ' ' ' , i7~L
Some 5.0 gms of the perfume oil of EXAMPLE 3 mixed with 7.5 grms of nonyl phenol -~ 3 EO nonionic sur-factant was impregnated on a 3.25" x 4.50" x 0.160" sheet of Filter Materials J-5 paper. This pad was placed in-side a molded polyethylene package having adjustable open-ings. The openings were opened fully. As a comparison, 5.0 gms of the same perfume was mixed with 7.5 gms of nonyl phenol. The weight loss data is shown below:
Example 6 CE 4 Days Grams Lost Grams Lost 1 2.32 2.58 2 3.03 3.17 3 3.22 3.34 6 3.52 3.65 7 3.66 3.82
....
EXAMPL~ 3 Some 4.0 grams of lemon perfume oil was mixed with 4.0 grams of a nonyl phenol plus 1 EO nonionic sur-factant. The mixture and a control using only 4.0 grams of the same lemon perfume were impregnated in 3.25" x 4.50" x 0.160" sheets of Filter Materials J-5 paper.
EXAMPLE 3 and the control were exposed to the air at room temperature. The weight loss data is shown in Table III. --Ta~le III
Days Example 3 Control Grams Lost Grams Lost 2 2.40 2.87 3 2.51 3.07 6 2.75 3.29 7 2.85 3.32 9 2.86 3.33 21 3.08 3.38 24 3.17 3.44 27 3.22 3.49 31 3.24 3.38 38 3.34 3.41 ., .. ~ ' : .
, 7~
Some 5.0 g of a lemon perf-ume oil was mixed with 7.50 g of nonyl phenol plus 1 EO nonionic surfactant.
This was ~mpregnated in a 3.25" x 4.50" x 0.160" sheet of Filter Materials J-5 paper. The weight loss data is shown in Table IV. Althou h there is no control, the wei~ht loss data has a flatter curve than other controls.
EXAMPLE 4 was repeated exceyt that 7.50 g of 10 Superamide 100 CG, a coconut diethanolamide superamide was used in place of the nonionic surfactant. The weight loss data is shown in Table I~. This surfactant provided bet-ter control than the nonionic of EXAMPLE 4.
Table IV
Days Example 4 5 Grams Lost Grams Lost 1 3.14 3.18 2 3.53 3.40 3.84 3.50 7 3.96 3.53 9 4.02 3.56 16 4.26 3.71 23 4.40 3.87 4.37 3.84 ~.43 3.87 44 4.47 3.86 58 4.54 3.98 .
., .
i74 COMPARATrVE EX~PLES 1 - 3 Three nonyl phenol ethoylates having more than 5 moles of ethylene oxide were mixed with four grams of lemon perfume oil. In each ins-tance 6 grams of non-ionic was used. The mixtures were impregnated on a 4.25" x 4.50"
sulfatate R-J pulp. The weight loss data is shown as Ta~le VI.
Ta~le ~I
Comp. Ex. 1 2 3 Control Moles f 61 8.52 33 Ethylene Oxide Days Wt. Loss G. Wt. Loss G. Wt. Loss ~. Wt. Loss ~
2 2.99 3.06 3.11 3.63 14 3.40 3.44 3.56 3.74 17 3.46 3.49 3.61 3.75 21 3.60 3.66 3.75 -3.85 23 3.64 3.68 3.78 3.87 ~J.~
1 - Surfonic N-60 2 - Surfonic N-85 20 3 - Igepol C0-880 Although the higher ethoxylates retarded perfume evaporation somewhat, the rate is higher than the lower ethoxylates.
~de~o~es ~rale~ark .:
.. ~ ' ' ' , i7~L
Some 5.0 gms of the perfume oil of EXAMPLE 3 mixed with 7.5 grms of nonyl phenol -~ 3 EO nonionic sur-factant was impregnated on a 3.25" x 4.50" x 0.160" sheet of Filter Materials J-5 paper. This pad was placed in-side a molded polyethylene package having adjustable open-ings. The openings were opened fully. As a comparison, 5.0 gms of the same perfume was mixed with 7.5 gms of nonyl phenol. The weight loss data is shown below:
Example 6 CE 4 Days Grams Lost Grams Lost 1 2.32 2.58 2 3.03 3.17 3 3.22 3.34 6 3.52 3.65 7 3.66 3.82
8 3.66 3.83
9 3.73 3.87 3.68 3.87 - 20 13 3.82 3.84 14 3.92 4.12 3.97 4.16 16 3.98 4.17 17 3.86 3.99 4.~4 4.23 21 4.~6 4.24 22 4.14 4.32 27 4.09 4.26 28 4.13 4.32 7~
EXAMPLE 7 AND COMPARATI~E EXAMPLE 5 Some 5 grams of a rose perfume were mixed with 3.33 grams of nonyl phenol plus 1 mole EO nonionic sur-factant. The mixture was impregnated on a 3.25" x 4.50"
x 0.160" sheet of Filter Materials J-5 paper. In Com-parative Example 5 only 5.0 grams of the same perfume was impregnated on the paper. Each paper was aged 44 days in the atmosphere. The aged papers were presented to a panel of 7 people to determine which paper is preferred. All 7
EXAMPLE 7 AND COMPARATI~E EXAMPLE 5 Some 5 grams of a rose perfume were mixed with 3.33 grams of nonyl phenol plus 1 mole EO nonionic sur-factant. The mixture was impregnated on a 3.25" x 4.50"
x 0.160" sheet of Filter Materials J-5 paper. In Com-parative Example 5 only 5.0 grams of the same perfume was impregnated on the paper. Each paper was aged 44 days in the atmosphere. The aged papers were presented to a panel of 7 people to determine which paper is preferred. All 7
10 indicated that the paper of EXAMPLE 7 was preferred as having a stronger and better rose.
This indicates that the quality of the perfume is actually improved by the addition of the nonionic sur-factan-t.
EXAMPLE 7 was repeated using a lemon and a blend of perfumes characterized as a mixture of piney, herbal and citrus. For both the lemon and the blend the nonionic improved the perfume preferences after aging when compared 20 tc simi~ar ased ian!Fles of the perrume not containing the nonionic.
,
This indicates that the quality of the perfume is actually improved by the addition of the nonionic sur-factan-t.
EXAMPLE 7 was repeated using a lemon and a blend of perfumes characterized as a mixture of piney, herbal and citrus. For both the lemon and the blend the nonionic improved the perfume preferences after aging when compared 20 tc simi~ar ased ian!Fles of the perrume not containing the nonionic.
,
Claims (11)
1. A method for controlling the rate of evapora-tion of a volatile perfume from an absorbent substrate in a continuous action air freshener comprising incorporating into the perfume from 10 to 900% by weight, based on the weight of the perfume, of a vapor-control agent selected from the group consisting of nonionic surfactants having an average of from 1 to 5 moles of ethylene oxide per molecule, a compound having the structure:
wherein m and n are intigers, which may be the same or different, selected from 1 to 4 and R is an alkyl group having from 12 to 18 carbon atoms, a compound having the structure:
wherein m and n are intigers, which may be the same or different, selected from 1 to 4, and R is an alkyl group having from 12 to 18 carbon atoms, and mixtures thereof.
wherein m and n are intigers, which may be the same or different, selected from 1 to 4 and R is an alkyl group having from 12 to 18 carbon atoms, a compound having the structure:
wherein m and n are intigers, which may be the same or different, selected from 1 to 4, and R is an alkyl group having from 12 to 18 carbon atoms, and mixtures thereof.
2. The method of claim 1 wherein the vapor-control agent is a nonionic surfactant having an average of from 1 to 5 moles of ethylene oxide per molecule.
3. The method of claim 2, wherein the vapor-control agent has an average of from 1 to 3 moles of ethyl-ene oxide per molecule.
4. The method of claim 1 or 2 or 3 wherein the vapor-control agent is present in an amount of from 50 to 300% by weight based on the weight of the perfume.
5. The method of claims 1 or 2 or 3 wherein the vapor-control agent is present in an amount of from 75 to 200% by weight based on the weight of the perfume.
6. The method of claim 1 wherein the vapor-control agent is selected from the group consisting of nonyl phenol ethoxylates having an average of from 1 to 5 moles of ethylene oxide per molecule, octyl phenol ethoxylates having an average of from 1 to 5 moles of ethylene oxide per molecule, dialkyanolamide laurates having alkyl groups selected from methyl, ethyl, propyl and butyl and mixtures thereof.
7. The method of claim 1 wherein the vapor-control agent is selected from the group consisting of nonyl phenol ethoxylates having an average of from 1 to 3 moles of ethylene oxide per molecule, octyl phenol ethoxy-lates having an average of from 1 to 3 moles of ethylene oxide per molecule and mixtures thereof.
8. The method of claim 1 wherein the vapor-control agent is nonyl phenol ethoxylate having one mole of ethylene oxide per molecule.
9. The method of claims 6 or 7 or 8 wherein the vapor-control agent is present in an amount of from 50 to 300% by weight based on the weight of the perfume.
10. The method of claims 6 or 7 or 8 wherein the vapor-control agent is present in an a mount of from 75 to 200% by weight based on the weight of the perfume.
11. The method of claim 1 wherein the perfume is present in the substrate in an amount of from 3 to 15 grams.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40,807 | 1979-05-21 | ||
| US06/040,807 US4320873A (en) | 1979-05-21 | 1979-05-21 | Controlled release air freshener using an absorbent generator |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1144074A true CA1144074A (en) | 1983-04-05 |
Family
ID=21913068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000352292A Expired CA1144074A (en) | 1979-05-21 | 1980-05-20 | Vapor-control agent with perfume absorbed on substrate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4320873A (en) |
| EP (1) | EP0021586B1 (en) |
| JP (1) | JPS5628764A (en) |
| AT (1) | ATE3506T1 (en) |
| AU (1) | AU534247B2 (en) |
| CA (1) | CA1144074A (en) |
| DE (1) | DE3063444D1 (en) |
| NZ (1) | NZ193633A (en) |
| PH (1) | PH15931A (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4413779A (en) * | 1981-03-23 | 1983-11-08 | De Laire, Inc. | Vapor dispersing device |
| US4419326A (en) * | 1981-04-30 | 1983-12-06 | De Laire, Inc. | Vapor dispersing process |
| IT1174572B (en) * | 1984-07-06 | 1987-07-01 | Montedison Spa | SLOW DISPENSER OF VOLATILE PRODUCTS |
| EP0194896B2 (en) * | 1985-03-15 | 1995-01-11 | Immanuel J. Wilk | Methods and devices for controlled release |
| US4666671A (en) * | 1985-04-03 | 1987-05-19 | Givaudan Corporation | Method for deodorizing urinals and toilet bowls with fragranced gel blocks |
| JPS6337179A (en) * | 1986-07-31 | 1988-02-17 | Taiyo Koryo Kk | Transparent gelatinous aromatic composition |
| US4808569A (en) * | 1986-10-24 | 1989-02-28 | Gaf Corporation | Fragrance additive |
| US4773128A (en) * | 1987-01-13 | 1988-09-27 | Teepak, Inc. | Apparatus and methods of stuffing food casings to provide dimensionally uniform products |
| US4913350A (en) * | 1988-03-18 | 1990-04-03 | Givaudan Corporation | Air freshener device using external capillaries |
| US4793555A (en) * | 1988-04-22 | 1988-12-27 | Dow Corning Corporation | Container, method and composition for controlling the release of a volatile liquid from an aqueous mixture |
| US5074997A (en) * | 1990-01-25 | 1991-12-24 | Riley And Wallace | Filter and process for making a filter for dispersing ingredients into effluent |
| US5899381A (en) * | 1997-02-21 | 1999-05-04 | Ceramatec, Inc. | Electrochemical device for delivery of volatile substances |
| US7234648B2 (en) * | 2003-10-31 | 2007-06-26 | The Procter And Gamble Company | Volatile substance-controlling composition |
| KR101831786B1 (en) * | 2010-09-17 | 2018-02-23 | 에스프린팅솔루션 주식회사 | Smell dilution unit and electrophotographic image forming apparatus having the same |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3016199A (en) * | 1957-07-26 | 1962-01-09 | Kurt R Keydel | Deodorizer container |
| US2927055A (en) * | 1958-09-05 | 1960-03-01 | Airkem Inc | Air treating gel and method of preparing the same |
| US3303091A (en) * | 1964-09-10 | 1967-02-07 | Johnson & Son Inc S C | Pesticidal aerosol compositions |
| FR1590898A (en) * | 1968-11-06 | 1970-04-20 | ||
| FR1603822A (en) * | 1968-11-18 | 1971-06-07 | Steady-evaporation insecticide based onddvp | |
| US3688985A (en) * | 1970-12-09 | 1972-09-05 | Walter H Engel | Plastic article of manufacture impregnated with volatile matter |
| US4078050A (en) * | 1974-11-27 | 1978-03-07 | Hart Una L | Deodorant compositions and process of deodorizing using 2,4-disubstituted 6-hydroxy-1,3-dioxane compounds |
| GB1453279A (en) * | 1975-03-07 | 1976-10-20 | Johnson & Son Inc S C | Solid air freshener gels |
| GB1515630A (en) * | 1975-11-24 | 1978-06-28 | Johnson & Son Inc S C | Air freshener gels based on amylose |
| GB1517410A (en) | 1976-01-05 | 1978-07-12 | Johnson & Son Inc S C | Slow diffusing air freshener |
| US4051159A (en) * | 1976-01-12 | 1977-09-27 | Avon Products, Inc. | Transparent fragrance releasing composition and method of making same |
| US4067824A (en) * | 1976-09-27 | 1978-01-10 | Anheuser-Busch, Incorporated | Gelled perfume |
| SE421531B (en) * | 1977-02-01 | 1982-01-04 | Bush Boake Allen Ltd | POLYMER COMPOSITION CONTAINING A REGULATED DELIVERY ACTIVE, FLATFUL COMPONENT, PROCEDURE FOR PREPARING THE COMPOSITION AND USING THEREOF |
| CA1096311A (en) | 1977-03-29 | 1981-02-24 | Lary L. Foley | Alkyl phenol ether of polyethylene glycol as stabilizer of air freshener |
-
1979
- 1979-05-21 US US06/040,807 patent/US4320873A/en not_active Expired - Lifetime
-
1980
- 1980-05-06 NZ NZ193633A patent/NZ193633A/en unknown
- 1980-05-09 AU AU58247/80A patent/AU534247B2/en not_active Ceased
- 1980-05-15 DE DE8080301593T patent/DE3063444D1/en not_active Expired
- 1980-05-15 EP EP80301593A patent/EP0021586B1/en not_active Expired
- 1980-05-15 AT AT80301593T patent/ATE3506T1/en not_active IP Right Cessation
- 1980-05-20 CA CA000352292A patent/CA1144074A/en not_active Expired
- 1980-05-21 JP JP6656880A patent/JPS5628764A/en active Granted
- 1980-05-21 PH PH24054A patent/PH15931A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5628764A (en) | 1981-03-20 |
| NZ193633A (en) | 1982-03-23 |
| PH15931A (en) | 1983-04-29 |
| EP0021586A1 (en) | 1981-01-07 |
| EP0021586B1 (en) | 1983-05-25 |
| JPS6139823B2 (en) | 1986-09-05 |
| AU534247B2 (en) | 1984-01-12 |
| AU5824780A (en) | 1981-11-26 |
| DE3063444D1 (en) | 1983-07-07 |
| US4320873A (en) | 1982-03-23 |
| ATE3506T1 (en) | 1983-06-15 |
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