CA1085672A - Particulate flavoring materials and method of producing same - Google Patents
Particulate flavoring materials and method of producing sameInfo
- Publication number
- CA1085672A CA1085672A CA267,623A CA267623A CA1085672A CA 1085672 A CA1085672 A CA 1085672A CA 267623 A CA267623 A CA 267623A CA 1085672 A CA1085672 A CA 1085672A
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- Canada
- Prior art keywords
- flavoring
- particulate
- weight
- matrix
- starch
- 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.)
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
Abstract
PARTICULATE FLAVORING MATERIALS
AND METHOD OF PRODUCING SAME
Abstract of the Disclosure Particulate flavoring materials are provided having a flavoring agent fixed in a particulate matrix containing a di-saccharide and certain carbohydrates of hydrophilic colloids and starch hydrolysates. The ratio of the disaccharide to the carbo-hydrate in the particulate matrix is such that at least about 30% flavoring agent per total particulate matrix is entrapped in the matrix and less than about 4% flavoring agent per total matrix is unentrapped on the surface of the particles. The particulate flavoring materials herein provided thus effectively fix flavoring volatiles for storage without vaporization and/or chemical alteration of the flavoring power. The high quantity of flavoring agent contained per unit weight of matrix material in the flavoring particles provides significant economics with regard to storage, transportation, and manufacturing costs.
Particulate flavoring compositions are prepared by forming an aqueous mixture of a flavoring oil, a disaccharide and a carbohydrate of the hydrophilic colloid and hydrolysed starch type, and then spray-drying the aqueous mixture under the influence of heat. The method produces particulate flavoring compositions in a very effective manner and enables substantial amounts on the order of about 30 to 60% flavoring agent entrap-ment in the particulate matrix. The method also provides for very efficient utilization of flavoring agents by the fixation or all or nearly all of the flavoring agent starting material in the particulate end-product.
AND METHOD OF PRODUCING SAME
Abstract of the Disclosure Particulate flavoring materials are provided having a flavoring agent fixed in a particulate matrix containing a di-saccharide and certain carbohydrates of hydrophilic colloids and starch hydrolysates. The ratio of the disaccharide to the carbo-hydrate in the particulate matrix is such that at least about 30% flavoring agent per total particulate matrix is entrapped in the matrix and less than about 4% flavoring agent per total matrix is unentrapped on the surface of the particles. The particulate flavoring materials herein provided thus effectively fix flavoring volatiles for storage without vaporization and/or chemical alteration of the flavoring power. The high quantity of flavoring agent contained per unit weight of matrix material in the flavoring particles provides significant economics with regard to storage, transportation, and manufacturing costs.
Particulate flavoring compositions are prepared by forming an aqueous mixture of a flavoring oil, a disaccharide and a carbohydrate of the hydrophilic colloid and hydrolysed starch type, and then spray-drying the aqueous mixture under the influence of heat. The method produces particulate flavoring compositions in a very effective manner and enables substantial amounts on the order of about 30 to 60% flavoring agent entrap-ment in the particulate matrix. The method also provides for very efficient utilization of flavoring agents by the fixation or all or nearly all of the flavoring agent starting material in the particulate end-product.
Description
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Background oE t:he Invention A cons~derable amoullt of effort h~ been devoted Eor many year~ to provide solid particulate flavorin~ materials in which a flavoring oil is contained in the particulate matrix. Various attempts have been made to fix essential flavoring oils in many different types of organic matrices to provide stable free flowing powders which contain the flavoring oils for Elavor release when incorporated into ~ ;
many types of foods. Typical examples of flavor fixation are illustrated in rather recent patents, namely, U.S.
Patents 3,314,803; 3,554,76B and 3,736,149. These patents illustrate attempts to incorporate a flavoring oil or volatile ingredient into a carbohydrate matrix, particularly volatile acetaldehyde. With respect to U.S. Patent 3,314,803, the fixation of acetaldehyde in mannitol is disclosed wherein relatively Iow amounts of acetaldehyde on the order of about 10% or less are initially fixed in a matrix with deterioration or loss of the fixed acetaldehyde over a period of time. In connection with UcS. Patent 3,554,768, a composition is 20 ` disclosed which contains acetaldehyde fixed in a carbohydrate such as either a hydrophilic colloid, partially hydrolysed starch or sugar, and mixtures of such car~ohydrates are sugyested. More particularly, the 3,55~,768 patent in its operating examples suggests that either lactose, lactose-maltose, larch gum, tapioca dextrin and gum arabic may be employed as matrices for a method of spray-drying aqueous acetaldehyde compositions to provide spray-dried producks, but only low levels of acetaldehyde fixation are achieved and such levels are reduced upon storage~ In connection with U.S. Patent 3,736~149, flavoring compositions are disclosed which comprise a flavoring agent including acetaldehyde fixed in a matrix material containing lactose~ a hydxocolloid , bm:
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gum and a starch hydrolysate, wherein ~he patent: sugg~sts that p~efercl~ly about. 5 to 50% of lactose is pre~ent in the ~tabilized acetaldehyde compositions. Furthermore, in the 3,736,149 patent the operating examples disclose that the lactose is present in an amount of about 15-20% by weight with the balance being a mixture of starch hydrolysate and hydrocolloid gum of about 80-85~ by weight based upon the three components. In both the 3,554,768 and 3,736,149 ~;~
patents, initial flavor fixation levels of about 10% or less are obtained with a reduction in the flavor level with the passage of storage time. The above mentioned patents are merely illustrative of the considerable volume of patent literature related to the fixation of flavoring agents in ~;
various matrices and it is not the purpose in this rather brief background of the invention to fully detail all of the ~;
prior art in this area. Merely illustrative of other patents included in such patent literature are United States Patent Nos. 2,088,622; 2,258,567; 2,369,847; 2,555,465; 2,673,157i `~
Background oE t:he Invention A cons~derable amoullt of effort h~ been devoted Eor many year~ to provide solid particulate flavorin~ materials in which a flavoring oil is contained in the particulate matrix. Various attempts have been made to fix essential flavoring oils in many different types of organic matrices to provide stable free flowing powders which contain the flavoring oils for Elavor release when incorporated into ~ ;
many types of foods. Typical examples of flavor fixation are illustrated in rather recent patents, namely, U.S.
Patents 3,314,803; 3,554,76B and 3,736,149. These patents illustrate attempts to incorporate a flavoring oil or volatile ingredient into a carbohydrate matrix, particularly volatile acetaldehyde. With respect to U.S. Patent 3,314,803, the fixation of acetaldehyde in mannitol is disclosed wherein relatively Iow amounts of acetaldehyde on the order of about 10% or less are initially fixed in a matrix with deterioration or loss of the fixed acetaldehyde over a period of time. In connection with UcS. Patent 3,554,768, a composition is 20 ` disclosed which contains acetaldehyde fixed in a carbohydrate such as either a hydrophilic colloid, partially hydrolysed starch or sugar, and mixtures of such car~ohydrates are sugyested. More particularly, the 3,55~,768 patent in its operating examples suggests that either lactose, lactose-maltose, larch gum, tapioca dextrin and gum arabic may be employed as matrices for a method of spray-drying aqueous acetaldehyde compositions to provide spray-dried producks, but only low levels of acetaldehyde fixation are achieved and such levels are reduced upon storage~ In connection with U.S. Patent 3,736~149, flavoring compositions are disclosed which comprise a flavoring agent including acetaldehyde fixed in a matrix material containing lactose~ a hydxocolloid , bm:
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gum and a starch hydrolysate, wherein ~he patent: sugg~sts that p~efercl~ly about. 5 to 50% of lactose is pre~ent in the ~tabilized acetaldehyde compositions. Furthermore, in the 3,736,149 patent the operating examples disclose that the lactose is present in an amount of about 15-20% by weight with the balance being a mixture of starch hydrolysate and hydrocolloid gum of about 80-85~ by weight based upon the three components. In both the 3,554,768 and 3,736,149 ~;~
patents, initial flavor fixation levels of about 10% or less are obtained with a reduction in the flavor level with the passage of storage time. The above mentioned patents are merely illustrative of the considerable volume of patent literature related to the fixation of flavoring agents in ~;
various matrices and it is not the purpose in this rather brief background of the invention to fully detail all of the ~;
prior art in this area. Merely illustrative of other patents included in such patent literature are United States Patent Nos. 2,088,622; 2,258,567; 2,369,847; 2,555,465; 2,673,157i `~
2,702,262; 2,80g,895; 2,824,807; 2,856,291; 2,857,281; -2,929,723; 2,935,409; 3,041,180; 3,264,11~; 3,336,139;
3,764,346 and 3,787,592.
In view of the vast body of art in the area of fixed flavor compositions, to applicant's knowledge, it has , not heretofore been previously reported or known that volatile flavoring agents could be fixed in certain carbohydrate matrices in significantly large amounts without ;
detrimental amounts of flavoring agents on the particle surfaces, and it has not heretofore been known to provide a method for producing such particulate flavor compositions in an effective manner without loss of flavoring components.
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:~ Summary o the ~nvention ,~, Thls inv~ntion is directed to novel particulate flavoring m~terials and methods of producing same. The ~' parkiculate flavoring materials, according to the principles of this inven~ion, comprise a flavoring agent fixed in a particulate matrix of a disaccharide and certain ~; carbohydrate materials. It has been found that particulate ;-~
flavoring materials can be produced which contain substantial amounts of flavoring agent entrapped in the particle matrix ~; 10 on the order of at least about 30% to about 60% or more of the flavoring agent per total particle weight and wherein less than about 4~ of flavoring agent is unentrapped on the surface of the particles.
Furthermore, it has been found that a particulate flavoring composition can be prepared by formin~ an aqueous mixture of ~he flavoring agent, a disaccharide and a carbohydrate ma~eria~ and spray-drying the aqueous mixture und~r the in~luence of heak to form a particulate flavoring composition having substantial amounts of fixed flavoring , 20 agent in the matrix with only an insignificant amount of unentrapped agent on the surface of the particles. Another ! advantage o~ the method is that all ox neaxly all o~ th~
flavoring agenk starting material can ba Eixed in the particulat~ matrix.
~his invention is predicated in part upon the discovery that certain combinations of disaccharides and carbohydrates can be employed in aqueous admixture with a flavoring agent and, where the ratio of the disaccharide to the carbohydrate; in the aqueous admixture is controlled, the aqueous mixtures may be spray-dried ant at least 30~ flavoring agent is fixed per total particle weight with less than about
In view of the vast body of art in the area of fixed flavor compositions, to applicant's knowledge, it has , not heretofore been previously reported or known that volatile flavoring agents could be fixed in certain carbohydrate matrices in significantly large amounts without ;
detrimental amounts of flavoring agents on the particle surfaces, and it has not heretofore been known to provide a method for producing such particulate flavor compositions in an effective manner without loss of flavoring components.
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:~ Summary o the ~nvention ,~, Thls inv~ntion is directed to novel particulate flavoring m~terials and methods of producing same. The ~' parkiculate flavoring materials, according to the principles of this inven~ion, comprise a flavoring agent fixed in a particulate matrix of a disaccharide and certain ~; carbohydrate materials. It has been found that particulate ;-~
flavoring materials can be produced which contain substantial amounts of flavoring agent entrapped in the particle matrix ~; 10 on the order of at least about 30% to about 60% or more of the flavoring agent per total particle weight and wherein less than about 4~ of flavoring agent is unentrapped on the surface of the particles.
Furthermore, it has been found that a particulate flavoring composition can be prepared by formin~ an aqueous mixture of ~he flavoring agent, a disaccharide and a carbohydrate ma~eria~ and spray-drying the aqueous mixture und~r the in~luence of heak to form a particulate flavoring composition having substantial amounts of fixed flavoring , 20 agent in the matrix with only an insignificant amount of unentrapped agent on the surface of the particles. Another ! advantage o~ the method is that all ox neaxly all o~ th~
flavoring agenk starting material can ba Eixed in the particulat~ matrix.
~his invention is predicated in part upon the discovery that certain combinations of disaccharides and carbohydrates can be employed in aqueous admixture with a flavoring agent and, where the ratio of the disaccharide to the carbohydrate; in the aqueous admixture is controlled, the aqueous mixtures may be spray-dried ant at least 30~ flavoring agent is fixed per total particle weight with less than about
4% of the flavoring agent unentrapped on the surface of the .
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pa~ticles. The ratio o~ a particular disaccharide to a ~ particular carbohydrate has been found to uary somewhat, ,,, :
but neverthelecls w.ithin the scope of this invention it will b~ appreci~ted that ~here may be variances to achieve the substantial entrapment of the flavoring agent in the matrix with minimal residual agent on the particle surface.
More particularly, in one of the preferred embodiments, sucrose is employed with a carbohydrate material such as a hydrophilic colloid gum or a starch hydrolysate as the matrix composition for flavoring oil fixation. According to this embodiment, sucrose within the range of about 50 to about 95% by weight and a starch hydrolysate within the range `-of about 50 to about 5% by weight, based upon the total weight of these ingredients may be dispersed in aqueous admixture with an amount o~ flavoring oil. The 1avoring oils are contained in amounts at least about 30 to about ~0 by volume based on the total matrix and oil ingredients.
This aqueous admixture may be spray-dried under the influence of heat! e.g., warm air, using typical nozzle spray-drying appara`tus where the drying temperatures are generally of about 180F to about ~50F. ~or example, flavoring oil ~ixa-tion in sucros~,h~drolysed starch o~ at least abou-t 30~ to about 60~ by volume/woi~ht has been achievecl. Fuxthermore, &ven with such signi~icant amounts of flavoring oil fixation, surface oil on the spray-dried particles is less than about ~%~ Even more surprising, where about 50~ to about 95~
by weight of qucrose is combined with a hydrolysed starch of about 5 to about 50% by weight, at least 30~ by volume ~; flavoring oil fixation with les~ than about 2~ particle sur~ace oil is achieved. The exact mechanism for such superior entrapment with lack of residual surface oil is not known but empirical results have been obtained, As . .
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mentioned ahove~ it has been found essential tha-t the ratio o~ the sucro.se to the particular car~ohydrate be maintained within a range to achieve the advantageous results For exAmple, wher~ ~ucro~e is employed with a starch hydrolysate~
as the amount of hydrolysed starch increases about 50%, the initial amount of total oil in the particles ma~ be greater than 30~, however, the surface oil increases above 4% and this is found to be unsatisfactory. When the amount of surface oil increases above about 4%, the flavoring composition becomes susceptible to alteration by chemical change thereby deviating from t~e taste sought in the ` flavoring composition and in the food preparations containing same. Such alteration affects the entire flavoring composition Oftentimes, compositions become rancid and must be discardéd; and considerable economic loss may be incurred depending upon the volume of spoilage, On the other hand~
with the compositions o~ this invention substantial amounts of flavoring agents may be enkrapped, and stored for significant periods of time without loss or deterioration of essentail flavoring components. Also, by reason of the substantial amount of flavoring agent fixation in a particulate matrix, subs~antial savings in the manu;~acture, ~torage and shipment o~ such flavoring materials is achieved~
The advantages and objectives oP thi~ lnven-tlon can be achleved with a number of Elavoring agents.
Accordingly, the term "flavoring agent", as used herein~
encompasses any one o~ a number oE mixtures or Elavoring oils, solid~, or other liquids or essences well known as flavor enhancers. Exemplary are grape, orange, cranberry, lemon and lime oils or extracts; flavoring solids or liquids including imitation strawberry, imitation raspberry, ~-imitation cherry, imitation peach etc. Other natural or `
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syn~hetic flavoring agents can be employed~ Accordingly, it is t~ b~ un~ers~ood that these mentioned ~lavoring agents are exemplary o ~he type which may be used and are not l;rnitations on the saope o~ this invention. When the ~lavor agent is an oil or liquid, the percentages of entrapment or sùrface residue are expressed as ~ per total particle weight.
When flavoring solids are employed, these percentages are by weight, and where mixtures are employed percentage ratios of each may be determined. More broadly, therefore, the percentages expressed may be either by volume or by weight depending upon whether liquid or solid flavoring agents are employed.
Only certain matrix materials have been found to ;
provide the advantageous results and objectives o~ this invention. It is essential to employ a combination of a disaccharide, such as sucrose and lactose, and a carbohydrate material selected from a group which may be broadly classed hydrophilic colloids and starch hydrolysates~
t: Typical of hydrophilic colloids which may be used in the present invention is gum arab}c. Of the hydrolysed starches or the starch hydrolysates useful in accordance with this invention are those o~ the typ~ mention~d in tha for~going patents, namely, U.S. Patent 3,554,768 and 3,736,1~9.
Elowov~r, in contrast ~o th~ disalo~uro oE ~h~se and oth@r patents, a particular disaccharide such as sucrose has been found to provide the desired fixation with a hydrocolloid gum such as gum arabic or hydrolysed starch, or mixtures thereof, at certain rakios. When other ratios are employed, ~ either the aqueous mixture may not be particulated such as by ¦ 30 spray-drying, or substantial fixation of at least about 30%
j flavoring agent with less than about 4% surface residue cannot be achieved, or more than 25% o~ the agent is lost in ~; bm:
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~ V~S672 processing. When lactose is employed as the disacchar;.de, mixtures with hydrocolloid gum arabic where the ratios of 60~ sugar to 90% gum are employed, using similar procedures based upon experience with sucrose, the flavor fixation drops drastical].y to below 20~ and surface residue increas~s, or flavor volatiles are lost. It has also been established that a disaccharide sucrose or lactose alone, or the carbohydrate gum or hydrolysed starch alone, as the matrix material will either not permit aqueous mixtures with flavoring oils to be spray-dried under normal conditions, or if they are spray-dryable, the products will not fix significant amounts of oil at levels achieved by this invention without significant surface oil levels, and even flavor oils will be lost in processing Even further, monosaccharides have not been ~ound suitable to achieve the advantages and objectives o this invention when a-~empts are made to use these compounds alone or in combination with other carboh~drates at levels similar to those used with the disaccharides of ~his invention.
Accordingly, in this invention, the combination and ratio of the particular disaccharide to the particular carbohydrate is essential to achieve the substantial flavor entrapment with lack o~ residual surEace Elavor agen-t in the particulatc Elavoring composition. These particulate oompo~itlons and tho mcthods oE ~his inven~ion will bo fur-thcr understood, and the advantages and objectives obtained, in accordance with the following examples.
~n aqueous solution of sucrose was prepared by dissolving 3.9 lbs. of sucrose in 1,5 gal. of water. To this solution was added 2,6 lbs, of Kadex* 123-100, a starch hydrolysate prepared from tapioca starch by oxidation with * Trademark .
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~ 8S672 hydrolysation and having a Dex~rose Equivalen~ (D.E.) of about 1-2, (a product of Stein Hcill Company) and mixed well.
A 25% by weight sodium benzoate solution in an amount o~ 1 flu:id ounce was added to the ~ucrose-nlodified starch solution. rrhe sodium benzoate was added merel~ as a perservative. An orange oil in an amount of 64 fluid ounces ~density about 0.85 g/cc) was added to the resultant mixture to provide a 40% by volume per weight of ingredients -and the entire mass was mixed well to form an emulsion. The emulsion was then fed into a nozzle type spray dryer at 2500 psi. The sprayed particles were introduced into a vertical dryin~ chamber fed with heated air whose inlet temperature was about 300F and the oulet temperature was about 180F. Particles were collected at the bottom of the drylng chamber. A particulate flavoring composition was prepared upon spray-drying which was analy~ed to contain about 35% by volume orange oil Elavor/weigh~ basis (cc per 100 grams of particulate composition). This determination may be made in the case of orange oil by distillation of the oil from the resultant particles. In addition, a surface oil analysis was run by the addition of an amount of the spray-dried particles to a perchloroe-thylene solven-~ and, aftex shaking of the particLes ~or abou~ 1/2 ~o 1 minute, then ~epar~ting the solvent ;rom tho ex-tracted ~urEac~ o;Ll, ;it w~s dctermined that the surface oil was about 1~ volume/weight.
A ~aries o~ examples were performed varying the xatio o~ the ~uarose to the carbohydrate component as reported in Example 1, employing the same procedures. In this series of examples, only the amount of starch hydrolysate and sucrose was varied, respectively, from about 50%-10% by weight of starch hydrolysate to 50%-90% weight of bm:
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sucrose on a t~tal parts by weight basis for the two matrix components. In each ~xampl~ the amount of orange oil remained the same and was about 40~ by volume/weight as above ~or addi.tion to the aqueous admixture prior to spr~y-drying. Following the same spray-drying procedures, particulate flavoring compositions were obtained in the manner accordiny to Example 1 and the results are reported in the following Table I.
TABLE I
EXAMPLES -2 3 D~ 5 6 % Starch Hydrolysate 50 ~0 30 20 10 ~ Sucrose 50 60 70 80 90 , TOT~L OIL 37 35 36 36 36 SURFACE OIL 1.8 1.5 0.65 0.70.6 As demonstrated by Examples 2-6, where the amount of sucrose was present in the aqueous admixture within the range of about 50 to about 90~ by weight and the amount of hydrolysed starch was pres~nt from about 10 -to abou-t 504 by weight, the total volatilc Elavoxin~ oil conten~ o;E the partiaulate composit:Lon was in ~xaes~ o~ 30%, namely, 35-373 volume/total particle woigh~; and ~hc cn~rapped oil was about 35~ volume/weight. The surface oil content of the particulate flavoring composition was less than 2~ by volume, namely, 0.6-1.8~ volume/weight. Remarkably~ therefore, within the range of sugar from about 50-95~ to hydrolysed starch of ;
about 50-5% by weight, the unentrapped surface oil in the particulate composition was less than about 2% by volume/
weight. Accordingly, in the most preferred practice of the bm:
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with a matrix of sucrose-hydrolysed starch, the ratio of such matrix materials is on the order of about 50-95~ and 50-5~, rcspectively, On the other hand, when 60/40 or 70/30 percent~ges of hydrolysed starch to sucrose are spray-dried, higher surface oil content and less entrapped ~- :
oils are obtained. ~
These examples also demonstrate that nearly all . !
of the flavoring oil of the aqueous mixtures was fixed in the particulate matrix, e.g., 35% of the 40% charged, or in excess of 85% by volume. ~ .
When lemon flavor liquid is employed as the flavoring oil and particulate compositions were prepared in accordance with Example 1 to obtain an entrapped oil content of about 36~ with a surface oil of about 1.5~, storage of the product at 113F for 36 weeks exhibited organoleptic stability, .20 The procedure of Example 1 was followed wherein the same ingredients were employed with the same spray-drying process except 89 fluid ounces of gum solution (3.5 lbs. of gum arab:Lc per gallon o~ sol~l~ion) were subski~uted for the starch hydrolysa~e and tha additional wa~er wa~
reduc~d Erom .L.5 cJallons to 0.8 ~allon~. Upon spray-drying at the same conditions a particulate flavoring composition was obtained containing total entrapped oil and unentrapped sur~ae oll comparable to Example 1, namely, about 35~
: volume/weight total oil and 1.5~ volume/weight of surface oil.
The ingredients and procedures of Example 1 were repeated, except that a mixture of Kadex* 123-100 and gum * Trademark ~n: ' ' ,, . "
~S672 solution were substituted for the Kadex* 123-100 of Example 1. ln this example, ~5 fluid ounces of the gum arabic solution (35 lbs. of gum arabic per gallon of solution) and 1.3 lhs. of Kadex* 123-100 wcre employed. Upon spray-drying under the same conditions of Example 1, a particulate . .
.flavoring composition was obtained containing about 35 volume/weight of total flavoring oil and about 2 2% volume/
weight surface oil. .
The ingredients and procedures of Example 1 were repeated, except in this example Morrex* 1918 (a 10-12 D E
starch hydrolysate prepared from a high amylopectin-containing starch, a product of Corn Products Company) was substituted for the Kadex* 123-100 starch hydrolysate on a sim1lar parts by we.ight basis. The ratio of sucrose to modified starch in this example was about 60 to 90% by weight, .
respectively. Upon spray-drying according to the procedure of Example 1, a particulate flavoring composition was obtained with about 34~ volume/weight of total flavoring oil in the particulate matrix and about 1.25~ volume/weight of : unentrapped surace oil. Accordingly, about 33~ by volume/
weight was entrapped in the particulate matrix.
I:XAMP~ 0 Examplo 1 was repeatccl employing ~imilar procedures and ingredients, except substituting lactose for the sucrose wherein the ratio of the disacchari;de to the hydrolysed ~tarch was 60~ to 90~ by weight. Upon spray-drying, a particulate flavoring composition was obtained with about 34% volume/weight of total flavoring oil in the particulate matrix and about 3.2% volume/weight of the unentrapped surface oil.
* Trademark .;
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In c~mparison to the results obtained according to the above examples, attempts were made to employ mono-saccharid~s such as fructose or dextrose with Kadex 123-100 under ~im:ilar spra~-dryiny conditions, but aqueous mixtures o~ such monosaccharides at a similar ratio wi~h the carbohydrate (i.e. 60%/40%~ were not capable of being spray-dried `~
as in Example 1. When percentages of the monosaccharides to the carbohydrates were decreased to 30~/70% to enable spray-drying, initial flxed oil content dropped below 30%
hy volume/weight and the residual or surface oil was higher than 4% by volume, e.g., 5-6% by volume. When lactose was employed with gum arabic in a ratio of 60%/40%, respectively, the surface oil of the particulate composition was about 5% and the initial fixed oil was about 24% b~
volume/weight, also indicating a loss of about 40~ ~lavorin~
oil durin~ spray-drying. Similar resul~s were ob~ained when lactose was employed with a combination oE 20~ Kadex 123-100, 20% gum arabic and 60% lactose. Furthermore, when hydrolysed starch (Morrex 1918 or Kadex 123-100) or gum arabic is employed alone as a matrix material, flavoring oil loss or high surface oil has been observed in processing.
I~ will be appreciated tha-~ ~hc temperatures and condi~ions used in spray-drying are related to the type o~
drier and atomizer available, par~icl~ size desired and ~ha like. Typically, the inlet temperature of the drier may be about 250-450~F and the outlet temperature about 180-300F.
While ~he atomiz~r as described above was a single fluid high pressure nozzle, it may be a centrifugal dish or a two-fluid nozzle using air, steam, or inert gas as the atomizing agent. Driers themselves may be vertical or hor;.zontal.
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In view of the above detailed description and operating example.s, other modiicat.ions and embodimellts will become apparent to a person of ordinary skill in the art and such ar~ wi~hin ~he scope of this invention.
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pa~ticles. The ratio o~ a particular disaccharide to a ~ particular carbohydrate has been found to uary somewhat, ,,, :
but neverthelecls w.ithin the scope of this invention it will b~ appreci~ted that ~here may be variances to achieve the substantial entrapment of the flavoring agent in the matrix with minimal residual agent on the particle surface.
More particularly, in one of the preferred embodiments, sucrose is employed with a carbohydrate material such as a hydrophilic colloid gum or a starch hydrolysate as the matrix composition for flavoring oil fixation. According to this embodiment, sucrose within the range of about 50 to about 95% by weight and a starch hydrolysate within the range `-of about 50 to about 5% by weight, based upon the total weight of these ingredients may be dispersed in aqueous admixture with an amount o~ flavoring oil. The 1avoring oils are contained in amounts at least about 30 to about ~0 by volume based on the total matrix and oil ingredients.
This aqueous admixture may be spray-dried under the influence of heat! e.g., warm air, using typical nozzle spray-drying appara`tus where the drying temperatures are generally of about 180F to about ~50F. ~or example, flavoring oil ~ixa-tion in sucros~,h~drolysed starch o~ at least abou-t 30~ to about 60~ by volume/woi~ht has been achievecl. Fuxthermore, &ven with such signi~icant amounts of flavoring oil fixation, surface oil on the spray-dried particles is less than about ~%~ Even more surprising, where about 50~ to about 95~
by weight of qucrose is combined with a hydrolysed starch of about 5 to about 50% by weight, at least 30~ by volume ~; flavoring oil fixation with les~ than about 2~ particle sur~ace oil is achieved. The exact mechanism for such superior entrapment with lack of residual surface oil is not known but empirical results have been obtained, As . .
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~V~S67Z
mentioned ahove~ it has been found essential tha-t the ratio o~ the sucro.se to the particular car~ohydrate be maintained within a range to achieve the advantageous results For exAmple, wher~ ~ucro~e is employed with a starch hydrolysate~
as the amount of hydrolysed starch increases about 50%, the initial amount of total oil in the particles ma~ be greater than 30~, however, the surface oil increases above 4% and this is found to be unsatisfactory. When the amount of surface oil increases above about 4%, the flavoring composition becomes susceptible to alteration by chemical change thereby deviating from t~e taste sought in the ` flavoring composition and in the food preparations containing same. Such alteration affects the entire flavoring composition Oftentimes, compositions become rancid and must be discardéd; and considerable economic loss may be incurred depending upon the volume of spoilage, On the other hand~
with the compositions o~ this invention substantial amounts of flavoring agents may be enkrapped, and stored for significant periods of time without loss or deterioration of essentail flavoring components. Also, by reason of the substantial amount of flavoring agent fixation in a particulate matrix, subs~antial savings in the manu;~acture, ~torage and shipment o~ such flavoring materials is achieved~
The advantages and objectives oP thi~ lnven-tlon can be achleved with a number of Elavoring agents.
Accordingly, the term "flavoring agent", as used herein~
encompasses any one o~ a number oE mixtures or Elavoring oils, solid~, or other liquids or essences well known as flavor enhancers. Exemplary are grape, orange, cranberry, lemon and lime oils or extracts; flavoring solids or liquids including imitation strawberry, imitation raspberry, ~-imitation cherry, imitation peach etc. Other natural or `
~ ' bm:
- ~ V ~ S 6 7 Z
syn~hetic flavoring agents can be employed~ Accordingly, it is t~ b~ un~ers~ood that these mentioned ~lavoring agents are exemplary o ~he type which may be used and are not l;rnitations on the saope o~ this invention. When the ~lavor agent is an oil or liquid, the percentages of entrapment or sùrface residue are expressed as ~ per total particle weight.
When flavoring solids are employed, these percentages are by weight, and where mixtures are employed percentage ratios of each may be determined. More broadly, therefore, the percentages expressed may be either by volume or by weight depending upon whether liquid or solid flavoring agents are employed.
Only certain matrix materials have been found to ;
provide the advantageous results and objectives o~ this invention. It is essential to employ a combination of a disaccharide, such as sucrose and lactose, and a carbohydrate material selected from a group which may be broadly classed hydrophilic colloids and starch hydrolysates~
t: Typical of hydrophilic colloids which may be used in the present invention is gum arab}c. Of the hydrolysed starches or the starch hydrolysates useful in accordance with this invention are those o~ the typ~ mention~d in tha for~going patents, namely, U.S. Patent 3,554,768 and 3,736,1~9.
Elowov~r, in contrast ~o th~ disalo~uro oE ~h~se and oth@r patents, a particular disaccharide such as sucrose has been found to provide the desired fixation with a hydrocolloid gum such as gum arabic or hydrolysed starch, or mixtures thereof, at certain rakios. When other ratios are employed, ~ either the aqueous mixture may not be particulated such as by ¦ 30 spray-drying, or substantial fixation of at least about 30%
j flavoring agent with less than about 4% surface residue cannot be achieved, or more than 25% o~ the agent is lost in ~; bm:
~' , , ;:
, :, . .. . .
~ V~S672 processing. When lactose is employed as the disacchar;.de, mixtures with hydrocolloid gum arabic where the ratios of 60~ sugar to 90% gum are employed, using similar procedures based upon experience with sucrose, the flavor fixation drops drastical].y to below 20~ and surface residue increas~s, or flavor volatiles are lost. It has also been established that a disaccharide sucrose or lactose alone, or the carbohydrate gum or hydrolysed starch alone, as the matrix material will either not permit aqueous mixtures with flavoring oils to be spray-dried under normal conditions, or if they are spray-dryable, the products will not fix significant amounts of oil at levels achieved by this invention without significant surface oil levels, and even flavor oils will be lost in processing Even further, monosaccharides have not been ~ound suitable to achieve the advantages and objectives o this invention when a-~empts are made to use these compounds alone or in combination with other carboh~drates at levels similar to those used with the disaccharides of ~his invention.
Accordingly, in this invention, the combination and ratio of the particular disaccharide to the particular carbohydrate is essential to achieve the substantial flavor entrapment with lack o~ residual surEace Elavor agen-t in the particulatc Elavoring composition. These particulate oompo~itlons and tho mcthods oE ~his inven~ion will bo fur-thcr understood, and the advantages and objectives obtained, in accordance with the following examples.
~n aqueous solution of sucrose was prepared by dissolving 3.9 lbs. of sucrose in 1,5 gal. of water. To this solution was added 2,6 lbs, of Kadex* 123-100, a starch hydrolysate prepared from tapioca starch by oxidation with * Trademark .
-8- . :
bm:
~ 8S672 hydrolysation and having a Dex~rose Equivalen~ (D.E.) of about 1-2, (a product of Stein Hcill Company) and mixed well.
A 25% by weight sodium benzoate solution in an amount o~ 1 flu:id ounce was added to the ~ucrose-nlodified starch solution. rrhe sodium benzoate was added merel~ as a perservative. An orange oil in an amount of 64 fluid ounces ~density about 0.85 g/cc) was added to the resultant mixture to provide a 40% by volume per weight of ingredients -and the entire mass was mixed well to form an emulsion. The emulsion was then fed into a nozzle type spray dryer at 2500 psi. The sprayed particles were introduced into a vertical dryin~ chamber fed with heated air whose inlet temperature was about 300F and the oulet temperature was about 180F. Particles were collected at the bottom of the drylng chamber. A particulate flavoring composition was prepared upon spray-drying which was analy~ed to contain about 35% by volume orange oil Elavor/weigh~ basis (cc per 100 grams of particulate composition). This determination may be made in the case of orange oil by distillation of the oil from the resultant particles. In addition, a surface oil analysis was run by the addition of an amount of the spray-dried particles to a perchloroe-thylene solven-~ and, aftex shaking of the particLes ~or abou~ 1/2 ~o 1 minute, then ~epar~ting the solvent ;rom tho ex-tracted ~urEac~ o;Ll, ;it w~s dctermined that the surface oil was about 1~ volume/weight.
A ~aries o~ examples were performed varying the xatio o~ the ~uarose to the carbohydrate component as reported in Example 1, employing the same procedures. In this series of examples, only the amount of starch hydrolysate and sucrose was varied, respectively, from about 50%-10% by weight of starch hydrolysate to 50%-90% weight of bm:
1~151S67Z
sucrose on a t~tal parts by weight basis for the two matrix components. In each ~xampl~ the amount of orange oil remained the same and was about 40~ by volume/weight as above ~or addi.tion to the aqueous admixture prior to spr~y-drying. Following the same spray-drying procedures, particulate flavoring compositions were obtained in the manner accordiny to Example 1 and the results are reported in the following Table I.
TABLE I
EXAMPLES -2 3 D~ 5 6 % Starch Hydrolysate 50 ~0 30 20 10 ~ Sucrose 50 60 70 80 90 , TOT~L OIL 37 35 36 36 36 SURFACE OIL 1.8 1.5 0.65 0.70.6 As demonstrated by Examples 2-6, where the amount of sucrose was present in the aqueous admixture within the range of about 50 to about 90~ by weight and the amount of hydrolysed starch was pres~nt from about 10 -to abou-t 504 by weight, the total volatilc Elavoxin~ oil conten~ o;E the partiaulate composit:Lon was in ~xaes~ o~ 30%, namely, 35-373 volume/total particle woigh~; and ~hc cn~rapped oil was about 35~ volume/weight. The surface oil content of the particulate flavoring composition was less than 2~ by volume, namely, 0.6-1.8~ volume/weight. Remarkably~ therefore, within the range of sugar from about 50-95~ to hydrolysed starch of ;
about 50-5% by weight, the unentrapped surface oil in the particulate composition was less than about 2% by volume/
weight. Accordingly, in the most preferred practice of the bm:
1~)8S672 inventlon where a signi~icantly high percent of ~lavor oil entrapment i5 desired, i.e,, within the range o~ 30-60~
with a matrix of sucrose-hydrolysed starch, the ratio of such matrix materials is on the order of about 50-95~ and 50-5~, rcspectively, On the other hand, when 60/40 or 70/30 percent~ges of hydrolysed starch to sucrose are spray-dried, higher surface oil content and less entrapped ~- :
oils are obtained. ~
These examples also demonstrate that nearly all . !
of the flavoring oil of the aqueous mixtures was fixed in the particulate matrix, e.g., 35% of the 40% charged, or in excess of 85% by volume. ~ .
When lemon flavor liquid is employed as the flavoring oil and particulate compositions were prepared in accordance with Example 1 to obtain an entrapped oil content of about 36~ with a surface oil of about 1.5~, storage of the product at 113F for 36 weeks exhibited organoleptic stability, .20 The procedure of Example 1 was followed wherein the same ingredients were employed with the same spray-drying process except 89 fluid ounces of gum solution (3.5 lbs. of gum arab:Lc per gallon o~ sol~l~ion) were subski~uted for the starch hydrolysa~e and tha additional wa~er wa~
reduc~d Erom .L.5 cJallons to 0.8 ~allon~. Upon spray-drying at the same conditions a particulate flavoring composition was obtained containing total entrapped oil and unentrapped sur~ae oll comparable to Example 1, namely, about 35~
: volume/weight total oil and 1.5~ volume/weight of surface oil.
The ingredients and procedures of Example 1 were repeated, except that a mixture of Kadex* 123-100 and gum * Trademark ~n: ' ' ,, . "
~S672 solution were substituted for the Kadex* 123-100 of Example 1. ln this example, ~5 fluid ounces of the gum arabic solution (35 lbs. of gum arabic per gallon of solution) and 1.3 lhs. of Kadex* 123-100 wcre employed. Upon spray-drying under the same conditions of Example 1, a particulate . .
.flavoring composition was obtained containing about 35 volume/weight of total flavoring oil and about 2 2% volume/
weight surface oil. .
The ingredients and procedures of Example 1 were repeated, except in this example Morrex* 1918 (a 10-12 D E
starch hydrolysate prepared from a high amylopectin-containing starch, a product of Corn Products Company) was substituted for the Kadex* 123-100 starch hydrolysate on a sim1lar parts by we.ight basis. The ratio of sucrose to modified starch in this example was about 60 to 90% by weight, .
respectively. Upon spray-drying according to the procedure of Example 1, a particulate flavoring composition was obtained with about 34~ volume/weight of total flavoring oil in the particulate matrix and about 1.25~ volume/weight of : unentrapped surace oil. Accordingly, about 33~ by volume/
weight was entrapped in the particulate matrix.
I:XAMP~ 0 Examplo 1 was repeatccl employing ~imilar procedures and ingredients, except substituting lactose for the sucrose wherein the ratio of the disacchari;de to the hydrolysed ~tarch was 60~ to 90~ by weight. Upon spray-drying, a particulate flavoring composition was obtained with about 34% volume/weight of total flavoring oil in the particulate matrix and about 3.2% volume/weight of the unentrapped surface oil.
* Trademark .;
bm:
~L~85~7Z
In c~mparison to the results obtained according to the above examples, attempts were made to employ mono-saccharid~s such as fructose or dextrose with Kadex 123-100 under ~im:ilar spra~-dryiny conditions, but aqueous mixtures o~ such monosaccharides at a similar ratio wi~h the carbohydrate (i.e. 60%/40%~ were not capable of being spray-dried `~
as in Example 1. When percentages of the monosaccharides to the carbohydrates were decreased to 30~/70% to enable spray-drying, initial flxed oil content dropped below 30%
hy volume/weight and the residual or surface oil was higher than 4% by volume, e.g., 5-6% by volume. When lactose was employed with gum arabic in a ratio of 60%/40%, respectively, the surface oil of the particulate composition was about 5% and the initial fixed oil was about 24% b~
volume/weight, also indicating a loss of about 40~ ~lavorin~
oil durin~ spray-drying. Similar resul~s were ob~ained when lactose was employed with a combination oE 20~ Kadex 123-100, 20% gum arabic and 60% lactose. Furthermore, when hydrolysed starch (Morrex 1918 or Kadex 123-100) or gum arabic is employed alone as a matrix material, flavoring oil loss or high surface oil has been observed in processing.
I~ will be appreciated tha-~ ~hc temperatures and condi~ions used in spray-drying are related to the type o~
drier and atomizer available, par~icl~ size desired and ~ha like. Typically, the inlet temperature of the drier may be about 250-450~F and the outlet temperature about 180-300F.
While ~he atomiz~r as described above was a single fluid high pressure nozzle, it may be a centrifugal dish or a two-fluid nozzle using air, steam, or inert gas as the atomizing agent. Driers themselves may be vertical or hor;.zontal.
; bm:
.. .
In view of the above detailed description and operating example.s, other modiicat.ions and embodimellts will become apparent to a person of ordinary skill in the art and such ar~ wi~hin ~he scope of this invention.
bm:
. I
Claims (17)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A particulate flavoring material comprising a flavoring agent fixed in a particulate matrix, said particulate matrix containing a disaccharide and a carbohydrate selected from the group consisting of hydrophilic colloids and starch hydrolysates wherein the ratio of the disaccharide to the carbohydrate is such that at least about 30% flavoring agent per total particulate material is entrapped in the matrix and less than about 4%
flavoring agent per total particulate material is unentrapped on the surface of said particulate matrix.
flavoring agent per total particulate material is unentrapped on the surface of said particulate matrix.
2. The flavoring material of Claim 1 wherein said disaccharide is sucrose and said carbohydrate is starch hydrolysate and wherein the ratio of the sucrose to the starch is on the order of about 50-95% by weight sucrose to about 5-50% by weight starch.
3. The particulate flavoring material of Claim 1 wherein said agent is an oil, the disaccharide is sucrose and the carbohydrate is starch hydrolysate and wherein the ratio of the sucrose to the starch is on the order of about 50-95%
by weight sucrose to about 5-50% by weight starch and the unentrapped surface oil is less than about 2% by volume flavoring oil per total particulate material weight.
by weight sucrose to about 5-50% by weight starch and the unentrapped surface oil is less than about 2% by volume flavoring oil per total particulate material weight.
4. The particulate flavoring material of Claim 1 wherein the amount of flavoring agent entrapped is with the range of about 30 to about 60% per total particulate flavoring material.
5. The particulate flavoring material of Claim 3 wherein the amount of flavoring oil entrapped is within the range of about 30 to about 60% by volume of flavoring oil per total particulate flavoring material weight.
6. The particulate flavoring material of Claim 1 wherein said disaccharide is lactose and said carbohydrate is starch hydrolysate.
7. The particulate flavoring material of Claim 6 wherein the ratio of the lactose to the starch hydrolysate is on the order of about 60% lactose to about 40% starch.
8. A particulate flavoring material of Claim 1 wherein said disaccharide is sucrose and said hydrophilic colloid is gum arabic.
9. A method for preparing a particulate flavoring material comprising forming an aqueous mixture of a flavoring agent, a disaccharide and a carbohydrate selected from the group consisting of hydrophilic colloids and starch hydrolysates, and spray-drying the aqueous mixture under the influence of heat to form the particulate flavoring composition wherein the ratio of the disaccharide to the carbohydrate in said aqueous mixture is such that the mixture is capable of being spray-dried and wherein at least 30%
flavoring agent per total particulate material is entrapped in the matrix and less than about 4% flavoring agent per total particulate material is unentrapped on the surface of said particulate matrix.
flavoring agent per total particulate material is entrapped in the matrix and less than about 4% flavoring agent per total particulate material is unentrapped on the surface of said particulate matrix.
10. The method of Claim 9 wherein said disaccharide is sucrose and said carbohydrate is starch hydrolysate and wherein the ratio of the sucrose to the starch in said aqueous mixture is on the order of about 50-95% by weight sucrose to about 5-50% by weight starch.
11. The method of Claim 9 wherein said agent is an oil, the disaccharide is sucrose and said carbohydrate is starch hydrolysate and wherein the ratio of the sucrose to the starch is on the order of about 50-95% by weight sucrose to about 5-50% by weight starch in said aqeuous mixture and the unentrapped surface oil is less than about 2% by volume flavoring oil per total particulate material weight.
12. The method of Claim 9 wherein the amount of flavoring agent in said aqueous mixture is within the range of about 30 to about 60% of the flavoring agent per total disaccharide, carbohydrate and flavoring agent weight.
13. The method of Claim 9 wherein said disaccharide is lactose and said carbohydrate is starch hydrolysate.
14. The method of Claim 9 wherein said disaccharide is sucrose and said hydrophilic colloid is a hydrophilic gum.
15. The method of Claim 9 wherein the spray-drying is conducted under the influence of heat at temperatures on the order of about 180° to about 450°F.
16. The method of Claim 9 wherein at least about 80%
of said flavoring agent in said aqueous mixture is entrapped in said particulate matrix.
of said flavoring agent in said aqueous mixture is entrapped in said particulate matrix.
17. A method for preparing a particulate flavoring material comprising forming an aqueous mixture of a flavoring oil in an amount of about 30 to about 60% by volume, sucrose and a carbohydrate selected from the group consisting of starch hydrolysate and gum arabic, wherein the ratio of the sucrose to the carbohydrate in said aqueous mixture is on the order of about 50-95% by weight to about 5-50% by weight, respectively, and spray-drying the aqueous mixture under the influence of heat to form the particulate flavoring composition wherein at least 30% by volume flavoring oil per total particulate material weight is entrapped in the matrix and less than about 2% flavoring oil per total particulate material weight is unentrapped on the surface of said particulate matrix and at least about 80% of said flavoring oil of said aqueous mixture is entrapped in said particulate matrix.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64018975A | 1975-12-12 | 1975-12-12 | |
| US640,189 | 1975-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085672A true CA1085672A (en) | 1980-09-16 |
Family
ID=24567212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,623A Expired CA1085672A (en) | 1975-12-12 | 1976-12-10 | Particulate flavoring materials and method of producing same |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5941383B2 (en) |
| AR (1) | AR214868A1 (en) |
| AU (1) | AU501025B2 (en) |
| BE (1) | BE849319A (en) |
| BR (1) | BR7608358A (en) |
| CA (1) | CA1085672A (en) |
| CH (1) | CH618851A5 (en) |
| DE (1) | DE2656418C2 (en) |
| ES (1) | ES454147A1 (en) |
| FR (1) | FR2334309A1 (en) |
| GB (1) | GB1550008A (en) |
| IL (1) | IL51064A (en) |
| IN (1) | IN145614B (en) |
| IT (1) | IT1067974B (en) |
| MX (1) | MX4058E (en) |
| NL (1) | NL7613760A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT364688B (en) * | 1979-07-19 | 1981-11-10 | Gergely Gerhard | METHOD FOR PRODUCING A FLAVOR PRODUCT |
| JPS60192568A (en) * | 1984-03-13 | 1985-10-01 | Inahata Sangyo Kk | Method of enriching of fragrance of processed food, and carrier composition to be used therefor |
| JPS6147143A (en) * | 1984-08-15 | 1986-03-07 | Morinaga Milk Ind Co Ltd | Instant creaming powder enriched with flavor, or such |
| US5236734A (en) * | 1987-04-20 | 1993-08-17 | Fuisz Technologies Ltd. | Method of preparing a proteinaceous food product containing a melt spun oleaginous matrix |
| JP2007254339A (en) | 2006-03-22 | 2007-10-04 | Takasago Internatl Corp | Lock-in type powder |
| CN104922071A (en) | 2010-04-09 | 2015-09-23 | 帕西拉制药有限公司 | Method for formulating large diameter synthetic membrane vesicles |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2919989A (en) * | 1958-03-05 | 1960-01-05 | Thomas H Schultz | Solid flavoring composition and method of producing the same |
| US2929723A (en) * | 1958-12-22 | 1960-03-22 | Thomas H Schultz | Compositions containing flavoring agent and lecithin in a sugar base and process of making the same |
| US3183099A (en) * | 1962-11-09 | 1965-05-11 | Thomas H Schultz | Preparation of flavor compositions |
| DE2051729C3 (en) * | 1970-10-21 | 1975-01-30 | Maizena Gmbh, 2000 Hamburg | Dry product made from wine |
-
1976
- 1976-12-07 IN IN2168/CAL/76A patent/IN145614B/en unknown
- 1976-12-07 IL IL51064A patent/IL51064A/en unknown
- 1976-12-09 AU AU20410/76A patent/AU501025B2/en not_active Expired
- 1976-12-10 NL NL7613760A patent/NL7613760A/en not_active Application Discontinuation
- 1976-12-10 ES ES454147A patent/ES454147A1/en not_active Expired
- 1976-12-10 GB GB51707/76A patent/GB1550008A/en not_active Expired
- 1976-12-10 IT IT30301/76A patent/IT1067974B/en active
- 1976-12-10 CA CA267,623A patent/CA1085672A/en not_active Expired
- 1976-12-10 FR FR7637319A patent/FR2334309A1/en active Granted
- 1976-12-10 AR AR265807A patent/AR214868A1/en active
- 1976-12-10 BE BE173189A patent/BE849319A/en not_active IP Right Cessation
- 1976-12-10 CH CH1560776A patent/CH618851A5/en not_active IP Right Cessation
- 1976-12-13 MX MX765222U patent/MX4058E/en unknown
- 1976-12-13 JP JP51149648A patent/JPS5941383B2/en not_active Expired
- 1976-12-13 BR BR7608358A patent/BR7608358A/en unknown
- 1976-12-13 DE DE2656418A patent/DE2656418C2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH618851A5 (en) | 1980-08-29 |
| ES454147A1 (en) | 1977-12-01 |
| AR214868A1 (en) | 1979-08-15 |
| IN145614B (en) | 1979-04-21 |
| IT1067974B (en) | 1985-03-21 |
| GB1550008A (en) | 1979-08-08 |
| IL51064A (en) | 1979-11-30 |
| FR2334309B1 (en) | 1983-05-20 |
| MX4058E (en) | 1981-11-27 |
| FR2334309A1 (en) | 1977-07-08 |
| BR7608358A (en) | 1977-12-06 |
| JPS5294452A (en) | 1977-08-09 |
| AU2041076A (en) | 1978-06-15 |
| JPS5941383B2 (en) | 1984-10-06 |
| DE2656418C2 (en) | 1983-09-08 |
| NL7613760A (en) | 1977-06-14 |
| IL51064A0 (en) | 1977-02-28 |
| BE849319A (en) | 1977-06-10 |
| DE2656418A1 (en) | 1977-11-10 |
| AU501025B2 (en) | 1979-06-07 |
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