WO1995017828A1 - Chewing-gum contenant de l'aspartame stabilise par les beta-glucanes - Google Patents
Chewing-gum contenant de l'aspartame stabilise par les beta-glucanes Download PDFInfo
- Publication number
- WO1995017828A1 WO1995017828A1 PCT/US1993/012671 US9312671W WO9517828A1 WO 1995017828 A1 WO1995017828 A1 WO 1995017828A1 US 9312671 W US9312671 W US 9312671W WO 9517828 A1 WO9517828 A1 WO 9517828A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chewing gum
- aspartame
- weight
- moisture
- beta glucans
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/14—Chewing gum characterised by the composition containing organic or inorganic compounds containing peptides or proteins
Definitions
- the present invention relates to a method of stabilizing aspartame (APM) , when aspartame is used in chewing gum.
- the invention also relates to a stabilized chewing gum which contains aspartame.
- APM aspartame
- sweetened chewing gum products are susceptible to decomposition and/or reaction of the APM under certain conditions, causing loss of sweetness and undesirable off-flavors.
- the conditions that contribute to the decomposition and/or reaction of APM include, but are not limited to, exposure to heat or moisture, a neutral or alkaline pH, and the presence of aldehyde- containing flavoring agents. Under these conditions, APM can hydrolyze to the dipeptide aspartylphenylanaline (AP) , or decompose to diketopiperazine (DKP) , or react with aldehydes. AP and DKP can decompose further over time to their individual amino acid components.
- AP dipeptide aspartylphenylanaline
- DKP diketopiperazine
- APM has relatively good stability at a pH between about 3 and 5, with optimal stability occurring at about pH 4.0-4.3.
- some chewing components, especially gum bases containing calcium carbonate filler typically cause chewing gum to have pH's above that range.
- U.S. Patent 4,246,286 discloses the stabilization of APM in a chewing gum composition, by adjusting the chewing gum pH to between 5.0 and 7.0. This is accomplished by eliminating calcium carbonate filler from the gum. Also, citric acid or another non-toxic organic acid is employed as an acidifying agent.
- Japanese Publication Sho 61-212255 discloses a sweetener composition containing APM, fructose and small amounts of organic acid and organic acid salts.
- the organic acid is selected from citric acid, tartaric acid, malic acid, fumaric acid and adipic acid.
- U.S. Patent 4,087,557 issued to Bakal et al., discloses the entrapping of artificial sweeteners other than APM in an ester gum, in order to reduce or delay the initial sweetness impact of the artificial sweetener.
- the reference discloses a chewing gum in which the calcium carbonate in the base is replaced with microcrystalline cellulose powder.
- U.S. Patent 4,064,274 issued to Mackay, discloses the use of a non-basic filler such as magnesium silicate. A fruit acid is added to the gum to bring the pH to below 4.0.
- U.S. Patent 4,122,195, issued to Bahoshy et al. and U.S. Patent 4,139,639, issued to Bahoshy, disclose the encapsulation of APM to improve its stability.
- U.S. Patent 4,085,277 issued to Mackay et al. , discloses a chewing gum in which a finely divided sweetening agent and a finely divided food acid are dispersed in the gum base portion thereof.
- U.S. Patent 3,868,472 issued to Berg et al. , discloses the co-grinding of APM with an acid, in the presence of an organic solvent in which the APM is insoluble.
- U.S. Patent 4,792,453 issued to Reed et al., discloses a sugarless hard coated chewing gum having a chewing gum center prepared by mixing calcium carbonate, glycerine, and an aqueous sorbitol solution, and later adding an encapsulated high intensity sweetener.
- European Patent Application 0 272 220 and U.S. Patent 4,824,681 disclose the encapsulation of APM in a coating material comprising a hydrophobic polymer and a hydrophobic plasticizer.
- An acidifying agent can be included in the coating material to extend the shelf life of the APM.
- Japan Patent Disclosure Nos. Sho 83-198250, Sho 83-193655 and Sho 87-25014 all disclose the dispersion and encapsulation of APM in hydrogenated starch hydrolysates and/or hydrogenated maltose syrup.
- microcrystalline cellulose powder is used instead of calcium carbonate or talc.
- a combination of sodium citrate and citric, malic or tartaric acid is also used in the encapsulating agent in order to maintain a pH of 4.3 ⁇ 1.0.
- vegetable gum is also included in the sweetener ingredient. In all of these three references, the ingredients are first dissolved and mixed in water, and then dried and powdered.
- European Patent Application 0 302 024 discloses chewing gum having APM in a first portion, an aldehyde flavoring agent in a second portion and a barrier film in between the first and second portions.
- European Patent Application 0 302 023 discloses a similar chewing gum except that the first portion may also contain an organic acid to help stabilize the APM.
- beta glucans in chewing gum is also suggested in the prior art, but for purposes other than the stabilization of APM.
- U.S. Patent 4,871,571, issued to Jensen et al. suggests using hydrolyzed beta glucans in nineteen different food and confectionery items, one of which is chewing gum, as a bulking agent serving as a nutrient or stimulant.
- the reference further discloses the bulking agent used with aspartame in soft drinks and ice cream, but not in chewing gum.
- Japanese Patent Disclosure 1992- 148661 by Gantaro et al. discloses using enzyme reaction products of beta-gluco-oligosaccharides in a wide variety of foods and confectionery items including chewing gum.
- the present invention includes a method of stabilizing aspartame in chewing gum, and a stabilized chewing gum product made according to the method.
- Beta glucan is a low calorie, non-sugar bulking agent that is also low in sweetness.
- Aspartame is used to sweeten the chewing gum composition and beta glucan is used in an effective amount to stabilize the aspartame.
- the aspartame should be present at about 0.001-4.00% by weight of the chewing gum.
- the beta glucan should be present at about 2.5-50% by weight of the chewing gum.
- the beta glucan may replace some or all of the bulk sweetener (for example, sucrose and syrup) that might otherwise be present in a conventional chewing gum.
- the amount of aspartame required can be significantly reduced from the level needed to provide similar sweetness if the beta glucan were not used. This can result in a notable cost savings because the aspartame, though used at low levels, is quite expensive. This can also result in a much longer shelf life for the aspartame-containing chewing gum.
- FIG. 1 shows the lower decomposition of APM over time in high moisture gums containing lycasin, resulting when beta glucans are added to stabilize the APM.
- FIG. 2 shows the lower decomposition of APM over time in high moisture gums containing liquid sorbitol, resulting when beta glucans are added to stabilize the APM.
- FIGS. 3 and 4 show the lower decomposition of APM over time in intermediate and low moisture gums containing liquid sorbitol, resulting when beta glucans are added to stabilize the APM.
- Beta glucans are unbranched polysaccharides composed of (1-4) and (1-3) linked B-D-glucopyranosyl units. Beta glucans are found naturally in oats, barley, ryegrass, bambou, mung bean, numerous lichens and a variety of different grasses. Typical beta- glucans are mixtures of the (1-4) and (1-3) linkages described above, in various proportions.
- One commercially available beta glucan can be obtained from the R.I.T.A. Corporation, P.O. Box 585, Woodstock, IL 60098, under the name Ritavena 5.
- beta glucans are low in calories, low in sweetness and sugarless. Chewing gum products containing beta glucans and aspartame, and methods of making such chewing gum products, have been invented. Aspartame is used to sweeten the gum composition and beta glucan(s) are provided in an effective amount to stabilize the aspartame such that, after eight weeks of storage at 85°F, at least 5% less aspartame decomposes than would have decomposed if the beta glucan(s) were not included.
- the beta glucan(s) are used in sufficient quantity that, after eight weeks of storage at 85°F, at least 15% less aspartame decomposes than would have decomposed if the beta glucans were not included.
- the aspartame decomposition is reduced by at least 25% under these conditions. In a highly preferred embodiment, the aspartame decomposition is reduced by anywhere from about 33 to about 60 percent, after eight weeks of storage at 85°F.
- beta glucan(s) can be added to the chewing gum in the form of a powder or a liquid.
- beta glucan should be present at about 2.5-50% by weight of the chewing gum.
- beta glucan is present at about 5-35% by weight of the chewing gum, most preferably at about 10-20% by weight of the chewing gum.
- the amount of aspartame required to maintain a desired level of sweetness may be about 10-50% lower than the amount needed if beta glucan were absent.
- the amount of aspartame should be about 0.001-4.00% by weight of the chewing gum, preferably about 0.005-2.50% by weight of the chewing gum, most preferably about 0.01-0.90% by weight of the chewing gum.
- the invention is useful in stabilizing aspartame in high, intermediate or low moisture- containing gums, and is particularly useful for high moisture-containing gums wherein aspartame tends to be less stable.
- a high moisture-containing gum is defined as a chewing gum which contains more than 3.0% by weight moisture.
- An intermediate moisture-containing gum contains 2.0-3.0% by weight moisture.
- a low moisture-containing gum contains less than 2.0% by weight moisture.
- the invention is useful regardless of whether liquid sorbitol, hydrogenated starch hydrolysates (for example, lycasin) or some other humectant is used to provide the moisture.
- hydrogenated starch hydrolysates is the presently preferred humectant because aspartame appears to have exceptional stability in the presence of lycasin and an effective amount of beta glucan. Lycasin alone helps stabilize aspartame, as described in U.S. Patent No. 4,738,854.
- the technique of the invention can be used by itself or in combination with various known techniques for enhancing aspartame stability.
- the aspartame may be unencapsulated or encapsulated.
- the beta glucans are expected to provide further enhanced stability.
- a chewing gum composition generally includes a water soluble bulk portion, a water insoluble chewing gum base portion, and one or more flavoring agents.
- the water soluble portion dissipates over a period of time during chewing.
- the gum base portion is retained in the mouth throughout the chewing process.
- the insoluble gum base generally includes elastomers, resins, fats, oils, waxes, softeners and inorganic fillers.
- the elastomers may include polyisobutylene, isobutylene-isoprene copolymer, styrene butadiene rubber and natural latexes such as chicle.
- the resins may include polyvinyl acetate and terpene resins. Low molecular weight polyvinyl acetate is a preferred resin.
- Fats and oils may include animal fats such as lard and tallow, vegetable oils such as soybean and cottonseed oils, hydrogenated and partially hydrogenated vegetable oils, and cocoa butter.
- waxes include petroleum waxes such as paraffin and microcrystalline wax, natural waxes such as beeswax, candellia, carnauba and polyethylene wax.
- the present invention contemplates the use of any commercially acceptable chewing gum base.
- the gum base typically also includes a filler component such as calcium carbonate, magnesium carbonate, talc, dicalcium phosphate and the like; softeners, including glycerol monostearate and glycerol triacetate; and optional ingredients such as antioxidants, colors and emulsifiers.
- the gum base constitutes between 5-95% by weight of the chewing gum composition, more typically 10-50% by weight of the chewing gum, and most commonly 20-30% by weight of the chewing gum.
- the water soluble portion of the chewing gum may include softeners, bulk sweeteners, high intensity sweeteners, flavoring agents and combinations thereof.
- Softeners are added to the chewing gum in order to optimize the chewability and mouth feel of the gum.
- the softeners which are also known as plasticizers or plasticizing agents, generally constitute between about 0.5-15% by weight of the chewing gum.
- the softeners may include glycerin, lecithin, and combinations thereof.
- Aqueous sweetener solutions such as those containing sorbitol, hydrogenated starch hydrolysates, corn syrup and combinations thereof, may also be used as softeners and binding agents in chewing gum.
- Bulk sweeteners constitute between 5-95% by weight of the chewing gum, more typically 20-80% by weight of the chewing gum and most commonly 30-60% by weight of the chewing gum.
- bulk sweeteners may include both sugar and sugarless sweeteners and components.
- Sugar sweeteners may include saccharide containing components including but not limited to sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup solids, and the like, alone or in combination.
- Sugarless sweeteners include components with sweetening characteristics but are devoid of the commonly known sugars.
- Sugarless sweeteners include but are not limited to sugar alcohols such as sorbitol, mannitol, xylitol, hydrogenated starch hydrolysates, maltitol, and the like, alone or in combination.
- High intensity sweeteners may also be present in addition to the aspartame used as described above. When additional, high intensity sweeteners are used, the total amount of high intensity sweeteners should constitute between 0.003-5% by weight of the chewing gum, preferably between 0.01-1% by weight of the chewing gum. Typically, high intensity sweeteners are at least 20 times sweeter than sucrose. In addition to aspartame, these may include but are not limited to sucralose, salts of acesulfame, alitame, saccharin and its salts, cyclamic acid and its salts, glycyrrhizin, dihydrochalcones, thaumatin, monellin, and the like, alone or in combination.
- Combinations of sugar and/or sugarless sweeteners may be used in chewing gum.
- the sweetener may also function in the chewing gum in whole or in part as a water soluble bulking agent. Additionally, the softener may provide additional sweetness such as with aqueous sugar or alditol solutions.
- Flavor should generally be present in the chewing gum in an amount within the range of about 0.1-15% by weight of the chewing gum, preferably between about 0.2-5% by weight of the chewing gum, most preferably between about 0.5-3% by weight of the chewing gum.
- Flavoring agents may include essential oils, synthetic flavors or mixtures thereof including but not limited to oils derived from plants and fruits such as citrus oils, fruit essences, peppermint oil, spearmint oil, other mint oils, clove oil, oil of wintergreen, anise and the like.
- Artificial flavoring agents and components may also be used in the flavor ingredient of the invention. Natural and artificial flavoring agents may be combined in any sensorially acceptable fashion.
- Chewing gum is generally manufactured by sequentially adding the various chewing gum ingredients to any commercially available mixer known in the art. After the ingredients have been thoroughly mixed, the gum mass is discharged from the mixer and shaped into the desired form such as by rolling into sheets, scoring and cutting into sticks. Generally, the ingredients are mixed by first melting the gum base and adding it to the running mixer. The gum base may alternatively be melted in the mixer. Color and emulsifiers can be added at this time.
- a softener such as glycerin can be added next along with syrup and part of the bulk portion. Further parts of the bulk portion may then be added to the mixer. Flavoring agents are typically added with the final part of the bulk portion. The entire mixing process typically takes from five to fifteen minutes, although longer mixing times are sometimes required. Those skilled in the art will recognize that variations of this mixing procedure, or other mixing procedures, may be followed.
- Example 1 the control, showed the lowest aspartame stability, losing 18% of its original aspartame after eight weeks of storage.
- Example 3 containing 5% beta glucans, exhibited the greatest aspartame stability, losing 11% of its original aspartame after eight weeks (a 39% improvement over the control) .
- Example 2 containing 15% beta glucans, lost 12% of its aspartame after eight weeks (a 33% improvement over the control) .
- the formulae were prepared in a conventional mixer in a conventional manner and formed into chewing gum as one-gram pellets. Samples of each formula were stored in sealed pouches in an 85°F oven, and were analyzed for aspartame content after 0,1,2,4,6 and 8 weeks.
- Example 4 the control, lost 51% of its original aspartame after eight weeks. This time, Example 6, containing 5% beta glucans, showed no improvement over the control.
- Example 7 At the highest level of 12% liquid sorbitol, Example 7, the control, lost 60% of its original aspartame after eight weeks.
- Example 9 At the second highest level of 9% liquid sorbitol, Example 9, the control, lost 54% of its original aspartame after eight weeks.
- Example 11 At the third highest level of 6% liquid sorbitol, Example 11, the control, lost 29% of its original aspartame after eight weeks.
- Example 12 containing 15% beta glucans, lost only 16% of its aspartame in the same time period (a 45% improvement over the control) .
- Example 13 the control, lost 13% of its original aspartame after eight weeks.
- Example 14 containing 15% beta glucans, lost only 6.0% of its aspartame in the same period (a 54% improvement over the control) .
- compositions and methods of the present invention are capable of being incorporated in the form of a variety of embodiments, only a few of which have been illustrated and described above.
- the invention may be embodied in other forms without departing from its spirit or essential characteristics.
- the described embodiments are to be considered in all respects only as illustrative and not restrictive, and the scope of the invention, therefore, indicated by the appended claims rather than by the foregoing description. All changes which come within the meaning and range of equivalency of the claims are to be embraced within their scope.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Confectionery (AREA)
- Seasonings (AREA)
Abstract
On obtient une meilleure stabilité de l'aspartame dans le chewing-gum en ajoutant au moins un bêta-glucane au chewing-gum en plus de l'aspartame. Les bêta-gluganes sont ajoutés dans une quantité suffisante pour qu'au bout de huit semaines de stockage du chewing-gum à 85 °F, moins d'aspartame se décompose qu'il ne s'en décomposerait s'il n'y avait pas de bêta-glucanes dans le chewing-gum. On a obtenu une amélioration importante de la stabilité de l'aspartame pour toutes les teneurs en eau du chewing-gum (c-à-d pour des chewing-gums ayant une teneur faible, une teneur moyenne et une teneur forte en eau).
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU59876/94A AU5987694A (en) | 1993-12-30 | 1993-12-30 | Chewing gum containing beta glucan-stabilized aspartame |
PCT/US1993/012671 WO1995017828A1 (fr) | 1993-12-30 | 1993-12-30 | Chewing-gum contenant de l'aspartame stabilise par les beta-glucanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1993/012671 WO1995017828A1 (fr) | 1993-12-30 | 1993-12-30 | Chewing-gum contenant de l'aspartame stabilise par les beta-glucanes |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995017828A1 true WO1995017828A1 (fr) | 1995-07-06 |
Family
ID=22237340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1993/012671 WO1995017828A1 (fr) | 1993-12-30 | 1993-12-30 | Chewing-gum contenant de l'aspartame stabilise par les beta-glucanes |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU5987694A (fr) |
WO (1) | WO1995017828A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104186899A (zh) * | 2014-08-19 | 2014-12-10 | 四川天乙健康科技有限公司 | 高效吸收β-葡聚糖口香糖及制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4871571A (en) * | 1987-06-30 | 1989-10-03 | Novo Industri A/S | Dietetic foodstuff containing low calorie bulking agent |
-
1993
- 1993-12-30 WO PCT/US1993/012671 patent/WO1995017828A1/fr active Application Filing
- 1993-12-30 AU AU59876/94A patent/AU5987694A/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4871571A (en) * | 1987-06-30 | 1989-10-03 | Novo Industri A/S | Dietetic foodstuff containing low calorie bulking agent |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104186899A (zh) * | 2014-08-19 | 2014-12-10 | 四川天乙健康科技有限公司 | 高效吸收β-葡聚糖口香糖及制备方法 |
Also Published As
Publication number | Publication date |
---|---|
AU5987694A (en) | 1995-07-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5612070A (en) | Chewing gums containing natural carbohydrate gum hydrolyzate | |
US5525360A (en) | Chewing gum products using polydextrose | |
US5501864A (en) | Method of making sugar-containing chewing gum with prolonged sweetness intensity | |
US4986991A (en) | Chewing gum having an extended sweetness | |
CA2095126C (fr) | Composition edulcorante synergique, encapsulee contenant de l'aspartame et de l'acesulfame-k et methodes de preparation | |
US5425961A (en) | Chewing gum products using fructooligosaccharides | |
US5399365A (en) | Chewing gum containing palatinose and/or palatinose oligosaccharide | |
CA2132838C (fr) | Gomme a macher a enrobage dur double composition ayant une duree de conservation prolongee | |
US5110608A (en) | Chewing gums having longer lasting sweetness | |
US5431929A (en) | Chewing gum products using oligofructose | |
EP0425115A1 (fr) | Gomme à mâcher édulcorée par du sucralose | |
US5158790A (en) | L-carvone enhanced fruit flavored chewing gum | |
AU653853B2 (en) | Chewing gum containing palatinose and/or palatinose oligosaccharide | |
US5178889A (en) | Use of low fat cocoa powder in non-tack gum base | |
US5192561A (en) | Aspartame stability in chewing gum using an acid gelatin system | |
WO1994014332A1 (fr) | Chewing-gum contenant un hydrolysat de gomme de glucides naturels | |
CA2126192C (fr) | Gommes a macher contenant du polydextrose | |
EP0472500B1 (fr) | Edulcorants type chlordéoxysaccharide stabilisés à l'état solide et procédés de leur préparation | |
US5175009A (en) | Stabilized chewing gum containing acidified humectant | |
US5320854A (en) | Chewing gum containing stabilized hygroscopic ingredients | |
US5296244A (en) | Chewing gum containing aspartame and palatinose oligosaccharide | |
EP0758849B1 (fr) | Procede de fabrication de chewing-gum contenant un melange de sorbitol liquide/mannitol/glycerine | |
US5466471A (en) | Chewing gum containing aspartame and maltodextrin or purified maltodextrin | |
WO1992008371A2 (fr) | Chewing-gum contenant de l'oligofructose | |
WO1995017828A1 (fr) | Chewing-gum contenant de l'aspartame stabilise par les beta-glucanes |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AT AU BB BG BR BY CA CH CZ DE DK ES FI GB HU JP KP KR KZ LK LU MG MN MW NL NO NZ PL PT RO RU SD SE SK UA US VN |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
122 | Ep: pct application non-entry in european phase | ||
NENP | Non-entry into the national phase |
Ref country code: CA |