CA1096233A - Sweeteners - Google Patents
SweetenersInfo
- Publication number
- CA1096233A CA1096233A CA330,179A CA330179A CA1096233A CA 1096233 A CA1096233 A CA 1096233A CA 330179 A CA330179 A CA 330179A CA 1096233 A CA1096233 A CA 1096233A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- deoxy
- fructofuranoside
- beta
- alpha
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Abstract
ABSTRACT OF THE DISCLOSURE
The present invention provides a method of sweetening a substance, comprising incorporating therein a compound selected from the group consisting of 4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-.beta.-D-fructofuranoside; 4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranoside; 4,6-dichloro-4,6-dideoxy-.alpha.-D-galactopyranosyl-6-chloro-6-deoxy .beta.-D-fructofuranoside and 6,1',6'-trichloro-6,1',6'-trideoxysucrose.
The present invention provides a method of sweetening a substance, comprising incorporating therein a compound selected from the group consisting of 4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-.beta.-D-fructofuranoside; 4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranoside; 4,6-dichloro-4,6-dideoxy-.alpha.-D-galactopyranosyl-6-chloro-6-deoxy .beta.-D-fructofuranoside and 6,1',6'-trichloro-6,1',6'-trideoxysucrose.
Description
This invention relates to sweeteners for in~3estible products, oral compositions and sweetening compositions.
By an "ingestible product" there is meant one which in the ordinary course of use is intended to be swallowed, for instance a foodstuff or beverage, or an orally administered pharmaceutical composition. ~y an "oral composition" there is meant one which in the ordinary course of use is not intended to be ingested as such, but is taken into the mouth for the treatment of the throat or buccal cavity, for instance a tooth-paste, tooth powder, mouth wash, gargle, troche, dental lotionor cnewing gum~ By a "sweetening composition" there is meant a composition which is not itself taken orally, either to be ingested or held in the mouth, but instead is intended to be added to other ingestible products or oral compositions to render them sweet or to increase their sweetness.
Although sucrose is still the most widely used sweet-ening agent, many efforts have been made to find substantially sweeter alternatives which could be used when it is desired -to combine a high degree of sweetness with a low calorie content and/or a low risk of dental caries, for example in dietetic products and in the manufacture of soft drinks. The two most successful non--sucrose sweeteners (that is to say sweeteners comprising a compound other than sucrose itself) to date have been saccharin and cyclamate, having respectively about 200 and about 30 times the sweetening power of sucrose, but the use of these sweeteners, particularly cyc]amate, has recently been restricted or banned in some countries because of doubts about their safety. Saccharin also suffers from the disadvantage of an unpleasantlybitter after-taste which can be detected by many people.
More recently, many other non-sucrose sweetcners have been investigated, some of natural origin and others synthetic, covering a wide range of chemical structures. These compounds have included proteins, such as monellin, thaumatin and miraculin, dipeptides such as aspartame, and dihydrochalcones such as neo-hesperidin dihydrochalcone. Ilowever, apart from the difficulties of synthesizing or extracting such sweeteners, they do not nec-essarily possess the same quality of sweetness as sucrose: in particular, as compared with sucrose, the sweetness may be slow in onset and relatively lingering, and there may be a li~uorice-like or other after-taste, making the sweetener unsuitable as a d.ireet replacement for sucrose unless these differences can be mas~ed.
Although numerous sweeteners of widely diverse chemical structures have now been investigated, it is significant to note that sweetness substantially greater than that of sucrose has not been discovered in any derivative of suerose or in any other ear~onydrate: when an intensely sweet substance has been dis-eovered, sueh as saceharin, cyclamate and the other non-suerose sweeteners already mentioned, its structure has always been radieally different from that of sucrose. Indeed, it is known that the presenee of some substituents on the suerose molecule ean, in faet, destroy its sweetness and even impart a bitter t.aste.
Most surprisinglyj and in complete contrast to previous knowledge about non-suerose sweeteners, we have now discovered that eertain derivatives of sucrose and of a sucrose isomer are very mueh sweeter than suerose itself, their sweetness being eomparable in intensity with that of saeeharin, but having a quality similar to that of sucrose.
Aeeording to the present invention we provide as sweetening agents compounds selected from the group consisting of 4--ehloro-4-deoxy-~-D-galactopyranosyl-~-D--fructofuranoside;
4-cllloro-4-deoxy-~-D-galactopyranoSyl-1, 6--dichloro-1, 6-dideoxy-~-D-fructofuranoside; 4,6--dichloro-4~ 6-dideoxy~ D-galacto-pyranosyl-6-chloro-6~deoxy~ D fructofuranoside and 6,1', 6'-trichloro-6, 1', 6'-trideoxy-sucrose.
The compounds can be used as sweetening agents in any conventional way, including the sweetening of "ingestible pro-ducts" (as previously defined), for example foodstuffs, bev-erages and orallyadministered pharmaceutical compositions, and of "oral compositions" (as previously defined), for example toothpastes, chewing gums and mouth washes. They can also be used, with conventional liquid or solid extenders and carriers, in "sweetening compositions" (as previously defined).
The extender or carrier comprises any suitable vehicle for the sucrose derivative so that it can be formulated in a composition which can conveniently be used for sweetening other products, for example granules, tablets or drops. The extender or carrier may thus include, for example, conventional water-dispersible tabletting ingredients, such as starch, lactose and sucrose itself; low--density bulking agents to provide a granular sweetening composition having a volume per unit sweetness equivalent to that of sucrose, for example, spray dried malto-dextrins- and aqueous solutions containing adjuvants such as stabilising agents, colouring agents and viscosity-adjusting agents.
Beverages, such as soft drinks, containing one of the said sucrose derivatives may be formulated either as sugar-free dietetic products, or "sugar-reduced" products containing the minimum amount of sugar required by law. In the absence of sugar lt is desirable to add further agents to provide a "mouth-feel" similar to that provided by sugar, for example, pectin or a vegetable gum. For example, pectin may be added at a level of from 0.1 to 0.15~ in a bottling syrup.
The compounds which may be used according to -t~le present 23;~
invention are shown in the following Table. The compounds are represented by the formula: -R~ R~
R ~--~ \ ~Rl o ~ >~ ~/6 1~0 ~1 o / ~
OH
.
Compound No. ~1 ~ R R ~ ~PPrtXlrnS(X Sucrose)*
I . l
By an "ingestible product" there is meant one which in the ordinary course of use is intended to be swallowed, for instance a foodstuff or beverage, or an orally administered pharmaceutical composition. ~y an "oral composition" there is meant one which in the ordinary course of use is not intended to be ingested as such, but is taken into the mouth for the treatment of the throat or buccal cavity, for instance a tooth-paste, tooth powder, mouth wash, gargle, troche, dental lotionor cnewing gum~ By a "sweetening composition" there is meant a composition which is not itself taken orally, either to be ingested or held in the mouth, but instead is intended to be added to other ingestible products or oral compositions to render them sweet or to increase their sweetness.
Although sucrose is still the most widely used sweet-ening agent, many efforts have been made to find substantially sweeter alternatives which could be used when it is desired -to combine a high degree of sweetness with a low calorie content and/or a low risk of dental caries, for example in dietetic products and in the manufacture of soft drinks. The two most successful non--sucrose sweeteners (that is to say sweeteners comprising a compound other than sucrose itself) to date have been saccharin and cyclamate, having respectively about 200 and about 30 times the sweetening power of sucrose, but the use of these sweeteners, particularly cyc]amate, has recently been restricted or banned in some countries because of doubts about their safety. Saccharin also suffers from the disadvantage of an unpleasantlybitter after-taste which can be detected by many people.
More recently, many other non-sucrose sweetcners have been investigated, some of natural origin and others synthetic, covering a wide range of chemical structures. These compounds have included proteins, such as monellin, thaumatin and miraculin, dipeptides such as aspartame, and dihydrochalcones such as neo-hesperidin dihydrochalcone. Ilowever, apart from the difficulties of synthesizing or extracting such sweeteners, they do not nec-essarily possess the same quality of sweetness as sucrose: in particular, as compared with sucrose, the sweetness may be slow in onset and relatively lingering, and there may be a li~uorice-like or other after-taste, making the sweetener unsuitable as a d.ireet replacement for sucrose unless these differences can be mas~ed.
Although numerous sweeteners of widely diverse chemical structures have now been investigated, it is significant to note that sweetness substantially greater than that of sucrose has not been discovered in any derivative of suerose or in any other ear~onydrate: when an intensely sweet substance has been dis-eovered, sueh as saceharin, cyclamate and the other non-suerose sweeteners already mentioned, its structure has always been radieally different from that of sucrose. Indeed, it is known that the presenee of some substituents on the suerose molecule ean, in faet, destroy its sweetness and even impart a bitter t.aste.
Most surprisinglyj and in complete contrast to previous knowledge about non-suerose sweeteners, we have now discovered that eertain derivatives of sucrose and of a sucrose isomer are very mueh sweeter than suerose itself, their sweetness being eomparable in intensity with that of saeeharin, but having a quality similar to that of sucrose.
Aeeording to the present invention we provide as sweetening agents compounds selected from the group consisting of 4--ehloro-4-deoxy-~-D-galactopyranosyl-~-D--fructofuranoside;
4-cllloro-4-deoxy-~-D-galactopyranoSyl-1, 6--dichloro-1, 6-dideoxy-~-D-fructofuranoside; 4,6--dichloro-4~ 6-dideoxy~ D-galacto-pyranosyl-6-chloro-6~deoxy~ D fructofuranoside and 6,1', 6'-trichloro-6, 1', 6'-trideoxy-sucrose.
The compounds can be used as sweetening agents in any conventional way, including the sweetening of "ingestible pro-ducts" (as previously defined), for example foodstuffs, bev-erages and orallyadministered pharmaceutical compositions, and of "oral compositions" (as previously defined), for example toothpastes, chewing gums and mouth washes. They can also be used, with conventional liquid or solid extenders and carriers, in "sweetening compositions" (as previously defined).
The extender or carrier comprises any suitable vehicle for the sucrose derivative so that it can be formulated in a composition which can conveniently be used for sweetening other products, for example granules, tablets or drops. The extender or carrier may thus include, for example, conventional water-dispersible tabletting ingredients, such as starch, lactose and sucrose itself; low--density bulking agents to provide a granular sweetening composition having a volume per unit sweetness equivalent to that of sucrose, for example, spray dried malto-dextrins- and aqueous solutions containing adjuvants such as stabilising agents, colouring agents and viscosity-adjusting agents.
Beverages, such as soft drinks, containing one of the said sucrose derivatives may be formulated either as sugar-free dietetic products, or "sugar-reduced" products containing the minimum amount of sugar required by law. In the absence of sugar lt is desirable to add further agents to provide a "mouth-feel" similar to that provided by sugar, for example, pectin or a vegetable gum. For example, pectin may be added at a level of from 0.1 to 0.15~ in a bottling syrup.
The compounds which may be used according to -t~le present 23;~
invention are shown in the following Table. The compounds are represented by the formula: -R~ R~
R ~--~ \ ~Rl o ~ >~ ~/6 1~0 ~1 o / ~
OH
.
Compound No. ~1 ~ R R ~ ~PPrtXlrnS(X Sucrose)*
I . l
2 Cl H Cl OH Cl 2000
3, ~H H Cl Cl Cl 4 Cl OH H Cl Cl l00 . .. .
*Sweetness Evaluation The sweetness is evaluated in aqueous solution, bycomparison with a 10% by weight aqueous solution of sucrose.
The results were obtained from a small taste panel and are, tl~erefore, not statistically accurate, but indicate the approx-imate order of sweetness.
The cor,lpounas in Table 1 are as follows (the sys-terriatic nomenclature is given first, followed br a trivial n.-,me base~ on "galacto sucrose" in chose cases where a 4--cliloro substituent is p L~resent):
1. 4-chloro-4-deox~ -D--c~alacto,oyranosyl--~-D-~' fructofuranoside (i.e. 4-chloro-4-deoxygalactosucrose) 2. 4-chloro-4-deoxy-~-D-galactopyrallosyl-1, 6-dicnloro-1, ~-di~eoxy-~-D-fructofuranoside (i.e. 4-1', 6'-trichloro-4, 1', 6'-trideoxygalacto sucrose) 3. 4,6-dichloro-4, 6-dideoxy-~-D--galactopyranosyl-6-chloro-6-deoxy~ D-fructofuranoside (i.e. 4,6,6'-trichloro-4, 6,6'-trideoxygalactosucrose)
*Sweetness Evaluation The sweetness is evaluated in aqueous solution, bycomparison with a 10% by weight aqueous solution of sucrose.
The results were obtained from a small taste panel and are, tl~erefore, not statistically accurate, but indicate the approx-imate order of sweetness.
The cor,lpounas in Table 1 are as follows (the sys-terriatic nomenclature is given first, followed br a trivial n.-,me base~ on "galacto sucrose" in chose cases where a 4--cliloro substituent is p L~resent):
1. 4-chloro-4-deox~ -D--c~alacto,oyranosyl--~-D-~' fructofuranoside (i.e. 4-chloro-4-deoxygalactosucrose) 2. 4-chloro-4-deoxy-~-D-galactopyrallosyl-1, 6-dicnloro-1, ~-di~eoxy-~-D-fructofuranoside (i.e. 4-1', 6'-trichloro-4, 1', 6'-trideoxygalacto sucrose) 3. 4,6-dichloro-4, 6-dideoxy-~-D--galactopyranosyl-6-chloro-6-deoxy~ D-fructofuranoside (i.e. 4,6,6'-trichloro-4, 6,6'-trideoxygalactosucrose)
4. 6,1',6'-trichloro-6, 1',6'-trideoxysucrose The remarkable sweetness of the compounds is combined with an LDSo (lethal dose 50%) which, in the case of compound 2 in Table 1, for example, is in excess of 16g/kg in mice, that being the largest dose which can be administered in practice.
The compounds are all ~nown and can be-prepared by the synthetic routes disclosed in the chemical literature. However, none of the compounds has previously been recognised as possessing any useful sweetness.
The compound 2 is reported in Carbohyd. Res., 40(1975), 285; Compound 3 in Carbohyd. ~es., 44, (1375), 37; and Com~ound 4 in Carbohyd. Res., 25, (197~), 504 and ibid 44, (1975), 12-13.
Com~ound 1 is reported in Carbohyd, Res., 40, (1975), 285-298.
All the compounds may be prepared by reaction of a sucrose ester, having free hydroxy groups in the portions re-uired to ~e c}llorinated, with sulphuryl chloride to o~tain the corresponding chlorosulphate derivative. This, on treatment with a source of chloride ions such as lithium chloride, in amide solvent such as hexametllyl pihosplloric triamide, yields the cillorinated sucrose ester. Hydrolysis of the chloro-ester, e.g. using sodium methoxide in dry methanol, then liberates the free chlorosucrose. The reaction with sulphuryl chloride is con-~7eniently effected at a reduced temperature in an inert solvent in the presence of a base, for example chloroEorm containing pyridine.
The compounds are all ~nown and can be-prepared by the synthetic routes disclosed in the chemical literature. However, none of the compounds has previously been recognised as possessing any useful sweetness.
The compound 2 is reported in Carbohyd. Res., 40(1975), 285; Compound 3 in Carbohyd. ~es., 44, (1375), 37; and Com~ound 4 in Carbohyd. Res., 25, (197~), 504 and ibid 44, (1975), 12-13.
Com~ound 1 is reported in Carbohyd, Res., 40, (1975), 285-298.
All the compounds may be prepared by reaction of a sucrose ester, having free hydroxy groups in the portions re-uired to ~e c}llorinated, with sulphuryl chloride to o~tain the corresponding chlorosulphate derivative. This, on treatment with a source of chloride ions such as lithium chloride, in amide solvent such as hexametllyl pihosplloric triamide, yields the cillorinated sucrose ester. Hydrolysis of the chloro-ester, e.g. using sodium methoxide in dry methanol, then liberates the free chlorosucrose. The reaction with sulphuryl chloride is con-~7eniently effected at a reduced temperature in an inert solvent in the presence of a base, for example chloroEorm containing pyridine.
- 5 -A similar metilod can ~e used for furtller chlorinating an already clllorinated sucrose derivative.
Tne following ~xamples illustrate the invention further (tcmperatures are given in degrees centigrade).
Sweetening tablets for beverages, etc.
Each ta~let contains:
Compound 2 2 mg together Witil a dispersable tablet base (ca. 60 mg) containing sucrose, gum arabic and magnesium stearate, and is equivalent in sweetness to about 4.5 g sucrose.
Bulked sweetener A bulked sweetener having the same sweetness as an equivalent volume of sucrose (granulated sugar) is prepared by mixing the following ingredients and spray-~drying to a bulk density of 0.2 g/cc:
maltodextrin solution containing dry weight 222.2 g Compound 2 0.5 g The resulting composition has a sweetening po~er equivalent to approximately 2 kilograms of sugar.
Reduced calorie cola drink containing sugar Ingredients to prepare 100 ml bottling syrup:
Compound 2 20 mg Sugar 60 mg Benzoic acid 35 mg Pllosphoric acid (conc.)1 ml Cola flavour 1.1 ml Colour ad lib.
Make up to 100 ml with mineral water.
This syrup may then be added in 25 ml doses to carbonated 225 ml aliquots of chilled mineral water.
Tne following ~xamples illustrate the invention further (tcmperatures are given in degrees centigrade).
Sweetening tablets for beverages, etc.
Each ta~let contains:
Compound 2 2 mg together Witil a dispersable tablet base (ca. 60 mg) containing sucrose, gum arabic and magnesium stearate, and is equivalent in sweetness to about 4.5 g sucrose.
Bulked sweetener A bulked sweetener having the same sweetness as an equivalent volume of sucrose (granulated sugar) is prepared by mixing the following ingredients and spray-~drying to a bulk density of 0.2 g/cc:
maltodextrin solution containing dry weight 222.2 g Compound 2 0.5 g The resulting composition has a sweetening po~er equivalent to approximately 2 kilograms of sugar.
Reduced calorie cola drink containing sugar Ingredients to prepare 100 ml bottling syrup:
Compound 2 20 mg Sugar 60 mg Benzoic acid 35 mg Pllosphoric acid (conc.)1 ml Cola flavour 1.1 ml Colour ad lib.
Make up to 100 ml with mineral water.
This syrup may then be added in 25 ml doses to carbonated 225 ml aliquots of chilled mineral water.
- 6 -EXA_PLE 4 Carbonated low calorie lemonade (sugar~free) . _ . . . _ .
Ingredients to prepare 100 ml syrup:
Compound 2 19 mg Benzoic acid 35 mg Citric acid (dry base) 1.67 g Lemon essence 0.8 g Make up to 100 ml in mineral water.
Tl~is syrup can be added in 25 ml doses to 225 ml aliquots of carbonated cnilled mineral water.
Tootllpaste _ _ % by weight Dibasic calcium phospilate 50%
Clycerol 20%
Sodium lauryl sulphate 2.5%
Spearmint oil 2.5%
Gum tragacanth 1.0%
Compound 2 0.008%
Water 23.992%
The ingredients are mixed to produce a sl~earmint ~lavoured tooth-paste of accepta~le sweetness but free from sugar or saccharin.
part by weight Polyvinyl acetate 20 Butyl plltllalylbutylglycolate 3 Polyisobutylene 3 Microcrystalline wax 2 3~ Calcium carbonate 2 Flavouring/aroma Compound 2 0.17 ~' Glucose 10 The above chewing gum base can be cut into conventional tablets or stri~s.
~1
Ingredients to prepare 100 ml syrup:
Compound 2 19 mg Benzoic acid 35 mg Citric acid (dry base) 1.67 g Lemon essence 0.8 g Make up to 100 ml in mineral water.
Tl~is syrup can be added in 25 ml doses to 225 ml aliquots of carbonated cnilled mineral water.
Tootllpaste _ _ % by weight Dibasic calcium phospilate 50%
Clycerol 20%
Sodium lauryl sulphate 2.5%
Spearmint oil 2.5%
Gum tragacanth 1.0%
Compound 2 0.008%
Water 23.992%
The ingredients are mixed to produce a sl~earmint ~lavoured tooth-paste of accepta~le sweetness but free from sugar or saccharin.
part by weight Polyvinyl acetate 20 Butyl plltllalylbutylglycolate 3 Polyisobutylene 3 Microcrystalline wax 2 3~ Calcium carbonate 2 Flavouring/aroma Compound 2 0.17 ~' Glucose 10 The above chewing gum base can be cut into conventional tablets or stri~s.
~1
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method of sweetening a substance, comprising in-corporating therein a compound selected from the group consisting of 4-chloro--4-deoxy-.alpha.-D-galactopyranosyl-.beta.-D-fructofuranoside;
4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-1, 6-dichloro-1, 6-dideoxy-.beta.-D-fructofuranoside; 4, 6-dichloro-4, 6-dideoxy-.alpha.-D-galactopyrano-syl-6-chloro-6-deoxy-.beta.-D-fructofuranoside and 6, 1', 6'-trichloro-6, 1', 6'-trideoxysucrose.
4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-1, 6-dichloro-1, 6-dideoxy-.beta.-D-fructofuranoside; 4, 6-dichloro-4, 6-dideoxy-.alpha.-D-galactopyrano-syl-6-chloro-6-deoxy-.beta.-D-fructofuranoside and 6, 1', 6'-trichloro-6, 1', 6'-trideoxysucrose.
2. An ingestible product or oral composition containing a compound selected from the group consisting of 4-chloro-4-deoxy-.alpha.-D-galacto topyranosyl-.beta.-D-fructofuranoside; 4-chloro-4-deoxy-.alpha.-D-galactopyranosyl-l, 6-dichloro-1, 6-dideoxy-.beta.-D-fructofuranoside-4, 6-dichloro-4, 6-dideoxy-.alpha.-D-galactopyranosyl-6-chloro--6-deoxy-.beta.-D-fructofuranoside and 6, 1', 6'-trichloro-6, 1', 6'-trideoxysucrose.
3. A product or composition according to Claim 2, in the form of a beverage or other liquid also containing an additive to improve "mouthfeel".
4. A product or composition according to Claim 3, in which the additive is pectin or a vegetable gum.
5. A sweetening composition comprising a compound selected from the group consisting of 4-chloro-4 deoxy-.alpha.-D-galactopyranosyl-.beta.-D-fructofuranoside; 4-chloro-4-deoxy.alpha.-D-galactopyranosyl-1, 6-dichloro-1, 6-dideoxy-.beta.-D-fructofuranoside; 4, 6-dichloro-4,6-dideoxy-.alpha.-D-galactopyranosyl-6-chloro-6-deoxy-.beta.-D-fructo-furanoside and 6, 1', 6'-trichloro-6, 1', 6'-trideoxysucrose, together with a solid extender or carrier, or with a liquid extender or carrier containing an adjuvant.
6. A composition according to Claim 5, in the form of tablets, granules or a solution in a dropper pack.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA330,179A CA1096233A (en) | 1976-01-08 | 1979-06-20 | Sweeteners |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB616/76 | 1976-01-08 | ||
| GB616/76A GB1543167A (en) | 1976-01-08 | 1976-01-08 | Sweeteners |
| CA268,863A CA1076110A (en) | 1976-01-08 | 1976-12-29 | Sweeteners |
| CA330,179A CA1096233A (en) | 1976-01-08 | 1979-06-20 | Sweeteners |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096233A true CA1096233A (en) | 1981-02-24 |
Family
ID=27164847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA330,179A Expired CA1096233A (en) | 1976-01-08 | 1979-06-20 | Sweeteners |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1096233A (en) |
-
1979
- 1979-06-20 CA CA330,179A patent/CA1096233A/en not_active Expired
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|---|---|---|---|
| MKEX | Expiry |