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US3867533A
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Preparation of aqueous gel compositions containing a water-insoluble organic ingredient
Assignee: BASF Corp
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Filing: 1973-09-12
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Granted: 1975-02-18
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Expires: 1993-09-12
Abstract
Abstract Aqueous gel compositions containing a water-insoluble pharmaceutically or cosmetically active organic ingredient are prepared employing as gelling agents, polyoxyethylene polyoxypropylene block copolymers. The resulting compositions are highly stable and are useful in many pharmaceutical and cosmetic applications.
Inventors
- 👤 Irving R Schmolka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 10:25
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/02; A61K8/04; A61K8/042; A01; A01N; A01N25/00; A01N25/02; A01N25/04; A61K47/00; A61K47/06; A61K47/08; A61K47/10; A61K8/18; A61K8/72; A61K8/90; A61K9/00; A61K9/0012; A61K9/0014; A61Q; A61Q17/00; A61Q17/005; A61Q17/02; A61Q19/00; C; C08; C08L; C08L71/00; C08L71/02
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
172 words
A METHOD OF REPARING AN AQUEOUS GEL COMPOSITION CONTAINING A WATER-INSOLUBLE PHARMACEUTICALLY OR COSMETICALLY ACTIVE ORGANIC INGREDIENT WHICH COMPRISES THE FOLLOWING STEPS: A. HEATING FROM 0.1 PART TO 10 PARTS BY WEIGHT OF SAID ORGANIC INGREDIENT ALONG SAID FROM 50 PARTS TO 15 PARTS BY WEIGHT OF A POLYOXYETHYLENE POLYOXYPROPYLENE BLOCK COPOLYMER TO A TEMPERATURE OF ABOUT 50*C. TO 65*C, SAID COPOLYMER HAVING THE FORMULA: HO(C2H4O)B(C3H6O)A(C2H4O)BH WHEREIN A IS AN INTEGER SUCH THAT THE HYDROPHOBE REPRESENTED BY (C3H6O) HAS A MOLECULAR WEIGHT OF FROM 2250 TO 4000, AND B IS AN INTEGER SUCH THAT THE HYDROPHILE PORTION REPRESENTED BY (C2H4O) CONSISTUTES FROM ABOUT 10 TO 90 WEIGHT PERCENT OF THE COPOLYMER, B. ADDING FROM 50 PARTS TO 85 PARTS BY WEIGHT OF WATER TO THE MIXTURE RESULTING FROM STEP (A) AND COOLING THE RESULTING AQUEOUS MIXTURE TO 5*C. TO 10*C WITH STIRRING UNTIL A HONOGENEOUS SOLUTION IS OBTAINED, AND C. ALLOWING THE HOMOGENEOUS SOLUTION FROM STEP (B) TO WARM TO AMBIENT TEMPERATURES WHEREBY A GEL COMPOSITION IS OBTAINED, WITH THE PROVISOS THAT:
Claim 2
Independent Claim
172 words
A METHOD OF REPARING AN AQUEOUS GEL COMPOSITION CONTAINING A WATER-INSOLUBLE PHARMACEUTICALLY OR COSMETICALLY ACTIVE ORGANIC INGREDIENT WHICH COMPRISES THE FOLLOWING STEPS: A. HEATING FROM 0.1 PART TO 10 PARTS BY WEIGHT OF SAID ORGANIC INGREDIENT ALONG SAID FROM 50 PARTS TO 15 PARTS BY WEIGHT OF A POLYOXYETHYLENE POLYOXYPROPYLENE BLOCK COPOLYMER TO A TEMPERATURE OF ABOUT 50*C. TO 65*C, SAID COPOLYMER HAVING THE FORMULA: HO(C2H4O)B(C3H6O)A(C2H4O)BH WHEREIN A IS AN INTEGER SUCH THAT THE HYDROPHOBE REPRESENTED BY (C3H6O) HAS A MOLECULAR WEIGHT OF FROM 2250 TO 4000, AND B IS AN INTEGER SUCH THAT THE HYDROPHILE PORTION REPRESENTED BY (C2H4O) CONSISTUTES FROM ABOUT 10 TO 90 WEIGHT PERCENT OF THE COPOLYMER, B. ADDING FROM 50 PARTS TO 85 PARTS BY WEIGHT OF WATER TO THE MIXTURE RESULTING FROM STEP (A) AND COOLING THE RESULTING AQUEOUS MIXTURE TO 5*C. TO 10*C WITH STIRRING UNTIL A HONOGENEOUS SOLUTION IS OBTAINED, AND C. ALLOWING THE HOMOGENEOUS SOLUTION FROM STEP (B) TO WARM TO AMBIENT TEMPERATURES WHEREBY A GEL COMPOSITION IS OBTAINED, WITH THE PROVISOS THAT:
Claim 3
Dependent Claim
62 words
WHEN A IS FORMULA I IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 2250, THEN THE ETHYLENE OXIDE CONTENT IS FROM 50 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL AVEVAGE MOLECULAR WEIGHT OF THE CCOPOLYMER IS FROM 4600 TO 10,750 AND THE GEL COMPOSITION COMPRISES FROM 40 TO 50 WEIGHT PERCENT OF THE COPOLYMER,
Claim 4
Dependent Claim
62 words
WHEN A IS FORMULA I IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 2250, THEN THE ETHYLENE OXIDE CONTENT IS FROM 50 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL AVEVAGE MOLECULAR WEIGHT OF THE CCOPOLYMER IS FROM 4600 TO 10,750 AND THE GEL COMPOSITION COMPRISES FROM 40 TO 50 WEIGHT PERCENT OF THE COPOLYMER,
Claim 5
Dependent Claim
62 words
WHEN A IN FORMULAR 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 2750, THEN THE ETHYLENE OXIDE CONTENT IS FROM 45 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL AVERAGE MOLECULAR WEIGHT OF THE COPOLYMER IS FROM 4910 TO 13,500 AND THE GEL COMPOSITION COMPRISES FROM 40 TO 50 WEIGHT PERCENT OF THE COPOLYMER,
Claim 6
Dependent Claim
62 words
WHEN A IN FORMULAR 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 2750, THEN THE ETHYLENE OXIDE CONTENT IS FROM 45 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL AVERAGE MOLECULAR WEIGHT OF THE COPOLYMER IS FROM 4910 TO 13,500 AND THE GEL COMPOSITION COMPRISES FROM 40 TO 50 WEIGHT PERCENT OF THE COPOLYMER,
Claim 7
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 2750, then the ethylene oxide content is from 45 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 13,500 and the gel composition comprises from 40 to 50 weight percent of the copolymer;
Claim 8
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 2750, then the ethylene oxide content is from 45 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 13,500 and the gel composition comprises from 40 to 50 weight percent of the copolymer;
Claim 9
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 2750, then the ethylene oxide content is from 45 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 13,500 and the gel composition comprises from 40 to 50 weight percent of the copolymer;
Claim 10
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 2750, then the ethylene oxide content is from 45 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 13,500 and the gel composition comprises from 40 to 50 weight percent of the copolymer;
Claim 11
Independent Claim
172 words
A method of preparing an aqueous gel composition containing a water-insoluble pharmaceutically or cosmetically active organic ingredient which comprises the following steps: a. heating from 50 parts to 15 parts of a polyoxyethylene polyoxypropylene block copolymer to a temperature of about 50*C. to 65*C., said copolymer having the formula: HO(C2H4O)b(C3H6O)a(C2H4O)bH wherein a is an integer such that the hydrophobe represented by (C3H6O) has a molecular weight of at least 2250, and b is an integer such that the hydrophile portion represented by (C2H4O) constitutes from about 10 to 90 weight percent of the copolymer, b. adding from 0.1 part to 10 parts of said organic ingredient to the melted copolymer from step (a), c. adding from 50 parts to 85 parts of water to the mixture resulting froM step (b) and cooling the resulting aqueous mixture to 5*C. to 10*C. with stirring until a homogeneous solution is obtained, and d. allowing the homogeneous solution from step (c) to warm to ambient temperatures whereby a gel composition is obtained, with the provisos that:
Claim 12
Independent Claim
172 words
A method of preparing an aqueous gel composition containing a water-insoluble pharmaceutically or cosmetically active organic ingredient which comprises the following steps: a. heating from 50 parts to 15 parts of a polyoxyethylene polyoxypropylene block copolymer to a temperature of about 50*C. to 65*C., said copolymer having the formula: HO(C2H4O)b(C3H6O)a(C2H4O)bH wherein a is an integer such that the hydrophobe represented by (C3H6O) has a molecular weight of at least 2250, and b is an integer such that the hydrophile portion represented by (C2H4O) constitutes from about 10 to 90 weight percent of the copolymer, b. adding from 0.1 part to 10 parts of said organic ingredient to the melted copolymer from step (a), c. adding from 50 parts to 85 parts of water to the mixture resulting froM step (b) and cooling the resulting aqueous mixture to 5*C. to 10*C. with stirring until a homogeneous solution is obtained, and d. allowing the homogeneous solution from step (c) to warm to ambient temperatures whereby a gel composition is obtained, with the provisos that:
Claim 13
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 2750, then the ethylene oxide content is from 45 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 13,500 and the gel composition comprises from 40 to 50 weight percent of the copolymer;
Claim 14
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 2750, then the ethylene oxide content is from 45 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 13,500 and the gel composition comprises from 40 to 50 weight percent of the copolymer;
Claim 15
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 3250, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 15,510 and the gel composition comprises from 30 to 50 weight percent of the copolymer;
Claim 16
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 3250, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 15,510 and the gel composition comprises from 30 to 50 weight percent of the copolymer;
Claim 17
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 3250, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 15,510 and the gel composition comprises from 30 to 50 weight percent of the copolymer;
Claim 18
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 3250, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 15,510 and the gel composition comprises from 30 to 50 weight percent of the copolymer;
Claim 19
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 3250, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 15,510 and the gel composition comprises from 30 to 50 weight percent of the copolymer;
Claim 20
Dependent Claim
62 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 3250, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 4910 to 15,510 and the gel composition comprises from 30 to 50 weight percent of the copolymer;
Claim 21
Independent Claim
154 words
A method of preparing an aqueous gel composition containing a water-insoluble pharmaceutically or cosmetically active organic ingredient which comprises the following steps: a. heating from 0.1 part to 10 parts of said organic ingredient, 50 parts to 85 parts of water and from 50 parts to 15 parts of a polyoxyethylene polyoxypropylene block copolymer to a temperature of 80*C. to 90*C., said copolymer having the formula: HO(C2H4O)b(C3H6O)a(C2H4O)bH wherein a is an integer such that the hydrophobe represented by (C3H6O) has a molecular weight of at least 2250, and b is an integer such that the hydrophile portion represented by (C2H4O) constitutes from about 10 to 90 weight percent of the copolymer, b. gently stirring the mixture from step (a) until the block copolymer has dissolved whereby a clear homogeneous solution is obtained and c. cooling the homogeneous solution from step (b) to room temperature whereby a gel composition is obtained, with the provisos that:
Claim 22
Independent Claim
154 words
A method of preparing an aqueous gel composition containing a water-insoluble pharmaceutically or cosmetically active organic ingredient which comprises the following steps: a. heating from 0.1 part to 10 parts of said organic ingredient, 50 parts to 85 parts of water and from 50 parts to 15 parts of a polyoxyethylene polyoxypropylene block copolymer to a temperature of 80*C. to 90*C., said copolymer having the formula: HO(C2H4O)b(C3H6O)a(C2H4O)bH wherein a is an integer such that the hydrophobe represented by (C3H6O) has a molecular weight of at least 2250, and b is an integer such that the hydrophile portion represented by (C2H4O) constitutes from about 10 to 90 weight percent of the copolymer, b. gently stirring the mixture from step (a) until the block copolymer has dissolved whereby a clear homogeneous solution is obtained and c. cooling the homogeneous solution from step (b) to room temperature whereby a gel composition is obtained, with the provisos that:
Claim 23
Dependent Claim
62 words
WHEN A IN FORMULA 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF HYDROPHOBE IS ABOUT 3250, THEN THE ETHYLENE OXIDE CONTENT IS FROM 35 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL WEIGHT AVERAGE MOLECULAR WEIGHT OF THE COPOLYMER IS FROM 4910 TO 15,510 AND THE GEL COMPOSITION COMPRISES FROM 30 TO 50 WEIGHT PERCENT OF THE COPOLYMER,
Claim 24
Dependent Claim
62 words
WHEN A IN FORMULA 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF HYDROPHOBE IS ABOUT 3250, THEN THE ETHYLENE OXIDE CONTENT IS FROM 35 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL WEIGHT AVERAGE MOLECULAR WEIGHT OF THE COPOLYMER IS FROM 4910 TO 15,510 AND THE GEL COMPOSITION COMPRISES FROM 30 TO 50 WEIGHT PERCENT OF THE COPOLYMER,
Claim 25
Dependent Claim
141 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 6150 to 2000 and the gel composition comprises from 30 to 50 weight percent of the copolymer, with the further proviso that when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, the ethylene oxide content is from 70 to 90 weight percent, the total average molecular weight of the block polymer is from 16,000 to 20,000 and the gel composition comprises from 15 to 50 weight percent of the copolymer, all parts by weight being based on 100 parts by weight of said gel composition.
Claim 26
Dependent Claim
141 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 6150 to 2000 and the gel composition comprises from 30 to 50 weight percent of the copolymer, with the further proviso that when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, the ethylene oxide content is from 70 to 90 weight percent, the total average molecular weight of the block polymer is from 16,000 to 20,000 and the gel composition comprises from 15 to 50 weight percent of the copolymer, all parts by weight being based on 100 parts by weight of said gel composition.
Claim 27
Dependent Claim
36 words
The method of claim 1 wherein the polyoxyethylene polyoxypropylene block copolymer has an average molecular weight hydrophobe of 4000 and the hydrophile portion of the copolymer constitutes from 70 to 90 weight percent of the copolymer.
Claim 28
Dependent Claim
141 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4,000, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 6150 to 2000 and the gel composition comprises from 30 to 50 weight percent of the copolymer, with the further proviso that when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, the ethylene oxide content is from 70 to 90 weight percent, the total average molecular weight of the block polymer is from 16,000 to 20,000 and the gel composition comprises from 15 to 50 weight percent of the copolymer, all parts by weight being based on 100 parts by weight of said gel composition.
Claim 29
Dependent Claim
141 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4,000, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 6150 to 2000 and the gel composition comprises from 30 to 50 weight percent of the copolymer, with the further proviso that when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, the ethylene oxide content is from 70 to 90 weight percent, the total average molecular weight of the block polymer is from 16,000 to 20,000 and the gel composition comprises from 15 to 50 weight percent of the copolymer, all parts by weight being based on 100 parts by weight of said gel composition.
Claim 30
Dependent Claim
141 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 6150 to 2000 and the gel composition comprises from 30 to 50 weight percent of the copolymer, with the further proviso that when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, the ethylene oxide content is from 70 to 90 weight percent, the total average molecular weight of the block polymer is from 16,000 to 20,000 and the gel composition comprises from 15 to 50 weight percent of the copolymer, all parts by weight being based on 100 parts by weight of said gel composition.
Claim 31
Dependent Claim
141 words
when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, then the ethylene oxide content is from 35 to 90 weight percent of the copolymer, the total average molecular weight of the copolymer is from 6150 to 2000 and the gel composition comprises from 30 to 50 weight percent of the copolymer, with the further proviso that when a in Formula I is an integer such that the average molecular weight of the hydrophobe is about 4000, the ethylene oxide content is from 70 to 90 weight percent, the total average molecular weight of the block polymer is from 16,000 to 20,000 and the gel composition comprises from 15 to 50 weight percent of the copolymer, all parts by weight being based on 100 parts by weight of said gel composition.
Claim 32
Dependent Claim
141 words
WHEN A IN FORMULA 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 4000, THEN THE ETHYLENE OXIDE CONTENT IS FROM 35 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL AVERAGE MOLECULAR WEIGHT OF THE COPOLYMER IS FROM 6150 TO 2000 AND THE GEL COMPOSITION COMPRISES FROM 30 TO 50 WEIGHT PERCENT OF THE COPOLYMER, WITH THE FURTHER PROVISO THAT WHEN A IN FORMULA 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 4000, THE ETHYLENE OXIDE CONTENT IS FROM 70 TO 90 WEIGHT PERCENT, THE TOTAL AVERAGE MOLECULAR WEIGHT OF THE BLOCK POLYMER IS FROM 16,000 TO 20,000 AND THE GEL COMPOSITION COMPRISES FROM 15 TO 50 WEIGHT PERCENT OF THE COPOLYMER, ALL PARTS BY WEIGHT BEING BASED ON 100 PARTS BY WEIGHT OF SAID GEL COMPOSITION.
Claim 33
Dependent Claim
141 words
WHEN A IN FORMULA 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 4000, THEN THE ETHYLENE OXIDE CONTENT IS FROM 35 TO 90 WEIGHT PERCENT OF THE COPOLYMER, THE TOTAL AVERAGE MOLECULAR WEIGHT OF THE COPOLYMER IS FROM 6150 TO 2000 AND THE GEL COMPOSITION COMPRISES FROM 30 TO 50 WEIGHT PERCENT OF THE COPOLYMER, WITH THE FURTHER PROVISO THAT WHEN A IN FORMULA 1 IS AN INTEGER SUCH THAT THE AVERAGE MOLECULAR WEIGHT OF THE HYDROPHOBE IS ABOUT 4000, THE ETHYLENE OXIDE CONTENT IS FROM 70 TO 90 WEIGHT PERCENT, THE TOTAL AVERAGE MOLECULAR WEIGHT OF THE BLOCK POLYMER IS FROM 16,000 TO 20,000 AND THE GEL COMPOSITION COMPRISES FROM 15 TO 50 WEIGHT PERCENT OF THE COPOLYMER, ALL PARTS BY WEIGHT BEING BASED ON 100 PARTS BY WEIGHT OF SAID GEL COMPOSITION.
Claim 34
Dependent Claim
36 words
The method of claim 2 wherein the polyoxyethylene polyoxypropylene block copolymer has an average molecular weight hydrophobe of 4000 and the hydrophile portion of the copolymer constitutes from 70 to 90 weight percent of the copolymer.
Claim 35
Dependent Claim
36 words
The method of claim 3 wherein the polyoxyethylene polyoxypropylene block copolymer has an average molecular weight hydrophobe of 4000 and the hydrophile portion of the copolymer constitutes from 70 to 90 weight percent of the copolymer.
Claim 36
Dependent Claim
26 words
The method of claim 1 wherein the water-insoluble ingredient is selected from the group consisting of N,N-diethyltoluamide, undecylenic acid, lauryl lactate, hexachlorophene, p-toluene sulfonamide and 8-hydroxyquinoline.
Claim 37
Dependent Claim
26 words
The method of claim 2 wherein the water-insoluble ingredient is selected from the group consisting of N,N-diethyltoluamide, undecylenic acid, lauryl lactate, hexachlorophene, p-toluene sulfonamide and 8-hydroxyquinoline.
Claim 38
Dependent Claim
26 words
The method of claim 3 wherein the water-insoluble ingredient is selected from the group consisting of N,N-diethyltoluamide, undecylenic acid, lauryl lactate, hexachlorophene, p-toluene sulfonamide and 8-hydroxyquinoline.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-02-17 | 1978-08-19 | 1979-02-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-02-17 | 1982-08-19 | 1983-02-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-02-17 | 1986-08-19 | 1987-02-18 | $7700.00 | Window Closed / Lapsed |