Lubricious Condoms

Abstract

This invention disclosed condoms with surface hydrophilic and lubricious modification. Said condoms were grafted with a thin layer of zwitterions, which forms lubricious water layer when contacted with human body liquids or other water solutions, to lower the surface friction and mechanical damage to human body, and to improve user's experience. Another benefit of present invention is due to the tight bonding between modification material and condom substrate, the modification will stably stay on the substrate during usage, to avoid the potential side effects caused by lubricants.

Claims

1. Condoms with surface hydrophilic and lubricous modifications; said condoms was grafted with zwitterions which form lubricious water film in liquid environment to lower the surface friction.

2. The condoms of claim 1, where the monomers of zwitterions have the following structure:
B-L-Z in which B was chosen from: ##STR00003## Wherein: R is hydrogen, alkyl or substituted alkyl. L doesn't exist, or is linear or branch alkyl, optionally with one or more carbon atoms replaced by oxygen atoms; Z is a zwitterion, which can be chosen from: ##STR00004## R1 is hydrogen, alkyl, or substituted alkyl. R2 and R3 are independent, and are hydrogen, alkyl, or substituted alkyl. m is integer from 1 to 7.

3. The condoms in claim 2, where the zwitterions include one or more monomers.

4. The condoms in claim 2, where the zwitterions are phosphocholines.

5. The condoms in claim 2, where the zwitterions are betaines.

6. The condoms in claim 2, where the condom substrate material is latex.

7. The condoms in claim 2, where the condom substrate material is polyurethane.

8. The condoms in claim 2, where the condoms are made from natural materials such as animal intestines.

9. The condoms in claim 5, where the zwitterions are carboxybetaines.

10. The condoms in claim 5, where the zwitterions are sulfobetaines.

Description

EXAMPLES

Example 1 Lubricious Condoms by ATRP Method

[0039] Step 1: 100 gram of N,N-dimethylaminoethyl methacrylate was dissolved into 1000 ml of glacial acetic acid. 40 gram of ethenesulfonyl chloride was slowly added into the solution, which was then stirred at room temperature for 24 hours. The precipitate was collected, washed in anhydrous ethanol twice, and then ground into powder after drying.

[0040] Step 2: Polyurethane condoms were first treated with chlorine plasma, and then added into 100 ml of 1:1 (v:v) methanol aqueous solution, which contained of 10 mM of CuCl.sub.2, 20 mM of N,N,N,N,N-pentamethyldiethylenetriamine, and 10% (w/v) of the product from Step 1. After sealing, samples and solution were purged with nitrogen for 15 minutes and then heated to 60 C. After 3 hours, the condoms were taken out, first washed with the mixture of methanol and water, then washed with physiological saline solution, and dried in air.

Example 2: Lubricious Condoms by UV Free Radical Polymerization

[0041] Step 1: 100 gram of N,N-dimethylaminoethyl methacrylate was dissolved into 1000 ml of acetonitrile. Then 80 gram of 1,4-butanesultone and 300 mg of 1,3-dinitrobenzene were slowly added to the solution, which was refluxed at room temperature for 24 hours. The precipitate was collected, washed twice in acetonitrile, and dried at room temperature.

[0042] Step 2: Latex condoms were washed and cleaned, then immersed in 100 ml of 0.1 M benzophenone in ethanol for 60 minutes. After drying in air, samples were put in 100 ml of 10% (w/v) solution of the product from Step 1 in water, which was then purged with nitrogen for 15 minutes and reacted in UV rotation reactor for 6 hours. Condoms were then taken out, rinsed with saline, and dried in air.

Example 3: Lubricious Condoms by Heat Free Radical Polymerization

[0043] Step 1: 100 gram of N,N-dimethylaminoethyl methacrylate was dissolved into 600 ml of anhydrous acetone. 55 gram of -propiolactone was slowly added into the solution and then reacted under nitrogen at 15 C. for 6 hours. The precipitate was collected, washed with anhydrous acetone twice, dried, and then ground into powder.

[0044] Step 2: Latex condoms were first immersed into 100 ml of 1% (w/v) azobisisobutyronitrile in ethanol for 60 minutes, dried in air, and then put into 100 ml of 10% (w/v) solution of product from Step 1 and 1 mM of FeCl.sub.2. After purging with nitrogen for 15 minutes, the solution was heated to 80 C. and reacted for 3 hours. Then the condoms were taken out, washed with saline, and dried.

Example 4: Lubricous Condoms by Redox Free Radical Polymerization

[0045] Step 1: 100 gram of N,N-dimethylaminoethyl methacrylate was added into 400 ml of anhydrous acetone, and 75 gram of 1,3-propanesultone was dissolved into 100 ml of anhydrous acetone. The two solutions were slowly mixed together, stirred at room temperature for 4 hours, and left at room temperature for 7 days. Then the precipitate was collected, washed with anhydrous acetone and dried.

[0046] Step 2: Latex condoms were immersed in 100 ml of 1% (w/v) tert-butyl hydroperoxide in methanol for 60 minutes, dried in air, and then put into 100 ml of 10/% (w/v) solution of the product from Step 1 and 1 mg/ml of diammonium cerium(IV) nitrate in water. After purging with nitrogen for 15 minutes, the solution was heated to 60 C. and reacted for 3 hours. Then the condoms were taken out, washed with saline and water, and dried.

Example 5: Mechanical Testing for Lubricious Condoms

[0047] Condoms were tested following ISO 4074:2015 natural rubber latex male condomsrequirements and test methods, which includes the size, thickness, pinholes, aging, and strength. Compared to unmodified controls, lubricious condoms had thickness increase less than 0.5 m, and there was no statistically significant change for other parameters.

Example 6: The Measurement of Surface Friction Coefficient

[0048] To measure the surface friction coefficient of control and modified condoms, ASTM standard D189414 Standard Test Method for Static and Kinetic Coefficients of Friction of Plastic Film and Sheeting was referenced with modification. In details, condoms were put on stainless steel mandrels, kept flat, and contacted with the mandrel surface as much as possible. Then condoms together with the mandrels were put into saline, perpendicularly mounted, and a 2 N force was applied through a par of forceps. The friction coefficient measuring machine has a range from 0 to 5 N, with an accuracy higher than 0.2%. When the samples moved in a rate of 150 mm/min, the kinetic friction coefficient was measured. The results showed that control samples had friction coefficient higher than 0.5, while that of the modified ones lower than 0.05.

Example 7: The Stability of Condom Surface Modification

[0049] ASTM D6279-15 Standard Test Method for Rub Abrasion Mar Resistance of High Gloss Coatings was referenced for the condom surface modification stability testing. In details, condoms were mounted on stainless mandrels, immersed into silane, hold with hands, and moved hands up and down with a relatively constant rate about 15 cm/min. One back and forth is a testing circle and 1000 such circles were tested, and then surface friction coefficient was measured again following the steps in example 6. It has been found that the surface friction coefficient didn't have any statistically significant change, which proved that the surface modification was mechanically stable.

Example 8: Aging of Modified Condoms

[0050] Modified condoms were sealed and then kept at 70 C. for 7 days. Then the surface friction coefficient was measured following the steps in example 6. It has been found that the surface friction coefficient didn't have any statistically significant change, which met the aging requirement for ISO 4074:2015 Natural rubber latex male condomsRequirements and test methods.