HULSHOF HENRICUS JOZEF MARIA (NL)
| WO1998021547A1 | 1998-05-22 | |||
| WO1979000320A1 | 1979-06-14 |
| EP0603062A1 | 1994-06-22 | |||
| DE3631187A1 | 1988-03-24 |
PATENT ABSTRACTS OF JAPAN vol. 6, no. 221 (P - 153)<1099> 5 November 1982 (1982-11-05)
| 1. | A method for producing a substantially odorless solution of an aminogroupcontaining polymer such as a terpolymer of vinyl pyrrolidone, vinyl caprolactam and dimethylaminoethyl methacrylate, a copolymer of vinyl pyrrolidone and (3methacryl amidopropyl) trimethylammonium chloride, and a cpolymer of vinyl pyrrolidone and acrylamidopropyl trimethylammonium chloride which comprises treating a solution of said polymer with 0.110% by weight of an acidic compound, or an acidic ionexchange resin, preferably at about 2070°C. for about 15 minutes to about 24 hours. |
| 2. | A method according to claim 1 wherein the treated terpolymer or copolymer solution is filtered to remove any insoluble material therein. |
| 3. | A method according to claim 1 wherein said terpolymer or copolymer solution is an aqueous, an organicalcoholic, or an aqueousalcoholic solution of the terpolymer. |
| 4. | A method according to claim 1 wherein said acid is ptoluenesulfonic acid, salicylic acid, citric acid, or a crosslinked polyacrylic acid. |
| 5. | A method according to claim 1 wherein said treatment is carried out by passing the terpolymer or copolymer solution through an acidic ionexchange resin. |
Lorenz, in U.S. Patent 4,521,404 described a polymeric hair preparation using a terpolymer of vinyl pyrrolidone (VP) , vinyl caprolactam (VC) and dimethylaminoethyl methacrylate (DMAEMA) . However, often such products are plagued by an objectionable odor which limit their usefulness in the cosmetic and personal care industry.
Other commercial polymer solutions, such as copolymers of VP and (3-methacrylamidopropyl) trimethylammonium chloride (MAPTAC) , or acrylamidopropyl trimethylammonium chloride, also have odor problems.
A process is provided herein for treating a solution of an amino-group-containing polymer, e.g. vinyl pyrrolidone-containing polymers, which have objectional odors, with 0.1-10% by weight of an acidic compound, or an acidic ion-exchange resin, at 20-70°C. for about 15 minutes to 24 hours, to render the polymer product substantially odorless.
The terpolymer solution may be an aqueous, an organic-alcoholic, or an aqueous-alcoholic solution of the terpolymer. Treatment may be effected with an acid which is soluble in, or insoluble in the polymer solution, and the treated solution may be filtered to remove any insoluble material therein.
EXAMPLE 1
A sample of an aqueous-alcoholic solution of the Lorenz terpolymer had a strong, unpleasant, musty odor. Several acidic compounds were added to this terpolymer product at a 10% w/w ratio. The treated samples were evaluated for odor after various time intervals. The results are shown in the Table below.
TABLE
Odor Odor
Acidic Compound (next day) (1 year later) Salicylic acid** Odorless Odorless Citric acid Odorless Odorless Carbopol 1342* Odorless Odorless p-Toluenesulfonic acid Substantially Substantially Odorless Odorless
Dowex 50 -X8,H + ** Odorless Odorless
* Crosslinked polyacrylic acid
** In homogeneous system, can be easily decanted or filtered
EXAMPLE 2
The procedure of Example 1 was followed using an aqueous copolymer solution of vinyl pyrrolidone and (3-methacrylamidopropyl) trimethylammonium chloride which had an objectionable odor initially, but, after treatment, was substantially odorless.
EXAMPLE 3
The procedure of Example 1 was followed using an alcoholic copolymer solution of acrylamidopropyl trimethylammonium chloride with similar results.
EXAMPLE 4
A pressure filter was filled with Dowex 50 X 8- 100 sulfonic acid ion-exchange resin and connected to a 20 psi N 2 line. Then a mixture of 10 ml of the resin and 100 ml of a commercial sample of the Lorenz polymer in solution having a strong odor was passed through the filter bed over a period of about 15-20 minutes (a) at room temperature, and (b) at 60 β C. The thus-treated solutions then were observed to be substantially free of any odor as a result of contact with the acidic resin; and treatment of the terpolymer solution at room temperature gave a product which was completely odor- free.