Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Patent
1996-03-29
1997-07-29
Lipman, Bernard
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
5253267, 5253771, 5253338, 525361, 525364, 525387, C08F 806
Patent
active
056523114
DESCRIPTION:
DESCRIPTION
EXAMPLES
Example 1
In a process in accord with the invention 1 part poly L-histidine (ex Sigma) was added to a solution of:
The pH of the mix was adjusted from approx. 7 to approx. 6 with hydrochloric acid (15% w/w) and the resultant mix heated to 60-65 deg. C (when all the solid dissolved) and held for 4 hours.
Testing with starch/potassium iodide paper indicated excess peroxide still present and the pH was found to have fallen to approx. 4.
The pale yellow solution was added, with agitation, to acetone (200 volumes) to precipitate a white solid which was filtered off, washed and dried.
The dried solid was redissolved in water (4.7 volumes) and the pH adjusted from approx. 5 to approx. 1-2 (with conc. hydrochloric acid) when a white, gelatinous precipitate formed. This was removed by filtration and the filtrate added, with agitation, to acetone (200 volumes) to re-precipitate the N-oxidised product, which was filtered, washed and dried.
Proton nmr analysis confirmed the product to be essentially 100% N-oxidised product.
Example 2
In a process in accord with the invention 10 parts poly 4-vinylpyridine 10% solution in 50:50 t-butanol/water (ex Cassella(TM)) from the polymerisation process were added to a solution of:
The pH of the solution was adjusted from 7.1 to 5.4 (with conc. hydrochloric acid) and the mix refluxed for 2 hours when a pale yellow viscous oil separated. This was dissolved by the addition of a further 3.43 volumes of 30%w/v hydrogen peroxide solution and the mix was refluxed a further 2 hours.
After cooling the solution was added, with agitation, to acetone (200 volumes) when a viscous yellow syrup separated. The supernatant liquors were decanted and the syrup further treated with acetone to form a pale yellow solid, which was filtered, washed and dried in vacuo.
Proton nmr analysis indicated 80 mole% N-oxidised product.
Example 3
In a process in accord with the invention 1 part poly 4-vinylpyridine (solid ex Cassella(TM)) was added to a solution of:
The mix was held at 60-65 deg C for 4 hours then allowed to cool before adding to acetone (200 volumes) to precipitate a pale yellow solid. The solid was isolated by filtration, washed with acetone and dried under vacuum.
Proton nmr analysis indicated >90 mole% N-oxidised product.
Example 4
In a process in accord with the invention a solution of: Merck(TM))
The mix was heated to 60-65 deg C when the solid dissolved to form a red solution of pH approximately 6-7.
After 1.5 hours at 60-65 deg C the red colour had faded to pale yellow and a further aliquot (2.86 volumes) of hydrogen peroxide solution was added.
Further aliquots (2.86 volumes each) of hydrogen peroxide solution were required after another 45 minutes, then another 60 minutes to regenerate the reddish colour.
After a total of 4.25 hours at 60-65 deg C in the presence of the red species, the solution (pH approximately 6) was cooled and added, with agitation, to acetone (150 volumes). The supernatant liquors were decanted and the residual yellow sticky solid was re-slurried in acetone, gravity filtered, washed with acetone and dried in vacuo.
270 MHz proton nmr analysis indicated 81 mole % yield of N-oxidised product.
1. A process for the N-oxidation of polyamine polymers comprising treating said polyamine polymers with an effective amount of hydrogen peroxide in an aqueous or partly aqueous solution in the presence of heavy metal ion sequestrant and a catalytic amount of metal oxide catalyst selected from tungstate, molybdate and vanadate.
2. A process according to claim 1 wherein said polyamine polymers contain units having the following structural formula: ##STR1## wherein P is a polymerisable unit, whereto the oxidisable N atom can be attached, or wherein the oxidisable N atom forms part of, the polymerisable unit. ##STR2## x is or 0 or 1; R are aliphatic, ethoxylated aliphatic, aromatic, heterocyclic or alicyclic groups whereto the oxidisable N atom can be attached, or wherein the oxidisable N atom is part of, these groups.
3. A process according to claim 1 wherein
REFERENCES:
patent: 4111856 (1978-09-01), Haag et al.
patent: 4137386 (1979-01-01), Smith
patent: 5059659 (1991-10-01), Gregor et al.
patent: 5064912 (1991-11-01), Cheng et al.
Hardy Frederick Edward
Rowland Geoffrey William
Willey Alan David
Aylor Robert B.
Lipman Bernard
The Procter & Gamble & Company
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