US3896086A
Expired / Lapsed
US
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Process for the preparation of biodegradable polycarboxylates
Assignee: Evonik Operations GmbH
•
Filing: 1974-06-05
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Granted: 1975-07-22
•
Expires: 1994-06-05
Abstract
Abstract Acrolein together with acrylic acid as an optional reactant is polymerized in a heated, moving aqueous hydrogen peroxide solution by gradually adding monomers and n-dodecyl mercaptan to the solution. The resultant polymer exhibits improved biological degradability making it especially useful in detergents.
Inventors
- 👤 Heinz Haschke
- 👤 Gerhard Morlock
- 👤 Wilfried Felber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:15
CPC Classifications
C; C08; C08G; C08G2/00; C08G2/30; C08F; C08F16/00; C08F16/36; C08G2/14; C08G2/18; C08G2/26; C11; C11D; C11D3/00; C11D3/16; C11D3/37; C11D3/3746; C11D3/3757; Y; Y10; Y10S; Y10S260/00; Y10S260/43
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
73 words
IN A PROCESS FOR THE PREPARATION OF AN IMPROVED BIOLOGICAL DEGRADABLE POLYCARBOXYLATE BY THE OXIDATIVE POLYMERIZATION OF ACROLEIN ALONE OR WITH ACRYLIC ACID, SAID PROCESS COMPRISING SLOWLY ADDING ACROLEIN MONOMER OR ACROLEIN-ACRYLIC ACID MONOMER MIXTURE TO A HEATED, MOVING AQUEOUS HYDROGEN PEROXIDE SOLUTION, THE IMPROVEMENT COMPRISING SLOWLY ADDING TO SAID PEROXIDE SOLUTION ABOUT 0.1 TO ABOUT 10% BY WEIGHT OF N-DODECYL MERCAPTAN, RELATED TO THE WEIGHT OF MONOMER OR MONOMER MIXTURE, DURING POLYMERIZATION.
Claim 2
Dependent Claim
73 words
IN A PROCESS FOR THE PREPARATION OF AN IMPROVED BIOLOGICAL DEGRADABLE POLYCARBOXYLATE BY THE OXIDATIVE POLYMERIZATION OF ACROLEIN ALONE OR WITH ACRYLIC ACID, SAID PROCESS COMPRISING SLOWLY ADDING ACROLEIN MONOMER OR ACROLEIN-ACRYLIC ACID MONOMER MIXTURE TO A HEATED, MOVING AQUEOUS HYDROGEN PEROXIDE SOLUTION, THE IMPROVEMENT COMPRISING SLOWLY ADDING TO SAID PEROXIDE SOLUTION ABOUT 0.1 TO ABOUT 10% BY WEIGHT OF N-DODECYL MERCAPTAN, RELATED TO THE WEIGHT OF MONOMER OR MONOMER MIXTURE, DURING POLYMERIZATION.
Claim 3
Dependent Claim
27 words
Process according to claim 1 in which the addition of the n-dodecyl mercaptan is started and completed simultaneously with the addition of the monomer or monomer mixture.
Claim 4
Dependent Claim
50 words
Process according to claim 1 in which the addition of the n-dodecyl mercaptan begins about 0.1 to 2 hours after the beginning of the addition of the monomer or monomer mixture and ends up to about 3 hours after the completion of the addition of the monomer or monomer mixture.
Claim 5
Dependent Claim
29 words
Process according to claim 1 in which the rate of addition of the n-dodecyl mercaptan is increased during the course of its addition to the moving hydrogen peroxide solution.
Claim 6
Dependent Claim
29 words
Process according to claim 2 in which the rate of addition of the N-dodecyl mercaptan is increased during the course of its addition to the moving hydrogen peroxide solution.
Claim 7
Dependent Claim
29 words
Process according to claim 3 in which the rate of addition of the n-dodecyl mercaptan is increased during the course of its addition to the moving hydrogen peroxide solution.
Claim 8
Dependent Claim
19 words
Process according to claim 1 in which the monomer mixture comprises up to about 50 mole % acrylic acid.
Claim 9
Dependent Claim
20 words
Process according to claim 7 in which the monomer mixture comprises about 10 to about 30 mole % acrylic acid.
Claim 10
Dependent Claim
19 words
Process according to claim 1 in which the solution comprises about 15 to about 25% by weight hydrogen peroxide.
Claim 11
Dependent Claim
17 words
Process according to claim 1 in which the solution is heated at about 50* to about 100*C.
Claim 12
Dependent Claim
17 words
Process according to claim 1 in which the solution is heated at about 55* to about 85*C.
Claim 13
Dependent Claim
33 words
Process according to claim 1 in which the acrolein and hydrogen peroxide are present in an amount such that there are about 1.0 to 1.2 moles of acrolein per mole of hydrogen peroxide.
Claim 14
Dependent Claim
23 words
Process according to claim 1 in which the monomer or monomer mixture is added within a time of up to about 7 hours.
Claim 15
Dependent Claim
24 words
Process according to claim 1 in which the monomer or monomer mixture is added over a period of about 3 to about 5 hours.
Claim 16
Dependent Claim
22 words
Process according to claim 1 in which the n-dodecyl mercaptan is in an amount of about 0.5 to about 5% by weight.
Claim 17
Dependent Claim
23 words
Process according to claim 1 in which the n-dodecyl mercaptan is employed in an amount of about 0.5 to about 2% by weight.
Claim 18
Dependent Claim
16 words
Process according to claim 1 in which the resulting polymerizate is subsequently subjected to Cannizzaro reaction.
Claim 19
Dependent Claim
16 words
Process according to claim 17 in which the polymerizate is neutralized with an alkali metal hydroxide.
Claim 20
Dependent Claim
22 words
Process according to claim 1 in which the n-dodecyl mercaptan is added over a period of about 3 to about 5 hours.
Claim 21
Dependent Claim
32 words
Process according to claim 1 in which the addition of the n-dodecyl mercaptan begins about 0.5 to about 1.5 hours after the beginning of the addition of the monomer or monomer mixture.
Claim 22
Dependent Claim
43 words
Process according to claim 1 in which the addition of the n-dodecyl mercaptan is completed simultaneously with the addition of the monomer or monomer mixture or up to about 3 hours after the completion of the addition of the monomer or monomer mixture.
Claim 23
Dependent Claim
34 words
Process according to claim 21 in which the addition of the n-dodecyl mercaptan is completed within about 0.5 to about 1.5 hours after the completion of the addition of the monomer or monomer mixture.
Claim 24
Dependent Claim
35 words
Process according to claim 1 in which the rate of addition of the n-dodecyl mercaptan, expressed as % per hour of the total amount to be added, is about 1 to about 40% per hour.
Claim 25
Dependent Claim
23 words
Process according to claim 23 in which the rate of addItion of the n-dodecyl mercaptan is about 1 to about 10% per hour.
Claim 26
Dependent Claim
66 words
Process according to claim 24 in which the rate of addition of the n-dodecyl mercaptan is initially about 1 to about 5% per hour, and the rate of addition is gradually increased so that after the 3rd hour after the beginning of the addition of the monomer or monomer mixture, up to about 30% of the total quantity of mercaptan to be added has been added.
Claim 27
Dependent Claim
27 words
Process according to claim 1 in which the monomer or monomer mixture contains up to about 500 ppm of a stabilizer which will retard spontaneous radical polymerization.
Claim 28
Dependent Claim
16 words
Process according to claim 26 in which the stabilizer is a hydroquinone or a hydroquinone ether.
Claim 29
Dependent Claim
13 words
Process according to claim 27 in which the stabilizer is hydroquinone monomethyl ether.
Claim 30
Dependent Claim
23 words
Process according to claim 1 in which a lower alcohol or silicone-based defoaming agent is employed during polymerization in order to decrease foaming.
Claim 31
Dependent Claim
14 words
Process according to claim 18 in which the alkali metal is sodium or potassium.
Claim 32
Dependent Claim
53 words
Process according to claim 1 in which, after at least about 80% of the monomer or monomer mixture has been added, water is added to the hydrogen peroxide solution in an amount sufficient to yield an about 20 to about 40% weight (aldehydo carboxylic acid) solution at the end of the polymerization reaction.
Claim 33
Dependent Claim
56 words
Process according to claim 1 in which the resulting polymerizate is subsequently subjected to Cannizzaro reaction in a dilute solution of the resulting polymerizate or a dilute alkali metal hydroxide solution or by a slow addition of alkali metal hydroxide to an agitated solution of the resulting polymerizate in order to avoid localized condensation to aldols.
Claim 34
Dependent Claim
17 words
Process according to claim 32 in which Cannizzaro reaction is carried out in the presence of formaldehyde.
Claim 35
Dependent Claim
32 words
Process according to claim 1 in which, after completion of the additon of the monomers, the aqueous solution is stirred for up to about 12 hours at about 40* to about 90*C.
Claim 36
Dependent Claim
25 words
Process according to claim 34 in which said stirring is conducted at about 50* to about 75*C after completion of the addition of the monomers.
Claim 37
Dependent Claim
19 words
Process according to claim 1 in which unreacted monomers are removed from the solution by distillation or film evaporation.
Claim 38
Dependent Claim
26 words
Process according to claim 36 in which distillation is conducted at reduced pressure and about 10 to about 40% by volume of the solution is removed.
References Cited (Backward Citations)
US3141864A
Cited
US3686145A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-07-21 | 1979-01-20 | 1979-07-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-07-21 | 1983-01-20 | 1983-07-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-07-21 | 1987-01-20 | 1987-07-22 | $7700.00 | Window Closed / Lapsed |