US4196111A
Expired / Lapsed
US
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Chemically reducing residual acrylonitrile monomer in nitrile polymers and shaped packaging materials formed therefrom
Assignee: Bayer Antwerpen NV
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Filing: 1978-11-06
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Granted: 1980-04-01
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Expires: 1998-11-06
Abstract
Abstract A process for reducing free acrylonitrile monomer in nitrile copolymers during melting which involves having an effective amount of an acrylonitrile scavenger selected from the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol with a fatty acid or cyanuric acid in admixture with the copolymer during melting. Shaped products such as pellets, preforms, containers, film, sheet, etc., formed from such melt are well suited for packaging food, beverages, pharmaceuticals, cosmetics, etc., in that residual acrylonitrile monomer in the walls of such products is reduced over that present in the absence of such a scavenger.
Inventors
- 👤 I. Luis Gomez
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 11:54
CPC Classifications
B; B29; B29C; B29C49/00; B29C49/0005; C; C08; C08F; C08F6/00; C08F6/006; B29C2949/00; B29C2949/20; B29C2949/22; B29C2949/24; B29C2949/26; B29C2949/28; B29C2949/30; B29C2949/3024; B29C2949/3032
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
83 words
In the process of melting acrylonitrile copolymer by physical working while generating free acrylonitrile monomer in the melt, the improvement which comprises having a scavenging amount of a compound selected from the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid in admixture with the copolymer during said melting to minimize the level of free acrylonitrile monomer in the copolymer.
Claim 2
Dependent Claim
83 words
In the process of melting acrylonitrile copolymer by physical working while generating free acrylonitrile monomer in the melt, the improvement which comprises having a scavenging amount of a compound selected from the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid in admixture with the copolymer during said melting to minimize the level of free acrylonitrile monomer in the copolymer.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein said unsaturated fatty acid aldehyde is citral.
Claim 4
Dependent Claim
11 words
The process of claim 1 wherein said ester is vinyl stearate.
Claim 5
Dependent Claim
12 words
The process of claim 1 wherein said ester is tri allyl cyanurate.
Claim 6
Dependent Claim
21 words
The process of claims 1, 2, 3 or 4 wherein the copolymer comprises at least about 50 weight percent polymerized acrylonitrile.
Claim 7
Dependent Claim
19 words
The process of claim 5 wherein said physical working is accomplished by masticating the polymer in a plasticizing zone.
Claim 8
Dependent Claim
20 words
The process of claim 5 wherein the nitrile copolymer and scavenging compound are dry blended together before said physical working.
Claim 9
Dependent Claim
29 words
The process of claim 5 wherein the amount of scavenging compound is in the range of about 0.005 to about 2% based on the weight of the nitrile copolymer.
Claim 10
Dependent Claim
15 words
The process of claims 5 wherein the nitrile copolymer contains styrene as a copolymerized monomer.
Claim 11
Dependent Claim
21 words
The process of claim 6 wherein the copolymer is masticated in a plasticizing zone comprising a screw rotating within a barrel.
Claim 12
Dependent Claim
10 words
The process of claim 10 wherein the screw axially reciprocates.
Claim 13
Independent Claim
105 words
A method for reducing the content of free acrylonitrile monomer in shaped packaging materials formed of an acrylonitrile copolymer which comprises having a scavenging concentration of a compound selected from the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid in intimate contact with the copolymer during at least one forming operation in which the copolymer is heated to form a melt and shaped so that a packaging material is obtained with free acrylonitrile monomer content of less than about 7 ppm.
Claim 14
Independent Claim
105 words
A method for reducing the content of free acrylonitrile monomer in shaped packaging materials formed of an acrylonitrile copolymer which comprises having a scavenging concentration of a compound selected from the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid in intimate contact with the copolymer during at least one forming operation in which the copolymer is heated to form a melt and shaped so that a packaging material is obtained with free acrylonitrile monomer content of less than about 7 ppm.
Claim 15
Dependent Claim
13 words
The method of claim 12 wherein the forming operation includes an extrusion operation.
Claim 16
Dependent Claim
14 words
The method of claim 12 wherein the forming operation includes an injection molding operation.
Claim 17
Dependent Claim
14 words
The method of claim 12 wherein the forming operation includes a blow molding operation.
Claim 18
Dependent Claim
16 words
The method of claim 12 wherein the copolymer comprises at least 50 weight percent polymerized acrylonitrile.
Claim 19
Dependent Claim
11 words
The method of claim 13 further comprising a blow molding operation.
Claim 20
Dependent Claim
11 words
The method of claim 14 further comprising a blow molding operation.
Claim 21
Independent Claim
35 words
The method of claims 12, 13, 14, 15, 16, 17 or 18 wherein said acrylonitrile copolymer is in intimate contact with a member of the group consisting of vinyl stearate, citral or tri allyl cyanurate.
Claim 22
Dependent Claim
79 words
In the process for preparing shaped packaging materials from acrylonitrile copolymers, which process involves at least one forming operation comprising heating the copolymer to form a melt and shaping the copolymer, the improvement which comprises having citral or tri allyl cyanurate in intimate contact with the acrylonitrile copolymer during at least one forming operation, said citral or tri allyl cyanurate being employed in an amount sufficient to reduce the extractable free acrylonitrile monomer content of the resulting packaging material.
Claim 23
Dependent Claim
79 words
In the process for preparing shaped packaging materials from acrylonitrile copolymers, which process involves at least one forming operation comprising heating the copolymer to form a melt and shaping the copolymer, the improvement which comprises having citral or tri allyl cyanurate in intimate contact with the acrylonitrile copolymer during at least one forming operation, said citral or tri allyl cyanurate being employed in an amount sufficient to reduce the extractable free acrylonitrile monomer content of the resulting packaging material.
Claim 24
Dependent Claim
20 words
The process of claim 20 wherein the acrylonitrile copolymer comprises from about 55 to about 85 weight percent polymerized acrylonitrile.
Claim 25
Dependent Claim
98 words
A preform for conversion into a container for environmentally sensitive materials, said preform being formed of a thermoplastic material comprising at least about 10 weight percent of polymerized acrylonitrile monomer, the level of free acrylonitrile monomer in such preform being no greater than about 7 ppm based on the total weight of the polymer, the walls of such preform containing the reaction product of (i) unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid and (ii) acrylonitrile monomer.
Claim 26
Dependent Claim
98 words
A preform for conversion into a container for environmentally sensitive materials, said preform being formed of a thermoplastic material comprising at least about 10 weight percent of polymerized acrylonitrile monomer, the level of free acrylonitrile monomer in such preform being no greater than about 7 ppm based on the total weight of the polymer, the walls of such preform containing the reaction product of (i) unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid and (ii) acrylonitrile monomer.
Claim 27
Dependent Claim
20 words
The preform of claim 22 wherein the thermoplastic material comprises from about 50 to about 85 weight percent polymerized acrylonitrile.
Claim 28
Dependent Claim
8 words
The preform of claim 22 in tubular shape.
Claim 29
Dependent Claim
98 words
A shaped packaging material for environmentally sensitive products formed of a thermoplastic polymer comprising at least about 10 weight percent of polymerized acrylonitrile monomer, the level of free acrylonitrile monomer in said packaging material being no greater than about 7 ppm based on the total weight of the polymer, said packaging material containing the reaction product of (i) a member of the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid and (ii) acrylonitrile monomer.
Claim 30
Dependent Claim
98 words
A shaped packaging material for environmentally sensitive products formed of a thermoplastic polymer comprising at least about 10 weight percent of polymerized acrylonitrile monomer, the level of free acrylonitrile monomer in said packaging material being no greater than about 7 ppm based on the total weight of the polymer, said packaging material containing the reaction product of (i) a member of the group consisting of unsaturated fatty acid aldehydes, and esters formed by the reaction of a short chain olefinic alcohol containing two to four carbon atoms with a fatty acid or cyanuric acid and (ii) acrylonitrile monomer.
Claim 31
Dependent Claim
21 words
The packaging material of claim 25 wherein the thermoplastic resin comprises from about 50 to about 85 weight percent polymerized acrylonitrile.
Claim 32
Dependent Claim
12 words
The packaging material of claim 25 in the form of a film.
Claim 33
Dependent Claim
13 words
The packaging material of claim 25 including an environmentally sensitive substance packaged therein.
Claim 34
Dependent Claim
16 words
The packaging material of claims 25, 26 or 28 in the form of a self-supporting container.
Claim 35
Dependent Claim
8 words
Containers formed by the method of claim 12.
Claim 36
Dependent Claim
8 words
Films formed by the method of claim 12.
Claim 37
Dependent Claim
8 words
Bottles formed by the method of claim 12.
Claim 38
Dependent Claim
9 words
Self-supporting containers formed by the process of claim 20.
Claim 39
Dependent Claim
8 words
Films formed by the process of claim 20.
Claim 40
Dependent Claim
8 words
Bottles formed by the process of claim 20.
Claim 41
Dependent Claim
14 words
Environmentally sensitive substances packaged in the packaging materials of claims 30, 31 or 32.
Claim 42
Dependent Claim
14 words
Environmentally sensitive substances packaged in the packaging materials of claims 33, 34 or 35.
References Cited (Backward Citations)
US3863014A
Cited
US3900120A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-01 | 1983-10-01 | 1984-04-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-01 | 1987-10-01 | 1988-04-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-01 | 1991-10-01 | 1992-04-01 | $7700.00 | Window Closed / Lapsed |