US3557248A - Process for weakening the hydrophobic behavior of alkene polymers - Google Patents
Process for weakening the hydrophobic behavior of alkene polymers Download PDFInfo
- Publication number
- US3557248A US3557248A US745336A US3557248DA US3557248A US 3557248 A US3557248 A US 3557248A US 745336 A US745336 A US 745336A US 3557248D A US3557248D A US 3557248DA US 3557248 A US3557248 A US 3557248A
- Authority
- US
- United States
- Prior art keywords
- amide
- carbon atoms
- weight
- weakening
- alkene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title abstract description 20
- 150000001336 alkenes Chemical class 0.000 title abstract description 16
- 238000000034 method Methods 0.000 title abstract description 11
- 230000002209 hydrophobic effect Effects 0.000 title abstract description 10
- 230000003313 weakening effect Effects 0.000 title abstract description 6
- 150000001408 amides Chemical class 0.000 abstract description 14
- 229920001577 copolymer Polymers 0.000 abstract description 11
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 229960000935 dehydrated alcohol Drugs 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 10
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 6
- -1 lauric- Chemical group 0.000 description 6
- 150000004671 saturated fatty acids Chemical class 0.000 description 6
- 229940035044 sorbitan monolaurate Drugs 0.000 description 6
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical class OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
Definitions
- the present invention aims at an improved process for weakening the hydrophobic behavior of polymers and copolymers of alkenes.
- Another object of the invention is to provide a transparent packaging film made of such polymers.
- the process according to the invention for weakening the hydrophobic character of alkene polymers is characterized in that a polymer, or copolymer, of an alkene is mixed with (a) a 0.05-2% by weight of monester, or a diester, of a hexavalent, partly dehydrated alcohol, and an aliphatic carboxylic acid with 12-22 carbon atoms, and (b) 0.01-0.5% by weight of an amide of an aliphatic carboxylic acid with 12-22 carbon atoms.
- esters include esters of partly dehydrated hexitols, such as mannitan and sorbitan with saturated and unsaturated fatty acids, such as lauric acid, steric acid, oleic acid and erucic acid. Preference is given to the mono-esters, particularly to those of mannitan and sorbitan and a saturated fatty acid.
- Suitable carboxylic acids are both the amids of saturated and unsaturated fatty acids with 12-22 carbon atoms, such as lauric-, palmitic-, stean'c-, oleicand erucic acid-amide.
- the amide of oleic acid is particularly suitable.
- the esters are used in amounts of 0.05-2% by weight preferably 0.2-0.5 by weight, calculated to the amount of polymer. It is preferred to take the amounts of carboxylic acid amide smaller than the amount of ester, more specifically between 0.01 and 0.5% by weight, and preferably between 0.03 and 0.1% by weight, calculated to the amount of polymer.
- the process according to the invention can be used with homopolymers and copolymers of alkenes, for example polyethylene, polypropylene, poly-(4-methylpentene-1), copolymers of ethylene and propylene with one another or with some other alkene, such as butylene-l, pentylene-l, hexylene-l and octylene-l and copolymers of alkenes with other unsaturated compounds e.g. copolymers of ethylene with unstaurated esters such as vinylacetate and methylacrylate.
- alkenes for example polyethylene, polypropylene, poly-(4-methylpentene-1
- copolymers of ethylene and propylene with one another or with some other alkene such as butylene-l, pentylene-l, hexylene-l and octylene-l
- copolymers of alkenes with other unsaturated compounds e.g. copolymers of ethylene
- esters and the amides with the alkene polymers does not give any difficulties and can be done in a known manner, e.g. in mixing or kneading installations.
- the ester and the amides can be used in combination with other additives normally used with polyalkenes, e.g. dyes, fillers, antioxydants, antistatics, anti-blocking agents, such as silica and silicates, etc.
- the mixtures prepared according to the invention can by means of the procedures known in the art, be manufactured into transparent objects, eg, injection-molded articles, bottles and stretched or unstretched flat films, or blown films, having a less hydrophobic character than objects made of polyalkenes that do not contain the additives used according to the invention. Said mixtures can also be applied as film or coating on other materials, for instance on paper. The mixtures are, of course, also suited for production of non-transparent objects with a reduced hydrophobic behavior.
- 12-18 carbon atoms is sorbitanmonolaurate and the amide of an unsaturated fatty acid with 18-22 carbon atoms is oleic acid amde.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paper (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6709859A NL6709859A (enrdf_load_stackoverflow) | 1967-07-14 | 1967-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3557248A true US3557248A (en) | 1971-01-19 |
Family
ID=19800721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US745336A Expired - Lifetime US3557248A (en) | 1967-07-14 | 1968-07-12 | Process for weakening the hydrophobic behavior of alkene polymers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3557248A (enrdf_load_stackoverflow) |
| AT (1) | AT288015B (enrdf_load_stackoverflow) |
| BE (1) | BE718059A (enrdf_load_stackoverflow) |
| CH (1) | CH491970A (enrdf_load_stackoverflow) |
| DE (1) | DE1769782A1 (enrdf_load_stackoverflow) |
| ES (1) | ES356133A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1572001A (enrdf_load_stackoverflow) |
| GB (1) | GB1190542A (enrdf_load_stackoverflow) |
| NL (1) | NL6709859A (enrdf_load_stackoverflow) |
| SE (1) | SE349312B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929699A (en) * | 1970-01-29 | 1975-12-30 | Pvo International Inc | Fog resistant polymer compositions |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2808157A1 (de) * | 1978-02-25 | 1979-09-06 | Hoechst Ag | Dispergierbare zubereitung von fluorcarbonharzen |
| WO1984000553A1 (en) * | 1982-07-26 | 1984-02-16 | Dow Chemical Co | Olefin polymer barrier films and methods for use therefor |
-
1967
- 1967-07-14 NL NL6709859A patent/NL6709859A/xx unknown
-
1968
- 1968-07-10 GB GB32955/68A patent/GB1190542A/en not_active Expired
- 1968-07-11 CH CH1034168A patent/CH491970A/de not_active IP Right Cessation
- 1968-07-11 AT AT672268A patent/AT288015B/de not_active IP Right Cessation
- 1968-07-12 SE SE09668/68A patent/SE349312B/xx unknown
- 1968-07-12 BE BE718059D patent/BE718059A/xx unknown
- 1968-07-12 FR FR1572001D patent/FR1572001A/fr not_active Expired
- 1968-07-12 US US745336A patent/US3557248A/en not_active Expired - Lifetime
- 1968-07-12 DE DE19681769782 patent/DE1769782A1/de active Pending
- 1968-07-12 ES ES356133A patent/ES356133A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929699A (en) * | 1970-01-29 | 1975-12-30 | Pvo International Inc | Fog resistant polymer compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1769782A1 (de) | 1971-10-07 |
| SE349312B (enrdf_load_stackoverflow) | 1972-09-25 |
| AT288015B (de) | 1971-02-25 |
| FR1572001A (enrdf_load_stackoverflow) | 1969-06-20 |
| NL6709859A (enrdf_load_stackoverflow) | 1969-01-16 |
| GB1190542A (en) | 1970-05-06 |
| CH491970A (de) | 1970-06-15 |
| ES356133A1 (es) | 1970-01-01 |
| BE718059A (enrdf_load_stackoverflow) | 1969-01-13 |
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