NO140065B - USE OF CERTAIN UNSATURATED HYDROCARBONS TO PROMOTE THE DESTRUCTIVE EFFECT OF SUNLIGHT ON THERMO PLASTIC - Google Patents
USE OF CERTAIN UNSATURATED HYDROCARBONS TO PROMOTE THE DESTRUCTIVE EFFECT OF SUNLIGHT ON THERMO PLASTIC Download PDFInfo
- Publication number
- NO140065B NO140065B NO4946/73A NO494673A NO140065B NO 140065 B NO140065 B NO 140065B NO 4946/73 A NO4946/73 A NO 4946/73A NO 494673 A NO494673 A NO 494673A NO 140065 B NO140065 B NO 140065B
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- Prior art keywords
- degradation
- sunlight
- polymer
- exposed
- promote
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- 229920001169 thermoplastic Polymers 0.000 title claims description 3
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 3
- 230000001066 destructive effect Effects 0.000 title 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims description 20
- BOBLSBAZCVBABY-WPWUJOAOSA-N 1,6-diphenylhexatriene Chemical compound C=1C=CC=CC=1\C=C\C=C\C=C\C1=CC=CC=C1 BOBLSBAZCVBABY-WPWUJOAOSA-N 0.000 claims description 10
- 230000015556 catabolic process Effects 0.000 claims description 10
- 238000006731 degradation reaction Methods 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- -1 polyethylene Polymers 0.000 claims description 6
- 229910052724 xenon Inorganic materials 0.000 claims description 6
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004566 IR spectroscopy Methods 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- GQVMHMFBVWSSPF-SOYUKNQTSA-N (4E,6E)-2,6-dimethylocta-2,4,6-triene Chemical compound C\C=C(/C)\C=C\C=C(C)C GQVMHMFBVWSSPF-SOYUKNQTSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- GQVMHMFBVWSSPF-UHFFFAOYSA-N cis-alloocimene Natural products CC=C(C)C=CC=C(C)C GQVMHMFBVWSSPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000011888 foil Substances 0.000 claims description 2
- 229920001684 low density polyethylene Polymers 0.000 claims description 2
- 239000004702 low-density polyethylene Substances 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 claims 1
- DMCJFWXGXUEHFD-UHFFFAOYSA-N pentatriacontan-18-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)CCCCCCCCCCCCCCCCC DMCJFWXGXUEHFD-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical class O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229920006237 degradable polymer Polymers 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000018984 mastication Effects 0.000 description 1
- 238000010077 mastication Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000013502 plastic waste Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000002699 waste material Substances 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
- C08K5/01—Hydrocarbons
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)
- Graft Or Block Polymers (AREA)
- Table Devices Or Equipment (AREA)
- Moulding By Coating Moulds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Det er kjent at motstandsevnen mot atmosfærisk og mikrobiell nedbrytning, en faktor som fremmet anvendelsen av plast i em-ballasjeindustrien, har ført til at plastavfall samler seg opp i naturen. It is known that the resistance to atmospheric and microbial degradation, a factor that promoted the use of plastic in the packaging industry, has led to plastic waste accumulating in nature.
For å overvinne denne mangel er det foreslått en del løsninger To overcome this shortcoming, a number of solutions have been proposed
som f.eks. anvendelse av mer ustabile polymerer eller bruk av tilsetningsmidler som lar de vanlige polymerer undergå en foto-nedbrytningsreaksjon, selektivt iverksatt av de ultrafiolette stråler i solspekteret. like for example. the use of more unstable polymers or the use of additives that allow the usual polymers to undergo a photo-degradation reaction, selectively triggered by the ultraviolet rays in the solar spectrum.
For begrensede anvendelser innenfor landbruket er det foreslått For limited applications within agriculture, it is proposed
å anvende polybuten-1 og kopolymerer av buten-1, syndiotaktisk polybutadien-1,2 og kopolymerer av butadien-1,2. to use polybutene-1 and copolymers of butene-1, syndiotactic polybutadiene-1,2 and copolymers of butadiene-1,2.
For de plastmaterialer som nå er den hyppigste kilde for avfall, har imidlertid de kjente løsninger basert seg på innføring i polymeren, både ved kopolymerisering og som tilsetningsmidler, av grupper som er følsomme for lys i det nær ultrafiolette område, For the plastic materials that are now the most frequent source of waste, however, the known solutions have been based on the introduction of groups that are sensitive to light in the near-ultraviolet range into the polymer, both by copolymerization and as additives.
og som derved muliggjør foto-oksydasjonsreaksjoner når polymeren utsettes for sollys. (Se f.eks. BRD-off. skrift nr. 1.569.098). Det er også kjent å anvende styren-kopolymerer med vinylketon og karbonmono-oksyd, og kopolymerer av etylen og karbonmono-oksyd, and which thereby enable photo-oxidation reactions when the polymer is exposed to sunlight. (See e.g. BRD official document no. 1.569.098). It is also known to use styrene copolymers with vinyl ketone and carbon monoxide, and copolymers of ethylene and carbon monoxide,
se f.eks. BRD-off. skrift nr. 2.119.855. see e.g. BRD off. document no. 2,119,855.
Av tilsetningsmidler er det foreslått å anvende jern-dialkylditio-karbamater eller andre komplekser av overgangsmetallene, gamma-pyron-derivater, alkyl-, alkylaryl- og aryl-ketoner. (Se f.eks. US-patentskrift 3.676.401). Slike tilsetningsmidler har den mangel at de har merkbare selv-forsinkende fenomener, og at de videre undergår en merkbar aktivitetsnedsettelse når de alkyleres eller podes på polymeren for å redusere deres vandring. As additives, it has been proposed to use iron dialkyldithiocarbamates or other complexes of the transition metals, gamma-pyrone derivatives, alkyl, alkylaryl and aryl ketones. (See, for example, US Patent 3,676,401). Such additives have the disadvantage that they have noticeable self-delaying phenomena, and that they further undergo a noticeable decrease in activity when they are alkylated or grafted onto the polymer to reduce their migration.
Det er nå funnet at det er mulig å eliminere de nevnte mangler It has now been found that it is possible to eliminate the aforementioned defects
ved anvendelse av 1,6-difenyl-1,3,5-heksatrien og/eller 2,6-di-metyl-2,4,6-oktatrien som nedbrytningsfremmende tilsetning til termoplast, særlig folier og plater av polyetylen, polypropylen og etylen/vinylacetat-kopolymerer som forventes å bli utsatt for sollys. when using 1,6-diphenyl-1,3,5-hexatriene and/or 2,6-dimethyl-2,4,6-octatriene as a degradation-promoting additive for thermoplastics, in particular foils and sheets of polyethylene, polypropylene and ethylene /vinyl acetate copolymers expected to be exposed to sunlight.
Fremgangsmåten for fremstilling av de nedbrytbare polymerer går The process for producing the degradable polymers is as follows
ut på at det til plastmaterialet, som eventuelt inneholder vanlige tilsetningsmidler som antioksydasjonsmidler, mykningsmidler og antistatiske midler, tilsettes 1,6-difenyl-1,3,5-heksatrien (DPHT) og/eller 2,6-dimetyl-2,4,6-oktatrien. 1,6-diphenyl-1,3,5-hexatriene (DPHT) and/or 2,6-dimethyl-2,4, The 6-octatriene.
Det synes som de anvendte tilsetningsmidler er i stand til å fotoaktivere molekylært oksygen under innvirkning av sollyset. It seems that the additives used are capable of photoactivating molecular oxygen under the influence of sunlight.
Plastmaterialet tilsettes de ovennevnte umettede forbindelser i The above-mentioned unsaturated compounds are added to the plastic material
en mengde på opptil 3 vektprosent, foretrukket fra 0,1 til 1 vektprosent. an amount of up to 3% by weight, preferably from 0.1 to 1% by weight.
Tilsetningsmidlene kan innføres i polymeren på kjente måter som f.eks. pulverblanding og mastisering. Arbeidsbetingelsene frem-går klarere av de følgende eksempler som er gjengitt for bedre å illustrere oppfinnelsen. The additives can be introduced into the polymer in known ways such as e.g. powder mixing and mastication. The working conditions appear more clearly from the following examples which are reproduced to better illustrate the invention.
EKSEMPEL 1. EXAMPLE 1.
Handelsvanlig polyetylen med høy densitet, inneholdende små mengder antioksydasjonsmidler, antistatiske midler og andre vanlige be-standdeler, ble tilsatt 1,6-difenylheksatrien (DPHT), ved vanlig kjente metoder, i mengder på 0,1, 1 og 3 g pr. 100 g polymer. Filmene ble oppnådd ved smelting i en "CARVER"-presse, oppvarmet til 200°C, og det ble fremstilt prøver med ca. 0,02 cm tykkelse. Commercial high-density polyethylene, containing small amounts of antioxidants, antistatic agents and other common ingredients, was added with 1,6-diphenylhexatriene (DPHT), by commonly known methods, in amounts of 0.1, 1 and 3 g per 100 g of polymer. The films were obtained by melting in a "CARVER" press, heated to 200°C, and samples with approx. 0.02 cm thickness.
Disse filmer ble utsatt for bestråling med en xenon høytrykkslampe som viste en spektral energi-fordeling tilsvarende sollyset. These films were exposed to irradiation with a xenon high-pressure lamp which showed a spectral energy distribution corresponding to sunlight.
Nedbrytningshastigheten ble målt ved hjelp av infrarød spektro-skopi ved å måle området for bånd fra 5,65 til 6, karakteristiske for karboksylgrupper, hvis tilsynekomst i polymeren henger sammen med tapet av dens fysikalske og mekaniske egenskaper. For dette formål ble det tegnet opp en kalibreringskurve ved å anvende stearon som sammenligningsprøve, og det ble avtegnet CO-tall pr. gram polymer i forhold til forholdet mellom området av bånd fra 5,65 og 6 og filmtykkelsen. The rate of degradation was measured by infrared spectroscopy by measuring the range of bands from 5.65 to 6, characteristic of carboxyl groups, whose appearance in the polymer is associated with the loss of its physical and mechanical properties. For this purpose, a calibration curve was drawn up using stearone as a comparison sample, and the CO number per grams of polymer in relation to the ratio between the area of bands from 5.65 and 6 and the film thickness.
Under eksponeringen av filmene ble temperaturen holdt konstant på 29 - 32°C. During the exposure of the films, the temperature was kept constant at 29 - 32°C.
Den følgende tabell gjengir de resultater som ble oppnådd fra eksponeringene av både den behandlede og den ubehandlede polymer for bestrålingen fra xenon-lampen. The following table reproduces the results obtained from the exposures of both the treated and the untreated polymer to the irradiation from the xenon lamp.
De resultater som er gjengitt i tabellen viser den høyere nedbrytningshastighet for polymer tilsatt 1,6-difenylheksatrien. I det følgende gjengis smelteflyte-verdien MFI for en polymer med og uten tilsetning av DPHT. The results reproduced in the table show the higher degradation rate for polymer added with 1,6-diphenylhexatriene. In the following, the melt flow value MFI is given for a polymer with and without the addition of DPHT.
Man ser bare en ubetydelig virkning på viskositeten. One sees only an insignificant effect on the viscosity.
EKSEMPEL 2. EXAMPLE 2.
Handelsvanlig polyetylen med lav densitet, inneholdende små mengder av vanlige stabiliseringsmidler, ble tilsatt 1,6-difenylheksatrien i mengder på 0,1, 1 og 3 deler pr. 100 deler polymer. Commercial low-density polyethylene, containing small amounts of common stabilizers, was added to 1,6-diphenylhexatriene in amounts of 0.1, 1 and 3 parts per 100 parts polymer.
De oppnådde filmer ble eksponert for en xenon-lampe på samme måte i eksempel 1. The films obtained were exposed to a xenon lamp in the same manner as in Example 1.
Nedbrytningshastigheten ble fulgt ved I.R.-spektroskopi og ved hjelp av den metodikk som er beskrevet i det foregående eksempel. The rate of degradation was followed by I.R. spectroscopy and by means of the methodology described in the previous example.
De oppnådde resultater er gjengitt i følgende tabell. The results obtained are reproduced in the following table.
Også dette eksempel viser klart den høyere nedbrytningshastighe/t for polymerene som inneholdt 1,6-difenylheksatrien. This example also clearly shows the higher degradation rate/h for the polymers that contained 1,6-diphenylhexatriene.
EKSEMPEL 3. EXAMPLE 3.
Dette eksempel viser egenskapene for en handelsvanlig E/VAC-kopolymer med 2 vektprosent vinylacetat, en smelteflyteindeks på omtrent 1,1 og densitet 0,9268 ved 23°C, som var tilsatt 1,6-difenylheksatrien (1 g pr. 100 g polymer) og ble utsatt for bestråling fra en xenon-lampe. This example shows the properties of a commercial E/VAC copolymer with 2% by weight vinyl acetate, a melt flow index of about 1.1 and a density of 0.9268 at 23°C, to which was added 1,6-diphenylhexatriene (1 g per 100 g of polymer ) and was exposed to irradiation from a xenon lamp.
Forsøkene ble foretatt på samme måte som i de foregående eksempler. Nedbrytningshastigheten for polymeren ble bestemt på basis av den tid som var nødvendig for at polymeren skulle bli sprø. The tests were carried out in the same way as in the previous examples. The degradation rate of the polymer was determined based on the time required for the polymer to become brittle.
De oppnådde resultater er gjengitt i den følgende tabell: The results obtained are reproduced in the following table:
Kortere sprøgjøringstid indikerer høyere nedbrytningshastighet. Shorter embrittlement time indicates a higher rate of degradation.
EKSEMPEL 4. EXAMPLE 4.
Noen filmer av handelsvanlig polypropylen (PP) hvorav noen inneholdt' 1,6-difenylheksatrien, fremstilt på samme måte som i de foregående eksempler, ble utsatt for bestråling fra en høytrykks xenon-lampe. Some films of commercial polypropylene (PP), some of which contained 1,6-diphenylhexatriene, prepared in the same manner as in the preceding examples, were exposed to irradiation from a high-pressure xenon lamp.
Nedbrytningshastigheten for polymeren ble bestemt ved hjelp av I.R.-spektroskopi. The degradation rate of the polymer was determined by I.R. spectroscopy.
Det ble satt opp en kalibreringskurve ved å anvende stearon som sammenligning på samme måte som i eksempel 1. A calibration curve was set up using stearone as a comparison in the same way as in example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19199/73A IT978147B (en) | 1973-01-15 | 1973-01-15 | PROCEDURE FOR MAKING THE POLYMERS AND POLYMERS SO OBTAINED DEGRADABLE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO140065B true NO140065B (en) | 1979-03-19 |
| NO140065C NO140065C (en) | 1979-06-27 |
Family
ID=11155729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4946/73A NO140065C (en) | 1973-01-15 | 1973-12-27 | USE OF CERTAIN UNSATURATED HYDROCARBONS TO PROMOTE THE DESTRUCTIVE EFFECT OF SUNLIGHT ON THERMO PLASTIC |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS542223B2 (en) |
| AT (1) | AT323430B (en) |
| BE (1) | BE809719A (en) |
| CA (1) | CA1054287A (en) |
| CH (1) | CH603731A5 (en) |
| CS (1) | CS186781B2 (en) |
| DD (1) | DD110282A5 (en) |
| DK (1) | DK136614B (en) |
| FR (1) | FR2213949B1 (en) |
| GB (1) | GB1437100A (en) |
| HU (1) | HU167171B (en) |
| IT (1) | IT978147B (en) |
| LU (1) | LU69159A1 (en) |
| NL (1) | NL174056C (en) |
| NO (1) | NO140065C (en) |
| YU (1) | YU35781B (en) |
| ZA (1) | ZA74182B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4399251A (en) * | 1981-12-07 | 1983-08-16 | General Electric Company | Compositions comprising a thermoplastic resin and an olefin mold release agent |
| US6126682A (en) | 1996-08-13 | 2000-10-03 | Oratec Interventions, Inc. | Method for treating annular fissures in intervertebral discs |
| GB0307615D0 (en) * | 2003-04-02 | 2003-05-07 | Ucb Sa | Authentication means |
| EP3285594B1 (en) | 2015-04-24 | 2021-03-17 | International Flavors & Fragrances Inc. | Delivery systems and methods of preparing the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2924584A (en) * | 1956-06-20 | 1960-02-09 | Du Pont | Composition comprising polyethylene and an ethylenically unsaturated aliphatic hydrocarbon of 20-35 carbon atoms and article thereof |
-
1973
- 1973-01-15 IT IT19199/73A patent/IT978147B/en active
- 1973-12-27 NO NO4946/73A patent/NO140065C/en unknown
- 1973-12-31 GB GB6019373A patent/GB1437100A/en not_active Expired
-
1974
- 1974-01-10 ZA ZA740182A patent/ZA74182B/en unknown
- 1974-01-10 FR FR7400773A patent/FR2213949B1/fr not_active Expired
- 1974-01-14 CA CA190,066A patent/CA1054287A/en not_active Expired
- 1974-01-14 CS CS7400000225A patent/CS186781B2/en unknown
- 1974-01-14 DK DK17074AA patent/DK136614B/en not_active IP Right Cessation
- 1974-01-14 BE BE139787A patent/BE809719A/en not_active IP Right Cessation
- 1974-01-14 JP JP666274A patent/JPS542223B2/ja not_active Expired
- 1974-01-14 AT AT26474A patent/AT323430B/en not_active IP Right Cessation
- 1974-01-14 CH CH47274A patent/CH603731A5/xx not_active IP Right Cessation
- 1974-01-14 HU HUSA2583A patent/HU167171B/hu unknown
- 1974-01-14 YU YU102/74A patent/YU35781B/en unknown
- 1974-01-14 LU LU69159A patent/LU69159A1/xx unknown
- 1974-01-15 NL NLAANVRAGE7400549,A patent/NL174056C/en not_active IP Right Cessation
- 1974-01-15 DD DD176020A patent/DD110282A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1437100A (en) | 1976-05-26 |
| DE2401568A1 (en) | 1974-08-01 |
| DK136614B (en) | 1977-10-31 |
| DK136614C (en) | 1978-04-10 |
| FR2213949B1 (en) | 1979-03-02 |
| BE809719A (en) | 1974-05-02 |
| NL174056B (en) | 1983-11-16 |
| NL174056C (en) | 1984-04-16 |
| FR2213949A1 (en) | 1974-08-09 |
| CA1054287A (en) | 1979-05-08 |
| DD110282A5 (en) | 1974-12-12 |
| JPS49105838A (en) | 1974-10-07 |
| LU69159A1 (en) | 1974-05-17 |
| NL7400549A (en) | 1974-07-17 |
| ZA74182B (en) | 1974-11-27 |
| NO140065C (en) | 1979-06-27 |
| CS186781B2 (en) | 1978-12-29 |
| AU6410574A (en) | 1975-07-03 |
| YU35781B (en) | 1981-06-30 |
| YU10274A (en) | 1980-10-31 |
| JPS542223B2 (en) | 1979-02-03 |
| IT978147B (en) | 1974-09-20 |
| AT323430B (en) | 1975-07-10 |
| HU167171B (en) | 1975-08-28 |
| CH603731A5 (en) | 1978-08-31 |
| DE2401568B2 (en) | 1977-05-18 |
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