SE1400432A1 - A highly stabile plasticized polyvinyl halide composition r acid - Google Patents
A highly stabile plasticized polyvinyl halide composition r acid Download PDFInfo
- Publication number
- SE1400432A1 SE1400432A1 SE1400432A SE1400432A SE1400432A1 SE 1400432 A1 SE1400432 A1 SE 1400432A1 SE 1400432 A SE1400432 A SE 1400432A SE 1400432 A SE1400432 A SE 1400432A SE 1400432 A1 SE1400432 A1 SE 1400432A1
- Authority
- SE
- Sweden
- Prior art keywords
- plasticized
- composition
- polyvinylhalide
- composition according
- char
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- 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
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
- C07C67/40—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester by oxidation of primary alcohols
-
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
2
processability of the plasticized polyrner such as when agglomerating the polymer/plasticizer
mixture but also when injection molding articles of said plasticized polymer.
Long term thermal stability is also an important consideration in articles that
would be subj ected to elevated temperatures over a long time. As an example of such articles
can be mentioned hoses connecting the radiator of a vehicle to the engine. The hot water may
here cause migration of plasticizer. It may also cause hydrolyzation of the plasticizer itself. In
the long run this will cause the hose in this speci?c example to become brittle. Eventually
cracks and leaks will appear.
Most plasticized polyvinylhalides have a poor stability towards UV light. This will be noticed
by yellowing, the surface becoming sticky and slippery, the plasticized polymer becoming
harder and more brittle and in some cases shrinking. This will radically reduce the useful life
of plasticized polyvinylhalides in outdoor use.
Accordingly the invention relates to a highly stabile plasticized polyvinylhalide composition.
The invention is characterized in that the composition comprises polyvinylhalide,
_ pentaerythritoltetravalerate and an epoxidized unsaturated fatty acid ester having an iodine
value of at least 135 prior to the epoxidation. This means that an unsaturated fatty acid ester
having an iodine value of at least 135 is epoxidized. The iodine value will suitably be below
, preferably below 10 after epoxidation.
According to a preferred embodiment of the invention the epoxidized
unsaturated fatty acid ester has at least ?ve epoxide groups.
The polyvinylhalide is suitably selected from the group consisting of
polyvinylchloride, polyvinylidenedichloride, polyvinylidenedi?ouride.
According to a preferred embodiment of the invention the epoxidized unsaturated fatty acid
ester is a glycerol ester selected from the group consisting of linseed oil and tung oil. Said
linseed oil and/or tung oil is accordingly epoxidized so that the average ester molecule
comprises ?ve or more epoxide groups.
According to one embodiment of the invention a plasticizer-mixture of 2 - 10% by weight of
the epoxidized unsaturated fatty acid ester and balance to 100% by weight of
3
pentaerythritolvalerate is present in the highly stabile plasticized polyvinylhalide composition.
The highly stabile plasticized polyvinylhalide composition suitable comprises 10 - 60 % by
weight of plasticizer-mixnlre.
According to a special embodiment of the invention, the highly stabile plasticized
polyvinylhalide composition further comprises a PVC stabilizer selected from the group
consisting of barium/zink compound and calcium/zink compound. The purpose of such a
PVC stabilizer is foremost to stabilize the polymer in the composition according to the
invention. The PVC stabilizer may 'further comprise a co-stabilizer containing polyhydric
alcohols selected from the group consisting of mono-pentaerythritol, di-pentaerythritol,
trimethylolpropane, di-trimethylolpropane, pentaerythritol adipate and mixtures thereof.
The present invention is further explained with reference to enclosed embodiment Examples,
which are to be construed as illustrative and not limiting in any way.
Example la illustrates evaluation of the UV stability of plasticized PVC compositions.
Example lb illustrates evaluation of the Thermal stability of plasticized PVC compositions.
Example lc illustrates evaluation of the hydrolytic stability of plasticized PVC compositions.
Example la
A number of samples Were prepared as a first trial to evaluate the effect of UV light.
Sheets having a thickness of 80 - 100um were prepared. These sample sheets consisted of the
following compositions;
Sample No. PVC Plasticizer Stabilizer
K-value 70 /amount /amount
I 100 phr Pentatetravalerate / 30 phr Ba/Zn / 2 phr
II 100 phr Diisononyl phthalate / 30 phr Ba/Zn / 2 phr
III 100 phr Diisononyl cyclohexane-l,2-dicarboxylate/ Ba/Zn / 2 phr
phr
IV 100 phr Dioctyl phthalate / 30 phr Ba/Zn / 2 phr
V 100 phr Dioctyl terephthalate/ 30 phr Ba/Zn / 2 phr
The samples were subjected to a QUV test for 1750 hours. The test Were run in cycles of 4h
UV-A light at 60°C and 4h Conditioning at 50°C in accordance with ISO 4891-1 and ISO
4892-2. The tests Were performed in a QUV Weathering tester from Q-Tester.
The yellowing index Yi was determined in accordance With ASTM D 1925-70
at 24 hours, 240 hours, 500 hours and then at 250 hour interval until 1750 hours was reached.
The following results were obtained;
Graph 1
Yellowing index Yi
Cycle 4h/60°C + 4h/50°C + UV
80
70 vsample2
a
f l 3
60 0,/ sampe
a / sample5
n!-
40 .ft aa”
/
_/- dä; at' _-- sample4
/ â v'
./' æâ
, ” få”
.Xl ,o;;%9-
_ I å samplel
0 l I l l l I l l
Oh 250h 500h 750h 1000h 1250h 1500h l750h
The conclusion of the trial is that sample 1, a PVC resin plasticized with pentatetravalerate is
virtually unaffected while the other samples show varying degree of increasing yellowing
over the test period.
There was accordingly no reason to perform testing on thermal and hydrolytic
stability on sample 2 - 5 as they did not perform well in the UV test.
Example lb
A set of samples was prepared as to evaluate the thermal stability.
Sheets having a thickness of lmm were prepared. These sample sheets consisted of the
following compositions;
Sample Polymer Plasticizer Co-plasticizer Stabilizer
No. /amount /amount /amount /amount
VI PVC/ Pentatetravalerate / 70 phr Lancro?ex L/ 1 phr Ca/Zn / 2 phr
100 phr
VII PVC / Pentatetravalerate/ 70 phr Lancro?ex L/ 1.5 phr Ca/Zn / 2 phr
100 phr
The samples were subjected to 200°C for 2 minutes in a Mathis oven. Thermal stability was
measured with a Werner-Mathis oven thermo tester. The films were subjected to 200°C in the
oven. After 5 min ground time the ?lms were removed from the oven in 20 mm steps every
60 s. The time until the ?lm became discoloured was measured for each ?lm.
It showed that sample VI and VII had suf?cient stability for normal processing with the
ability to endure the temperature without coloration for 12 - 15 minutes. As comparison
commercially available compositions II and III typically will endure the same temperature for
- 12 minutes.
Example lc
A set of samples was prepared as to evaluate the hydrolytic stability.
The samples correspond fully to sample VI and VII in example lb above.
The samples were subjected to 80°C at a relative humidity of 100% in a climate chamber for 1
week. The evaporation of valeric acid, indicating hydrolysation of the pentatetravalerate was
measured. The amount of valeric acid detected was below 5 ppm for both samples indicating
that the compositions are very stable.
6
We ?nd our conclusions to be that a plasticized polyvinyl halide composition in accordance to
the invention is indeed very stable and surprisingly stabile in outdoor applications due to its
ability to withstand UV radiation without noticeable degradation of the composition.
Example 2a
Once the thermal, hydrolytic and UV stability was analysed, a further series of trials were
performed in order to analyse and compare other important characteristics of plasticized PVC.
It was considered that the characteristics; fusion time, Shore hardness, migration and volatility
would not be greatly affected by the co-plasticizer whereby this was omitted for the sake of
simplicity.
Preparation of plasticised PVC sheets
PVC resins (suspensions of PVC particles in a plasticiser) of below forrnulations were
prepared:
Sample No. Polymer Plasticizer Stabilizer
(Norvinyl S- / (g) / (g)
706) / (g)
VIII PVC/ 190.8 Pentatetravalerate / 95.4 Ba/Zn / 3.8
IX PVC / 190.8 Diisononyl phthalate / 95.4 Ba/Zn / 3.8
X PVC/ 190.8 Diisononyl cyclohexane-l,2-dicarboxylate Ba/Zn/ 3.8
/ 95.4
XI PVC/ 190.8 Dioctyl phthalate / 95.4 Ba/Zn/ 3.8
The components of each PVC resin were carefully mixed and then calendared to a sheet using
a two-roll mill at l65°C.
Example 2b
Evaluation of the obtained plasticised PVC sheets
All plasticised PVC sheets obtained in Example 4 were evaluated regarding fusion time,
hardness, migration and volatility.
Fusion Time
A test to determine the time required for PVC and plasticiser to completely mix together and
form a unifonn blend. A mixing bowl was heated to the test temperature of 88°C and charged
with 300 g PVC resin. A stirring of 60 rpm was applied for 5 minutes to allow the resin to
reach the bowl temperature. 150 g plasticizer was then added and the time required for PVC
and plasticiser to completely mix together and form a uniform blend was measured.
The results are presented in Chart l.
Hardness
Durometer hardness Shore A. (Standard: ASTM 224023)
A test based on the penetration of a speci?c type of indentor when forced into the material
under speci?c conditions. The indentation hardness is inversely related to the penetration and
dependant on the elastic modulus and viscoelastic behaviour of the material.
The results are presented in Chart 2.
Migration
Deterrnination of migration of plasticisers (Standard: ISO 177)
A test based on quantitative determination of the loss of mass of a sheet of plasticized plastic
placed between two fresh absorbent backing discs. A rubber-PVC-rubber Sandwich was
wrapped with aluminium foil and rubber sheets before being placed between two glass plates.
A weight of Skg was placed on the Sandwich assembly and the whole package was placed in
an oven with a temperature of 70 :t2°C. The samples were then picked out and the weight of
both the plasticized plastic and the absorbent backing discs was measured after 3, 7, 14 and 28
days.
The results for 28 days are presented in Chart 3.
Volatility
Activated carbon method (Standard: ISO 176 Method A)
A test method based on quantitative detennination of the loss of plasticiser from plasticized
plastic materials upon heating, where it is generally assumed that no significant amounts of
other volatile materials are present. l20cm3 of activated carbon was spread on the bottom of
metal container and a test sample was placed on top of the carbon and covered with another
120cm“ of activated carbon. Two further samples were placed in the container, each covered
with 120cm3 of carbon, where after the container was sealed with a lid. The container was
placed in oven with a temperature of 100:tl°C. The activated carbon surrounding the samples
absorbed the plasticiser extracted upon heating. After 7 days the container was removed from
the oven and cooled to room temperature. The samples were removed from the container,
carefully brushed free from carbon particles and weighed.
The results are presented in Chart 4.
Chart 1 Fusion time
Fusion time
I 0:48
09:36
08:24
07:12
06:00
04:48 -
03:36 -
02:24 -
01:12 -
00:00 -
XI IX X VIII
The fusion time for the plasticiser VIII according to the present invention was found to be
shorter than plasticisers IX and X.
Chart 2 Hardness
Shore A Hardness
86
84
82
80-
78-
76-
74 -
XI IX X VIII
The plasticising effect of the plasticisers according to the present invention was found to be
high in comparison to commercially available plasticisers XI, IX and X. This means that
lower amounts of plasticiser can be added with maintained hardness.
Chart 3 Migration
Migration
IX X VIII
The plasticiser VIII according to the invention showed very good migration values.
Chart 4 Volatility
Volatility
XI
VIII
-20
I
-25
The plasticíser VIII according to the invention showed very good volatility value. The
comparative example XI and X showed to be rather poor due to its relatively high volatility.
ll
It has, during experimentation with the plasticisers according to the invention been found that
the fusion time is very short, while quite surprisingly, the volatility is lower than
commercially available plasticisers. The short fusion time implies that the processing time can
be shorter and/or temperature during agglomeration of plasticiser can be lower Wherein any
problem With thermal stability during processing of the composition according to the
invention becomes even less signi?cant.
The composition in accordance with the invention has also been found to be
remarkably UV- stabile as well as having fully suf?cient thermal and hydrolytic stability. It
also has the advantage of not containing phthalate based plasticisers, which is a desired
property. The low volatility together with the high level of UV-stability will increase the
useful life of products made of a composition in accordance with the invention.
Claims (8)
1. A highly stabile plasticized polyvinylhalide composition, c h a r a c t e ri z e d in that the composition comprises polyvinylhalide, pentaerythritoltetravalerate and an epoxidized unsaturated fatty acid ester, the unsaturated fatty acid ester having an iodine value of at least 135 prior to epoxidation.
2. A composition according to claim 1, c h a r a c t e r i z e d in that the epoxidized unsaturated fatty acid ester have at least ?ve epoxide groups.
3. A composition according to claim 1, c h a r a c t e r i z e d in that the polyvinylhalide is selected from the group consisting of polyvinylchloride, polyvinylidenechloride, polyvinylidene?ouride.
4. A composition according to claim 2, c h a r a c t e r i z e d in that the epoxidized unsaturated fatty acid ester is a glycerol ester selected from the group consisting of linseed oil and tung oil.
5. A composition according to any of the preceding claims, c h a r a c t e r i z e d in that that a plasticizer-mixture of 2 - 10% by weight of the epoxidized unsaturated fatty acid ester and balance to 100% by weight of pentaerythntolvalerate is present in the highly stabile plasticized polyvinylhalide composition.
6. A composition according to claim 6, c h a r a c t e r i z e d in that the highly stabile plasticized polyvinylhalide composition comprises 10 - 60 % by weight of plasticizer- mixture.
7. A composition according to claim 6 or 7, c h a r a c t e ri z e d in that the highly stabile plasticized polyvinylhalide composition further comprises a PVC stabilizer selected from the group consisting of barium/zink compound and calcium/zink compound.
8. A composition according to claim 8, c h a r a c t e r i z e d in the PVC stabilizer further comprises a co-stabilizer containing polyhydric alcohols selected from the group consisting of mono-pentaerythritol, di-pentaerythritol, trimethylolpropane, di- trimethylolpropane and mixtures thereof.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1400432A SE539458C2 (sv) | 2014-09-15 | 2014-09-15 | A highly stabile plasticized polyvinyl halide composition comprising pentaerythritoltetravalerate and an epoxidized unsaturated fatty acid ester. |
| PCT/SE2015/000053 WO2016043639A1 (en) | 2014-09-15 | 2015-09-08 | A highly stabile plasticized polyvinyl halide composition |
| EP15841782.4A EP3194496B1 (en) | 2014-09-15 | 2015-09-08 | A highly stabile plasticized polyvinyl halide composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1400432A SE539458C2 (sv) | 2014-09-15 | 2014-09-15 | A highly stabile plasticized polyvinyl halide composition comprising pentaerythritoltetravalerate and an epoxidized unsaturated fatty acid ester. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE1400432A1 true SE1400432A1 (sv) | 2016-03-16 |
| SE539458C2 SE539458C2 (sv) | 2017-09-26 |
Family
ID=55533561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE1400432A SE539458C2 (sv) | 2014-09-15 | 2014-09-15 | A highly stabile plasticized polyvinyl halide composition comprising pentaerythritoltetravalerate and an epoxidized unsaturated fatty acid ester. |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP3194496B1 (sv) |
| SE (1) | SE539458C2 (sv) |
| WO (1) | WO2016043639A1 (sv) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483918A (zh) * | 2019-08-28 | 2019-11-22 | 安徽万朗磁塑股份有限公司 | 一种耐uv环保型pvc门封材料配方及其制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202015105425U1 (de) * | 2015-10-14 | 2017-01-17 | Rehau Ag + Co. | Zusammensetzung |
| DE102018005822B4 (de) * | 2018-07-25 | 2024-08-14 | Staedtler Se | Radierer |
| SE545279C2 (en) * | 2020-03-11 | 2023-06-13 | Perstorp Ab | A stable pvc composition comprising an environment-friendly plasticizer |
| KR20210120375A (ko) * | 2020-03-26 | 2021-10-07 | 애경유화주식회사 | 복합 가소제 조성물 및 이를 이용한 고분자 수지 조성물 |
| CN114044994A (zh) * | 2022-01-13 | 2022-02-15 | 赛立特(南通)安全用品有限公司 | 一种柔性缓冲材料及其制备方法和用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618586A1 (de) * | 1967-03-31 | 1971-04-01 | Alfred Krueger | Verfahren zur Herstellung von Fettsaeure-Mono- oder Diestern des Pentaerythrits |
| US3670013A (en) * | 1969-10-16 | 1972-06-13 | Hercules Inc | Synthesis of partial esters of certain poly(neopentyl polyols) and aliphatic monocarboxylic acids |
| DE2652328A1 (de) * | 1976-11-17 | 1978-05-18 | Neynaber Chemie Gmbh | Bleiverbindungen enthaltende stabilisator-gleitmittel-kombination fuer formmassen auf basis von polyvinylchlorid |
| US5036121A (en) * | 1988-09-06 | 1991-07-30 | The B. F. Goodrich Company | Flame and smoke retardant cable insulation and jacketing compositions |
| EP1208148A1 (en) | 1999-06-30 | 2002-05-29 | Perstorp Ab | Plasticiser for polymeric compositions |
| BRPI0705276A2 (pt) * | 2007-12-10 | 2009-08-11 | Nexoleum Bioderivados Ltda | plastificantes primários de pvc derivados de óleos vegetais, processo de obtenção de plastificantes primários de pvc derivados de oléos vegetais e composição de pvc plastificado |
| BRPI0905919B1 (pt) * | 2008-02-15 | 2019-07-02 | Union Carbide Chemicals & Plastics Technology Llc | Composição de sistema plastificante, composição de polímero plastificado e cabo |
| JP5693589B2 (ja) * | 2009-09-30 | 2015-04-01 | ダウ グローバル テクノロジーズ エルエルシー | １２−ヒドロキシステアリン酸のアセチル化グリセリドおよびエポキシ化脂肪酸エステルとのブレンド |
| US8552098B2 (en) * | 2009-09-30 | 2013-10-08 | Dow Global Technologies Llc | Purified acetylated derivatives of castor oil and compositions including same |
| US8697787B2 (en) * | 2009-09-30 | 2014-04-15 | Dow Global Technologies Llc | Flexible PVC compositions made with plasticizers derived from renewable sources |
| US20150203657A1 (en) * | 2010-08-23 | 2015-07-23 | Perstorp Ab | Non-phthalic plasticiser |
| JP2016027064A (ja) * | 2012-11-30 | 2016-02-18 | Ｋｈネオケム株式会社 | 塩化ビニル系樹脂用可塑剤およびそれを含有する塩化ビニル系樹脂組成物 |
-
2014
- 2014-09-15 SE SE1400432A patent/SE539458C2/sv unknown
-
2015
- 2015-09-08 EP EP15841782.4A patent/EP3194496B1/en active Active
- 2015-09-08 WO PCT/SE2015/000053 patent/WO2016043639A1/en active Application Filing
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110483918A (zh) * | 2019-08-28 | 2019-11-22 | 安徽万朗磁塑股份有限公司 | 一种耐uv环保型pvc门封材料配方及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016043639A1 (en) | 2016-03-24 |
| EP3194496A4 (en) | 2018-04-18 |
| EP3194496A1 (en) | 2017-07-26 |
| EP3194496B1 (en) | 2020-11-25 |
| SE539458C2 (sv) | 2017-09-26 |
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