EP1123347A1 - Monovinylidene aromatic resins - Google Patents
Monovinylidene aromatic resinsInfo
- Publication number
- EP1123347A1 EP1123347A1 EP99942100A EP99942100A EP1123347A1 EP 1123347 A1 EP1123347 A1 EP 1123347A1 EP 99942100 A EP99942100 A EP 99942100A EP 99942100 A EP99942100 A EP 99942100A EP 1123347 A1 EP1123347 A1 EP 1123347A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- resin
- monovinylidene aromatic
- percent
- weight
- aromatic resin
- 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.)
- Withdrawn
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 73
- 239000011347 resin Substances 0.000 title claims abstract description 73
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 36
- 230000002902 bimodal effect Effects 0.000 claims abstract description 13
- 238000009826 distribution Methods 0.000 claims abstract description 4
- 239000006260 foam Substances 0.000 claims description 15
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 238000000034 method Methods 0.000 description 16
- 239000000178 monomer Substances 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 235000013372 meat Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920005990 polystyrene resin Polymers 0.000 description 5
- 239000004604 Blowing Agent Substances 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- XIRPMPKSZHNMST-UHFFFAOYSA-N 1-ethenyl-2-phenylbenzene Chemical class C=CC1=CC=CC=C1C1=CC=CC=C1 XIRPMPKSZHNMST-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical class C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical class CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000004798 oriented polystyrene Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- KHMYONNPZWOTKW-UHFFFAOYSA-N pent-1-enylbenzene Chemical class CCCC=CC1=CC=CC=C1 KHMYONNPZWOTKW-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Definitions
- MONOVINYLIDENE AROMATIC RESINS The process of the present invention relates to monovinylidene aromatic resins.
- Monovinylidene aromatic resins have been used in applications such as foam sheet, extrusion and oriented articles.
- Plasticizers have typically been used in such resins to increase the flow and increase the rate of production of molded or extruded articles.
- plasticizers such as mineral oil, significantly lower the glass transition temperature (Tg) of the resin. This can slow the production time, since the products produced must be cooled to a lower temperature for adequate setting to occur prior to mold removal.
- Tg glass transition temperature
- the use of plasticizers such as limonene add significant cost to the resins, making their use undesirable.
- JP-08-172959 discloses a method of modifying aromatic plastics by compounding styrene oligomers having a molecular weight of 2200-3800 and a polydispersity of 1.6 to 2.1 with aromatic plastics such as polystyrene.
- the polystyrene compositions disclosed still have significantly reduced Tg due to the presence of mineral oil plasticizer in Styron 666 and the flexural strength is significantly reduced.
- the present invention is a monovinylidene aromatic resin having a bimodal weight average molecular weight (Mw) distribution such that 85 to 95 percent by weight of the resin is a fraction having an average Mw of from 250,000 to 400,000 and from 2 to 15 percent by weight of the resin is a fraction having a Mw of 1 ,000 to 20,000, wherein each fraction has a polydispersity (Mw/Mn) of from 1.5 to 3.0.
- Mw weight average molecular weight
- This resin has good flow and Tg properties and can be used in various applications, such as injection molding, foam sheet and oriented polystyrene extruded sheet, resulting in increased production rates.
- the present invention is a monovinylidene aromatic resin having a specific Mw profile having an improved balance of melt flow and strength without the addition of a traditional plasticizer.
- the monovinylidene aromatic resin has a bimodal Mw distribution such that 85 to 95 percent by weight of the resin has an average Mw of from 250,000 to 400,000 and from 2 to 15 percent by weight of the resin has a Mw of 1 ,000 to 20,000, wherein each fraction has a polydispersity (Mw/Mn) of from 1.5 to 3.0.
- Monovinylidene aromatic polymers suitable for the process of the present invention are those produced by polymerizing a vinyl aromatic monomer.
- Vinyl aromatic monomers include, but are not limited to those described in US-A-4,666,987, US-A-4,572,819 and US-A-4,585,825.
- the monomer is of the formula:
- Ar is an aromatic ring structure having from 1 to 3 aromatic rings with or without alkyl, halo, or haloalkyl substitution, wherein any alkyl group contains 1 to 6 carbon atoms and haloalkyl refers to a halo substituted alkyl group.
- Ar is phenyl or alkylphenyl, wherein alkylphenyl refers to an alkyl substituted phenyl group, with phenyl being most preferred.
- Typical vinyl aromatic monomers which can be used include: styrene, alpha-methylstyrene, all isomers of vinyl toluene, especially paravinyltoluene, all isomers of ethyl styrene, propyl styrene, vinyl biphenyl, vinyl naphthalene, and vinyl anthracene, and mixtures thereof.
- the vinyl aromatic monomers may also be combined with other copolymerizable monomers.
- Examples of such monomers include, but are not limited to acrylic monomers such as acrylonitrile, methacrylonitrile, methacrylic acid, methyl methacrylate, acrylic acid, and methyl acrylate; maleimide, phenylmaleimide, and maleic anhydride.
- the polymerization of the vinyl aromatic monomer may be conducted in the presence of predissolved elastomer to prepare impact modified, or grafted rubber containing products, examples of which are described in US-A-3,123,655, US-A-3,346,520, US-A-3,639,522, and US-A-4,409,369.
- Polymerization processes and process conditions for the polymerization of vinyl aromatic monomers are well known in the art. Although any polymerization process can be used, typical processes are continuous bulk or solution polymerizations as described in US-A-2,727,884 and US-A-3,639,372. Cationic polymerization processes can also be used, especially in preparing the low molecular weight component. Such processes are well known in the art such as in US-A-4,087,599, US-A-4,161 ,573 and US-A-4,112,209.
- the major proportion of the monovinylidene aromatic resin is a high molecular weight fraction.
- at least 85 percent, preferably at least 90 percent and most preferably at least 95 percent of the resin has a molecular weight from 250,000, preferably from 260,000, more preferably from 270,000 and most preferably from 280,000 to 400,000, preferably to 375,000, more preferably to 350,000 and most preferably to 325,000.
- the resin also contains a lower molecular weight fraction which is typically from 2 percent, preferably from 2.5 percent, more preferably from 3 percent and most preferably from 3.5 percent, and even more preferably from 5 percent to 15 percent, preferably to 12 percent and most preferably to 10 percent, and even more preferably to 8 percent by weight.
- This lower molecular weight fraction has a Mw which is typically from 1 ,000, preferably from 1 ,500, more preferably from 2,000 and most preferably from 2,500 to 20,000, preferably to 18,000, more preferably to 16,000 and most preferably to 14,000.
- Mw which is typically from 1 ,000, preferably from 1 ,500, more preferably from 2,000 and most preferably from 2,500 to 20,000, preferably to 18,000, more preferably to 16,000 and most preferably to 14,000.
- Molecular weight values are measured using gel permeation chromatography techniques (GPC) which are well known in the art.
- the polydispersity (weight average molecular weight(Mw))/(number average molecular weight (Mn)) for each fraction described above is typically from 1.5, preferably from 1.6, more preferably from 1.7 and most preferably from 1.8 to 3.0, preferably to 2.8, more preferably to 2.7 and most preferably to 2.6. It has been discovered that resins falling within this bimodal Mw profile have excellent flow and Tg properties without using plasticizers such as mineral oil.
- Typical polymer additives can also be included in the resin of the present invention, including antioxidants, stabilizers, mold release agents, and chain transfer agents
- the high Mw fraction and the low Mw fraction are made in separate reactors and combined in the appropriate proportions to produce the resin of the present invention.
- the individual resins can be made simultaneously and combined within the same process or the two resins can be blended using any blending method including solution or dry blending.
- the resin of the present invention can also be produced within one continuous process wherein the low molecular weight fraction is produced in situ while producing the high molecular weight fraction within the same process. This can be accomplished using methods described in EP-797,600.
- the monovinylidene aromatic polymer is a polystyrene resin having a high molecular weight fraction of at least 320,000 and a low molecular weight fraction of from 1 ,000 to 20,000, which is used to produce foam sheet.
- Methods of producing foam sheet are well known in the art, any of which can be used to produce foam sheet from the resin of the present invention.
- Typical blowing agents include carbon dioxide, hydrochlorofluorocarbons, and alcohols, mixtures thereof.
- the lower molecular weight fraction increases the flow of the polystyrene resin without substantially lowering the Tg, thus production can occur at higher rates compared to resins containing plasticizers which lower the Tg.
- the monovinylidene aromatic resin of the present invention can also be used in blends with other polymers, such as high impact monovinylidene aromatic polymers. These blends can be used in applications such as form-fill-seal products, especially yogurt type containers.
- the monovinylidene aromatic resin of the present invention can also be used in various applications including foam sheet, meat trays, egg cartons, cups, biaxially oriented sheet, injection molded articles and oriented products.
- foam sheet, meat trays, egg cartons, cups, biaxially oriented sheet, injection molded articles and oriented products are provided to illustrate the present invention. The examples are not intended to limit the scope of the present invention and they should not be so interpreted. Amounts are in weight parts or weight percentages unless otherwise indicated. EXAMPLE 1
- a solution of 3.5 weight percent low molecular weight polystyrene (Mw 1 ,400, Mn 660), 3.0 percent ethylbenzene, 93.5 percent styrene, 75 ppm of 1 ,1-bis(tert- butylperoxy)cyclohexane initiator and 25 ppm sulfoethyl methacrylate is passed through a series of stirred tube reactors with a temperature gradient from 128 to 150°C.
- a slurry of zinc stearate in ethylbenzene is added halfway through the reactors such that the final concentration of zinc stearate in the product is approximately 1200 ppm.
- the partial polymer is devolatilized at 230°C and 10 mm, followed by pelletization, to give a bimodal polystyrene resin with 94.5 percent of the resin having a Mw of 328,000 (Mn of 134,000) and 5.5 percent having a Mw of 1 ,400.
- This resin exhibits an enhanced flow rate (MFR of 2.5 vs. 1) over monomodal high MW prepared from styrene under identical polymerization conditions while decreasing the Tg of the resin only slightly (106°C vs. 108°C).
- the following molding conditions are used for ASTM specimen molding:
- Control 1 and 2 are StyronTM 685 D available from The Dow Chemical Company.
- Un-notched Izod (kg-cm/cm) 20 20 37 Fill time (seconds) 0.7 unavailable 0.49 Hold time (seconds) 0.6 unavailable 0.7 Cooling time (seconds) 2.6 2.2 2 Plastication time (seconds) 3.87 4.05 3.41 Cycle time (seconds) 7.2 7.4 6.75
- the bimodal resin is also used to produce foam sheet and meat trays therefrom.
- Meat trays are manufactured using a continuos roll fed thermoformer where a roll of the bimodal resin foam sheet (produced using a tandem extrusion process) is passed through a heated oven and is heated to a temperature sufficient to soften and expand the sheet. The expanded foam sheet is vacuum formed into meat trays and cooled. The formed sheet containing the meat trays is mechanically cut to form the trays. The remaining portion of the sheet or web is fed into a grinder, re-ground and later extruded into additional foam sheet.
- the typical gauge and density of foam sheet used to make meat trays is 110 to 125 mils and 48 to 56 g/l, respectively.
- a resin blend of 80 percent high heat general purpose polystyrene (STYRONTM 685D) and 20 percent STYRONTM 685D regrind and a resin blend of 80 percent bimodal polystyrene resin as prepared above and 20 percent bimodal polystyrene resin regrind are extruded and compared using a commercial tandem extrusion process (two extruders in series).
- foam sheet samples are made with the same gauge, density, basis wt. and cell size. These parameters are controlled by adjusting the percent blowing agent, percent talc, and the rate at which the sheet is pulled.
- the blowing agent is a blend of hydrocarbon and carbon dioxide. The carbon dioxide was the lesser of the two blowing agent components.
- Post expansion is the amount the foam sheet expands versus its initial gauge within a thermoformer.
- Post expansion of the meat trays is measured by measuring stacks of 125 number 2 type meat trays for their overall average heights. The results are listed in Table IV. The bimodal resin shows a 7 percent increase in stack height. TABLE IV Stack Height of 125 Number 2 Type Meat Trays
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9957298P | 1998-09-09 | 1998-09-09 | |
US99572P | 1998-09-09 | ||
PCT/US1999/018221 WO2000014157A1 (en) | 1998-09-09 | 1999-08-11 | Monovinylidene aromatic resins |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1123347A1 true EP1123347A1 (en) | 2001-08-16 |
Family
ID=22275652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99942100A Withdrawn EP1123347A1 (en) | 1998-09-09 | 1999-08-11 | Monovinylidene aromatic resins |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1123347A1 (en) |
CN (1) | CN1317036A (en) |
AU (1) | AU5554899A (en) |
CO (1) | CO5050401A1 (en) |
WO (1) | WO2000014157A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004044087A1 (en) * | 2004-09-09 | 2006-03-16 | Tesa Ag | Functional polymer or contact adhesive, e.g. for use on adhesive tape, contains functionalised polymer with a high content of functional monomer units and a special type of mol. wt. distribution |
DE112005001972A5 (en) | 2004-09-09 | 2007-09-13 | Tesa Ag | Functionalized polymers or PSAs |
WO2008086362A1 (en) * | 2007-01-10 | 2008-07-17 | Albemarle Corporation | Brominated styrenic polymer compositions and processes for producing same |
TW200838919A (en) * | 2007-01-10 | 2008-10-01 | Albemarle Corp | Brominated styrenic polymer compositions and processes for producing same |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2864802A (en) * | 1955-11-28 | 1958-12-16 | Dow Chemical Co | Molding compositions of high molecular weight and low molecular weight polymers |
DE2239356A1 (en) * | 1972-08-10 | 1974-02-21 | Basf Ag | STYRENE POLYMERIZES WITH IMPROVED FLOWABILITY |
ES2127929T3 (en) * | 1993-06-04 | 1999-05-01 | Dow Chemical Co | MOLDING AND FOAM COMPOSITION OF IMPROVED STYRENE RESIN. |
JPH09328589A (en) * | 1996-06-12 | 1997-12-22 | Yasuhara Chem Kk | Method for modifying aromatic plastic |
-
1999
- 1999-08-11 EP EP99942100A patent/EP1123347A1/en not_active Withdrawn
- 1999-08-11 AU AU55548/99A patent/AU5554899A/en not_active Abandoned
- 1999-08-11 CN CN 99810760 patent/CN1317036A/en active Pending
- 1999-08-11 WO PCT/US1999/018221 patent/WO2000014157A1/en not_active Application Discontinuation
- 1999-09-09 CO CO99057236A patent/CO5050401A1/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO0014157A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU5554899A (en) | 2000-03-27 |
CO5050401A1 (en) | 2001-06-27 |
WO2000014157A1 (en) | 2000-03-16 |
CN1317036A (en) | 2001-10-10 |
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