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WO1998042760A1 - Copolymeres d'ethylene greffes - Google Patents

Copolymeres d'ethylene greffes Download PDF

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Publication number
WO1998042760A1
WO1998042760A1 PCT/US1998/005552 US9805552W WO9842760A1 WO 1998042760 A1 WO1998042760 A1 WO 1998042760A1 US 9805552 W US9805552 W US 9805552W WO 9842760 A1 WO9842760 A1 WO 9842760A1
Authority
WO
WIPO (PCT)
Prior art keywords
copolymer
anhydride
unsaturated acid
uaa
grafted
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.)
Ceased
Application number
PCT/US1998/005552
Other languages
English (en)
Inventor
Jean-Roch Hector Schauder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Chemical Patents Inc
Original Assignee
Exxon Chemical Patents Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Exxon Chemical Patents Inc filed Critical Exxon Chemical Patents Inc
Priority to AU65753/98A priority Critical patent/AU6575398A/en
Priority to BR9808027-0A priority patent/BR9808027A/pt
Priority to KR1019997008587A priority patent/KR20010005528A/ko
Priority to JP54583998A priority patent/JP2001518137A/ja
Priority to EP98911905A priority patent/EP0968235A1/fr
Publication of WO1998042760A1 publication Critical patent/WO1998042760A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C08F290/042—Polymers of hydrocarbons as defined in group C08F10/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond

Definitions

  • This invention relates to grafted ethylene copolymers, compositions comprising the grafted ethylene copolymers, and a process to make the grafted ethylene copolymers.
  • U.S. 5,346,963 describes substantially linear olefin polymers produced by Dow Chemical Company's "constrained geometry" catalysts grafted with an unsaturated organic compound which exhibit adhesive properties as well as imparting desirable impact properties to various thermoplastic polymer blends. These polymers however do not achieve high levels of grafting without an increase in viscosity.
  • EPA 0 440 506 discloses derivatized ethylene alpha-olefin polymers useful as multifunctional viscosity index improvers. These polymers however are generally only functionalized at the chain end and have thus only one functionality per chain. The chemistry used in this case generally leads to too low functionalization levels for the typical medium viscosity polymers used to modify engineering thermoplastics.
  • This invention relates to a grafted ethylene copolymer comprising ethylene and an alpha-olefin grafted with 0.1 weight% or more of an unsaturated acid or anhydride wherein the copolymer prior to grafting is characterized by: 1) a vinylidene to vinyl end chain unsaturation ratio of 3 or less, and 2) a CDBI of 60 % or more if the polymer has a density of 0.90g/cc or more or a reactivity ratio between 0.5 and 1.5 or less if the polymer has a density of less than 0.90 g/cc, and wherein the grafted copolymer is characterized by a number of unsaturated acid or anhydride molecules per chain of 2 or more as calculated according to the following formula: [Mn* UAA (wt%)] / [UAA(Mw)] wherein Mn is the number average molecular weight as measured by GPC, UAA(wt%) is the weight percent of the unsaturated acid or anhydride as measured by
  • Figure 1 is a graph of the MFR increase during grafting for examples 1-8. (Cond.l is example 1 and so on).
  • Figure 2 is a graph of the MFR increase during grafting for examples 9-11. (Cond.9 is example 9 and so on).
  • This invention relates to a grafted ethylene copolymer comprising ethylene and an alpha-olefin grafted with 0.1 weight % or more of an unsaturated acid or anhydride wherein the copolymer prior to grafting:
  • Mn is the number average molecular weight as measured by GPC
  • UAA(wt%) is the weight percent of the unsaturated acid or anhydride as measured by FTIR spectroscopy
  • UAA(Mw) is the molecular weight of the unsaturated acid or anhydride, and optionally 4) an Mw/Mn greater than (I ⁇ o/I 2 )-4.63.
  • the ethylene copolymer prior to grafting is a copolymer of ethylene and an ⁇ -olefin, preferably a C3 to C40 -olefin, even more preferably a C3 to Cjg ⁇ -olefin, even more preferably a C3 to a Ci 2 ⁇ -olefin.
  • the ethylene polymer has a molecular weight distribution (Mw/Mn) of 4 or less, preferably 3 or less, even more preferably 2 or less, even more preferably between 2 and 1.
  • the ethylene copolymer has a Composition Distribution Breadth Index (CDBI)of 50 % or more, preferably 60% or more, even more preferably 70% or more, even more preferably 80% or more, even more preferably 90% or more.
  • Composition Distribution Breadth Index (CDBI) is a measure of the composition distribution of monomer within the polymer chains and is measured by the procedure described in PCT publication WO 93/03093, published February 18, 1993 including that fractions having a weight average molecular weight (Mw) below 15,000 are ignored when determining CDBI.
  • the ethylene copolymer prior to grafting may have an Melt Index of 150 g/lOmin or less, preferably 20 g/lOmin or less, even more preferably 10 g/lOmin or less, even more preferably 5 g lOmin or less.
  • the ethylene copolymer prior to grafting has a number average molecular weight of 10,000 or more, more preferably 20,000 or more even more preferably 30,000 or more, even more preferably between 30,000 and 150,000.
  • the ethylene copolymer prior to grafting has a ratio of methylenes to tertiary carbon atoms of 18 or less, more preferably 17 or less. In a particularly preferred embodiment the ratio is 18 or less and the alpha-olefin is a C3 to C6 alpha-olefin, preferably butene, pentene, or hexene.
  • the grafted ethylene copolymer has a number of unsaturated acid or anhydride molecules per chain of 2 or more as calculated according to the following formula: [Mn* UAA (wt%)] / [UAA(Mw)] wherein Mn is the number average molecular weight as measured by GPC, UAA(wt%) is the weight percent of the unsaturated acid or anhydride as measured by FTIR spectroscopy and UAA(Mw) is the molecular weight of the unsaturated acid or anhydride, preferably 3 or more, even more preferably 5 or more, even more preferably 10 or more.
  • the ethylene copolymer further comprises an unsaturated acid or anhydride.
  • unsaturated acid or anhydride include any unsaturated organic compound containing at least one double bond and at least one carbonyl group.
  • Representative acids include carboxylic acids, anhydrides, esters and their salts, both metallic and non-metallic.
  • the unsaturated acid or anhydride is preferably present at about 0.1 weight % to about 20 weight %, preferably at about 0.2 weight % to about 10 weight %, even more preferably at about 0.3 to about 5 weight %, based upon the weight of the ethylene copolymer and the unsaturated acid or anhydride.
  • This invention can also be practiced with any unsaturated monomer which can be grafted in a reaction with peroxide.
  • Ethylene copolymers useful herein can be produced by the methods described in US 5,055,438; US 5,507,475; US 5,096,867; US 5,264,405; US 5,324,800; US 5,017,714; U.S.5,240,894; US 5,198,401; US 5,153,157; WO 92 00333; WO 94 03506; EPA 520,732; EPA 129,368; EPA 277,003; EPA 277,004; and CA
  • the ethylene copolymers are produced using one or more mono- or bis-cyclopentadienyl transition metal (preferably group 4) catalysts in combination with an activator of alumoxane and/or a non-coordinating anion, preferably in solution, slurry or gas phase.
  • the catalyst may be supported or unsupported and the cyclopentadienyl rings by may substituted or unsubstituted.
  • Unsaturated acid or anhydride content is measured by FTIR (Fourrier Transformed Infrared Spectroscopy).
  • FTIR Frerier Transformed Infrared Spectroscopy
  • the reaction products are compressed at temperature of 165°C into thin films from which infrared spectra were taken using a Mattson
  • the number of unsaturated acid or anhydride (UAA) molecules per polymer chain is obtained by multiplying the total unsaturated acid or anhydride content as measured by FTIR spectroscopy by the number average molecular weight divided by the unsaturated acid or anhydride molecular weight as described in equation: [Mn* UAA (wt%)] / [ UAA(Mw)] wherein Mn is the number average molecular weight as measured by GPC, UAA(wt%) is the weight percent of the unsaturated acid or anhydride as measured by FTIR spectroscopy and UAA(Mw) is the molecular weight of the unsaturated acid or anhydride
  • Unsaturations (vinylidene, vinyls chain end unsaturation, etc) in polyolefins are measured by proton NMR at 125°C. 100 mg of polymer is dissolved in lcc of trichlorobenzene and 0.2 cc of deuterobenzene.
  • the instrument is preferably a VariantTM Unity plus 300 MHz. The following parameters are preferably used: aquisition time: 3 sec, spectral window: 6000 Hz, pulse width: 30°, delay Dl: 5 sec, number of transients: 1024, spinning rate: 17 Hz.
  • Reactivity ratio is measured by the 13 C NMR procedure described in K. Soga, Polymer Bulletin, 1983, Vol 10. pg 168.
  • grafted copolymers described herein include benefits derived from the lower viscosity ratios. Lower ratios translate into more stable operation conditions during processing of the polymers both during manufacturing and processing applications.
  • the grafted polymers of this invention can be used in blends with engineering thermoplastics possessing a functional group susceptible of chemically reacting or interacting through polar interactions or hydrogen bounding with the unsaturated monomer which has been grafted to the backbone.
  • thermoplastics corresponding to this definition are polyamide-6, polyamide-6,6 , polybuthylene terephtalate, polyethylene terephtalate, polycarbonate, polyphenylene oxide, polyphenylene ether, polyoxymethylene, polyvinyl alcohol, ethylene acrylic acid copolymers, ethylene methylacrylate copolymers, ethylene acrylic acid methylacrylate terpolymers and polyvinyl chloride. These polymers can also be used in any of the previous compositions also containing fillers such as silica, talc, calcium carbonate, carbon black or glass fibers.
  • Polymers of this invention can also be used as compatibilizers for blends of polyolefinic polymers and polar thermoplastics as the ones mentionned above. These polymers can be added to polyolefinic compositions containing fillers such as talc, calcium carbonate, silica, carbon black and glass fibers where they will insure increased interaction with the filler and hence higher physical properties. Finally they can serve as adhesion promotors to polar substrates such as polar polymers, metal, aluminium, glass when used pure or in blends with other polyolefinic polymers but also thermoset rubber compounds.
  • Mw and Mn are measured by gel permeation chromotography using monodisperse polystyrene standards on a Waters 150 gel permeation chromatograph (GPC)coupled with a DRI detector and a Chromatix KMX-6 on line light scattering photometer.
  • GPC Waters 150 gel permeation chromatograph
  • EXACTTM 4049 is an ethylene-butene copolymer produced with a single site metallocene catalyst which contains 26 wt% of butene and has a melt index (MI at
  • EXACTTM 4033 is an ethylene butene copolymer containing 21.8 wt% butene and having a melt index (MI at 190°C, 2.16 kg ) of 0.8 g/10 min and a density of 0.88 g/cm 3 .
  • ENGAGETM 8100 is an ethylene octene copolymer containing 35.5 wt% of octene and having a melt index (MI at 190°C, 2.16 kg ) of 1 g/10 min and a density of 0.87 g/cm 3 .
  • ENGAGETM 8200 is an ethylene octene copolymer containing 36.3 wt% of octene and having a melt index (MI at 190°C, 2.16 kg ) of 4.7 g/10 min and a density of 0.87 g/cm 3 .
  • MFR ratio is the ratio of the MFR of the ungrafted copolymer to the MFR of the grafted copolymer.
  • MA maleic anhydride.
  • the polymer and the maleic anhydride were simultaneouysly added to the feed hopper; after melting, the peroxide (Luperox 130) at a 10% concentration in mineral oil was added. Unreacted maleic anhydride and decomposition products of the peroxide are removed with vacuum prior to polymer recovery.
  • the individual experiment proportions of maleic anhydride and peroxide are reported in Table 3.
  • the characteristics of the grafted polymers are reported in Table 4.
  • %MA (total MA content) k (A1790 + A1712)/A4328, k being determined after internal calibration with a series of standards and having a value of 0.258 in this case.
  • the number of unsaturated acid or anhydride molecules per polymer chain is obtained by multiplying the total MA content as measured by FTIR spectroscopy by the number average molecular weight divided by the MA molecular weight as described in equation: [Mn* MA (wt%)] / [ MA(Mw)] wherein the Mn is the number average molecular weight as measured by GPC, MA(wt%) is the weight percent of the maleic anhydride as measured by FTIR spectroscopy and MA(Mw) is the molecular weight of the maleic anhydride.
  • Table 5 reports the characterization for the four ungrafted polymers.
  • the grafted copolymers of this invention achieve a Similar level of grafting with less increase in viscosity versus known polymers. Note that in Figure 1 the copolymers of the invention had a much lower MFR ratio.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

L'invention se rapporte à un copolymère d'éthylène greffé qui comprend de l'éthylène et une alpha-oléfine greffée avec au moins 0,1 % en poids d'un acide ou d'un anhydride insaturés, le copolymère étant caractérisé avant le greffage en ce que: a) le rapport d'insaturation terminale vinylidène/vinyle est inférieur ou égal à 3; et b) on a obtenu un indice de largeur de la répartition de la composition (CDBI) égal ou supérieur à 60 % grâce à l'utilisation d'un ou de plusieurs catalyseurs mono- ou bis- cyclopentadiényle à métaux de transition, en combinaison avec un activateur d'alumoxane et/ou un anion de non-coordination, le copolymère greffé étant caractérisé par un nombre de molécules d'acide ou d'anhydride insaturés par chaîne égal ou supérieur à 2, calculé selon la formule suivante: [Mn*UAA(pds%)]/[UAA(Mw)], dans laquelle Mn est le poids moléculaire moyen en nombre, mesuré par chromatographie par perméation sur gel, UAA(pds%) est le pourcentage en poids de l'acide ou de l'anhydride insaturés, mesuré par spectroscopie à l'infrarouge avec transformation de Fourier, et UAA(Mw) est le poids moléculaire de l'acide ou de l'anhydride insaturés.
PCT/US1998/005552 1997-03-21 1998-03-19 Copolymeres d'ethylene greffes Ceased WO1998042760A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU65753/98A AU6575398A (en) 1997-03-21 1998-03-19 Grafted ethylene copolymers
BR9808027-0A BR9808027A (pt) 1997-03-21 1998-03-19 Copolìmeros grafitizados de etileno
KR1019997008587A KR20010005528A (ko) 1997-03-21 1998-03-19 그라프트된 에틸렌 공중합체
JP54583998A JP2001518137A (ja) 1997-03-21 1998-03-19 グラフトされたエチレンコポリマー
EP98911905A EP0968235A1 (fr) 1997-03-21 1998-03-19 Copolymeres d'ethylene greffes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82183897A 1997-03-21 1997-03-21
US08/821,838 1997-03-21

Publications (1)

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WO1998042760A1 true WO1998042760A1 (fr) 1998-10-01

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PCT/US1998/005552 Ceased WO1998042760A1 (fr) 1997-03-21 1998-03-19 Copolymeres d'ethylene greffes

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EP (1) EP0968235A1 (fr)
JP (1) JP2001518137A (fr)
KR (1) KR20010005528A (fr)
AU (1) AU6575398A (fr)
BR (1) BR9808027A (fr)
WO (1) WO1998042760A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1057867A4 (fr) * 1998-12-18 2003-07-23 Mitsui Chemicals Inc Dispersion de resine, methode de preparation, feuille metallique revetue de resine, et procede de production de stratifie
DE102007043972A1 (de) 2007-09-11 2009-05-20 Kometra Kunststoff-Modifikatoren Und -Additiv Gmbh Verfahren zur Herstellung carboxylierter Ethylenpolymerblends
DE102008019804A1 (de) 2008-04-15 2009-10-22 Kometra Kunststoff-Modifikatoren Und -Additiv Gmbh Funktionalisierte Ethylenpolymere mit hohem Haftvermögen und Verfahren zu ihrer Herstellung
WO2014146773A1 (fr) 2013-03-20 2014-09-25 Byk Kometra Gmbh Procédé de production d'élastomères thermoplastiques fonctionnalisés
US9120888B2 (en) 2006-06-15 2015-09-01 Dow Global Technologies Llc Functionalized olefin interpolymers, compositions and articles prepared therefrom and methods for making the same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5310806A (en) * 1991-05-22 1994-05-10 Quantum Chemical Corporation Process for preparing an ethylene-unsaturated polycarboxylic compound graft copolymer
WO1996028486A1 (fr) * 1995-03-13 1996-09-19 Basf Aktiengesellschaft Copolymeres d'acides dicarboxyliques insatures ou de leurs anhydrides et oligoolefines a terminaison vinylique ainsi que leurs produits de reaction avec des agents nucleophiles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5310806A (en) * 1991-05-22 1994-05-10 Quantum Chemical Corporation Process for preparing an ethylene-unsaturated polycarboxylic compound graft copolymer
WO1996028486A1 (fr) * 1995-03-13 1996-09-19 Basf Aktiengesellschaft Copolymeres d'acides dicarboxyliques insatures ou de leurs anhydrides et oligoolefines a terminaison vinylique ainsi que leurs produits de reaction avec des agents nucleophiles

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1057867A4 (fr) * 1998-12-18 2003-07-23 Mitsui Chemicals Inc Dispersion de resine, methode de preparation, feuille metallique revetue de resine, et procede de production de stratifie
US6833045B1 (en) 1998-12-18 2004-12-21 Mitsui Chemicals, Inc. Resin dispersion, method of preparing the same, resin-coated metal sheet obtained with the same, and process for producing laminate
US9120888B2 (en) 2006-06-15 2015-09-01 Dow Global Technologies Llc Functionalized olefin interpolymers, compositions and articles prepared therefrom and methods for making the same
US9902882B2 (en) 2006-06-15 2018-02-27 Dow Global Technologies Llc Functionalized olefin interpolymers, compositions and articles prepared therefrom, and methods for making the same
DE102007043972A1 (de) 2007-09-11 2009-05-20 Kometra Kunststoff-Modifikatoren Und -Additiv Gmbh Verfahren zur Herstellung carboxylierter Ethylenpolymerblends
US8742016B2 (en) 2007-09-11 2014-06-03 Dow Global Technologies Llc Method for producing carboxylated ethylene polymer blends
DE102008019804A1 (de) 2008-04-15 2009-10-22 Kometra Kunststoff-Modifikatoren Und -Additiv Gmbh Funktionalisierte Ethylenpolymere mit hohem Haftvermögen und Verfahren zu ihrer Herstellung
WO2014146773A1 (fr) 2013-03-20 2014-09-25 Byk Kometra Gmbh Procédé de production d'élastomères thermoplastiques fonctionnalisés
US10189933B2 (en) 2013-03-20 2019-01-29 Byk-Chemie Gmbh Method for producing functionalized thermoplastic elastomers

Also Published As

Publication number Publication date
EP0968235A1 (fr) 2000-01-05
BR9808027A (pt) 2000-03-08
JP2001518137A (ja) 2001-10-09
KR20010005528A (ko) 2001-01-15
AU6575398A (en) 1998-10-20

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