DE1595112B2 - Verfahren zur herstellung von modifizierten copolymerisaten aus ungesaettigten kohlenwasserstoffen und ungesaettigten carbonsaeuren - Google Patents
Verfahren zur herstellung von modifizierten copolymerisaten aus ungesaettigten kohlenwasserstoffen und ungesaettigten carbonsaeurenInfo
- Publication number
- DE1595112B2 DE1595112B2 DE1965P0036182 DEP0036182A DE1595112B2 DE 1595112 B2 DE1595112 B2 DE 1595112B2 DE 1965P0036182 DE1965P0036182 DE 1965P0036182 DE P0036182 A DEP0036182 A DE P0036182A DE 1595112 B2 DE1595112 B2 DE 1595112B2
- Authority
- DE
- Germany
- Prior art keywords
- carbon
- carbon atoms
- liquid
- copolymer
- diamine
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 title claims 3
- 150000004653 carbonic acids Chemical class 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 239000007788 liquid Substances 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- 150000004985 diamines Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000002002 slurry Substances 0.000 claims 4
- 239000004711 α-olefin Substances 0.000 claims 4
- -1 amine compound Chemical class 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 238000004132 cross linking Methods 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000009826 distribution Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920005648 ethylene methacrylic acid copolymer Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10743—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing acrylate (co)polymers or salts thereof
-
- 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
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing atoms other than carbon or hydrogen
- C08L23/0869—Copolymers of ethene with unsaturated hydrocarbons containing atoms other than carbon or hydrogen with unsaturated acids, e.g. [meth]acrylic acid; with unsaturated esters, e.g. [meth]acrylic acid esters
- C08L23/0876—Salts thereof, i.e. ionomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/31—Ionic cross-link
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S273/00—Amusement devices: games
- Y10S273/22—Ionomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S36/00—Boots, shoes, and leggings
- Y10S36/02—Plastic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/91—Product with molecular orientation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1397—Single layer [continuous layer]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
3 4
R . . 1,36 kg Hexamethylendiamin enthält. Die Copoly-
ispiel merisat-Körner haben eine solche Größe, daß sie
11,34 kg eines Äthylen-Methacrylsäure-Copolymeri- durch ein Sieb mit einer Maschenweite von 0,84 τηττι
sates, das 90 Gewichtsprozent Äthylen und 10 Ge- gehen. Eine Analyse der flüssigen Phase zeigt, daß
wichtsprozent Methacrylsäure enthält und einen 5 nach 2 Stunden 0,65 kg Hexamethylendiamin mit den
Schmelzindex von 5,8 g/10 Min., eine Zerreißfestigkeit Säuregruppen reagiert haben. Das Copolymerisat ist
von 239,1 kg/cm2 und eine Dehnung von 550 % auf- transparenter und zäher als vor der Neutralisation.
weist, schlämmt man in 111,13 kg Methanol auf, das Der Schmelzindex ist im wesentlichen unverändert.
Claims (2)
1. Verfahren zur Herstellung von modifizierten 5 ι ·' ι
Copolymerisaten aus ungesättigten Kohlenwasser- M c r w ·\ Ύ ( r υ \ ss
stoffen und ungesättigten Carbonsäuren durch W-(-C„H2„-m-)-X-(-C„H2re_ro-)-N
Neutralisation von Copolymerisaten aus a-Olefinen ', ',
der Formel RCH = CH2, worin R ein Wasser- K - . K
Stoffatom oder einen Alkylrest mit 1 bis 8 Kohlen- io
Stoffatomen bedeutet, die wenigstens 50 Mol- worin R' Wasserstoffatome oder Alkylreste mit 1 bis
prozent Einheiten des a-Olefins und 0,2 bis 25 Mol- , 5 Kohlenstoffatomen, R" und R"' Wasserstoffatome
Prozent Einheiten von α,/3-ungesättigten Mono- ' oder Alkylreste mit 1 bis 5 Kohlenstoffatomen oder
carbonsäuren mit 3 bis 8 Kohlenstoffatomen zusammen Alkylenreste mit 1 bis 10 Kohlenstoffsowie
gegebenenfalls von anderen polymerisier- 15 atomen, X eine Kohlenstoff-Kohlenstoff-Bindung, ein
baren Monomeren ■ enthalten, mit einem Diamin Sauerstoffatom, ein Schwefelatom, eine Imino- oder
der allgemeinen Formel .. . Carbonylgruppe oder einen Phenylrest, m 0 bis 4
und η wenigstens 1 bedeutet, oder dessen Ammoniumsalz neutralisiert werden. ', ,
R R 20 Gemäß Hauptpatent 1520 518 kann die Ver- j
I I netzung durchgeführt werden, indem man das Carbon- '
N—(—CnHon-m—)—X—(—CjiH2ji-j»—)—N säuregruppen enthaltende Copolymerisat mit der Di- (jrtr
I I amin-Verbindung schmelzmischt oder das Diamin R' R' direkt oder in gelöster Form einer Lösung der Copoly-
25 merisat-Grundlage zusetzt und nach der Umsetzung
das erhaltene Copolymerisat isoliert.
worin R' Wasserstoffatome oder Alkylreste mit Gegenstand der Erfindung -ist ein verbessertes Ver-
1 bis 5 Kohlenstoffatomen, R" und R'" Wasser- ;: ,fahren, das sich dadurch kennzeichnet, daß man die
Stoffatome oder Alkylreste mit 1 bis 5 Kohlenstoff- Polymerisatteilchen in einer Flüssigkeit aufschlämmt,
atomen oder zusammen Alkylenreste mit 1 bis 30 in welcher die mit den Carbonsäuregruppen reagie-10
Kohlenstoffatomen, X eine Kohlenstoff-Kohlen- rende Diamin-Komponente enthalten ist. " .
stoff-Bindung, ein Sauerstoffatom, ein Schwefel- Die Diaminkonzentration in der. Flüssigkeit beträgt
stoff-Bindung, ein Sauerstoffatom, ein Schwefel- Die Diaminkonzentration in der. Flüssigkeit beträgt
atom, eine Imino- oder Carbonylgruppe oder vorzugsweise das zwei- bis vierfache derjenigen Menge,
einen Phenylrest,r m 0 bis 4 und η wenigstens* 1" die stöchiometrisch zur Neutralisation einer.vorher
.. . bedeutet, oder dessen Ammoniumsalz, nach Patent 35 festgelegten Menge an Carbonsäuregruppen des Co-1
520 518, dadurch gekennzeichnet, polymerisates, die über 10% liegt» notwendig ist.
daß man die Polymerisatteilchen in einer Flüssig- Als a-Olefin der Formel RCH = CH2 in den Co-
daß man die Polymerisatteilchen in einer Flüssig- Als a-Olefin der Formel RCH = CH2 in den Co-
keit aufschlämmt, welche die mit den Carbonsäure- . polymerisaten verwendet man vorzugsweise Äthylen,
gruppen reagierende Diamin-Komponente enthält. Propylen, Buten-(l), Penten-(1), Hexen(l), Hepten-(1),
2. Verfahren nach Anspruch 1, dadurch gekenn- 40 3-Methylbuten-(l) und 4-Methylbuten-(l).
zeichnet, daß man als Flüssigkeit Wasser einsetzt Die Temperatur der Aufschlämmung liegt vorzugs-
zeichnet, daß man als Flüssigkeit Wasser einsetzt Die Temperatur der Aufschlämmung liegt vorzugs-
;,und die Vernetzung bei einer Temperatur zwischen . weise zwischen 50 und 1000C. Die höheren Tempera-"
50 und 1000C durchführt. türen innerhalb dieses Bereiches begünstigen eine ν
schnellere Neutralisation, aber auch eine stärkere Y
45- Flüssigkeitsabsorption durch das Copolymerisat.
Die zum Aufschlämmen verwendete Flüssigkeit kann jedes beliebige Lösungsmittel für das Kationen
liefernde Material sein; geeignete Lösungsmittel sind
' ■ * " Wasser, das bevorzugt wird, niedere aliphatische
50 Alkohole, beispielsweise Methanol, Äthanol, Propanol und Butanol und Mischungen dieser niederen aliphatischen
Alkohole untereinander und/oder mit Wasser.
Das Hauptpatent 1 520 518 betrifft ein Verfahren Die Reaktionszeit hängt von der Temperatur, der
zur Herstellung von modifizierten Copolymerisaten Kationen-Konzentration, der Korngröße des Copolyaus
ungesättigten Kohlenwasserstoffen und ungesättigr 55 merisates und dem gewünschten Neutralisationsgrad
ten Carbonsäuren durch Neutralisation der wenigstens ab; die Zeit beträgt im allgemeinen 30 Minuten bis
teilweise in ionisierter Form — COO — vorliegenden 8 Stunden.
Carboxylgruppen der Copolymerisate mit mehrwerti- Die Korngröße des Copolymerisates ist nicht kri-
gen Aminen mit wenigstens 2 Kohlenstoffatomen bei tisch, bevorzugt wird jedoch eine Korngröße von etwa
höchstens 3000C und Bedingungen, die eine homogene 60 0,15 bis 4,76 mm.
Verteilung ermöglichen, das dadurch gekennzeichnet In der Aufschlämmung liegt das Copolymerisat in
ist, daß Copolymerisate aus a-Olefinen der Formel einer Menge vor, die 10 bis 40 Gewichtsprozent, be-RCH
= CH2, worin R ein Wasserstoffatom oder einen zogen auf die Aufschlämmung, ausmacht.
Alkylrest mit 1 bis 8 Kohlenstoffatomen bedeutet, die Da etwas Flüssigkeit von den Copolymerisat-
Alkylrest mit 1 bis 8 Kohlenstoffatomen bedeutet, die Da etwas Flüssigkeit von den Copolymerisat-
wenigstens 50 Molprozent Einheiten des a-OIefins und 65 körnern adsorbiert wird, muß diese daraus wieder ent- j
0,2 bis 25 Molprozent Einheiten von α,/3-ungesättigten fernt werden. Dies kann man zweckmäßig mit Hilfe j
Monocarbonsäuren mit 3 bis 8 Kohlenstoffatomen eines Extraktionsextruders erreichen, in welchem die
sowie gegebenenfalls von anderen polymerisierbaren Flüssigkeit verdampft wird.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13514761A | 1961-08-31 | 1961-08-31 | |
| US16883962A | 1962-01-25 | 1962-01-25 | |
| US27147763 US3264272A (en) | 1961-08-31 | 1963-04-08 | Ionic hydrocarbon polymers |
| US34829364 US3404134A (en) | 1961-08-31 | 1964-02-28 | Process of crosslinking polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1595112A1 DE1595112A1 (de) | 1970-04-09 |
| DE1595112B2 true DE1595112B2 (de) | 1973-07-05 |
| DE1595112C3 DE1595112C3 (de) | 1974-03-14 |
Family
ID=27495141
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962P0030096 Pending DE1520506B2 (de) | 1961-08-31 | 1962-08-27 | Verfahren zum modifizieren von carboxylgruppen enthaltenden aethylenpolymeren |
| DE1963P0031004 Pending DE1520518B2 (de) | 1961-08-31 | 1963-01-24 | Verfahren zur herstellung von modifizierten copolymerisaten aus ungesaettigten kohlenwasserstoffen und ungesaettigten carbonsaeuren |
| DE1520601A Granted DE1520601B2 (de) | 1961-08-31 | 1964-04-08 | Verfahren zum Modifizieren von Carboxylgruppen enthaltenden Äthylenpolymeren |
| DE1595112A Expired DE1595112C3 (de) | 1961-08-31 | 1965-03-01 | Verfahren zur Herstellung von modifizierten Copolymerisaten aus ungesättigten Kohlenwasserstoffen und ungesättigten Carbonsäuren |
| DE1965P0036183 Granted DE1745938B2 (de) | 1961-08-31 | 1965-03-01 | Verfahren zum modifizieren von carboxylgruppen enthaltenden aethylenpolymeren |
| DE1745939A Expired DE1745939C3 (de) | 1961-08-31 | 1965-03-01 | Verfahren zum Modifizieren von Carboxylgruppen enthaltenden Äthylenpolymeren |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962P0030096 Pending DE1520506B2 (de) | 1961-08-31 | 1962-08-27 | Verfahren zum modifizieren von carboxylgruppen enthaltenden aethylenpolymeren |
| DE1963P0031004 Pending DE1520518B2 (de) | 1961-08-31 | 1963-01-24 | Verfahren zur herstellung von modifizierten copolymerisaten aus ungesaettigten kohlenwasserstoffen und ungesaettigten carbonsaeuren |
| DE1520601A Granted DE1520601B2 (de) | 1961-08-31 | 1964-04-08 | Verfahren zum Modifizieren von Carboxylgruppen enthaltenden Äthylenpolymeren |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965P0036183 Granted DE1745938B2 (de) | 1961-08-31 | 1965-03-01 | Verfahren zum modifizieren von carboxylgruppen enthaltenden aethylenpolymeren |
| DE1745939A Expired DE1745939C3 (de) | 1961-08-31 | 1965-03-01 | Verfahren zum Modifizieren von Carboxylgruppen enthaltenden Äthylenpolymeren |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3264272A (de) |
| BE (2) | BE621846A (de) |
| CH (2) | CH445861A (de) |
| DE (6) | DE1520506B2 (de) |
| DK (1) | DK125713B (de) |
| FR (1) | FR1430478A (de) |
| GB (4) | GB1011981A (de) |
| NL (4) | NL282755A (de) |
| SE (2) | SE311229B (de) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2646425A (en) * | 1953-07-21 | Ereparation of ethylene polymers | ||
| US2607762A (en) * | 1948-12-07 | 1952-08-19 | Monsanto Chemicals | Dry process manufacture of watersoluble derivatives of styrenemaleic anhydride type heteropolymers |
| US2757153A (en) * | 1949-12-14 | 1956-07-31 | Monsanto Chemicals | Process for water-soluble styrenemaleic anhydride derivatives |
| US2599123A (en) * | 1950-08-18 | 1952-06-03 | Du Pont | Copolymers of ethylene with an alkyl acrylate and an alkyl monoester of a butene-1,4-dioic acid |
| US2798053A (en) * | 1952-09-03 | 1957-07-02 | Goodrich Co B F | Carboxylic polymers |
| US2757106A (en) * | 1953-05-28 | 1956-07-31 | Rohm & Haas | Coated paper products and method of making |
| DE1016228B (de) * | 1955-09-06 | 1957-09-26 | Monsanto Chemicals | Verfahren zum Schlichten von Polyamidfaeden oder -garnen |
| US2999056A (en) * | 1956-10-04 | 1961-09-05 | Du Pont | Irradiation bonding of acidic compounds to shaped polymeric structures |
| US3132120A (en) * | 1961-02-03 | 1964-05-05 | Du Pont | Method for the preparation of ethylene copolymers |
| NL288151A (de) * | 1961-08-31 | 1900-01-01 |
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- NL NL288151D patent/NL288151A/xx unknown
- NL NL129542D patent/NL129542C/xx active
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- 1962-08-28 DK DK376862AA patent/DK125713B/da unknown
- 1962-08-29 CH CH1029662A patent/CH445861A/de unknown
- 1962-08-29 SE SE935262A patent/SE311229B/xx unknown
- 1962-08-30 GB GB3328162A patent/GB1011981A/en not_active Expired
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1963
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- 1963-01-24 DE DE1963P0031004 patent/DE1520518B2/de active Pending
- 1963-01-24 CH CH90163A patent/CH435741A/de unknown
- 1963-01-25 SE SE83063A patent/SE303882B/xx unknown
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1964
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- 1965-02-26 GB GB840765A patent/GB1063436A/en not_active Expired
- 1965-03-01 DE DE1595112A patent/DE1595112C3/de not_active Expired
- 1965-03-01 DE DE1965P0036183 patent/DE1745938B2/de active Granted
- 1965-03-01 DE DE1745939A patent/DE1745939C3/de not_active Expired
Also Published As
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|---|---|
| GB1034268A (en) | 1966-06-29 |
| US3404134A (en) | 1968-10-01 |
| FR1430478A (fr) | 1966-03-04 |
| DE1595112C3 (de) | 1974-03-14 |
| GB1029035A (en) | 1966-05-11 |
| US3264272A (en) | 1966-08-02 |
| CH445861A (de) | 1967-10-31 |
| NL282755A (de) | 1900-01-01 |
| DE1745939C3 (de) | 1974-02-21 |
| DE1520506B2 (de) | 1971-06-09 |
| DE1745939B2 (de) | 1973-07-19 |
| BE621846A (de) | 1900-01-01 |
| SE311229B (de) | 1969-06-02 |
| GB1011981A (en) | 1965-12-01 |
| DE1745939A1 (de) | 1971-01-14 |
| BE627537A (de) | 1900-01-01 |
| DE1520601A1 (de) | 1970-05-14 |
| GB1063436A (en) | 1967-03-30 |
| DE1745938A1 (de) | 1971-01-14 |
| SE303882B (de) | 1968-09-09 |
| DE1595112A1 (de) | 1970-04-09 |
| DE1520506A1 (de) | 1970-02-19 |
| DK125713B (da) | 1973-03-26 |
| DE1520601B2 (de) | 1973-01-04 |
| NL129542C (de) | 1900-01-01 |
| DE1745938C3 (de) | 1974-02-21 |
| DE1745938B2 (de) | 1973-07-19 |
| DE1520518A1 (de) | 1969-07-03 |
| CH435741A (de) | 1967-05-15 |
| DE1520518B2 (de) | 1971-07-22 |
| NL128027C (de) | 1900-01-01 |
| NL288151A (de) | 1900-01-01 |
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