CH366973A - Process for improving the dye affinity of non-textile articles made from linear, high molecular weight polymers of α-olefins - Google Patents
Process for improving the dye affinity of non-textile articles made from linear, high molecular weight polymers of α-olefinsInfo
- Publication number
- CH366973A CH366973A CH6811159A CH6811159A CH366973A CH 366973 A CH366973 A CH 366973A CH 6811159 A CH6811159 A CH 6811159A CH 6811159 A CH6811159 A CH 6811159A CH 366973 A CH366973 A CH 366973A
- Authority
- CH
- Switzerland
- Prior art keywords
- improving
- linear
- molecular weight
- olefins
- high molecular
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 229920006158 high molecular weight polymer Polymers 0.000 title claims description 5
- 239000004753 textile Substances 0.000 title claims description 4
- 239000004711 α-olefin Substances 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 9
- MJKIORXNEJFOPX-UHFFFAOYSA-N 2-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=CC=CC=N1 MJKIORXNEJFOPX-UHFFFAOYSA-N 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- -1 polypropylene Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- WWDWPSQOAUMNDT-UHFFFAOYSA-N 3-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=CC=CN=C1 WWDWPSQOAUMNDT-UHFFFAOYSA-N 0.000 claims description 2
- MPMPYHKTFSOUHU-UHFFFAOYSA-N 4-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=CC=NC=C1 MPMPYHKTFSOUHU-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- YZTZERJXOAGCKU-UHFFFAOYSA-N 3-methyl-2-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=NC=CC=C1C YZTZERJXOAGCKU-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JROURLWMOZCGJV-UHFFFAOYSA-N alizarin blue Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C1=CC=CN=C1C(O)=C2O JROURLWMOZCGJV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JBTHDAVBDKKSRW-UHFFFAOYSA-N chembl1552233 Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 JBTHDAVBDKKSRW-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class 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
- 125000002081 peroxide group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/26—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers modified by chemical after-treatment
- C08J2323/30—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers modified by chemical after-treatment by oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Verfahren zur Verbesserung der Farbstoffaffinität von nichttextilen Gegenständen aus linearen, hochmolekularen Polymeren von a-Olefinen
Die vorliegende Erfindung bezieht sich auf ein 'rfahren zur Verbesserung der Affinität von nicht estilen Gegenständen aus linearen hochmolekularen Polymeren von a-Olefinen gegenüber Farbstoffen lurch Aufpfropfen von Polymerketten, welche die notwendigen reaktionsfähigen sauren oder basischen Gruppen liefern können, auf solche Gegenstände.
Ein Verfahren dieser Art ist in der Patentschrift Nr. 361126 beschrieben.
Es ist bekannt, dass die geringe Farbstoffaffinität on Gegenständen aus Polyolefinen im wesentlichen uf das Fehlen von reaktionsfähigen Gruppen, welche X erschiedene Substanzen chemisch binden können, zurückzuführen ist. Gemäss der in der obigen Patentschrift beschriebenen Erfindung wird diese Schwie rigkeit übenvunden durch Aufpfropfen von Polymeren von verschiedenen Monomeren, wie Vinylestern stickstoffhaltigen Vinylmonomeren, basischen Xcnlaten und Derivaten von Maleinsäureanhydrid und Acrylsäure, auf die Gegenstände.
Die vorliegende Erfindung sieht nun ein Verfahren zur Verbesserung der Farbaffinität von nichttextilen Artikeln aus linearen, hochmolekularen Polymeren von a-Olefinen vor, welches dadurch gekennzeichnet ist, dass auf das vorher peroxydierte Polymer solche Polymerketten aufgepfropft werden, welche sich von heterocyclischen. stickstoffhaltigen Monomeren ableiten, die wenigstens eine Isopropenylgruppe enthalten. Das erfindungsgemässe Verfahren ist besonders geeignet für Gegenstände aus linearem, hochmolekularem kristallinem Polypropylen.
Vorzugsweise werden Isopropenylpyridine ver endet, und zwar 2-, 3- und 4-lsopropenylpyridin, sowie solche Isopropenylpyridine, welche am heterocyclischen Ring Methylgruppen tragen.
Das Aufpfropfen kann in gasförmiger Phase oder in Lösung in einem geeigneten Lösungsmittel, vorzugsweise in einem sauerstofffreien Medium, an den Gegenständen durchgeführt werden, welche Peroxyd- oder Hydroperoxydgruppen enthalten können.
Das Monomer kann allein oder zusammen mit einem anderen polymerisierbaren Monomer, wie Acrylnitril, Styrol oder SIethacrylat, verwendet werden.
Wenn die Pfropfpolymerisation beendet ist, ist es zweckmässig, die Gegenstände sorgfältig mit Lösungsmitteln zu waschen, welche die geringen Mengen von zurückgebliebenem unpolymerisiertem Monomer und alles nicht aufgepfropfte Polymer zu entfernen vermögen. Nach dem Trocknen können sie dann gefärbt und fertiggestellt werden.
Beispiel
10 g eines in biaxialer Richtung gestreckten, 25, je dicken Polypropylenfilms, welcher aus einem Polymer mit einer Grenzviskosität von 2,05, einem Aschengehalt von 0,0150,10, einem Rückstand nach der Heptanextraktion von 96,70/0 besteht, werden in einem ventilierten Ofen 4 Stunden lang auf 95o C erhitzt, bis ein Peroxydgruppengehalt von 0,25 O/o erreicht ist.
Der peroxydierte Film wird dann in einem evakuierten, auf 80O C erhitzten Reaktionsgefäss aufgehängt, welches eine Mischung von 10 g Isopropenylpyridin und 10g Acrylnitril enthält.
Nach 4 Stunden wird der Film aus dem Reaktionsgefäss entnommen, zunächst mit verdünnter Schwefelsäure bei 900 C und dann mit einer siedenden Ben zol-Aceton-(5O50)-Mischung gewaschen. Die prozentuale Gewichtserhöhung des Films beträgt 8,5 0/o.
Der so behandelte Film zeigt eine Affinität gegenüber folgenden sauren Wollfarbstoffen:
Diachromgelb R. C., Wollrot B, Alizarinblau ACF.
Process for improving the dye affinity of non-textile articles made from linear, high molecular weight polymers of α-olefins
The present invention relates to a process for improving the affinity of non-stable objects made of linear high molecular weight polymers of α-olefins for dyes by grafting onto such objects polymer chains which can provide the necessary reactive acidic or basic groups.
A method of this type is described in Patent Specification No. 361126.
It is known that the low dye affinity of articles made of polyolefins is essentially due to the lack of reactive groups which can chemically bind various substances. According to the invention described in the above patent, this difficulty is overcome by grafting polymers of various monomers, such as vinyl esters, nitrogen-containing vinyl monomers, basic xcnlates and derivatives of maleic anhydride and acrylic acid, onto the articles.
The present invention now provides a method for improving the color affinity of non-textile articles made of linear, high molecular weight polymers of α-olefins, which is characterized in that such polymer chains are grafted onto the previously peroxidized polymer, which differ from heterocyclic. Derive nitrogen-containing monomers which contain at least one isopropenyl group. The method according to the invention is particularly suitable for articles made of linear, high molecular weight crystalline polypropylene.
Isopropenylpyridines are preferably terminated, namely 2-, 3- and 4-isopropenylpyridine, as well as those isopropenylpyridines which carry methyl groups on the heterocyclic ring.
The grafting can be carried out in the gaseous phase or in solution in a suitable solvent, preferably in an oxygen-free medium, on the objects which may contain peroxide or hydroperoxide groups.
The monomer can be used alone or together with another polymerizable monomer such as acrylonitrile, styrene, or methacrylate.
When the graft polymerization is complete, it is advisable to wash the items carefully with solvents which are capable of removing the small amounts of remaining unpolymerized monomer and any ungrafted polymer. Once dry, they can then be colored and finished.
example
10 g of a 25, each thick polypropylene film stretched in the biaxial direction, which consists of a polymer with an intrinsic viscosity of 2.05, an ash content of 0.0150.10, a residue after the heptane extraction of 96.70 / 0, are in heated in a ventilated oven for 4 hours at 95o C until a peroxide group content of 0.25% is reached.
The peroxidized film is then suspended in an evacuated reaction vessel heated to 80 ° C. which contains a mixture of 10 g of isopropenylpyridine and 10 g of acrylonitrile.
After 4 hours, the film is removed from the reaction vessel, washed first with dilute sulfuric acid at 900 C and then with a boiling benzene-acetone (5050) mixture. The percentage increase in the weight of the film is 8.5%.
The film treated in this way shows an affinity for the following acidic wool dyes:
Diachrome yellow R.C., wool red B, alizarin blue ACF.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT36658 | 1958-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH366973A true CH366973A (en) | 1963-01-31 |
Family
ID=11098653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6811159A CH366973A (en) | 1958-01-10 | 1959-01-08 | Process for improving the dye affinity of non-textile articles made from linear, high molecular weight polymers of α-olefins |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH366973A (en) |
| ES (1) | ES246418A2 (en) |
-
1959
- 1959-01-08 CH CH6811159A patent/CH366973A/en unknown
- 1959-01-09 ES ES0246418A patent/ES246418A2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES246418A2 (en) | 1959-06-16 |
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