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US3274312A - Process for preparing dye-receptive shaped articles - Google Patents

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US3274312A
US3274312A US244943A US24494362A US3274312A US 3274312 A US3274312 A US 3274312A US 244943 A US244943 A US 244943A US 24494362 A US24494362 A US 24494362A US 3274312 A US3274312 A US 3274312A
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mix
dye
shaped articles
fibers
prepared
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US244943A
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Compostella Mario
Latella Giovanni
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Montedison SpA
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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/04—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyolefins
    • 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
    • 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
    • C08L23/10—Homopolymers or copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/12—Applications used for fibers

Definitions

  • the present invention relates to a process for preparing dye-receptive shaped articles such as textile fibers, films, sheets, tapes, etc., from alpha-olefin polymers.
  • Processes used for obtaining, for example, textile fibers comprise:
  • any suitable continuous or discontinuous apparatus capable of supplying heat may be employed for the sintering step.
  • 150% of polycondensate may be mixed with 50-99% of polyolefin.
  • the method of the present invention more particularly, 1
  • polyolefins and basic nitrogen polycondensates obtained by reacting (in the presence or absence of solvents and condensing agents) (1) epichlorohydrin, (2) one or more primary C C or secondary C C aliphatic amines and then subjecting the condensation product to a further condensation with one or more aliphatic, aromatic or heterocyclic secondary diamines.
  • These condensates show generally a softening point under C., an intrinsic viscosity (determined in a 1% isopropanol solution) of 005-05 and a nitrogen content up to 35%.
  • the shaped articles such as fibers are then prepared by extruding the granules sintered according to the invention.
  • the mixes to be extruded contain polyolefins, from 1 to 25% by weight of the nitrogen polycondensate and, if desired, 0.1 to 5% of a solid dispersing agent for dispersing the nitrogen condensate in the molten mass.
  • Suitable solid dispersing agents include: cetyl and stearyl alcohols, stearic acid, benzoin, furoin, vinyl stearate, mono-, dior tristearic esters of glycerol, monoethanolamine stearate, stearic amide, C to C aliphatic amines, condensation products of ethylene oxide with alcohols, amines or phenols, polystearamide, polyacrylic acid, polystyrene, styrene copolymers, terpene polymers, etc.
  • the sintering and spinning operations according to the present invention may be conveniently carried out under oxygen-free nitrogen.
  • the fibers produced may be in the form of monoor pluro-filaments and can be employed for preparing continuous fibers or staples or for preparing either bulky yarns or staples.
  • the monoor plum-filaments prepared according to the present invention can be subjected to treatments for the water-insolubilization of the basic nitrogen compound.
  • Particularly useful for this purpose are the treatments with formaldehyde, diisocyanates, diepoxy compounds or various cross-linking agents such as divinyl benzene or the like. These treatments may be carried out either before or after stretching.
  • the stretching is preferably executed using ratios between 1:2 and 1:10 at temperatures between 80 and C. in stretching devices heated with hot air, steam or similar fluids.
  • the fibers thus obtained can be dyed with acid dyes or with plastosoluble dyes. They also exhibit a good aflinity for basic and vat dyestuffs.
  • the sintered granules prepared according to the present invention are also suitable for extrusion into films, tapes and various other shaped articles.
  • Stereospecific catalysts such as those disclosed by Natta et a1. or shown in Italina Patent 526,101, are examples of suitable catalysts.
  • Shaped articles, especially fibers obtained from polyproylene containing predominant amounts (more than 50%) of isotactic macromolecules are of particular interest.
  • the residue of the heptane extraction is an indication of the presence of isotactic macromolecules.
  • Example 1 A mix is prepared from:
  • the mix is then sintered in a machine for preparing tablets.
  • the residence time of the mix in the sintering machine is 1 second, and this device reaches a temperature of 90 C.
  • the sintered granules are then spun in a melt spinning device under the following conditions:
  • Screw temperature C. 250 Head temperature
  • Acid black JVS Acid dye Lanasyn red 2GL Metallized dye. Setacyl yellow 3G Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquinone blue RHO Plastosoluble dye.
  • Example 2 A mix is prepared from:
  • the mix is then sintered in a device for the preparation of tablets.
  • the residence time of the mix in the sinterization device is 1 second and the mix reaches a temperature of 100 C.
  • the sintered granules are spun in a melt spinning device under the following conditions:
  • Screw temperature C. 260 Head temperature
  • C. 265 Spinneret temperature C. 265 Spinneret type
  • mm 198 x 0.8 x 16 Maximum pressure, kg./cm. 100
  • the fibers thus prepared have a clear color and their residual intrinsic viscosity amounts to of the initial value.
  • the fibers after being stretched at 130 C. inthe presence of steam with a stretching ratio of 1:5, exhibit the following serimetric characteristics:
  • Acid black IVS Acid dye Lanasyn red 2G1 Metallized dye. Setacyl yellow 3G Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquinone blue Plastosoluble dye.
  • Example 3 A mix is prepared from:
  • the mixture is then sintered in a device for the preparation of pellets using a residence time in the sintering device of 1 sec.
  • the mix is heated to a temperature of 80 C. in this device.
  • the centered granules are spun in a melt spinning device under the following conditions:
  • Acid black IVS Acid dye Lanasyn red 26L Metallized dye. Setacyl yellow 36 Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquino-ne blue RHO Plastosoluble dye.
  • the basic nitrogen polycondensate is prepared by reacting 1 mol of a compound from (a), 1 to 3 mols of epichlorohydrin and 0.1 to 10 mols of a bissecondary diamine from (c).
  • the amine of (a) is selected from the group consisting of n-dodecylamine, hexadecylamine, octadecylamine, dioctadecylamine, dioctylamine or salts thereof.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

United States Patent Office 3,274,312 Patented Sept. 20, 1966 3,274,312 PROCESS FOR PREPARING DYE-RECEPTIVE SHAPED ARTICLES Mario Compostelia, Emanuele Del Mauro, and Giovanni Latella, Terni, Italy, assignors to Montecatini Societa IGelnerale per llndustria Mineraria e Chimica, Milan,
ta y No Drawing. Filed Dec. 17, 1962, Ser. No. 244,943 Claims priority, application Italy, Dec. 21, 1961,
22,809/ 61 7 Claims. (Cl. 26478) The present invention relates to a process for preparing dye-receptive shaped articles such as textile fibers, films, sheets, tapes, etc., from alpha-olefin polymers.
In the applicants US. patent applications Ser. No. 30,732, now abandoned, No. 124,346 and No. 212,119 there has been described a process for preparing basic nitrogen polycondensates by reacting (in the presence or absence of solvents and condensing agents) one or more primary C C or secondary C -C aliphatic amines with epichlorohydrin, this first condensation being followed by a further condensation with one or more aliphatic, aromatic or heterocyclic-bis secondary diamines.
The preparation of shaped articles including textile fibers from mixes containing these polycondensates and of polyolefins prepared with the aid of stereospecific catalysts (see, for example, Italian Patent No. 526,101), more particularly polypropylene has also been described in the above applications.
Processes used for obtaining, for example, textile fibers, in general, comprise:
(1) Mixing the polycondensate (for example, 125% with respect to the total mix) with the polyolefin, employing any conventional known procedure;
(2) Granulating the mix obtained according to 1), in a screw device at temperatures of 170300 C., in order to render the mix suitable for feeding into spinning devices; (it being known that the use of rough powdered mixtures, in fact, make the feeding operation irregular and therefore detrimentally affects the spinning step);
(3) The extrusion of the resulting granulate in a melt spinning device through spinnerets having holes with a length/ diameter ratio preferably higher than 1, and winding the spinning filament;
(4) Stretching and spinning the filaments obtained in (3).
Various polycondensates, however, when they are subjected to the drastic thermal treatment needed for the granulation and spinning (stages 2 and 3 above) are altered thereby exhibiting a decrease in their molecular weight and a certain discoloration.
It has been now surprisingly found according to the present invention, that the thermal decomposition of dyeable basic nitrogen polycondensates can be avoided by eliminating the mix granulation stage, and, by sintering the polycondensate-polyolefin mix at temperatures between 20 and 170 C.
By carrying out this procedure, it is possible to obtain the mixes in the form of granules which can be fed to the spinning screws in a regular and homogeneous manner and which do not easily disintegrate.
In order to produce these sintered granules, any suitable continuous or discontinuous apparatus capable of supplying heat may be employed for the sintering step.
In the preparation of dyeable textile fibers from crystalline polyolefins, such as polypropylene containing predominant amounts (more than 50%) of isotactic macromolecules, it is convenient to prepare a mix rich in the basic nitrogen polycondensate, and then sinter this mix. Subsequently the polycondensate-rich granules are extruded or spun after adding thereto the amount of granular polyolefin needed to achieve the desired amount of polycondensates in the textile fibers.
According to the present invention, 150% of polycondensate may be mixed with 50-99% of polyolefin.
The method of the present invention, more particularly, 1
may be applied to mixes of polyolefins and basic nitrogen polycondensates obtained by reacting (in the presence or absence of solvents and condensing agents) (1) epichlorohydrin, (2) one or more primary C C or secondary C C aliphatic amines and then subjecting the condensation product to a further condensation with one or more aliphatic, aromatic or heterocyclic secondary diamines. These condensates show generally a softening point under C., an intrinsic viscosity (determined in a 1% isopropanol solution) of 005-05 and a nitrogen content up to 35%.
Mixes of polypropylene with polycondensates of octodecylamine, epichlorohydrin and piperazine are of particular interest.
The shaped articles such as fibers are then prepared by extruding the granules sintered according to the invention. The mixes to be extruded contain polyolefins, from 1 to 25% by weight of the nitrogen polycondensate and, if desired, 0.1 to 5% of a solid dispersing agent for dispersing the nitrogen condensate in the molten mass. Suitable solid dispersing agents include: cetyl and stearyl alcohols, stearic acid, benzoin, furoin, vinyl stearate, mono-, dior tristearic esters of glycerol, monoethanolamine stearate, stearic amide, C to C aliphatic amines, condensation products of ethylene oxide with alcohols, amines or phenols, polystearamide, polyacrylic acid, polystyrene, styrene copolymers, terpene polymers, etc.
The sintering and spinning operations according to the present invention may be conveniently carried out under oxygen-free nitrogen.
The fibers produced may be in the form of monoor pluro-filaments and can be employed for preparing continuous fibers or staples or for preparing either bulky yarns or staples.
The monoor plum-filaments prepared according to the present invention can be subjected to treatments for the water-insolubilization of the basic nitrogen compound. Particularly useful for this purpose are the treatments with formaldehyde, diisocyanates, diepoxy compounds or various cross-linking agents such as divinyl benzene or the like. These treatments may be carried out either before or after stretching.
The stretching is preferably executed using ratios between 1:2 and 1:10 at temperatures between 80 and C. in stretching devices heated with hot air, steam or similar fluids.
The fibers thus obtained can be dyed with acid dyes or with plastosoluble dyes. They also exhibit a good aflinity for basic and vat dyestuffs.
The sintered granules prepared according to the present invention are also suitable for extrusion into films, tapes and various other shaped articles.
The present invention is applicable topolyolefins, particularly polyolefins prepared by the stereospecific polymerization of alpha-olefins of the formula H H RC=G wherein R is a hydrocarbon radical. Stereospecific catalysts such as those disclosed by Natta et a1. or shown in Italina Patent 526,101, are examples of suitable catalysts. A
Shaped articles, especially fibers obtained from polyproylene containing predominant amounts (more than 50%) of isotactic macromolecules are of particular interest.
The following examples are given to illustrate the present invention without limiting its scope.
All parts and proportions are by weight unless otherwise indicated.
The residue of the heptane extraction is an indication of the presence of isotactic macromolecules.
Example 1 A mix is prepared from:
(1) 100 kg. of polypropylene prepared with the aid of stereospecific catalysts having an intrinsic viscosity [1 of 1.45 (determined in tetrahydronaphthalene as 135 C.), a residue after heptane extraction of 96% and an ash content of 0.01%, and
(2) 5 kg. of a polycondensate prepared by reaction of 0.3 mol of n-octadecylamine with 1.3 mols of epichloro'hydrin and 1 mole of piperazine.
The mix is then sintered in a machine for preparing tablets. The residence time of the mix in the sintering machine is 1 second, and this device reaches a temperature of 90 C.
The sintered granules are then spun in a melt spinning device under the following conditions:
Screw temperature, C. 250 Head temperature, C 260 Spinneret temperature, C 260 Spinneret type, 192 holes with a diameter of 0.8 mm.
and a height of 16 mm. Max pressure (kg/cm?) 100 Winding speed (m./rnin.) 500 The yarns prepared as described have a clear color; and their intrinsic viscosity amounts to 90% of the initial value.
These yarns, after stretching at 130 C. in the presence of steam with a stretching ratio of 1:6 have the following serimetrical characteristics:
Tenacity, g./den. 6 Elongation, percent 20 Immediately after stretching, the yarn is wetted with a 5% aqueous ethylene glycol diglyeydylether solution and then dried.
Upon dyeing these fibers colors, having good intensity and fastness are obtained with the folowing dyes:
Solid yellow 2G Acid dye.
Wool red B Acid dye. Alizarine blue ACF Acid dye.
Acid black JVS Acid dye. Lanasyn red 2GL Metallized dye. Setacyl yellow 3G Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquinone blue RHO Plastosoluble dye.
Example 2 A mix is prepared from:
(1) 100 kg. of polypropylene obtained with the aid of stereospecific catalysts and having an intrinsic viscosity [1 of 1.60 (determined in tetrahydronapthalene at 135 C.), a residue after heptane extraction of 94% and an ash content of 0.010%, and
(2) 5 kg. of the polycondensate prepared by the reaction of 5 mols of n-octadecylamine with 1.5 mols of epichlorohydrin and 1 mole of piperazine.
The mix is then sintered in a device for the preparation of tablets. The residence time of the mix in the sinterization device is 1 second and the mix reaches a temperature of 100 C.
The sintered granules are spun in a melt spinning device under the following conditions:
Screw temperature, C. 260 Head temperature, C. 265 Spinneret temperature, C. 265 Spinneret type, mm 198 x 0.8 x 16 Maximum pressure, kg./cm. 100
Winding speed, m./min. 500
4 The fibers thus prepared have a clear color and their residual intrinsic viscosity amounts to of the initial value.
The fibers, after being stretched at 130 C. inthe presence of steam with a stretching ratio of 1:5, exhibit the following serimetric characteristics:
Tenacity, g./den. 6.5 Elongation, percent 22 Immediately after stretching, the fiber is wetted with a 5% aqueous solution of ethylene glycol diglycidyl ether and is then dried.
Colors having good intensity and fastness are obtained upon dyeing these fibers with the following dyes:
Solid yellow 26 Acid dye.
Wool red B Acid dye. Alizarine blue ACF Acid dye.
Acid black IVS Acid dye. Lanasyn red 2G1 Metallized dye. Setacyl yellow 3G Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquinone blue Plastosoluble dye.
Example 3 A mix is prepared from:
(1) 100 kg. of polypropylene prepared with the aid of stereospecific catalysts and having an intrinsic viscosity of 1.3 (determined in tetrahydronaphtha-lene at 135 C.), a residue after heptane extraction of and an ash content of 0.029, and
(2) 5 kg. of a polycondensate prepared by reaction of 0.4 mol of n-dodecylamine with 1.4 mols of epichlorohydrin and 1 mol of piperazine.
The mixture is then sintered in a device for the preparation of pellets using a residence time in the sintering device of 1 sec. The mix is heated to a temperature of 80 C. in this device.
The centered granules are spun in a melt spinning device under the following conditions:
Screw temperature, C. 240 Head temperature, C. 245 Spinneret temperature, C. 245 Spinneret type 198/0.8 x 16. Max. pressure, kg./cm. Winding speed, m./minute 500 The fibers so obtained are stretched at C. in the presence of steam while employing a stretching ratio of 1:5. The fibers exhibit the following serimetric characteristics:
Tenacity, g./den 5.5
Elongation, per-cent 18 Immediately after stretching, the fibers are wetted with a 25% aqueous ethylene glycol diglycidyl ether solution and dried.
Colors having a good intensity and fastness are obtained lupon dyeing the fibers with the following dyes:
Solid yellow 2G Acid dye. Alizarine bl ue ACF Acid dye.
Acid black IVS Acid dye. Lanasyn red 26L Metallized dye. Setacyl yellow 36 Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquino-ne blue RHO Plastosoluble dye.
group consisting of primary aliphatic amines containing 3-30 carbon atoms and secondary aliphatic amines containing 4-60 canbon atoms, (b) epichloro'hydrin and (c) at least one member selected from the group consisting of aliphatic, aromatic and heterocyclic-bis secondary diamines, and stretching said shaped articles, the improvement which comprises transforming said mix into granules by sintering at a temperature of from 80 C. to about 1170 C. before said extrusion step.
2. The process according to claim 1, wherein the mix which is 'sintered is rich in the nitrogen polycondensates and before extrusion .thereo-f additional amounts of olefin polymer are added to said mix in order to obtain the desired proportions between the polycondensate and the olefin polymer.
3. The process according to claim 1, wherein from 0.1 to 5%, based on the total weight of the mix, of a solid dispersing agent for the nitrogen polyeondensate is also present in said 4. The process according to claim 1, wherein the olefin polymer is polypropylene consisting predominantly of isotactic macromolecules.
5. The process according to claim 1, wherein the basic nitrogen polycondensate is prepared by reacting 1 mol of a compound from (a), 1 to 3 mols of epichlorohydrin and 0.1 to 10 mols of a bissecondary diamine from (c). 6. The process according to claim 1, wherein the amine of (a) is selected from the group consisting of n-dodecylamine, hexadecylamine, octadecylamine, dioctadecylamine, dioctylamine or salts thereof.
7. The process according to claim 1, wherein the secondary diamine of (c) is piperazine.
References Cited by the Examiner ALEXANDER H. B-RODMERKEL, Primary Examiner.
MORRIS LIEBMAN, Examiner.
C. B. HAMBURG, K. W. VERNON, A. L. LEAVITT,
B. SNYDER, Assistant Examiners.

Claims (1)

1. IN THE PROCESS FOR PREPARING DYE-RECEPTIVE SHAPED ARITCLES BY EXTRUDING A MIX CONTAINING (1) AN OLEFIN POLYMER AND (2) A BASIC NITROGEN POLYCONDENSATE, OBTAINED FROM (A) AT LEAST ONE AMINE SELECTED FROM THE GROUP CONSISTING OF PRIMARY ALIPHTIC AMINES CONTAINING 3-30 CARBON ATOMS AND SECONDARY ALIPHATIC AMINES CONTAINING 4-60 CARBON ATOMS, (B) EPICHLOROHYDRIN AND (C) AT LEAST OE MEMBER SELECTED FROM THE GROUP CONSISTING OF ALIPHATIC, AROMATIC AND HETEROCYCLIC-BIS SECONDARY DIAMINES, AND STRETCHING SAID SHAPED ARTICLES, THE IMPROVEMENT WHICH COMORISES TRANSFORMING SAID MIX INTO GRANULES BY SINTERING AT A TEMPERATURE OF FROM 80*C. TO ABOUT 170*C. BEFORE SAID EXTRUSION STEP.
US244943A 1961-12-21 1962-12-17 Process for preparing dye-receptive shaped articles Expired - Lifetime US3274312A (en)

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AT (1) AT241677B (en)
BE (1) BE626339A (en)
DE (1) DE1218655B (en)
DK (1) DK114993B (en)
ES (1) ES283581A1 (en)
FR (1) FR1341351A (en)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917817A (en) * 1971-11-29 1975-11-04 Oreal Hair treating cosmetic compositions containing piperazine based cationic polymer
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945010A (en) * 1956-10-24 1960-07-12 Eastman Kodak Co Preparing polyester fibers of improved dyeability using aromatic amines
FR1245063A (en) * 1958-11-12 1960-11-04 Montedison Spa Improvements in the spinning of viscoelastic polymers
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US3059275A (en) * 1959-04-27 1962-10-23 Clarence W Vogt Method and apparatus for making selfsustaining pellets of plastic materials
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
US3151928A (en) * 1960-05-05 1964-10-06 Montedison Spa Process for improving the tinctorial characteristics of polyolefin fibres

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US2945010A (en) * 1956-10-24 1960-07-12 Eastman Kodak Co Preparing polyester fibers of improved dyeability using aromatic amines
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
FR1245063A (en) * 1958-11-12 1960-11-04 Montedison Spa Improvements in the spinning of viscoelastic polymers
US3059275A (en) * 1959-04-27 1962-10-23 Clarence W Vogt Method and apparatus for making selfsustaining pellets of plastic materials
US3151928A (en) * 1960-05-05 1964-10-06 Montedison Spa Process for improving the tinctorial characteristics of polyolefin fibres

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917817A (en) * 1971-11-29 1975-11-04 Oreal Hair treating cosmetic compositions containing piperazine based cationic polymer
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same

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NL286762A (en) 1900-01-01
DE1218655B (en) 1966-06-08
DK114993B (en) 1969-08-25
GB1006582A (en) 1965-10-06
ES283581A1 (en) 1963-07-01
BE626339A (en) 1900-01-01
AT241677B (en) 1965-08-10
FR1341351A (en) 1963-10-25

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