US3274312A - Process for preparing dye-receptive shaped articles - Google Patents
Process for preparing dye-receptive shaped articles Download PDFInfo
- Publication number
- 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
- Authority
- US
- United States
- Prior art keywords
- mix
- dye
- shaped articles
- fibers
- prepared
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229920000098 polyolefin Polymers 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000008187 granular material Substances 0.000 claims description 11
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000005245 sintering Methods 0.000 claims description 7
- 150000004985 diamines Chemical group 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 description 22
- 239000000835 fiber Substances 0.000 description 19
- 239000000975 dye Substances 0.000 description 12
- 239000000980 acid dye Substances 0.000 description 11
- -1 aliphatic amines Chemical class 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 238000009987 spinning Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000000707 stereoselective effect Effects 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 238000002074 melt spinning Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000004804 winding Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- BUEWYDIBDQYWNO-UHFFFAOYSA-N 7,12-dihydroxynaphtho[2,3-f]quinoline-5,6-dione Chemical compound Oc1c2C(=O)C(=O)c3ncccc3-c2c(O)c2ccccc12 BUEWYDIBDQYWNO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004234 Yellow 2G Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- FTZLWXQKVFFWLY-UHFFFAOYSA-L disodium;2,5-dichloro-4-[3-methyl-5-oxo-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FTZLWXQKVFFWLY-UHFFFAOYSA-L 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 235000019235 yellow 2G Nutrition 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- XOSCOJBBKOVIOM-UHFFFAOYSA-N 2-aminoethanol;octadecanoic acid Chemical compound NCCO.CCCCCCCCCCCCCCCCCC(O)=O XOSCOJBBKOVIOM-UHFFFAOYSA-N 0.000 description 1
- HKJKONMZMPUGHJ-UHFFFAOYSA-N 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]-6-phenyldiazenylnaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 HKJKONMZMPUGHJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000012840 feeding operation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- MIJRFWVFNKQQDK-UHFFFAOYSA-N furoin Chemical compound C=1C=COC=1C(O)C(=O)C1=CC=CO1 MIJRFWVFNKQQDK-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
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.
Landscapes
- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2280961 | 1961-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3274312A true US3274312A (en) | 1966-09-20 |
Family
ID=11200669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US244943A Expired - Lifetime US3274312A (en) | 1961-12-21 | 1962-12-17 | Process for preparing dye-receptive shaped articles |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3274312A (en)) |
| AT (1) | AT241677B (en)) |
| BE (1) | BE626339A (en)) |
| DE (1) | DE1218655B (en)) |
| DK (1) | DK114993B (en)) |
| ES (1) | ES283581A1 (en)) |
| FR (1) | FR1341351A (en)) |
| GB (1) | GB1006582A (en)) |
| NL (1) | NL286762A (en)) |
Cited By (2)
| 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)
| 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 (fr) * | 1958-11-12 | 1960-11-04 | Montedison Spa | Perfectionnements au filage des polymères viscoélastiques |
| 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 |
-
0
- BE BE626339D patent/BE626339A/xx unknown
- NL NL286762D patent/NL286762A/xx unknown
-
1962
- 1962-12-17 GB GB47432/62A patent/GB1006582A/en not_active Expired
- 1962-12-17 AT AT982462A patent/AT241677B/de active
- 1962-12-17 DE DEM55157A patent/DE1218655B/de active Pending
- 1962-12-17 US US244943A patent/US3274312A/en not_active Expired - Lifetime
- 1962-12-20 DK DK556562AA patent/DK114993B/da unknown
- 1962-12-20 ES ES283581A patent/ES283581A1/es not_active Expired
-
1963
- 1963-12-19 FR FR919139A patent/FR1341351A/fr not_active Expired
Patent Citations (6)
| 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 (fr) * | 1958-11-12 | 1960-11-04 | Montedison Spa | Perfectionnements au filage des polymères viscoélastiques |
| 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)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1341351A (fr) | 1963-10-25 |
| GB1006582A (en) | 1965-10-06 |
| NL286762A (en)) | 1900-01-01 |
| BE626339A (en)) | 1900-01-01 |
| AT241677B (de) | 1965-08-10 |
| ES283581A1 (es) | 1963-07-01 |
| DK114993B (da) | 1969-08-25 |
| DE1218655B (de) | 1966-06-08 |
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