US3334153A - Mixture of polyamide, polystyrene, and polyamide-styrene graft copolymer - Google Patents
Mixture of polyamide, polystyrene, and polyamide-styrene graft copolymer Download PDFInfo
- Publication number
- US3334153A US3334153A US455652A US45565265A US3334153A US 3334153 A US3334153 A US 3334153A US 455652 A US455652 A US 455652A US 45565265 A US45565265 A US 45565265A US 3334153 A US3334153 A US 3334153A
- Authority
- US
- United States
- Prior art keywords
- polyamide
- polystyrene
- mixture
- styrene
- graft
- 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
- 239000004793 Polystyrene Substances 0.000 title claims description 31
- 229920002223 polystyrene Polymers 0.000 title claims description 31
- 239000000203 mixture Substances 0.000 title claims description 25
- 239000004952 Polyamide Substances 0.000 title claims description 23
- 229920002647 polyamide Polymers 0.000 title claims description 23
- 229920000578 graft copolymer Polymers 0.000 title claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 31
- 239000000835 fiber Substances 0.000 claims description 13
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 description 18
- 238000009987 spinning Methods 0.000 description 18
- 239000004677 Nylon Substances 0.000 description 14
- 229920001778 nylon Polymers 0.000 description 14
- 238000000034 method Methods 0.000 description 10
- 238000002074 melt spinning Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920002292 Nylon 6 Polymers 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000005204 segregation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 241000581364 Clinitrachus argentatus Species 0.000 description 1
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000004753 textile Substances 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
- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/56—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polymers of cyclic compounds with one carbon-to-carbon double bond in the side chain
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- 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
- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
- D01F6/90—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Definitions
- This invention relates to blended spun fibers consisting of polyamide or a cocondensate consisting mainly of polyamide (A-condensate), and polystyrene or copolymer consisting mainly of polystyrene (B-polymer) by melt spinning, more particularly, to a blended spun fiber consisting of a mixture of at least 20% of the A-condensate and B-polymer manufactured by extruding a melt of a mixture of A-condensate, B-polymer and copolycondensate of polyamide and polystyrene through a spinneret to obtain the blended spun fiber.
- the inventors have found a spinning condition for enabling stable, high speed spinning based on the prevention of segregation by means of the quenched spinning system as explained above, and further found in estab lishing more stable spinning condition as well as seeking fora method other than the quenching system for solving such troublesome phenomena of rapid segregation of polyamide and polystyrene during the cooling step; and they arrived at the present invention which enables very stable and very high speed spinning by admixing part of a copolymeric condensate of polyamide and polystyrene to a spinning solution consisting of the A-condensate and the B-polymer, then substantially no segregation phenomena of polyamide and polystyrene occur even during the cooling step, but they exhibit a uniformly distributed state, and in case of extrusion of such solution through the spinneret.
- graft copolymeric condensate of polyamide and polystyrene to be used in the invention, chemical methods, photochemical method, oxidation method utilizing peroxide, ultraviolet irradiation methods, radiant ray irradiation methods, a method utilizing an initiator of ionic polymerization systems, such as BF AlCl TiCl and A1Br and other various methods capable of forming graft copolymeric condensates are available.
- a graft copolymeric condensate consisting of 6-nylon and polystyrene where styrene is graft-polymerized with 6- nylon by means of radiant rays, or a graft-polymeric condensate where lactam is condensed with a copolymer of styrene and acrylic acid, and others can be used in the invention.
- the optimum temperature for melt spinning depends upon the kind of the A-condensate and cannot be specified at random. However, such a temperature range of higher by 30 C. than the melting point of the A-condensate to higher by C. than the said melting point is adopted.
- a spinning method characterized by cooling down to a temperature in a definite range the filament just after the melt spinning according to the invention can be applied in parallel. There may be a case where the said application Willl be more advantageous, depending upon the mixture ratio of A-condensate and Bpolymer.
- Example 1 Nylon 6 (polycaprolactam) was irradiated with cobalt 60 to a total dose of 3x 10% and then was immersed in styrene monomer to effect graft copolymerization with the styrene. The graft polymerization was continued until a graft copolymer of 50% styrene content had been obtained. Five parts of the said copolymer were blended with parts of a mixture of 40% of 6-nylon and 60% of polystyrene and supplied to a screw extruder heated up to 280 C., whereby the mixture was extruded through a spinneret of 350 holes each having 0.25 mm. dia. Very stable spinning was carried out by taking up at a speed of 500 m./minute. On the other hand, when said copolymer was not blended, the filament was often cut off even at a spinning speed of 200 m./minute.
- Example 3 A mixture of 55% of styrene, 40% of e-caprolactam, 4.5% of acrylic acid, and 0.5% of benzoyl peroxide was heated at 100 C. for 6 hours and then at 300 C. for 6 hours, whereby the graft polymer of styrene and nylon was obtained.
- Four parts of said copolymer were blended with 96 parts of a mixture of 45% of 6-nylon and 55% of polystyrene and supplied to a screw extruder heated up to 290 0., whereby the mixture was extruded through a spinneret having 100 holes each having 0.3 mm. dia.
- Very stable spinning was effected by winding at a speed of 700 m./minute while blowing air into the filament drawing part under the spinneret and lowering to 70 C. the temperature of the atmosphere at the part of 5 mm. outside of the filament by 30 mm. lower than the spinneret surface.
- a polyamide-polystyrene fiber consisting substantially of 99 to '95 parts by weight of a mixture of 20 to 50 percent by weight of polyamide and 80 to 50 percent by weight of polystyrene, and 1 to 5 parts by weight of a graft copolymer selected from the group consisting of a polyamide-graft-copolymerized with styrene, a polystyrene graft-copolymerized with epsi'lon-caprolactam, and a styrene-epsilon-caprolactam graft copolymer.
- a fiber according to claim 1 wherein said copolymer is a graft copolymer consisting of styrene-acrylic 5.
- a fiber according to claim 1, wherein said mixture consists of 95 parts of a mixture of 40% by weight of polycaprolactam and 60% by weight of polystyrene and 5 parts of copolymer containing by weight of styrene obtained by grafting styrene with the irradiated polycaprolactam.
- a composition suitable for the melt-spinning of polyamide-polystyrene fibers substantially consisting of 99 to parts by weight of a mixture of 20 to 50 percent by weight of polyamide and 80 to 50 percent by weight of polystyrene, and 1 to 5 parts by weight of a graft copolymer selected from the group consisting of a polyamide graft-copolymerized with styrene, a polystyrene graftcopolymerized with epsilon-caprolactam and a styreneepsilon-caprolactam graft copolymer.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3291264 | 1964-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3334153A true US3334153A (en) | 1967-08-01 |
Family
ID=12372091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US455652A Expired - Lifetime US3334153A (en) | 1964-06-11 | 1965-05-13 | Mixture of polyamide, polystyrene, and polyamide-styrene graft copolymer |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3334153A (enrdf_load_stackoverflow) |
| FR (1) | FR1440248A (enrdf_load_stackoverflow) |
| GB (1) | GB1052323A (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4378448A (en) * | 1979-10-20 | 1983-03-29 | Raychem Corporation | Polyamide graft as hot-melt adhesive, and elastomer blend |
| US4965318A (en) * | 1986-02-12 | 1990-10-23 | Basf Aktiengesellschaft | Thermoplastic molding materials based on nylons and styrene copolymers |
| US5728741A (en) * | 1994-02-09 | 1998-03-17 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US5855981A (en) * | 1994-02-09 | 1999-01-05 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US5914353A (en) * | 1995-08-21 | 1999-06-22 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US6162748A (en) * | 1995-02-15 | 2000-12-19 | Collins & Aikman Floorcoverings, Inc. | Woven floor coverings |
| US20030114062A1 (en) * | 2000-06-19 | 2003-06-19 | Graham Scott | Floor covering with woven face |
| US6860953B1 (en) | 1994-02-09 | 2005-03-01 | Collins & Aikman Floorcoverings, Inc. | Process for manufacturing a floor covering having a foamed backing formed from recycled polymeric material |
| CN109385709A (zh) * | 2017-08-09 | 2019-02-26 | 中国石化仪征化纤有限责任公司 | 一种高速纺仪纶纱线的生产方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA792393B (en) | 1978-05-25 | 1980-05-28 | British Industrial Plastics | Thermoplastics polymer compositions |
| CN110067039B (zh) * | 2019-04-22 | 2022-02-08 | 上海梦丝新材料科技有限公司 | 一种新型的苯乙烯嵌段共聚物混合物弹性纤维及其制造方法 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB872515A (en) * | 1958-12-30 | 1961-07-12 | Du Pont | Improvements relating to the production of graft copolymers |
| DE1131883B (de) * | 1960-10-07 | 1962-06-20 | Basf Ag | Verfahren zur Herstellung von Block-Pfropf-Polymeren aus Polyolefinen und Polykondensaten |
| GB899567A (en) * | 1960-01-07 | 1962-06-27 | Basf Ag | Graft copolymers from olefinically unsaturated monomers and polycondensates and a process for their production |
| US3088791A (en) * | 1959-02-06 | 1963-05-07 | Du Pont | Graft polymerization of a vinyl monomer to a polymeric substrate by low temperature irradiation |
| US3134746A (en) * | 1961-06-09 | 1964-05-26 | Borg Warner | Blends of epsilon caprolactam polymer and graft copolymer alkenyl cyanide and alkenyl substituted aromatic hydrocarbon on polybutadiene |
| US3218371A (en) * | 1961-07-31 | 1965-11-16 | Borg Warner | Blends of (1) epsilon caprolactam, (2) rubbery butadiene-acrylonitrile copolymers, and (3) resinous styrene-acrylonitrile copolymers |
| US3236914A (en) * | 1959-05-12 | 1966-02-22 | Canadian Ind | Method for rendering polymers compatible |
| US3243478A (en) * | 1962-12-27 | 1966-03-29 | Us Rubber Co | Mixture comprising polyamide and styrene acrylonitrile copolymer |
-
1965
- 1965-04-26 GB GB1742865A patent/GB1052323A/en not_active Expired
- 1965-05-13 US US455652A patent/US3334153A/en not_active Expired - Lifetime
- 1965-05-26 FR FR18461A patent/FR1440248A/fr not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB872515A (en) * | 1958-12-30 | 1961-07-12 | Du Pont | Improvements relating to the production of graft copolymers |
| US3088791A (en) * | 1959-02-06 | 1963-05-07 | Du Pont | Graft polymerization of a vinyl monomer to a polymeric substrate by low temperature irradiation |
| US3236914A (en) * | 1959-05-12 | 1966-02-22 | Canadian Ind | Method for rendering polymers compatible |
| GB899567A (en) * | 1960-01-07 | 1962-06-27 | Basf Ag | Graft copolymers from olefinically unsaturated monomers and polycondensates and a process for their production |
| DE1131883B (de) * | 1960-10-07 | 1962-06-20 | Basf Ag | Verfahren zur Herstellung von Block-Pfropf-Polymeren aus Polyolefinen und Polykondensaten |
| US3134746A (en) * | 1961-06-09 | 1964-05-26 | Borg Warner | Blends of epsilon caprolactam polymer and graft copolymer alkenyl cyanide and alkenyl substituted aromatic hydrocarbon on polybutadiene |
| US3218371A (en) * | 1961-07-31 | 1965-11-16 | Borg Warner | Blends of (1) epsilon caprolactam, (2) rubbery butadiene-acrylonitrile copolymers, and (3) resinous styrene-acrylonitrile copolymers |
| US3243478A (en) * | 1962-12-27 | 1966-03-29 | Us Rubber Co | Mixture comprising polyamide and styrene acrylonitrile copolymer |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4378448A (en) * | 1979-10-20 | 1983-03-29 | Raychem Corporation | Polyamide graft as hot-melt adhesive, and elastomer blend |
| US4965318A (en) * | 1986-02-12 | 1990-10-23 | Basf Aktiengesellschaft | Thermoplastic molding materials based on nylons and styrene copolymers |
| US5728741A (en) * | 1994-02-09 | 1998-03-17 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US5855981A (en) * | 1994-02-09 | 1999-01-05 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US6228479B1 (en) | 1994-02-09 | 2001-05-08 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US6860953B1 (en) | 1994-02-09 | 2005-03-01 | Collins & Aikman Floorcoverings, Inc. | Process for manufacturing a floor covering having a foamed backing formed from recycled polymeric material |
| US6162748A (en) * | 1995-02-15 | 2000-12-19 | Collins & Aikman Floorcoverings, Inc. | Woven floor coverings |
| US5914353A (en) * | 1995-08-21 | 1999-06-22 | Collins & Aikman Floorcoverings, Inc. | Process of recycling waste polymeric material and an article utilizing the same |
| US20030114062A1 (en) * | 2000-06-19 | 2003-06-19 | Graham Scott | Floor covering with woven face |
| CN109385709A (zh) * | 2017-08-09 | 2019-02-26 | 中国石化仪征化纤有限责任公司 | 一种高速纺仪纶纱线的生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1052323A (enrdf_load_stackoverflow) | 1966-12-21 |
| FR1440248A (fr) | 1966-05-27 |
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