US3262989A - Polyamide containing oxidized polyethylene - Google Patents
Polyamide containing oxidized polyethylene Download PDFInfo
- Publication number
- US3262989A US3262989A US229967A US22996762A US3262989A US 3262989 A US3262989 A US 3262989A US 229967 A US229967 A US 229967A US 22996762 A US22996762 A US 22996762A US 3262989 A US3262989 A US 3262989A
- Authority
- US
- United States
- Prior art keywords
- polyamide
- polymer
- partially oxidized
- oxidized polyethylene
- reactants
- 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
- 239000004952 Polyamide Substances 0.000 title claims description 33
- 229920002647 polyamide Polymers 0.000 title claims description 33
- 239000004698 Polyethylene Substances 0.000 title claims description 20
- -1 polyethylene Polymers 0.000 title claims description 20
- 229920000573 polyethylene Polymers 0.000 title claims description 20
- 229920000642 polymer Polymers 0.000 claims description 28
- 238000005299 abrasion Methods 0.000 claims description 12
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000007127 saponification reaction Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920013716 polyethylene resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241001043922 Pensacola Species 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004985 diamines Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 201000002266 mite infestation Diseases 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- 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
-
- 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
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
Definitions
- a further object of this invention is to provide a novel polyamide polymer for the preparation of ropes, cords or like items, the filaments of which do not require a coating.
- the objects of this invention are accomplished by adding to polyamide forming reactants, at any time prior to the completion of their polyamide forming reaction or prior to the preparation of films and fibers from the polyamide material, from 0.1 percent to 5 percent by weight of the reactants of a partially oxidized low molecular weight polyethylene polymer capable of forming an emulsion in aqueous solutions.
- the polyamide forming reactants may be of any of the Well known materials suitable for making a polyamide polymer capable of being spun or drawn into fibers or filaments and may comprise a mixture of organic primary or secondary diamine and dibasic carboxylic acid, salt thereof, or a polymarizable monoamino organic acid.
- the partially oxidized low molecular weight polyethylene polymer may be any type capable of forming an emulsion in aqueous solution and having properties which are within the limits shown in Table 1 which follows.
- the partially oxidized low molecular weight polyethylene polymer capable of forming aqueous emulsions may be added to the polyamide forming reactants prior to or during their mixing, at any time during the polycondensation thereof, or after the poly condensation thereof but prior to the preparation of films or fibers therefrom.
- Any means for dispersing the partially oxidized low molecular weight polyethylene polymer with reasonable uniformity in the polyamide is suitable and may include the simple and well known method of mixing two materials, normally solids at rooms temperature, by melting and stirring.
- EXAMPLE I A 50 percent water solution of substantially equal quantities of hexamethylenediamine and adipic acid was prepared and mixed and then this water solution of the reactants was subjected first to evaporating conditions at 137 C. and 13 psig. for approximately 30 minutes and then to reacting conditions of 220 C. to 280 C. and 250 p.s.i.g. for approximately 90 minutes. Following this, the partially polymerized reactant solution was subjected to flashing conditions of atmosphere pressure while the temperature of the reactants was maintained at 280 C. The final step in the polymerization was accomplished by holding the partially polymerized reactants at 280 C.
- the yarn thus prepared was plied and twisted to strands and laid to form a one-half inch diameter rope.
- one-half inch diameter rope was prepared in an identical manner from the polyamide chips prepared previously and with which partially oxidized polyethylene polymer was not blended.
- a 50 percent water solution of substantially equal quantities of hexamethylenediamine and adipic acid was prepared as in Example I and then this water solution of the reactants was subjected to evaporating conditions of 137 C. and 13 pounds per square inch for approximately 30 minutes. The evaporated water solution of the reactants was then subjected to reacting conditions of 220280 C. and 250 pounds per square inch. As soon as reacting conditions were reached in the evaporated water solution, 2 percent by weight of the partially oxidized granular polyethylene polymer, sold under the trademark Epolene (registered trademark of Eastman Kodak Company for its polyethylene resins) and having the grade designation E-l0, was added to the evaporated water solution of the reactants.
- Epolene registered trademark of Eastman Kodak Company for its polyethylene resins
- a process for preparing polyamide polymer having increased abrasion resistance comprising, in combination, the steps of:
- a polyamide polymer for forming fibers which have improved abrasion resistance and tension wet strength which comprises polyhexamethylene adipamide and from 0.1% to 5.0%, by weight of said polyhexamethylene adipamide, of partially oxidized polyethylene polymer having a number average molecular weight of 1,000 to 3,000, an acid number of 9 to 16, and a saponification number of 24 to 30.
- a polyamide polymer yarn which has improved abrasion resistance and tension wet strength which comprises polyhexamethylene adipamide and from 0.1% to 5.0%, by weight of said polyhexamethylene adipamide, of partially oxidized polyethylene polymer having a number average molecular weight of 1,000 to 3,000, an
- a polyamide polymer rope which has improved U ITE STA ES ATENTS abrasion resistance and tension wet strength which com- 2,890,125 6/1959 Mange 7 260-23 prises polymerized polyhexamethylene adipamide and 5 3,093,255 6/1963 Mesroblan et a1 260-857 from 0.1% to 5.0% by weight of said polyhexamethylene adipamide of partially oxidized polyethylene polymer MURRAY TILLMAN Exammer' having a number average molecular weight of 1,000 to WILLIAM H. SHORT, Examiner.
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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL299163D NL299163A (en)) | 1962-10-11 | ||
| BE638561D BE638561A (en)) | 1962-10-11 | ||
| NL127717D NL127717C (en)) | 1962-10-11 | ||
| US229967A US3262989A (en) | 1962-10-11 | 1962-10-11 | Polyamide containing oxidized polyethylene |
| CH1244663A CH427275A (fr) | 1962-10-11 | 1963-10-10 | Procédé de préparation d'un polyamide à forte résistance à l'usure par frottement |
| LU44597D LU44597A1 (en)) | 1962-10-11 | 1963-10-10 | |
| SE11137/63A SE303879B (en)) | 1962-10-11 | 1963-10-10 | |
| FR950207A FR1371081A (fr) | 1962-10-11 | 1963-10-10 | Perfectionnements aux polyamides, notamment en vue d'accroître leur résistance à l'usure par frottement |
| GB39977/63A GB1014066A (en) | 1962-10-11 | 1963-10-10 | Polyamide |
| DEM58487A DE1266966B (de) | 1962-10-11 | 1963-10-10 | Verfahren zur Erhoehung der Abriebfestigkeit und Nasszugfestigkeit von faserbildenden Polyamiden |
| DK476563AA DK105614C (da) | 1962-10-11 | 1963-10-10 | Fremgangsmåde ved fremstilling af polyamid, især polyamifibre. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US229967A US3262989A (en) | 1962-10-11 | 1962-10-11 | Polyamide containing oxidized polyethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3262989A true US3262989A (en) | 1966-07-26 |
Family
ID=22863422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US229967A Expired - Lifetime US3262989A (en) | 1962-10-11 | 1962-10-11 | Polyamide containing oxidized polyethylene |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3262989A (en)) |
| BE (1) | BE638561A (en)) |
| CH (1) | CH427275A (en)) |
| DE (1) | DE1266966B (en)) |
| DK (1) | DK105614C (en)) |
| GB (1) | GB1014066A (en)) |
| LU (1) | LU44597A1 (en)) |
| NL (2) | NL299163A (en)) |
| SE (1) | SE303879B (en)) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3471426A (en) * | 1964-10-24 | 1969-10-07 | British Nylon Spinners Ltd | Polyamide containing dispersed polyolefin and fatty dispersing agent |
| US3484403A (en) * | 1966-03-14 | 1969-12-16 | Eastman Kodak Co | Preparation of polyamide-carboxylated polyolefin melt blends |
| US3544520A (en) * | 1968-04-22 | 1970-12-01 | Standard Oil Co | Lubricant additives from formaldehyde-polyalkylene polyamine oxidized olefin polymer condensation products |
| FR2352868A1 (fr) * | 1976-05-24 | 1977-12-23 | Raychem Sa Nv | Adhesifs |
| EP0003477A3 (en) * | 1978-02-13 | 1979-09-05 | Bayer Aktiengesellschaft | Conditioning-free polyamide mouldings |
| US4755552A (en) * | 1986-04-22 | 1988-07-05 | Huels Aktiengesellschaft | Impact-resistant polyamide molding compounds |
| US20080125530A1 (en) * | 2006-11-25 | 2008-05-29 | Evonik Degussa Gmbh | Use of a synthetic wax oxidate as processing aid for transparent polar polymers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2890125A (en) * | 1956-10-01 | 1959-06-09 | Petrolite Corp | Modification of oxidized hydrocarbons and products therefrom |
| US3093255A (en) * | 1958-08-28 | 1963-06-11 | Continental Can Co | Method of preparing mixtures of hydrocarbon polymer resins and linear polyamide resins and product thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468534A (en) * | 1944-11-23 | 1949-04-26 | Standard Oil Dev Co | Tough, flexible, polyamide resinhydrocarbon resin compositions |
-
0
- BE BE638561D patent/BE638561A/xx unknown
- NL NL127717D patent/NL127717C/xx active
- NL NL299163D patent/NL299163A/xx unknown
-
1962
- 1962-10-11 US US229967A patent/US3262989A/en not_active Expired - Lifetime
-
1963
- 1963-10-10 CH CH1244663A patent/CH427275A/fr unknown
- 1963-10-10 DE DEM58487A patent/DE1266966B/de active Pending
- 1963-10-10 LU LU44597D patent/LU44597A1/xx unknown
- 1963-10-10 DK DK476563AA patent/DK105614C/da active
- 1963-10-10 GB GB39977/63A patent/GB1014066A/en not_active Expired
- 1963-10-10 SE SE11137/63A patent/SE303879B/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2890125A (en) * | 1956-10-01 | 1959-06-09 | Petrolite Corp | Modification of oxidized hydrocarbons and products therefrom |
| US3093255A (en) * | 1958-08-28 | 1963-06-11 | Continental Can Co | Method of preparing mixtures of hydrocarbon polymer resins and linear polyamide resins and product thereof |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3471426A (en) * | 1964-10-24 | 1969-10-07 | British Nylon Spinners Ltd | Polyamide containing dispersed polyolefin and fatty dispersing agent |
| US3484403A (en) * | 1966-03-14 | 1969-12-16 | Eastman Kodak Co | Preparation of polyamide-carboxylated polyolefin melt blends |
| US3544520A (en) * | 1968-04-22 | 1970-12-01 | Standard Oil Co | Lubricant additives from formaldehyde-polyalkylene polyamine oxidized olefin polymer condensation products |
| FR2352868A1 (fr) * | 1976-05-24 | 1977-12-23 | Raychem Sa Nv | Adhesifs |
| EP0003477A3 (en) * | 1978-02-13 | 1979-09-05 | Bayer Aktiengesellschaft | Conditioning-free polyamide mouldings |
| US4293662A (en) * | 1978-02-13 | 1981-10-06 | Bayer Aktiengesellschaft | Polyamides containing oxidized polyethylene |
| US4755552A (en) * | 1986-04-22 | 1988-07-05 | Huels Aktiengesellschaft | Impact-resistant polyamide molding compounds |
| US20080125530A1 (en) * | 2006-11-25 | 2008-05-29 | Evonik Degussa Gmbh | Use of a synthetic wax oxidate as processing aid for transparent polar polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1014066A (en) | 1965-12-22 |
| DK105614C (da) | 1966-10-17 |
| SE303879B (en)) | 1968-09-09 |
| BE638561A (en)) | |
| NL299163A (en)) | |
| DE1266966B (de) | 1968-04-25 |
| CH427275A (fr) | 1966-12-31 |
| LU44597A1 (en)) | 1964-04-10 |
| NL127717C (en)) |
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