US3437641A - Process for improving the acid dye receptivity of polylactams and polylactam products so produced - Google Patents
Process for improving the acid dye receptivity of polylactams and polylactam products so produced Download PDFInfo
- Publication number
- US3437641A US3437641A US530374A US3437641DA US3437641A US 3437641 A US3437641 A US 3437641A US 530374 A US530374 A US 530374A US 3437641D A US3437641D A US 3437641DA US 3437641 A US3437641 A US 3437641A
- Authority
- US
- United States
- Prior art keywords
- acid
- polylactam
- polyamide
- viscosity
- receptivity
- 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
- 238000000034 method Methods 0.000 title description 26
- 230000008569 process Effects 0.000 title description 25
- 239000000980 acid dye Substances 0.000 title description 15
- 239000004952 Polyamide Substances 0.000 description 23
- 229920002647 polyamide Polymers 0.000 description 23
- 239000000654 additive Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- -1 aryl phosphonic acid Chemical compound 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 238000009987 spinning Methods 0.000 description 13
- 229920002292 Nylon 6 Polymers 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
- 150000002903 organophosphorus compounds Chemical class 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 238000005520 cutting process Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 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 6
- 230000008033 biological extinction Effects 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 3
- DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 description 2
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000269775 Centropomidae Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N Putrescine Natural products NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- BUJNIHFICKTDHT-UHFFFAOYSA-M sodium;4-[4-[acetyl(methyl)amino]anilino]-1-amino-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].C1=CC(N(C(C)=O)C)=CC=C1NC1=CC(S([O-])(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O BUJNIHFICKTDHT-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
Definitions
- the product exhibits improved receptivity for acid dyes with a minimum reduction of its solution viscosity.
- This invention relates to a process for improving the dye receptivity of polylactams for acid dyes, and more particularly, the invention is directed to a process of incorporating a combination of certain organic phosphorous compounds and amines into a fiber-forming polylactam, especially polycaprolactam, so as to obtain a product which is easily spun into textile fibers and which can be dyed in an improved manner with acid dyes.
- the dye receptivity of fiber-forming polyamides for acid dyes can be improved if the polyamide is initially treated so as to contain an increased number of amino end groups.
- One method of achieving this result has been to add free amines to the polyamide-forming initial materials prior to polycondensation. Suitable amines which have been suggested for this purpose include aliphatic monoamines or diamines and heterocyclic amines. Where the polyamide is obtained by polycondensation of dicarboxylic acids and diamines, e.g., in the preparation of polyhexamethylene adipamide, only a small excess of the above-noted free amines is necessary.
- this defect in the polyamide caused by the addition of the amine is supposed to be avoided by adding phosphorous compounds to the polyamide prior to spinning.
- Suitable phosphorous compounds suggested for this purpose are hypophosphites of alkali and alkaline earth metals as well as those of zinc, cadmium, manganese, aluminum and tin, and also salts of phosphinic acid.
- the dye receptivity of polyamides is supposed to be improved by the addition of alkylor aryl-phosphinic acids or their amine salts.
- One object of the present invention is to provide a process whereby a substantially improved acid dye receptivity can be imparted to a fiber-forming polylactam without impairing the subsequent spinning of the polymer into filaments.
- Another object of the invention is to provide a process for improving the receptivity of a fiber-forming polylactam for acid dyes by using a novel combination of additives which can be easily incorporated into the polylactam either before or during polycondensation of the lactam monomer or subsequently to the polylactam before it is spun into textile fibers.
- polylactams which are improved by the proc ess of this invention are well known fiber-forming polymers containing recurring NHCO groups connected by an alkylene group in the polymer chain.
- Polycaprolactam sometimes referred to as nylon 6, is most often used for commercial textiles, and the production of the polyamide fromthe monomeric lactam, such as epsiloncaprolactam is quite well known and requires no further explanation.
- the two essential additives of the invention i.e., the organic phosphorous compound and the polyamine can be introduced and incorporated into the polycaprolactam at any point prior to spinning filaments or fibers therefrom, under conditions which ensure an homogeneous mixture of the polymer and the additives, e.g., by thorough mixing during polycondensation or by kneading and homogenizing the additives with the molten polymer in an extruder or similar mixing device.
- the additives may be introduced before the polycondensation of the lactam monomer or at any suitable time during the polycondensation reaction.
- the two essential components of the invention with the polylactam product, which is in the form of cuttings, granules or small pellets at a point prior to spinning, e.g., by panniering the cuttings or otherwise surface coating the polymer particles.
- the organic phosphorous compound and the polyamine are homogeneously mixed with the polylactam by any conventional method, e.g., by reextruding the treated material in a screw extruder or even in a mixing section just preceding the melt spinning operation.
- organic phosphorous compound employed as component (a) in the process of the invention it is particularly desirable to employ those compounds of the formula in which X stands for aryl or alkyl, preferably phenyl and lower alkyl such as methyl, ethyl, propyl or butyl, X stands for aryl such as phenyl, aralkyl such as benzyl or lower alkyl, i.e., alkyl of 1 to 4 carbon atoms, and Y stands for hydrogen, aryl such as phenyl, or lower alkyl of 1 to 4 carbon atoms.
- Specific organic phosphorous compounds suitable for the purposes of the invention can be listed as follows:
- the acid dye receptivity cannot be further increased simply by the addition of larger amounts of this component because the viscosity of the polylactam is then simultaneously reduced.
- the acid dye receptivity of the polylactam increases quite sharply in a very surprising manner.
- the amines just as the organic phosphorous compounds cause a lowering of the viscosity, it has been found that a definite synergistic effect takes place with the dye receptivity increasing much more rapidly than any accompanying decrease in viscosity.
- the suitable selection of the phosphorous compounds and amines as well as by choosing appropriate amounts of these compounds within the prescribed limits of the invention.
- the preferred polyethylene polyamines as noted above offer the greatest advantage because they yield a very substantial increase in dye absorption even when using quite small amounts, and these small amounts of the polyamine have only a slight influence on the viscosity.
- the invention is further illustrated by without being limited to the following examples.
- the percentages of the phosphorous and amine compounds are by weight with reference to the particular lactam or polylactam which is being treated.
- the solution viscosity is measured in each instance by measuring the flew rate of a 1% solution of the polylactam in formic acid. Extinction values are obtained by conventional measurement of the dye solutions.
- Ethanephosphonic diethyl ester 1.0 2 05 1 3 8O "i g g h i 3 anep osp euro 2101 re y " ⁇ Diethylene triamine 0.4 i 1 3 ⁇ Ethanephosphonic acid diethyl es 0.1 2 14 1 2 34 gtefiametlhylefie diamigeafilnfuy 0.3
- EXAMPLE II Dried polycaprolactam cuttings ready for spinning with a solution viscosity of 2.55 are mixed in a tumbler drier successively with 0.3% by weight of hexamethylene diamine and 1% by weight of tributyl phosphate. Thereafter, these cuttings are regranulated in an extruder. After the regranulation, the modified polycaprolactam exhibits a solution viscosity of 2.53. The cuttings are then spun and the resulting filaments dyed as described in EX- ample I. By measuring the extinction proportion of the dyestuff extracted from each of the filament samples, the dyeing improvement of the modified polyamide by comparison with the unmodified polyamide is ascertained. The extinction proportion in this case amounts to 1:2.63 (polyamide without additive:polyamide-i-phosphorous compound-i-amine) As described in Example II above, further tests are carried out with changes in the compounds or additive amounts as summarized in the following table:
- a further advantage of the process according to the invention is to be seen in the fact that during the spinning of 'the polyamide the added phosphorous compounds cause a considerable after-condensation, so that even if in Example I.
- a process for improving the receptivity of a fiberforming polycaprolactam for acid dyes which comprises: homogeneously incorporating into said polycaprolactam:
- component (a) is a phosphoric acid ester of the formula X0 OX wherein X represents a substituent selected from the group consisting of lower alkyl and phenyl.
- component (a) is a compound of the formula YO OY wherein X' represents a substituent selected from the 8 group consisting of lower alkyl, phenyl and benzyl and Y represents a suhstituent selected from the group consisting of hydrogen, lower alkyl and phenyl.
- component (b) is a compound of the formula wherein p represents an integer of 2 to 4.
- component (b) is hexamethylene diamine.
- component (a) is ethanephosphonic acid diethyl ester.
- component (a) is methanephosphonic acid dimethyl ester.
- component (a) is tributyl phosphate.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV27948A DE1232735B (de) | 1965-03-03 | 1965-03-03 | Verfahren zur Erhoehung der Farbaufnahmefaehigkeit von Polyamiden aus Lactamen fuer saure Farbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3437641A true US3437641A (en) | 1969-04-08 |
Family
ID=7583786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US530374A Expired - Lifetime US3437641A (en) | 1965-03-03 | 1966-02-28 | Process for improving the acid dye receptivity of polylactams and polylactam products so produced |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3437641A (en, 2012) |
| AT (1) | AT262223B (en, 2012) |
| BE (1) | BE677106A (en, 2012) |
| CH (1) | CH466563A (en, 2012) |
| DE (1) | DE1232735B (en, 2012) |
| ES (1) | ES323294A1 (en, 2012) |
| FR (1) | FR1470218A (en, 2012) |
| GB (1) | GB1125633A (en, 2012) |
| NL (1) | NL6602666A (en, 2012) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3687904A (en) * | 1970-12-04 | 1972-08-29 | Ici Ltd | Polyamides |
| US3846532A (en) * | 1969-01-29 | 1974-11-05 | Bayer Ag | Continuous spinning and stretching process of the production of polyamide-6 filaments |
| US4258142A (en) * | 1978-08-30 | 1981-03-24 | Argus Chemical Corp. | Clarified olefin polymer composition |
| US4390667A (en) * | 1981-07-06 | 1983-06-28 | Allied Corporation | Process for increasing the melt viscosity of polyamide with aryl phosphate compound |
| EP0382559A3 (en) * | 1989-02-10 | 1991-09-11 | Tonen Chemical Corporation | Polymer composition |
| US5216054A (en) * | 1989-02-10 | 1993-06-01 | Tonen Sekiyukagaku Kabushiki Kaisha | Polymer composition |
| US5487856A (en) * | 1993-08-16 | 1996-01-30 | Basf Corporation | Process for the manufacture of a post-heat set dyed fabric of polyamide fibers having improved dye washfastness and heat stability |
| WO2002102885A1 (en) * | 2001-06-14 | 2002-12-27 | Basf Corporation | Light-stabilized polymers comprising light-stabilizing moieties, articles therefrom and a method of making the same |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2241322A (en) * | 1938-09-30 | 1941-05-06 | Du Pont | Process for preparing polyamides from cyclic amides |
| US2510777A (en) * | 1946-12-30 | 1950-06-06 | Du Pont | Polyamide treated with a hypophosphorous acid compound |
| US2557808A (en) * | 1946-06-26 | 1951-06-19 | Du Pont | Method for increasing the melt viscosity of synthetic linear polyamides |
| US2904536A (en) * | 1955-06-29 | 1959-09-15 | Du Pont | Polyamide containing interlinear piperazine units |
| US3296216A (en) * | 1963-09-09 | 1967-01-03 | Monsanto Co | Nylon composition having enhanced dyeability |
| US3296215A (en) * | 1963-12-30 | 1967-01-03 | Monsanto Co | Synthetic linear polycarbonamides having an improved receptivity for acid dyes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL111538C (en, 2012) * | 1957-12-23 |
-
1965
- 1965-03-03 DE DEV27948A patent/DE1232735B/de active Pending
-
1966
- 1966-02-19 ES ES0323294A patent/ES323294A1/es not_active Expired
- 1966-02-22 CH CH255766A patent/CH466563A/de unknown
- 1966-02-28 US US530374A patent/US3437641A/en not_active Expired - Lifetime
- 1966-02-28 BE BE677106D patent/BE677106A/xx unknown
- 1966-02-28 FR FR51380A patent/FR1470218A/fr not_active Expired
- 1966-03-01 NL NL6602666A patent/NL6602666A/xx unknown
- 1966-03-03 GB GB9403/66A patent/GB1125633A/en not_active Expired
- 1966-03-03 AT AT201766A patent/AT262223B/de active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2241322A (en) * | 1938-09-30 | 1941-05-06 | Du Pont | Process for preparing polyamides from cyclic amides |
| US2557808A (en) * | 1946-06-26 | 1951-06-19 | Du Pont | Method for increasing the melt viscosity of synthetic linear polyamides |
| US2510777A (en) * | 1946-12-30 | 1950-06-06 | Du Pont | Polyamide treated with a hypophosphorous acid compound |
| US2904536A (en) * | 1955-06-29 | 1959-09-15 | Du Pont | Polyamide containing interlinear piperazine units |
| US3296216A (en) * | 1963-09-09 | 1967-01-03 | Monsanto Co | Nylon composition having enhanced dyeability |
| US3300448A (en) * | 1963-09-09 | 1967-01-24 | Monsanto Co | Polyamide of enhanced dyeability containing phenyl phosphonic acid and nu-amino ethylpiperazine |
| US3296215A (en) * | 1963-12-30 | 1967-01-03 | Monsanto Co | Synthetic linear polycarbonamides having an improved receptivity for acid dyes |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846532A (en) * | 1969-01-29 | 1974-11-05 | Bayer Ag | Continuous spinning and stretching process of the production of polyamide-6 filaments |
| US3687904A (en) * | 1970-12-04 | 1972-08-29 | Ici Ltd | Polyamides |
| US4258142A (en) * | 1978-08-30 | 1981-03-24 | Argus Chemical Corp. | Clarified olefin polymer composition |
| US4390667A (en) * | 1981-07-06 | 1983-06-28 | Allied Corporation | Process for increasing the melt viscosity of polyamide with aryl phosphate compound |
| EP0382559A3 (en) * | 1989-02-10 | 1991-09-11 | Tonen Chemical Corporation | Polymer composition |
| US5216054A (en) * | 1989-02-10 | 1993-06-01 | Tonen Sekiyukagaku Kabushiki Kaisha | Polymer composition |
| US5487856A (en) * | 1993-08-16 | 1996-01-30 | Basf Corporation | Process for the manufacture of a post-heat set dyed fabric of polyamide fibers having improved dye washfastness and heat stability |
| WO2002102885A1 (en) * | 2001-06-14 | 2002-12-27 | Basf Corporation | Light-stabilized polymers comprising light-stabilizing moieties, articles therefrom and a method of making the same |
| US20030027978A1 (en) * | 2001-06-14 | 2003-02-06 | Otto Ilg | Light-stabilized polymeric articles and methods of making the same |
| US6867266B2 (en) | 2001-06-14 | 2005-03-15 | Basf Corporation | Light-stabilized polymeric articles and methods of making the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1232735B (de) | 1967-01-19 |
| CH466563A (de) | 1968-12-15 |
| AT262223B (de) | 1968-06-10 |
| BE677106A (en, 2012) | 1966-07-18 |
| FR1470218A (fr) | 1967-02-17 |
| GB1125633A (en) | 1968-08-28 |
| NL6602666A (en, 2012) | 1966-09-05 |
| ES323294A1 (es) | 1967-02-01 |
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