CA1104155A - Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine - Google Patents

Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine

Info

Publication number: CA1104155A
Authority: CA; Canada
Prior art keywords: acid; metal salt; alkaline earth; antistatic; alkali
Prior art date: 1976-11-08
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

Application number

CA363,271A

Other languages

English (en)

Inventor

Robert B. Login

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Corp

Original Assignee

BASF Wyandotte Corp

Priority date (The priority date 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 date listed.)

1976-11-08

Filing date

1980-10-24

Publication date

1981-06-30

1976-11-08 Priority claimed from US05/739,497 external-priority patent/US4080315A/en

1980-10-24 Application filed by BASF Wyandotte Corp filed Critical BASF Wyandotte Corp

1980-10-24 Priority to CA363,271A priority Critical patent/CA1104155A/fr

1981-06-30 Application granted granted Critical

1981-06-30 Publication of CA1104155A publication Critical patent/CA1104155A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 24
125000002768 hydroxyalkyl group Chemical group 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 14
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims description 21
-1 alkali metal alkoxides Chemical class 0.000 claims description 17
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 6
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
229960003080 taurine Drugs 0.000 claims description 5
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
229920000728 polyester Polymers 0.000 abstract description 21
150000001875 compounds Chemical class 0.000 abstract description 11
239000000654 additive Substances 0.000 abstract description 4
239000002216 antistatic agent Substances 0.000 description 19
239000000835 fiber Substances 0.000 description 13
229920000642 polymer Polymers 0.000 description 10
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000004952 Polyamide Substances 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
229920002647 polyamide Polymers 0.000 description 6
239000000376 reactant Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229940043237 diethanolamine Drugs 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
230000001143 conditioned effect Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
229920001155 polypropylene Polymers 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
238000002074 melt spinning Methods 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
238000005108 dry cleaning Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229920005594 polymer fiber Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 2
150000008054 sulfonate salts Chemical class 0.000 description 2
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
229920002994 synthetic fiber Polymers 0.000 description 2
239000012209 synthetic fiber Substances 0.000 description 2
229920001059 synthetic polymer Polymers 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
UUKKHCPKAGOIPC-UHFFFAOYSA-N 1-hydroxy-2-methylpropane-2-sulfonic acid Chemical compound OCC(C)(C)S(O)(=O)=O UUKKHCPKAGOIPC-UHFFFAOYSA-N 0.000 description 1
FYGCFQANVJVFIT-UHFFFAOYSA-N 2-hydroxy-2-methylpropane-1-sulfonic acid Chemical compound CC(C)(O)CS(O)(=O)=O FYGCFQANVJVFIT-UHFFFAOYSA-N 0.000 description 1
SMFVCSFXTHBQGP-UHFFFAOYSA-N 2-hydroxy-3-methoxypropane-1-sulfonic acid Chemical compound COCC(O)CS(O)(=O)=O SMFVCSFXTHBQGP-UHFFFAOYSA-N 0.000 description 1
NSRGOAGKXKNHQX-UHFFFAOYSA-N 2-hydroxybutane-1-sulfonic acid Chemical compound CCC(O)CS(O)(=O)=O NSRGOAGKXKNHQX-UHFFFAOYSA-N 0.000 description 1
QBRYGDSLFHXJOD-UHFFFAOYSA-N 2-hydroxycyclohexane-1-sulfonic acid Chemical compound OC1CCCCC1S(O)(=O)=O QBRYGDSLFHXJOD-UHFFFAOYSA-N 0.000 description 1
HSXUNHYXJWDLDK-UHFFFAOYSA-N 2-hydroxypropane-1-sulfonic acid Chemical compound CC(O)CS(O)(=O)=O HSXUNHYXJWDLDK-UHFFFAOYSA-N 0.000 description 1
FOEVHHOHFUGYJL-UHFFFAOYSA-N 3-hydroxybutane-2-sulfonic acid Chemical compound CC(O)C(C)S(O)(=O)=O FOEVHHOHFUGYJL-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001279 adipic acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
HDLHSQWNJQGDLM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,5-dicarboxylic acid Chemical compound C1C2C(C(=O)O)CC1C(C(O)=O)C2 HDLHSQWNJQGDLM-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
238000005266 casting Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
150000003841 chloride salts Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
229940043276 diisopropanolamine Drugs 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
150000002311 glutaric acids Chemical class 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229940045996 isethionic acid Drugs 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000011160 magnesium carbonates Nutrition 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical class OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
150000002913 oxalic acids Chemical class 0.000 description 1
125000005702 oxyalkylene group Chemical group 0.000 description 1
150000003047 pimelic acids Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003330 sebacic acids Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003442 suberic acids Chemical class 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1

Landscapes

Polyamides (AREA)
Compositions Of Macromolecular Compounds (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

CA363,271A 1976-11-08 1980-10-24 Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine Expired CA1104155A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA363,271A CA1104155A (fr)	1976-11-08	1980-10-24	Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US739,497		1976-11-08
US05/739,497 US4080315A (en)	1976-11-08	1976-11-08	Polyesters of N,N-bis(hydroxyalkyl) taurine salts as antistatic agents for synthetic polymers
CA289,412A CA1111189A (fr)	1976-11-08	1977-10-25	Polyesters de sels de n, n-bis (hydroxyalkyl) taurine servant d'agents antistatiques pour polymeres synthetiques
CA363,271A CA1104155A (fr)	1976-11-08	1980-10-24	Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine

Publications (1)

Publication Number	Publication Date
CA1104155A true CA1104155A (fr)	1981-06-30

Family

ID=27165343

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA363,271A Expired CA1104155A (fr)	1976-11-08	1980-10-24	Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine

Country Status (1)

Country	Link
CA (1)	CA1104155A (fr)

1980
- 1980-10-24 CA CA363,271A patent/CA1104155A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-06-30	MKEX	Expiry

Publication	Publication Date	Title
CA1111189A (fr)	1981-10-20	Polyesters de sels de n, n-bis (hydroxyalkyl) taurine servant d'agents antistatiques pour polymeres synthetiques
US4745142A (en)	1988-05-17	Stainproof polyester fiber
US4585835A (en)	1986-04-29	Polymer compositions
US3632666A (en)	1972-01-04	Polyether-polyamide block copolymers containing polyamide polyester or polyamide-polyester or polyamidepolyester block copolymeric synthetic resins and ionic compounds
US4006123A (en)	1977-02-01	Conductive aliphatic polyester or polyetherester having units containing phosphonium sulfonate groups
US4165303A (en)	1979-08-21	Polymer compositions containing poly (alkylene ether) esters of polybasic acids
US3787523A (en)	1974-01-22	Antistatic polyamide fiber containing sulfonic acid polyether reaction product
US4101528A (en)	1978-07-18	Copolyesters of ethylene 2,6-naphthalene dicarboxylate and halogenated comonomers
US4092302A (en)	1978-05-30	Phosphorus-containing copolyamides and fibers thereof
CA1104155A (fr)	1981-06-30	Procede pour la production de sels de n, n,-bis (hydroxyalkyl) taurine
US4214069A (en)	1980-07-22	Flame-resistant copolyesters containing phosphonic groups
EP0547701A2 (fr)	1993-06-23	Copolyesters linéaires contenant du phosphore, procédé de leur préparation et leur utilisation comme additifs retardant la flamme
EP0366102A2 (fr)	1990-05-02	Polyéther-ester copolymère séquencé et filaments à partir de celui-ci
US3874157A (en)	1975-04-01	Flame-retardant fiber blend
US4163088A (en)	1979-07-31	Antistatic polyamide compositions with polyalkyleneglycol ether having secondary terminal urethane groups
JPS62197419A (ja)	1987-09-01	含フツ素ポリエステル
US4239801A (en)	1980-12-16	Synthetic fibers having improved antistatic properties
US4035346A (en)	1977-07-12	Conductive N-alkyl polyamide having units containing phosphonium sulfonate groups
KR19990006227A (ko)	1999-01-25	난연성 폴리에스테르 섬유의 제조방법
USRE28212E (en)	1974-10-29	Table iii
JP4112963B2 (ja)	2008-07-02	ポリウレタン及びそれからなる弾性繊維
US3641198A (en)	1972-02-08	Polyamides containing antistatic polyolefins having pendant polyoxyalkylene chains
US3758442A (en)	1973-09-11	Ocess for preparation thereof and articles thereof novel polyetheresters of hydroxyalkoxyl diphenyl-4-carboxylic acid pr
US3285993A (en)	1966-11-15	Tertiary amino polyamides as dyeability improvers for polyester resins
JPWO2019167541A1 (ja)	2021-02-12	ポリエーテルエステルアミド組成物