CA1335682C - Fibres aramides couleur - Google Patents

Fibres aramides couleur

Info

Publication number: CA1335682C
Authority: CA; Canada
Prior art keywords: pigment; pigments; fiber; colour index; fibers
Prior art date: 1987-06-18
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 - Fee Related

Application number

CA000581218A

Other languages

English (en)

Inventor

Kiu-Seung Lee

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1987-06-18

Filing date

1988-10-25

Publication date

1995-05-23

1988-08-01 Priority to US07/226,645 priority Critical patent/US4994323A/en

1988-10-25 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1988-10-25 Priority to CA000581218A priority patent/CA1335682C/fr

1988-11-14 Priority to EP88118954A priority patent/EP0356579B1/fr

1988-11-14 Priority to DE3850498T priority patent/DE3850498T2/de

1988-12-09 Priority to JP63310274A priority patent/JP2545595B2/ja

1990-10-11 Priority to US07/595,837 priority patent/US5114652A/en

1995-05-23 Application granted granted Critical

1995-05-23 Publication of CA1335682C publication Critical patent/CA1335682C/fr

2012-05-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004760 aramid Substances 0.000 title claims abstract description 19
229920006231 aramid fiber Polymers 0.000 title claims abstract description 11
239000000049 pigment Substances 0.000 claims abstract description 103
239000000835 fiber Substances 0.000 claims abstract description 44
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 26
239000012860 organic pigment Substances 0.000 claims abstract description 16
239000002245 particle Substances 0.000 claims abstract description 14
229920003235 aromatic polyamide Polymers 0.000 claims abstract description 9
238000005406 washing Methods 0.000 claims abstract description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
-1 chloro, nitro, methyl Chemical group 0.000 claims description 10
229920000642 polymer Polymers 0.000 claims description 10
230000001112 coagulating effect Effects 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
235000019239 indanthrene blue RS Nutrition 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 6
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 claims description 5
PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 5
UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 4
FLJVQOSHSSGNRL-UHFFFAOYSA-N 3H-pyranthren-4-one Chemical compound C1=CC=CC=2C3=CC4=CC=C5C=C6C=CCC(C6=C6C=C7C=CC(=CC12)C3=C7C4=C56)=O FLJVQOSHSSGNRL-UHFFFAOYSA-N 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
239000012530 fluid Substances 0.000 claims description 3
229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 claims description 3
LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 claims description 3
238000013019 agitation Methods 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
239000007788 liquid Substances 0.000 claims 1
238000009987 spinning Methods 0.000 abstract description 8
230000015271 coagulation Effects 0.000 abstract description 6
238000005345 coagulation Methods 0.000 abstract description 6
239000002904 solvent Substances 0.000 abstract description 4
238000001035 drying Methods 0.000 abstract 1
150000003254 radicals Chemical class 0.000 description 10
238000012360 testing method Methods 0.000 description 8
230000000052 comparative effect Effects 0.000 description 7
239000000984 vat dye Substances 0.000 description 7
239000000975 dye Substances 0.000 description 6
239000004952 Polyamide Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003086 colorant Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000008859 change Effects 0.000 description 2
230000003750 conditioning effect Effects 0.000 description 2
238000002788 crimping Methods 0.000 description 2
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
238000005259 measurement Methods 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
KOTVVDDZWMCZBT-UHFFFAOYSA-N vat violet 1 Chemical compound C1=CC=C[C]2C(=O)C(C=CC3=C4C=C(C=5C=6C(C([C]7C=CC=CC7=5)=O)=CC=C5C4=6)Cl)=C4C3=C5C=C(Cl)C4=C21 KOTVVDDZWMCZBT-UHFFFAOYSA-N 0.000 description 2
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000610375 Sparisoma viride Species 0.000 description 1
QKDLQFSLLCQTOH-UHFFFAOYSA-N Trichodonin Natural products C1C(O)C2C3(COC(=O)C)C(C=O)C(C)(C)CCC3OC(=O)C22C(=O)C(=C)C1C2 QKDLQFSLLCQTOH-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
239000001055 blue pigment Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
OXEFCDNMUKTKDV-UHFFFAOYSA-N calcoloid olive r Chemical compound C=1C=CC=CC=1C(=O)NC(C1=C(C(C2=CC=CC=C2C1=O)=O)C=1NC2=C3C=4C(C5=CC=CC=C5C3=O)=O)=CC=1C2=CC=4NC(=O)C1=CC=CC=C1 OXEFCDNMUKTKDV-UHFFFAOYSA-N 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 1
238000002166 wet spinning 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
- 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
- D01F1/04—Pigments
- 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
- D01F6/605—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides from aromatic polyamides

Landscapes

Engineering & Computer Science (AREA)
Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Textile Engineering (AREA)
Manufacturing & Machinery (AREA)
Artificial Filaments (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA000581218A 1987-06-18 1988-10-25 Fibres aramides couleur Expired - Fee Related CA1335682C (fr)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
US07/226,645 US4994323A (en)	1988-08-01	1988-08-01	Colored aramid fibers
CA000581218A CA1335682C (fr)	1987-06-18	1988-10-25	Fibres aramides couleur
EP88118954A EP0356579B1 (fr)	1988-08-01	1988-11-14	Fibre colorées d'aramide
DE3850498T DE3850498T2 (de)	1988-08-01	1988-11-14	Gefärbte Aramidfasern.
JP63310274A JP2545595B2 (ja)	1988-08-01	1988-12-09	着色されたアラミド繊維
US07/595,837 US5114652A (en)	1988-08-01	1990-10-11	Process for making colored aramid fibers

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6345587A	1987-06-18	1987-06-18
CA000581218A CA1335682C (fr)	1987-06-18	1988-10-25	Fibres aramides couleur

Publications (1)

Publication Number	Publication Date
CA1335682C true CA1335682C (fr)	1995-05-23

Family

ID=25672201

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000581218A Expired - Fee Related CA1335682C (fr)	1987-06-18	1988-10-25	Fibres aramides couleur

Country Status (1)

Country	Link
CA (1)	CA1335682C (fr)

1988
- 1988-10-25 CA CA000581218A patent/CA1335682C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2010-05-25	MKLA	Lapsed

Publication	Publication Date	Title
AU628177B2 (en)	1992-09-10	PVP/para-aramid fibers and process for making them
US4994323A (en)	1991-02-19	Colored aramid fibers
CN103726124B (zh)	2018-04-27	一种原液着色对位芳纶长丝的制备方法及其产品
CA2796362A1 (fr)	2011-10-20	Fibre de polyamide entierement aromatique de type meta
WO2010035834A1 (fr)	2010-04-01	Fibre de polyamide entièrement aromatique à méta-forme aisée à colorer
US5114652A (en)	1992-05-19	Process for making colored aramid fibers
EP0295672A2 (fr)	1988-12-21	Fibres d'aramide colorées
US5662852A (en)	1997-09-02	Mass-colored formed structures based on aromatic polyamides, mass-colored fiber, and premix for producing mass-colored formed structures
CN1027655C (zh)	1995-02-15	着色的芳族聚酰胺纤维
JP2971338B2 (ja)	1999-11-02	易染性メタ型芳香族ポリアミド繊維
JP7248507B2 (ja)	2023-03-29	原着メタ型全芳香族ポリアミド繊維及びその製造方法
CA1335682C (fr)	1995-05-23	Fibres aramides couleur
JP2009120976A (ja)	2009-06-04	易染色性メタ型全芳香族ポリアミド繊維
JP2000505508A (ja)	2000-05-09	高い破断時の伸びを有するセルロースファイバー及びフィラメント
JP2010252712A (ja)	2010-11-11	魚網用アラミド繊維および魚網
JP3020750B2 (ja)	2000-03-15	芳香族ポリアミド繊維
KR100221770B1 (ko)	1999-10-01	술폰화 폴리(p-페닐렌 테레프탈아미드)의 텍스타일 섬유
US5135687A (en)	1992-08-04	Process for making PVP/para-aramid fibers
JP4603208B2 (ja)	2010-12-22	ポリケトン繊維
US5000898A (en)	1991-03-19	Process for making oriented, shaped articles of lyotropic polysaccharide/thermally-consolidatable polymer blends
KR930003221B1 (ko)	1993-04-23	고밀도 폴리에스테르 섬유의 제조방법.
JPH08170224A (ja)	1996-07-02	分散染料に可染性の有機溶剤系セルロース繊維及びその製法
JPS61160411A (ja)	1986-07-21	着色した湿式紡糸繊維の製造法
JPH10168654A (ja)	1998-06-23	シートベルト用ポリエステル繊維及びシートベルトウェビング
JPH08170219A (ja)	1996-07-02	分散染料による内外層染色差のないレーヨン・ケーク糸