EP0929532A1 - Bis-s-triazinylaminostilbenderivate als faserreaktive aufheller - Google Patents

Bis-s-triazinylaminostilbenderivate als faserreaktive aufheller

Info

Publication number: EP0929532A1
Authority: EP; European Patent Office
Prior art keywords: group; substituted; unsubstituted; optical brightener; moiety
Prior art date: 1996-10-02
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP97930211A

Other languages

English (en)

French (fr)

Inventor

Ronald P. Pedemonte

Thomas S. Phillips

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.)

Dystar LP

Original Assignee

Dystar LP

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.)

1996-10-02

Filing date

1997-06-26

Publication date

1999-07-21

1997-06-26 Application filed by Dystar LP filed Critical Dystar LP

1999-07-21 Publication of EP0929532A1 publication Critical patent/EP0929532A1/de

Status Withdrawn legal-status Critical Current

Links

QDOPPSQPRXIRRX-UHFFFAOYSA-N 1,2-diphenyl-n,n'-bis(1,3,5-triazin-2-yl)ethene-1,2-diamine Chemical compound N=1C=NC=NC=1NC(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)NC1=NC=NC=N1 QDOPPSQPRXIRRX-UHFFFAOYSA-N 0.000 title claims abstract description 5
230000003287 optical effect Effects 0.000 claims abstract description 33
239000000835 fiber Substances 0.000 claims abstract description 9
AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims abstract description 6
-1 alkali metal salts Chemical class 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 13
125000000732 arylene group Chemical group 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
150000001721 carbon Chemical group 0.000 claims 1
125000005647 linker group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 7
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000003513 alkali Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
229920000742 Cotton Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
238000005282 brightening Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
239000000463 material Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000004753 textile Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000007844 bleaching agent Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
239000012467 final product Substances 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
125000004957 naphthylene group Chemical group 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000011368 organic material Substances 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
RJQLOLOVSLLJDV-UHFFFAOYSA-N ClC1=CC(=NN=N1)Cl.N(CCO)CCO Chemical compound ClC1=CC(=NN=N1)Cl.N(CCO)CCO RJQLOLOVSLLJDV-UHFFFAOYSA-N 0.000 description 1
REJHVSOVQBJEBF-UHFFFAOYSA-N DSD-acid Natural products OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000005998 bromoethyl group Chemical group 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
BABGJWKHPIEPSB-UHFFFAOYSA-N cyano(sulfo)carbamic acid Chemical compound S(=O)(=O)(O)N(C#N)C(=O)O BABGJWKHPIEPSB-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
ROPLCSFPUPWHGJ-UHFFFAOYSA-N hydroxycyanamide Chemical compound ONC#N ROPLCSFPUPWHGJ-UHFFFAOYSA-N 0.000 description 1
FPLFMJUPDWYPHQ-UHFFFAOYSA-N n-[2-(2-phenylethenyl)phenyl]triazin-4-amine Chemical class C=1C=CC=C(C=CC=2C=CC=CC=2)C=1NC1=CC=NN=N1 FPLFMJUPDWYPHQ-UHFFFAOYSA-N 0.000 description 1
WCYPKKVZRJWFFF-UHFFFAOYSA-N n-[4-[2-[4-(1,3,5-triazin-2-ylamino)phenyl]ethenyl]phenyl]-1,3,5-triazin-2-amine Chemical compound N=1C=NC=NC=1NC(C=C1)=CC=C1C=CC(C=C1)=CC=C1NC1=NC=NC=N1 WCYPKKVZRJWFFF-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000002964 rayon Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/272—Unsaturated compounds containing sulfur atoms
- D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/68—Triazinylamino stilbenes
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/614—Optical bleaching or brightening in aqueous solvents
- D06L4/621—Optical bleaching or brightening in aqueous solvents with anionic brighteners
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
- D06M13/03—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons with unsaturated hydrocarbons, e.g. alkenes, or alkynes
- D06M13/07—Aromatic hydrocarbons
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/262—Sulfated compounds thiosulfates
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/44—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing nitrogen and phosphorus
- D06M13/453—Phosphates or phosphites containing nitrogen atoms
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/10—Animal fibres
- D06M2101/12—Keratin fibres or silk
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/34—Polyamides

Definitions

the bis-s-triazinyiaminostilbene based brighteners represent the largest
Ackermann et al discloses the use and preparation of this class of brighteners.
bleaching agent i.e. peroxide
This invention is that of an optical brightener of the bis-s-
triazinylaminostilbene series having at least one fiber reactive vinyl sulfone
R 3 is selected from hydrogen, a substituted or unsubstituted phenyl, a
W is selected from a substituted or unsubstituted arylene, e.g. phenylene
carbons e.g. methylene, ethylene and propylene, or two or three of said
arylene and alkylene groups in combination, e.g. arylene - alkylene or
Y is selected from vinyl, 2-sulfatoethyl, 2-thiosulfatoethyl, 2-
a is a number selected from 0 and 1 ;
b is a number selected from 1 and 2; with the proviso that the sum of a +
x is a number selected from 1 to 8.
the compounds of the invention are useful in the optical brightening of
Optical brighteners are typically applied in relatively low concentrations
the groups G and B are independently selected from substituted and
aromatic and aliphatic amines are hydrogen, cyano, phenoxy,
Novel fiber-reactive brighteners which may be used in significantly lower
G represents alkoxy substituent of one to four carbon atoms
R ⁇ and R 2 are independently selected from hydrogen, a lower
alkyl of one to four carbon atoms a lower alkoxy of one to four carbons
nitrogen atom are not bounded to the same carbon atom, cyano, or a
Q is a group of the formula (2a) or (2b):
R 3 is selected from hydrogen, an unsubstituted or substituted phenyl
phenyl moiety may be substituted by
alkoxy of 1 to 4 carbon atoms e.g. methoxy and
alkyl of 1 to 4 carbon atoms e.g. methyl
sulfo carboxy
cyclohexyl which may be substituted by halogen, (e.g. chlorine and
alkoxy having 1 to 4 carbon atoms e.g. methoxy and ethoxy
alkyl having 1 to 4 carbon atoms, (e.g. methyl and ethyl), sulfo and carboxy.
the alkyl moiety may be substituted by substituents such as
alkyl moiety may also be substituted by C, to C 4 alkoxy, hydroxyl, cyano,
W is selected from a substituted or unsubstituted arylene radical, e g
phenylene and naphthylene or a substituted or unsubstituted alkylene or
alkylene is intended to mean a branched or straight
chained moiety having 1 to 8, preferably 2 to 6, and in particular 2 to 4
the arylene radicals can be interrupted by 1 or more,
hetero groups such as nitrogen, or oxygen or sulfur
radicals can in each case be joined together by such a group or a
Suitable substituents for the arylene group include halogen (Cl, F, Br),
Suitable substituents for the alkylene group include halogen (Cl, F, Br),
Y is the vinyl group or a 2-sulfatoethyl, 2-thiosulfatoethyl or 2-
bromoethyl or 2-chloroethyl group preferably the vinyl group and in
a is the number zero or 1
the brighteners of this invention are suitable for the optical
fibers such as cotton staple fiber, rayon, wool and nylon
the brighteners are applied at the exhaust method.
the brighteners are applied under alkaline conditions and in combination with bleaching agents such
the first step of the reaction is carried out preferably at
the final fiber-reactive optical brightener was obtained by adding 39.1
aminobenzene-4-(2-sulfatoethyl)-sulfone replaced the 1-aminobenzene-3-(2-aminobenzene)
optical brightener of the invention was applied to cotton fabric gray
Table 2 Comparison of Whiteness Values for C.I. Optical Brightener 28 versus Example 1 at 105 °F with alkali.
Example 1 has less whiteness than Cl. 28 at 0.40 and 0.80% depths due to saturation of the brightener on the cotton, therefore creating a yellowing effect.
Table 3 Comparison of Whiteness Values for C.I. Optical Brightener 28 versus Example 1 at 140 °F with alkali.
Table 4 Comparison of Whiteness Values for C. I. Optical Brightener 28 versus Example 1 at 160 °F with alkali.
Table 5 Comparison of Whiteness Values for C. I. Optical Brightener 28 versus Example 1 at 175 °F with alkali.
Table 6 Comparison of Whiteness Values for Ackermann 425 Brightener versus Examples 7 and 8 at 140 °F with alkali.

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Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Materials Engineering (AREA)
Detergent Compositions (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Compositions Of Macromolecular Compounds (AREA)
Optical Filters (AREA)

EP97930211A 1996-10-02 1997-06-26 Bis-s-triazinylaminostilbenderivate als faserreaktive aufheller Withdrawn EP0929532A1 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US2714196P	1996-10-02	1996-10-02
US27141P		1996-10-02
PCT/US1997/010948 WO1998014435A1 (en)	1996-10-02	1997-06-26	Fiber-reactive brighteners of bis-s-triazinylaminostilbene

Publications (1)

Publication Number	Publication Date
EP0929532A1 true EP0929532A1 (de)	1999-07-21

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EP97930211A Withdrawn EP0929532A1 (de)	1996-10-02	1997-06-26	Bis-s-triazinylaminostilbenderivate als faserreaktive aufheller

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EP (1)	EP0929532A1 (de)
JP (1)	JP2001507725A (de)
KR (1)	KR20000048764A (de)
AU (1)	AU3409597A (de)
CA (1)	CA2268139A1 (de)
TR (1)	TR199900720T2 (de)
WO (1)	WO1998014435A1 (de)

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TWI252270B (en)	2000-07-20	2006-04-01	Ciba Sc Holding Ag	A method for the fluorescent whitening of cotton
CN102906239B (zh)	2010-05-18	2015-09-09	美利肯公司	荧光增白剂及含有其的组合物
CN102993111B (zh) *	2011-06-30	2015-11-25	上海安诺其集团股份有限公司	4,4’-二氨基二苯乙烯-2,2’-二磺酸衍生物的制备方法

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BE559784A (de) *
CH597204A5 (de) *	1973-02-16	1978-03-31	Sandoz Ag
CH610312A5 (de) *	1973-09-21	1979-04-12	Hoechst Ag
CH640899A5 (en) *	1979-05-14	1984-01-31	Ciba Geigy Ag	Stable stilbene brightener solutions
GB9503474D0 (en) *	1995-02-22	1995-04-12	Ciba Geigy Ag	Compounds and their use

1997
- 1997-06-26 EP EP97930211A patent/EP0929532A1/de not_active Withdrawn
- 1997-06-26 JP JP51649898A patent/JP2001507725A/ja active Pending
- 1997-06-26 AU AU34095/97A patent/AU3409597A/en not_active Abandoned
- 1997-06-26 KR KR1019990702750A patent/KR20000048764A/ko not_active Withdrawn
- 1997-06-26 CA CA002268139A patent/CA2268139A1/en not_active Abandoned
- 1997-06-26 WO PCT/US1997/010948 patent/WO1998014435A1/en not_active Ceased
- 1997-06-26 TR TR1999/00720T patent/TR199900720T2/xx unknown

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Title
See references of WO9814435A1 *

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Publication number	Publication date
AU3409597A (en)	1998-04-24
TR199900720T2 (xx)	1999-07-21
KR20000048764A (ko)	2000-07-25
WO1998014435A1 (en)	1998-04-09
CA2268139A1 (en)	1998-04-09
JP2001507725A (ja)	2001-06-12

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2003-07-09	18D	Application deemed to be withdrawn	Effective date: 20030103

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