CN112805274A - 新型吡啶和嘧啶取代的三嗪紫外线吸收剂 - Google Patents
新型吡啶和嘧啶取代的三嗪紫外线吸收剂 Download PDFInfo
- Publication number
- CN112805274A CN112805274A CN201980065083.3A CN201980065083A CN112805274A CN 112805274 A CN112805274 A CN 112805274A CN 201980065083 A CN201980065083 A CN 201980065083A CN 112805274 A CN112805274 A CN 112805274A
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- Prior art keywords
- formula
- compound
- dyeing
- hydrogen
- fibre materials
- 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.)
- Granted
Links
- 150000003918 triazines Chemical class 0.000 title claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 4
- 239000006096 absorbing agent Substances 0.000 title description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000000835 fiber Substances 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 23
- 239000004753 textile Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000004043 dyeing Methods 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 229920000728 polyester Polymers 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 9
- 230000006641 stabilisation Effects 0.000 claims description 8
- 238000011105 stabilization Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000975 dye Substances 0.000 description 13
- 239000004744 fabric Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- -1 2-ethylhexyl Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- NSWIROGSZPXREF-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-benzoxazin-4-one Chemical compound OC1=CC=CC=C1C1=NC(=O)C2=CC=CC=C2O1 NSWIROGSZPXREF-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 235000013351 cheese Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000986 disperse dye Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical class OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- 229960000581 salicylamide Drugs 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000012192 staining solution Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000009976 warp beam dyeing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PLNYIXJTLLMSKR-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)-6-pyridin-4-yl-1,3,5-triazin-2-yl]phenol Chemical compound OC1=C(C=CC=C1)C1=NC(=NC(=N1)C1=C(C=CC=C1)O)C1=CC=NC=C1 PLNYIXJTLLMSKR-UHFFFAOYSA-N 0.000 description 1
- IUTJKZSHIDXEQU-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)-6-pyrimidin-2-yl-1,3,5-triazin-2-yl]phenol Chemical compound OC1=C(C=CC=C1)C1=NC(=NC(=N1)C1=C(C=CC=C1)O)C1=NC=CC=N1 IUTJKZSHIDXEQU-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-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
- FBWSRAOCSJQZJA-UHFFFAOYSA-N 4-iminonaphthalen-1-one Chemical compound C1=CC=C2C(=N)C=CC(=O)C2=C1 FBWSRAOCSJQZJA-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 240000002129 Malva sylvestris Species 0.000 description 1
- 235000006770 Malva sylvestris Nutrition 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 101100539936 Mus musculus Utp20 gene Proteins 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- IONKMFGAXKCLMI-UHFFFAOYSA-N [amino(pyridin-4-yl)methylidene]azanium;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=NC=C1 IONKMFGAXKCLMI-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009975 hank dyeing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/46—Aromatic cyclic groups
- C09B68/467—Heteroaromatic groups
- C09B68/4677—6-Membered rings
- C09B68/46775—Triazine
-
- 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
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- 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
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/445—Use of auxiliary substances before, during or after dyeing or printing
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
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Abstract
Description
本发明涉及衍生自羟苯基-s-三嗪类的紫外线吸收剂(UVA)、它们的制备方法和它们用于染色或未染色的纺织材料的光化学稳定化的用途。
用于纺织纤维材料,尤其是合成纺织纤维材料的染色或印花(printing)的分散染料当受到光的作用时,尤其当同时受到热的作用时在一些情况下严重受损。为了避免这样的损害,在将用于汽车或泳衣行业或用于所谓“户外”用品的纤维染色时,将紫外线吸收剂(UVA)添加到染色液和印花浆中。
EP-A 0 468 921描述了包含羟苯基-s-三嗪作为UVA的水性分散体,其适合作为纺织纤维的光稳定剂并以良好的运输和储存稳定性为特征。
但是,已知的三嗪UVA没有充分满足尤其汽车工业提出的高要求。
现在已经发现,含有杂芳族取代基的三嗪基UVA的施加提供优异的耐光牢度和热耐光牢度(hot light fastness)性质。
本发明涉及下式的化合物
其中V、W、X和Y代表N或CH,V、W、X和Y中的至少一个是N,且V、W、X和Y中的至少两个是CH;和
R1、R2和R3各自互相独立地为氢、C1-C8烷基、C1-C8烷氧基、硝基、氰基、三氟甲基、卤素或羟基;
条件是不包括下式的化合物
作为基团R1、R2或R3的烷基和烷氧基可以是直链或支链的。
烷基的实例是甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、新戊基、正己基、2-乙基己基、正辛基和异辛基。
合适的烷氧基是例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、异丁氧基、正戊氧基、新戊氧基、正己氧基、2-乙基己氧基、正辛氧基和异辛氧基。
卤素是例如氟、溴或优选氯。
优选的是其中X是N且V、W和Y是CH的如上文定义的式(1)的化合物。
进一步优选的是其中Y是N且V、W和X是CH的如上文定义的式(1)的化合物。
进一步优选的如上文定义的式(1)的化合物是其中V是N且W、X和Y是CH的那些。
进一步优选的是其中X和W表示N且V和Y是CH的如上文定义的式(1)的化合物。
式(1)中的R1优选是氢或甲氧基。
式(1)中的R2优选是氢或羟基。
式(1)中的R3优选是氢或甲氧基。
式(1)的化合物可根据已知方法,例如通过Helv. Chim. Acta 55, 1566 (1972)中描述的方法制备。
相应地,本发明进一步涉及一种制备如上文定义的式(1)的化合物的方法,其包括
(I). 通过水杨酰胺衍生物(2)与羧酸(3)的酸催化的闭环反应,制备2-芳基-4H-1,3-苯并噁嗪-4-酮(4)
和
(II). 使由此获得的2-芳基-4H-1,3-苯并噁嗪-4-酮(4)与脒(5)反应以提供式(1)的三嗪衍生物,
其中R1、R2、R3、X、Y、V和W如上文定义。
式(1)的化合物优选以基于纤维材料的重量计0.01-15.0重量%,更优选0.1-10.0重量%,特别是0.5-7.0重量%的量施加。
该新型UVA尤其适用于未染色的、染色的或印花的纺织纤维材料的光化学稳定化,这也是本发明提供的。
相应的方法包括用含有至少一种上式(1)的化合物的液体(liquor)处理纺织纤维材料。
适用于处理的纺织纤维材料主要是含有聚酯或醋酸纤维素的纤维材料。术语聚酯纤维应被理解为是指,例如,纤维素酯纤维,如二次醋酸纤维素纤维(secondary celluloseacetate fibres)和三醋酸纤维,尤其是可能经过酸改性的线性聚酯纤维,这样的纤维例如通过对苯二甲酸与乙二醇或间苯二甲酸或对苯二甲酸与1,4-双(羟甲基)环己烷的缩合获得,以及对苯二甲酸和间苯二甲酸与乙二醇的共聚物的纤维。纺织纤维工业中的常规聚酯纤维特别由对苯二甲酸和乙二醇组成。
要处理的纺织纤维材料也可以是聚酯纤维和其它纤维的混纺织物,实例是聚丙烯腈/聚酯、聚酰胺/聚酯、聚酯/棉、聚酯/粘胶或聚酯/羊毛纤维的混纺物,其在常规分批或连续程序中印花或染色。
根据本发明的方法特别适用于聚酯纤维或聚酯纤维和其它纤维的混纺织物,如PAN/PES、PA/PES、PES/CO和PES/WO的稳定化。
纤维可以在根据本发明的方法中以任何常规形式,例如以微纤维的形式施用。
相应地,本发明进一步涉及纺织纤维材料的稳定化方法,其中所述纺织纤维材料包含聚酯纤维。
该新型UVA略溶于水,因此以分散形式施加。为此,根据应用条件,使用例如适当的分散剂并借助例如石英珠和高速搅拌器将它们研磨到大约 0.1 – 3.0 µm的粒度。
可在纺织材料的染色过程之前、之中或之后进行根据本发明的UVA的施加。
优选与染料同时施加UVA,即在浸染(exhaust)或轧染(padding)过程中将其添加到染色液中。
相应地,本发明涉及染色的纺织纤维材料的光化学稳定化方法,其中作为染色液的一部分施加式(1)的化合物。
仅极微溶于水并且大多以微细分散体的形式存在于染色液中的所用分散染料可属于范围广泛的染料种类,例如吖啶酮、偶氮、蒽醌、香豆素、甲烷、紫环酮(perinone)、萘醌-亚胺、喹酞酮(quinophthalone)、苯乙烯型或硝基染料。在本发明的实践中也可以使用分散染料的混合物。
添加到液体中的染料量取决于所需色调深度;基于所用纺织材料计,合适的量通常为0.01至10.0重量%,优选0.02至5.0重量%。
可通过连续或分批程序由水性液进行根据本发明的UVA的施加,任选与染色结合。
在连续染色程序的情况下,借助例如轧染(pad-mangling)、喷涂或knit padding将除染料外还可包括另外的辅助剂的染色液施加到块材(piece material)上,并使用热固色(thermofix)或HT蒸汽法显色。
在分批程序(浸染程序)的情况下,可在宽范围内,例如从1 : 1至1 : 100,优选1 :6至1 : 50选择液比。进行染色的温度为至少50℃,通常不超过140℃。其优选在80℃至135℃的范围内。
有利地通过使用水性液的浸染法进行根据本发明的UVA的施加。液比优选为1:3至1:50,尤其是1:5至1:30。在施加过程中的液温度优选为70℃至140℃,尤其是80℃至135℃。
优选通过在封闭耐压装置中在> 100℃,优选110℃至135℃的温度下和在大气压或超大气压下的高温法处理线性聚酯纤维。合适的封闭容器的实例是循环装置,如筒子纱或经轴染色装置(cheese or beam dyeing apparatus)、纱盘染槽(winch becks)、喷射或drim染色机、袖笼绞纱染色装置(muff dyeing apparatus)、桨或卷染机(jiggers)。
除式(1)的化合物和染料外,根据本发明的液体还可包含另外的常规添加剂,例如染色助剂、稳定剂、络合剂、载体、增稠剂、粘尘剂、阴离子或非离子分散剂、润湿剂、隔离剂、防霜剂、防沫剂、防腐剂和杀菌剂。
染色浴可另外含有无机酸,例如硫酸或磷酸,或更方便地,有机酸,例如脂族羧酸,如甲酸、乙酸、草酸或柠檬酸,和/或盐,如乙酸铵、硫酸铵或乙酸钠。酸的用途特别是建立根据本发明使用的液体的pH,其优选在4至6之间,特别是在4.5至5.5之间。
有利地将包含根据本发明的UVA、染料和(如果适当)另外的辅助剂的染色液调节到4.5至5.5的pH。将浸染温度以2℃/min的速率从30℃提高到135℃并在该值保持15至90分钟。
然后将染色液冷却到60至80℃。用水洗涤纤维材料并且如果必要,施以在碱性介质中的清理处理(clearing treatment)。此后再冲洗染色纤维并干燥。
要用根据本发明的UVA处理的纺织纤维材料可为各种组成形式,例如作为松散材料、布匹(piece goods)如针织或机织布或作为在例如筒子(cheeses)、经轴等上的纱线。后者可具有200至600 g/l,特别是400至450 g/l的包装密度。
通过施加式(1)的化合物获得的染色或印花以出色的耐光牢度,特别是热耐光牢度性质为特征,因此尤其适用于汽车或泳衣行业或所谓“户外”用品中所用的纤维。
以下实施例例示本发明。
I. 合成实施例
实施例I.1
以下化合物的合成
将水杨酸(20.9 g)、水杨酰胺(21.0 g)、N,N’-二甲基甲酰胺(0.5 ml)和二甲苯(70 ml)的混合物加热到110℃,然后逐滴加入亚硫酰氯(36.0 g)。反应混合物在126℃下搅拌5小时。在反应完成后,将反应混合物在10℃下逐渐冷却,然后搅拌1小时。过滤沉淀物并用甲醇洗涤,并在真空下干燥以产生2-(2-羟苯基)-4H-1,3-苯并噁嗪-4-酮(19.1 g)。
在室温下将30%甲醇钠/甲醇(13.0 g)添加到根据美国专利6,004,965的专利制备的甲醇(140 ml)和4-吡啶甲脒盐酸盐(7.5 g)的混合物中。然后在35℃下加入2-(2-羟苯基)-4H-1,3-苯并噁嗪-4-酮(12.1 g)。反应混合物在50℃下搅拌4小时。在反应混合物冷却到室温后,通过抽吸过滤收集沉淀物,用甲醇和水洗涤并在真空下在60℃下干燥以产生2,4-双(2-羟苯基)-6-(4-吡啶基)-1,3,5-三嗪(8.9 g)。熔点: 258-260℃。λmax= 280 nm /352 nm。
实施例I.2
以下化合物的合成
将水杨酸(132 g)、水杨酰胺 (126 g)、N,N’-二甲基甲酰胺(3 ml)和二甲苯(240ml)的混合物加热到110℃,然后逐滴加入亚硫酰氯(216 g)。反应混合物在126℃下搅拌5小时。在反应完成后,将反应混合物在10℃下逐渐冷却,然后搅拌1小时。过滤沉淀物并用甲醇洗涤,并在真空下干燥以产生2-(2-羟苯基)-4H-1,3-苯并噁嗪-4-酮(143 g)。
在室温下将30%甲醇钠/甲醇(9.0 g)添加到根据WO 2011/024056 A2的专利制备的甲醇(140 ml)和2-嘧啶甲脒盐酸盐(7.9 g)的混合物中。然后在35℃下加入2-(2-羟苯基)-4H-1,3-苯并噁嗪-4-酮(12.6 g)。反应混合物在50℃下搅拌4小时。在反应混合物冷却到室温后,通过抽吸过滤收集沉淀物,用甲醇和水洗涤并在真空下在60℃下干燥以产生2,4-双(2-羟苯基)-6-(2-嘧啶基)-1,3,5-三嗪(11.8 g)。熔点: 321-325℃(分解)。λmax= 280nm / 354 nm。
实施例I.3 – I.16
类似于实施例I.1中描述的程序,制备表1中所列的化合物。
II. 应用实施例
II.1. 聚酯的染色
10克PES针织物(5-4212)的试样通过实验室高温染色机Labomat BFA-16(Mathis)用染色液根据浸染法(液比1 : 20,60 min/135℃)染色,所述染色液含有
1.0 g/l硫酸铵,
0.5 g/l润湿剂,
1.0 g/l分散剂,
以及基于织物重量计0.218重量%的染料Teratop® Yellow HL-G-01 150%(Huntsman供应)、基于织物重量计0.112重量%的染料Teratop® Red HL(Huntsman供应)和基于织物重量计0.142重量%的染料Teratop® Blue HL-B 150%(Huntsman供应)和各自以表2中给出的量的式(103)、(111)或(127)的化合物。
在冷却到大约80℃后,用清理液(clearing liquor)对试样施以还原后处理(20min/ 75℃),所述清理液含有
2.0 g/l连二亚硫酸钠,
5.0 g/l 30% NaOH,
1.0 g/l皂洗剂(Eriopon® OS,Huntsman供应),
随后用水冲洗并干燥。
根据DIN 75202 (FAKRA)测试由此获得的染色的热耐光牢度。结果概括在表2中。
表2中的百分比是重量%并相对于织物的重量。
表2:
用不同量的UVA获得的灰色染色的热耐光牢度评级*
* 根据灰色标度ISO 105-A02的1至5十进制评级。
II.2. 聚酯的染色
10克PES针织物(5-4212)的试样通过实验室高温染色机Labomat BFA-16(Mathis)用染色液根据浸染法(液比1 : 20,60 min/135℃)染色,所述染色液含有
1.0 g/l硫酸铵,
0.5 g/l润湿剂,
1.0 g/l分散剂,
以及基于织物重量计0.20重量%的染料Teratop® Yellow HL-G-01 150%(Huntsman供应)、基于织物重量计0.11重量%的染料Teratop® Red HL(Huntsman供应)和基于织物重量计0.26重量%的染料Teratop® Blue HL-GR(Huntsman供应)和各自以表3中给出的量的式(110)、(116)、(121)、(133)或(145)的化合物。
在冷却到大约80℃后,用清理液(clearing liquor)对试样施以还原后处理(20min/ 75℃),所述清理液含有
2.0 g/l连二亚硫酸钠,
5.0 g/l 30% NaOH,
1.0 g/l皂洗剂(Eriopon® OS,Huntsman供应),
随后用水冲洗并干燥。
根据DIN 75202 (FAKRA)测试由此获得的染色的热耐光牢度。结果概括在表3中。
表3中的百分比是重量%并相对于织物的重量。
表3:
用不同量的UVA获得的灰色染色的热耐光牢度评级*
*根据灰色标度ISO 105-A02的1至5十进制评级。
Claims (13)
2.根据权利要求1所述的式(1)的化合物,其中X是N且V、W和Y是CH。
3.根据权利要求1所述的式(1)的化合物,其中Y是N且V、W和X是CH。
4.根据权利要求1所述的式(1)的化合物,其中V是N且W、X和Y是CH。
5.根据权利要求1所述的式(1)的化合物,其中X和W表示N且V和Y是CH。
6.根据前述权利要求任一项所述的式(1)的化合物,其中R1是氢或甲氧基。
7.根据前述权利要求任一项所述的式(1)的化合物,其中R2是氢或羟基。
8.根据前述权利要求任一项所述的式(1)的化合物,其中R3是氢或甲氧基。
10.未染色的、染色的或印花的纺织纤维材料的光化学稳定化方法,其包括用含有至少一种根据权利要求1所述的式(1)的化合物的液体处理纺织纤维材料。
11.根据权利要求10所述的方法,其中所述纺织纤维材料包含聚酯纤维。
12.根据权利要求10所述的染色的纺织纤维材料的光化学稳定化方法,其中作为染色液的一部分施加式(1)的化合物。
13.根据权利要求1所述的式(1)的化合物用于未染色的、染色的或印花的纺织纤维材料的光化学稳定化的用途。
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BR (1) | BR112021005362A8 (zh) |
CA (1) | CA3114269A1 (zh) |
MX (1) | MX2021003715A (zh) |
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- 2019-09-17 JP JP2021518148A patent/JP2022504115A/ja active Pending
- 2019-09-17 KR KR1020217013473A patent/KR20210072041A/ko not_active Application Discontinuation
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- 2019-09-17 CA CA3114269A patent/CA3114269A1/en active Pending
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- 2019-09-17 EP EP19780161.6A patent/EP3860986A1/en active Pending
- 2019-09-17 WO PCT/EP2019/074848 patent/WO2020069851A1/en active Application Filing
- 2019-09-17 MX MX2021003715A patent/MX2021003715A/es unknown
- 2019-09-17 CN CN201980065083.3A patent/CN112805274B/zh active Active
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KR20210072041A (ko) | 2021-06-16 |
TWI835843B (zh) | 2024-03-21 |
US11840804B2 (en) | 2023-12-12 |
WO2020069851A1 (en) | 2020-04-09 |
CN112805274B (zh) | 2024-06-25 |
US20210340705A1 (en) | 2021-11-04 |
JP2022504115A (ja) | 2022-01-13 |
CA3114269A1 (en) | 2020-04-09 |
MX2021003715A (es) | 2021-06-04 |
BR112021005362A2 (pt) | 2021-06-15 |
BR112021005362A8 (pt) | 2023-05-09 |
TW202024049A (zh) | 2020-07-01 |
EP3860986A1 (en) | 2021-08-11 |
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