CN114805059A - Multi-element carboxy aldehyde compound and preparation and application thereof - Google Patents
Multi-element carboxy aldehyde compound and preparation and application thereof Download PDFInfo
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- CN114805059A CN114805059A CN202210240619.4A CN202210240619A CN114805059A CN 114805059 A CN114805059 A CN 114805059A CN 202210240619 A CN202210240619 A CN 202210240619A CN 114805059 A CN114805059 A CN 114805059A
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- Prior art keywords
- aldehyde compound
- salt
- ironing
- polycarboxylic
- sucrose
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Links
- -1 carboxy aldehyde compound Chemical class 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title description 17
- 239000004744 fabric Substances 0.000 claims abstract description 92
- 238000010409 ironing Methods 0.000 claims abstract description 81
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 48
- 238000005406 washing Methods 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 229930006000 Sucrose Natural products 0.000 claims description 65
- 239000005720 sucrose Substances 0.000 claims description 64
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 58
- 239000011347 resin Substances 0.000 claims description 34
- 229920005989 resin Polymers 0.000 claims description 34
- 238000004043 dyeing Methods 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000007493 shaping process Methods 0.000 claims description 23
- 239000007800 oxidant agent Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 21
- 230000001590 oxidative effect Effects 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 8
- 238000005096 rolling process Methods 0.000 claims description 8
- 238000007730 finishing process Methods 0.000 claims description 3
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002462 imidazolines Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 40
- 125000003172 aldehyde group Chemical group 0.000 abstract description 22
- 239000003431 cross linking reagent Substances 0.000 abstract description 21
- 230000000694 effects Effects 0.000 abstract description 20
- 102000004169 proteins and genes Human genes 0.000 abstract description 14
- 108090000623 proteins and genes Proteins 0.000 abstract description 14
- 150000001875 compounds Chemical group 0.000 abstract description 11
- 238000004132 cross linking Methods 0.000 abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract description 8
- 230000014759 maintenance of location Effects 0.000 abstract description 8
- 150000002373 hemiacetals Chemical class 0.000 abstract description 6
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 229960004793 sucrose Drugs 0.000 description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 230000000052 comparative effect Effects 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000975 dye Substances 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000004698 Polyethylene Substances 0.000 description 13
- 229920000573 polyethylene Polymers 0.000 description 13
- 239000006081 fluorescent whitening agent Substances 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000004902 Softening Agent Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 7
- 229920001744 Polyaldehyde Polymers 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 230000037303 wrinkles Effects 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000000149 penetrating effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 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 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 2
- 102000016938 Catalase Human genes 0.000 description 2
- 108010053835 Catalase Proteins 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 150000007854 aminals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- UHXQPQCJDDSMCB-UHFFFAOYSA-L disodium;3-[[9,10-dioxo-4-(2,4,6-trimethyl-3-sulfonatoanilino)anthracen-1-yl]amino]-2,4,6-trimethylbenzenesulfonate Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=C(C)C(S([O-])(=O)=O)=C1C UHXQPQCJDDSMCB-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 229910052743 krypton Inorganic materials 0.000 description 2
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052754 neon Inorganic materials 0.000 description 2
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 2
- 239000002357 osmotic agent Substances 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000004671 silicon softener Substances 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 125000000185 sucrose group Chemical group 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 description 1
- RNTNZRPCYDDMIA-UHFFFAOYSA-M 4478-76-6 Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C2C3=C1C(=O)C1=CC=CC=C1C3=CC(=O)N2C RNTNZRPCYDDMIA-UHFFFAOYSA-M 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- PVNWKEJJRURFHC-UHFFFAOYSA-N C(C(C(CC(=O)O)C(=O)O)C(=O)O)C(=O)O.CCCC Chemical compound C(C(C(CC(=O)O)C(=O)O)C(=O)O)C(=O)O.CCCC PVNWKEJJRURFHC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 241000872931 Myoporum sandwicense Species 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L acid green 5 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 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/325—Saturated compounds containing more than one carboxyl group containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/373—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in doubly bound form
-
- 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
- D06M13/10—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 oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention relates to the technical field of non-ironing finishing, in particular to a multi-carboxyl aldehyde compound and a salt thereof, wherein the structural general formula of the multi-carboxyl aldehyde compound is
R 1 ＝O，R 2 、R 3 、R 4 Each independently represents S or O. The conventional non-ironing finishing agent containing the multi-carboxyl aldehyde compound simultaneously contains hydroxyl and aldehyde groups, acetal or hemiacetal can be formed in molecules and among cross-linking agent molecules, and the cross-linking effect of the non-ironing finishing agent and fabrics is reduced. The polybasic carboxylic aldehyde compound of the invention can be used as a non-ironing finishing agent to avoid the problemAnd meanwhile, the compound structure can be more effectively crosslinked with protein on fabrics, particularly silk. The DP grade of the finished silk fabric is still more than or equal to 3.5 after 50 times of washing, the whiteness is reduced within 10 degrees, the breaking strength retention rate is more than or equal to 80 percent, the tearing strength increase rate is more than or equal to 100 percent, and the formaldehyde emission is 0.
Description
Technical Field
The invention relates to the technical field of non-ironing finishing, in particular to a multi-carboxyl aldehyde compound and preparation and application thereof.
Background
The present non-ironing finishing agent used in the industry on a large scale is still N-hydroxymethyl resin which endows the fabric with excellent non-ironing performance, but even if a large amount of formaldehyde catching agent is added into the finishing liquid, the resin still releases formaldehyde, and the resin cannot be suitable for the clothes of infants.
The present non-ironing finishing process of colored fabric, no matter dry crosslinking, wet crosslinking or damp crosslinking, dyes the fabric firstly, then carries out non-ironing finishing processing on the dyed fabric, and the finishing agent used in the non-ironing finishing can affect the color light of the color more or less, thereby limiting the application range of a plurality of formaldehyde-free crosslinking agents with better performance. Like the most well known polycarboxylic finish 1,2,3, 4-butanetetracarboxylic Butane (BTCA), BTCA has the major problem that the yellowing of the finished fabric is severe and that the reactive dye dyed fabric produces a large color difference (Δ E >1) after the easy-care finish. More finishing agents are recently reported to be polyaldehyde compounds, for example, tetra-aldehyde oxidized sucrose is reported, although the finished cotton fabric can achieve the advantages of high whiteness, small strength loss, no formaldehyde release and the like, the highest wrinkle recovery angle of the fabric after the non-ironing finishing is 240.7, and the non-ironing grade of the fabric is hardly up to more than 3.5 specified by the national standard. There are also reports on a method for preparing carboxyl oligouronic acid from oligosaccharide as a raw material by a two-step oxidation method consisting of NaClO/NaBr/TEMPO and sodium periodate, wherein the used oxidizing agents such as NaClO, TEMPO, periodate and iodate are difficult to completely remove, the excessive oxidizing agents in the solution can cause strong damage to the treated fabric or damage to the structure of the dye on the fabric, and more importantly, according to the reported results, the machine washing resistance of the finished cotton fabric is far inferior to that of the N-hydroxymethyl resin because the polyaldehyde non-ironing finishing agent and the cotton fabric form acetal groups. Therefore, the multi-aldehyde crosslinking agents are not suitable for the easy-care finishing of pure cotton fabrics in the prior art. Generally speaking, the multi-aldehyde crosslinking agent also has the problems of low non-ironing grade, poor machine washing resistance of the existing non-formaldehyde non-ironing finishing technology, color difference of the existing ultralow-formaldehyde non-ironing finishing technology, large control workload and the like, and no non-ironing finishing agent which can simultaneously meet the requirements of durable whiteness, fastness, high appearance grade, high recovery angle and high tear strength retention rate is found.
In addition, the application process of the existing non-ironing finishing is dyeing firstly and then non-ironing finishing, and if the formaldehyde-free finishing agent can realize dyeing after non-ironing, the workload of color difference control in the non-ironing processing process of the yarn dyed fabric can be greatly reduced.
Therefore, the need of providing a multi-carboxyl aldehyde easy-care finishing agent suitable for fabrics, especially silk fabrics, which can simultaneously meet the product performance requirements of durable whiteness, fastness, high appearance grade, high recovery angle and high tear strength retention rate, and can meet the requirements of dyeing before easy-care finishing treatment is needed.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. Therefore, the invention provides a multi-carboxyl aldehyde compound and preparation and application thereof, and aims to solve the problems that a multi-aldehyde crosslinking agent is not high in non-ironing grade, the existing formaldehyde-free non-ironing finishing technology is poor in machine washing resistance, the existing ultralow formaldehyde non-ironing finishing technology is large in color difference control workload and the like. The DP grade of the finished silk fabric is still more than or equal to 3.5 after 50 times of washing, the whiteness is reduced within 10 degrees, the breaking strength retention rate is more than or equal to 80 percent, the tearing strength increase rate is more than or equal to 100 percent, and the formaldehyde emission is 0.
The invention conception of the invention is as follows: the conventional non-ironing finishing agent containing the multi-carboxyl aldehyde compound simultaneously contains hydroxyl and aldehyde groups, acetal or hemiacetal can be formed in molecules and among cross-linking agent molecules, and the cross-linking effect of the non-ironing finishing agent and fabrics is reduced. The polybasic carboxylic aldehyde compound of the invention can avoid the problem as a non-ironing finishing agent, and the compound structure can be more effectively crosslinked with protein on fabrics, particularly silk, and the problems are as follows: 1. the aldehyde group participates in an acetal reaction or an aminal reduction reaction and is combined with units such as tryptophan, arginine and the like on the protein; 2. hypophosphorous acid is used as a catalyst, and carboxyl is combined with protein; 3. carboxylic acids can also form ionic bonds with amino groups in proteins.
The invention provides a multi-carboxyl aldehyde compound and a salt thereof, wherein the structural general formula of the multi-carboxyl aldehyde compound is shown in the specification
R 1 ＝O，R 2 、R 3 、R 4 Each independently represents S or O.
Compared with the prior art, the polycarboxylic aldehyde compound and the salt thereof provided by the first aspect of the invention have the following beneficial effects: the conventional polycarboxylic aldehyde compound used as the non-ironing finishing agent simultaneously contains hydroxyl and aldehyde groups, acetal or hemiacetal is formed between molecules and cross-linking agent molecules, and the cross-linking effect of the polycarboxylic aldehyde compound and fabrics is reduced. The polybasic carboxylic aldehyde compound of the invention can be used as a non-ironing finishing agent, so that the problem can be avoided, and the structure of the compound can be more effectively crosslinked with protein on fabrics, particularly silk. The DP grade of the finished silk fabric is still more than or equal to 3.5 after 50 times of washing, the whiteness is reduced within 10 degrees, the breaking strength retention rate is more than or equal to 80 percent, the tearing strength increase rate is more than or equal to 100 percent, and the formaldehyde emission is 0.
Preferably, the polycarboxylic aldehyde compound is a sucrose-based polycarboxylic aldehyde compound.
Preferably, the salt comprises an inorganic salt or an organic salt.
Preferably, the inorganic salt comprises a metal salt or an ammonia salt; further preferably, the metal salt includes sodium salt, potassium salt, magnesium salt, calcium salt, barium salt, aluminum salt, iron salt, zinc salt, copper salt or silver salt.
Preferably, the organic salt includes a primary amine salt, a secondary amine salt, a tertiary amine salt, a quaternary ammonium salt, an imidazoline salt, or an imidazolium salt.
Preferably, the structural formula of the polycarboxylic aldehyde compound is shown in the specification
A second aspect of the present invention provides a method for preparing a polycarboxylic aldehyde compound, the method comprising the steps of:
(1) mixing sucrose and a first oxidant to obtain a reaction solution, carrying out a first reaction in an atmosphere of protective gas, and then terminating the reaction to obtain saccharonic acid;
(2) and (2) adding a second oxidant into the sucrose acid obtained in the step (1), and carrying out a second reaction in an atmosphere of protective gas to obtain the polycarboxylic aldehyde compound.
Preferably, the preparation method further comprises a step (3): adding sulfite to the polycarboxylic aldehyde compound obtained in the step (2) to neutralize periodate and iodate.
Preferably, in the reaction solution of step (1), the mass fraction of sucrose is 8-10%.
Preferably, in step (1), the first oxidizing agent is hydrogen peroxide.
Preferably, the hydrogen peroxide is present in the form of hydrogen peroxide.
Preferably, in the hydrogen peroxide, the mass fraction of the hydrogen peroxide is 25-35%; more preferably, the mass fraction of hydrogen peroxide is 30%.
Preferably, in the step (1), the molar ratio of the sucrose to the first oxidant is 1: (3-35); further preferably, the molar ratio of the sucrose to the first oxidant is 1: (25-35); still further preferably, the molar ratio of the sucrose to the first oxidant is 1: 30.
preferably, in the step (1), the protective gas includes at least one of nitrogen, carbon dioxide, helium, neon, argon, krypton and xenon; further preferably, the protective gas is nitrogen.
Preferably, in the step (1), the reaction temperature of the first reaction is 50-90 ℃ and the reaction time is 12-24 h.
Preferably, in the step (1), the reaction temperature of the termination reaction is 15-40 ℃, and the reaction time is 2-6 h; further preferably, the reaction temperature of the termination reaction is 25 to 35 ℃.
Preferably, in the step (1), the terminating reaction comprises the following specific steps: the termination reaction was performed by adding catalase.
Preferably, in step (2), the second oxidant is periodate.
Preferably, the periodate salt comprises at least one of sodium periodate or potassium periodate; further preferably, the periodate is sodium periodate.
Preferably, in the step (2), the molar ratio of the sucrose acid to the second oxidant is 1: (1-10); further preferably, the molar ratio of the saccharonic acid to the second oxidizing agent is 1: (3-4); still further preferably, the molar ratio of said saccharonic acid to said second oxidizing agent is 1: 3.5.
preferably, in the step (2), the protective gas comprises at least one of nitrogen, carbon dioxide, helium, neon, argon, krypton and xenon; further preferably, the protective gas is nitrogen.
Preferably, in the step (2), the reaction temperature of the second reaction is 15-40 ℃, and the reaction time is 12-24 h; further preferably, the reaction temperature of the second reaction is 25 to 35 ℃.
Preferably, in step (3), the sulfite comprises sodium sulfite.
Preferably, in the step (3), the addition amount of the sulfite is judged by the discoloration condition of a starch potassium iodide test paper.
Preferably, in the step (3), the molar ratio of the second oxidant to the sulfite is 1: (1-10); further preferably, the molar ratio of the second oxidant to the sulfite is 1: (3-5); still more preferably, the molar ratio of the second oxidant to the sulfite is 1: 4; starch potassium iodide paper did not turn blue.
A third aspect of the present invention provides a non-ironing finish containing the polycarboxylic aldehyde compound and/or a salt thereof.
The fourth aspect of the invention provides a non-ironing finishing method, which comprises a step of resin shaping, wherein the non-ironing finishing agent is used in the resin shaping process.
Preferably, the non-ironing finishing method comprises a non-ironing finishing method of the fabric.
Preferably, the fabric comprises silk fabric.
Preferably, the easy-care finishing method further comprises at least one step of pre-shaping, rolling and stacking, resin baking, water washing and post-shaping.
Preferably, the sequence of the steps of the easy care finishing method is pre-shaping, resin shaping, rolling and stacking, resin baking, water washing and post-shaping.
Preferably, in the pre-shaping step, the liquid carrying amount is 50-70%, the temperature is 60-80 ℃, and the time is 30-60 seconds.
Preferably, a polyethylene softening agent and a pH value regulator are used in the pre-shaping process; further preferably, the polyethylene softener comprises NP-825, and the pH regulator comprises acetic acid.
Preferably, the concentration or the dosage of the polyethylene softener in the pre-setting process is 10-30 g/L; further preferably, the concentration or the dosage of the polyethylene softening agent is 15-25 g/L; still more preferably, the concentration or amount of the polyethylene softener is 20 g/L.
Preferably, in the presetting process, the concentration or the dosage of the pH value regulator is 0.1-1 g/L; further preferably, the concentration or the dosage of the pH value regulator is 0.4-0.6 g/L; still more preferably, the concentration or amount of the pH regulator is 0.5 g/L.
Preferably, in the step of resin setting, the liquid carrying amount is 50-70%, the temperature is 60-80 ℃, and the time is 30-60 seconds.
Preferably, at least one of a catalyst, a penetrating agent, a fluorescent whitening agent and a silicone softening agent is also used in the process of setting the resin; further preferably, the catalyst comprises sodium hypophosphite monohydrate, the penetrant comprises FKS, the fluorescent whitening agent comprises MST-B, and the silicone-based softener comprises XQS-8.
Preferably, in the process of resin setting, the concentration or the using amount of the easy-care finishing agent is 1-200 g/L; further preferably, the concentration or the dosage of the non-ironing finishing agent is 50-150 g/L.
Preferably, in the process of resin shaping, the concentration or the using amount of the catalyst is 5-50% of the mass of the non-ironing finishing agent; further preferably, the concentration or the dosage of the catalyst is 10-20% of the mass of the non-ironing finishing agent.
Preferably, in the process of setting the resin, the concentration or the dosage of the penetrating agent is 0.5-5 g/L; further preferably, the concentration or dosage of the penetrant is 1-2 g/L.
Preferably, the concentration or the dosage of the fluorescent whitening agent is 1-20g/L in the process of setting the resin; further preferably, the concentration or amount of the fluorescent whitening agent is 5-10 g/L.
Preferably, in the process of setting the resin, the concentration or the dosage of the organosilicon softener is 1-60 g/L; more preferably, the concentration or the dosage of the organosilicon softening agent is 1-30 g/L.
Preferably, the rolling and stacking temperature is 20-40 ℃, and the humidity is as follows: 60-80% for 30min-6 h.
Preferably, the baking temperature of the resin is 120-150 ℃, and the baking time is 3-5 min.
Preferably, the temperature in the step of washing with water is 30-40 ℃ and the time is 3-5 min.
Preferably, at least one of a pH value regulator and an osmotic agent is used in the water washing process; further preferably, the pH adjusting agent comprises acetic acid and the osmotic agent comprises WET.
Preferably, in the water washing process, the concentration or the dosage of the pH value regulator is 0.1-0.5 g/L; further preferably, the concentration or the dosage of the pH value regulator is 0.1 g/L.
Preferably, in the water washing process, the concentration or the dosage of the penetrating agent is 0.1-1 g/L; further preferably, the concentration or dosage of the penetrant is 0.5 g/L.
Preferably, in the step of post-shaping, the liquid carrying amount is 50-70%, the temperature is 60-80 ℃, and the time is 30-60 seconds.
Preferably, at least one of a polyethylene softener, a silicone softener and a pH value regulator is used in the post-sizing process; further preferably, the polyethylene softener comprises NP-825, the silicone softener comprises XQS-1, and the pH regulator comprises acetic acid.
Preferably, in the post-setting process, the concentration or the dosage of the polyethylene softening agent is 10-50 g/L; further preferably, the concentration or the dosage of the polyethylene softening agent is 15-25 g/L; the concentration or the dosage of the polyethylene softening agent is 20 g/L.
Preferably, in the post-setting process, the concentration or the dosage of the organosilicon softener is 10-50 g/L; further preferably, the concentration or the dosage of the organosilicon softener is 25-35 g/L; still more preferably, the concentration or amount of the silicone softener is 30 g/L.
Preferably, in the post-setting process, the concentration or the dosage of the pH value regulator is 0.1-1 g/L; further preferably, the concentration or the dosage of the pH value regulator is 0.4-0.6 g/L; still more preferably, the concentration or amount of the pH regulator is 0.5 g/L.
In a fifth aspect, the invention provides a dyeing method, which comprises the steps of carrying out non-ironing finishing on the fabric by using the non-ironing finishing method, and then carrying out dye dyeing.
The molecular structure of a cross-linking agent used in the traditional non-ironing finishing, such as N-hydroxymethyl resin or a reported polycarboxylic acid or aldehyde cross-linking agent, is small, so that the swelling performance of the non-ironing fabric is also reduced, most of the dye adsorbed on the fabric and the fiber are adsorbed by a polymolecular layer, and the dye is easily washed by household washing conditions.
Although the molecular size of the multi-carboxyl aldehyde compound (cross-linking agent) provided by the invention is larger than that of the traditional cross-linking agent, the swelling of the fabric can be reduced compared with that of the silk fabric without ironing, but the swelling of the fabric can not be greatly reduced (the swelling of the fabric can be greatly reduced by the traditional ironing-free finishing cross-linking agent) because the sucrose is connected by glycosidic bonds based on the sucrose in the disaccharide and the glycosidic bonds increase the activity space of the cross-linking agent molecules, so that the silk fabric after the cross-linking agent is ironed can still be dyed with deep color.
Preferably, the dyeing method comprises a method of dyeing a fabric.
Preferably, the fabric comprises silk.
Preferably, the dyeing method comprises the steps of: presetting, resin setting, rolling and stacking, resin baking, water washing process and dye dyeing.
Preferably, the dyeing method comprises the steps of presetting, resin setting, rolling and stacking, resin baking, water washing process and dye dyeing.
Preferably, the dyeing step of the dye is as follows: dyeing by using a dye bath containing a weakly acidic dye; further preferably, the dyeing step is as follows: firstly, putting the fabric into a dyeing bath containing a weakly acidic dye at normal temperature (25-30 ℃) for dyeing for 15-25min, wherein the bath ratio is 1: (15-25), heating to 85-95 ℃ at the speed of 2.5-3.5 ℃/min, preserving heat for 25-35min, and washing with water at the temperature of 35-45 ℃ for 10min after dyeing.
Preferably, the weakly acidic dye includes an acidic 80 series dye; further preferably, the acid 80 series dye includes at least one of acid blue 80, acid green 80 and acid red 80.
Preferably, in the step of dyeing with the dye, the concentration or dosage of the weakly acidic dye is 1-10% owf; further preferably, the concentration or dosage of the weakly acidic dye is 1-3% owf; still further preferably, the concentration or amount of the weakly acidic dye is 2% owf.
Preferably, the pH value of the dye bath is 3-5.
In a sixth aspect, the present invention provides a fabric processed using the above-described easy-care finishing method or the above-described dyeing method.
The preferable fabric is silk fabric, DP grade is more than or equal to 3.5 after 50 times of washing (the DP grade is maximum 5 grade), whiteness is reduced by less than 10 degrees, breaking strength retention rate is more than or equal to 80 percent, tearing strength lifting rate is more than or equal to 100 percent, and formaldehyde release amount is 0.
A seventh aspect of the invention provides a garment made from the above fabric, or made by the above easy care finishing method or the above dyeing method.
Compared with the prior art, the invention has the following beneficial effects:
(1) the conventional non-ironing finishing agent containing the multi-carboxyl aldehyde compound simultaneously contains hydroxyl and aldehyde groups, acetal or hemiacetal can be formed in molecules and among cross-linking agent molecules, and the cross-linking effect of the non-ironing finishing agent and fabrics is reduced. The polybasic carboxylic aldehyde compound of the invention can be used as a non-ironing finishing agent, so that the problem can be avoided, and the structure of the compound can be more effectively crosslinked with protein on fabrics, particularly silk.
(2) Sucrose-based multi-carboxylic aldehyde easy-care finishing agent: the invention is based on sucrose with three primary hydroxyl groups, and utilizes the synergistic oxidation effect of two different oxidants of hydrogen peroxide and periodate to prepare the multi-carboxyl aldehyde formaldehyde-free non-ironing finishing agent, and the finishing liquid does not contain residual strong oxidant.
(3) The non-formaldehyde high-whiteness high-easy-care grade silk fabric comprises the following components in percentage by weight: the byproduct formic acid in the preparation of the non-ironing finishing agent and the additionally added sodium hypophosphite monohydrate form a high-efficiency catalyst, and the small-molecular fluorescent whitening agent added in the process is matched with a low-temperature cold reactor to realize the effective permeation of the fluorescent whitening agent and the cross-linking agent. The DP grade of the finished silk fabric is still more than or equal to 3.5 after 50 times of washing, the whiteness is reduced within 10 degrees, the breaking strength retention rate is more than or equal to 80 percent, the tearing strength increase rate is more than or equal to 100 percent, and the formaldehyde emission is 0.
(4) The finishing process can be carried out after ironing: the sucrose-based multi-carboxyl aldehyde easy-care finishing agent can react with primary amino groups in silk and primary hydroxyl groups, and ether bonds which can freely rotate in a certain space exist in the molecular structure of the finishing agent, so that silk fabrics subjected to easy-care finishing can still be dyed. The non-ironing silk fabric dyed by the weak-acid dye can still be dyed with deeper color depth, and various color fastness is not reduced. The problem of large color difference of the net-color silk fabric which is dyed firstly and then finished without ironing in the traditional process is solved.
Drawings
FIG. 1 shows the principle of preparation of a sucrose-based polycarboxylic aldehyde compound;
FIG. 2 is an infrared spectrum of sucrose and a sucrose-based polycarboxylic aldehyde compound of example 1 of the present invention;
FIG. 3 is a NMR spectrum of sucrose;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of sucraldehyde;
FIG. 5 is a NMR spectrum of a sucrose-based polycarboxylic aldehyde compound of example 1 of the present invention;
FIG. 6 shows the mechanism of cross-linking sucrose-based polycarboxylic aldehyde compounds with silk.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are not intended to limit the scope of the claimed invention.
The starting materials, reagents or apparatuses used in the following examples are conventionally commercially available or can be obtained by conventionally known methods, unless otherwise specified.
The test method comprises the following steps:
1. determination of the carboxyl content
0.3g of the lyophilized test substance was weighed and added to a mixed solution of 55mL of deionized water and 5mL (0.01 mol/L) of sodium chloride solution, and the mixture was stirred sufficiently for a while until the solid powder disappeared. Then the pH value of the solution is adjusted to be between 2.5 and 3 by using 0.1mol/L diluted hydrochloric acid. Finally, 0.04mol/L sodium hydroxide solution is used for adjusting the pH value of the solution to about 11 at the speed of 0.1mL/min, and a conductivity meter is used for detecting the conductivity value of the solution in the process. The conductivity value of the solution shows a trend that the conductivity value is rapidly reduced and then rapidly increased after being balanced along with the increase of the usage amount of the sodium hydroxide, wherein the volume of the sodium hydroxide corresponding to the turning point of the reduction to the balance is VAmL, and the volume of the sodium hydroxide corresponding to the turning point of the balance to the rapid increase is VBmL.
The calculation formula of the carboxyl content is as follows:
carboxyl group content (mmol/g) ═ c × (V) B -V A )/m Oxidized sucrose
Wherein c is the concentration of sodium hydroxide and the unit is mol/L; m is Oxidized sucrose The unit is the mass of the sample used, in g.
2. Determination of aldehyde group content
0.1g of the test substance was dissolved in 25mL of a hydroxylamine chloride solution having a concentration of 0.25mol/L, followed by addition of 2 drops of methyl orange indicator. After the color of the solution had no longer changed, titration was carried out using 0.1mol/L sodium hydroxide solution. When the color of the mixed solution changed from red to yellow, the titration was stopped and the volume of the sodium hydroxide solution consumed was read. The content of aldehyde groups in the sucrose-based polycarboxylic aldehyde compound is calculated according to the following formula:
n sodium hydroxide ×V＝n Aldehyde group
Aldehyde group content (mol/g) ═ n Aldehyde group /m Oxidation products
Wherein n is Sodium hydroxide The concentration of sodium hydroxide used for titration is expressed in mol/L; v is the volume of the concentration of sodium hydroxide used for titration, in mL; n is Aldehyde group The unit is the mol of the aldehyde group of the sucrose oxidation product; m is Oxidation products Is the mass of the oxidation product of sucrose in g.
3. Fourier infrared spectrum analysis: the infrared spectrum of the sucrose and sucrose-based polycarboxylic aldehyde compound is 500-4000cm -1 And (5) performing characterization in wave number.
4. Nuclear magnetic hydrogen spectrum analysis: NMR spectra of sucrose and sucrose based polycarboxylic aldehyde compounds were characterized on Bruker AVANCE III HD400 MHZ.
5. The breaking strength, tearing strength, wrinkle recovery angle, washed appearance, formaldehyde release amount and whiteness of the silk fabric are respectively tested according to GB/T3923.2-2013, GB/T3917.1-2009, GB/T3819-1997, GB/T13769-2009, GB/T2912.1-2009 and AATCC 110-2015.
6. Color evaluation of silk fabric: dyed fabrics under standard conditions were tested for color characteristics between the visible wavelength range (400-750nm), including at least one of L, a, b and K/S.
7. The friction resistance, soaping resistance and light fastness evaluation are respectively tested according to methods such as GB/T3920-2008, GB/T3921-2008 and GB/T8427-2019.
Example 1
The non-ironing finishing agent is a sucrose-based multi-carboxyl aldehyde compound with a structural formula
The preparation method of the sucrose-based polycarboxylic aldehyde compound comprises the following steps:
(1) preparation of saccharose acid: mixing 3.42g of sucrose and 30mL of 30 wt% hydrogen peroxide solution to prepare a reaction solution, reacting for 12h at 70 ℃ under the protection of nitrogen, adding 2ul of catalase to terminate the reaction, and reacting for 6h at the normal temperature of 35 ℃ to obtain a sucrose acid solution;
(2) preparation of sucrose-based polycarboxylic aldehyde compound: adding sodium periodate into the sucrose acid solution obtained in the step (1), and reacting for 24 hours at normal temperature under the protection of nitrogen to obtain the sucrose-based multi-carboxyl aldehyde compound, wherein the molar ratio of sucrose acid to sodium periodate is 1: 3.5.
(3) and (3) removing the oxidant: adding excessive sodium sulfite to the sucrose polycarboxylic aldehyde compound obtained in the step (2) to neutralize residual periodate and iodate, judging the adding amount of the sodium sulfite according to the discoloration condition of a starch potassium iodide test paper, wherein the molar ratio of sodium periodate to sodium sulfite is about 1: 3.5, obtaining the sucrose-based multi-carboxyl aldehyde compound which does not contain oxidant and does not contain formaldehyde, namely the non-ironing finishing agent, and storing the compound in a low-temperature refrigerator.
FIG. 1 shows the principle of preparation of a sucrose-based polycarboxylic aldehyde compound; first passing hydrogen peroxide (H) 2 O 2 ) Oxidizing primary alcohol on sucrose into carboxyl to generate saccharonic acid, and then passing through sodium periodate (NaIO) 4 ) Oxidation of sucrose acids produced the sucrose-based polycarboxylic aldehyde compound of example 1.
FIG. 2 is an infrared spectrum of sucrose and a sucrose-based polycarboxylic aldehyde compound of example 1 of the present invention, with the wave number on the abscissa in cm -1 The ordinate is intensity; 1603cm in FIG. 2 -1 Is carbonyl peak of aldehyde group in sucrose-based polycarboxylic aldehyde compound, 1718cm -1 Is the carbonyl peak of the carboxyl group in the sucrose-based polycarboxylic aldehyde compound.
FIG. 3 is a NMR spectrum of sucrose in ppm on the abscissa f1 (chemical shift). FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of sucrose aldehyde with abscissa f1 in ppm; from FIG. 4, it can be found that there is a characteristic peak of aldehyde group (-CHO) at 8.5 ppm.
FIG. 5 is a NMR spectrum of a sucrose-based polycarboxylic aldehyde compound of example 1 of the present invention with abscissa f1 in ppm; from the nuclear magnetic hydrogen spectrum of FIG. 5, characteristic peaks corresponding to an aldehyde group (-CHO) and a carboxyl group (-COOH) in the vicinity of 8.4ppm and 9.5ppm, respectively, were found. The sucrose-based multi-carboxyl aldehyde compound prepared by the implementation method has the carboxyl content of 8.2mmol/g, the aldehyde group content of 11.1mmol/g, and the carboxyl content: the aldehyde group content was 3:4.061, and the compound was found to be
(carboxy: aldehyde group: 3: 4). The content analysis of carboxyl and aldehyde groups is combined to obtain that the yield of the carboxyl and the aldehyde groups is close to 95 percent, which indicates that the preparation of the formaldehyde-free sucrose-based multi-element carboxyl aldehyde compound, namely the non-ironing finishing agent, is more successful.
Example 2
A high-whiteness silk non-ironing silk fabric and a non-ironing finishing method thereof are disclosed, wherein the non-ironing finishing method comprises the following steps:
the silk fabric I is processed according to the steps of pre-shaping, resin shaping, rolling and stacking, resin baking, washing and post-shaping to obtain the silk non-ironing silk fabric with high whiteness, wherein the liquid carrying capacity of the fabric in the pre-shaping, resin shaping and post-shaping processes is 70%, the temperature is 80 ℃, and the time is 45 seconds.
The formula used in the process of pre-setting is as follows: 20g/L of polyethylene softening agent NP-825 and 0.5g/LpH value regulator acetic acid.
The formula used in the resin shaping process is as follows: 100g/L of the easy care finish (sucrose-based polycarboxylic aldehyde compound) of example 1, 10g/L of sodium hypophosphite monohydrate, 1g/L of the penetrating agent FKS, 5g/L of the fluorescent whitening agent MST-B, and 10g/L of the silicone softener XQS-8.
The temperature of the rolling and stacking is 35 ℃, and the humidity is as follows: 65% for 2 h.
The resin baking temperature is 150 deg.C, and the time is 5 min.
The formula used in the washing process is as follows: 0.1g/L acetic acid, 0.5g/L penetrating agent WET, and the temperature of water washing is 30 ℃ and the time is 3 min.
The formula used in the process of post-forming is as follows: 20g/L of polyethylene softener NP-825, 30g/L of silicon softener XQS-1 and 0.5g/L of pH value regulator acetic acid.
The permanent press effect data of example 2 is shown in table 1 below.
In the present invention, it is known that the breaking strength of silk fabric i without any treatment is 374N, the dry state wrinkle recovery angle is 253 °, the wet state wrinkle recovery angle is 212 °, the whiteness is 155 °, the formaldehyde content is 0, the cloth surface flatness is 1.8 grade, and the washing size change rate is ± 9%.
Example 3
A high-whiteness silk non-ironing silk fabric and a non-ironing finishing method thereof are disclosed in embodiment 3, which is different from embodiment 2 in that: the resin baking temperature is 120 deg.C, and the time is 3 min.
The permanent press effect data for example 3 is shown in table 1 below.
Comparative example 1
A non-ironing finishing agent is a sucrose-based polyaldehyde compound, and a preparation method of the sucrose-based polyaldehyde compound comprises the following steps: dissolving 3.42g of sucrose in 30mL of distilled water, adding 7.5g of sodium periodate, carrying out ultrasonic microwave assisted dissolution, reacting for 24h at normal temperature under the protection of nitrogen, adding excess barium chloride, stirring for 1h at 5 ℃, and filtering to obtain a sucrose-based polyaldehyde compound, namely the non-ironing finishing agent.
Comparative example 2
A non-ironing silk fabric and a non-ironing finishing method thereof are disclosed, wherein the comparative example 2 is different from the example 2 in that: the "easy care finish (sucrose-based polyaldehyde compound) in comparative example 1 was used to replace the" easy care finish in example 1 "in the resin-styling formulation.
The permanent press effect data of comparative example 2 are shown in table 1 below.
Comparative example 3
A non-ironing silk fabric and a non-ironing finishing method thereof, wherein the difference between a comparative example 3 and an example 2 is as follows: "100 g/L of the permanent press finish of example 1" in the resin styling formulation was replaced with "100 g/L of 1,2,3, 4-butanetetracarboxylic acid (BTCA)".
The permanent press effect data of comparative example 3 are shown in table 1 below.
Comparative example 4
Comparative example 4 is silk fabric i without any treatment.
The permanent press effect data of comparative example 4 are shown in table 1 below.
TABLE 1 comparison of No-iron Effect of example 2, example 3 and comparative examples 2 to 4
Table 1 shows the comparison of the permanent press effect of example 2, example 3 and comparative examples 2 to 4. The DP grade of the silk fabrics finished in the embodiments 2 and 3 is still more than 3.5 after 50 times of washing, the whiteness is reduced within 10 degrees, the breaking strength retention rate is more than 95%, the tearing strength promotion rate is more than 100%, and the formaldehyde release amount is 0. In the embodiments 2 and 3 of the invention, a high-efficiency catalyst is formed by utilizing the by-product formic acid in the preparation of the non-ironing finishing agent and additionally added sodium hypophosphite monohydrate, and the small-molecular fluorescent whitening agent added in the formula is matched with a low-temperature cold stack to realize the effective permeation of the fluorescent whitening agent and the cross-linking agent.
The conventional easy-care finishing agent containing the multi-carboxyl aldehyde compound simultaneously contains hydroxyl and aldehyde groups, and acetal or hemiacetal can be formed in molecules and among cross-linking agent molecules, so that the cross-linking effect of the easy-care finishing agent and fabrics is reduced; the multi-carboxylic aldehyde compound of the invention can be used as a non-ironing finishing agent, which can avoid the problem (the cross-linking agent does not contain hydroxyl, and acetal or hemiacetal can not be formed in the molecule and between the molecules of the cross-linking agent), and the structure of the sucrose-based multi-carboxylic aldehyde compound of the invention can be more effectively cross-linked with protein on fabrics, especially silk.
FIG. 6 is a cross-linking mechanism of sucrose-based polycarboxylic aldehyde compounds with silk; two possible crosslinking mechanisms are shown in FIG. 6, which are highly effective with the by-product formic acid from the preparation of the permanent press finish and the additional addition of sodium hypophosphite monohydrateCatalyst for the preparation of polycarboxylic aldehyde compounds
Catalytically cross-linked with proteins (proteins) on silk. The sucrose-based polycarboxylic aldehyde compound and the protein cross-linking agent specifically comprise: 1. the aldehyde group participates in an acetal reaction or an aminal reduction reaction to be combined with units such as tryptophan, arginine and the like on the protein, and the expressed form is
2. Hypophosphorous acid is used as a catalyst, carboxyl is combined with protein, and the form is
In addition, the carboxylic acid in the sucrose polycarboxylic aldehyde compound can form an ionic bond with amino groups in the protein in the form of
Example 4
The embodiment 4 is different from the embodiment 2 in that: the silk fabric I is replaced by the silk fabric II, and the fluorescent whitening agent MST-B is not contained in the formula for resin shaping.
In the present invention, it is known that the breaking strength 362N, the dry state wrinkle recovery angle 248 °, the wet state wrinkle recovery angle 206 °, the whiteness 73 °, the fabric surface flatness 1.7 grade, and the washing size change rate ± 10% of the silk fabric ii (white silk fabric) without any treatment.
The permanent press effect data for example 4 is shown in table 2 below.
Example 5
A dyed non-ironing silk fabric and a preparation method thereof (dyeing after non-ironing):
(1) the unbleached permanent press silk fabric of example 4 was placed in a dye bath containing a weakly acidic dye for dyeing, the concentration of acid blue 80 was 2% owf, the bath ratio was 1: 20, dyeing at normal temperature for 20min, heating to 90 ℃ at a speed of 3 ℃/min, and keeping the temperature for 30min, wherein the pH value of the dyeing bath is 3. And after dyeing is finished, washing for 10min at 40 ℃, and airing at normal temperature to obtain a semi-finished fabric.
(2) And carrying out post-shaping processing on the semi-finished fabric to obtain the dyed non-ironing silk fabric. The formula of the post-forming is as follows: 20g/L of polyethylene softener NP-825, 30g/L of silicon softener XQS-1 and 0.5g/L of pH value regulator acetic acid; the liquid carrying capacity of the fabric in the post-sizing process is 70 percent, the temperature is 80 ℃, and the time is 45 seconds.
The easy care effect data of example 5 are shown in table 2 below, and the color evaluation and color fastness data are shown in table 3 below.
Comparative example 5
The white non-ironing silk fabric and the non-ironing finishing method (BTCA non-ironing treatment) thereof are different from the comparative example 5 in that: the silk fabric I is replaced by the silk fabric II, and the fluorescent whitening agent MST-B is not contained in the formula for resin shaping.
Comparative example 6
A dyed silk fabric and a method of making the same (direct dyeing without permanent press treatment), comparative example 6 differs from example 5 in that: "the unbleached permanent press silk fabric of example 4" in example 5 was replaced with "silk fabric ii".
The easy care effect data of comparative example 6 are shown in table 2 below, and the color evaluation and color fastness data are shown in table 3 below.
Comparative example 7
A dyed silk fabric and method of making the same (BTCA easy care followed by dyeing), comparative example 7 differs from example 5 in that: the "unbleached permanent press silk fabric of example 4" in example 5 was replaced with the "unbleached permanent press silk fabric of example 5" in comparative example 5.
The easy care effect data of comparative example 7 are shown in table 2 below, and the color evaluation and color fastness data are shown in table 3 below.
TABLE 2 comparison of the permanent press effect of example 4, example 5, comparative example 6 and comparative example 7
TABLE 3 color evaluation, color fastness comparison of example 5, comparative example 6 and comparative example 7
Table 2 shows the comparison of the permanent press effect of example 4, example 5, comparative example 6 and comparative example 7; table 3 shows color evaluation and color fastness comparison of example 5, comparative example 6 and comparative example 7. The sucrose-based multi-carboxyl aldehyde easy-care finishing agent in the embodiment 5 can react with primary amino groups in silk and can also react with primary hydroxyl groups, and ether bonds which can freely rotate relatively in a certain space exist in the molecular structure of the finishing agent, so that silk fabrics subjected to easy-care finishing can still be dyed; the non-ironing silk fabric dyed by the weakly acidic acid dye can still be dyed with deeper color depth, and various color fastness is not reduced. The problem of big colour difference that net look silk fabric dyed earlier then the non-ironing finish or dyeing after the non-ironing finish in traditional technology is solved.
Claims (10)
1. The multi-carboxyl aldehyde compound and the salt thereof are characterized in that the structural general formula of the multi-carboxyl aldehyde compound is
R 1 ＝O，R 2 、R 3 、R 4 Each independently represents S or O.
2. The polycarboxylic aldehyde compound and the salt thereof according to claim 1, wherein the polycarboxylic aldehyde compound has the structure of
3. The polycarboxylic aldehyde compound according to claim 1, and salts thereof, comprising inorganic or organic salts; the inorganic salt comprises a metal salt or an ammonia salt; the organic salt comprises primary amine salt, secondary amine salt, tertiary amine salt, quaternary ammonium salt, imidazoline salt or imidazole.
4. A method for preparing the polycarboxylic aldehyde compound according to any one of claims 1 to 3, comprising the steps of:
(1) mixing sucrose and a first oxidant to obtain a reaction solution, carrying out a first reaction in an atmosphere of protective gas, and then terminating the reaction to obtain saccharonic acid;
(2) and (2) adding a second oxidant into the sucrose acid obtained in the step (1), and carrying out a second reaction in an atmosphere of protective gas to obtain the polycarboxylic aldehyde compound.
5. A permanent press finishing agent characterized in that the permanent press finishing agent contains the polycarboxylic aldehyde compound and/or the salt thereof according to any one of claims 1 to 3.
6. A non-ironing finishing method, characterized in that the non-ironing finishing method comprises a resin shaping step, and the non-ironing finishing agent in claim 5 is used in the resin shaping process.
7. A non-ironing finishing method according to claim 6, characterized in that the non-ironing finishing method further comprises at least one of the steps of pre-setting, rolling and stacking, resin baking, water washing and post-setting.
8. A dyeing process comprising a permanent press finish using the permanent press finishing process of any one of claims 6 to 7 followed by dye dyeing.
9. A fabric produced using the easy care finishing method of any one of claims 6 to 7 or the dyeing method of claim 8.
10. A garment formed using the fabric of claim 9 or by the permanent press finishing method of any one of claims 6 to 7 or the dyeing method of claim 8.
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|---|---|---|---|---|
| US4820307A (en) * | 1988-06-16 | 1989-04-11 | The United States Of America As Represented By The Secretary Of Agriculture | Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids |
| CN111690072A (en) * | 2020-06-05 | 2020-09-22 | 江南大学 | Preparation and application of polyaldehyde anti-crease finishing agent for cotton fabric |
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| US4820307A (en) * | 1988-06-16 | 1989-04-11 | The United States Of America As Represented By The Secretary Of Agriculture | Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids |
| CN111690072A (en) * | 2020-06-05 | 2020-09-22 | 江南大学 | Preparation and application of polyaldehyde anti-crease finishing agent for cotton fabric |
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