CN104195822A - Method using acryloyl succinic acid in cotton fabric formaldehyde-free crease resistant finishing - Google Patents
Method using acryloyl succinic acid in cotton fabric formaldehyde-free crease resistant finishing Download PDFInfo
- Publication number
- CN104195822A CN104195822A CN201410323479.2A CN201410323479A CN104195822A CN 104195822 A CN104195822 A CN 104195822A CN 201410323479 A CN201410323479 A CN 201410323479A CN 104195822 A CN104195822 A CN 104195822A
- Authority
- CN
- China
- Prior art keywords
- acryloyl
- butanedioic acid
- cotton fabric
- acid monomer
- free formaldehyde
- 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
- 239000004744 fabric Substances 0.000 title claims abstract description 74
- 229920000742 Cotton Polymers 0.000 title claims abstract description 51
- TYQAAGLICKBDSM-UHFFFAOYSA-N 2-prop-2-enoylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)C(=O)C=C TYQAAGLICKBDSM-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 80
- -1 acryloyl aspartic acid Chemical compound 0.000 claims description 30
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 24
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 19
- 239000001630 malic acid Substances 0.000 claims description 19
- 235000011090 malic acid Nutrition 0.000 claims description 19
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229960005137 succinic acid Drugs 0.000 claims description 12
- 235000003704 aspartic acid Nutrition 0.000 claims description 11
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000001488 sodium phosphate Substances 0.000 claims description 10
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 10
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 6
- AZUVALGXHZSYBD-UHFFFAOYSA-N 2,3-dihydroxy-2-prop-2-enoylbutanedioic acid Chemical compound C(=O)(C=C)C(C(=O)O)(O)C(O)C(=O)O AZUVALGXHZSYBD-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 6
- ZCHSJFKCKMVVNC-UHFFFAOYSA-N C(C=C)(=O)C(C(=O)O)(CC(=O)O)S Chemical compound C(C=C)(=O)C(C(=O)O)(CC(=O)O)S ZCHSJFKCKMVVNC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 239000003223 protective agent Substances 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 235000019394 potassium persulphate Nutrition 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 230000000694 effects Effects 0.000 abstract description 15
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 description 19
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 14
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000001153 anti-wrinkle effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000002689 maleic acids Chemical class 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000746 allylic group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006392 deoxygenation reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- FJWSGQDJVJXMIK-UHFFFAOYSA-N 2-(2-methylprop-2-enoyl)butanedioic acid Chemical compound C(=O)(C(=C)C)C(C(=O)O)CC(=O)O FJWSGQDJVJXMIK-UHFFFAOYSA-N 0.000 description 2
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 206010016590 Fibrin deposition on lens postoperative Diseases 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 0 CCC(C(OCC([C@](C(C)O)*([C@]1OC(CO)[C@](C[C@@](*C(*)[C@@](C2CC)OC**)C2O)C(*)C1O)=C)C(C1O)C1(C*)C=C)=O)OC(C=C)=O Chemical compound CCC(C(OCC([C@](C(C)O)*([C@]1OC(CO)[C@](C[C@@](*C(*)[C@@](C2CC)OC**)C2O)C(*)C1O)=C)C(C1O)C1(C*)C=C)=O)OC(C=C)=O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- PXGRHRPMYBEJAT-UHFFFAOYSA-N [C].C(C=C)(=O)C(C(=O)O)CC(=O)O Chemical compound [C].C(C=C)(=O)C(C(=O)O)CC(=O)O PXGRHRPMYBEJAT-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- PPBYBJMAAYETEG-UHFFFAOYSA-N ethene;formaldehyde;urea Chemical group C=C.O=C.NC(N)=O PPBYBJMAAYETEG-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a method using acryloyl succinic acid in cotton fabric formaldehyde-free crease resistant finishing, and in particular relates to a method as follows: higher activity allyl is introduced into a dicarboxyl containing structure, a series of acryloyl succinic acid monomers are designed and synthesized by a simple method, and then used in cotton fabric crease resistant finishing. Raw materials for reaction for synthesis and design of the compounds are cheap and easily obtained, the reaction is simple to operate and easy to control; the reaction is mild in condition, and environmentally friendly, and the production cost is low. The series of synthesized acryloyl succinic acid monomers are used in cotton fabric crease resistant finishing for realizing cotton fabric formaldehyde-free crease resistant finishing, and cotton fabrics finished by the acryloyl succinic acid product have good crease resistant properties, whiteness and good strength maintainence.
Description
Technical field
The invention belongs to Textile Chemistry and Dyeing and Finishing Engineering technical field, relate to acryloyl butanedioic acid for the method for COTTON FABRIC free formaldehyde DP finish.
Background technology
COTTON FABRIC has many good wearability, as has softness, comfortable, ventilative, good hygroscopicity, and the advantages such as fabulous wearability and low price make it enjoy people to favor.But COTTON FABRIC in dress and washing process easily wrinkling, can not keep smooth outward appearance, need to often press, therefore the life to people brings inconvenience.For overcoming cotton clothes wrinkling defect in wearing process, need to carry out anti-crease finishing to COTTON FABRIC.
In dyeing and finishing industry, the finishing agent for cotton fabric crease-shedding is mainly N-methylol amide class finishing agent at present, and wherein extensive use is ethylene urea-formaldehyde resin, also claims 2D resin.As far back as last century the forties just for cotton fabric crease-shedding, arrange and use till today always, after 2D RESIN FINISH, fabric has good wrinkle resistance, good surface smoothness and wash durability.But 2D resin disadvantage is to be contained in methylol in structure, in process and after arranging on fabric, there is formaldehyde release And Spread of Solute, be detrimental to health.Although the burst size of methanal of etherified 2D resin significantly reduces, still fail fundamentally to solve formaldehyde and discharge this problem.Along with people are more and more higher to the requirement of green living, exploitation formaldehydeless finishing agent is extremely urgent.
Research about free formaldehyde DP finish agent has a lot, but generally acknowledge at present there is most prospects for commercial application surely belong to polybasic carboxylic acid class finishing agent.The people such as Welch in 1988 have reported and have used polybasic carboxylic acid and supporting catalyst inferior sodium phosphate for the anti-crease finishing of COTTON FABRIC, and anti-wrinkle effect is obvious, has realized free formaldehyde DP finish.The people such as Charles Q.Yang have compared 17 kinds of polybasic carboxylic acids by infrared spectrum analysis and have been applied to after DP finish of cotton fabric difference on effect find, best with butanetetra-carboxylic acid (BTCA) effect, the effect of citric acid (CA) and poly (PMA) is also better.But the problem existing is that BTCA is expensive, and production cost is higher, and after arranging, fabric strength declines obvious etc.; Though effect is good, still there is fabric yellowing problems in citric acid (CA); Poly (PMA) is although finishing effect is pretty good, and price also has competitiveness with 2D resin, and is difficult for synthetic; Because itself is difficult to autohemagglutination maleic acid, the degree of polymerization is not easy to control, and be difficult to obtain good finishing effect, and poly arrangement product look no-load voltage ratio is more serious, affects the quality of fabric.
The people such as Choi will be containing two key unsaturated carboxylic acid maleic acids (MA) and itaconic acid (ITA) anti-crease finishing for COTTON FABRIC, research finds that MA or ITA are under the effect of radical initiator and ester crosslinking catalyst, can give fabric crease-resistant performance, after arranging, Different Tear Test brute force and wear resistance are better than 2D resin.MA and ITA and fibrin reaction mechanism of crosslinking are as follows:
Because maleic acid MA and itaconic acid ITA are difficult for polymerization on fabric, its crease-resistant cross-linking effect is had a greatly reduced quality.And fabric exists yellowing problems after arranging, if adopt in-situ polymerization technique, this phenomenon is particularly evident, and strength damage is serious.Due to maleic acid MA and itaconic acid ITA cheap and easy to get, therefore how it is carried out to modification and improves cloth cover quality, significant to formaldehydeless noniron finish.
Traditional unsaturated carboxylic acid, for the research of anti-crease finishing, is all finishing technique and the mechanism of crosslinking research that concentrates on maleic acid and itaconic acid.About the existing relevant report of acryloyl butanedioic acid, the people such as Rubing Cai in 1999 utilize acrylic anhydride to react with malic acid, synthesize and prepare acryloyl malic acid, and introduced it and as interpolation monomer, prepared the method for polymer, application United States Patent (USP); The people such as Dong Xie in 2003 have reported and have utilized acryloyl chloride and asparagine acid reaction synthesizing propylene acyl aspartic acid, have introduced it and have prepared polymer method as adding monomer, and its polymer is for tooth filling; At Kakino in 2011, the people such as Ryuki utilized acryloyl chloride to react with malic acid, painted and apply for a patent for ink; Oh in 2014, the people such as Sang Min apply for a patent, and acryloyl chloride reacts with malic acid, for photosensitive colour-changing polymer monomer additive and apply for a patent.
Yet, with acryloyl chloride, react with tartaric acid, mercapto succinic acid, there is no bibliographical information.In addition the anti-crease finishing that acryloyl butanedioic acid is used for to COTTON FABRIC there is no bibliographical information.
Summary of the invention
Technical problem to be solved by this invention is to provide acryloyl butanedioic acid for the method for COTTON FABRIC free formaldehyde DP finish, solves the problems such as traditional unsaturated carboxylic acid finish fabric yellowing, brute force is low, polymerization effect is not good.
Acryloyl butanedioic acid of the present invention, for COTTON FABRIC free formaldehyde DP finish method, comprises the following steps:
(1) preparation of anti-crease finishing liquid;
Anti-crease finishing liquid forms: acryloyl butanedioic acid monomer 0.4～1.0mol/L, catalyst 10～20g/L, strong protecting agent 0～10g/L, softener 0～10g/L;
(2) anti-crease finishing;
Employing is rolled and is cured finishing technique and carry out anti-crease finishing, 80～100 ℃ of preliminary drying temperature, and stoving temperature is controlled at 160～190 ℃;
Described acryloyl butanedioic acid monomer is acryloyl aspartic acid monomer, acryloyl malic acid monomer, acryloyl mercapto butanedioic acid monomer or acryloyl tartaric acid monomer, and structural formula is respectively:
As preferred technical scheme:
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, described acryloyl butanedioic acid monomer synthetic be take acryloyl chloride with containing active hydrogen butanedioic acid, be raw material synthesizing propylene acyl butanedioic acid monomer, its reaction equation is as follows:
Concrete steps are: by acryloyl chloride with containing active hydrogen butanedioic acid be dissolved in reaction dissolvent mutually in; Add thermal response, after reaction finishes; Reactant liquor decompression is spin-dried for, and obtains acryloyl butanedioic acid monomer.
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, and the molar ratio that contains active hydrogen butanedioic acid and acryloyl chloride is 1.0:1.1～2.5.
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, and described is malic acid, tartaric acid, mercapto succinic acid or aspartic acid containing active hydrogen butanedioic acid.
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, and described heating reaction temperature is controlled between 30～80 ℃, and the reaction time is controlled at 6～24h.
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, and synthesizing of described acryloyl butanedioic acid monomer also comprises further purification, i.e. reactant liquor decompression is spin-dried for, and revolves desolventizing layer, obtains the thick product of acryloyl butanedioic acid monomer; Thick product is selected column chromatography for separation, dry method loading, and eluant, eluent is selected ethyl acetate: the volume ratio of benzinum is 1:0.5～2, obtains acryloyl butanedioic acid monomer net product.
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, and described catalyst is one or more in potassium peroxydisulfate, ammonium persulfate, inferior sodium phosphate.
Acryloyl butanedioic acid as above is for COTTON FABRIC free formaldehyde DP finish method, and described employing is rolled and cured finishing technique and refer to that normal temperature pads, and two soak two rolls, pick-up 60～90%, and 80～100 ℃ of prebake 3～10min, 160～190 ℃ are cured 2～4min.
Utilize double bond containing carboxylic acid to arrange for cotton fabric crease-shedding, require:
1) carboxylic acid molecules is little, is easy to enter fibrous inside;
2) carboxylic acid structure can form acid anhydrides and further become ester crosslinked with cellulose hydroxyl reaction under catalyst action;
3) easily there is radical polymerization in two keys under catalyst action;
4) ester is crosslinked is cross-linked on fabric and occurs simultaneously with radical polymerization, at fibrous inside and surface, forms cross-linked network, providing cotton fabric wrinkle resistance.
Containing allylic monomers, be important organic synthesis raw material and synthetic resin monomer, polymerization speed is fast.Can homopolymerization and copolymerization containing allylic monomers, also can with the monomer copolymerization such as acrylonitrile, styrene, butadiene, vinyl chloride and cis-butenedioic anhydride.Its polymer is for the synthesis of aspects such as resin, adhesive, synthetic rubber, synthetic fiber, super absorbent resin, pharmacy, leather, weaving, chemical fibre, building materials, water treatment, oil exploitation, coating; Wherein acrylic acid is one of important source material of water-soluble polymer, can make superpower property water absorbing agent with starch graft copolymer.
In applied chemistry field, containing allylic monomers, be the polymerization single polymerization monomer of commonly using the most.The present invention is high by activity, the allyl of easy polymerization is introduced and contained dicarboxyl structure, synthesizing propylene acyl butanedioic acid monomer.Acryloyl butanedioic acid is monosubstituted alkene structures, compared to two substituted olefine carboxylic acid maleic acid MA and itaconic acid ITA, sterically hindered little, forms free radical activity large, is easy to polymerization; In addition the side chain of the two key links of acryloyl butanedioic acid is long, and after carboxylic acid and fibrin reaction, two key scopes of activities are larger, and reaction can hinder little, is beneficial between two keys radical polymerization occurs.Take acryloyl malic acid as example, and itself and COTTON FABRIC mechanism of crosslinking are as follows:
Beneficial effect
1. in the present invention, first acryloyl butanedioic acid is used for to COTTON FABRIC free formaldehyde DP finish;
2. a series of acryloyl butanedioic acid monomers of design, utilize short-cut method to synthesize and are applied to Cotton Fabric;
3. after Product organization of the present invention, fabric has good wrinkle resistance, whiteness, powerful maintenance well.
Accompanying drawing explanation
Fig. 1 acryloyl butanedioic acid hydrogen spectrum
1h NMR (400MHz, DMSO): 12.61 (s, 2H), 6.38 (dd, J=17.2,1.4H
z, 1H), 6.23 (dd, J=17.3,10.3H
z, 1H), 6.02 (dd, J=10.3,1.3H
z, 1H), 5.29 (dd, J=8.6,3.9H
z, 1H), 2.88 (dd, J=16.7,4.0H
z, 1H), 2.77 (dd, J=16.8,8.7H
z, 1H),
Fig. 2 acryloyl butanedioic acid carbon spectrum
13c NMR (101MHz, DMSO) δ 171.07 (
coOH), 170.45 (
coOH), 165.07 (
coOC), 133.15 (H
2 c=C-), 128.05 (H
2c=
c-), 69.11 (O-
c(COOH)-), 36.19 (
ch
2-COOH).
Fig. 3 methacryl butanedioic acid hydrogen spectrum
1h NMR (400MHz, D
2o) δ=5.58 (s, 1H), 5.36 (s, 1H), 4.68 (t, 1H), 2.85 (dd, 2H), 1.92 (s, 1H), 1.79 (s, 3H)
Fig. 4 methacryl butanedioic acid Fourier infrared analysis spectrum spectrogram IR (cm
-1, KBr): 3222cm
-1-OH stretching vibration absworption peak (a small amount of water peak); 2950cm
-1– CH
2-,-CH
3hydrocarbon key stretching vibration absworption peak; 2612cm
-1-COOH hydroxyl stretching vibration absworption peak; 1720cm
-1overlap peak, comprises ester bond carbonyl, carboxylic acid carbonyl absorption peak; 1634cm
-1the two key stretching vibration absworption peaks of-C=C-; Fingerprint region 1414cm
-1, 1282cm
-1for methylene, the hydrocarbon flexural vibrations absworption peak of methyl; 886cm
-1there is obvious R at place
2c=CH
2the hydrocarbon flexural vibrations absworption peak of structure.
The specific embodiment
Below in conjunction with the specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
1h NMR and
13c NMR is respectively at deuterated D
2in O and DMSO, in model, be to test on Avance 400 instruments; Fourier's infrared spectrum is the upper test of AVATAR 380 (Thermo Electron Corp.) in model; Creasy recovery angle WRA bioassay standard is AATCC 66-2003, at " SHIRLEY " Crease Recovery Tester and Loading Device (TNG01) (U.S. TONNY Instrument Co.Ltd), tests; Whiteness is according to the measuring brightness > > method of AATCC110-2005 < < textiles, in Computer color testing color matching instrument Datacolor-650 (U.S. Datacolor company) test.
Embodiment 1
Acryloyl malic acid monomer is synthetic and for anti-crease finishing:
Magneton is being housed and is dewatering, add malic acid (2.68g, 20mmol) in deoxygenation three neck round-bottomed flasks, anhydrous tetrahydro furan THF (20mL) dissolves, N
2protection, stirring at normal temperature, to all dissolving, adds triethylamine (5.37g; 60mmol), put ice bath, acryloyl chloride (1.99g; 21mmol) with THF (10mL), dissolve, 2h is added dropwise to bottle, adds 30 ℃ of reaction 24h of rear room temperature; then, enriching HCl regulates pH to 2～3, and reactant liquor is spin-dried for; with ethyl acetate extraction, obtain thick product, column chromatography for separation obtains faint yellow solid; be sterling, productive rate approximately 70%.Its hydrogen spectrum as shown in Figure 1, compose as shown in Figure 2 by carbon.
Acryloyl malic acid (SA) arranges contrast with maleic acid (MA), itaconic acid (ITA) for cotton fabric crease-shedding:
Reaction is obtained to acryloyl malic acid monomer (SA) product for the noniron finish of COTTON FABRIC; preparation dressing liquid; fill a prescription as follows: fabric (plain weave poplin cloth 40Sx40S) 10g; acryloyl malic acid (SA) 0.5mol/L, MA 0.5mol/L, ITA 0.5mol/L; inferior sodium phosphate (SHP) 10g/L; potassium peroxydisulfate (KSO) 10g/L, strong protecting agent 10g/L, softener 10g/L.
Normal temperature pads, and two soak two rolls, 90%, 85 ℃ of prebake 5min of pick-up, and 160 ℃ bake 3min, and test result is as follows:
Note: single fabric sample is 10g, J and W represent respectively fabric warp-wise and broadwise, S.R. is fabric tearing brute force retention rate, CIE W. is fabric whiteness, WRA is wrinkle recovery angle of woven fabrics using viscoelasticity theory, after identical in embodiment.
Data analysis shows that synthetic acryloyl butanedioic acid has anti-wrinkle effect, approaches with maleic acid effect, and after arranging, fabric strength, whiteness keep good.
Embodiment 2
Acryloyl aspartic acid monomer is synthetic and for anti-crease finishing:
In being housed, three neck round-bottomed flasks of magneton and thermometer add aspartic acid (13.3g, 0.1mol), methyl ethyl ketone 50mL, NaOH (12g, 0.3mol), puts ice bath and stirs 30min, drip acryloyl chloride (16.8g, 0.11mol), 1h drips completely, room temperature reaction 6h, reaction is finished, and adds dense HCl to regulate pH to 2～3, and column chromatography for separation obtains white solid, productive rate 82%, is acryloyl aspartic acid monomer.Fourier's infrared spectrum analysis as shown in Figure 3
Reaction is obtained to acryloyl aspartic acid monomer product for the noniron finish of COTTON FABRIC, and preparation dressing liquid, fills a prescription as follows: acryloyl aspartic acid monomer 1.0mol/L, SHP 20g/L, KSO 20g/L, strong protecting agent 10g/L, softener 10g/L.
Normal temperature pads, and two soak two rolls, 90%, 80 ℃ of prebake 10min of pick-up, and 170 ℃ bake 4min, and test result is as follows:
Note: the meaning of table Chinese and English abbreviation is shown in example 1.
COTTON FABRIC, after acryloyl aspartic acid monomer arranges, has anti-wrinkle effect, and whiteness and powerful maintenance well, can be used for COTTON FABRIC free formaldehyde DP finish.
Embodiment 3
Acryloyl tartaric acid monomer is synthetic and for anti-crease finishing:
Magneton is being housed and is dewatering, add tartaric acid (3.0g, 20mmol) in deoxygenation three neck round-bottomed flasks, acetone (20mL) dissolves, N
2protection, stirring at normal temperature, to all dissolving, is put ice bath, acryloyl chloride (4.0g; 42mmol) with acetone (10mL), dissolve, 2h is added dropwise to bottle, adds rear room temperature reaction 24h, then; be spin-dried for to obtain thick product, column chromatography for separation obtains faint yellow solid, is sterling, productive rate approximately 85%.Hydrogen spectrum spectrogram as shown in Figure 4
Reaction is obtained to acryloyl tartaric acid monomer product for the noniron finish of COTTON FABRIC, and preparation dressing liquid, fills a prescription as follows: acryloyl tartaric acid monomer 0.4mol/L, SHP 10g/L, KSO 10g/L.
Normal temperature pads, and two soak two rolls, 90%, 85 ℃ of prebake 10min of pick-up, and 170 ℃, 180 ℃ bake 3min, and test result is as follows:
Note: the meaning of table Chinese and English abbreviation is shown in example 1.
COTTON FABRIC, after acryloyl tartaric acid monomer arranges, has anti-wrinkle effect, and whiteness and powerful maintenance well, can be used for COTTON FABRIC free formaldehyde DP finish.
Embodiment 4
Acryloyl mercapto butanedioic acid monomer is synthetic and for anti-crease finishing:
Magneton is being housed and is dewatering, add mercapto succinic acid (3.0g, 20mmol) in deoxygenation three neck round-bottomed flasks, anhydrous tetrahydro furan THF (20mL) dissolves, N
2protection, stirring at normal temperature, to all dissolving, is put ice bath, and acryloyl chloride (4.0g, 42mmol) dissolves with THF (10mL); 2h is added dropwise to bottle, 60 ℃ of reaction 24h of oil bath, and reacting liquid filtering, filtrate is spin-dried for; obtain thick product, column chromatography for separation obtains yellow solid, is sterling, productive rate approximately 75%.
Reaction is obtained to acryloyl mercapto butanedioic acid product for the noniron finish of COTTON FABRIC, and preparation dressing liquid, fills a prescription as follows: acryloyl mercapto butanedioic acid monomer 0.4mol/L, SHP 10g/L, KSO 10g/L.
Normal temperature pads, and two soak two rolls, 70%, 100 ℃ of prebake 5min of pick-up, and 190 ℃ bake 2min, and test result is as follows:
Note: the meaning of table Chinese and English abbreviation is shown in example 1.
Use it for anti-crease finishing, with acryloyl malic acid effect, approach, can give fabric crease-resistant performance equally, fabric whiteness is slightly poor.
Embodiment 5
Acryloyl malic acid monomer (SA) arranges for cotton fabric crease-shedding:
Reaction is obtained to acryloyl malic acid monomer (SA) product for the noniron finish of COTTON FABRIC, preparation dressing liquid, fill a prescription as follows: fabric (plain weave poplin cloth 40Sx40S) 10g, acryloyl malic acid (SA) 0.5mol/L, inferior sodium phosphate (SHP) 10g/L.
Normal temperature pads, and two soak two rolls, 70%, 100 ℃ of prebake 3min of pick-up, and 170 ℃ bake 3min, and test result is as follows:
Note: the meaning of table Chinese and English abbreviation is shown in example 1.
Acryloyl malic acid for anti-crease finishing, can be given fabric crease-resistant performance under single catalyst condition.
Claims (8)
1. acryloyl butanedioic acid, for COTTON FABRIC free formaldehyde DP finish method, is characterized in that, comprises the following steps:
(1) preparation of anti-crease finishing liquid;
Anti-crease finishing liquid forms: acryloyl butanedioic acid monomer 0.4～1.0mol/L, catalyst 10～20g/L, strong protecting agent 0～10g/L, softener 0～10g/L;
(2) anti-crease finishing;
Employing is rolled and is cured finishing technique and carry out anti-crease finishing, 80～100 ℃ of preliminary drying temperature, and stoving temperature is controlled at 160～190 ℃;
Described acryloyl butanedioic acid monomer is acryloyl aspartic acid monomer, acryloyl malic acid monomer, acryloyl mercapto butanedioic acid monomer or acryloyl tartaric acid monomer.
2. acryloyl butanedioic acid according to claim 1 for COTTON FABRIC free formaldehyde DP finish method, is characterized in that, described acryloyl butanedioic acid monomer synthetic be take acryloyl chloride with containing active hydrogen butanedioic acid, be raw material synthesizing propylene acyl butanedioic acid monomer; Concrete steps are: by acryloyl chloride be dissolved in reaction dissolvent phase containing active hydrogen butanedioic acid; Then add thermal response, after reaction finishes; Reactant liquor decompression is spin-dried for, and obtains acryloyl butanedioic acid monomer.
3. acryloyl butanedioic acid according to claim 2, for COTTON FABRIC free formaldehyde DP finish method, is characterized in that, containing active hydrogen butanedioic acid and acryloyl chloride molar ratio, is 1.0:1.1～2.5.
4. according to the acryloyl butanedioic acid described in claim 2 or 3, be used for COTTON FABRIC free formaldehyde DP finish method, it is characterized in that, described is malic acid, tartaric acid, mercapto succinic acid or aspartic acid containing active hydrogen butanedioic acid.
5. acryloyl butanedioic acid according to claim 2, for COTTON FABRIC free formaldehyde DP finish method, is characterized in that, described heating reaction temperature is controlled between 30～80 ℃, and the reaction time is controlled at 6～24h.
6. acryloyl butanedioic acid according to claim 2 is for COTTON FABRIC free formaldehyde DP finish method, it is characterized in that, synthesizing of described acryloyl butanedioic acid monomer also comprises further purification, i.e. reactant liquor decompression is spin-dried for, revolve desolventizing layer, obtain the thick product of acryloyl butanedioic acid monomer; Thick product is selected column chromatography for separation, dry method loading, and eluant, eluent is selected ethyl acetate: the volume ratio of benzinum is 1:0.5～2, obtains acryloyl butanedioic acid monomer net product.
7. acryloyl butanedioic acid according to claim 1, for COTTON FABRIC free formaldehyde DP finish method, is characterized in that, described catalyst is one or more in potassium peroxydisulfate, ammonium persulfate, inferior sodium phosphate.
8. acryloyl butanedioic acid according to claim 1 for COTTON FABRIC free formaldehyde DP finish method, is characterized in that, described employing is rolled and cured finishing technique and refer to that normal temperature pads, two soak two rolls, pick-up 60～90%, 80～100 ℃ of prebake 3～10min, 160～190 ℃ are cured 2～4min.
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| CN104499278A (en) * | 2014-12-16 | 2015-04-08 | 东华大学 | Acryloyl succinic acid-based non-phosphorus catalysis method for formaldehyde-free crease-resistant finishing of cotton fabrics |
| CN105484027A (en) * | 2016-01-08 | 2016-04-13 | 湖州市千金丝织厂 | Novel formaldehyde-free crease-resist finishing agent and finishing process thereof |
| CN105747333A (en) * | 2014-12-16 | 2016-07-13 | 三六度(中国)有限公司 | Processing method of crease-resistant and non-ironing garment fabric |
| CN106758209A (en) * | 2017-01-16 | 2017-05-31 | 东华大学 | A kind of method that the crease-resistant bafta of high-tenacity is prepared under alkalescence condition |
| CN107829297A (en) * | 2017-11-23 | 2018-03-23 | 苏州经贸职业技术学院 | A kind of crease-resistant flexible fibre fabric and its method for sorting |
| CN110698447A (en) * | 2019-10-24 | 2020-01-17 | 泉州师范学院(石狮)生态智能织物工程技术研究院 | Aromatic carboxylic acid and application method thereof in formaldehyde-free crease-resistant finishing of cotton fabric |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104499278A (en) * | 2014-12-16 | 2015-04-08 | 东华大学 | Acryloyl succinic acid-based non-phosphorus catalysis method for formaldehyde-free crease-resistant finishing of cotton fabrics |
| CN105747333A (en) * | 2014-12-16 | 2016-07-13 | 三六度(中国)有限公司 | Processing method of crease-resistant and non-ironing garment fabric |
| CN105484027A (en) * | 2016-01-08 | 2016-04-13 | 湖州市千金丝织厂 | Novel formaldehyde-free crease-resist finishing agent and finishing process thereof |
| CN106758209A (en) * | 2017-01-16 | 2017-05-31 | 东华大学 | A kind of method that the crease-resistant bafta of high-tenacity is prepared under alkalescence condition |
| CN107829297A (en) * | 2017-11-23 | 2018-03-23 | 苏州经贸职业技术学院 | A kind of crease-resistant flexible fibre fabric and its method for sorting |
| CN110698447A (en) * | 2019-10-24 | 2020-01-17 | 泉州师范学院(石狮)生态智能织物工程技术研究院 | Aromatic carboxylic acid and application method thereof in formaldehyde-free crease-resistant finishing of cotton fabric |
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