CN1304461C - Polyurethane wool anti-felting finish agent and preparation method thereof - Google Patents
Polyurethane wool anti-felting finish agent and preparation method thereof Download PDFInfo
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- CN1304461C CN1304461C CNB2004100672838A CN200410067283A CN1304461C CN 1304461 C CN1304461 C CN 1304461C CN B2004100672838 A CNB2004100672838 A CN B2004100672838A CN 200410067283 A CN200410067283 A CN 200410067283A CN 1304461 C CN1304461 C CN 1304461C
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- polyether
- felting
- diisocyanate
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- wool
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Abstract
The present invention discloses a polyurethane wool anti-felting finishing agent and a preparation method thereof. In the preparation method, polyisocyanate, a polyatomic alcohol compound and a polyether modified polysiloxane compound react to generate a polyurethane prepolymer whose end group is an isocyanate group, and then sodium bisulfite solution and one or multiple organic solvents are then emulsified by end sealing; and finally, the pH is regulated to 2 to 6 by acid , and then the wool anti-felting finishing agent with anionic reactive organosilicon modified aqueous polyurethane is prepared. The product obtained by the preparation method is used for the anti-felting finishing of wool fabrics, has the advantages of conspicuous anti-felting effect, soft hand feeling and broad market prospect without harmful substances containing organochlorine, etc. is a green ecological auxiliary agent. The general formula of the structure of the anti-felting finishing agent is NaSO3OCHN-R-NHCOSO3Na.
Description
Technical field
The present invention relates to a kind of wool anti-felting finish agent, particularly a kind of with reactive organic silicon modified aqueous polyurethane wool anti-felting finish agent of the end capped anionic of sodium bisulfite and preparation method thereof.
Background technology
Wool fiber has unique scale structure, and this special construction has it and is different from other textile fibres felting property.The wool fiber aggregate is under certain temperature and humidity conditions, and repeatedly through the external force effect, volume can dwindle gradually, and it is close that the generation area shrinks, thickness increases, tissue becomes, and appearance fine and closely woven fine hair in surface hides and organizes lines.This fulling milling effect is used for fabric processing, can obtain extensive, style closely.If this fulling milling effect can not get control, will cause the product size instability, bad order, weavy grain are unclear, torsional deformation, thicken adverse consequences such as felting.This phenomenon especially is easier to take place when " machine washing " in washing process, brings inconvenience to the human consumer, this has been occurred in case fulling milling is the shrink proof finish of purpose.
The shrink proof finish (being antifelting treatment) of wool fabric usually is the working method that adopts chemistry or physics, the wool scale layer is carried out modification handle, and makes fabric in conventional laundry washer process felting not take place.
The starting of preventing felting and shrinking of wood fabric Study on Technology early, peak in the eighties in 20th century, and have proven technique to obtain the universal and application of industrialization, what obtain widespread usage in the world is the chlorination-He Kesaite shrink-proof process technology of International Wool Secretariat/Australian Union's science and the common exploitation of technical study tissue.At present, still have the non-shrinkable wool more than 70% to handle through chlorine and derivative thereof.In the chlorination of wool course of processing, can produce absorbable Organohalogen compounds AOX, thereby cause serious ecological environmental pollution. studies show that, AOX concentration is up to 3gm/L in the sewage of the shrinkproof treating processes of chlorination of wool one He Kesaite, and this quantity is far above the requirement of some national relevant environmental pollution legal provisions.
Summary of the invention
The technical issues that need to address of the present invention are to disclose a kind of polyurethane wool anti-felting finish agent and preparation method thereof, to overcome the above-mentioned defective that prior art exists.To satisfy the needs of relevant field development.
Polyurethane wool anti-felting finish agent of the present invention is the reactive organic silicon modified aqueous polyurethane anti-felting finish agent of a kind of anionic, and its general structure is as follows:
NaSO
3OCHN——R——NHCOSO
3Na
R represents a kind of and polyether-modified organopolysiloxane in polyether glycol or the polyester polyol and the cross-linking reaction thing of isocyanate group;
Preferred polyurethane wool anti-felting finish agent is for comprising end-blocking emulsive aqueous solution behind isophorone diisocyanate, six methylene diisocyanates, Xylene Diisocyanate, modification diimine MDI and polyol compounds, the organosilicon polyol reaction.
The reactive organic silicon modified aqueous polyurethane anti-felting finish agent of anionic of the present invention can adopt infrared method to characterize, and every data are as shown in the table;
| Absorption peak wave number/cm -1 | Relative intensity | Ownership |
| 3250～3500 2940，2860 2240～2280 2120 1770～1785 1715～1750 1689～1710 1600～1615 1520～1560 1450～1470 1380 1225～1235 | In by force very strong stronger | The cis NH stretching vibration CH of OH stretching, NHCO 2，CH 3C=O in C=O ester group C=O in the stretching vibration NCO characteristic absorption peak N=C=N absworption peak urea diketone ring (dimer), acid amides I key (C=O) isocyanuric acid ester (tripolymer) (1408～1430 peak being arranged in addition) phenyl ring C=C skeleton stretching vibration acid amides II key (N-H deformation vibration) CH2Formation vibration, CH 3Asymmetrical deformation vibration CH 3Symmetrical deformation vibration polyester C-O stretches or the OH formation vibration |
| 1060～1150 | Wide strong | C-O-C (fatty ether) absorption peak |
| 1000～1110 | Extremely wide strong | The Si-O-Si charateristic avsorption band |
| 3680±10 | By force | The Si-OH charateristic avsorption band |
Its number-average molecular weight is 2000～20000.
The preparation method of the reactive organic silicon modified aqueous polyurethane wool anti-felting finish agent of above-mentioned anionic comprises the steps:
With polyisocyanates and polyol compound and the reaction of polyether-modified polyorganosiloxane compounds, generating end group is the base polyurethane prepolymer for use as of isocyanate group, end-blocking emulsification in sodium sulfite solution and organic solvent then, with acid for adjusting pH to 2～6, make the reactive organic silicon modified aqueous polyurethane wool anti-felting finish agent of anionic at last;
Temperature of reaction is 30 ℃～140 ℃, and the reaction times is 1～8 hour;
Polyisocyanates, polyol compound, polyether-modified polyorganosiloxane compounds react according to following proportioning:
-NCO/OH=I.1～6, wherein :-NCO represents isocyanate group, OH represents: hydroxyl;
The mol ratio of polyol compound and polyether-modified polyorganosiloxane compounds is:
Polyol compound: polyether-modified polyorganosiloxane compounds=1: 1～9;
The add-on of sodium bisulfite is 1.1～1.2 times of free isocyanate molar weight;
The weight concentration of sodium sulfite solution is 10～40%;
Sodium sulfite solution with the volume of organic solvent ratio is:
Sodium sulfite solution: organic solvent=1: 1～5.
Said polyol compound comprises saturated or unsaturated polyol compound, preferred molecular weight is a kind of in affixture of 200～6000 polyethers, polyester, polycarbonate-based or dihydroxyphenyl propane and oxyethane, propylene oxide or butylene oxide ring etc., and its general structure is as follows:
N represents the polymerization degree, n=50～1000, and x represents functionality, x=5～1000, Y represents the initiator main chain, and it is 1～5 alkyl or hydrogen that R represents carbon atom;
Preferred polyether alcohol is selected from oxyethane, propylene oxide, tetrahydrofuran by polymerization product or its multipolymer or graft copolymer;
The polyether alcohol of being addressed adopts the commercially available prod;
Said polyester polyvalent alcohol is by ethylene glycol, 1,2-propylene glycol, 1, ammediol, 1,4-butyleneglycol, 1,3-butyleneglycol, neopentyl glycol, pentanediol, ethylene glycol, ethohexadiol, 1, polyvalent alcohols such as saturated and undersaturated low-molecular-weight diol such as 4-butynediol, dihydroxyphenyl propane, glycol ether, Triethylene glycol, dipropylene glycol, tripropylene glycol or glycerol, TriMethylolPropane(TMP) and tetramethylolmethane and aliphatic dibasic acid and aromatic acid are or/and the polycondensation product of carboxylic acid anhydride, cyclic lactone etc., and its general structure is as follows:
N1 represents the polymerization degree, n1=50～1000, and it is 1～10 alkylidene group that R ' represents carbonatoms, it is 1～16 alkylidene group that R1 represents carbonatoms;
Preferred polyester class polyvalent alcohol is selected from ethylene glycol, 1,2-propylene glycol, 1, ammediol and aliphatic dibasic acid and polycondensation products such as aromatic acid or/and carboxylic acid anhydride, cyclic lactone;
The polyether alcohol of being addressed adopts the commercially available prod;
Said dihydroxyphenyl propane class polyol structure general formula is as follows:
M, N represents the polymerization degree, N=10～50, M=10～40, N＞M
It is a kind of in 1000～4000 that preferred dihydroxyphenyl propane class polyvalent alcohol is selected from molecular weight;
The dihydroxyphenyl propane class polyvalent alcohol of being addressed adopts commercially available prod or document disclosed method to be prepared;
Said polyether-modified polyorganosiloxane compounds is that molecular weight is 200～6000 dibasic alcohol that contains silicon and polyol compound, and its general structure is as follows:
In the formula: n2 represents polyoxyethylene groups repeating segment number, n2=1～200, and x1 represents siloxanes continuous chain joint number, x1=1～100; M represents the methene chain joint number, m=1～100;
The polyether-modified polyorganosiloxane compounds of addressing adopts commercially available prod or document disclosed method to be prepared;
Said organic solvent comprises common organic solvent such as ketone, ethers, ester class or alcohols, one or more in preferred toluene, dimethylbenzene, acetone, methylethylketone, dimethyl formamide, ethanol, Virahol, ethyl acetate, butylacetate or the diethylene glycol ether etc.
Said polyisocyanates comprises aromatic polyisocyanate or aliphatic polyisocyante, preferred tolylene diisocyanate, diphenylmethanediisocyanate (MDI), blending MDI, polyether-modified MDI, carbodiimide modification MDI, poly methylene poly phenyl poly isocyanate (PAPI), 1, hexamethylene-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, naphthalene-1, the 5-vulcabond, Methylcyclohexyl diisocyanate, in dicyclohexyl methane diisocyanate or the tetramethylxylylene diisocyanate etc. one or more.
Water reactive based polyurethane anti-felting finish agent of the present invention can be used for the woolen antifelting treatment.
This anti-felting finish agent discharges-the NCO group after reaching the deblocking temperature, the crosslinked film forming of fiber surface or with the fibrous active radical reaction bonded, produce competent antifelting treatment effect, and do not discharge poisonous, deleterious material.
The reactive organic silicon modified aqueous polyurethane wool anti-felting finish agent that adopts the present invention to make, the preventing felting and shrinking of wood fabric effect of handling is remarkable, anti-felting effect can reach the IWS-TM31 standard, soft, not containing objectionable impuritiess such as organochlorine, is a kind of green ecotypical auxiliary agent, both can obtain to be satisfied with, can not damage simultaneously woolen softness, plentiful style again, have broad application prospects.
Embodiment
Embodiment 1
1. in the four-hole boiling flask of 500ml, add polyoxygenated third rare triol 9g, polyether-modified polyorganosiloxane compounds 19g; add isophorone diisocyanate 6g after the vacuum hydro-extraction, under nitrogen protection, 120 ℃ were reacted 5 hours; make base polyurethane prepolymer for use as ,-NCO content 4.1%.
2. in the four-hole boiling flask of 500ml, add methylethylketone 6g, stir adding aqueous solution of sodium bisulfite 45ml and the emulsification of trimethyl carbinol 45ml end-blocking after 10 minutes, add hydrochloric acid after 1 hour, regulate pH 4, obtain to contain the mixture of isophorone diisocyanate, solid content 37%.
Embodiment 2
1. in the four-hole boiling flask of 500ml, add polyoxygenated third rare glycol 10g, polyether-modified polyorganosiloxane compounds 18g; add six methylene diisocyanates (HDI) 9g after the vacuum hydro-extraction, under nitrogen protection, 120 ℃ were reacted 7 hours; make base polyurethane prepolymer for use as ,-NCO content 3.5%.
2. in the four-hole boiling flask of 500ml, add acetone 4g, stir adding aqueous solution of sodium bisulfite 45ml and the emulsification of Virahol 55ml end-blocking after 10 minutes, add hydrochloric acid after 1 hour, regulate PH 3～4, obtain to contain the mixture of six methylene diisocyanates, solid content 36%.
Embodiment 3
1. in the four-hole boiling flask of 500ml, add polyoxygenated third rare glycol 14g, polyether-modified polyorganosiloxane compounds 11g; add Xylene Diisocyanate (TDI) 8g after the vacuum hydro-extraction, under nitrogen protection, 80 ℃ were reacted 4 hours; make base polyurethane prepolymer for use as ,-NCO content 5.6%.
2. in the four-hole boiling flask of 500ml, add ethyl acetate 4g, stir adding aqueous solution of sodium bisulfite 50ml and the emulsification of ethanol 50ml end-blocking after 10 minutes, add hydrochloric acid after 1 hour, regulate PH 3～4, obtain to contain the mixture of Xylene Diisocyanate, solid content 35%.
Embodiment 4
1. in the four-hole boiling flask of 500ml, add polyoxygenated third rare glycol 14g, polyether-modified polyorganosiloxane compounds 11g; add modification diimine MDI10g after the vacuum hydro-extraction, under nitrogen protection, 80 ℃ were reacted 3 hours; make base polyurethane prepolymer for use as ,-NCO content 5.1%.
2. in the four-hole boiling flask of 500ml, add dimethyl formamide 4.5g, stir adding aqueous solution of sodium bisulfite 48ml and the emulsification of ethanol 62ml end-blocking after 10 minutes, add hydrochloric acid after 1 hour, regulate PH 3～4, obtain to contain the mixture of modification diimine MDI; Solid content 34%.
Embodiment 5
Wool fabric:
All woolen woman clothing (following machine grey cloth), yarn linear density 11.76tex * 2, weight 178g/m
2
The fabric anti-felting finishing technique:
1. working fluid is formed:
The anionic reactive organic silicon modified aqueous polyurethane wool anti-felting finish agent of 40 grams per liter embodiment 1,5 grams per liter sodium bicarbonate dressing liquids
2. technical process: adopt two soak two roll (mangle expression 95%), preliminary drying (80 ℃/3min), bake (160 ℃/4min).
Performance test:
1. felt proofing performance test
The mensuration of area felting rate is with reference to GB8628-88 testing standard and method.
2. yellowness index
Yellowness index bakes 1min with the style after handling at 180oC with reference to GB8424-87, the x of test fabric, y, z tristimulus values, the yellowness index of calculating fabric.The yellowness index calculation formula is YI=(X-Z)/Y) * 100%.
3. washing standard
With reference to AATCC 135-2000 standard.
4. feel test
The hand valuation of fabric adopts subjective sensory evaluation.
Table 1 Wool fabric anti-felting arrangement result
| The experiment number | Area felting rate (%) | Yellowness index (%) | Hand valuation | Washing back size/cm | ||
| Planeness | Pliability | Warp-wise | Broadwise | |||
| 1 2 3 | 0 -17.28 0.691 | 10.42 11.53 15.81 | Good job is good | Good job is good | 0 18.12 19.87 | 0 18.26 20.27 |
Annotate: 1-former state (not washing); 2-former state (1 washing); 3-former state anti-felting finish agent is handled (10 washings); The former state washing is preceding to be 20cm * 20cm through broadwise length
As shown in Table 1, wool fabric is handled through the reactive organic silicon modified aqueous polyurethane anti-felting finish agent of anionic, and repeatedly after the washing, soft, look diminishes, and anti-felting effect is remarkable.
Claims (5)
1. polyurethane wool anti-felting finish agent is characterized in that general structure is as follows:
NaSO
3OCHN——R——NHCOSO
3Na
On behalf of the cross-linking reaction thing of a kind of and polyether-modified organopolysiloxane in polyether glycol or the polyester polyol and polyisocyanates, R remove the residue of end group part, and its number-average molecular weight is 2000～20000;
The general structure of said polyether-modified organopolysiloxane is:
In the formula: n2=1～200, x1=1～100, m=1～100.
2. prepare the method for claim 1 polyurethane wool anti-felting finish agent, it is characterized in that, comprise the steps:
With polyisocyanates and polyether glycol or the pure and mild polyether-modified polyorganosiloxane compounds reaction of polyester polyols, generating end group is the base polyurethane prepolymer for use as of isocyanate group, end-blocking emulsification in sodium sulfite solution and organic solvent then, with acid for adjusting pH to 2～6, make the reactive organic silicon modified aqueous polyurethane wool anti-felting finish agent of anionic at last; Temperature of reaction is 30 ℃～140 ℃, and the reaction times is 1～8 hour.
3. method according to claim 2 is characterized in that, polyisocyanates, polyether glycol or polyester polyol, polyether-modified polyorganosiloxane compounds react according to following proportioning:
-NCO/OH=1.1～6, wherein :-NCO represents isocyanate group;
The mol ratio of polyether glycol or polyester polyol and polyether-modified polyorganosiloxane compounds is:
Polyether glycol or polyester polyol: polyether-modified polyorganosiloxane compounds=1: 1～9;
The add-on of sodium bisulfite is 1.1～1.2 times of free isocyanate groups molar weight;
The weight concentration of sodium sulfite solution is 10～40%;
Sodium sulfite solution with the volume of organic solvent ratio is:
Sodium sulfite solution: organic solvent=1: 1～5.
4. method according to claim 2 is characterized in that, said polyester polyol general structure is as follows:
N1 represents the polymerization degree, n1=50～1000, and it is 1～10 alkylidene group that R ' represents carbonatoms, it is 1～16 alkylidene group that R1 represents carbonatoms.
5. method according to claim 2, it is characterized in that, said polyisocyanates is: tolylene diisocyanate, diphenylmethanediisocyanate, poly methylene poly phenyl poly isocyanate, 1, hexamethylene-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, naphthalene-1, the 5-vulcabond, more than one in Methylcyclohexyl diisocyanate, dicyclohexyl methane diisocyanate or the tetramethylxylylene diisocyanate.
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100406489C (en) * | 2006-06-30 | 2008-07-30 | 东华大学 | Polyurethane modified gamma-aminopropyl-triethoxy-silane precursor and its hydrolyte |
| ITVA20070077A1 (en) * | 2007-10-15 | 2009-04-16 | Lamberti Spa | TREATMENT FOR WOOL |
| CN101307181B (en) * | 2008-07-02 | 2010-06-02 | 天津大学 | Anion polyurethane and amino silicon oil composite water dispersion, preparation and applications |
| CN101348554B (en) * | 2008-08-08 | 2011-05-04 | 山东东大一诺威聚氨酯有限公司 | Organosilicon modified aqueous polyurethane resin and preparation thereof |
| CN101906201B (en) * | 2010-07-01 | 2012-07-18 | 东华大学 | Method for preparing polyurethane finishing agent by modifying nanometer cellulose |
| CN102505490A (en) * | 2011-11-01 | 2012-06-20 | 吴江市北厍盛源纺织品助剂厂 | Preparation method of anti-fuzzing and anti-pilling polyurethane finishing agents |
| CN102505499A (en) * | 2011-11-01 | 2012-06-20 | 吴江市北厍盛源纺织品助剂厂 | Preparation method for organic silicon modified waterborne blending polyurethane wool anti-felting finishing agent |
| DE102015209627A1 (en) * | 2015-05-26 | 2016-12-01 | Rudolf Gmbh | Polyurethane organopolysiloxanes |
| CN106884331B (en) * | 2017-04-27 | 2019-09-20 | 广州红谷皮具有限公司 | A kind of polyurethane finishing agent preparation method |
| DE102018114549A1 (en) * | 2018-06-18 | 2019-12-19 | CHT Germany GmbH | Polyurethane organopolysiloxanes with carbodiimide groups |
| CN109023950B (en) * | 2018-07-10 | 2021-07-09 | 江苏阳光股份有限公司 | Shape-preserving finishing method for wool fabric |
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| US4098742A (en) * | 1977-01-24 | 1978-07-04 | Ciba-Geigy Corporation | Fluorine and silicone containing polymers |
| JPH11279950A (en) * | 1998-03-30 | 1999-10-12 | Nicca Chem Co Ltd | Anionic polyurethane type fiber-treating agent |
| CN1422305A (en) * | 2000-04-04 | 2003-06-04 | 西巴特殊化学品普法希股份有限公司 | Silicone compositions for treating wool materials |
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2004
- 2004-10-19 CN CNB2004100672838A patent/CN1304461C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098742A (en) * | 1977-01-24 | 1978-07-04 | Ciba-Geigy Corporation | Fluorine and silicone containing polymers |
| JPH11279950A (en) * | 1998-03-30 | 1999-10-12 | Nicca Chem Co Ltd | Anionic polyurethane type fiber-treating agent |
| CN1422305A (en) * | 2000-04-04 | 2003-06-04 | 西巴特殊化学品普法希股份有限公司 | Silicone compositions for treating wool materials |
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