CN101302268A - Formaldehyde-free silicone color fixing agent - Google Patents
Formaldehyde-free silicone color fixing agent Download PDFInfo
- Publication number
- CN101302268A CN101302268A CNA2008100401675A CN200810040167A CN101302268A CN 101302268 A CN101302268 A CN 101302268A CN A2008100401675 A CNA2008100401675 A CN A2008100401675A CN 200810040167 A CN200810040167 A CN 200810040167A CN 101302268 A CN101302268 A CN 101302268A
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- CN
- China
- Prior art keywords
- color
- laking agent
- ammonium chloride
- add
- fastness
- Prior art date
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- Granted
Links
- 229920001296 polysiloxane Polymers 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- -1 aldehyde compounds Chemical class 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000003999 initiator Substances 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004159 Potassium persulphate Substances 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- 235000019394 potassium persulphate Nutrition 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000004744 fabric Substances 0.000 abstract description 19
- 239000000460 chlorine Substances 0.000 abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 abstract description 13
- 238000005406 washing Methods 0.000 abstract description 6
- 239000000835 fiber Substances 0.000 abstract description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 abstract 2
- 229910052710 silicon Inorganic materials 0.000 abstract 2
- 239000010703 silicon Substances 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- 230000002194 synthesizing effect Effects 0.000 description 32
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 239000000975 dye Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229960000935 dehydrated alcohol Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920002545 silicone oil Polymers 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 235000019633 pungent taste Nutrition 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 description 6
- MLGWTHRHHANFCC-UHFFFAOYSA-N prop-2-en-1-amine;hydrochloride Chemical compound Cl.NCC=C MLGWTHRHHANFCC-UHFFFAOYSA-N 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 5
- 238000010908 decantation Methods 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000012263 liquid product Substances 0.000 description 5
- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 208000031639 Chromosome Deletion Diseases 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 206010016590 Fibrin deposition on lens postoperative Diseases 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- MPBRYMWMMKKRGC-UHFFFAOYSA-M carbocyanin DBTC Chemical compound [Br-].C1=CC=CC2=C([N+](=C(C=C(C)C=C3N(C4=C5C=CC=CC5=CC=C4S3)CC)S3)CC)C3=CC=C21 MPBRYMWMMKKRGC-UHFFFAOYSA-M 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
本发明涉及一种不含醛类化合物的有机硅固色剂。本发明所述的固色剂，是一种以季铵盐为主链段的高分子化合物，同时引入了有机硅链段和水溶性反应性基团(如羟基或/和卤素等)。所述高分子化合物中，氧离子基团能与染料中的阴离子基团反应生成色淀(固色)；其有机硅链段可以提高织物的柔软性，爽滑性，提高了湿摩擦牢度；而含羟基，氯基等基团可以和织物纤维反应形成交联结构，大大提高了织物的水洗牢度，湿摩擦牢度。因此，本发明所述的固色剂不仅绿色环保(不含醛类化合物)，而且具有良好的染色牢度。The invention relates to an organic silicon color-fixing agent without aldehyde compounds. The color-fixing agent described in the present invention is a polymer compound with quaternary ammonium salt as the main chain segment, and simultaneously introduces organic silicon chain segments and water-soluble reactive groups (such as hydroxyl or/and halogen, etc.). In the polymer compound, the oxygen ion group can react with the anion group in the dye to form a color lake (color fixation); its organic silicon segment can improve the softness and smoothness of the fabric, and improve the wet rubbing fastness ; And groups containing hydroxyl, chlorine and other groups can react with fabric fibers to form a cross-linked structure, which greatly improves the washing fastness and wet rubbing fastness of the fabric. Therefore, the color-fixing agent described in the present invention is not only environmentally friendly (does not contain aldehyde compounds), but also has good color fastness.
Description
Technical field
The present invention relates to a kind of laking agent that is used for dyeing, specifically, relate to a kind of organosilicon color fixing agent of not aldehyde-containing type compound.
Background technology
Substantive dyestuff, matching stain and reactive dyestuffs are used in the dyeing of cotton fibre usually.Substantive dyestuff, matching stain and reactive dyestuffs all are anionic dyestuffs, all contain water soluble groups such as sulfonic group, carboxyl in the molecule.Substantive dyestuff and matching stain all mainly are to rely on Van der Waals force and hydrogen bond to anchor on the fiber, and the fastness of set is limited, is easy to hydrolysis and fades in water, so generally all need to improve the coloration of textile materials fastness with laking agent.Contain reactive group in the reactive dyestuff molecule structure, can generate covalent linkage, so dyefastness is higher relatively with fiber-reactive.But reactive dyestuffs are in dyeing course, and dyestuff unreacted reactant and hydrolyzate can not be clean fully, and this part dyestuff will fade, and simultaneously, the covalent linkage that dyes on the thing also can the hydrolysis scission of link.The raising that requires along with the textile dyeing fastness still needs to use laking agent when dying some dark heavy colour fabrics.
Traditional laking agent (as: the resin laking agent of Dyhard RU 100 and formaldehyde condensation) is though can effectively improve the coloration of textile materials fastness, but because its formaldehyde content is higher (after laking agent is handled, free formaldehyde content is generally greater than 200mg/kg), harmful to human and environment.Therefore the development of aldehyde-free colour stabilizer enjoys chemists' concern.
When (even reaching more than the 10%owf) dye strength dyes more than using 5%owf, not quite a lot of with the amount of dye of fibrin reaction set, be very easy to produce hydrolysis, decolouring, cause colour fastness to reduce greatly.Laking agent in the market has apparent in view raising to washing, the soaping fastness of fabric, but the raising of fastness to wet rubbing is not all reached the ideal effect.Because when doing the test of " wet friction " fastness, the white cotton fine cloth that normally will wet rubs mutually with the dyeing cloth specimen of doing.The frictional coefficient that moisture on this moment wet white cotton fine cloth does not only play is lubricated, reduction and dry state painting cloth are mutual and the effect of raising smoothness, a kind of swelling, dissolving and adsorption have been played on the contrary: in friction process, make not participation react dyestuff (the referring generally to staining) swelling of set, dissolve, come off, and be adsorbed on rapidly on the white cotton fine cloth of wet test, so difficulty is very big aspect the fastness to wet rubbing that improves fabric.Thereby the aldehyde-free colour stabilizer of development of new becomes the technical issues that need to address of the present invention.
Existing aldehyde-free colour stabilizer exists deficiency aspect dyefastness.Therefore, the aldehyde-free colour stabilizer cost technical problem to be addressed by invention of development of new.
Summary of the invention
Because dye molecule is generally anionic compound, so we design laking agent is cation compound, both are reacted, produce more firm covalent linkage, the hydrophilic group of dye molecule is closed in and forms precipitation on the fabric, can prevent that like this dyestuff from coming off and hydrolysis from fabric because of ionization, thereby improve colour fastness.Simple table is shown following reaction formula:
DSO
3Na+FX→DSO
3F+NaX
D-is a dye matrix, and F-is a cation group in the laking agent.
In addition, laking agent is designed to superpolymer, makes it, cover caducous right dyestuff in the fabric face film forming; Also according to containing active group or crosslinking structure in the structure of cotton fiber design laking agent, make with toner and anchor at fabric face firmly simultaneously together with dyestuff; Thereby effectively improve the dyefastness of each side.
The said laking agent of the present invention, it is 1 by compound shown in compound shown in vinylsiloxane (vinyl silicone oil), the formula I and the formula II by mass ratio mainly: (2～10): 10, under 30 ℃～80 ℃ conditions, make initiator with Potassium Persulphate, copolymerization obtained in 5～20 hours;
Wherein: R
1And R
2Independently be selected from C respectively
1～C
6A kind of in the alkyl, R
3Be C
1～C
16The C of alkyl or replacement
1～C
16Alkyl, X are halogen (F, Cl, Br or I);
The C of said replacement
1～C
16Substituting group in the alkyl is selected from: halogen (F, Cl, Br or I), a kind of in hydroxyl or the phenyl, two or more.
In optimal technical scheme of the present invention, selected vinylsiloxane is that molecular weight is 950～1200, the content of vinyl is the vinylsiloxane of 5wt%～10wt%;
In another optimal technical scheme of the present invention, 60 ℃～80 ℃ of polymeric reaction temperatures, polymerization reaction time is 10-15 hour;
In another optimal technical scheme of the present invention, R
1And R
2Independently be selected from C respectively
1～C
3A kind of in the alkyl;
In another optimal technical scheme of the present invention, R
3Be benzyl, hexadecyl or 2-hydroxyl, 3-chloro-propyl group.
The method for preparing the said laking agent of the present invention (random copolymers) comprises the steps:
(1) preparation of partial monosomy (compound shown in formula I and the formula II):
With corresponding secondary amine is starting raw material, makes corresponding quaternary amine (compound shown in formula I and the formula II) with corresponding haloalkane reaction;
(2) being principal monomer by prepared quaternary amine of step (1) and vinylsiloxane (commercially available product), and satisfying feeds in raw material is: compound is 1 by mass ratio shown in compound shown in vinylsiloxane, the formula I and the formula II: (2～10): 10, under 30 ℃～80 ℃ conditions, make initiator with Potassium Persulphate, copolymerization obtained target compound (laking agent) in 5～20 hours.
Monomeric synthetic route is as follows:
Wherein: R
1, R
2, R
3Described identical with the implication of X with preamble.
Embodiment
Prepare the method for laking agent of the present invention, comprise the steps:
(1) preparation of partial monosomy:
Compound (1) and compound (2) were placed reactor in 1: 1 in molar ratio,, react 3-10 hour (preferred 5-8 hour) and get compound (3) in 0 ℃～60 ℃ (preferred 5 ℃～10 ℃);
Compound (3) can make compound shown in the formula II with compound (2) by above-mentioned similar approach again;
In like manner, compound (3) makes compound shown in the formula I with compound (4) reaction.
(2) preparation of laking agent:
Be 1 by mass ratio mainly: (2～10) with compound shown in compound shown in vinylsiloxane, the formula I and the formula II: 10, under 60 ℃～80 ℃ conditions, make initiator with Potassium Persulphate, copolymer-1 obtained target compound in 0～15 hour.
The organosilicon macromolecule aldehyde-free colour stabilizer of the present invention's preparation is compared with traditional laking agent, has safer, environmental protection, makes fabric possess more firm dyefastness, is not easy jaundice simultaneously.
Laking agent of the present invention, be a kind of be main segmental macromolecular compound with quaternary ammonium salt, introduced organosilicon segment and water-soluble reaction group (as hydroxyl or/and halogen etc.) simultaneously.In the described macromolecular compound, the oxonium ion group can generate color lake (fixation) with the anionic group reaction in the dyestuff; Its organosilicon segment can improve the flexibility of fabric, and smooth property has improved fastness to wet rubbing; And hydroxyl, groups such as chloro can form crosslinking structure with the fabric fibre reaction, have improved the washing fastness of fabric, fastness to wet rubbing greatly.Therefore, not only environmental protection of laking agent of the present invention (not aldehyde-containing type compound), and have good dye fastness and dye.
The invention will be further elaborated below by embodiment, and its purpose only is better to understand content of the present invention, and unrestricted protection scope of the present invention.
Embodiment 1
Synthesizing of DMAA:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl ammonium chloride:
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 3-4 hour, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of hexadecyldimethyl benzyl ammonium allyl ammonium chloride:
Get Virahol 100ml and place flask to make solvent, get hexadecyldimethyl benzyl ammonium tertiary amine 20ml and propenyl chloride 25ml, logical nitrogen protection, reaction is after 6-8 hour down at 60 ℃, and behind activated carbon decolorizing, the choosing steaming obtains weak yellow liquid after removing and desolvating.Synthesizing of laking agent:
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram, vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%) hexadecyldimethyl benzyl ammonium allyl ammonium chloride 2 grams, Hydroxyethyl acrylate 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Embodiment 2
Synthesizing of DMAA:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl ammonium chloride:
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 34 hours, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of dimethyl-allyl benzyl ammonium chloride:
Get Benzyl Chloride 9.633g (0.0761mol) in the 50ml there-necked flask, add the 10ml dehydrated alcohol again, get 7.128g DMAA (0.0837mol), be dissolved in the 5ml dehydrated alcohol, add in the constant pressure funnel, one side mouth is loaded onto reflux condensing tube and upper end dress monochlor(in)ate calcium drying tube, live (lucifuge) reaction system with black paper bag then, 60 ℃ of temperature of reaction, DMAA solution dripped off in 8 minutes, 60 ℃ of holding temperatures continue reaction 3 hours, and decompression steams the solvent dehydrated alcohol then, use 10ml anhydrous diethyl ether washing reaction thing 3 times again, make product be solid state, normal pressure steams the small amount of residual anhydrous diethyl ether, obtains the dimethyl-allyl benzyl ammonium chloride after the vacuum-drying.
Synthesizing of laking agent:
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%), methacrylic benzyl ammonium chloride 2 grams, Hydroxyethyl acrylate 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Embodiment 3
Synthesizing of DMAA:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl ammonium chloride:
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 3-4 hour, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride:
In the 100ml there-necked flask, add the 9ml DMAA, add 50ml acetone and make solvent, the 9ml epoxy chloropropane is added in the dropping funnel, control reaction temperature is at 60 ℃, epoxy chloropropane dripped off in 30 minutes, after reacting 6 hours, layering appears in product, obtains lower floor's viscous liquid product with decantation.
Synthesizing of laking agent
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%), dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride 2 grams, Hydroxyethyl acrylate 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Embodiment 4
Synthesizing of DMAA:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl ammonium chloride
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 3-4 hour, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride
In the 100ml there-necked flask, add the 9ml DMAA, add 50ml acetone and make solvent, the 9ml epoxy chloropropane is added in the dropping funnel, control reaction temperature is at 60 ℃, epoxy chloropropane dripped off in 30 minutes, after reacting 6 hours, layering appears in product, obtains lower floor's viscous liquid product with decantation.
Synthesizing of methacrylic benzyl ammonium chloride:
Get Benzyl Chloride 9.633g (0.0761mol) in the 50ml there-necked flask, add the 10ml dehydrated alcohol again, get 7.128g DMAA (0.0837mol), be dissolved in the 5ml dehydrated alcohol, add in the constant pressure funnel, one side mouth is loaded onto reflux condensing tube and upper end dress monochlor(in)ate calcium drying tube, live (lucifuge) reaction system with black paper bag then, 60 ℃ of temperature of reaction, DMAA solution dripped off in 8 minutes, 60 ℃ of holding temperatures continue reaction 3 hours, and decompression steams the solvent dehydrated alcohol then, use 10ml anhydrous diethyl ether washing reaction thing 3 times again, make product be solid state, normal pressure steams the small amount of residual anhydrous diethyl ether, obtains the dimethyl-allyl benzyl ammonium chloride after the vacuum-drying.
Synthesizing of laking agent:
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%), dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride 2 grams, methacrylic benzyl ammonium chloride 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Embodiment 5
Synthesizing of DMAA:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl alkyl ammomium chloride:
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 3-4 hour, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride:
In the 100ml there-necked flask, add the 9ml DMAA, add 50ml acetone and make solvent, the 9ml epoxy chloropropane is added in the dropping funnel, control reaction temperature is at 60 ℃, epoxy chloropropane dripped off in 30 minutes, after reacting 6 hours, layering appears in product, obtains lower floor's viscous liquid product with decantation.
Synthesizing of hexadecyldimethyl benzyl ammonium allyl ammonium chloride:
Get Virahol 100ml and place flask to make solvent, get hexadecyldimethyl benzyl ammonium tertiary amine 20ml and propenyl chloride 25ml, logical nitrogen protection, reaction is after 6-8 hour down at 60 ℃, and behind activated carbon decolorizing, the choosing steaming obtains weak yellow liquid after removing and desolvating.
Synthesizing of laking agent:
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%), dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride 2 grams, hexadecyldimethyl benzyl ammonium allyl ammonium chloride 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Embodiment 6
Synthesizing of DMAA:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl alkyl ammomium chloride
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 3-4 hour, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride:
In the 100ml there-necked flask, add the 9ml DMAA, add 50ml acetone and make solvent, the 9ml epoxy chloropropane is added in the dropping funnel, control reaction temperature is at 60 ℃, epoxy chloropropane dripped off in 30 minutes, after reacting 6 hours, layering appears in product, obtains lower floor's viscous liquid product with decantation.
Synthesizing of methacrylic benzyl ammonium chloride:
Get Benzyl Chloride 9.633g (0.0761mol) in the 50ml there-necked flask, add the 10ml dehydrated alcohol again, get 7.128g DMAA (0.0837mol), be dissolved in the 5ml dehydrated alcohol, add in the constant pressure funnel, one side mouth is loaded onto reflux condensing tube and upper end dress monochlor(in)ate calcium drying tube, live (lucifuge) reaction system with black paper bag then, 60 ℃ of temperature of reaction, DMAA solution dripped off in 8 minutes, 60 ℃ of holding temperatures continue reaction 3 hours, and decompression steams the solvent dehydrated alcohol then, use 10ml anhydrous diethyl ether washing reaction thing 3 times again, make product be solid state, normal pressure steams the small amount of residual anhydrous diethyl ether, obtains the dimethyl-allyl benzyl ammonium chloride after the vacuum-drying.
Synthesizing of laking agent:
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%), dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride 2 grams, methacrylic benzyl ammonium chloride 2 grams, Hydroxyethyl acrylate 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Embodiment 7
Synthesizing of methacrylic amine:
In the 100ml flask, add 45 gram dimethylamine solutions (33%), under 5 ℃ of conditions, alternately drip the propenyl chloride and the aqueous sodium hydroxide solution of same molar, react after 6 hours, product is divided into three layers of oil reservoir, water layer and solid layers, filter, get the upper strata oil reservoir behind the separatory, with obtaining faint yellow pungency liquid after the sodium hydrate solid drying.
Synthesizing of dimethyl diallyl alkyl ammomium chloride:
Add the 10ml DMAA and with the propenyl chloride of molar weight, add the 50ml acetone solvent again in the 100ml flask, carry out quaterisation under 60 ℃, react after 3-4 hour, layering appears in product, and separatory takes off a layer dimethyl diallyl ammonium chloride liquid.
Synthesizing of hexadecyldimethyl benzyl ammonium allyl ammonium chloride:
Get Virahol 100ml and place flask to make solvent, get hexadecyldimethyl benzyl ammonium tertiary amine 20ml and propenyl chloride 25ml, logical nitrogen protection, reaction is after 6-8 hour down at 60 ℃, and behind activated carbon decolorizing, the choosing steaming obtains weak yellow liquid after removing and desolvating.
Synthesizing of dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride:
In the 100ml there-necked flask, add the 9ml DMAA, add 50ml acetone and make solvent, the 9ml epoxy chloropropane is added in the dropping funnel, control reaction temperature is at 60 ℃, epoxy chloropropane dripped off in 30 minutes, after reacting 6 hours, layering appears in product, obtains lower floor's viscous liquid product with decantation.
Synthesizing of laking agent:
Get dimethyl diallyl ammonium chloride 10 grams, 1 gram vinyl silicone oil (molecular weight 950-1050, contents of ethylene are 5wt%), dimethyl-allyl (2-hydroxyl-3-chlorine) propyl ammonium chloride 2 grams, hexadecyldimethyl benzyl ammonium allyl ammonium chloride 2 grams, Hydroxyethyl acrylate 2 grams, K
2S
2O
8Get 0.040 gram as initiator, logical nitrogen protection was reacted 10-15 hour down at 60 ℃, and obtaining thickness village liquid is laking agent, and its performance (dyefastness) sees Table 1.
Table 1:
Annotate:
1. multiple, the Shi Lixin of Cui Lian. the production of color fixing agent Y and application [J]. Shenyang chemical industry .1991,2:37-39.
2. positively charged ion, Organosilicon dye fixing agent of reaction type and its preparation method (CN1583763).
Claims (5)
1, a kind of laking agent, it is characterized in that said laking agent is 1 by compound shown in compound shown in vinylsiloxane, the formula I and the formula II by mass ratio mainly: (2～10): 10, under 30 ℃～80 ℃ conditions, make initiator with Potassium Persulphate, copolymerization obtained in 5～20 hours;
Wherein: R
1And R
2Independently be selected from C respectively
1～C
6A kind of in the alkyl, R
3Be C
1～C
16The C of alkyl or replacement
1～C
16Alkyl, X are halogen;
The C of said replacement
1～C
16Substituting group in the alkyl is selected from: halogen, a kind of in hydroxyl or the phenyl, two or more.
2, laking agent as claimed in claim 1 is characterized in that, wherein the molecular weight of said vinylsiloxane is 950～1200, the content of vinyl is 5wt%～10wt%.
3, laking agent as claimed in claim 1 is characterized in that, wherein polymeric reaction temperature is 60 ℃～80 ℃, and polymerization reaction time is 10-15 hour.
4, as any described laking agent in the claim 1～3, it is characterized in that, wherein R
1And R
2Independently be selected from C respectively
1～C
3A kind of in the alkyl.
5, laking agent as claimed in claim 4 is characterized in that, wherein R
3Be benzyl, hexadecyl or 2-hydroxyl, 3-chloro-propyl group.
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| CN101608407B (en) * | 2009-07-04 | 2011-01-26 | 金根苗 | Production process for improving wet rubbing fastness of reactive dye |
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| CN103669041A (en) * | 2013-11-27 | 2014-03-26 | 江苏中新资源集团有限公司 | Fabric formaldehyde-free fixing agent and preparation method thereof |
| CN103709326A (en) * | 2013-12-27 | 2014-04-09 | 福建清源科技有限公司 | Preparation method of cationic organic silicon modified poly(diallyldimethylammonium chloride) fixing agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3706176A1 (en) * | 1987-02-26 | 1988-09-08 | Sandoz Ag | MIX WITH SYNERGISTIC PROPERTIES |
| DE3938918A1 (en) * | 1989-11-24 | 1991-05-29 | Sandoz Ag | BLENDS WITH SYNERGISTIC PROPERTIES |
| CN1259324C (en) * | 2004-06-09 | 2006-06-14 | 华东理工大学 | Cationic, reactive silicone color fixing agent and preparation method thereof |
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| CN103709326B (en) * | 2013-12-27 | 2016-04-13 | 福建清源科技有限公司 | A kind of preparation method of cation type organic silicon modified Poly Dimethyl Diallyl Ammonium Chloride laking agent |
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