CN104892946A - Polysiloxane modified polyamide-amine as well as preparation method and application thereof - Google Patents
Polysiloxane modified polyamide-amine as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses polysiloxane modified polyamide-amine as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly, adding allyl glycidyl ether, end-hydrogen-containing polysiloxane and chloroplatinic acid into a reactor for reflux reaction, thereby obtaining single-ended epoxy polysiloxane; and further adding single-ended epoxy polysiloxane and first generation polyamidoamine into a reactor, and stirring to react and purify, thereby obtaining polysiloxane grafted polyamide-amine (PAMAM-Si) of an arborization-linear structure. The preparation method disclosed by the invention is simple and relatively high in yield. The prepared polysiloxane grafted polyamide-amine contains multi-ended amino and can be solidly bonded with leather and dye; due to the grafted polysiloxane long chain, the leather can be good in waterproof softness; due to the arborization-linear structure, a certain filling effect can be achieved, and a product obtained when the polysiloxane modified polyamide-amine is used in leather retanning procedures can meet multiple functions of leather retanning.
Description
Technical field
The invention belongs to Chemicals field, be specifically related to a kind of polysiloxane-modified polyamide-amide and its preparation method and application.
Background technology
Large based on branch-shape polymer terminal functionality, reactive behavior is high and the feature of branched structure, is introduced in leather processing production process, can give leather many excellent properties.Siloxanes long-chain has splendid submissive, waterproof and permeable gas performance, and various silicone oil also in each operation of leather processing more to be seen.Amino End Group polyamide-amide relative molecular mass is less, amino content is higher, and reaction is comparatively active, therefore can prepare New function polymkeric substance by graft modification.
Retanning is the critical process of wet processing after tanning, and can improve perception quality and the leather particulates of leather.Although current retanning agent kind is more, several functions is also rare based on the retanning agent of one.Along with the change of people's consumption idea and the raising of environmental requirement, multi-functional product has become the new trend of development.
Summary of the invention
For solving problems of the prior art, a kind of polysiloxane-modified polyamide-amide of the present invention and its preparation method and application, the method is simple to operate, productive rate is high, and the polysiloxane-modified polyamide-amide (PAMAM-Si) of synthesis is multi-functional polymkeric substance, dendroid-linear structure has certain fillibility, and multiterminal hydrophile amino makes it be combined firmly with leather and dyestuff, and polysiloxane long-chain can make leather have excellent waterproof softness.
For achieving the above object, the technical solution used in the present invention is:
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: adding mol ratio in reaction vessel is 1:(0.8 ~ 1.0) end hydrogen containing siloxane and glycidyl allyl ether, and add catalyzer and the first solvent, mix the reaction of rear temperature rising reflux, temperature of reaction is 90 ~ 110 DEG C, reaction, to reacting completely, obtains single-ended epoxy group(ing) polysiloxane after purification;
Step 2: be 1:(0.8 ~ 1.0 in molar ratio) PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor, and add the second solvent, at 50 ~ 80 DEG C of temperature, carry out stirring reaction to complete, reaction terminates rear purification and obtains polysiloxane-modified polyamide-amide.
As a further improvement on the present invention, described catalyzer is Platinic chloride, and Platinic chloride add-on accounts for reactant total mass 0.15 ~ 0.35%.
As a further improvement on the present invention, described first solvent is toluene.
As a further improvement on the present invention, the concrete steps of purifying in described step one are: at 70 ~ 90 DEG C, remove the first solvent after reaction terminates, then solution is dissolved in methyl alcohol, stratification, gets supernatant liquid, pours out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, then repeated above-mentioned purification operations 2 ~ 3 times, obtained obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
As a further improvement on the present invention, described second solvent is Virahol or methyl alcohol.
As a further improvement on the present invention, the concrete steps of purifying in described step 2 are: reaction terminates rear elder generation at 40 ~ 60 DEG C of decompression removing second solvents, and then just crude product is dissolved in saturated aqueous common salt, then extracted with diethyl ether is used, get ether layer, then decompress filter, in triplicate; Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide.
As a further improvement on the present invention, in step one, the reaction times of back flow reaction is 4 ~ 6h, and the reaction times in step 2 is for being 4 ~ 6h.
The polysiloxane-modified polyamide-amide that above preparation method obtains.
Described polysiloxane-modified polyamide-amide is dendroid-linear structure polymkeric substance.
The application of polysiloxane-modified polyamide-amide in leather composite tanning agent.
Compared with prior art, beneficial effect of the present invention is:
The preparation method of polysiloxane-modified polyamide-amide provided by the invention, by the principle of addition reaction of silicon with hydrogen, first make glycidyl allyl ether under katalysis, generate single-ended epoxy group(ing) polysiloxane with end hydrogen containing siloxane, namely polysiloxane long-chain provides body; Again with single-ended epoxy group(ing) polysiloxane-grafted modification one PAMAM, namely introduce the hydrophobic grouping of long-chain in the end group upper part of synthesizing Amino End Group dendritic macromole, obtaining the polysiloxane-modified polyamide-amide of final product is a kind of dendroid-linear polymer.The present invention with glycidyl allyl ether, end hydrogen containing siloxane, Platinic chloride, a PAMAM is for raw material, because these material toxicity are low, biocompatibility is high, excellent performance, therefore, the present invention has the advantage that pollution is little, synthetic method simple and target product productive rate is high.
Polysiloxane-modified polyamide-amide provided by the invention, the end group of Amino End Group dendritic macromole introduces the polysiloxane of long-chain, dendroid-linear structure has certain fillibility, multiterminal hydrophile amino makes it be combined firmly with leather and dyestuff, and polysiloxane long-chain can make leather have excellent waterproof softness.
And the present invention consists of optimizing materials and proportioning and reaction conditions, the polysiloxane-modified polyamide-amide prepared is applied to leather retanning operation, the product of gained is compared with existing retanning agent, multiple functions of leather retanning can be met, such as leather physical and mechanical properties all strengthens, dye uptake and Bearable dry and wet wipe fastness significantly promote, and waterproof flexibility has significantly lifting etc.
Accompanying drawing explanation
Fig. 1 is the reacting flow chart of polysiloxane-modified polyamide-amide.
Fig. 2 is the infrared spectrum of polyamide-amide and polysiloxane-modified polyamide-amide.
Embodiment
The preparation method of a kind of polysiloxane-modified polyamide-amide of the present invention, comprises the following steps:
Step one: adding mol ratio in reaction vessel is 1:(0.8 ~ 1.0) end hydrogen containing siloxane and glycidyl allyl ether, and add catalyzer Platinic chloride and solvent, mix rear temperature rising reflux, removing reaction solvent, at 70 ~ 90 DEG C, solvent toluene is removed after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.The quality of the Platinic chloride added is 0.15 ~ 0.35% of reactant total mass, and temperature of reaction is 90 ~ 110 DEG C, and the reaction times is 4 ~ 6h.
Step 2: be 1:(0.8 ~ 1.0 in molar ratio) PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor, and add solvent, carry out stirring reaction, temperature of reaction is 50 ~ 80 DEG C, and the time is 4 ~ 6h.Reaction terminates rear elder generation at 40 ~ 60 DEG C of removal of solvent under reduced pressure Virahols or methyl alcohol, and then just crude product is dissolved in saturated aqueous common salt, then uses extracted with diethyl ether, gets ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Below in conjunction with specific embodiment, the preparation method to polysiloxane-modified polyamide-amide provided by the invention is described in further detail.
Embodiment one
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: add end hydrogen containing siloxane and glycidyl allyl ether that mol ratio is 1:0.8 in reaction vessel, solvent toluene, and add the catalyzer Platinic chloride of reactant total mass 0.15%, mix rear temperature rising reflux, reflux 4h at 90 DEG C of temperature, at 70 ~ 90 DEG C, reaction solvent toluene is removed after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
Step 2: for 1:1, one PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor in molar ratio, and add solvent Virahol or methyl alcohol, stir, then at 50 DEG C of constant temperature stirring reaction 4h, after reaction terminates, at 40 ~ 60 DEG C, decompression removes Virahol or methyl alcohol, is then dissolved in saturated aqueous common salt by crude product, use extracted with diethyl ether afterwards, get ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Step 3: polysiloxane-modified polyamide-amide is applied to leather retanning operation.
Embodiment two
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: add end hydrogen containing siloxane and glycidyl allyl ether that mol ratio is 1:0.9 in reaction vessel, solvent toluene, and add the catalyzer Platinic chloride of reactant total mass 0.15%, mix rear temperature rising reflux, reflux 5h at 90 DEG C of temperature, at 70 ~ 90 DEG C, reaction solvent toluene is removed after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
Step 2: for 1:1, one PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor in molar ratio, and add solvent Virahol, stir, then at 50 DEG C of constant temperature stirring reaction 4h, after reaction terminates, at 40 ~ 60 DEG C, decompression removes Virahol or methyl alcohol, is then dissolved in saturated aqueous common salt by crude product, use extracted with diethyl ether afterwards, get ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Step 3: polysiloxane-modified polyamide-amide is applied to leather retanning operation.
Embodiment three:
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: add end hydrogen containing siloxane and glycidyl allyl ether that mol ratio is 1:0.95 in reaction vessel, solvent toluene, and add the catalyzer Platinic chloride of reactant total mass 0.15%, mix rear temperature rising reflux, reflux 6h at 90 DEG C of temperature, at 70 ~ 90 DEG C, reaction solvent toluene is removed after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
Step 2: for 1:0.9, one PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor in molar ratio, and add solvent methanol, stir, then at 50 DEG C of constant temperature stirring reaction 4h, after reaction terminates, at 40 ~ 60 DEG C, decompression removes Virahol or methyl alcohol, is then dissolved in saturated aqueous common salt by crude product, use extracted with diethyl ether afterwards, get ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Step 3: polysiloxane-modified polyamide-amide is applied to leather retanning operation.
Embodiment four
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: add end hydrogen containing siloxane and glycidyl allyl ether that mol ratio is 1:0.95 in reaction vessel, solvent toluene, and add the catalyzer Platinic chloride of reactant total mass 0.15%, mix rear temperature rising reflux, reflux 6h at 90 DEG C of temperature, reaction solvent toluene is removed at 70 ~ 90 DEG C, except desolventizing after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
Step 2: for 1:0.95, one PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor in molar ratio, and add solvent methanol, stir, then at 50 DEG C of constant temperature stirring reaction 6h, after reaction terminates, at 40 ~ 60 DEG C, decompression removes Virahol or methyl alcohol, is then dissolved in saturated aqueous common salt by crude product, use extracted with diethyl ether afterwards, get ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Step 3: polysiloxane-modified polyamide-amide is applied to leather retanning operation.
Embodiment five
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: add end hydrogen containing siloxane and glycidyl allyl ether that mol ratio is 1:1 in reaction vessel, solvent toluene, and add the catalyzer Platinic chloride of reactant total mass 0.35%, mix rear temperature rising reflux, reflux 6h at 110 DEG C of temperature, reaction solvent toluene is removed at 70 ~ 90 DEG C, except desolventizing after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
Step 2: for 1:0.8, one PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor in molar ratio, and add solvent methanol, stir, then at 80 DEG C of constant temperature stirring reaction 6h, after reaction terminates, at 40 ~ 60 DEG C, decompression removes Virahol or methyl alcohol, is then dissolved in saturated aqueous common salt by crude product, use extracted with diethyl ether afterwards, get ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Step 3: polysiloxane-modified polyamide-amide is applied to leather retanning operation.
Embodiment six
A preparation method for polysiloxane-modified polyamide-amide, comprises the following steps:
Step one: add end hydrogen containing siloxane and glycidyl allyl ether that mol ratio is 1:15 in reaction vessel, solvent toluene, and add the catalyzer Platinic chloride of reactant total mass 0.35%, mix rear temperature rising reflux, reflux 6h at 100 DEG C of temperature, reaction solvent toluene is removed at 70 ~ 90 DEG C, except desolventizing after reaction terminates, then solution is dissolved in methyl alcohol, stratification, get supernatant liquid, pour out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, repeat above-mentioned purification operations 2 ~ 3 times again, obtain obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
Step 2: for 1:0.85, one PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor in molar ratio, and add solvent Virahol or methyl alcohol, stir, then at 70 DEG C of constant temperature stirring reaction 5h, after reaction terminates, at 40 ~ 60 DEG C, decompression removes Virahol or methyl alcohol, is then dissolved in saturated aqueous common salt by crude product, use extracted with diethyl ether afterwards, get ether layer, then decompress filter, in triplicate.Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide retanning agent.
Step 3: polysiloxane-modified polyamide-amide is applied to leather retanning operation.
Fig. 1 is synthetic line figure of the present invention, and by the principle of addition reaction of silicon with hydrogen, first make glycidyl allyl ether under katalysis, generate single-ended epoxy group(ing) polysiloxane with end hydrogen containing siloxane, namely polysiloxane long-chain provides body; Again with single-ended epoxy group(ing) polysiloxane-grafted modification one PAMAM, namely introduce the hydrophobic grouping of long-chain in the end group upper part of synthesizing Amino End Group dendritic macromole, obtaining the polysiloxane-modified polyamide-amide of final product is a kind of dendroid-linear polymer.
Fig. 2 is the infrared spectrum of polyamide-amide and polysiloxane-modified polyamide-amide, wherein 1260cm
-1place's peak absorption intensity is large and peak shape is sharp-pointed, simultaneously at 865 ~ 750cm
-1there is multiple strong peak at place, is the flexural vibration absorption peak of the C-H on the methyl that Siliciumatom is connected.1000 ~ 1130cm
-1place's peak shape is wide, and intensity is large, is the stretching vibration absorption peak of polysiloxane backbone Si-O-Si.At 2126cm
-1with 800 ~ 950cm
-1place has occurred that in end hydrogen silicone oil, Si-H stretches and the strong absorption peak of in-plane bending vibration, at 3700cm
-1with 2900cm
-1left and right place absorption peak strength strengthens, and shows that hydroxyl and methylene radical content increase, functional silicone oil grafting dendritic interphase grafting success.
Process with polysiloxane-modified polyamide-amide Retanning Agent on Leather prepared by the present invention, its every result is respectively as shown in table 1, table 2 and table 3.
Table 1
Table 1 is the impact of polysiloxane-modified polyamide-amide retanning agent on leather physical and mechanical properties after retanning.Result surface, when PAMAM-Si is used as retanning agent be applied to leather retanning operation after, no matter be tensile strength or tearing toughness, have lifting.Show that PAMAM-Si there occurs crosslinked action in leather inside.
Table 2
Table 2 is the impact of polysiloxane-modified polyamide-amide retanning agent on leather coloring fastness after retanning.Observe find, when PAMAM-Si is used as retanning agent be applied to leather retanning operation after, no matter be dye uptake or Bearable dry and wet wipe fastness, have obvious lifting.Show that in PAMAM-Si, amino can be combined with dyestuff effect, make this retanning agent have certain assistant dying energy.
Table 3
Table 3 is the impact of polysiloxane-modified polyamide-amide retanning agent on leather water-proof performance after retanning.Result surface, when PAMAM-Si is used as retanning agent be applied to leather retanning operation after, waterproof flexibility has obvious lifting.To show in PAMAM-Si that polysiloxane long-chain has waterproof and help soft energy.
The above results shows, is applied in leather retanning operation by polysiloxane-modified polyamide-amide retanning agent, obtains good effect, proves that PAMAM-Si can be applied in leather as the multi-functional retanning agent of one thus.
Claims (10)
1. a preparation method for polysiloxane-modified polyamide-amide, is characterized in that, comprises the following steps:
Step one: adding mol ratio in reaction vessel is 1:(0.8 ~ 1.0) end hydrogen containing siloxane and glycidyl allyl ether, and add catalyzer and the first solvent, mix the reaction of rear temperature rising reflux, temperature of reaction is 90 ~ 110 DEG C, reaction, to reacting completely, obtains single-ended epoxy group(ing) polysiloxane after purification;
Step 2: be 1:(0.8 ~ 1.0 in molar ratio) PAMAM and single-ended epoxy group(ing) polysiloxane are joined in reactor, and add the second solvent, at 50 ~ 80 DEG C of temperature, carry out stirring reaction to complete, reaction terminates rear purification and obtains polysiloxane-modified polyamide-amide.
2. the preparation method of polysiloxane-modified polyamide-amide according to claim 1, is characterized in that: described catalyzer is Platinic chloride, and Platinic chloride add-on accounts for reactant total mass 0.15 ~ 0.35%.
3. the preparation method of polysiloxane-modified polyamide-amide according to claim 1, is characterized in that: described first solvent is toluene.
4. the preparation method of polysiloxane-modified polyamide-amide according to claim 1, it is characterized in that: the concrete steps of purifying in described step one are: after reaction terminates, at 70 ~ 90 DEG C, remove the first solvent, then solution is dissolved in methyl alcohol, stratification, gets supernatant liquid, pours out lower floor's oily liquids, then decompression steams methyl alcohol at 40 ~ 60 DEG C, slightly carried product, then repeated above-mentioned purification operations 2 ~ 3 times, obtained obtaining white clear oily liquids and single-ended epoxy group(ing) polysiloxane.
5. the preparation method of polysiloxane-modified polyamide-amide according to claim 1, is characterized in that: described second solvent is Virahol or methyl alcohol.
6. the preparation method of polysiloxane-modified polyamide-amide according to claim 1, it is characterized in that: the concrete steps of purifying in described step 2 are: reaction terminates rear elder generation at 40 ~ 60 DEG C of decompression removing second solvents, then just crude product is dissolved in saturated aqueous common salt, then extracted with diethyl ether is used, get ether layer, then decompress filter, in triplicate; Remove a unreacted PAMAM by aforesaid operations, obtain polysiloxane-modified polyamide-amide.
7. the preparation method of polysiloxane-modified polyamide-amide according to claim 1, is characterized in that, in step one, the reaction times of back flow reaction is 4 ~ 6h, and the reaction times in step 2 is for being 4 ~ 6h.
8. the polysiloxane-modified polyamide-amide that obtains of the preparation method according to claim 1 to 7 any one.
9. polysiloxane-modified polyamide-amide according to claim 8, is characterized in that, described polysiloxane-modified polyamide-amide is dendroid-linear structure polymkeric substance.
10. the application of polysiloxane-modified polyamide-amide in leather composite tanning agent described in claim 8 or 9.
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