CN110423333A - A kind of soft cryobranding color-changing polyurethane resin and its preparation method and application - Google Patents
A kind of soft cryobranding color-changing polyurethane resin and its preparation method and application Download PDFInfo
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- CN110423333A CN110423333A CN201910606301.1A CN201910606301A CN110423333A CN 110423333 A CN110423333 A CN 110423333A CN 201910606301 A CN201910606301 A CN 201910606301A CN 110423333 A CN110423333 A CN 110423333A
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- polyurethane resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N2211/00—Specially adapted uses
- D06N2211/12—Decorative or sun protection articles
- D06N2211/28—Artificial leather
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of soft cryobranding color-changing polyurethane resins (PU resin) and its preparation method and application, and the polyurethane resin is by the polyester polyol by number-average molecular weight for 6000, antioxidant, H3PO4, chain extender, isocyanates, methanol, catalyst and color spreading agent react to obtain, and method preparation is not viscosified using 2 step constant temperature, obtained polyurethane resin is soft, and the wet process bass of preparation possesses preferable burnt discoloration performance under cryogenic, has a vast market foreground.
Description
Technical field
The invention belongs to polyurethane resin fields, specifically relate to a kind of soft cryobranding color-changing polyurethane resin and its preparation
Methods and applications.
Background technique
As the substitute of natural leather, Synthetic Leather is because of its excellent waterproof, cold-resistant, wear-resisting and tearing strength etc.
Feature is widely used in the fields such as clothes, luggage, label and packaging.
In traditional handicraft, the polyurethane resin (PU resin) for being used to prepare Synthetic Leather is by polyadipate ethylene glycol
Ester, poly adipate succinic acid ester and polyadipate hexylene glycol ester etc. have more regular molecular chain structure, crystal property stronger
Polyester polyol react to obtain with the viscous pre-polymerization method that rises by traditional one-step method, obtained Synthetic Leather material compared with
Firmly, and under cryogenic burnt discoloration performance is poor, and cryogenic conditions require lower to apparatus for preparation heating, compares hot conditions
Preparation can save mass production cost, can but reach same effect.
Summary of the invention
In order to solve the above technical problems, the present invention provides a kind of soft cryobranding color-changing polyurethane resins, by counting
Average molecular weight be 6000 polyester polyol, antioxidant, H3PO4, chain extender, isocyanates, methanol, catalyst and color spreading agent
Reaction obtains.
The polyester polyol can be polyadipate ethylene glycol butanediol ester (PEBA) and polyadipate ethylene glycol hexylene glycol
One or both of ester (PEHA).The polyester polyol of the high molecular weight has a longer carbon-chain structure, carbon-chain structure compared with
The spacing between polyurethane resin hard section prepared when long is larger, and the Hyarogen-bonding between hard section is weaker, the synthesis prepared
Remove from office soft, and crystal property is weaker, and the spacing between the long-chain polyurethane resin of formation is larger, is conducive to dyestuff on it
Load, the gorgeous degree of the synthetic leather prepared color with higher, while the softening point of the polyalcohol of 6000 molecular weight is smaller,
Burnt discoloration processing more easily is carried out to synthetic leather under cryogenic.Two different dihydric alcohols can be used in the present invention, one
That determines degree plays chemiluminescence, can enhance the comprehensive physical performance of synthetic leather.
Further, the glycol chain extender with pending methyl group structure can be used in the present invention, concretely trimethyl penta 2
One or both of alcohol and methyl propanediol, the presence of pending methyl group increase the steric hindrance between molecular resin, help to drop
The crystal property of low resin, so that the polyurethane resin of preparation has good flexibility and cryogenic property, while pending methyl group band
There is certain hydrophobic and smooth effect, the viscosity of synthetic leather can be reduced.
Further, the isocyanates can be lysine diisocyanate.
Further, the catalyst can be bismuth carboxylate.
Further, the color spreading agent can be BYK161.
Further, color spreading agent can be selected with polyamino functional group, concretely BYK161.The pole of amido functional group
Property more by force be easy with dyestuff surface existing for epoxy-functional formed hydrogen bond so that dyestuff is firmly adsorbed on polyurethane resin
Surface can enable the synthetic leather of preparation have more chromatic colour.
Invention further provides the preparation methods of the soft cryobranding color-changing polyurethane resin, it may include: (1)
By solvent, the polyester polyol that a kind of number-average molecular weight is 6000, antioxidant, H3PO4, chain extender is separately added into reaction unit
20min is stirred, then isocyanates is added thereto, reacts 1h at 70~75 DEG C；(2) solvent, same or another is continuously added
A kind of polyester polyol that number-average molecular weight is 6000, chain extender stir 20min, then isocyanates are added thereto, in 70
1h is reacted at~75 DEG C；(3) supplement be added isocyanates, reaction thickening, thickening during be added solvent to reaction mixture into
Row constantly dilution；(4) catalyst is added when reaction terminating to react with methanol；(5) catalyst with methanol reaction terminating when continue to stir
Color spreading agent is added after mixing 1h, continues stirring 1h and obtains the polyurethane resin.
It is different from traditional one-step method and long viscous pre-polymerization method, the preparation method that the present invention uses is the 2 step constant temperature not side of thickening
Method facilitates the structural regularity for reducing polyurethane resin, reduces softening point, improve bass under the premise of not improving hardness
Thickness etc., and R value (ratio that R value is hydroxyl and isocyanates in reaction system) design in reaction process is lower, it will not
Significantly affect the feel of resin.It is terminated after reaction process using methanol and catalyst, different from conventional terminating party
Formula.The viscosity of system is higher when terminating reaction, and a small amount of methanol can not carry out with isocyanates remaining in system anti-completely
It answers.Therefore methanol and catalyst are added in reaction kettle simultaneously, are improved between methanol and remaining isocyanates by catalyst
Reactivity, free isocyanate group is completely reacted.Color spreading agent is added after reaction, due in system
Without remaining isocyanates, therefore addition color spreading agent will not cause cross-linking reaction.
Further, the present invention also provides the polyurethane resins to prepare the purposes in polyurethane wet bass.
The utility model has the advantages that
Polyurethane resin of the invention is soft, and manufactured bass thickness is larger, at low temperature, especially 150 DEG C
There is down good burnt discoloration effect, while there is good color development performance.
Detailed description of the invention:
Fig. 1 is the flow diagram using polyurethane resin of the present invention preparation wet process bass.
Specific embodiment
The present invention is described in further detail with reference to the accompanying drawings and examples.Following embodiment is merely to illustrate this
Invention rather than the limitation scope of the invention.Test method without specific conditions in embodiment, is considered as this field
Normal condition carries out.
Embodiment 1
In the four-hole boiling flask of 2000ml, be added 200g solvent DMF, 200g PEBA-6000,0.2g antioxidant BHT,
0.003g H3PO4, 6g trimethylpentanediol, after stirring 20min, then lysine diisocyanate is added thereto (R value is
0.65), while 70~75 DEG C are warming up to, reaction 1h.200g DMF, 200g PEHA-6000 and 6g methyl is added into system again
Propylene glycol is stirring evenly and then adding into lysine diisocyanate (R value is 0.65), while being warming up to 70~75 DEG C, reacts 1h.So
It adds lysine diisocyanate (R value is 1) into system again afterwards and starts thickening reaction, DMF is added constantly into system and is carried out
Dilution.Add methanol and catalyst bismuth carboxylate when reaction terminating, continue to stir 1h, then be added thereto 3g color spreading agent BYK161 after
Continuous stirring 1h control viscosity is 22~280,000, solid content 30%, discharging.
Embodiment 2
In the four-hole boiling flask of 2000ml, 200g solvent DMF, 100g PEBA-6000,0.2g antioxidant aryl pair is added
Phenylenediamine, 0.003g H3PO4, 6g trimethylpentanediol, stir 20min after, then thereto be added lysine diisocyanate (R
Value is warming up to 70~75 DEG C for 0.65), reacts 1h.300g DMF, 200g PEHA-6000 and 6g is added into system again
Methyl propanediol is stirring evenly and then adding into lysine diisocyanate (R value is 0.65), while being warming up to 70~75 DEG C, reacts
1h.Then lysine diisocyanate (R value is 1) is added into system again and starts thickening reaction, DMF is constantly added into system
It is diluted.Methanol and catalyst bismuth carboxylate are added when reaction terminating, continue to stir 1h, then 3g color spreading agent is added thereto
BYK161 continues to stir 1h control viscosity to be 22~280,000, solid content 30%, discharging.
Embodiment 3
In the four-hole boiling flask of 2000ml, 200g solvent DMF, 300g PEBA-6000, four phenylpropyl alcohol of 0.2g antioxidant is added
Sour pentaerythrite, 0.003g H3PO4, 6g trimethylpentanediol, stir 20min after, then thereto be added lysine diisocyanate
Ester (R value is 0.65), while 70~75 DEG C are warming up to, react 1h.300g DMF, 100gPEHA-6000 is added into system again
And 6g methyl propanediol is stirring evenly and then adding into lysine diisocyanate (R value is 0.65), while being warming up to 70~75 DEG C, instead
Answer 1h.Then lysine diisocyanate (R value is 1) is added into system again and starts thickening reaction, is constantly added into system
DMF is diluted.Methanol and catalyst bismuth carboxylate are added when reaction terminating, continue to stir 1h, then 3g color spreading agent is added thereto
BYK161 continues to stir 1h control viscosity to be 22~280,000, solid content 30%, discharging.
Embodiment 4
In the four-hole boiling flask of 2000ml, it is octylatcd that 200g solvent DMF, 300g PEBA-6000,0.2g antioxidant is added
Diphenylamines, 0.003g H3PO4, 3g trimethylpentanediol, stir 20min after, then thereto be added lysine diisocyanate (R
Value is warming up to 70~75 DEG C for 0.65), reacts 1h.300g DMF, 100g PEHA-6000 and 9g is added into system again
Methyl propanediol is stirring evenly and then adding into lysine diisocyanate (R value is 0.65), while being warming up to 70~75 DEG C, reacts
1h.Then lysine diisocyanate (R value is 1) is added into system again and starts thickening reaction, DMF is constantly added into system
It is diluted.Methanol and catalyst bismuth carboxylate are added when reaction terminating, continue to stir 1h, then 3g color spreading agent is added thereto
BYK161 continues to stir 1h control viscosity to be 22~280,000, solid content 30%, discharging.
Embodiment 5
In the four-hole boiling flask of 2000ml, 200g solvent DMF, 300g PEBA-6000,0.2g antioxidant dihydro quinoline is added
Quinoline, 0.003g H3PO4, 9g trimethylpentanediol, after stirring 20min, then lysine diisocyanate is added thereto (R value is
0.65), while 70~75 DEG C are warming up to, reaction 1h.300g DMF, 100g PEHA-6000 and 3g methyl is added into system again
Propylene glycol is stirring evenly and then adding into lysine diisocyanate (R value is 0.65), while being warming up to 70~75 DEG C, reacts 1h.So
It adds lysine diisocyanate (R value is 1) into system again afterwards and starts thickening reaction, DMF is added constantly into system and is carried out
Dilution.Add methanol and catalyst bismuth carboxylate when reaction terminating, continue to stir 1h, then be added thereto 3g color spreading agent BYK161 after
Continuous stirring 1h control viscosity is 22~280,000, solid content 30%, discharging.
Embodiment 6
Wet process bass is made in the polyurethane resin prepared in above-mentioned 5 embodiments, specific steps as shown in Figure 1 are such as
Under: by the polyurethane resin sampling 100g of examples detailed above synthesis, 30g calcium powder, 27g wood powder, 1g mill base and 100g DMF is added,
After high speed dispersion is uniform, vacuum defoamation is stand-by.By the slurry coating after deaeration in spunlace non-woven cloth surface, coating thickness is
1.2mm, and place it in the DMF coagulating basin containing 25%, 15min is solidified, is then washed.In 120 after the completion of washing
Drying can be prepared by polyurethane wet bass in DEG C baking oven.
This polyurethane wet bass is performed the following performance tests after the completion of above-mentioned preparation step: 1) the soft or hard survey of feel
Examination, 2) cryobranding discoloration test, 3) peel strength and 4) bass thickness.
The results are shown in Table 1 for above-described embodiment, wherein wet process shellfish made of the polyurethane resin of embodiment 2-5 synthesis
This all has feature soft, that cryobranding discoloration is good.
The comparison of the soft cryobranding color-changing polyurethane wet process bass physical property of table 1
Claims (9)
1. a kind of soft cryobranding color-changing polyurethane resin, which is characterized in that the resin is 6000 by number-average molecular weight
Polyester polyol, antioxidant, H3PO4, chain extender, isocyanates, methanol, catalyst and color spreading agent react to obtain.
2. polyurethane resin according to claim 1, which is characterized in that the polyester polyol is polyadipate ethylene glycol
One or both of butanediol ester and polyadipate ethylene glycol hexylene glycol ester.
3. polyurethane resin according to claim 1, which is characterized in that the chain extender is two with pending methyl group structure
First alcohol.
4. polyurethane resin according to claim 3, which is characterized in that the dihydric alcohol is trimethylpentanediol and methyl
One or both of propylene glycol.
5. polyurethane resin according to claim 1, which is characterized in that the isocyanates is lysine diisocyanate
Ester.
6. polyurethane resin according to claim 1, which is characterized in that the catalyst is bismuth carboxylate.
7. polyurethane resin according to claim 1, which is characterized in that the color spreading agent is BYK161.
8. the preparation method of polyurethane resin according to claim 1, comprising:
(1) by solvent, the polyester polyol that a kind of number-average molecular weight is 6000, antioxidant, H3PO4, chain extender be separately added into reaction
20min is stirred in device, then isocyanates is added thereto, reacts 1h at 70~75 DEG C；
(2) solvent is continuously added, the polyester polyol that same or another number-average molecular weight is 6000, chain extender stirring
20min, then isocyanates is added thereto, 1h is reacted at 70~75 DEG C；
(3) isocyanates is added in supplement, and reaction thickening is added solvent during viscosifying and is constantly diluted to reaction mixture；
(4) catalyst is added when reaction terminating to react with methanol；
(5) catalyst and when methanol reaction terminating, continue that color spreading agent is added after stirring 1h, continue to stir 1h obtaining the polyurethane
Resin.
9. polyurethane resin according to claim 1 is preparing the purposes in polyurethane wet bass.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910606301.1A CN110423333A (en) | 2019-07-05 | 2019-07-05 | A kind of soft cryobranding color-changing polyurethane resin and its preparation method and application |
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| CN201910606301.1A CN110423333A (en) | 2019-07-05 | 2019-07-05 | A kind of soft cryobranding color-changing polyurethane resin and its preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111363343A (en) * | 2020-03-31 | 2020-07-03 | 扬州工业职业技术学院 | Dry-process fabric resin for high-temperature-resistant protein PU leather and preparation method thereof |
| CN113501929A (en) * | 2021-07-27 | 2021-10-15 | 扬州工业职业技术学院 | Flame-retardant wear-resistant polyurethane resin for leather |
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| CN113501929A (en) * | 2021-07-27 | 2021-10-15 | 扬州工业职业技术学院 | Flame-retardant wear-resistant polyurethane resin for leather |
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