CN106047262B - The reflective preparation process for taking polyurethane resin composite glue - Google Patents
The reflective preparation process for taking polyurethane resin composite glue Download PDFInfo
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- CN106047262B CN106047262B CN201610529832.1A CN201610529832A CN106047262B CN 106047262 B CN106047262 B CN 106047262B CN 201610529832 A CN201610529832 A CN 201610529832A CN 106047262 B CN106047262 B CN 106047262B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- 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
- C08G18/4202—Two or more polyesters of different physical or chemical nature
-
- 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
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
-
- 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
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
A kind of reflective preparation process for taking polyurethane resin composite glue, it is characterized in that the following steps are included: 1) synthesizing polyalcohol by decanedioic acid as acid, sub-fraction decanedioic acid is replaced using M-phthalic acid again, the polyalcohol of synthesis is named as PSI, molecular weight 1000；2) polyalcohol of the synthesis based on adipic acid and decanedioic acid names PSA, molecular weight 3000；3) after 70 DEG C sufficiently melt, investment chain extender antioxidant starts to stir investment polyalcohol PSI and polyalcohol PSA.Resin compounded glue made from the reflective preparation process for taking polyurethane resin composite glue of the invention will make clothing high temperature resistant water washing with super strength for bonding fabric and reflectorized material, and after being bonded.
Description
Technical field
The present invention relates to technical field of textile fabric, especially a kind of reflective preparation for taking polyurethane resin composite glue
Technique.
Background technique
Reflective clothes are to be embedded in clothes using reflectorized material or vest main portions are made for night or bad
Personal security's articles under weather, preferably protect staff in outside work.It is suitble to road crews, traffic road administration
Department, road commanding, police, cleaner etc. use, and height is reflective to be played the role of warning eye-catching, the peace of protection staff
Entirely.
The reflective polyurethane resin taken is that composite glue is used to bond fabric and reflectorized material, and to make clothing after being bonded
Object high temperature resistant with super strength and water-wash resistance.Existing market existing product is difficult to reach this performance indicator well, thus
Affect the security performance of reflective clothes.
Summary of the invention
The purpose of the present invention is to provide a kind of reflective preparation processes for taking polyurethane resin composite glue, anti-to meet
High temperature resistant needed for light takes composite glue and wash durability requirement.
The technical scheme is that
A kind of reflective preparation process for taking polyurethane resin composite glue, comprising the following steps:
1) polyalcohol is synthesized as acid by decanedioic acid, and uses the M-phthalic acid to replace sub-fraction decanedioic acid,
The polyalcohol of synthesis is named as PSI, molecular weight 1000；
2) polyalcohol of the synthesis based on adipic acid and decanedioic acid names PSA, molecular weight 3000；
3) after 70 DEG C sufficiently melt, investment chain extender, antioxidant start to stir investment polyalcohol PSI and polyalcohol PSA；
4) Toluene-2,4-diisocyanate, 4- diisocyanate are put into again, temperature is set in 70~80 DEG C, 1~2h is reacted, and put into solvent,
Because solvent temperature decline is added, when reaching 70 degree, the catalyst of investment and weight polyurethane ratio 0.05-0.1%, completely reaction hold
Or remaining isocyanate group；
5) methyl diphenylene diisocyanate 75%-85% is put into again, hereafter, after 20min puts into a diphenylmethyl again
Alkane diisocyanate reaches target viscosities stopping；
6) epoxy radicals silicone hydride for containing Si group is added as sticker, dosage is 0.5%~1%；
7) terminator is then added, auxiliary agent stabilizer is added after stable reaction；It finally draws a design and carries out high temperature washing test.
Solvent is that perhaps ethyl acetate catalyst is organic tin catalyst or has for acetone, butanone in the step 4)
Machine bismuth class catalyst.
The terminator is short chain alcohol amine, and auxiliary agent stabilizer is weak acid.
The specific steps of step 1) the synthesis polyalcohol PSI are as follows:
Binary acid, small molecule dihydric alcohol are put into, melts and is stirred to react 3 to 4 hours under the conditions of 120 DEG C to 150 DEG C, reach
After target water yield, be warming up to 160 DEG C to 200 DEG C, the reaction was continued reach within 3 to 4 hours target water yield after, be warming up to 220
DEG C, it reacts 2.5-3.5 hours, heavy metal category class catalyst is added, then react 0.5 to 1 hour, vacuumizes, intensity is incremented by successively,
It is finally 0.1MPa, reaching react after target hydroxyl value, acid value terminates, acquisition polyalcohol PSI.
The specific steps of step 2) the synthesis polyalcohol PSA are as follows:
Binary acid, small molecule dihydric alcohol are put into, melts and is stirred to react 3 to 4 hours under the conditions of 120 DEG C to 150 DEG C, reach
After target water yield, be warming up to 160 DEG C to 200 DEG C, the reaction was continued reach within 3 to 4 hours target water yield after, be warming up to 220
DEG C, it reacts 2.5-3.5 hours, heavy metal category class catalyst is added, then react 0.5 to 1 hour, vacuumizes, intensity is incremented by successively,
It is finally 0.1MPa, reaching react after target hydroxyl value, acid value terminates, acquisition polyalcohol PSA.
The beneficial effects of the present invention are:
Resin compounded glue made from the reflective preparation process for taking polyurethane resin composite glue of the invention, for gluing
Fabric and reflectorized material are tied, and to make clothing high temperature resistant water washing with super strength after being bonded.It is of the invention it is reflective take it is poly-
The preparation process of urethane resin compounded glue makes polyurethane have stronger hydrolytic resistance, and required as composite glue institute
Strong cohesive property and weatherability, in addition, the reflective preparation process for taking polyurethane resin composite glue of the invention tree obtained
Rouge is soft, is suitably applied on clothes, has preferable feel.Polyurethane of the invention will be combined well with reflectorized material,
It will not influence the gloss of reflectorized material.
Detailed description of the invention
Fig. 1 is process flow chart of the invention.
Specific embodiment
The invention will be further described below in conjunction with the accompanying drawings:
Process flow chart is as shown in Figure 1.
A kind of reflective preparation process for taking polyurethane resin composite glue, comprising the following steps:
1) polyalcohol is synthesized as acid by decanedioic acid, and uses the M-phthalic acid to replace sub-fraction decanedioic acid,
The polyalcohol of synthesis is named as PSI, molecular weight 1000；
2) polyalcohol of the synthesis based on adipic acid and decanedioic acid names PSA, molecular weight 3000；
3) after 70 DEG C sufficiently melt, investment chain extender, antioxidant start to stir investment polyalcohol PSI and polyalcohol PSA；
4) Toluene-2,4-diisocyanate, 4- diisocyanate are put into again, temperature is set in 70~80 DEG C, 1~2h is reacted, and put into solvent,
Because solvent temperature decline is added, when reaching 70 degree, the catalyst of investment and weight polyurethane ratio 0.05-0.1%, completely reaction hold
Or remaining isocyanate group；
5) methyl diphenylene diisocyanate 75%-85% is put into again, hereafter, after 20min puts into a diphenylmethyl again
Alkane diisocyanate reaches target viscosities stopping；
6) epoxy radicals silicone hydride 9041 containing Si group is added and is used as sticker, dosage is 0.5%~1%；
7) terminator is then added, auxiliary agent stabilizer is added after stable reaction；It finally draws a design and carries out high temperature washing test.
Solvent is that perhaps ethyl acetate catalyst is organic tin catalyst or has for acetone, butanone in the step 4)
Machine bismuth class catalyst.
The terminator is short chain alcohol amine, and auxiliary agent stabilizer is weak acid.
The specific steps of step 1) the synthesis polyalcohol PSI are as follows:
Binary acid, small molecule dihydric alcohol are put into, melts and is stirred to react 3 to 4 hours under the conditions of 120 DEG C to 150 DEG C, reach
After target water yield, be warming up to 160 DEG C to 200 DEG C, the reaction was continued reach within 3 to 4 hours target water yield after, be warming up to 220
DEG C, it reacts 2.5-3.5 hours, heavy metal category class catalyst is added, then react 0.5 to 1 hour, vacuumizes, intensity is incremented by successively,
It is finally 0.1MPa, reaching react after target hydroxyl value, acid value terminates, acquisition polyalcohol PSI.
The specific steps of step 2) the synthesis polyalcohol PSA are as follows:
Binary acid, small molecule dihydric alcohol are put into, melts and is stirred to react 3 to 4 hours under the conditions of 120 DEG C to 150 DEG C, reach
After target water yield, be warming up to 160 DEG C to 200 DEG C, the reaction was continued reach within 3 to 4 hours target water yield after, be warming up to 220
DEG C, it reacts 2.5-3.5 hours, heavy metal category class catalyst is added, then react 0.5 to 1 hour, vacuumizes, intensity is incremented by successively,
It is finally 0.1MPa, reaching react after target hydroxyl value, acid value terminates, acquisition polyalcohol PSA.
One, the present invention answer market customer requirement exploitation it is a it is reflective take polyurethane resin, this resin be composite glue use
To make clothing high temperature resistant water washing with super strength in bonding fabric and reflectorized material, and after being bonded.Reach the target just
It needs to take into account the following
1) just need polyurethane that there is stronger hydrolytic resistance because washing time is longer
2) must have very strong caking property again as composite glue
3) because being high temperature washing, polyurethane has to have weatherability,
4) because applying institute's feel on clothes partially soft
5) polyurethane will be combined well with reflectorized material, cannot influence the gloss etc. of reflectorized material
For the above several points, need to solve following key problem in technology point
1) high temperature resistant water washing:
Water-fastness that resin is required to have very strong hydrolytic resistance, polyether alcohol effect is relatively good.It is poly- in terms of high temperature resistant
Ester effect is relatively good.Which forms contradictions.
2) caking property feel:
Because feel wants soft, soft segment chain content is more when synthesis, and molecular mass is also relatively low, such words caking property with regard to poor,
This just needs bridging agent.Bridging agent is usually NCO there are three end contains, and general reflectorized material is difficult in conjunction with NCO group.
3) reflectorized material gloss reflective function:
The performance of reflectorized material is kept, the solvent that just polarity must be selected weaker, and the weak dissolubility of solvent polarity is just low,
Raw material selection aspect is just narrow.
Two, solution and technological innovation；
1) the rarely found polyalcohol in synthesis market
Polyester polyol currently on the market, polyether alcohol are difficult to meet fire resistant water resistant, we are by continuous
Experimental selection decanedioic acid synthesize polyalcohol as acid because decanedioic acid is water-fast with respect to the big chain length of molecular weight for adipic acid
It is much better to solve performance, the resin of synthesis is polyesters again, and high temperature resistant can be with.M-phthalic acid is used to replace again to increase caking property
Sub-fraction decanedioic acid.The polyalcohol name PSI. of synthesis is because use weak polar solvent, and decanedioic acid point in polyalcohol
Subchain is long and M-phthalic acid contains phenyl ring, so the alcohol molecular weight of synthesis cannot be too big.Select 1000 molecular weight.1000 molecules
The alcohol synthesis of polyurethane intensity of amount is larger, and feel is too hard.
The polyalcohol PSA based on adipic acid and decanedioic acid has been synthesized thus, and molecular weight 3000. reconciles soft or hard.
2) increase and studied with reflectorized material caking property auxiliary agent
Different types of sticker is tried out, finally the selected epoxy radicals silicone hydride containing Si group, dosage is 0.5%~1%
Left and right is advisable
3. the major technique and economic indicator that reach.
Technical indicator:
Three, it researchs and develops test method and uses technology (technique) route
Reaction principle:
With two end NCO with the substance of OH reacting under certain condition, be polyurethane polymerization reaction.Such poly- ammonia
The physical property of the machinery such as elastic force, wearability, weatherability of ester resin is more outstanding than natural rubber.
Experimental method: polyalcohol PSI and PSA are selected by continuous regulation experiment, carbimide selects TDI with MDI's
Combination, for chain extender aspect by comparative experiments selection CHDM because it is containing symmetrical unimpeded primary hydroxyl, thermostabilization is more outstanding
And the balance with good hardness and flexibility.,
Process route explanation:
PSI is put into, after 70 DEG C sufficiently melt, investment chain extender antioxidant starts to stir PSA.TDI temperature is put into again to set
70~80 DEG C are scheduled on, 1~2h is reacted, investment solvent is because being added solvent temperature decline, when reaching 70 degree, puts into weight polyurethane ratio
The catalyst of 0.05-0.1% reacts remaining isocyanate group completely.MDI is put into again and gets over 80% or so, hereafter, about
20min puts into a MDI (dosage is answered depending on response situation), reaches target viscosities stopping.Then terminator is added.It is steady wait react
Auxiliary agent stabilizer is added after fixed.It finally draws a design and carries out high temperature washing test.
The above-described embodiments are merely illustrative of preferred embodiments of the present invention, not to structure of the invention
Think and range is defined, under the premise of not departing from design concept of the present invention, ordinary engineering and technical personnel is to this hair in this field
The all variations and modifications that bright technical solution is made should all fall into protection scope of the present invention, the claimed skill of the present invention
Art content is all described in the claims.
Claims (1)
1. a kind of reflective preparation process for taking polyurethane resin composite glue, it is characterized in that the following steps are included:
1) polyalcohol is synthesized as acid by decanedioic acid, and uses the M-phthalic acid to replace sub-fraction decanedioic acid, synthesis
Polyalcohol be named as PSI, molecular weight 1000；
2) polyalcohol of the synthesis based on adipic acid and decanedioic acid names PSA, molecular weight 3000；
3) after 70 DEG C sufficiently melt, investment chain extender, antioxidant start to stir investment polyalcohol PSI and polyalcohol PSA；
4) Toluene-2,4-diisocyanate, 4- diisocyanate are put into again, and temperature is set in 70~80 DEG C, 1~2h is reacted, and put into solvent, because adding
Enter solvent temperature decline, when reaching 70 degree, the catalyst of investment and weight polyurethane ratio 0.05-0.1%, by remaining isocyanic acid
Ester group reacts completely；
5) methyl diphenylene diisocyanate 75%-85% is put into again, hereafter, after 20min puts into a diphenyl methane two again
Isocyanates reaches target viscosities stopping；
6) terminator is then added, the epoxy radicals silicone hydride for containing Si group is added as sticker, dosage is 0.5%~1%；
7) auxiliary agent stabilizer, is added after stable reaction；It finally draws a design and carries out high temperature washing test；
Solvent is that perhaps ethyl acetate catalyst is organic tin catalyst or organo-bismuth for acetone, butanone in the step 4)
Class catalyst；The terminator is short chain alcohol amine, and auxiliary agent stabilizer is weak acid；
The specific steps of step 1) the synthesis polyalcohol PSI are as follows: investment binary acid, small molecule dihydric alcohol, at 120 DEG C to 150
Fusing is stirred to react 3 to 4 hours under the conditions of DEG C, after reaching target water yield, is warming up to 160 DEG C to 200 DEG C, and the reaction was continued 3 to 4
After hour reaches target water yield, 220 DEG C are warming up to, is reacted 2.5-3.5 hours, heavy metal classes catalyst is added, then react
It 0.5 to 1 hour, vacuumizes, it is finally 0.1MPa that intensity is incremented by successively, and reaching to react after target hydroxyl value, acid value terminates, and is obtained
Polyalcohol PSI；
The specific steps of step 2) the synthesis polyalcohol PSA are as follows: investment binary acid, small molecule dihydric alcohol, at 120 DEG C to 150
Fusing is stirred to react 3 to 4 hours under the conditions of DEG C, after reaching target water yield, is warming up to 160 DEG C to 200 DEG C, and the reaction was continued 3 to 4
After hour reaches target water yield, 220 DEG C are warming up to, is reacted 2.5-3.5 hours, heavy metal classes catalyst is added, then react
It 0.5 to 1 hour, vacuumizes, it is finally 0.1MPa that intensity is incremented by successively, and reaching to react after target hydroxyl value, acid value terminates, and is obtained
Polyalcohol PSA.
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| CN201610529832.1A CN106047262B (en) | 2016-07-06 | 2016-07-06 | The reflective preparation process for taking polyurethane resin composite glue |
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| CN201610529832.1A CN106047262B (en) | 2016-07-06 | 2016-07-06 | The reflective preparation process for taking polyurethane resin composite glue |
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| CN107081686A (en) * | 2017-05-27 | 2017-08-22 | 江苏省江南新型复合研磨材料及制品工程技术研究中心有限公司 | A kind of high-strength polyester gauze cloth base handling process |
| CN107338017B (en) * | 2017-08-16 | 2020-08-11 | 浙江夜光明光电科技股份有限公司 | Polyurethane adhesive for high-temperature-resistant washing reflective material |
| CN108165214A (en) * | 2018-01-03 | 2018-06-15 | 浙江恒劲树脂有限公司 | A kind of reflective preparation process for taking polyurethane resin composite glue |
| CN115806794A (en) * | 2022-08-15 | 2023-03-17 | 杭州星华反光材料股份有限公司 | Preparation method and application of polyurethane adhesive with excellent washing resistance |
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| CN105295815B (en) * | 2015-11-11 | 2019-01-25 | 上海康达化工新材料股份有限公司 | A kind of Reflection fabric reaction type polyurethane hot-melt adhesive and preparation method thereof |
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