CN112898562A - Polyamide polyamine-glycidyl ether resin cylinder-sticking agent and preparation method and application thereof - Google Patents
Polyamide polyamine-glycidyl ether resin cylinder-sticking agent and preparation method and application thereof Download PDFInfo
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- CN112898562A CN112898562A CN202110075766.6A CN202110075766A CN112898562A CN 112898562 A CN112898562 A CN 112898562A CN 202110075766 A CN202110075766 A CN 202110075766A CN 112898562 A CN112898562 A CN 112898562A
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- Prior art keywords
- glycidyl ether
- polyamide polyamine
- acid
- ether resin
- resin cylinder
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 49
- 229920002647 polyamide Polymers 0.000 title claims abstract description 49
- 229920005989 resin Polymers 0.000 title claims abstract description 37
- 239000011347 resin Substances 0.000 title claims abstract description 37
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 238000010438 heat treatment Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000853 adhesive Substances 0.000 claims abstract description 19
- 230000001070 adhesive effect Effects 0.000 claims abstract description 19
- 229920000768 polyamine Polymers 0.000 claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004132 cross linking Methods 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- -1 alkenyl amine Chemical class 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000007789 sealing Methods 0.000 claims abstract description 7
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 6
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 6
- 239000001361 adipic acid Substances 0.000 claims description 6
- 235000011037 adipic acid Nutrition 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 4
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 2
- LUSCNZBJFBNVDT-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxy)cyclohexyl]oxymethyl]oxirane Chemical compound C1OC1COC1(OCC2OC2)CCCCC1 LUSCNZBJFBNVDT-UHFFFAOYSA-N 0.000 claims description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 claims description 2
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 claims description 2
- KTLIZDDPOZZHCD-UHFFFAOYSA-N 3-(2-aminoethylamino)propan-1-ol Chemical compound NCCNCCCO KTLIZDDPOZZHCD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000002081 enamines Chemical class 0.000 claims description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 claims description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 18
- 238000000576 coating method Methods 0.000 abstract description 18
- 238000005507 spraying Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000003756 stirring Methods 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 238000011049 filling Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/06—Polyamides derived from polyamines and polycarboxylic acids
Abstract
The invention discloses a polyamide polyamine-glycidyl ether resin cylinder-sticking agent, a preparation method and application thereof. The cylinder sticking agent of polyamide polyamine-glycidyl ether resin is prepared by the steps of firstly carrying out polycondensation reaction on alkenyl amine derivatives and dibasic acid under normal pressure, then continuing the polycondensation reaction under the vacuum condition until the molecular weight is not increased any more, and adding water to form an aqueous solution of a polyamide polyamine intermediate. Cooling, adding glycidyl ether substances, sealing the reaction kettle, heating to carry out crosslinking reaction, adding organic acid to terminate the reaction, and adding water to dilute to obtain the polyamide polyamine-glycidyl ether resin cylinder-sticking agent. The polyamide polyamine-glycidyl ether resin cylinder adhesive has good water solubility and low viscosity, and a drying cylinder coating formed by spraying has good uniformity.
Description
Technical Field
The invention belongs to the technical field of papermaking additives, and relates to a cylinder sticking agent which is sprayed on a drying cylinder to help paper sheet wrinkling during production of crepe paper, in particular to a polyamide polyamine-glycidyl ether resin cylinder sticking agent, and a preparation method and application thereof.
Background
When the crepe paper is produced, the paper passes through a drying cylinder for drying, and needs to generate strong impact with a scraper to generate wrinkles so as to improve the properties of softness, water absorption, bulk and the like of the paper and obtain good hand feeling. The creping process requires a suitable bond between the sheet and the dryer, and for paper machines with higher speeds, the natural bond between the sheet and the dryer alone is insufficient to form the desired crepe, requiring adjustment with dryer coating aids (including cylinder stickers, strippers, and modifiers) to achieve flexible control of the creping process. The coating auxiliary agent is improperly used or has poor performance, which not only can cause great influence on the quality of paper, but also can cause the problems of pinholes, dead lines, broken holes and the like, and even can cause the cutter jump to cause the damage of a drying cylinder. Among them, the most critical to the establishment and adjustment of the coating is the cylinder adhesive, but the current cylinder adhesive has the problems of not being compatible in terms of performance, such as adhesion, flexibility, water solubility, uniformity and durability.
Compared with substitutes such as polyvinyl alcohol, polyvinyl acetate, polyacrylamide, polyether and the like, the polyamide polyamine-epichlorohydrin series cylinder-sticking agent has obvious comprehensive performance advantages, and therefore becomes the cylinder-sticking agent which is most widely applied in commerce. The polyamide polyamine-epichlorohydrin cylinder-sticking agent is thermosetting resin which takes polyamide polyamine as a main chain and takes epichlorohydrin as a cross-linking agent, and is also called PAE resin and PAE cylinder-sticking agent. The PAE resin has good flexibility and water solubility; the viscosity is low and the leveling is easy under the water environment, so that the uniformity is realized; one epichlorohydrin molecule can be connected with 2-3 polyamide polyamine molecules, so that the molecular weight of the polymer is increased, the number of terminal groups is increased, and the adhesive force is stronger.
The irreversible crosslinking reaction provides good adhesion to the PAE cylinder adhesive and also results in less than ideal durability. PAE stickers tend to build up on the dryer surface, crosslinking continues to raise the polymer molecular weight indefinitely, the coating hardens over time, causing blade rattle, partial coating may crack and fall off, causing sheet holes and even sheet breaks, and the coating has to be rebuilt.
Many researchers have carried out molecular structure modification or blending based on PAE resins in an attempt to overcome the disadvantage of easy hardening of PAE. For example, patent CN201180024895 uses reactive auxiliary agent with stripping property formed by reaction of polyalkylene polyamine and electrophilic reagent to modify PAE to prepare the cylinder sticking agent, patent CN201280003852 mixes PAE and polyvinyl alcohol copolymer with carboxylic ester or sulfonic ester repeating units to prepare the cylinder sticking agent, patent CN201610814690 inserts acrylic acid monomer into polyamide polyamine molecules and polymerizes to obtain polyamide polyamine with higher molecular weight, and then crosslinks with epichlorohydrin to obtain the cylinder sticking agent.
However, the unreacted epichlorohydrin in the PAE resin can be absorbed by human body and is harmful to human health, and the chloropropanol as the hydrolysis product is more harmful. National standard GB5009.191-2016 specifies the allowable content of chloropropanol in food products, including DCP (1, 3-dichloro-2-propanol), MCPD (3-chloro-1, 2-propanediol). The national standard GB/T36420-2018 specifies the limited content of absorbable halides in paper and paper products for daily use, including epichlorohydrin, DCP and MCPD, but does not provide a detection method.
In addition, the irreversible crosslinking reaction provides good adhesion to the PAE cylinder adhesive, which also results in less than desirable durability. PAE stickers tend to build up on the dryer surface, crosslinking continues to raise the polymer molecular weight indefinitely, the coating hardens over time, causing blade rattle, partial coating may crack and fall off, causing sheet holes and even sheet breaks, and the coating has to be rebuilt.
Furthermore, because the PAE has certain crosslinking property at normal temperature, the higher the solid content is, the more easily the PAE is gelled due to crosslinking, the solid content of the commercially available jar-sticking agent is generally below 15 percent and not more than 40 percent at most, and the packaging, storage and transportation cost is higher.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a polyamide polyamine-glycidyl ether resin cylinder sticking agent which has high solid content and is easy to stably store, and a preparation method and application thereof.
Therefore, the invention adopts the following technical scheme: a method for preparing a polyamide polyamine-glycidyl ether resin cylinder-sticking agent comprises the following steps:
firstly, performing polycondensation reaction on an alkenyl amine derivative and dibasic acid at normal pressure and at the temperature of 130-200 ℃, then continuing the polycondensation reaction at the temperature of 150-240 ℃ and under the absolute pressure of 1-5000Pa until the molecular weight is not increased any more, and adding water to form an aqueous solution of a polyamide polyamine intermediate;
cooling the aqueous solution of the polyamide polyamine intermediate to 0-20 ℃, adding glycidyl ether, sealing the reaction kettle, heating to 10-70 ℃ for crosslinking reaction for 1-10 hours, finally adding organic acid to terminate the reaction, and adding water to dilute to obtain the polyamide polyamine-glycidyl ether resin cylinder sticking agent with the solid content of 5-30%.
The invention avoids the use of epoxy chloropropane.
The enamine derivative is selected from one or more of diethylenetriamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, hydroxyethyl ethylenediamine, hydroxypropyl ethylenediamine, aminoethyl aminopropylamine and dipropylenetriamine.
Further, the dibasic acid is selected from one or a mixture of more than two of malonic acid, succinic acid, glutaric acid, adipic acid, dodecanedioic acid, succinic acid, isophthalic acid and terephthalic acid.
Further, the glycidyl ether is selected from one or a mixture of more than two of 1, 4-butanediol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, bisphenol A diglycidyl ether, resorcinol diglycidyl ether, cyclohexanediol diglycidyl ether, neopentyl glycol diglycidyl ether and ethylene glycol diglycidyl ether.
Further, the organic acid is selected from one or a mixture of more than two of formic acid, acetic acid, propionic acid and benzoic acid.
Further, the mol ratio of the alkenyl amine derivative to the dibasic acid to the glycidyl ether is 1.0: 0.9-1.1: 0.01-0.8.
Further, the mol ratio of the alkenyl amine derivative to the dibasic acid to the glycidyl ether is 1.0: 0.9-1.1: 0.2-0.6.
The invention also provides the polyamide polyamine-glycidyl ether resin cylinder adhesive prepared by the preparation method.
The invention also provides application of the polyamide polyamine-glycidyl ether resin cylinder adhesive, and the polyamide polyamine-glycidyl ether resin cylinder adhesive is sprayed on a drying cylinder to help paper sheet wrinkling when crepe paper is produced.
The invention has the following beneficial effects: the polyamide polyamine-glycidyl ether resin has higher initial molecular weight and good initial adhesive force when being used as a cylinder sticking agent; the glycidyl ether is used as a cross-linking agent, so that the drying cylinder coating can keep a long-time and slow cross-linking speed, the coating cannot become very hard in the period, and the bonding property lasts for a long time; the glycidyl ether has better water solubility than epoxy chloropropane, the obtained polyamide polyamine-glycidyl ether resin cylinder bonding agent has good water solubility and low viscosity, and a drying cylinder coating formed by spraying has good uniformity; the molecular chain length of the glycidyl ether compared to epichlorohydrin makes the polyamide polyamine-glycidyl ether resin much softer than the polyamide polyamine-epichlorohydrin resin.
Detailed Description
The technology of the present invention will be described in detail below with reference to specific embodiments. It should be understood that the following detailed description is only for the purpose of assisting those skilled in the art in understanding the present invention, and is not intended to limit the present invention.
Example 1
In a stainless steel reaction kettle with the conditions of weighing, jacket heating, temperature reduction, nitrogen protection, stirring, temperature indication, pressure indication, feeding and the like, nitrogen is replaced, stirring is started, the temperature is increased to 140 ℃, and the vacuum is pumped to 5kPa and kept for 15 minutes. Adding 146g (1mol) of adipic acid, charging nitrogen to slight positive pressure, dropwise adding 113.3g (1.1mol) of diethylenetriamine, heating to 140 ℃, stirring and mixing for 2 hours, then heating to 10 ℃ per hour until 180 ℃, and preserving heat for 2 hours. Starting a vacuum system, gradually vacuumizing to the absolute pressure of 100Pa, and keeping the temperature for 2 hours. Stopping heating, filling nitrogen to micro positive pressure, adding 453.4g of hot deionized water to dilute the reaction materials until the solid content is 33 percent, namely the aqueous solution of the polyamide polyamine intermediate. Cooling the aqueous solution of the polyamide polyamine intermediate to 10 ℃, dropwise adding 70g (0.4mol) of ethylene glycol diglycidyl ether, sealing the reactor, heating to 15 ℃, reacting for 3 hours, adding 4.6g (0.1mol) of formic acid to terminate the reaction, and adding 2155g of deionized water to obtain the polyamide polyamine-glycidyl ether resin cylinder sticking agent A with the solid content of 10%.
Example 2
In a stainless steel reaction kettle with the conditions of weighing, jacket heating, temperature reduction, nitrogen protection, stirring, temperature indication, pressure indication, feeding and the like, nitrogen is replaced, stirring is started, the temperature is increased to 140 ℃, and the vacuum is pumped to 5kPa and kept for 15 minutes. Adding 146g (1mol) of adipic acid, charging nitrogen to slight positive pressure, dropwise adding 113.3g (1.1mol) of diethylenetriamine, heating to 140 ℃, stirring and mixing for 2 hours, then heating to 10 ℃ per hour until 180 ℃, and preserving heat for 2 hours. Starting a vacuum system, gradually vacuumizing to the absolute pressure of 100Pa, and keeping the temperature for 2 hours. Stopping heating, filling nitrogen to micro positive pressure, adding 453.4g of hot deionized water to dilute the reaction materials until the solid content is 33 percent, namely the aqueous solution of the polyamide polyamine intermediate. Cooling the aqueous solution of the polyamide polyamine intermediate to 10 ℃, dropwise adding 8.7g (0.05mol) of ethylene glycol diglycidyl ether, sealing the reactor, heating to 15 ℃, reacting for 5 hours, adding 6g (0.15mol) of formic acid to terminate the reaction, and adding 2070g of deionized water to obtain the polyamide polyamine-glycidyl ether resin cylinder sticking agent B with the solid content of 10%.
Example 3
In a stainless steel reaction kettle with the conditions of weighing, jacket heating, temperature reduction, nitrogen protection, stirring, temperature indication, pressure indication, feeding and the like, nitrogen is replaced, stirring is started, the temperature is increased to 140 ℃, and the vacuum is pumped to 5kPa and kept for 15 minutes. Adding 146g (1mol) of adipic acid, charging nitrogen to slight positive pressure, dropwise adding 113.3g (1.1mol) of diethylenetriamine, heating to 140 ℃, stirring and mixing for 2 hours, then heating to 10 ℃ per hour until 180 ℃, and preserving heat for 2 hours. Starting a vacuum system, gradually vacuumizing to the absolute pressure of 100Pa, and keeping the temperature for 2 hours. Stopping heating, filling nitrogen to micro positive pressure, adding 453.4g of hot deionized water to dilute the reaction materials until the solid content is 33 percent, namely the aqueous solution of the polyamide polyamine intermediate. Cooling the aqueous solution of the polyamide polyamine intermediate to 10 ℃, dropwise adding 136g (0.4mol) of bisphenol A diglycidyl ether, sealing the reactor, heating to 15 ℃, reacting for 5 hours, adding 4.6g (0.1mol) of formic acid to terminate the reaction, and adding 3200g of deionized water to obtain the polyamide polyamine-glycidyl ether resin cylinder sticking agent C with the solid content of 10%.
Comparative example 1
In a stainless steel reaction kettle with the conditions of weighing, jacket heating, temperature reduction, nitrogen protection, stirring, temperature indication, pressure indication, feeding and the like, nitrogen replacement is carried out, 146g (1mol) of adipic acid is added, nitrogen is filled to the micro positive pressure, 113.3g (1.1mol) of diethylenetriamine is dropwise added, the temperature is increased to 140 ℃, stirring and mixing are carried out for 2 hours, then the temperature is increased to 10 ℃ per hour until 180 ℃, and the temperature is kept for 2 hours. Starting a vacuum system, gradually vacuumizing to the absolute pressure of 100Pa, and keeping the temperature for 2 hours. Stopping heating, filling nitrogen to micro positive pressure, adding 453.4g of hot deionized water to dilute the reaction materials until the solid content is 33 percent, namely the aqueous solution of the polyamide polyamine intermediate. Cooling the aqueous solution of the polyamide polyamine intermediate to 25 ℃, dropwise adding 27.8g (0.3mol) of epichlorohydrin, sealing the reactor, heating to 30 ℃ for reaction for 3 hours, heating to 70 ℃ again for reaction for 2 hours, adding 4.6g (0.1mol) of formic acid to terminate the reaction, and adding 3200g of deionized water to obtain the polyamide polyamine-epichlorohydrin resin cylinder adhesive D with the solid content of 10%.
Comparative example 2
Selecting a commercially available polyamide polyamine-epichlorohydrin resin cylinder sticking agent E.
Test method
Molecular weight-viscosity. The viscosity of each cylinder-sticking agent was measured in cP at room temperature at 20 ℃ using a rotary viscometer, spindle No. 3, at 30 RPM. The higher the viscosity, the higher the molecular weight.
Adhesion-tensile strength. A polytetrafluoroethylene channel plate with a groove with the size of 50mm multiplied by 100mm is prepared by adding 5g of wood short fiber into the groove, uniformly spreading, dripping 10g of cylinder sticking agent prepared by the invention, placing in a 105 ℃ oven for drying for 30 minutes, taking out the channel plate, carefully taking down the whole coating when the coating is hot, standing and cooling to room temperature of 20 ℃, cutting out a sample strip with the width of 15mm by a cutter, and testing the tensile strength with a tensile machine with the unit of gf. The greater the tensile strength, the greater the adhesion.
Durability-adhesion rating. The stainless steel channel plate with 50mm 100mm groove is dropped with 10g of the cylinder sticking agent prepared by the invention, and then the channel plate is dried in a 105 ℃ oven for 120 minutes, taken out and cooled to room temperature of 20 ℃. The adhesion of the coating was tested with a hundred grid knife, see GB/T9286-98. The adhesive force is divided into 6 grades of 0-5, the incision of 0 grade is the smoothest, and the adhesive force is the best.
Durability-bond retention. A stainless steel cell plate having a groove of 50mm X100 mm in size, weighed WA at room temperature, WAs dropped with 10g of the jar-bonding agent prepared according to the present invention into the groove, and then dried in an oven at 105 ℃ for 60 minutes. 5g of wood staple fibers were scattered and spread evenly in the grooves in an oven and pressed for 1 minute with a stainless steel block weighing 1kg and having a bottom dimension of 48mm by 98 mm. And removing the steel block, turning the groove plate and slightly shaking to enable the unbonded wood short fibers to fall off fully. The trough plate was taken out, cooled to room temperature of 20 ℃ and weighed as WB. WB-WA is the total weight of the coating in g, the larger the value, the better the retention of the adhesion of the coating.
TABLE 1 Cylinder sticking agent test results
The specific embodiments described herein are merely illustrative of the spirit of the invention. Various modifications or additions may be made to the described embodiments or alternatives may be employed by those skilled in the art without departing from the spirit or ambit of the invention as defined in the appended claims.
Claims (9)
1. A method for preparing polyamide polyamine-glycidyl ether resin cylinder-sticking agent is characterized in that,
firstly, performing polycondensation reaction on an alkenyl amine derivative and dibasic acid at normal pressure and at the temperature of 130-200 ℃, then continuing the polycondensation reaction at the temperature of 150-240 ℃ and under the absolute pressure of 1-5000Pa until the molecular weight is not increased any more, and adding water to form an aqueous solution of a polyamide polyamine intermediate;
cooling the aqueous solution of the polyamide polyamine intermediate to 0-20 ℃, adding glycidyl ether, sealing the reaction kettle, heating to 10-70 ℃ for crosslinking reaction for 1-10 hours, finally adding organic acid to terminate the reaction, and adding water to dilute to obtain the polyamide polyamine-glycidyl ether resin cylinder sticking agent with the solid content of 5-30%.
2. The method of claim 1, wherein the enamine derivative is selected from the group consisting of diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hydroxyethylethylenediamine, hydroxypropylethylenediamine, aminoethylaminopropylamine, and dipropylenetriamine.
3. The method for preparing a polyamide polyamine-glycidyl ether resin cylinder adhesive as claimed in claim 1, wherein the dibasic acid is one or more selected from malonic acid, succinic acid, glutaric acid, adipic acid, dodecanedioic acid, succinic acid, isophthalic acid and terephthalic acid.
4. The method for preparing a polyamide polyamine-glycidyl ether resin cylinder adhesive according to claim 1, wherein the glycidyl ether is selected from one or a mixture of more than two of 1, 4-butanediol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, bisphenol A diglycidyl ether, resorcinol diglycidyl ether, cyclohexanediol diglycidyl ether, neopentyl glycol diglycidyl ether and ethylene glycol diglycidyl ether.
5. The method for preparing a polyamide polyamine-glycidyl ether resin cylinder-sticking agent according to claim 1, wherein the organic acid is one or a mixture of more than two of formic acid, acetic acid, propionic acid and benzoic acid.
6. The method for preparing a polyamide polyamine-glycidyl ether resin cylinder adhesive according to claim 1, wherein the molar ratio of the alkenyl amine derivative to the dibasic acid to the glycidyl ether is 1.0: 0.9-1.1: 0.01-0.8.
7. The process for preparing a cylinder stick of polyamide polyamine-glycidyl ether resin according to claim 1 or 6, wherein the molar ratio of the alkenyl amine derivative to the dibasic acid to the glycidyl ether is 1.0: 0.9-1.1: 0.2-0.6.
8. A polyamide polyamine-glycidyl ether resin cylinder adhesive characterized by being prepared by the method of any one of claims 1 to 7.
9. Use of a polyamidoamine-glycidyl ether resin cylinder adhesive for creping paper, characterized in that the polyamidoamine-glycidyl ether resin cylinder adhesive prepared by the method of any one of claims 1 to 7 is sprayed on a drying cylinder to help the creping of the paper sheet.
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