CN110643007A - 一种酚醛树脂木材增韧胶黏剂的制备方法 - Google Patents
一种酚醛树脂木材增韧胶黏剂的制备方法 Download PDFInfo
- Publication number
- CN110643007A CN110643007A CN201911095098.2A CN201911095098A CN110643007A CN 110643007 A CN110643007 A CN 110643007A CN 201911095098 A CN201911095098 A CN 201911095098A CN 110643007 A CN110643007 A CN 110643007A
- Authority
- CN
- China
- Prior art keywords
- reaction
- phenol
- adhesive
- phenolic resin
- wood
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 68
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 68
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 229920001568 phenolic resin Polymers 0.000 title claims abstract description 56
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 56
- 239000002023 wood Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000001336 alkenes Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 29
- 238000004321 preservation Methods 0.000 claims abstract description 25
- 238000002156 mixing Methods 0.000 claims abstract description 24
- 230000002378 acidificating effect Effects 0.000 claims abstract description 22
- 239000000243 solution Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 12
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 230000004913 activation Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 12
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 239000000047 product Substances 0.000 abstract description 23
- 150000002989 phenols Chemical class 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 11
- 238000005804 alkylation reaction Methods 0.000 abstract description 10
- 239000003377 acid catalyst Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000007599 discharging Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000003213 activating effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- -1 phenol compound Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000013638 trimer Substances 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
-
- 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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201911095098.2A CN110643007B (zh) | 2019-11-11 | 2019-11-11 | 一种酚醛树脂木材增韧胶黏剂的制备方法 |
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CN201911095098.2A CN110643007B (zh) | 2019-11-11 | 2019-11-11 | 一种酚醛树脂木材增韧胶黏剂的制备方法 |
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CN110643007A true CN110643007A (zh) | 2020-01-03 |
CN110643007B CN110643007B (zh) | 2022-08-02 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112552472A (zh) * | 2020-11-13 | 2021-03-26 | 山东京博木基材料有限公司 | 一种水溶性增韧改性酚醛树脂的制备方法 |
CN113801280A (zh) * | 2021-11-16 | 2021-12-17 | 北京玻钢院复合材料有限公司 | 一种适用于热熔预浸工艺的烷基酚改性酚醛树脂及其制备方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1278582A (en) * | 1968-08-20 | 1972-06-21 | Bp Chem Int Ltd | Phenolic laminating resins |
US3703494A (en) * | 1971-03-01 | 1972-11-21 | Monsanto Co | Resole varnishes wherein phenol is alkylated with a dicyclopentadiene-containing mixture and then condensed with formaldehyde to produce the resole |
EP0026975A1 (en) * | 1979-09-08 | 1981-04-15 | BP Chemicals Limited | Process for the production of phenolic resins |
CN1196069A (zh) * | 1995-07-12 | 1998-10-14 | 佐治亚-太平洋树脂公司 | 用芳烷基化反应制备酚醛聚合物 |
CN101239889A (zh) * | 2008-02-26 | 2008-08-13 | 江苏工业学院 | 一种含有烷基苯酚产物的反应液的制备方法 |
CN102604018A (zh) * | 2012-03-08 | 2012-07-25 | 陈曦 | 一种烷基苯酚甲醛树脂的制备方法 |
US20140080965A1 (en) * | 2012-09-17 | 2014-03-20 | Sino Legend (Zhangjiagang) Chemical Co. Ltd. | Alkyl Phenolic Resin and Method of Preparation Thereof |
CN105566590A (zh) * | 2016-01-29 | 2016-05-11 | 河北德大化工有限公司 | 一种改性酚醛树脂的制备方法及其应用 |
CN109880031A (zh) * | 2018-12-07 | 2019-06-14 | 山东阳谷华泰化工股份有限公司 | 一种混合烷基苯酚-甲醛树脂橡胶增粘剂的制备方法 |
-
2019
- 2019-11-11 CN CN201911095098.2A patent/CN110643007B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1278582A (en) * | 1968-08-20 | 1972-06-21 | Bp Chem Int Ltd | Phenolic laminating resins |
US3703494A (en) * | 1971-03-01 | 1972-11-21 | Monsanto Co | Resole varnishes wherein phenol is alkylated with a dicyclopentadiene-containing mixture and then condensed with formaldehyde to produce the resole |
EP0026975A1 (en) * | 1979-09-08 | 1981-04-15 | BP Chemicals Limited | Process for the production of phenolic resins |
CN1196069A (zh) * | 1995-07-12 | 1998-10-14 | 佐治亚-太平洋树脂公司 | 用芳烷基化反应制备酚醛聚合物 |
CN101239889A (zh) * | 2008-02-26 | 2008-08-13 | 江苏工业学院 | 一种含有烷基苯酚产物的反应液的制备方法 |
CN102604018A (zh) * | 2012-03-08 | 2012-07-25 | 陈曦 | 一种烷基苯酚甲醛树脂的制备方法 |
US20140080965A1 (en) * | 2012-09-17 | 2014-03-20 | Sino Legend (Zhangjiagang) Chemical Co. Ltd. | Alkyl Phenolic Resin and Method of Preparation Thereof |
CN105566590A (zh) * | 2016-01-29 | 2016-05-11 | 河北德大化工有限公司 | 一种改性酚醛树脂的制备方法及其应用 |
CN109880031A (zh) * | 2018-12-07 | 2019-06-14 | 山东阳谷华泰化工股份有限公司 | 一种混合烷基苯酚-甲醛树脂橡胶增粘剂的制备方法 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112552472A (zh) * | 2020-11-13 | 2021-03-26 | 山东京博木基材料有限公司 | 一种水溶性增韧改性酚醛树脂的制备方法 |
CN112552472B (zh) * | 2020-11-13 | 2022-08-16 | 山东京博木基材料有限公司 | 一种水溶性增韧改性酚醛树脂的制备方法 |
CN113801280A (zh) * | 2021-11-16 | 2021-12-17 | 北京玻钢院复合材料有限公司 | 一种适用于热熔预浸工艺的烷基酚改性酚醛树脂及其制备方法 |
CN113801280B (zh) * | 2021-11-16 | 2022-02-08 | 北京玻钢院复合材料有限公司 | 一种适用于热熔预浸工艺的烷基酚改性酚醛树脂及其制备方法 |
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