CA1164141A - Resine liquide de novolaque et produits derives - Google Patents

Resine liquide de novolaque et produits derives

Info

Publication number: CA1164141A
Authority: CA; Canada
Prior art keywords: novolak resin; resin; solvent; resulting; added
Prior art date: 1979-06-20
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.): Expired

Application number

CA000352555A

Other languages

English (en)

Inventor

Carl A. Rude

David D. Watson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Quaker Oats Co

Penn Specialty Chemicals Inc

Original Assignee

Quaker Oats Co

Priority date (The priority date 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 date listed.)

1979-06-20

Filing date

1980-05-23

Publication date

1984-03-20

1980-05-23 Application filed by Quaker Oats Co filed Critical Quaker Oats Co

1984-03-20 Application granted granted Critical

1984-03-20 Publication of CA1164141A publication Critical patent/CA1164141A/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 105
239000011347 resin Substances 0.000 title claims abstract description 105
229920003986 novolac Polymers 0.000 title claims abstract description 74
239000007788 liquid Substances 0.000 title claims abstract description 26
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims abstract description 100
239000002904 solvent Substances 0.000 claims abstract description 43
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 20
238000004519 manufacturing process Methods 0.000 claims abstract description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 36
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 21
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
150000001299 aldehydes Chemical class 0.000 claims description 17
239000011541 reaction mixture Substances 0.000 claims description 16
150000002576 ketones Chemical class 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
230000003472 neutralizing effect Effects 0.000 claims description 5
238000001816 cooling Methods 0.000 abstract description 18
239000000463 material Substances 0.000 abstract description 10
235000019628 coolness Nutrition 0.000 abstract 1
239000003701 inert diluent Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 37
238000012360 testing method Methods 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000002253 acid Substances 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229960004279 formaldehyde Drugs 0.000 description 5
235000019256 formaldehyde Nutrition 0.000 description 5
239000000047 product Substances 0.000 description 5
229940083608 sodium hydroxide Drugs 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000012080 ambient air Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000011449 brick Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000227 grinding Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000001095 magnesium carbonate Substances 0.000 description 3
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
235000014380 magnesium carbonate Nutrition 0.000 description 3
229910000021 magnesium carbonate Inorganic materials 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
229940044600 maleic anhydride Drugs 0.000 description 3
-1 phenol itself Chemical compound 0.000 description 3
239000002023 wood Substances 0.000 description 3
OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
XOJQTGARUKLYFA-UHFFFAOYSA-N cyclohexanone;furan-2-carbaldehyde Chemical compound O=CC1=CC=CO1.O=C1CCCCC1 XOJQTGARUKLYFA-UHFFFAOYSA-N 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000012545 processing Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000004448 titration Methods 0.000 description 2
229960004418 trolamine Drugs 0.000 description 2
150000003739 xylenols Chemical class 0.000 description 2
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000011324 bead Substances 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910021386 carbon form Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000000571 coke Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000007429 general method Methods 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
229960004011 methenamine Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
- C08G16/0256—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing oxygen in the ring
- C08G16/0262—Furfuryl alcohol
- 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
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
- 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
- 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
- C08G8/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of furfural

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Phenolic Resins Or Amino Resins (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA000352555A 1979-06-20 1980-05-23 Resine liquide de novolaque et produits derives Expired CA1164141A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5047879A	1979-06-20	1979-06-20
US50,478		1979-06-20

Publications (1)

Publication Number	Publication Date
CA1164141A true CA1164141A (fr)	1984-03-20

Family

ID=21965472

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000352555A Expired CA1164141A (fr)	1979-06-20	1980-05-23	Resine liquide de novolaque et produits derives

Country Status (6)

Country	Link
JP (1)	JPS564646A (fr)
CA (1)	CA1164141A (fr)
DE (1)	DE3022534A1 (fr)
GB (1)	GB2053250B (fr)
NO (1)	NO801834L (fr)
SE (1)	SE8004590L (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1216697A (fr) *	1981-12-29	1987-01-13	Peter W. Kopf	Procede pour obtenir des resines de novolac particulaires et les dispersions aqueuses
DE3800584A1 (de) *	1988-01-12	1989-07-20	Ruehl Erich	Nicht brennbarer, fuellstoff enthaltender hartschaum auf phenol-furanharzbasis
DE4243797C2 (de) *	1992-12-23	1997-01-30	Hoechst Ag	Härtbare phenolharzmodifizierte Furanharze als Bindemittel für Kitte und Beschichtungsmassen mit verbesserter Thermostabilität, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4423913A1 (de) *	1994-07-07	1996-01-11	Ruetgerswerke Ag	Flüssige Bindemittel
WO2001048085A1 (fr) *	1999-12-27	2001-07-05	Kanebo, Limited	Composition ou compose de resine phenolique thermodurcissable, ou son composite de carbone
USD518729S1 (en) *	2004-03-31	2006-04-11	Micasa Trading Corporation	Liquid bottle

1980
- 1980-05-23 CA CA000352555A patent/CA1164141A/fr not_active Expired
- 1980-05-28 GB GB8017431A patent/GB2053250B/en not_active Expired
- 1980-06-16 DE DE19803022534 patent/DE3022534A1/de not_active Withdrawn
- 1980-06-19 NO NO801834A patent/NO801834L/no unknown
- 1980-06-19 JP JP8344180A patent/JPS564646A/ja active Pending
- 1980-06-19 SE SE8004590A patent/SE8004590L/xx unknown

Also Published As

Publication number	Publication date
GB2053250A (en)	1981-02-04
NO801834L (no)	1980-12-22
SE8004590L (sv)	1980-12-21
GB2053250B (en)	1983-03-23
DE3022534A1 (de)	1981-01-08
JPS564646A (en)	1981-01-19

Legal Events

Date	Code	Title	Description
2001-03-20	MKEX	Expiry

Publication	Publication Date	Title
US5032642A (en)	1991-07-16	Phenolic resin compositions
JP4022201B2 (ja)	2007-12-12	ノボラック型フェノール樹脂の製造方法
EP0081638B1 (fr)	1985-09-18	Résols particulaires, ayant une vitesse de durcissement et résistance au frittage améliorées
CA1164141A (fr)	1984-03-20	Resine liquide de novolaque et produits derives
EP0063777B1 (fr)	1986-03-19	Résine phénol-formaldéhyde granulaire ou poudreuse et le procédé pour sa production
SE435630B (sv)	1984-10-08	Forfarande for framstellning av partikelformiga, fasta, vermereaktiva, vattenolosliga resolformningskompositioner samt produkt framstelld fran forfarandet
EP0071061B1 (fr)	1986-05-21	Résine copolymère phénol-aldéhyde granulaire ou pulvérulente contenant de l'azote et procédé pour sa préparation
JP4435791B2 (ja)	2010-03-24	ノボラック型フェノール樹脂の製造方法及びレジンコーテッドサンド
US4929649A (en)	1990-05-29	Cold-setting moulding binders and their use (phenols and gaseous acetals)
JP2001253924A (ja)	2001-09-18	フェノール樹脂組成物
JP2001247639A (ja)	2001-09-11	ノボラック型フェノール樹脂の製造方法
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JP4661087B2 (ja)	2011-03-30	固形レゾール型フェノール樹脂の製造方法
JPH0791351B2 (ja)	1995-10-04	ノボラック型フェノール樹脂
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JP7718836B2 (ja)	2025-08-05	低温速硬化レゾール樹脂組成物
SU1235874A1 (ru)	1986-06-07	Способ получени алкилрезорцинфенолформальдегидной смолы
US3658759A (en)	1972-04-25	Fluorinated resole
JPH0651824B2 (ja)	1994-07-06	フエノ−ル樹脂結合剤
JP2001253932A (ja)	2001-09-18	フェノール樹脂組成物
GB2131789A (en)	1984-06-27	Binder for calcined dolomite refractory compositions
US1980987A (en)	1934-11-20	Xylenitic resin and process of making same
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JP3545800B2 (ja)	2004-07-21	フェノール樹脂組成物の製造方法
SU923048A1 (ru)	1984-03-15	Св зующее дл изготовлени литейных форм и стержней и способ его получени