CA1080871B - Resines catalysees par le calcium - Google Patents

Resines catalysees par le calcium

Info

Publication number: CA1080871B
Authority: CA; Canada
Prior art keywords: phenol; formaldehyde; resin; calcium; reaction
Prior art date: 1972-06-08
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

CA 343480

Other languages

English (en)

Inventor

Ruben A. Santos

Hendrik H. J. Deuzeman

Norman Lumley

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.)

Owens Corning Canada Inc

Original Assignee

Fiberglas Canada Inc

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.)

1972-06-08

Filing date

1980-01-11

Publication date

1980-07-01

1972-06-08 Priority claimed from CA144,203A external-priority patent/CA981827A/en

1980-01-11 Application filed by Fiberglas Canada Inc filed Critical Fiberglas Canada Inc

1980-01-11 Priority to CA 343480 priority Critical patent/CA1080871B/fr

1980-07-01 Application granted granted Critical

1980-07-01 Publication of CA1080871B publication Critical patent/CA1080871B/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 73
239000011347 resin Substances 0.000 title claims abstract description 73
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 title claims abstract description 43
239000000292 calcium oxide Substances 0.000 title claims abstract description 37
235000012255 calcium oxide Nutrition 0.000 title abstract description 33
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 165
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 86
239000011575 calcium Substances 0.000 claims abstract description 28
238000006243 chemical reaction Methods 0.000 claims abstract description 28
239000011230 binding agent Substances 0.000 claims abstract description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
229910052791 calcium Inorganic materials 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 24
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 20
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims abstract description 17
229920001568 phenolic resin Polymers 0.000 claims abstract description 17
239000000178 monomer Substances 0.000 claims abstract description 16
239000000920 calcium hydroxide Substances 0.000 claims abstract description 14
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 13
229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 13
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 11
239000007795 chemical reaction product Substances 0.000 claims abstract description 9
238000006482 condensation reaction Methods 0.000 claims abstract description 8
238000009472 formulation Methods 0.000 claims abstract description 7
229960004279 formaldehyde Drugs 0.000 claims description 54
235000019256 formaldehyde Nutrition 0.000 claims description 53
239000003054 catalyst Substances 0.000 claims description 19
239000000243 solution Substances 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical class OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 7
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
239000000758 substrate Substances 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
-1 methylol groups Chemical group 0.000 claims description 3
150000001243 acetic acids Chemical class 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
150000004653 carbonic acids Chemical class 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
150000002689 maleic acids Chemical class 0.000 claims description 2
230000001276 controlling effect Effects 0.000 claims 5
LSYXXLMBRSSBGS-UHFFFAOYSA-N 2,4,6-tris(hydroxymethyl)phenol Chemical class OCC1=CC(CO)=C(O)C(CO)=C1 LSYXXLMBRSSBGS-UHFFFAOYSA-N 0.000 claims 3
235000020354 squash Nutrition 0.000 claims 3
239000000376 reactant Substances 0.000 claims 2
238000011437 continuous method Methods 0.000 claims 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 8
238000004519 manufacturing process Methods 0.000 abstract description 7
229920001187 thermosetting polymer Polymers 0.000 abstract description 5
239000007859 condensation product Substances 0.000 abstract description 4
239000003365 glass fiber Substances 0.000 abstract description 3
239000002904 solvent Substances 0.000 abstract description 2
239000006260 foam Substances 0.000 abstract 1
238000012986 modification Methods 0.000 abstract 1
230000004048 modification Effects 0.000 abstract 1
235000001465 calcium Nutrition 0.000 description 16
229960005069 calcium Drugs 0.000 description 16
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 13
229940087373 calcium oxide Drugs 0.000 description 13
239000004202 carbamide Substances 0.000 description 13
239000007787 solid Substances 0.000 description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000000463 material Substances 0.000 description 10
235000011116 calcium hydroxide Nutrition 0.000 description 9
239000004615 ingredient Substances 0.000 description 8
238000006386 neutralization reaction Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910002092 carbon dioxide Inorganic materials 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000007792 addition Methods 0.000 description 5
229920006026 co-polymeric resin Polymers 0.000 description 5
239000005011 phenolic resin Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 4
XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052788 barium Inorganic materials 0.000 description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
230000005484 gravity Effects 0.000 description 3
239000002245 particle Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
QFKJCKFAYFUXRQ-UHFFFAOYSA-N barium;hydrate Chemical class O.[Ba] QFKJCKFAYFUXRQ-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
229920003987 resole Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910007161 Si(CH3)3 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000000809 air pollutant Substances 0.000 description 1
231100001243 air pollutant Toxicity 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000010951 brass Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000004087 circulation Effects 0.000 description 1
238000010961 commercial manufacture process Methods 0.000 description 1
238000010411 cooking Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol

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)

CA 343480 1972-06-08 1980-01-11 Resines catalysees par le calcium Expired CA1080871B (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 343480 CA1080871B (fr)	1972-06-08	1980-01-11	Resines catalysees par le calcium

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA144,203A CA981827A (en)	1972-06-08	1972-06-08	Calcia catalyzed resins
CA 343480 CA1080871B (fr)	1972-06-08	1980-01-11	Resines catalysees par le calcium

Publications (1)

Publication Number	Publication Date
CA1080871B true CA1080871B (fr)	1980-07-01

Family

ID=25667064

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 343480 Expired CA1080871B (fr)	1972-06-08	1980-01-11	Resines catalysees par le calcium

Country Status (1)

Country	Link
CA (1)	CA1080871B (fr)

1980
- 1980-01-11 CA CA 343480 patent/CA1080871B/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-07-02	MKEX	Expiry

Publication	Publication Date	Title
SU784787A3 (ru)	1980-11-30	Способ получени углеводфенольной смолы
US4339361A (en)	1982-07-13	Phenol-formaldehyde resins extended with carbohydrates for use in binder compositions
US4710406A (en)	1987-12-01	Resin for a sizing composition, a process for its preparation and the sizing composition obtained
AU625517B2 (en)	1992-07-16	Phenol-formaldehyde resin solution containing water soluble alkaline earth metal salt
PL206776B1 (pl)	2010-09-30	Kompozycja żywiczna, kompozycja klejowa zawierająca tę kompozycję żywiczną do produktu na bazie wełny mineralnej, sposób wytwarzania produktu na bazie wełny mineralnej
CA2368869C (fr)	2010-05-11	Resine formaldehyde a faible emission et liant pour isolant en fibres minerales
US5270434A (en)	1993-12-14	Phenolic resin, procedure for preparation of the resin, and sizing composition for mineral fibers containing this resin
US2191802A (en)	1940-02-27	Preparation of fusible ketonealdehyde synthetic resins
EP0081638B1 (fr)	1985-09-18	Résols particulaires, ayant une vitesse de durcissement et résistance au frittage améliorées
US3932334A (en)	1976-01-13	Calcia catalyzed resins
US4482699A (en)	1984-11-13	Low emitting aqueous formulations of aminoplast resins and processes for manufacturing them
USRE30375E (en)	1980-08-19	Calcia catalyzed resins
US4376854A (en)	1983-03-15	Process for preparing resorcinol copolymers
PL167251B1 (pl)	1995-08-31	Sposób wytwarzania zywicy fenolowej PL PL PL PL
CA1149548A (fr)	1983-07-05	Regulation de procedes pour l'obtention de resines de phenol-formaldehyde thermodurcissables, non miscibles a l'eau
US4381368A (en)	1983-04-26	Process for the preparation of urea-formaldehyde resins
CA1080871B (fr)	1980-07-01	Resines catalysees par le calcium
GB2155941A (en)	1985-10-02	Solid urea-formaldehyde resin
US2715619A (en)	1955-08-16	Process for manufacturing alkylated
US3677979A (en)	1972-07-18	Sulfonated phenol-aldehyde resins
CA1164141A (fr)	1984-03-20	Resine liquide de novolaque et produits derives
US4198499A (en)	1980-04-15	Process for producing neutralized phenol resins
US3640932A (en)	1972-02-08	Compositions for sand core mold elements
JPH06228255A (ja)	1994-08-16	生分解性フェノール樹脂の製造方法
US2458408A (en)	1949-01-04	Acrolein-phenol resin