CA1124233A - Obtention d'esters de rosine - Google Patents

Obtention d'esters de rosine

Info

Publication number: CA1124233A
Authority: CA; Canada
Prior art keywords: rosin; process according; polyhydric alcohol; acid; primary polyhydric
Prior art date: 1978-02-21
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

CA321,860A

Other languages

English (en)

Inventor

Martin Epstein

Roland P.F. Scharrer

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.)

Kraton Chemical LLC

Original Assignee

Arizona Chemical Co LLC

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.)

1978-02-21

Filing date

1979-02-20

Publication date

1982-05-25

1978-04-24 Priority claimed from US05/899,041 external-priority patent/US4172070A/en

1979-02-20 Application filed by Arizona Chemical Co LLC filed Critical Arizona Chemical Co LLC

1982-05-25 Application granted granted Critical

1982-05-25 Publication of CA1124233A publication Critical patent/CA1124233A/fr

Status Expired legal-status Critical Current

Links

RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims abstract description 41
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims abstract description 41
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims abstract description 41
150000002148 esters Chemical class 0.000 title claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 25
150000005846 sugar alcohols Polymers 0.000 claims abstract description 20
238000006243 chemical reaction Methods 0.000 claims abstract description 14
238000005886 esterification reaction Methods 0.000 claims abstract description 12
230000032050 esterification Effects 0.000 claims abstract description 9
230000003197 catalytic effect Effects 0.000 claims abstract 3
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 10
239000003054 catalyst Substances 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
239000003784 tall oil Substances 0.000 claims description 5
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
239000002023 wood Substances 0.000 claims description 2
238000007171 acid catalysis Methods 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000003377 acid catalyst Substances 0.000 description 5
229920001971 elastomer Polymers 0.000 description 4
241000411998 Gliricidia Species 0.000 description 3
235000009664 Gliricidia sepium Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
238000006555 catalytic reaction Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229940113165 trimethylolpropane Drugs 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
-1 PE ester Chemical class 0.000 description 1
239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
229920013625 Synpol Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA321,860A 1978-02-21 1979-02-20 Obtention d'esters de rosine Expired CA1124233A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US87933378A	1978-02-21	1978-02-21
US879,333		1978-02-21
US89045078A	1978-03-27	1978-03-27
US890,450		1978-03-27
US899,041		1978-04-24
US05/899,041 US4172070A (en)	1978-03-27	1978-04-24	Oxygen-stable rosin-primary polyhydric aliphatic alcohol esters and a method for preparing the same utilizing arylsulfonic acid catalysis

Publications (1)

Publication Number	Publication Date
CA1124233A true CA1124233A (fr)	1982-05-25

Family

ID=27420502

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA321,860A Expired CA1124233A (fr)	1978-02-21	1979-02-20	Obtention d'esters de rosine

Country Status (8)

Country	Link
JP (1)	JPS54132598A (fr)
AU (1)	AU526700B2 (fr)
BR (1)	BR7900157A (fr)
CA (1)	CA1124233A (fr)
DE (1)	DE2852137A1 (fr)
FR (1)	FR2417536A1 (fr)
GB (1)	GB2014594B (fr)
NL (1)	NL7811883A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4659514A (en) *	1986-01-27	1987-04-21	Ciba-Geigy Corporation	Esterification of rosin acid with calcium hydroxybenzyl phosphonate catalyst

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1840395A (en) *	1930-01-24	1932-01-12	Hercules Powder Co Ltd	Method for producing resin acid esters
US2138193A (en) *	1935-08-21	1938-11-29	Hercules Powder Co Ltd	Esters of pine wood pitch and method of producing

1978
- 1978-11-23 AU AU41862/78A patent/AU526700B2/en not_active Expired
- 1978-12-01 DE DE19782852137 patent/DE2852137A1/de not_active Withdrawn
- 1978-12-05 NL NL7811883A patent/NL7811883A/xx not_active Application Discontinuation
1979
- 1979-01-10 BR BR7900157A patent/BR7900157A/pt unknown
- 1979-02-14 GB GB7905261A patent/GB2014594B/en not_active Expired
- 1979-02-16 JP JP1627779A patent/JPS54132598A/ja active Pending
- 1979-02-19 FR FR7904141A patent/FR2417536A1/fr active Granted
- 1979-02-20 CA CA321,860A patent/CA1124233A/fr not_active Expired

Also Published As

Publication number	Publication date
AU4186278A (en)	1979-08-30
BR7900157A (pt)	1979-09-11
NL7811883A (nl)	1979-08-23
FR2417536B1 (fr)	1984-07-13
FR2417536A1 (fr)	1979-09-14
GB2014594A (en)	1979-08-30
DE2852137A1 (de)	1979-08-23
GB2014594B (en)	1982-05-12
AU526700B2 (en)	1983-01-27
JPS54132598A (en)	1979-10-15

Legal Events

Date	Code	Title	Description
1999-05-25	MKEX	Expiry

Publication	Publication Date	Title
US4172070A (en)	1979-10-23	Oxygen-stable rosin-primary polyhydric aliphatic alcohol esters and a method for preparing the same utilizing arylsulfonic acid catalysis
US4302371A (en)	1981-11-24	Stabilized rosin ester and pressure-sensitive adhesive and hot-melt composition based thereon
EP0150218B1 (fr)	1989-03-08	Composition adhesive sensible a la pression
EP0583419B1 (fr)	1997-05-28	Colles a base d'ester de colophane a alcool polyvalent modifie par un acide, et compositions adhesives thermofusibles contenant ces colles
US5395920A (en)	1995-03-07	Process for preparing rosin and colorless rosin comprising disproportionation and dehydrogenation
US4788009A (en)	1988-11-29	Method of preparing rosin esters of improved thermal stability with inorganic salt of phosphorous or hypophosphorous acid
CA1199631A (fr)	1986-01-21	Esters inertes de colophane et methode de preparation
US3975323A (en)	1976-08-17	Copolyesters, method of manufacturing same, and hot melt adhesive compositions incorporating same
US4693847A (en)	1987-09-15	Method of preparing hot-melt stable rosin ester with organic ester of hypophosphorous acid catalyst
CA1124233A (fr)	1982-05-25	Obtention d'esters de rosine
US4758379A (en)	1988-07-19	Process of preparing polyol esters of rosin with excess rosin
US4377510A (en)	1983-03-22	Urethane-modified rosin ester and process for preparing the same
US4447354A (en)	1984-05-08	Method for making oxidation-stable, light-colored glycerol ester of modified rosin
US2377647A (en)	1945-06-05	Adhesive material
JPH04292678A (ja)	1992-10-16	ロジンエステルの粘度安定性改善方法
GB1384471A (en)	1975-02-19	Process for the manufacture of fatty acid ethanolamides
US5019167A (en)	1991-05-28	Stabilized rosin esters and hot melt adhesives containing them
US6274657B1 (en)	2001-08-14	Surfactant for forming stable dispersions of rosin esters
US2585222A (en)	1952-02-12	Vinyl resin plasticized with a mixture of a monohydric alcohol ester of the maleic anhydride adduct of rosin acid and a monohydric alcohol ester of a fatty acid
US4962186A (en)	1990-10-09	Method of improving the color of tall oil rosin esters by recrystallizing and distilling rosin followed by esterifying
CA1253142A (fr)	1989-04-25	Methode pour ameliorer la couleur d'esters de resine de tall oil
US3912709A (en)	1975-10-14	Zinc and zinc-calcium salts of partial esters of rosin
JP2795018B2 (ja)	1998-09-10	ロジンエステルの製造法
JPH0246625B2 (fr)	1990-10-16
JPH0264182A (ja)	1990-03-05	ロジンエステルの製造方法