CA1080740A - Agents tensioactifs a base de copolymeres a plusieurs sequences de polyoxyalkylene - Google Patents

Agents tensioactifs a base de copolymeres a plusieurs sequences de polyoxyalkylene

Info

Publication number: CA1080740A
Authority: CA; Canada
Prior art keywords: oxyethylene; oxypropylene; units; group; weight percent
Prior art date: 1976-02-02
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

CA256,457A

Other languages

English (en)

Inventor

William K. Langdon

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.)

BASF Corp

Original Assignee

BASF Wyandotte Corp

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.)

1976-02-02

Filing date

1976-07-07

Publication date

1980-07-01

1976-02-02 Priority claimed from US05/654,268 external-priority patent/US4072704A/en

1976-07-07 Application filed by BASF Wyandotte Corp filed Critical BASF Wyandotte Corp

1980-07-01 Application granted granted Critical

1980-07-01 Publication of CA1080740A publication Critical patent/CA1080740A/fr

Status Expired legal-status Critical Current

Links

239000004094 surface-active agent Substances 0.000 title abstract description 12
229920001577 copolymer Polymers 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 26
-1 alkylene glycol Chemical compound 0.000 claims description 60
125000006353 oxyethylene group Chemical group 0.000 claims description 55
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
230000002209 hydrophobic effect Effects 0.000 claims description 21
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 3
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims 2
VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 claims 2
229920000642 polymer Polymers 0.000 abstract description 13
125000002947 alkylene group Chemical group 0.000 abstract description 6
150000002148 esters Chemical class 0.000 abstract description 4
239000004417 polycarbonate Substances 0.000 abstract description 3
229920000515 polycarbonate Polymers 0.000 abstract description 3
230000001588 bifunctional effect Effects 0.000 abstract 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 45
239000003054 catalyst Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
238000005859 coupling reaction Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
125000005702 oxyalkylene group Chemical group 0.000 description 7
229920001451 polypropylene glycol Polymers 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
125000005910 alkyl carbonate group Chemical group 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 5
238000010533 azeotropic distillation Methods 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000376 reactant Substances 0.000 description 3
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000005587 carbonate group Chemical group 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
238000010992 reflux Methods 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000004753 textile Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
MWCBGWLCXSUTHK-UHFFFAOYSA-N 2-methylbutane-1,4-diol Chemical compound OCC(C)CCO MWCBGWLCXSUTHK-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 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
229930040373 Paraformaldehyde Natural products 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical group CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
229960005082 etohexadiol Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012634 fragment Substances 0.000 description 1
125000003827 glycol group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
229940051250 hexylene glycol Drugs 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
150000002483 hydrogen compounds Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
125000000879 imine group Chemical group 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229960004319 trichloroacetic acid Drugs 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Landscapes

Polyethers (AREA)

CA256,457A 1976-02-02 1976-07-07 Agents tensioactifs a base de copolymeres a plusieurs sequences de polyoxyalkylene Expired CA1080740A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/654,268 US4072704A (en)	1974-08-19	1976-02-02	Multi-block coupled polyoxyalkylene copolymer surfactants

Publications (1)

Publication Number	Publication Date
CA1080740A true CA1080740A (fr)	1980-07-01

Family

ID=24624157

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA256,457A Expired CA1080740A (fr)	1976-02-02	1976-07-07	Agents tensioactifs a base de copolymeres a plusieurs sequences de polyoxyalkylene

Country Status (1)

Country	Link
CA (1)	CA1080740A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6083524A (en)	1996-09-23	2000-07-04	Focal, Inc.	Polymerizable biodegradable polymers including carbonate or dioxanone linkages

1976
- 1976-07-07 CA CA256,457A patent/CA1080740A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6083524A (en)	1996-09-23	2000-07-04	Focal, Inc.	Polymerizable biodegradable polymers including carbonate or dioxanone linkages
US6177095B1 (en)	1996-09-23	2001-01-23	Focal, Inc	Polymerizable biodegradable polymers including carbonate or dioxanone linkages
USRE39713E1 (en)	1996-09-23	2007-07-03	Genzyme Corporation	Polymerizable biodegradable polymers including carbonate or dioxanone linkages

Legal Events

Date	Code	Title	Description
1997-07-02	MKEX	Expiry

Publication	Publication Date	Title
US4072704A (en)	1978-02-07	Multi-block coupled polyoxyalkylene copolymer surfactants
US4189609A (en)	1980-02-19	Multi-block coupled polyoxyalkylene copolymer surfactants
EP0295055A3 (fr)	1990-05-02	Matériaux polymériques biodégradables à base de polyétherglycols, procédé pour leur préparation et articles chirurgicaux
CA1198449A (fr)	1985-12-24	Composes tensio-actifs; preparation et utilisation
DE102008000903A1 (de)	2009-10-08	Neue Organosiloxangruppen tragende Polyetheralkohole durch Alkoxylierung epoxidfunktioneller (Poly)Organosiloxane an Doppelmetallcyanid (DMC)-Katalysatoren, sowie Verfahren zu deren Herstellung
CN1047307A (zh)	1990-11-28	由三烷和丙三醇缩甲醛的α，α-和α，β-异构体以及它们的官能衍生物聚合而成的新的乙缩醛三元共聚物
US7176264B2 (en)	2007-02-13	Process for manufacture of a dendritic polyether
CA1177096A (fr)	1984-10-30	Agents tensioactifs anioniques a faible degagement d'ecumes
CA1100245A (fr)	1981-04-28	Procede d'obtention de polyols de polyether
CA1080740A (fr)	1980-07-01	Agents tensioactifs a base de copolymeres a plusieurs sequences de polyoxyalkylene
US4275244A (en)	1981-06-23	Linear polyalkylene ether glycols of high molecular weight
US4353834A (en)	1982-10-12	Carbonate and carboxylic acid ester group-containing non-ionic surface-active agents
CA1072583A (fr)	1980-02-26	Surfactants de type copolymeres de polyacetal multisequences
US4504418A (en)	1985-03-12	Non-ionic surface-active agents coupled with carbonates or carboxylic esters
CA1101416A (fr)	1981-05-19	Traduction non-disponible
US4408084A (en)	1983-10-04	Non-ionic surfactants containing acetal groups
US3629364A (en)	1971-12-21	Phenolic resin compositions containing polymers of cylic esters
US3083187A (en)	1963-03-26	Detergent polyesters
EP0628023A1 (fr)	1994-12-14	Preparation et purification de poly(tetramethylene ether) formal glycols et de poly(oxybutylene formal)glycols
KR19980064301A (ko)	1998-10-07	에틸렌형 불포화 중합체의 설폰화를 통해 설포네이트 그룹을 함유하는 기능성 그룹 말단의 중합체
KR970700712A (ko)	1997-02-12	3,4-에폭시-1-부텐으로부터 유도된 폴리에테르 글리콜 및 알콜(polyether glycols and alcohols derived from 3,4-epoxy-1-butene)
US4326050A (en)	1982-04-20	Process and product
JPH10510315A (ja)	1998-10-06	３，４−エポキシ−１−ブテン、テトラヒドロフラン及び開始剤から誘導されたポリエーテルグリコール及びアルコール
US4519950A (en)	1985-05-28	Acetal group-containing non-ionic surfactants
US20160145382A1 (en)	2016-05-26	Polymeric surfactant