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US4820388A
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Polyalkylene glycol naphthyl-3-sulfopropyl diether compounds and their salts, process for preparing same and electroplating baths containing same
Assignee: Elektro-Brite GmbH and Co KG
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Filing: 1988-06-13
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Granted: 1989-04-11
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Expires: 2008-06-13
Abstract
Abstract Novel Polyalkylenglycol naphthyl-3-sulfopropyl diethers and salts thereof of the formula ##STR1## (R 1 -R 3 =H, C p H 2p--1 ; p=l--4, A=(PO) m --(EO) n --, (EO) n --(PO) m ,--(EO) n EO=ethylenoxide residue, PO=propylenoxide residue, m=0-15, n-1-40, A=H, alkali metal, earth alkali metal, NR 5 R 6 R 7 R 8 wherein R 5 -R 8 =H, C 1 -C 4 --alkyl, aryl, aralkyl) are prepared by reacting the corresponding polyalkylene glycol naphthyl either with propane-1.3-sultone. The compounds are surfactants in particular in electroplating baths for precipitation Zn, Sn, Cu, Ag, Ni and alloys thereof.
Inventors
- 👤 Werner Kurze
- 👤 Klaus-Peter Klos
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 12:06
CPC Classifications
C; C07; C07C; C07C309/00; C25; C25D; C25D3/00; C25D3/02; C25D3/22; C25D3/56; C25D3/565
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
180 words
A polyalkyleneglycol naphthyl- 3-sulfopropyl diether compound, or salt thereof, of the formula: ##STR5## wherein, R 1 , R 2 and R 3 represent a member selected from the group consisting of hydrogen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR6## and ##STR7## m is an integer of from 0 to 15, and n is an integer from 1 to 40; and, B is a member selected from the group consisting of hydrogen, an alkali metal, an earth alkali metal and an ammonium cation of the formula NR 4 R 5 R 6 R 7 wherein R 4 -R 7 are independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group.
Claim 2
Dependent Claim
180 words
A polyalkyleneglycol naphthyl- 3-sulfopropyl diether compound, or salt thereof, of the formula: ##STR5## wherein, R 1 , R 2 and R 3 represent a member selected from the group consisting of hydrogen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR6## and ##STR7## m is an integer of from 0 to 15, and n is an integer from 1 to 40; and, B is a member selected from the group consisting of hydrogen, an alkali metal, an earth alkali metal and an ammonium cation of the formula NR 4 R 5 R 6 R 7 wherein R 4 -R 7 are independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group.
Claim 3
Dependent Claim
368 words
A process for the preparation of a polyalkyleneglycol naphthyl-3-sulfopropyl diether compound, or a salt thereof, of the formula: ##STR8## wherein, R 1 , R 2 and R 3 represent a member selected from the group consisting of hydrogen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR9## and ##STR10## m is an integer of from 0 to 15, and n is an integer from 1 to 40; and, B is a member selected from the group consisting of hydrogen, an alkali metal, an earth alkali metal and an ammonium cation of the formula NR 4 R 5 R 6 R 7 wherein R 4 -R 7 are independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group. comprising the step of: reacting a compound of the formula: formula II: ##STR11## wherein, R 1 , R 2 and R 3 represent a member selected from a group consisting of hydrongen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; and A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR12## and ##STR13## m is an integer of from 0 to 15, and n is an integer from 1 to 40, with propane-1,3-sultone in the presence of a member selected from the group consisting of an alkali hydroxide, an earth alkali hydroxide and ammonium hydroxide of the formula NR 4 R 5 R 6 R 7 OH, wherein R 4 -R 7 are independently selected from the group consisting of an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group.
Claim 4
Dependent Claim
368 words
A process for the preparation of a polyalkyleneglycol naphthyl-3-sulfopropyl diether compound, or a salt thereof, of the formula: ##STR8## wherein, R 1 , R 2 and R 3 represent a member selected from the group consisting of hydrogen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR9## and ##STR10## m is an integer of from 0 to 15, and n is an integer from 1 to 40; and, B is a member selected from the group consisting of hydrogen, an alkali metal, an earth alkali metal and an ammonium cation of the formula NR 4 R 5 R 6 R 7 wherein R 4 -R 7 are independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group. comprising the step of: reacting a compound of the formula: formula II: ##STR11## wherein, R 1 , R 2 and R 3 represent a member selected from a group consisting of hydrongen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; and A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR12## and ##STR13## m is an integer of from 0 to 15, and n is an integer from 1 to 40, with propane-1,3-sultone in the presence of a member selected from the group consisting of an alkali hydroxide, an earth alkali hydroxide and ammonium hydroxide of the formula NR 4 R 5 R 6 R 7 OH, wherein R 4 -R 7 are independently selected from the group consisting of an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group.
Claim 5
Dependent Claim
19 words
The process according to claim 2, further comprising the step of replacing B of the compound obtained with hydrogen.
Claim 6
Dependent Claim
30 words
The process according to claim 3, further comprising the step of neutralizing an acid obtained with a base of the formula NR 4 R 5 R 6 R 7 .
Claim 7
Dependent Claim
192 words
An electroplating bath or an electroless chromium plating bath comprising at least one polyalkyleneglycol naphthyl-3-sulfopropyl diether compound, or a salt thereof, of the formula: ##STR14## wherein, R 1 , R 2 and R 3 represent a member selected from a group consisting of hydrogen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR15## and ##STR16## m is an integer of from 0 to 15, and n is an integer from 1 to 40; and, B is a member selected from the group consisting of hydrogen, an alakli metal, an earth alkali metal and an ammonium cation of the formula NR 4 R 5 R 6 R 7 wherein R 4 --R 7 are independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group.
Claim 8
Dependent Claim
192 words
An electroplating bath or an electroless chromium plating bath comprising at least one polyalkyleneglycol naphthyl-3-sulfopropyl diether compound, or a salt thereof, of the formula: ##STR14## wherein, R 1 , R 2 and R 3 represent a member selected from a group consisting of hydrogen and a lower alkyl group C p H 2p+1 wherein p is an integer from 1 to 4; A represents a member selected from the group consisting of --(PO) m --(EO) n --, --(EO) n --(PO) m -- and --(EO)(PO) n , wherein EO is a --CH 2 CH 2 --O-- group and PO is a member selected from the group consisting of ##STR15## and ##STR16## m is an integer of from 0 to 15, and n is an integer from 1 to 40; and, B is a member selected from the group consisting of hydrogen, an alakli metal, an earth alkali metal and an ammonium cation of the formula NR 4 R 5 R 6 R 7 wherein R 4 --R 7 are independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 4 carbon atoms, an aryl and an aralkyl group.
Claim 9
Dependent Claim
38 words
An electroplating bath according to claim 5 for depositing zinc, tin, nickel, copper, silver and alloys thereof wherein m is an integer of from 1 to 5 and n is an integer from 2-24 in defining said compound.
Claim 10
Dependent Claim
30 words
An electroless chromium plating bath according to claim 5 wherein m is an integer of from 1 to 5 and n is an integer from 2-24 in defining said compound.
References Cited (Backward Citations)
US4153575A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1992-04-10 | 1992-10-10 | 1993-04-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-04-10 | 1996-10-10 | 1997-04-11 | $3760.00 | Window Closed / Lapsed |
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