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US5045624A
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Heteroatom containing perfluoroalkyl terminated neopentyl glycols and compositions therefrom
Assignee: BASF Corp
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Filing: 1990-06-05
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Granted: 1991-09-03
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Expires: 2010-06-05
Abstract
Abstract Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH 2 C(CH 2 X--E--R f ) 2 CH 2 O] 1-3 --H or HO[--CH 2 C(CH 2 X--R f ) 2 CH 2 O] 1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R f --E--SH, amines of the formula R f --E--NH--R, alcohols of the formula R f --E--OH or perfluoro-amides, wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms. The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanates to prepare polyureas/polyuretanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R f -neopentyl glycol containing two perfluoroalkyl hetero groups. These polymeric compositions provide improved thermal stability and useful low surface energy oil and water repellent coatings, and soil-release properties for textiles, glass, paper, leather and other materials.
Inventors
- 👤 Robert A. Falk
- 👤 Kirtland P. Clark
- 👤 Athanasios Karydas
- 👤 Michael Jacobson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:53
CPC Classifications
C; C07; C07C; C07C215/00; C07C215/02; C07C215/04; C07C215/06; C07C215/18; C07C311/00; C07C311/01; C07C311/02; C07C311/03; C07C311/04; C07C313/00; C07C313/08; C07C313/10; C07C313/12; C07C317/00; C07C317/16; C07C317/18; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07C323/39; C07C323/40; C07C323/41; C07C43/00; C07C43/02; C07C43/03; C07C43/04; C07C43/13; C07C43/137; C07D; C07D305/00; C07D305/02; C07D305/04; C07D305/06; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3802; C08G18/3804; C08G18/3812; C08G18/3855; C08G18/3857; C08G18/3861; C08G18/3863; C08G18/3865; C08G18/3868; C08G18/387; C08G18/40; C08G18/42; C08G18/46; C08G18/4607; C08G18/48; C08G18/50; C08G18/5003; C08G18/5015; C08G63/00; C08G63/68; C08G63/682; C08G63/6824; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/16; C08G65/18; C08G65/22; C08G65/223; C08G65/226; C08G71/00; C08G71/04; D; D06; D06M; D06M15/00; D06M15/19; D06M15/37; D06M15/564; D06M15/576; D06N; D06N3/00; D06N3/12; D06N3/14; D06N3/146; D06M2200/00; D06M2200/10; D06M2200/11; D06M2200/12
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
182 words
A linear polyurethane having recurring structural units of the formula Ia or IIa: ##STR27## wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--,--SO 2 --, --COO--, --OOC--, --CONR--,--NRCO--, --SO 2 NR--, and --NRSO 2 --, or terminated at the R f end with --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and for formula Ia, X is --S--, --O--, --SO 2 --, or --NR--, and for formula IIa, X is --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and m is 1, 2 or 3, and A is a divalent aliphatic, cycloaliphatic or aromatic group.
Claim 2
Dependent Claim
182 words
A linear polyurethane having recurring structural units of the formula Ia or IIa: ##STR27## wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--,--SO 2 --, --COO--, --OOC--, --CONR--,--NRCO--, --SO 2 NR--, and --NRSO 2 --, or terminated at the R f end with --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and for formula Ia, X is --S--, --O--, --SO 2 --, or --NR--, and for formula IIa, X is --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and m is 1, 2 or 3, and A is a divalent aliphatic, cycloaliphatic or aromatic group.
Claim 3
Dependent Claim
104 words
A polyurethane according to claim 1 wherein A is alkylene of 2 to 16 carbon atoms, cycloalkylene of 6 to 15 mcarbon atoms, phenylene, naphthylene or said phenylene or said naphthylene substituted by one or two alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms, by chloro, by bromo or by nitro, or A is a group of the formula ##STR28## where D is a direct bond, oxygen, methylene or ethylene, and a, a', a" and a'" each independently are hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, chloro or bromo.
Claim 4
Dependent Claim
12 words
A polyurethane according to claim 1 wherein A is 3,3,4-trimethyl-1,16-hexanediyl or 1,3,3-trimethyl-alpha,5-hexahydrobenzylene.
Claim 5
Dependent Claim
100 words
A polyurethane according to claim 1 where R f is perfluoroalkyl of 2 to 12 carbon atoms or perfluoroalkyl of 2 to 6 carbon atoms substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is alkylene of 2 to 6 carbon atoms, --CONHCH 2 CH 2 --, --CH 2 CH 2 N(CH 3 )CH 2 CH 2 --,--CH 2 CH 2 SO 2 NHCH 2 CH 2 --, --CH 2 CH 2 OCH 2 CH 2 --, or --SO 2 NHCH 2 CH 2 --, X is --S--, SO 2 -- or --O--, and m is 1 or 2.
Claim 6
Dependent Claim
267 words
A linear block copolymer having soil-release properties which contains, based on the total block copolymer, (a) 15-70% by weight of recurring structural units of blocks Ia, IIa or a mixture thereof, (b) 85 to 30% by weight of recurring structural units of block III, wherein the blocks are connected to one another via urea linkages, blocks Ia or IIa having recurring structural units of the formula ##STR29## block III having recurring structural units of the formula: ##STR30## wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--,--SO 2 --, --COO--, --OOC--, --CONR--,--NRCO--, --SO 2 NR--, and --NRSO 2 --, or terminated at the R f end with --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and for formula Ia, X is --S--, --O--, --SO 2 --, or --NR--, and for formula IIa, X is --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and m is 1, 2 or 3. A is a divalent aliphatic, cycloaliphatic or aromatic group, R 4 is hydrogen or methyl, k is 8 to 100, and p and t are integers and are independently 1 to 5.
Claim 7
Dependent Claim
267 words
A linear block copolymer having soil-release properties which contains, based on the total block copolymer, (a) 15-70% by weight of recurring structural units of blocks Ia, IIa or a mixture thereof, (b) 85 to 30% by weight of recurring structural units of block III, wherein the blocks are connected to one another via urea linkages, blocks Ia or IIa having recurring structural units of the formula ##STR29## block III having recurring structural units of the formula: ##STR30## wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--,--SO 2 --, --COO--, --OOC--, --CONR--,--NRCO--, --SO 2 NR--, and --NRSO 2 --, or terminated at the R f end with --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and for formula Ia, X is --S--, --O--, --SO 2 --, or --NR--, and for formula IIa, X is --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and m is 1, 2 or 3. A is a divalent aliphatic, cycloaliphatic or aromatic group, R 4 is hydrogen or methyl, k is 8 to 100, and p and t are integers and are independently 1 to 5.
Claim 8
Dependent Claim
102 words
A block copolymer according to claim 5 wherein R f is perfluoroalkyl of 2 to 12 carbon atoms or perfluoroalkyl of 2 to 6 carbon atoms substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is alkylene of 2 to 6 carbon atoms, --CONHCH 2 CH 2 --, --CH 2 CH 2 N(CH 3 )CH 2 CH 2 --,--CH 2 CH 2 SO 2 NHCH 2 CH 2 --, --CH 2 CH 2 OCH 2 CH 2 --, or --SO 2 NHCH 2 CH 2 13 , X is --S--, SO 2 -- or --0--, and m is 1 or 2.
Claim 9
Dependent Claim
105 words
A block copolymer according to claim 5 wherein A is alkylene of 2 to 16 carbon atoms, cycloalkylene of 6 to 15 carbon atoms, phenylene, naphthylene or said phenylene or said naphthylene substituted by one or two alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms, by chloro, by bromo or by nitro, or A is a group of the formula ##STR31## where D is a direct bond, oxygen, methylene or ethylene, and a, a', a" and a'" each independently is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, chloro or bromo.
Claim 10
Dependent Claim
13 words
A block copolymer according to claim 5 wherein A is 3,3,4-trimethyl-1,6-hexanediyl of 1,3,3-trimethyl-alpha,5-hexahydrobenzylene.
Claim 11
Dependent Claim
217 words
A linear polyester having recurring structural units of the formula Ib or IIb --[OCH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.m --CO--L--CO]-- (Ib) or --[OCH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.m --CO--L--CO]--(IIb) wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--,--SO 2 --, --COO--, --OOC--, --CONR--,--NRCO--, --SO 2 NR--, and --NRSO 2 --, or terminated at the R f end with --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and for formula Ib, X is --S--, --O--, --SO 2 --, or --NR--, and for formula IIb, X is --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and m is 1, 2 or 3. L is a direct bond, a straight or branched chain alkylene of 1 to 34 carbon atoms, cycloalkylene of 6 to 12 carbon atoms, or arylene of 6 to 16 carbon atoms.
Claim 12
Dependent Claim
217 words
A linear polyester having recurring structural units of the formula Ib or IIb --[OCH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.m --CO--L--CO]-- (Ib) or --[OCH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.m --CO--L--CO]--(IIb) wherein R f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--,--SO 2 --, --COO--, --OOC--, --CONR--,--NRCO--, --SO 2 NR--, and --NRSO 2 --, or terminated at the R f end with --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and for formula Ib, X is --S--, --O--, --SO 2 --, or --NR--, and for formula IIb, X is --CONR-- or --SO 2 NR--, where R f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and m is 1, 2 or 3. L is a direct bond, a straight or branched chain alkylene of 1 to 34 carbon atoms, cycloalkylene of 6 to 12 carbon atoms, or arylene of 6 to 16 carbon atoms.
Claim 13
Dependent Claim
101 words
A polyester according to claim 9 where R f is perfluoroalkyl of 2 to 12 carbon atoms or perfluoroalkyl of 2 to 6 carbon atoms substituted by perfluoroalkoxy of 2 to 6 carbon atoms, E is alkylene of 2 to 6 carbon atoms, --CONHCH 2 CH 2 --, --CH 2 CH 2 N(CH 3 )CH 2 CH 2 --,--CH 2 CH 2 SO 2 NHCH 2 CH 2 --, --CH 2 CH 2 OCH 2 CH 2 --, or --SO 2 NHCH 2 CH 2 13 , X is --S--, SO 2 -- or --O--, and m is 1 or 2.
Claim 14
Dependent Claim
12 words
A polyester according to claim 9 wherein L is tetramethylene or o-phenylene.
References Cited (Backward Citations)
US3478116A
Cited
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