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US 9,481,643 B2Granted
Fluorosurfactants
AssigneeMerck Patent GmbH
InventorsReiner Friedrich, Gerhard Jonschker, Fanny Schooren, Christian Depner, Steffen Schellenberger
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Abstract
The present invention relates to novel compounds containing fluorinated end groups, to the use thereof as surface-active substances, and to compositions comprising these compounds.
Claims21
A compound of formula (I)
- (Rf-Aa-Cc)n-(spacer)m-Xo (I)
- wherein either a) or b) provides the definitions for the elements of formula (I)
- a)
- Rf=CF3—CF2—CF2—O—CF(CF3)—CH2—,
- A=—O—CH2—CHR′—,
- R′=H or alkyl,
- C=alkylene, O, —OCO— or —NR″—,
- R″=H, alkyl or (CH2CHR′″)m′—R″″,
- m′=an integer of 1 to 100,
- R′″ and R″″=independently of one another, H or alkyl, in which one or more non-adjacent C atoms are optionally replaced by O or N,
- spacer=a saturated or unsaturated, branched or unbranched hydrocarbon unit, optionally containing heteroatoms,
- X=an anionic, cationic, non-ionic or amphoteric hydrophilic group,
- non-ionic
- hydrophilic
- group=is R4—(O—CH2CHR5)m″—, —CH(OH)—CH2—NH-Sach, or —Y—(CH2—CH2—O)v—R4′,
- m″=an integer of 1 to 100,
- R4 and R5=independently of one another H or C1-C4-alkyl,
- Sach=a sugar,
- Y=S, O or NH,
- R4′=H or alkyl and
- v=1-100,
- a=0 or 1, and a=1, if X=an anionic hydrophilic group,
- n=2, 3, 4, 5 or 6,
- c=0 or 1,
- m=0 or 1, and
- o=1, 2, 3 or 4, and o=0 if R″=—(CH2CHR′″)m′—R″″, wherein R′″ and/or R″″=alkyl, wherein one or more non-adjacent C atoms have been replaced by O or N,
- or
- b)
- Rf=CF3—CF2—CF2—O—CF(CF3)—CO—,
- A=—O—CH2—CHR′—,
- R′=H or alkyl,
- C=alkylene, O, —OCO— or —NR″—,
- R″=H, alkyl or (CH2CHR′″)m′—R″″,
- m′=an integer of 1 to 100,
- R′″ and R″″=independently of one another, H or alkyl, in which one or more non-adjacent C atoms are optionally replaced by O or N,
- spacer=a saturated or unsaturated branched or unbranched hydrocarbon unit, optionally containing heteroatoms,
- X=an anionic, cationic, non-ionic or amphoteric hydrophilic group,
- non-ionic
- hydrophilic
- group=is R4—(O—CH2CHR5)m″—, —CH(OH)—CH2—NH-Sach, or —Y—(CH2—CH2—O)v—R4′,
- m″=an integer of 1 to 100,
- R4 and R5=independently of one another H or C1-C4-alkyl,
- Sach=a sugar,
- Y=S, O or NH,
- R4′=H or alkyl,
- v=1-100,
- a=0 or 1,
- n=2, 3, 4, 5 or 6,
- c=0 or 1,
- m=1, and
- o=1, 2, 3 or 4, and o=0 if R″=—(CH2CHR′″)m′—R″″, wherein where R′″ and/or R″″=alkyl, wherein one or more non-adjacent C atoms have been replaced by O or N,
- and wherein
- the following compounds are excluded:
- Rf′—O—CH2CH(OSO3Na)—CH2—O—CH2—CH—(C2H5)—C4H9,
- Rf′—O—CH2CH(OSO3H)—(CH2)5—CH3,
- Rf′—O—CO—CH2—CH(OSO3Na)—CO—O—Rf′,
- Rf″—CH2—CH(SO3Na)—Rf″,
- Rf″—CH2—CH(CH2SO3Na)—Rf″ and
- Rf″—CH—(CH3)CH(SO3Na)—Rf″,
- wherein
- Rf′=CF3CF2CF2—O—CF(CF3)—CH2—, and
- Rf″=CF3CF2CF2—O—CF(CF3)—CO—NHCH2CH2—O—CO—.
59 more elements
A compound of formula (I)
- (Rf-Aa-Cc)n-(spacer)m-Xo (I)
- wherein
- Rf=CF3—CF2—CF2—O—CF(CF3)—CH2—, CF3—CF2—CF2— or CF3—CF2—CF2—O—CF(CF3)—CO—,
- A=—O—CH2—CHR′—,
- R′=H or alkyl,
- C=alkylene, O, —OCO— or —NR″—,
- R″=H, alkyl or —(CH2CHR′″)m′—R″″,
- m′=an integer of 1 to 100,
- R′″ and R″″=independently of one another, H or alkyl, in which one or more non-adjacent C atoms are optionally replaced by O or N,
- spacer=a saturated or unsaturated, branched or unbranched hydrocarbon unit, optionally containing heteroatoms,
- X=—CH(OH)—CH2—NH-Sach or —Y—(CH2—CH2—O)vR,
- Sach=a sugar,
- Y=S, O or NH,
- R=H or CH3,
- v=1-15,
- a=0 or 1,
- n=1, 2, 3, 4, 5 or 6,
- c=0 or 1,
- m=0 or 1, and
- o=1, 2, 3 or 4, and o=0 if R″=—(CH2CHR′″)m′—R″″, wherein where R′″ and/or R″″=alkyl, wherein one or more non-adjacent C atoms have been replaced by O or N,
- wherein n≧2 if Rf =CF3—CF2—CF2—O—CF(CF3)—CO—,
- and wherein the following compounds are excluded
- CF3—CF2—CF2—O—CH2—CH2—OH,
- Rf′—O—CH2CH(OSO3Na)—CH2—O—CH2—CH—(C2H5)—C4H9,
- Rf′—O—CH2CH(OSO3H)—(CH2)5—CH3,
- Rf′—O—CO—CH2—CH(OSO3Na)—CO—O—Rf′,
- Rf″—CH2—CH(SO3Na)—Rf″,
- Rf″—CH2—CH(CH2SO3Na)—Rf″ and
- Rf″—CH—(CH3)CH(SO3Na)—Rf″,
- wherein
- Rf′=CF3CF2CF2—O—CF(CF3)—CH2—, and
- Rf″=CF3CF2CF2—O—CF(CF3)—CO—NHCH2CH2—O—CO—.
29 more elements
Dependencies are inferred from the claim text.