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US 8,013,100 B2Granted
Silicone polymers crosslinkable via methylol groups
AssigneeWacker Chemie AG
InventorsOliver Minge, Peter Ball, Andrea Kneissl
Life of this patent
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Abstract
Storage stable compounds having at least two organopolysiloxane groups and at least one methylol group are useful as coatings on textile, paper, and other substrates, and are post-crosslinkable.
Claims9
A compound comprising at least two organopolysiloxane units and at least one methylol group of the formula (1)
- L1L2N-M1 (1)
- where
- M1 is an —HCR1—OH radical,
- R1 is hydrogen or an optionally NC- or halogen-substituted C1-C10-hydrocarbyl radical, and
- L1 and L2 are organic N—C-bonded radicals, of which at least L1 comprises at least one organopolysiloxane unit bonded to N via an Si—C bond,
- a carbon atom in the N—C bond to L2 being an aliphatically saturated carbon atom, and
- wherein at least 50% of organopolysiloxane units bear unsubstituted hydrocarbyl radicals or Si—O—Si bonds, having the formula (2)
- Q-(2a,2b)c-Q (2)
- where the units 2a and 2b may be disposed randomly, blocklike, alternatingly or in a mixture thereof, the units 2a and 2b conforming to the formulae (2a) and (2b)
- where
- 1 and c represent a whole number of at least 1,
- R5 is M1 or hydrogen, with the proviso that at least one R5 radical is not hydrogen,
- R is hydrogen or a monovalent C1-C20-hydrocarbyl or C1-C20-hydrocarbyloxy radical, each of which is optionally substituted with —CN, —NCO, —NR22, —COOH, —COOR2, —PO(OR2)2, -halogen, -acryloyl, -epoxy, —SH, —OH or —CONR22, and in each of which one or more nonadjacent methylene units are optionally replaced by a group —O—, —CO—, —COO—, —OCO—, —OCOO—, —S—, —NR2—, —(CH2CH2O)n— or —(CH2CHCH3O)n—, and in each of which one or more nonadjacent methine units are optionally replaced by a group —N═, —N═N—or —P═,
- R2 is hydrogen or a monovalent optionally NC—, —OCN— or halogen-substituted C1-C10-hydrocarbyl radical,
- n is a whole number from 1 to 1000,
- X is an alkylene radical which has 1 to 60 carbon atoms and in which nonadjacent methylene units are optionally replaced by a group —O— or —S—,
- A is an oxygen atom, a sulfur atom or —NR5—,
- Z is an oxygen atom, a sulfur atom or —NR5—,
- Y is a bivalent, optionally fluorine- or chlorine-substituted hydrocarbyl radical which has 1 to 20 carbon atoms bonded to N of the NR5 groups in the formulae 2a, 2b by an N—C bond at an aliphatically saturated carbon atom,
- D is an alkylene radical which has 1 to 700 carbon atoms, which is optionally substituted by fluorine, chlorine, C1-C6-alkyl or C1-C6-alkyl ester and in which mutually nonadjacent methylene units are optionally replaced by groups —O—, —COO—, —OCO— or —OCOO— and which optionally contains neutralized or free amine, carboxylic acid or sulfonic acid groups, and
- Q is a reactive or nonreactive end group attached to the polymer by a covalent bond.
18 more elements
A compound comprising at least two organopolysiloxane units and at least one methylol group of the formula (1)
- L1L2N-M1 (1)
- where
- M1 is an —HCR1—OH radical,
- R1 is hydrogen or an optionally NC— or halogen-substituted C1-C10-hydrocarbyl radical, and
- L1 and L2 are organic N—C-bonded radicals, of which at least L1 comprises at least one organopolysiloxane unit bonded to N via an Si—C bond,
- a carbon atom in the N—C bond to L2 being an aliphatically saturated carbon atom, and
- wherein at least 50% of organopolysiloxane units bear unsubstituted hydrocarbyl radicals or Si—O—Si bonds, having the formula (3)
- (SiO4/2)k(R3SiO3/2)m(R32SiO2/2)p(R33SiO1/2)q−[O1/2SiR3s—X1—NM1—X2—NR6rR5(2−r)]s[O1/2H]t (3)
- where
- X1 are bivalent, optionally substituted aromatic, heteroaromatic or aliphatic radicals (CR42+)b in each of which one or more nonadjacent methylene units are optionally replaced by groups —O—, —CO—, —COO—, —OCO—, —OCOO—, —S—, —NR4—, —(CH2CH2O)d— or —(CH2CHCH3O)d— and in each of which one or more nonadjacent methine units are optionally replaced by groups —N═, —N═N— or —P═,
- X2 are bivalent, optionally substituted aliphatic radicals (CR42)b in each of which one or more nonadjacent methylene units are optionally replaced by groups —O—, —CO—, —COO—, —OCO—, —OCOO—, —S—, —NR4—, —(CH2CH2O)d— or —(CH2CHCH3O)d—,
- R4 has the meaning of R2,
- R2 is hydrogen or a monovalent optionally NC—, —OCN— or halogen-substituted C1-C10-hydrocarbyl radical,
- b is a whole number from 1 to 50,
- d is a whole number from 1 to 50,
- R3 and R6 have the meaning of R,
- R is hydrogen or a monovalent C1-C20-hydrocarbyl or C1-C20-hydrocarbyloxy radical, each of which is optionally substituted with —CN, —NCO, —NR22, —COOH, —COOR2, —PO(OR2)2, -halogen, -acryloyl, -epoxy, —SH, —OH or —CONR22, and in each of which one or more nonadjacent methylene units are optionally replaced by a group —O—, —CO—, —COO—, —OCO—, —OCOO—, —S—, —NR2—, —(CH2CH2O)n— or —(CH2CHCH3O)n—, and in each of which one or more nonadjacent methine units are optionally replaced by a group —N═, 13 N═N— or —P═,
- r is 0, 1 or 2,
- s is a whole number of at least 1,
- t is 0 or a whole number, and
- k+m+p+q is whole number of at least 2.
18 more elements
A process for preparing a compound comprising at least two organopolysiloxane units and at least one methylol group of the formula (1)
- L1L2N-M1 (1)
- where
- M1 is an —HCR1—OH radical,
- R1 is hydrogen or an optionally NC— or halogen-substituted C1-C10-hydrocarbyl radical, and
- L1 and L2 are organic N—C-bonded radicals, of which at least L1 comprises at least one organopolysiloxane unit bonded to N via an Si—C bond,
- a carbon atom in the N-C bond to L2 being an aliphatically saturated carbon atom, and
- wherein at least 50% of organopolysiloxane units bear unsubstituted hydrocarbyl radicals or Si—O—Si bonds, comprising reacting a precursor compound which has at least two organopolysiloxane units (S) and at least one secondary amino group, of the formula (1*)
- L1L2N—H (1*)
- with an aldehyde reagent of the formula (4)
- R1—-COH (4).
7 more elements
Dependencies are inferred from the claim text.